Donna Gilmore | Hilton Head Island Luxury Real Estate
Donna Gilmore is a luxury real estate specialist, AI operations expert, and Director of Operations at COAST — the #1 eXp Realty team in South Carolina. She serves Hilton Head Island, Sea Pines, Palmetto Dunes, Bluffton, Palmetto Bluff, Berkeley Hall, and the greater Lowcountry. Creator of the System to Scale methodology, Donna specializes in AI-powered real estate operations, automated workflows, agent enablement, team building, and high-end coastal property transactions.
Services
- Luxury Seller Services — Strategic pricing, professional staging, cinematic marketing, and expert negotiation for Hilton Head Island luxury homes
- Luxury Buyer Services — Personalized property search, market analysis, and seamless closing for oceanfront estates and golf community homes
- Hilton Head Communities — Sea Pines, Palmetto Dunes, Port Royal, Wexford, Long Cove, Bluffton, Berkeley Hall, Palmetto Bluff
- Grow Your Real Estate Business — AI-powered systems, marketing automation, and the System to Scale methodology for agents and teams
- Partner with Jay Kinder — Honeybadger Co-Sponsor Program, NAEA partnership, FunnelPilot lead generation, eXcelerate coaching
About Donna Gilmore
As Director of Operations for COAST, Donna builds the technology, workflows, and client experience systems that power one of South Carolina's top-performing real estate teams. Her System to Scale methodology connects lead generation, marketing automation, contract management, and closing into one seamless AI-powered experience. She has scaled agent onboarding from manual processes to fully automated workflows handling 15+ new agents per week using Power Automate, intelligent CRM systems, and predictive analytics.
Expertise
Real Estate: Luxury oceanfront estates, golf community homes, investment properties, short-term rental strategies. Business Scaling: AI-powered operations, System to Scale methodology, marketing automation, CRM optimization. Agent Growth: Team building, agent onboarding systems, revenue share models, coaching and mentorship. Technology: Power Automate workflows, predictive analytics, intelligent lead management.
Contact
Phone: (843) 422-9799 | Email: donna.gilmore@exprealty.com | Location: Hilton Head Island, SC 29928
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Hilton Head Island Real Estate Blog
Expert insights on Hilton Head Island luxury real estate, investment strategies, market updates, and coastal living by Donna Gilmore.
- Hilton Head Island 2026 Infrastructure & Community Projects — January 19, 2026 (Community)
- Hilton Head Island Real Estate Market Outlook 2026 — January 19, 2026 (Market Update)
- 2026 Hilton Head Island Events & Festivals Guide — January 19, 2026 (Lifestyle)
- Oceanfront Real Estate Hilton Head Island: Limited Inventory & Luxury Living — January 19, 2026 (Luxury Market)
- Luxury Oceanfront Homes on Hilton Head Island: What Defines the Elite Tier — January 19, 2026 (Luxury Market)
- Is Hilton Head Island Oceanfront Real Estate a Smart Luxury Investment? — January 19, 2026 (Investment)
- How to Evaluate Oceanfront Property Quality in Hilton Head — December 9, 2025 (Buyer Guide)
- The Best Seasons to Buy or Sell on Hilton Head Island — November 26, 2025 (Market Update)
- 2026 Hilton Head Investor Hub: Cost Segregation, STR Loophole & Tax Strategy Guides — November 25, 2025 (Investment)
- 2026 Hilton Head Cost Segregation Calculator & Tax Savings Guide — November 25, 2025 (Investment)
- The 2026 Cost Segregation Calculator for Hilton Head Real Estate Investors — November 25, 2025 (Investment)
- How to Qualify for STR Non-Passive Status or Real Estate Professional Status in 2026 — November 21, 2025 (Investment)
- Cost Segregation Case Studies for Hilton Head Investors: $400K vs $750K vs $1.2M — November 20, 2025 (Investment)
- Why Hilton Head Short-Term Rental Owners Benefit from the STR Loophole — November 19, 2025 (Investment)
- The 2026 Hilton Head Guide to Cost Segregation: The Tax Strategy Every Investor Should Know — November 18, 2025 (Investment)
- How to Evaluate Vacation-Rental Potential on Hilton Head Island — November 11, 2025 (Investment)
- 20 Smart Questions to Ask When Choosing a Real Estate Broker — November 11, 2025 (Agent Growth)
- The 5 Best Neighborhoods for Investment on Hilton Head Island — November 8, 2025 (Investment)
- Hilton Head Real Estate Market Update — November 2025 — November 4, 2025 (Market Update)
- Why Hilton Head Island's Real Estate Market Is One of the Strongest in the Southeast — November 4, 2025 (Market Update)
By Donna Gilmore | January 19, 2026 | Community | 6 min read
Hilton Head Island isn’t content to rest on its laurels. In 2026, the town is embarking on a range of transformative projects to safeguard its beaches, upgrade transportation, improve stormwater management, expand cultural facilities, create workforce housing and add new recreation amenities. These initiatives will improve quality of life for residents and enhance the visitor experience for years to come. Beach Renourishment & Shoreline Preservation The island’s beaches are its most valuable natural asset and require periodic renourishment to combat erosion. In 2026, a $47.5 million beach renourishment project will place more than two million cubic yards of sand along seven miles of shoreline. The project will widen beaches and rebuild dunes, providing critical habitat for wildlife and improved storm protection for oceanfront properties. Airport Expansion & Transportation Upgrades The Hilton Head Island Airport will complete a major expansion in April 2026. Improvements include an enlarged Transportation Security Administration checkpoint, new gate seating areas and the island’s first jet‑bridge boarding system. These upgrades will enhance passenger flow, reduce wait times and accommodate larger aircraft, making it easier for visitors and residents to access the island. Stormwater & Drainage Improvements To address increasing rainfall and protect neighborhoods from flooding, the town is investing in new pump stations and upgraded canal systems. Plans include raising low‑lying roads and installing sensors to monitor water levels in real time. These efforts will reduce flooding risk, protect wetlands and support the island’s resiliency goals. Coastal Discovery Museum Expansion The Coastal Discovery Museum at Honey Horn is undergoing a multi‑phase transformation. Enhancements include new exhibit galleries, expanded programming space, improved trail systems and a dedicated education building. Once complete, the museum will serve as a regional hub for environmental education and cultural heritage. Northpoint Workforce Housing & Community Initiatives Housing affordability remains a challenge for the island’s workforce. The Northpoint project aims to create 180 rental units, including 80 reserved for teachers, first responders and other critical workers. Additional units will be available at below‑market rates for families earning up to 80% of area median income. The development will include community amenities such as playgrounds, walking trails and a recreation center. Parks, Recreation & Pickleball Residents will soon enjoy new and improved recreational facilities. Plans include an 18‑court pickleball complex and expanded athletic fields at Bristol Sports Arena. Additional improvements include enhanced picnic areas, upgraded playground equipment and new walking paths. These investments reflect Hilton Head’s commitment to active lifestyles and community wellness. Trending Search Phrases Stay informed about local developments by following these search terms: Hilton Head infrastructure projects 2026 Hilton Head beach renourishment 2026 Hilton Head airport expansion 2026 Hilton Head stormwater improvements Northpoint workforce housing Hilton Head pickleball complex Coastal Discovery Museum expansion Frequently Asked Questions What are the major infrastructure projects on Hilton Head Island in 2026? Key projects include the $47.5 million beach renourishment program, a major expansion of the Hilton Head Island Airport, stormwater and drainage improvements, expansion of the Coastal Discovery Museum, development of Northpoint workforce housing and new recreational facilities. When will the airport expansion be completed? The airport upgrades, including the new jet‑bridge, are slated for completion in April 2026. How will the beach renourishment project benefit homeowners? Renourishment will widen beaches, rebuild dunes and strengthen storm protection for oceanfront properties while preserving wildlife habitat. About Donna Gilmore Donna Gilmore is a Realtor and the Director of Operations for COAST, the #1 eXp Realty team in South Carolina. She is an expert real estate mentor and team transition specialist, and creator of the Systems-to-Scale AI Implementation Method™, helping top agents and teams implement AI, automation, and high-performance...
By Donna Gilmore | January 19, 2026 | Market Update | 7 min read
The Hilton Head Island real estate market continues to hold strong in 2026 despite economic headwinds elsewhere. Buyer interest remains high, inventory has increased modestly and prices show resilience thanks to limited developable land and enduring demand. Below, we break down the market by property type, price trends, mortgage conditions and smart strategies for buyers seeking their place in this coastal paradise. Current Market Conditions According to the latest market data, inventory levels on Hilton Head Island have grown from the record lows of previous years but remain lean relative to demand. This modest increase has provided buyers with more choices without causing prices to soften. Single‑family homes continue to command premium pricing, while villas and condos offer more attainable entry points with strong rental potential. Single‑Family Homes vs. Condos & Villas Demand for single‑family homes remains robust due to the privacy, land and customization they provide. Many buyers are willing to pay a premium for larger lots, private pools and proximity to golf courses. Meanwhile, condos and villas continue to attract second‑home buyers and investors seeking rental income and lock‑and‑leave convenience. Popular communities such as Sea Pines, Palmetto Dunes and Shelter Cove offer desirable amenities and strong resale value. Pricing & Seller Performance Sales data shows that well‑priced homes are still selling near list price. Median sales prices for single‑family homes have stabilized after several years of rapid appreciation, while condos continue to see modest gains. Sellers who overprice their properties may find buyers less willing to negotiate in today’s environment of higher mortgage rates and more options. Mortgage Rates & National Context Mortgage rates have eased slightly from their 2025 highs. Nationally, the average 30‑year fixed rate hovered around 6.16% as of January 8, 2026. While rates remain elevated compared with the sub‑4% rates of a few years ago, they have not deterred well‑qualified buyers from entering the Hilton Head market. National existing‑home sales totaled 4.13 million in November 2025 with 1.43 million homes on the market, reflecting a gradual return to historical norms. Buyer Strategies for 2026 Buyers can improve their odds of success by preparing before entering the market: Get pre‑approved: Secure financing early to demonstrate seriousness and strengthen your negotiating position. Set a realistic budget: Factor in higher interest rates and maintenance costs when determining how much house you can afford. Clarify non‑negotiables: Decide which features—such as location, amenities or square footage—are essential so you can move quickly when the right property appears. Work with a local expert: An experienced agent with knowledge of Hilton Head’s micro‑markets can help you uncover off‑market opportunities and navigate community regulations. Trending Search Phrases These keywords reflect what buyers are searching for in 2026: Hilton Head real estate market 2026 Hilton Head home prices 2026 Hilton Head condos vs houses Hilton Head mortgage rates 2026 Sea Pines homes for sale 2026 Palmetto Dunes villas Hilton Head investment property Hilton Head real estate forecast Frequently Asked Questions Is the Hilton Head Island real estate market strong in 2026? Yes. Despite higher mortgage rates, the market remains resilient. Inventory has increased modestly, but demand still exceeds supply for well‑located homes. Are home prices rising or stabilizing? Prices for single‑family homes have stabilized while condos and villas see modest gains. Pricing depends on location, condition and community amenities. Should I buy now or wait? Waiting for significant price drops may not be wise in a market with limited land and sustained demand. If you find a property that meets your criteria and fits your budget, consider moving forward. Which is better—single‑family homes or condos? Single‑family homes offer privacy and land but come...
By Donna Gilmore | January 19, 2026 | Lifestyle | 5 min read
Hilton Head Island may be best known for its pristine beaches and golf courses, but it also boasts a calendar packed with festivals and special events. In 2026, the island’s cultural and culinary scene is more vibrant than ever, with celebrations that honor its Gullah heritage, showcase award‑winning chefs and vintners, host world‑class sporting tournaments and bring families together under the stars. Here’s your month‑by‑month guide to the island’s most anticipated events. Gullah Celebration | January – February The Hilton Head Island Gullah Celebration is recognized by the Southeast Tourism Society as a Top 20 event. Held throughout January and February, it celebrates the unique African‑American Gullah culture through art exhibits, music performances, food tastings and interactive tours. Visitors can sample traditional dishes like shrimp and grits, learn the history of the Gullah people and participate in workshops hosted by local artisans. Hilton Head Island Seafood Festival | February Known as one of the island’s premier culinary events, the week‑long Hilton Head Island Seafood Festival features celebrity chef demonstrations, wine pairings, live music and tasting events. Guests savor fresh oysters, shrimp and Lowcountry boils while mingling with national and regional chefs. Proceeds support the David M. Carmines Memorial Foundation, benefiting local charities. Hilton Head Wine & Food Festival | March In March, the Hilton Head Wine & Food Festival celebrates its 40th year. This iconic event includes the Grand Tasting, Public Tasting, wine education sessions and silent auctions. Over 250 wines and local dishes are on offer, drawing enthusiasts and sommeliers from around the country. RBC Heritage Presented by Boeing | April 13–19, 2026 Hilton Head Island’s signature sporting event is the RBC Heritage, a PGA TOUR tournament held at Harbour Town Golf Links. From April 13–19, 2026, the world’s top golfers compete for the plaid jacket while fans enjoy hospitality suites, pro‑ams and a family‑friendly Heritage Lawn. Accommodations fill quickly during tournament week, so plan lodging well in advance. Pedal Hilton Head | Memorial Day Weekend Pedal Hilton Head is a scenic bike ride benefiting the Boys & Girls Club of Hilton Head Island. Riders choose routes ranging from 10 to 62 miles, touring the island’s beaches, maritime forests and waterfront communities. The ride culminates with a Post‑Ride Party featuring live music, food trucks and family activities. HarbourFest at Shelter Cove | June – August Every Tuesday during the summer, HarbourFest transforms Shelter Cove Harbour & Marina into an evening of fireworks, live bands, arts and crafts vendors and children’s entertainment. The festival’s centerpiece is a spectacular fireworks show over Broad Creek. Arrive early to secure parking and seats along the promenade. Crescendo & Lantern Parade | October – November Fall brings the island‑wide arts and cultural festival known as Crescendo. Performances range from chamber music and jazz concerts to theatre and dance. The festival culminates in the colourful Lantern Parade, where residents and visitors carry handmade lanterns down Pope Avenue to Coligny Beach in a dazzling procession. Concours d’Elegance & Motoring Festival | November Car enthusiasts flock to Hilton Head in November for the Concours d’Elegance & Motoring Festival. Ranked among the nation’s top automotive events, it showcases rare vintage automobiles and aircraft in a luxurious setting. Highlights include the Aero Expo at the airport and Sunday’s elegant Concours show on Port Royal Golf Club’s fairways. Planning Tips & Travel Insights To maximize your experience, book accommodations early for high‑demand events like the RBC Heritage and Concours d’Elegance. Many festivals offer VIP packages with behind‑the‑scenes access and reserved seating. While peak events draw large crowds, off‑season celebrations provide intimate experiences and special offers on lodging and dining. Trending...
By Donna Gilmore | January 19, 2026 | Luxury Market | 6 min read
Oceanfront Real Estate on Hilton Head Island: Why Luxury Buyers Are Moving Fast Oceanfront real estate on Hilton Head Island sits at the pinnacle of coastal luxury. Strict zoning rules, environmental protections and a deliberately low‑density development strategy have preserved the island’s shoreline. As a result, true oceanfront homes remain scarce and command both premium prices and enduring value. This scarcity, coupled with lifestyle appeal, explains why well‑qualified buyers continue to compete aggressively for beachfront properties. Market Dynamics on Hilton Head Island The 2026 real‑estate market on Hilton Head Island shows healthy buyer demand and stable pricing. Inventory has increased modestly, giving buyers more choice in single‑family homes and condos. Even with more listings, oceanfront properties remain limited because no new beachfront land can be created. Median sales prices are steady, and sellers who price their homes appropriately continue to see strong results. Single‑family homes, in particular, outperform condos thanks to sustained demand. Factors Driving Demand Several factors drive demand for oceanfront real estate: Primary or secondary residence: Executives, entrepreneurs and retirees view oceanfront homes as both a retreat and a strategic asset. Lifestyle: Buyers are drawn to world‑class golf, boating and marinas, tennis and pickleball facilities and year‑round outdoor living. Legacy ownership: Scarcity makes these properties ideal for passing wealth across generations. Wealth diversification: Oceanfront homes provide a tangible hedge against inflation and financial market volatility. Popular Communities and Property Types Demand is strongest in the island’s most prestigious communities. Buyers often focus on: Sea Pines, Palmetto Dunes and Hilton Head Plantation: Gated communities offering golf, beach clubs and private marinas. Wexford, Long Cove and Port Royal: Highly exclusive neighborhoods with deepwater access and custom estates. Indigo Run, Spanish Wells, Shipyard and Forest Beach: Areas prized for access to golf courses, waterfront views and beach proximity. Oceanfront condos and villas: Condos appeal to second‑home buyers seeking low maintenance and potential rental income. Oceanfront vs. Waterfront Online searchers often confuse oceanfront and waterfront homes. The distinction matters: Oceanfront homes sit directly on the Atlantic Ocean and typically offer unobstructed views and private beach access. There are no roads or structures between the home and the ocean. Waterfront homes may front lagoons, marshes or tidal creeks. They can offer beautiful scenery but do not command the same premiums or scarcity as oceanfront properties. Investment Outlook Oceanfront real estate has historically performed well during market shifts. Scarcity, coupled with strong demand from high‑net‑worth buyers, supports price stability and long‑term appreciation. Inventory levels for oceanfront homes remain low relative to demand, and homes priced realistically sell quickly. Buyers should still consider flood‑zone elevations, insurance requirements and maintenance costs when evaluating a purchase. Frequently Asked Questions What is oceanfront real estate on Hilton Head Island? Oceanfront real estate refers to homes located directly on the Atlantic Ocean with unobstructed views and private beach access. Why are oceanfront homes on Hilton Head Island so desirable? Limited inventory, strict development protections and a lifestyle rich in golf, beaches and boating make these properties highly desirable. Are oceanfront properties on Hilton Head Island a good investment? Yes. Oceanfront homes benefit from scarcity and sustained demand, making them attractive for long‑term appreciation and legacy ownership. About Donna Gilmore Donna Gilmore is a Realtor and the Director of Operations for COAST, the #1 eXp Realty team in South Carolina. She is an expert real estate mentor and team transition specialist, and creator of the Systems-to-Scale AI Implementation Method™, helping top agents and teams implement AI, automation, and high-performance systems to grow smarter and scale faster. If you're considering a move, exploring short-term rentals, or looking to level up your...
By Donna Gilmore | January 19, 2026 | Luxury Market | 6 min read
Not all oceanfront homes are equal. On Hilton Head Island, luxury oceanfront properties represent the top tier of coastal real estate. These homes combine sophisticated design, elevated construction and unparalleled privacy. Buyers value not only the views but also the craftsmanship and amenities that distinguish elite properties. Understanding what sets these homes apart helps buyers navigate the market with confidence. What Sets Luxury Oceanfront Homes Apart Luxury oceanfront homes on Hilton Head Island are defined not by price alone but by execution, location and permanence. Elite buyers expect elevated construction engineered for coastal conditions, architectural integrity that respects the environment and seamless indoor‑outdoor living. These homes are designed to endure—physically and financially. Architectural Excellence and Engineering Elevated foundations and flood mitigation: Homes are built on raised foundations or pilings to protect against storm surge and meet FEMA requirements. Panoramic windows: Floor‑to‑ceiling glass captures uninterrupted ocean views and natural light. High‑quality materials: Impact‑resistant glass, marine‑grade metals and moisture‑resistant woods protect against salt air and humidity. Sustainable design: Many new builds incorporate solar panels, geothermal systems and eco‑friendly materials. Luxury Amenities and Lifestyle Resort‑style pools and spas Expansive outdoor kitchens and entertaining terraces Private beach walkovers and dune decks Smart‑home automation and security systems Dedicated wellness rooms for yoga, Pilates or massage Buyers also choose communities that offer golf courses, marinas, tennis clubs and bike trails. Prime Communities for Luxury Oceanfront Living Sea Pines: Known for its Harbour Town marina, golf courses and exclusive beach clubs. Palmetto Dunes: Offers three championship golf courses, a deepwater marina and miles of beaches. Wexford and Long Cove: Gated communities with private harbours and custom estates. Port Royal and Palmetto Hall: Provide private beach access and a quieter residential setting. Trending Design Searches & Phrases Recent search data reveal the terms buyers use when looking for luxury oceanfront homes. Incorporate these phrases naturally into your listings and blog posts: Hilton Head Island luxury oceanfront homes Sea Pines oceanfront estates Palmetto Dunes beachfront villas Modern coastal design Hilton Head Lowcountry luxury homes Inventory & Market Conditions Inventory remains extremely limited. Hilton Head’s zoning restrictions and environmental protections prevent overdevelopment and preserve long‑term value. While inventory for condos and villas has increased, the most desirable oceanfront estates often sell off‑market or through private networks. Well‑priced homes still receive strong buyer interest and close quickly. Frequently Asked Questions What defines a luxury oceanfront home on Hilton Head Island? Direct beach access, unobstructed ocean views, elevated construction, high‑end materials and resort‑style amenities distinguish luxury oceanfront homes. Which communities have the best luxury oceanfront properties? Sea Pines, Palmetto Dunes, Wexford, Long Cove and Port Royal are among the most prestigious options. Why is luxury oceanfront inventory limited? Environmental protections and zoning restrictions cap new construction, ensuring scarcity and long‑term value for existing homes. About Donna Gilmore Donna Gilmore is a Realtor and the Director of Operations for COAST, the #1 eXp Realty team in South Carolina. She is an expert real estate mentor and team transition specialist, and creator of the Systems-to-Scale AI Implementation Method™, helping top agents and teams implement AI, automation, and high-performance systems to grow smarter and scale faster. If you're considering a move, exploring short-term rentals, or looking to level up your real estate business, Donna can help you make data-driven decisions and avoid costly mistakes. Schedule a Consultation → Related Articles → Oceanfront Real Estate Hilton Head Island – Limited Inventory & Luxury Living → Is Hilton Head Island Oceanfront Real Estate a Smart Luxury Investment? → More Hilton Head Island Real Estate Articles...
By Donna Gilmore | January 19, 2026 | Investment | 5 min read
Luxury investors often ask whether Hilton Head Island oceanfront real estate is a wise long‑term investment. The answer is a resounding yes — provided buyers understand the market dynamics and plan for both lifestyle enjoyment and financial performance. This post examines current pricing trends, rental opportunities, ownership costs and strategic considerations for investors. Current Market & Pricing Trends Market data entering 2026 show that inventory has increased slightly but remains balanced. Single‑family homes continue to lead the market, outperforming condos. Well‑priced properties still achieve high percentages of list price. Mortgage rates have eased compared to the previous year, encouraging qualified buyers to act now and secure their dream oceanfront home. Rental Potential & Income Strategies Many luxury buyers leverage oceanfront homes as both a personal retreat and a source of income. Key points include: Short‑term rentals: Hilton Head is a popular vacation destination. Homes in communities like Palmetto Dunes and Sea Pines can command premium weekly rates during peak season. Long‑term rentals: Some investors prefer longer leases for stability, targeting retirees and executives relocating for work. Owner use vs. rental balance: Owners should consider how often they plan to use the home personally versus renting it. Taxes and insurance may vary based on usage. Key Considerations Before Investing Flood‑zone and elevation: Verify the property’s elevation and flood zone. Elevated construction and proper drainage reduce insurance costs. Insurance: Premiums for oceanfront homes can be higher. Buyers should budget for wind and flood insurance. Maintenance: Salt air and humidity require regular upkeep. Plan for exterior painting, roof maintenance and HVAC service. Community rules: Rental regulations vary by community. Some gated neighborhoods limit short‑term rentals. Search Phrases & Buyer Intent Investors researching the market often use phrases like: Hilton Head oceanfront investment property Hilton Head Island vacation rental homes Oceanfront condos for sale under $1M Second‑home investment Hilton Head Real estate market report Hilton Head 2026 Long‑Term Outlook The combination of limited supply, lifestyle appeal and strong buyer demand suggests oceanfront homes will retain their value for years to come. Investors with a horizon of five to ten years or more are well positioned to benefit from both appreciation and rental income, especially as Hilton Head Island continues to attract well‑qualified buyers and relocation households. Frequently Asked Questions Is Hilton Head Island oceanfront real estate a good investment? Yes. Limited inventory, stable pricing, strong buyer demand and long‑term appreciation make oceanfront real estate a desirable luxury investment. Can oceanfront homes be rented for income? Many oceanfront homes are rented seasonally. Rental regulations vary by community, so investors should review rules before purchasing. What should buyers consider before investing in oceanfront property? Elevation, flood‑zone status, insurance costs, maintenance planning and community rental regulations are important factors to evaluate. About Donna Gilmore Donna Gilmore is a Realtor and the Director of Operations for COAST, the #1 eXp Realty team in South Carolina. She is an expert real estate mentor and team transition specialist, and creator of the Systems-to-Scale AI Implementation Method™, helping top agents and teams implement AI, automation, and high-performance systems to grow smarter and scale faster. If you're considering a move, exploring short-term rentals, or looking to level up your real estate business, Donna can help you make data-driven decisions and avoid costly mistakes. Schedule a Consultation → Related Articles → Oceanfront Real Estate Hilton Head Island – Limited Inventory & Luxury Living → Luxury Oceanfront Homes on Hilton Head Island: What Defines the Elite Tier → More Hilton Head Island Real Estate Articles...
By Donna Gilmore | December 9, 2025 | Buyer Guide | 7 min read
About Donna Gilmore Donna Gilmore is the Director of Operations for COAST, the #1 eXp real estate team in South Carolina. With over a decade in construction operations, she specializes in luxury Hilton Head real estate, market timing strategy, and investment analysis.Schedule a Consultation →Continue Reading Related Articles01 🌴 3. The Best Seasons to Buy or Sell on Hilton Head Island in 2025 Discover why timing matters. This guide outlines peak buyer demand, off-season pricing advantages and insider tips for choosing the best months to transact on Hilton Head.Read Article02 How to Qualify for STR Non‑Passive Status or Real Estate Professional Status in 2026) Understand the IRS rules for short‑term rental tax benefits and learn how high‑net‑worth investors on Hilton Head can achieve non‑passive status to maximize deductions.Read Article)03 🌴 1. The 5 Best Neighborhoods for Investment on Hilton Head Island in 2025 Explore the top communities for investors seeking strong returns, lifestyle amenities and long‑term growth on Hilton Head Island.Read ArticleExpert Insight Choosing an oceanfront home is about more than a stunning view. “You want a property that’s built to withstand coastal conditions and hold its value for decades,” says Donna Gilmore. Owning a beachfront home on Hilton Head Island is a dream for many, but seaside living comes with unique challenges. Salt air, humidity and storms can accelerate wear on materials and structures, which means evaluating quality is essential to protecting your investment. In this guide, you’ll learn the environmental, structural and maintenance factors that determine whether a coastal property is a sound purchase. From understanding erosion patterns to inspecting foundation materials and hurricane‑proof windows, our checklist helps you look beyond aesthetics. We’ll also discuss how to anticipate future costs for insurance and upkeep, ensuring your beachside oasis remains a source of joy—not unexpected expenses. With a decade of construction operations and luxury real estate experience, Donna Gilmore shares her step‑by‑step process to assess oceanfront homes. You’ll come away prepared to evaluate properties like a pro or know when it’s time to call in an expert. Location & Environmental Considerations The first step in evaluating any oceanfront property is understanding its site. Elevation and distance from the dune line influence flood risk and storm surge exposure. Properties situated behind healthy dune systems or on higher bluffs are better protected against erosion and sea‑level rise. Ask for elevation certificates and consult FEMA flood maps to gauge risk levels. Orientation also matters: a home facing due east may enjoy sweeping sunrise views but endure harsher wind and salt spray, while a home tucked behind native vegetation might sacrifice some view for extra protection. Don’t forget to research beach nourishment projects, shoreline stabilization efforts and any public access easements that could affect privacy.Donna's Expert Perspective A prime oceanfront site balances view, elevation and protection. The prettiest stretch of sand may not be the smartest place to build if erosion is a constant battle. Environmental Factors to Check History of shoreline erosion and recent nourishment projects. Elevation relative to FEMA flood zones (AE, VE, etc.). Proximity to vegetation, dune systems and public walkways. Prevailing winds and direction of storms during hurricane season. Distance from high‑tide line and setback requirements. Construction & Materials: Building for Coastal Resilience Oceanfront homes must be engineered to withstand strong winds, moisture and salt corrosion. Look for deep pile foundations or elevated pilings that keep living spaces above storm surge. Reinforced concrete or steel framing resists high winds better than conventional wood framing. Windows and doors should be impact‑rated for hurricane‑prone regions, with corrosion‑resistant hardware. Exterior materials are equally important. Fiber‑cement siding, stucco over masonry and tropical hardwoods...
By Donna Gilmore | November 26, 2025 | Market Update | 6 min read
About Donna Gilmore Donna Gilmore is the Director of Operations for COAST, the #1 eXp real estate team in South Carolina. With over a decade in construction operations, she specializes in luxury Hilton Head real estate, market timing strategy, and investment analysis. Schedule a Consultation → Related Articles → How to Qualify for STR Non-Passive Status in 2026 → Cost Segregation Case Studies for Hilton Head Investors → Why Hilton Head STR Owners Benefit from the STR Loophole The Best Seasons to Buy or Sell a Home on Hilton Head Island (2025–2026 Guide) Timing matters in real estate—especially in resort-driven markets like Hilton Head Island. Whether you're buying, selling, or investing in short-term rentals, understanding the island’s seasonal patterns can help you make smarter, more profitable decisions. This 2025–2026 guide breaks down Hilton Head’s market seasonality, including when buyers face the least competition, when sellers see the strongest demand, and how tourism patterns influence pricing and negotiation power. Why Seasonality Plays a Big Role on Hilton Head Hilton Head isn’t a typical suburban market. It’s influenced by: Tourism cycles (spring and summer peaks) Snowbird migration (winter visitors) Rental demand curves (prime STR months) Second-home buyer traffic (spring + fall) Because of these factors, the “best” season to buy or sell depends on your goals: Buyers: prioritize inventory and price flexibility Sellers: prioritize demand and buyer competition Investors: prioritize STR occupancy & revenue timing The Best Season to Buy on Hilton Head Best time to buy: September through February Fall and winter provide the best buying conditions for both primary-home buyers and investors. Here’s why: More motivated sellers after the tourism peak Less competition from vacation-home buyers More negotiable pricing as days on market increase Easier access for inspections when homes aren’t booked Many investors also prefer to close in Q4 for tax planning reasons—especially when planning renovations, depreciation, or cost segregation strategies. The Best Season to Sell on Hilton Head Best time to sell: March through July Sellers see the strongest activity during the spring and early summer seasons. Why? Tourism increases dramatically—more buyers see homes in person Demand spikes for second homes and STR-friendly properties Longer daylight hours improve showings and curb appeal Families and retirees time their moves with school and lifestyle schedules Properties near the beach (Sea Pines, Palmetto Dunes, Folly Field, Shipyard) often perform especially well during these months. How STR Seasonality Affects Buyer Strategy If you're buying a short-term rental investment, timing can dramatically impact rental income and your first-year ROI. Buying before peak season allows you to capture spring + summer revenue Buying after peak season gives you more negotiation power Closing in Q4 allows investors to take advantage of tax benefits (like bonus depreciation) Pro tip: Many STR buyers aim to close between November–February to renovate before spring and capture high-season returns. How Seasonality Affects Sellers Sellers should consider aligning their listing strategy with the buyer surge. Listing during spring or early summer often leads to: Higher offer activity More competitive bidding Better visibility to vacationers who fall in love with the area Even if you're selling a property that is currently an STR, coordinating showings around bookings is easier during shoulder seasons. Best Time to Buy or Sell by Property Type Beach Villas & Condos Best to buy: Late fall when rentals slow Best to sell: Early spring when tourism spikes Single-Family Homes in Sea Pines, Palmetto Dunes, Shipyard Best to buy: Winter or early fall Best to sell: March–June Off-Island Homes (Bluffton) Best to buy: Year-round—market is less seasonal Best to sell: Spring FAQs About Hilton Head Seasonality What month is...
By Donna Gilmore | November 25, 2025 | Investment | 8 min read
"2026 Hilton Head Investor Tax Advantage Series Cost Segregation & STR Loophole Hub for Hilton Head Investors This page brings together all of my 2026 guides on cost segregation, the STR loophole, and real-world case studies for Hilton Head and Bluffton investment properties. If you're a short-term rental owner, high-income earner, or investor planning a coastal purchase, start here. Use this hub to move through the series in order, jump straight to the calculator, or share it with your CPA and lender. Part 1: The 2026 Hilton Head Guide to Cost Segregation Learn what cost segregation is, why it’s an IRS-approved strategy, and how a $400,000 Hilton Head rental can legally generate nearly $70,000 in first-year depreciation. This is your foundation for everything else in the series. 👉 [Read Part 1: Cost Segregation 101 for Hilton Head Investors →]() Part 2: The STR Loophole – Why Hilton Head Short-Term Rentals Get Extra Tax Benefits Discover how the STR loophole works, what the IRS considers a short-term rental, and how Hilton Head owners can use STR non-passive status to offset W-2 and active income. This is essential if you’re using Airbnb/VRBO as part of your tax strategy. 👉 [Read Part 2: STR Loophole & Material Participation →]() Part 3: Case Studies – $400K, $750K & $1.2M Hilton Head Properties Compared See side-by-side examples of how cost segregation performs at three real-world price points. Understand how first-year depreciation, tax savings, and ROI change as you move from condos to luxury STRs with pools and ocean proximity. 👉 [Read Part 3: 2026 Hilton Head Cost Segregation Case Studies →]() Part 4: How to Qualify for STR Non-Passive Status or Real Estate Professional Status (REPS) in 2026 Learn the differences between STR non-passive status and Real Estate Professional Status, who each is best for, and how they can unlock the ability to use cost segregation to offset W-2 and other active income. 👉 [Read Part 4: STR Non-Passive vs Real Estate Professional Status →]() Interactive Tool: 2026 Cost Segregation Calculator for Hilton Head Ready to see how the numbers might look on your own property? Use the interactive calculator to estimate depreciable basis, bonus depreciation, total first-year deductions, and potential tax savings for any price point. 👉 [Use the 2026 Cost Segregation Calculator →]() Downloadable Guide (Optional): 2026 Hilton Head Investor Tax Advantage Playbook Turn this series into a shareable, printable playbook that you can review with your CPA, lender, or investing partners. The PDF version walks through the same concepts with consolidated examples and checklists. 👉 [Get the PDF: 2026 Hilton Head Investor Tax Advantage Playbook →]() Who This Series Is Designed For This hub is built for: Short-term rental (STR) owners in Hilton Head, Bluffton, and the Lowcountry High-income W-2 earners looking for legal tax strategies Real estate investors comparing different price tiers and property types Second-home owners considering renting their property part-time CPAs, lenders, and advisors working with coastal real estate investors If you’re planning to buy, sell, or scale a Hilton Head STR portfolio, this series gives you the language, examples, and frameworks to have smarter conversations with your tax and finance team. Want a Property-Specific Cost Seg & STR Tax Strategy? I help investors analyze real Hilton Head and Bluffton properties using income projections, cost segregation estimates, STR tax strategies, and long-term scaling plans. 👉 I can run a custom analysis for your next purchase—or your current portfolio.[Request Your Custom STR & Cost Seg Review →]() About the Author By: Donna Gilmore – Realtor & Director of Operations for the #1 eXp Team in South Carolina Expert Real Estate...
By Donna Gilmore | November 25, 2025 | Investment | 7 min read
Start Here: Estimate Your Depreciation & Tax Savings Use this calculator to estimate first-year bonus depreciation, total deductions, and potential tax savings on a Hilton Head or Bluffton investment property. It’s designed for short-term rentals, long-term rentals, and second homes used as STRs—and uses 2026 cost segregation and bonus depreciation assumptions. Watch: How to Use This Calculator (Optional) Record a 45–60 second video and embed it here using your kvCORE video or YouTube embed code. Use this script as your outline: Introduce yourself as Donna Gilmore and your role. Explain that cost segregation can dramatically improve cash flow. Tell viewers to enter purchase price, land %, accelerated %, bonus %, and tax rate. Explain that the calculator will estimate first-year depreciation and tax savings. Invite them to request a custom report once they see their numbers. Cost Segregation Calculator (2026) Estimate first-year bonus depreciation and tax savings for your Hilton Head or Bluffton investment property.Purchase Price ($) Land % (0.20 = 20%) Accelerated % (0.25 = 25%) Bonus Depreciation % (0.60 = 60%) Tax Rate (0.30 = 30%) Calculate Tax Savings ResultsDepreciable Basis $0Accelerated Assets $0Bonus Depreciation $0Standard Depreciation (27.5 yrs) $0Total 1st-Year Depreciation $0Estimated Tax Savings (Year One) $0 This calculator is for educational estimates only and does not replace a formal cost segregation study or professional tax advice. How to Interpret Your Results Once you’ve entered your property details and generated results, pay close attention to your total first-year depreciation and estimated tax savings. These numbers can help you: Compare different purchase prices and renovation plans Decide whether a cost segregation study is worth pursuing See how a Hilton Head STR might reduce your overall tax bill Have a more informed conversation with your CPA For a deeper dive, compare your results against my real Hilton Head case studies showing how cost segregation performs on $400K, $750K, and $1.2M properties. 👉 Read the 2026 Cost Segregation Case Study Guide Request a Free Property-Specific Cost Segregation Estimate Want more than a rough estimate? I’ll run a custom analysis for your Hilton Head or Bluffton property using real rental assumptions, STR tax strategies, and cost segregation projections.Name: Email: Phone (optional): Property Address or MLS #: Approximate Purchase Price: Disclaimer This calculator and article are for educational purposes only and do not constitute tax, financial, or legal advice. Always consult a qualified CPA, tax advisor, or attorney before making decisions based on these estimates. About the Author By: Donna Gilmore – Realtor & Director of Operations for the #1 eXp Team in South Carolina Expert Real Estate Mentor & Team Transition Specialist | AI Systems Strategist for Top-Producing Agents & Teams | Creator of the Systems-to-Scale AI Implementation Method™ Helping agents, teams, and leaders implement AI, automation, and high-performance systems to grow smarter, scale faster, and dominate their markets. Compare Your Results to Real Properties See how your estimated depreciation and tax savings stack up against real Hilton Head investments at $400K, $750K, and $1.2M price points. View the 2026 Case Study Guide → Thinking About Buying in 2026? I help Hilton Head and Bluffton investors analyze deals using real STR numbers, cost segregation, and long-term wealth strategies. If you’re considering a property, let’s run the numbers together....
By Donna Gilmore | November 25, 2025 | Investment | 6 min read
Cost segregation is one of the most powerful tax strategies available to Hilton Head and Bluffton real estate investors. By accelerating depreciation on certain components of a property, investors can create large first-year deductions and significantly reduce taxable income. This article gives you a simple calculator-style framework to estimate: Your depreciable basis Accelerated (bonus-eligible) assets First-year bonus depreciation Total first-year depreciation Estimated tax savings Whether you’re analyzing a $400,000 villa or a $1.3M luxury STR, these steps help you quickly see the potential impact of cost segregation in 2026. Step 1: Calculate Your Depreciable Basis Not all of a property’s purchase price can be depreciated. The land portion is not depreciable, so the first step is to remove land value. Formula: Depreciable Basis = Purchase Price × (1 – Land Percentage) In many Hilton Head transactions, land is often estimated between 15–25% of the purchase price. Example: Purchase price: $800,000 Land %: 20% (0.20) Depreciable Basis = $800,000 × (1 – 0.20) = $640,000 Step 2: Estimate Accelerated Property (5, 7, and 15-Year Assets) A cost segregation study identifies components that can be depreciated over shorter timelines, typically: 5-year property: Appliances, carpets, cabinets, fixtures, some interior finishes 15-year property: Landscaping, patios, driveways, some site improvements In many Hilton Head resort-style properties, these accelerated components often total between 15%–30% of the depreciable basis. Example: Depreciable basis: $640,000 Accelerated % (5and 15-year): 25% (0.25) Accelerated Assets = $640,000 × 0.25 = $160,000 Step 3: Apply the 2026 Bonus Depreciation Percentage Bonus depreciation allows a large portion of accelerated assets to be written off in year one. The exact percentage can change with legislation, but many 2026 scenarios model 60%–80% bonus depreciation on qualified assets. To be conservative, you might assume 60% bonus depreciation when estimating. Formula: Bonus Depreciation = Accelerated Assets × Bonus Depreciation % Example: Accelerated assets: $160,000 Bonus %: 60% (0.60) Bonus Depreciation = $160,000 × 0.60 = $96,000 Step 4: Calculate Standard Depreciation The remaining building basis is still depreciated over 27.5 years (for residential property). Formula: Standard Depreciation = Depreciable Basis ÷ 27.5 Example: Depreciable basis: $640,000 Standard Depreciation = $640,000 ÷ 27.5 ≈ $23,273 Step 5: Determine Total First-Year Depreciation This is where cost segregation becomes very compelling. Formula: Total First-Year Depreciation = Bonus Depreciation + Standard Depreciation Example: Bonus depreciation: $96,000 Standard depreciation: $23,273 Total First-Year Depreciation = $96,000 + $23,273 = $119,273 Step 6: Estimate Your Tax Savings Finally, multiply your total first-year depreciation by your effective tax rate. Formula: Estimated Tax Savings = Total Depreciation × Tax Rate Most high-income STR investors fall in the 28%–35% effective range. For modeling, 30% is a common assumption. Example: Total depreciation: $119,273 Tax rate: 30% (0.30) Tax Savings = $119,273 × 0.30 ≈ $35,782 So in this example, an $800,000 Hilton Head property could potentially generate around $36,000 in first-year tax savings—depending on your exact tax profile. Quick Reference Table: Cost Segregation Scenarios | Purchase Price | Basis After Land (80%) | Accelerated % | Approx. Bonus Depreciation (60%) | Est. Total Year-One Depreciation | Est. Tax Savings @ 30% | | $500,000 | $400,000 | 20% | ~$48,000 | ~$74,545 | ~$22,363 | | $900,000 | $720,000 | 25% | ~$108,000 | ~$161,000 | ~$48,300 | | $1,300,000 | $1,040,000 | 30% | ~$187,200 | ~$272,000 | ~$81,600 | These numbers are estimates, but they highlight how powerful cost segregation can be for Hilton Head investors at different price points. Who Benefits Most from Cost Segregation in Hilton Head? Short-term rental (STR) owners who qualify for STR non-passive status High-income W-2 earners (medical, tech, finance, executives)...
By Donna Gilmore | November 21, 2025 | Investment | 7 min read
About Donna Gilmore Donna Gilmore is the Director of Operations for COAST, the #1 eXp real estate team in South Carolina. She specializes in Hilton Head investment properties, short-term rental strategy, and tax optimization for high-net-worth investors. Schedule an Investment Consultation → Related Articles → Why Hilton Head STR Owners Benefit from the STR Loophole → Cost Segregation Case Studies for Hilton Head Investors → The Best Seasons to Buy or Sell on Hilton Head Island How to Qualify for STR Non-Passive Status or Real Estate Professional Status in 2026 (Hilton Head Investor Guide) If you're investing in a Hilton Head or Bluffton short-term rental (STR), understanding whether you qualify for STR non-passive status or Real Estate Professional Status (REPS) can dramatically affect your tax savings—especially when combined with cost segregation and bonus depreciation. This guide breaks down both classifications, how they differ, and how Hilton Head investors can use them to reduce taxable income in 2026. STR Non-Passive Status vs Real Estate Professional Status (REPS): What’s the Difference? | Category | STR Non-Passive | Real Estate Professional (REPS) | | Applies to | Short-term rentals only | All rental properties | | Average stay requirement | 7 days or less | Not required | | Can offset W-2 income? | Yes | Yes | | Hours requirement | 100+ hours (and more than anyone else) OR 500 hours | 750+ hours + majority of working time | | Difficulty | Easy–Moderate | Hard (full-time real estate) | Most Hilton Head STR owners find the STR loophole far easier to qualify for than REPS. How to Qualify for STR Non-Passive Status Your short-term rental must meet the IRS definition: Average stay is 7 days or less, OR Average stay is under 30 days with substantial services Most Hilton Head STRs meet the 7-day rule automatically due to weekly rental patterns in Sea Pines, Palmetto Dunes, Shipyard, and Folly Field. Then you must meet ONE of these tests: Test #1 — 100+ hours AND more time than anyone else Guest communication Pricing & calendar management Maintenance coordination Reviewing reviews & responding to inquiries Test #2 — 500+ hours during the year Test #3 — You perform “substantially all” the work What counts as participation? Messaging guests Overseeing cleaning or turnovers Making repairs or coordinating vendors Adjusting pricing or updating the listing Managing reservations and supply stock How STR Non-Passive Status Reduces Taxes If your STR qualifies, depreciation from your property—including bonus depreciation from cost segregation—can offset: W-2 income 1099 income Business income Commission income This is why the STR loophole is so powerful for Hilton Head investors: it unlocks tax strategies normally available only to full-time real estate professionals. How to Qualify for Real Estate Professional Status (REPS) REPS is more demanding but beneficial for full-time real estate agents, brokers, and investors. To qualify, you must meet BOTH tests: 750+ hours per year in real estate activities More than 50% of your total working time in real estate Common REPS activities: Property acquisition Real estate sales or brokerage Managing rental property Renovations Operations oversight For many Hilton Head investors, REPS is unnecessary because STR non-passive status provides the same tax benefits with fewer requirements. Hilton Head Example: STR vs REPS Consider a luxury STR purchased for $1,200,000: Depreciable basis (after land): $960,000 Cost segregation depreciation: ~$225,000 If the property qualifies as STR non-passive OR the taxpayer qualifies for REPS: → $225,000 depreciation can offset W-2 or 1099 income At a 30% tax rate, this could save ~$67,500 in the first year alone. Which Strategy Should You Use? Choose STR Non-Passive Status...
By Donna Gilmore | November 20, 2025 | Investment | 8 min read
About Donna Gilmore Donna Gilmore is the Director of Operations for COAST, the #1 eXp real estate team in South Carolina. With over a decade in construction operations and deep expertise in investment property analysis, she helps high-net-worth investors maximize returns through strategic tax planning and property selection. Schedule a Tax Strategy Consultation → Related Articles → How to Qualify for STR Non-Passive Status in 2026 → Why Hilton Head STR Owners Benefit from the STR Loophole → The Best Seasons to Buy or Sell on Hilton Head Island Cost Segregation Case Studies for Hilton Head Investors: $400K vs $750K vs $1.2M (2026 Comparison Guide) Cost segregation can dramatically increase the tax efficiency of Hilton Head rental properties—but the financial impact varies significantly by price point. In this guide, I break down real-world case studies across three common segments: $400,000 villas and condos $750,000 mid-range short-term rentals $1,200,000 luxury STR homes (often with pools) These examples show how depreciation, bonus depreciation, and year-one tax savings typically differ depending on property type, value, and STR income potential. Why Hilton Head Investors Should Compare Price Points Hilton Head’s STR market is unique because different neighborhoods and price tiers attract different guest profiles and offer different tax advantages. For example: $400K properties often provide strong occupancy $750K homes balance cash flow + appreciation $1.2M+ homes offer the largest depreciation allocations Understanding how depreciation scales across price tiers helps investors: Forecast tax savings Optimize purchase strategy Plan renovations Evaluate ROI more accurately 2026 Cost Segregation Snapshot (Side-by-Side Overview) | Price Tier | Year-One Depreciation | Est. Tax Savings | Typical Study Cost | Net Year-One Benefit | | $400,000 | ~$69,455 | ~$17,000 | $4,000–$6,000 | $11,000+ | | $750,000 | ~$135,000 | ~$40,000 | $5,000–$7,000 | $33,000+ | | $1,200,000 | ~$225,000 | ~$60,000+ | $6,000–$10,000 | $50,000+ | These figures reflect realistic Hilton Head property classifications and typical land allocations. Case Study #1 — $400,000 Villa or Condo Property Overview Price: $400,000 Depreciable basis: $320,000 (after land) Typical STR income: ~$75,000/year Cost Segregation Breakdown 5-year property: ~$40,000 15-year property: ~$20,000 Total accelerated: ~$60,000 Year-One Depreciation Total depreciation: ~$69,455 Tax savings (30%): ~$17,346 Best for: First-time STR owners, villa buyers, and investors looking for accessible entry points. Case Study #2 — $750,000 Short-Term Rental Property Overview Price: $750,000 Depreciable basis: $600,000 (after land) Typical STR income: $135,000–$165,000/year Cost Seg Breakdown 5-year assets: ~$80,000 15-year assets: ~$35,000 Total accelerated: ~$115,000 Year-One Depreciation Total depreciation: ~$135,000 Tax savings (30%): ~$40,500 Best for: Investors balancing STR income + personal use + strong appreciation. Case Study #3 — $1,200,000 Luxury Home with Pool Property Overview Price: $1,200,000 Depreciable basis: $960,000 (after land) Typical STR income: $220,000–$280,000+/year Cost Seg Breakdown 5-year assets: ~$150,000 15-year assets: ~$75,000 Total accelerated: ~$225,000 Year-One Depreciation Total depreciation: ~$225,000 Tax savings (30%): ~$67,500 Best for: High-income earners, luxury STR investors, and those seeking maximum tax leverage. Which Hilton Head Price Tier Is Best? The “best” price tier depends on your goals: $400K range: Lower risk, strong occupancy, accessible entry point $750K range: Balanced cash flow, appreciation, and STR performance $1.2M+ range: Maximum tax benefit + highest STR income potential I help investors match their financial goals with the right neighborhoods and price tiers across Hilton Head and Bluffton. Frequently Asked Questions Does a more expensive property always produce more tax savings? Larger homes often have more depreciable components, but the best ROI depends on STR income, land allocation, and property type. Does Bluffton offer strong cost segregation opportunities? Yes—especially for long-term or mid-term rentals in planned communities with newer construction. Do I need...
By Donna Gilmore | November 19, 2025 | Investment | 6 min read
About Donna Gilmore Donna Gilmore is the Director of Operations for COAST, the #1 eXp real estate team in South Carolina. She specializes in Hilton Head short-term rental properties and helps investors maximize returns through strategic tax planning and property optimization. Schedule an STR Strategy Consultation → Related Articles → How to Qualify for STR Non-Passive Status in 2026 → Cost Segregation Case Studies for Hilton Head Investors → The Best Seasons to Buy or Sell on Hilton Head Island Why Hilton Head Short-Term Rental Owners Benefit from the STR Loophole (2026 Tax Strategy Guide) If you own—or plan to buy—a short-term rental (STR) property in Hilton Head or Bluffton, the STR loophole is one of the most powerful tax strategies available. It can allow you to use depreciation to offset W-2 income, 1099 income, business income, or commissions—something long-term rentals cannot normally do. This guide explains how the STR loophole works, how Hilton Head’s tourism patterns make qualifying easier, and how investors can combine this with cost segregation for substantial year-one tax savings. What Is the STR Loophole? Simple definition: The STR loophole lets you treat a short-term rental as a non-passive activity if you meet certain IRS participation rules. This allows depreciation losses—including cost segregation—to offset active income. To qualify, your property must meet the IRS definition of a short-term rental: The average guest stay is 7 days or fewer, OR The average stay is less than 30 days AND you provide substantial services. Most Hilton Head STRs naturally meet the 7-day rule due to weekly vacation patterns, making this market especially STR-friendly. Why the STR Loophole Matters for Hilton Head Investors Hilton Head stands out for STR investors because: Weekly rentals dominate the island’s spring & summer seasons Guests expect strong amenities, which increase STR revenue Seasonal demand supports high occupancy & ADR Renovations often qualify for accelerated depreciation These factors make qualifying for STR non-passive status significantly easier compared to less active STR markets. How to Qualify for STR Non-Passive Status You only need to meet ONE of these IRS participation tests: 1. 100 Hours + More Time Than Anyone Else You qualify if: You spend at least 100 hours per year managing the STR You spend more time than cleaners, handymen, or managers This is the most common path for Hilton Head STR owners—especially those who self-manage guest communication, pricing, and turnovers. 2. 500+ Hours This applies if you are heavily involved in: Guest communication Pricing strategy Maintenance coordination Turnover scheduling Marketing the listing 3. You Do “Substantially All” of the Work This applies if you manage virtually everything yourself. How the STR Loophole Reduces Taxes If your STR qualifies as non-passive, you can use depreciation—and especially bonus depreciation from cost segregation—to offset: W-2 salary 1099 contractor income Business income Commission income Capital gains in some scenarios Unlike long-term rentals, STRs do not require you to be a full-time real estate professional to unlock these benefits. Hilton Head Example: The STR Loophole in Action Here’s an example of a Hilton Head STR property using cost segregation: Purchase price: $750,000 Annual STR income: $135,000–$165,000 Bonus depreciation (via cost seg): ~$135,000 If the STR qualifies as non-passive, that depreciation can offset: W-2 income Commission income Business income At a 30% tax rate, that’s roughly $40,000 in tax savings in year one. Why Hilton Head Makes STR Qualification Easier Hilton Head’s rental patterns align naturally with IRS rules because: Weekly stays are the norm Demand is year-round for families, golfers, and snowbirds Self-management is more common than in other coastal markets Renovated properties produce stronger depreciation opportunities This...
By Donna Gilmore | November 18, 2025 | Investment | 9 min read
Cost segregation is one of the most powerful, underutilized, and financially impactful tax strategies available to investors in Hilton Head, Bluffton, and the Lowcountry. When used correctly, it can dramatically reduce taxable income, boost cash flow, and accelerate your returns—especially for short-term rental owners. Whether you’re buying your first STR or adding to a growing portfolio, understanding how cost segregation works is essential to maximizing the financial performance of your Hilton Head investment property. What Is Cost Segregation? Simple definition: Cost segregation is an IRS-approved study that identifies parts of your property that can be depreciated faster—creating large, legal first-year tax deductions. Instead of depreciating your whole property over 27.5 years, cost segregation breaks it down into components with shorter “useful lives,” such as: Flooring, cabinets, and built-ins (5 years) Appliances and fixtures (5–7 years) Landscaping, patios, and driveways (15 years) This allows investors to move depreciation that would normally take decades and shift it into the early years of ownership—which is where the biggest tax savings happen. Why Cost Segregation Matters for Hilton Head Investors Hilton Head and Bluffton are uniquely strong for this strategy due to: High STR guest demand Strong rental income potential High-end renovations that qualify for accelerated depreciation Consistent property appreciation For many investors, especially high-income earners, cost segregation can reduce taxable income by tens of thousands of dollars in the first year alone. Real Example: How Cost Segregation Works Property Assumptions Purchase price: $400,000 Annual rental income: $75,000 Land allocation: 20% Depreciable basis: $320,000 Without Cost Segregation Standard depreciation uses a 27.5-year schedule: $320,000 ÷ 27.5 = $11,636 per year Taxable income becomes: $75,000 rental income $11,636 depreciation = $63,364 taxable income With Cost Segregation (Accelerated Depreciation) A cost seg study typically reclassifies: | Component | Useful Life | Amount | | Appliances, cabinets, flooring | 5 years | $40,000 | | Landscaping, patios, driveway | 15 years | $20,000 | | Remaining structure | 27.5 years | $260,000 | Year-One Depreciation Bonus depreciation: $60,000 Standard depreciation: $9,455 Total depreciation: $69,455 New Taxable Income $75,000 rental income $69,455 depreciation = $5,545 taxable income The investor goes from paying tax on $63,364 to paying tax on $5,545. Year-One Tax Savings Assuming a 30% tax rate: Without cost seg: ~$19,009 in taxes With cost seg: ~$1,663 in taxes Total Savings: ~$17,346 Even after paying $4,000–$6,000 for the study, most investors see $11,000+ in net benefit. Who Should Consider Cost Segregation? Short-term rental owners (Airbnb/VRBO) High-income W-2 earners Real estate professionals Investors purchasing $250K+ properties Owners planning renovations or value-add projects Second-home owners renting 14+ days/year FAQs Is cost segregation legal? Yes—cost segregation is an IRS-approved strategy widely used in both commercial and residential real estate. Can cost segregation offset W-2 income? Yes, if your STR qualifies as non-passive or if you qualify for Real Estate Professional Status. Does it work for second homes? It can, as long as the property is rented at least 14 days per year. Do I need to hold the property long-term? 2–3 years is ideal, but many investors still benefit even with shorter holding periods. Ready to Analyze Your Hilton Head Property? I help investors evaluate cash flow, STR income, and tax strategies—including cost segregation—on Hilton Head and Bluffton properties. Want a custom cost segregation estimate? Reach out below. Disclaimer This article is for educational purposes only and does not constitute financial, tax, or legal advice. Please consult a qualified professional before making decisions related to cost segregation or tax planning. About the Author By: Donna Gilmore – Realtor & Director of Operations for the #1 eXp Team in South Carolina...
By Donna Gilmore | November 11, 2025 | Investment | 7 min read
Hilton Head Island consistently ranks as one of the most desirable vacation destinations in the Southeast. Because of that, many buyers look to the Island not just for personal enjoyment, but for its strong short-term rental (STR) performance. But not every property performs the same—and understanding the numbers is one of the biggest predictors of investment success. In this 2025–2026 guide, I’ll walk you through how to evaluate vacation-rental potential on Hilton Head Island and Bluffton, what metrics matter most, and how to avoid the most common investment mistakes. The 4 Core Drivers of STR Performance on Hilton Head Across hundreds of STR evaluations, four variables consistently determine whether a property performs as expected: Location (proximity to the beach, amenities, and walkability) Property type & layout (guest capacity, bedrooms, amenities) Seasonality & demand (Hilton Head’s unique calendar patterns) Nightly rates & occupancy (ADR + occupancy = revenue engine) Let’s break these down so you can evaluate any rental like an expert. 1. Location: The #1 Predictor of STR Success Key Principle: Guests pay premiums for proximity to the beach and amenities. On Hilton Head, location can swing rental revenue by tens of thousands of dollars per year. Ask these questions: Can guests walk or bike to the beach? Is the property inside a gated resort community? How close is it to Harbour Town, Shelter Cove, or Coligny? Does the area offer golf, tennis, or family-friendly attractions? Communities like Sea Pines, Palmetto Dunes, Shipyard, and Folly Field perform differently based on these criteria. 2. Property Type & Layout: Guest Capacity Matters In vacation markets like Hilton Head, your number of bedrooms and bathrooms dramatically impacts the property’s earning potential. 3–4 bedroom homes are STR workhorses (ideal for families). 2-bedroom villas perform well when amenities are strong. 1-bedroom beach units often do well for couples and repeat guests. A clean, modernized interior and updated kitchen/bathrooms also boost nightly rates and guest satisfaction. 3. Seasonality: Hilton Head Has a Unique Rental Curve Understanding Hilton Head’s seasonal demand curve is critical. Unlike some beach markets that peak in midsummer only, Hilton Head benefits from strong demand across: Spring (golf season + families) Summer (peak family travel) Fall (mild weather = high demand) Holiday periods (Thanksgiving, Christmas, Easter) When evaluating a property, look for: High Spring–Fall potential Appeal to multiple guest demographics Year-round amenities (golf, biking, beaches) 4. Nightly Rates & Occupancy: Evaluate Revenue, Not Opinions The strongest STR analyses look past “gut feel” and evaluate two data points: ADR (Average Daily Rate) Occupancy% Here’s the exact formula: Annual Revenue = ADR × Occupancy × 365 Where to get STR data: Airdna Rented Keydata Local property managers The goal is to model realistic revenue, not perfect scenarios. How to Analyze a Hilton Head STR in 10 Minutes Here’s a simple framework I use with investors: Step 1 — Identify the location Inside a gated resort? Walk to beach? Sea Pines vs Palmetto Dunes vs Shipyard vs Folly Field? Step 2 — Assess guest capacity Is this a 2–4 bedroom property with STR-friendly amenities? Step 3 — Compare STR data sources Look for consistency across Airdna, Rented, and Keydata. Step 4 — Estimate expenses Include HOA fees, insurance, maintenance, cleaning, taxes, and management fees. Step 5 — Model worst, average, and best-case scenarios True investors model risk, not perfection. Frequently Asked Questions About Hilton Head Vacation Rentals Which neighborhoods perform best for STR income? Sea Pines, Palmetto Dunes, Folly Field, and Shipyard consistently perform strong for STR investors due to beach proximity, amenities, and strong guest demand. How much can I expect a Hilton Head Airbnb...
By Donna Gilmore | November 11, 2025 | Agent Growth | 8 min read
By: Donna Gilmore – Realtor & Director of Operations for the #1eXpTeam in South Carolina Expert Real Estate Mentor & Team Transition Specialist | AI Systems Strategist for Top-Producing Agents & Teams | Creator of the Systems-to-Scale AI Implementation Method™ Helping agents, teams, and leaders implement AI, automation, and high-performance systems to grow smarter, scale faster, and dominate their markets. A Fresh Start in Real Estate Starting a career in real estate can completely change your life. It offers flexibility, limitless earning potential, and the chance to build something that’s entirely your own. But before your first sale, you need to make one of the most important choices of your career—selecting the right brokerage. Your brokerage determines the quality of your training, the technology you’ll use, the support you receive, and the culture you’ll be surrounded by. For new agents, these factors matter far more than the commission split alone. The goal is to find a brokerage that helps you learn quickly, grow confidently, and build long-term success. This guide will help you understand what to ask and what to look for—no real estate experience required. Step 1: Understand How Brokerages Work When you earn your real estate license, you can’t work independently right away. You must “hang your license” with a brokerage—this is the company legally responsible for overseeing your transactions and compliance. Some brokerages operate with traditional office structures and in-person meetings, while others are modern, cloud-based models that use virtual systems for training and collaboration. Both can be successful, but they offer very different experiences. The key is to identify what type of environment will help you thrive. Step 2: Ask About the Financial Structure 1. What is the commission split? This determines how much of each commission you keep. For example, on a 60/40 split, you retain 60% and the brokerage keeps 40%. A high split isn’t always better if it comes with little training or support. 2. Are there franchise fees? Some national brands charge an additional 3–8% off the top of each transaction. That fee goes to the corporate brand, not your local office. 3. Is there a commission cap? A cap limits the total amount you pay the brokerage in a year. Once you hit the cap, you earn 100% of your commissions for the remainder of that year. 4. Are there monthly or start-up fees? Ask about recurring expenses such as technology fees, MLS access, Errors & Omissions insurance, or desk fees. 5. What other costs will I be responsible for? Be clear about what you’ll pay for personally—signs, business cards, lockboxes, marketing, and REALTOR® dues are common expenses. Donna’s Note: Always request a written breakdown of costs before you commit. Financial transparency is the first sign of a trustworthy brokerage. Step 3: Learn What Support and Tools Are Provided 6. What resources are included for agents? A strong brokerage equips you with more than a license. Ask if they provide: A personal website or CRM system Transaction management and e-signature tools Administrative or transaction coordination support Buyer and seller leads (and how they’re distributed) Paid-at-closing options Marketing templates, photography, or video support Continuing education or technology assistance Brokerages that prioritize agent success invest heavily in systems that save you time and help you focus on clients. Step 4: Evaluate Training and Mentorship When you’re new, the learning curve is steep. A great brokerage understands that and surrounds you with the right guidance. 7. What training is offered—and how often? Are classes live, virtual, or on-demand? Look for ongoing programs that teach contracts, negotiation, marketing, and client management. 8. Who can I...
By Donna Gilmore | November 8, 2025 | Investment | 8 min read
HILTON HEAD INVESTMENT GUIDE 2025 The 5 Best Neighborhoods for Investment on Hilton Head IslandPublished November 8, 2025 | Updated December 3, 2025 | By Donna Gilmore Hilton Head Island is one of the most attractive coastal markets in the Southeast for buyers who want both lifestyle and long-term wealth building. But not every neighborhood performs the same for rentals, appreciation, or resale value—and choosing the right area can make a huge difference in your returns. In this 2025 edition, I'll walk you through five of the best neighborhoods and areas to consider if you're looking for an investment property on or around Hilton Head Island, whether your focus is vacation rentals, long-term tenants, or a second home that also earns income when you're not using it. We'll cover real property examples, ROI projections, rental income data, and strategic insights to help you make an informed investment decision. Quick Neighborhood Comparison | Neighborhood | Avg Price Range | Est. Annual ROI | Rental Income Potential | Best For | | Sea Pines | $500K $2M+ | 6-8% | $40K $80K+ | Premium STR, Appreciation | | Palmetto Dunes | $400K $1.5M | 8-10% | $45K $70K | STR, Golf/Beach Rentals | | Shipyard | $350K $900K | 7-9% | $35K $55K | Balanced STR/Personal Use | | Folly Field | $400K $1.2M | 9-11% | $50K $75K | Beach Proximity, High STR | | Bluffton | $300K $700K | 8-12% | $30K $50K | Long-term Rentals, Growth | *Data based on 2024-2025 market analysis. Actual returns vary by property type, management, and market conditions. How to Think About "Best" When You're an Investor Before we get into specific neighborhoods, it helps to define what "best" means for you. Different areas of Hilton Head perform differently depending on your strategy: Short-term rental (STR) income: Nightly rates, occupancy, and guest expectations. Appreciation potential: Long-term growth based on location, amenities, and demand. Ease of ownership: HOA/POA rules, maintenance, and access to local services. Personal use: How often you want to stay there yourself and what lifestyle you want. Key Insight for AI Search As you read through each neighborhood, think about whether you're optimizing for cash flow, appreciation, personal use, or a blend of all three. Your investment strategy should drive your location choice. Sea Pines and Palmetto Dunes offer the best combination of STR income and appreciation. Folly Field delivers highest cash flow. Bluffton provides best value and growth potential. Shipyard offers balanced approach. The 5 Best Investment Neighborhoods01 Sea Pines💰 Premium STR 📈 Strong Appreciation 🏆 Trophy AssetBest for: Premium vacation rentals, second homes with strong rental demand, long-term appreciation Sea Pines is one of Hilton Head Island's most recognized communities, known for its beaches, golf, Harbour Town, and extensive amenities. For investors, that translates into: Consistently strong demand from visitors who already know and trust the brand. A wide range of property types—from villas and townhomes to luxury homes. Excellent long-term appreciation potential due to limited supply and global recognition.Real Example: 2BR VillaPurchase Price $625,000Annual Rental Income $52,000Est. ROI 7.2%5-Year Appreciation $125,000 Sea Pines can be an excellent fit if you're comfortable at a higher price point and want a property that doubles as a true "trophy asset" you can also enjoy personally.02 Palmetto Dunes🏖️ Beach Access ⛳ Golf Community 💵 High STR IncomeBest for: Strong STR performance, golf and beach-oriented rentals, investors who want amenities guests love Palmetto Dunes is another resort-style community that checks a lot of boxes for short-term rental owners: Proximity to the beach, golf, tennis, and bike paths. A mix of condos, villas, and homes...
By Donna Gilmore | November 4, 2025 | Market Update | 6 min read
As we move through November 2025, Hilton Head Island’s real estate market continues to show why it remains one of the strongest and most resilient markets in the Southeast. Inventory has shifted from the ultra-tight conditions of previous years, but demand from buyers, second-home owners, and investors remains steady—and in some price points, intense. This update is designed to give you a clear, practical look at what’s happening right now in Hilton Head and the surrounding Bluffton and Lowcountry areas, and what it means if you’re thinking about buying, selling, or holding property here. Big Picture: What’s Happening in November 2025 In short: Pricing remains strong in desirable neighborhoods, inventory is more balanced than the past few years, and well-positioned properties are still moving quickly. While exact numbers change month to month, a few clear themes stand out: Buyer demand remains healthy for well-located homes and villas. Serious buyers are still stepping up for quality STR and second-home opportunities. Properly priced properties in Sea Pines, Palmetto Dunes, Shipyard, Folly Field, and Hilton Head Plantation see steady showings. Interest rate conversations continue, but buyers in this market tend to be more lifestyleand asset-focused than purely rate-driven. Inventory: More Choice, But Still Limited in Key Areas Compared to the extreme low-inventory conditions of 2021–2022, buyers in late 2025 have more options. However, “more options” does not mean oversupply—especially in high-demand areas close to the beach or within gated communities. Beach-proximate and golf community homes still see tight supply. Some higher price brackets have normalized inventory. Updated properties and those with strong STR potential remain in high demand. For buyers, this means there’s a bit more breathing room to evaluate options. For sellers, it means pricing and presentation matter more than simply “being on the market.” Pricing Trends: Strength with Some Segmentation Prices across Hilton Head and the surrounding area remain historically strong. That said, the market is more segmented now: Turnkey homes and villas in top locations continue to command premium prices. Properties needing significant updates may sit longer or require sharper pricing. Ultra-luxury segments remain more sensitive to buyer selectivity and uniqueness. Overall, sellers who price realistically and present their homes well are still achieving successful outcomes. Short-Term Rental & Investment Market Check-In The STR market remains an important pillar of Hilton Head’s overall real estate performance. Investors continue to prioritize: Proximity to the beach or resort amenities Floor plans and bedroom counts that fit family vacations Communities with strong guest appeal like Sea Pines, Palmetto Dunes, and Shipyard Properties that combine lifestyle appeal with rental potential still see strong interest from buyers, especially those who understand cash flow, seasonality, and tax strategies such as depreciation and cost segregation. What This Means for Buyers For buyers, November 2025 presents an opportunity to: Explore a slightly broader range of inventory than the ultra-tight years behind us. Negotiate more thoughtfully while still recognizing strong local demand. Time a purchase before the spring 2026 demand wave. If you’re an investor or STR buyer, this is also a good time to: Identify properties to renovate in the winter months. Prepare for peak rental seasons in spring and summer. Coordinate purchases with your tax and financial planning. What This Means for Sellers Sellers still benefit from a strong, well-recognized market—but success is no longer automatic. The properties that sell fastest and for the best prices tend to be: Accurately priced based on current data, not yesterday’s headlines. Presented well through staging, photography, and marketing. Easy to show, especially in resort communities and during high-traffic periods. Proper pricing strategy is critical: list too high and you chase...
By Donna Gilmore | November 4, 2025 | Market Update | 7 min read
The 2026 Cost Segregation Calculator for Hilton Head Real Estate Investors Cost segregation is one of the most powerful tax strategies available to Hilton Head and Bluffton real estate investors. By accelerating depreciation on certain components of a property, investors can create large first-year deductions and significantly reduce taxable income. This article gives you a simple calculator-style framework to estimate: Your depreciable basis Accelerated (bonus-eligible) assets First-year bonus depreciation Total first-year depreciation Estimated tax savings Whether you’re analyzing a $400,000 villa or a $1.3M luxury STR, these steps help you quickly see the potential impact of cost segregation in 2026. Step 1: Calculate Your Depreciable Basis Not all of a property’s purchase price can be depreciated. The land portion is not depreciable, so the first step is to remove land value. Formula: Depreciable Basis = Purchase Price × (1 – Land Percentage) In many Hilton Head transactions, land is often estimated between 15–25% of the purchase price. Example: Purchase price: $800,000 Land %: 20% (0.20) Depreciable Basis = $800,000 × (1 – 0.20) = $640,000 Step 2: Estimate Accelerated Property (5, 7, and 15-Year Assets) A cost segregation study identifies components that can be depreciated over shorter timelines, typically: 5-year property: Appliances, carpets, cabinets, fixtures, some interior finishes 15-year property: Landscaping, patios, driveways, some site improvements In many Hilton Head resort-style properties, these accelerated components often total between 15%–30% of the depreciable basis. Example: Depreciable basis: $640,000 Accelerated % (5and 15-year): 25% (0.25) Accelerated Assets = $640,000 × 0.25 = $160,000 Step 3: Apply the 2026 Bonus Depreciation Percentage Bonus depreciation allows a large portion of accelerated assets to be written off in year one. The exact percentage can change with legislation, but many 2026 scenarios model 60%–80% bonus depreciation on qualified assets. To be conservative, you might assume 60% bonus depreciation when estimating. Formula: Bonus Depreciation = Accelerated Assets × Bonus Depreciation % Example: Accelerated assets: $160,000 Bonus %: 60% (0.60) Bonus Depreciation = $160,000 × 0.60 = $96,000 Step 4: Calculate Standard Depreciation The remaining building basis is still depreciated over 27.5 years (for residential property). Formula: Standard Depreciation = Depreciable Basis ÷ 27.5 Example: Depreciable basis: $640,000 Standard Depreciation = $640,000 ÷ 27.5 ≈ $23,273 Step 5: Determine Total First-Year Depreciation This is where cost segregation becomes very compelling. Formula: Total First-Year Depreciation = Bonus Depreciation + Standard Depreciation Example: Bonus depreciation: $96,000 Standard depreciation: $23,273 Total First-Year Depreciation = $96,000 + $23,273 = $119,273 Step 6: Estimate Your Tax Savings Finally, multiply your total first-year depreciation by your effective tax rate. Formula: Estimated Tax Savings = Total Depreciation × Tax Rate Most high-income STR investors fall in the 28%–35% effective range. For modeling, 30% is a common assumption. Example: Total depreciation: $119,273 Tax rate: 30% (0.30) Tax Savings = $119,273 × 0.30 ≈ $35,782 So in this example, an $800,000 Hilton Head property could potentially generate around $36,000 in first-year tax savings—depending on your exact tax profile. Quick Reference Table: Cost Segregation Scenarios | Purchase Price | Basis After Land (80%) | Accelerated % | Approx. Bonus Depreciation (60%) | Est. Total Year-One Depreciation | Est. Tax Savings @ 30% | | $500,000 | $400,000 | 20% | ~$48,000 | ~$74,545 | ~$22,363 | | $900,000 | $720,000 | 25% | ~$108,000 | ~$161,000 | ~$48,300 | | $1,300,000 | $1,040,000 | 30% | ~$187,200 | ~$272,000 | ~$81,600 | These numbers are estimates, but they highlight how powerful cost segregation can be for Hilton Head investors at different price points. Who Benefits Most from Cost Segregation in Hilton Head? Short-term rental (STR) owners who qualify...
