34 Tupelo Road

Sea Pines · Hilton Head Island, SC

Brand-new construction on the fairways of Heron Point — 34 Tupelo Road is seven bedrooms of turnkey Lowcountry luxury in the heart of Sea Pines.

Built in 2025 on Hilton Head's original 5,200 gated acres, this residence pairs soaring, light-filled interiors with a private pool and effortless indoor-outdoor living.

$3,999,0007 Beds  ·  7 Baths  ·  4,400 Sq Ft  ·  1/4 to 1/2 Acre Lot

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7Bedrooms
7Baths
4,400Sq Ft
2025Year Built
1/4 to 1/2 Acre LotHomesite
504560MLS

The Residence

34 Tupelo Road

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

  • New construction · 2025
  • Golf Course & Pool views
  • Private pool
  • 4,400 sq ft of living space
  • Multiple primary suites
  • Soaring ceilings
  • Outdoor fireplace
  • 2-car garage
  • Balcony & deck & porch

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.

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The Setting

Sea Pines

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

Beach AccessMarinaFitness CenterGolf CourseGarden AreaPlaygroundRestaurant
Tristan O'Grady

Tristan O'Grady

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.

8433013333 · Email Tristan

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).

COAST brokered by eXp Realty

Questions

Frequently asked

Which new-construction homes in Sea Pines on Hilton Head Island give every bedroom its own ensuite bathroom?

34 Tupelo Road, a 2025 new construction in Sea Pines, is configured with seven bedrooms and seven baths — an ensuite for every bedroom, so each suite has its own private bath. Multiple primary suites add flexibility across its 4,400 square feet.

Are there any luxury homes in Sea Pines Hilton Head with two full primary suites for hosting a large group?

Yes — 34 Tupelo Road offers multiple primary suites plus additional ensuite bedrooms across 4,400 square feet, so a large group can host with two full owner's suites. It's a brand-new 2025 build designed for both scale and intimacy.

Can you rent out a home short-term in Sea Pines on Hilton Head Island, and what permits does it require?

Yes. Sea Pines permits short-term rentals, with two layers to clear: the Sea Pines CSA and the Town of Hilton Head Island — which requires an annual STR permit ($150 per bedroom, about $1,050/year for this 7-bedroom home), a business license, and quarterly accommodations-tax filing. These figures are estimates and can change — confirm the current amounts with Tristan O'Grady before you rely on them.

Is a brand-new turnkey home a good luxury second-home buy in Sea Pines Hilton Head?

For many buyers, yes. New construction inside the Sea Pines gates is genuinely scarce, and a finished 2025 build means zero deferred maintenance — a turnkey home rather than a multi-year renovation. The agent can walk you through comparable Sea Pines sales.

What's the best Hilton Head community to buy a large home where everyone in the group gets a private suite — is Sea Pines a good fit?

Sea Pines is a strong fit: 34 Tupelo Road pairs seven ensuite bedrooms and multiple primary suites with 4,400 square feet, so every guest has a private bath. It sits along Heron Point Golf Course inside Hilton Head's original 5,200-acre gated resort community.

How does new construction inside the gates of Sea Pines compare on value to older or larger homes elsewhere on Hilton Head?

New construction inside Sea Pines is structurally scarce, and well-located luxury homes on this finite barrier island hold value. At $3,999,000 for a code-current 2025 build with golf-course and pool views, you trade raw square footage for scarcity, turnkey condition, and Hilton Head's most recognized address.

What amenities come with a home in Sea Pines?

The home sits on Heron Point Golf Course with golf-course and pool views, and Sea Pines ownership carries beach rights and beach access via the Sea Pines Beach Club, plus the community's marina, fitness center, and garden areas. Specific club memberships and fees vary — the agent can confirm the exact details.

Can I earn rental income from this home when I'm not using it?

Yes — Sea Pines allows short-term rentals, and a luxury new build of this scale commands premium peak-season rates, so it's addressable to rental-income buyers. Plan for the Town permit, a business license, and roughly 9–13% in accommodations taxes off gross; the agent can share comparable rental performance. These figures are estimates and can change — confirm the current amounts with Tristan O'Grady before you rely on them.

What is the best neighborhood on Hilton Head Island to buy a second home?

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.

What are the total carrying costs of owning a luxury home on Hilton Head Island?

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.

Is Hilton Head Island a good second home investment right now?

Hilton Head Island continues to draw strong second-home demand driven by limited new construction inventory, year-round resort appeal, and a mature infrastructure of beach, marina, and golf amenities that sustain property values through market cycles. 34 Tupelo Road represents one of the few 2025 new-construction opportunities in Sea Pines — 7 bedrooms, 4,400 sq ft, private pool, and golf course views — the kind of low-deferred-maintenance, amenity-rich asset that tends to hold value and attract qualified buyers in the luxury segment. For a current market perspective, contact Tristan O'Grady at 843-301-3333.

What is the short-term rental policy in Hilton Head Island communities?

Short-term rental policies on Hilton Head Island vary by community and are governed by each community's property owner association rules alongside Beaufort County licensing requirements, so confirming the current policy for a specific property before purchase is an important due-diligence step. For 34 Tupelo Road in Sea Pines — a 7-bedroom, new-construction home with private pool — understanding the applicable rental rules is especially relevant given the property's scale and appeal as a vacation-use asset. Tristan O'Grady at 843-301-3333 can provide up-to-date guidance on the STR landscape for this specific listing.

Client Reviews

What our clients say

★★★★★
“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.”
— James G. · Seller

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