▾The Residence
Newly built in 2025, 34 Tupelo offers what Sea Pines rarely does — a turnkey, current-design residence in Hilton Head Island's original gated community. Set along the fairways of Heron Point Golf Course, seven bedrooms and beautifully curated spaces frame sweeping golf-course and pool views across soaring, light-filled interiors that open through multiple decks and porches to a private pool below. Designed for gracious living, gathering, and effortless Lowcountry style, the home offers both scale and intimacy.
Highlights
The value
At this level, value rests less on square-foot comparison than on what can't be reproduced — new construction completed in 2025 in Sea Pines. Offerings of this kind are genuinely limited, which is what sustains their position in the market.
Floor Plans
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Gallery
Exterior & Grounds
The Living Spaces
Bedrooms & Baths
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The Setting
Sea Pines is Hilton Head Island's original and most prestigious resort community — and the benchmark every other neighborhood on the island is measured against. Set on 5,200 securely gated acres at the island's south end, it pairs Atlantic beachfront and Calibogue Sound with championship golf, Harbour Town, and a private beach club.
Distance & access
Community amenities
Realtor · eXp ICON Agent, Co-Founder, COAST
Co-founder of COAST, Brokered by eXp Realty and one of Hilton Head Island's most trusted names in deepwater, oceanfront, and waterfront luxury homes. An eXp ICON agent serving Hilton Head, Bluffton, and the Lowcountry.
COAST · brokered by eXp Realty · eXp Luxury
COAST is an eXp Luxury member team, and qualifying luxury listings are marketed through eXp's international luxury program — not only to the local market. That reach spans eXp's global network of 80,000+ agents in around 30 countries, layered on top of COAST's own Hilton Head marketing engine (dedicated listing pages, cinematic media, and AI-era search visibility).
Questions
34 Tupelo Road is one of the few — a 2025 new build with seven bedrooms and seven full baths, a one-to-one count, plus multiple primary suites. Tristan can confirm the exact bath configuration room by room.
Yes — 34 Tupelo Road was completed in 2025 with multiple primary suites among its seven bedrooms and seven baths, so more than one guest can have a true suite. Soaring ceilings and an open-concept plan keep the gathering spaces scaled to a larger group.
Yes. Sea Pines permits short-term rentals, and the Town of Hilton Head Island layer applies on top: a short-term rental permit, a business license, tax collection and quarterly filings. Both layers must be cleared, and Tristan can confirm the current filing steps.
A finished 2025 build means code-current systems and no deferred maintenance, so it can be used or rented from the first season rather than renovated for two years. Ground-up luxury construction rarely surfaces inside the Sea Pines gates.
Sea Pines fits that brief — 5,200 gated acres with Harbour Town, three Resort courses, the Beach Club and South Beach Marina. 34 Tupelo Road answers the suite requirement directly: seven bedrooms, seven baths and multiple primary suites across 4,400 square feet.
New construction inside the gates is structurally scarce, so a 2025 home trades on condition and code-current systems rather than square footage alone. Island detached sellers have closed year-to-date at roughly 96% of list, so this pricing is being tested by the market.
Yes — you are paying for brand-new 2025 construction with a private pool along the Heron Point fairways, a profile with very few peers inside the gates. The island's $1M-plus segment is balanced right now, so there is room to compare before you commit.
Ownership carries a Sea Pines CSA assessment covering roads, gates, security and beach access. Golf, the Beach Club and the fitness center belong to The Sea Pines Resort, and Sea Pines Country Club is a separate member-owned club — each sets its own terms.
Sea Pines is among the island's most rental-oriented communities, and a seven-bedroom new build with a private pool sits in the part of the market that commands premium peak-season rates. Rental performance for comparable Sea Pines homes can be reviewed before you buy.
34 Tupelo Road is a 2025 completion offered at $3,875,000 — seven bedrooms, seven baths, 4,400 square feet, a private pool, and golf course views along Heron Point. Ground-up luxury builds inside the Sea Pines gates surface only rarely.
Sea Pines is widely considered Hilton Head Island's premier second-home community, offering gated security, deeded beach rights, a deep-water marina, championship golf, fitness facilities, and a full-service village within its 5,000-acre plantation. 34 Tupelo Road sits inside Sea Pines and delivers all of those amenities alongside a brand-new 2025 construction with a private pool, golf course and pool views, 7 bedrooms across 4,400 sq ft, and multiple primary suites. Contact Tristan O'Grady to arrange a private showing.
Carrying costs for a luxury home in Sea Pines typically include Beaufort County property taxes, Sea Pines Property Owners Association fees, and insurance premiums — windstorm and flood coverage are standard on the island and vary by proximity to water and construction type. For a newly built 2025 home at the $3,999,000 price point like 34 Tupelo Road, buyers benefit from modern construction standards that can reduce insurance underwriting risk compared to older inventory, though exact figures depend on coverage elections and financed vs. cash ownership. Tristan O'Grady at 843-301-3333 can provide current estimates specific to this property.
Client Reviews
“Tristan's knowledge and experience was invaluable. He guided every one of our vacation-rental properties to a successful close. I would highly recommend Tristan.”
Private inquiry
Request a private showing or more on 34 Tupelo Road. Tristan O'Grady will respond personally — in-person and live-video showings both available.