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$1,985,000
3 Beds ⋅ 4 Baths ⋅ 2,722 SqFt. ⋅ HILTONHEAD-511813 MLS
An absolute standout in Sea Pines. This exceptional home was worth the wait... but is not expected to last long! Relaxed and comfortable meets modern and sophisticated. Prepare to be captivated by this exceptionally cool, single-level stunner! A private (gated) front courtyard enhances the arrival experience, while the private backyard setting is unmatched. Inside you will find an open-concept interior that is complimented by numerous design enhancements. The design-forward, chef-style kitchen will reignite your love of both cooking and entertaining, boasting quartz counters, impressive cabinetry, designer lighting, updated appliances, gas cooking, beverage refrigerator, pantry, and an expansive flat-top island. The home naturally flows out to an inviting screened porch, extending comfortable living space outdoors. The spacious owner's suite enjoys tranquil water views and a spa-like bath, while the two private guest rooms offer beautifully remodeled en-suite baths as well. Embrace a year-round outside lifestyle with a refreshing (heated) saltwater pool, firepit area, peaceful lagoon and private backyard lawn. The property features a durable TPO roofing system, valued for its energy efficiency, longevity, and low-maintenance performance. Set on nearly a half-acre with open space on two sides, this high-elevation property stands apart! Ideally positioned in Sea Pines on a quiet street almost directly between the Sea Pines Beach Club and the Harbourtown Yacht Basin! Tastefully furnished for immediate gratification!

41 Willow Oak W Road, Hilton Head Island

Listing courtesy of Collins Group Realty. Selling Office: Keller Williams Realty.

$2,750,010
4 Beds ⋅ 5 Baths ⋅ 3,216 SqFt. ⋅ HILTONHEAD-504056 MLS
Welcome to 2 Willow Oak Road West, an extraordinary and masterfully renovated residence located in the heart of Sea Pines on Hilton Head Island. Thoughtfully redesigned with impeccable attention to detail, this stunning home now offers 4 bedrooms, 4.5 bathrooms, and a seamless blend of modern luxury and Lowcountry sophistication. Every inch of the home has been transformed, featuring top-of-the-line appliances, including a Fulgor Milano Fridge/Freezer ($25,000 value), Perlick Wine Fridge, a brand new Jen Air Gas range/stove with downdraft, new stainless steel microwave, and two Dishwashers for ultimate convenience, PLUS 2-brand new hot water heaters, and brand new roof. An additional bedroom and bathroom were added to enhance both functionality and comfort, creating ideal accommodations for family and guests alike. The open-concept living spaces flow effortlessly to the outdoors, where a brand-new wraparound and extended Trex deck provides the perfect setting for entertaining or relaxing while enjoying breathtaking views of the 16th hole of the Heron Point Golf Course. Situated on a private 1.09 acre lot, the property offers a rare level of privacy and space. The resort-style backyard features a brand new in-ground pool and hot tub, completing this exceptional outdoor oasis. Located within the world-renowned Sea Pines Resort, residents enjoy access to 3 championship golf courses with flexible access, pristine beaches, marina, dining, and endless amenities. Ideally situated in the heart of the community, you're just minutes from Harbour Town, the Sea Pines Beach Club, Lawton Stables, the Forest Preserve, and the miles of scenic bike trails that connect it all. This is a truly exceptional opportunity to own a move-in-ready luxury home in an unparalleled setting.

2 Willow Oak W Road, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

$2,575,000
4 Beds ⋅ 4 Baths ⋅ 3,400 SqFt. ⋅ HILTONHEAD-506349 MLS
Gorgeous! Just gorgeous! Extensively renovated in 2022, this beautifully reimagined, single-level, Sea Pines residence blends refined design with exceptional privacy on an oversized (1/2 acre+) property. Relax and recharge and take a refreshing dip in the private pool with scenic golf views beyond, while the cart path on the other side of the fairway adds to the privacy. The open, light-filled interior features hardwood flooring, smooth ceilings with vaulted areas, plantation shutters, and current finishes throughout. A designer chef-inspired kitchen showcases an oversized quartz island, upgraded stainless appliances, recessed LED lighting, and picturesque views from abundant windows and glass. Four (well-positioned) bedrooms, including a large bunk-style room for the youngies, a double garage, AND a new roof in 2022. Note that the leisure trail at the end of the street connects to Plantation Club and the Beach Club!

7 Red Maple Road, Hilton Head Island

Listing courtesy of Collins Group Realty. Selling Office: Harbour & Home Real Estate.

$1,550,000
3 Beds ⋅ 4 Baths ⋅ 3,285 SqFt. ⋅ HILTONHEAD-452520 MLS
Set on a lush 3/4-acre lot overlooking the 17th tee of Heron Point, this 3,285 SqFt Sea Pines home blends thoughtful updates with untapped potential. Enjoy a newer roof, HVAC, PEX plumbing, all new ductwork, and a refreshed kitchen. The heated saltwater pool and new circular drive add to the home's charm and curb appeal. Bathrooms and the primary suite offer a chance to add your personal touch. With space, privacy, and a strong framework, this home is perfect for a buyer with vision looking to create something special in one of Hilton Head's most desirable communities. Great proximity to Harbour Town and the Beach Club! Short-term rentals allowed. Seller offering a $20k buyer credit with an acceptable offer, providing flexibility for updates, aesthetic enhancements, or closing costs. A rare opportunity to tailor a Sea Pines property to your individual vision.

2 Red Maple Rd, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry. Selling Office: Sea Pines Real Estate - Beach Club.

$1,500,000
3 Beds ⋅ 4 Baths ⋅ 3,216 SqFt. ⋅ HILTONHEAD-451940 MLS
Nestled on a one-acre lot in the heart of Sea Pines, this home offers privacy and prime location. Mature trees and lush landscaping surround this spacious corner lot, w/ a wrap around driveway backing up to golf course views. Inside, the split-level floor plan offers multiple living and entertaining areas. The private primary wing features two full baths, while the guest wing includes two additional bedrooms & shared bath. With generous indoor and outdoor spaces, this home is ideal for primary or rental property. A rare opportunity to own over an acre on one of Sea Pines’ most sought-after streets—don’t miss the chance to make it yours!

2 Willow Oak W Road, Hilton Head Island

Listing courtesy of Engel & Volkers. Selling Office: Century 21 Integra.

$1,750,000
5 Beds ⋅ 4 Baths ⋅ 3,434 SqFt. ⋅ HILTONHEAD-450975 MLS
Best 5 Bedroom Home in Sea Pines under $2M! Great Location between Harbourtown and the Beach Club! Open kitchen to dining and living space. Very private pool backs up to nature preserve! Easy access to beaches, golf courses, pickleball, tennis, shopping & dining. Kick your shoes off in the family room, lounge in the big living room or step outside to enjoy the large private pool with covered lanai. This home offers big living areas and quiet back yard. Whether you're planning to rent or create lasting family memories, you will love Sea Pines Living at 25 W. Willow Oak! New Roof(2021), Appliances 2018 & HVAC systems(2024 and 2022).

25 Willow Oak W Road, Hilton Head Island

Listing courtesy of Hilton Head Properties. Selling Office: Keller Williams Realty.

$2,800,000
3 Beds ⋅ 3 Baths ⋅ 3,677 SqFt. ⋅ HILTONHEAD-450896 MLS
For the discerning buyer seeking the ultimate ocean-oriented home, this is the one. Impeccably designed single-story home offers unparalleled attention to detail & exceptional quality. Features 3 BR, 3 BA, & flex room, perfect for any lifestyle. Outdoors, you'll find a stunning pool with ample space, a spa, and soothing waterfalls. The covered lanai, complete with a fireplace & retractable screens, an ideal space for year-round entertaining.This extraordinary property represents the best of Sea Pines living! Shows like a model—truly a must-see to fully appreciate the craftsmanship that photos can't capture. Furniture is negotiable.

8 Red Maple Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: COAST PROFESSIONALS Brokered by EXP Realty.

$1,879,000
3 Beds ⋅ 3 Baths ⋅ 3,397 SqFt. ⋅ HILTONHEAD-448864 MLS
PRIME LOCATION with direct access to Sea Pines Plantation Club AND Beach Club. Utilize the lovely leisure trail across street, along the Heron Point Golf Course to the BEACH! Featuring an extensively remodeled kitchen, thoughtful bedroom separation, and the potential to add a 4th bedroom within the existing layout. Repeat rental activity and over 40 days already booked for Q1 of 2025. Relax poolside on the ALL-NEW pool patio and overlook the golf course with the cart path situated on the opposite side of the fairway. A fantastic opportunity to own a home that combines privacy with convenient access to world-class beaches, golf, and amenities!

25 Red Maple Road, Hilton Head Island

Listing courtesy of Collins Group Realty. Selling Office: Collins Group Realty.

$1,650,000
3 Beds ⋅ 3 Baths ⋅ 2,443 SqFt. ⋅ HILTONHEAD-448021 MLS
Location matters! Convenient Sea Pines living with a 180-degree views of Heron Point’s 15th Green situated on a private oversized home-site in close proximity to Sea Pines Center, Harbour Town & the Beach. This single level home features open concept entertaining inside and out. Current owners have upgraded the property including; hardwood floors, kitchen finishes, baths, laundry room, appliances, roof, HVAC system, duct work, spray foam insulation, water heater and outdoor pool resurfacing. Don’t miss this rare opportunity to own on one of the premier streets within the Sea Pines Resort. Pool converted to salt water in 2021. 2 car garage

8 Willow Oak W Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty. Selling Office: Alliance Group Realty/Howard Hanna Tate.

$1,675,000
4 Beds ⋅ 4 Baths ⋅ 3,000 SqFt. ⋅ HILTONHEAD-447404 MLS
Fabulous location in the heart of Sea Pines on a quiet neighborhood street - close to shopping, Harbour Town and the Beach. This 4BR/4BA home with lanai pool (great for entertaining!) is currently being enjoyed as a primary home, but it could be a great second home or investment property. It has been beautifully maintained and regularly updated. This is a great opportunity to make Sea Pines your next home!

15 Willow Oak W Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: Sea Pines Real Estate South Beach.

$2,100,000
4 Beds ⋅ 4 Baths ⋅ 3,400 SqFt. ⋅ HILTONHEAD-446404 MLS
Presenting one of the finest homes available in Sea Pines! This stunning single-story residence boasts 4 bedrooms and 4 baths, featuring beautiful hardwood floors throughout. The updated kitchen seamlessly flows into the dining area & family room, creating an inviting great room effect. The master bath offers a separate shower, double vanity, & a spacious walk-in closet. Enjoy the pristine patio and pool with a scenic view of the Heron Point Golf Course. The home was completely remodeled in 2002, adding 2 bedrooms & 2 full baths, expanding the living area to a total of 3,400 square feet. Located within walking or biking distance to the beach!

7 Red Maple Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Collins Group Realty.

$1,075,000
HILTONHEAD-444408 MLS
One of the most desirable streets in Sea Pines. This lot is just over half an acre offering spectacular views of the 2nd fairway of Heron Point golf course. It is located near the end of the cul de sac & only steps to the bike path that takes you directly to the Plantation golf club where you can play Heron Point & Atlantic Dunes golf courses or dine at Fraser's restaurant. Few more steps & you are at the beautiful beach club with all its amenities. We have plans for a 4,200 sq. ft. house complete w/ pool that was previously ARB approved, but would now have to be resubmitted. Want to build? Do not miss this location & opportunity.

23 Red Maple Road, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Blufft. Selling Office: Berkshire Hathaway HomeServices Hilton Head Blufft.

$1,635,000
5 Beds ⋅ 3 Baths ⋅ 2,663 SqFt. ⋅ HILTONHEAD-443445 MLS
Step into this beautifully updated home in Sea Pines Resort. Boasting 5 bedrooms and a mostly-single level design, this home sits on a private wooded lot with room for a pool. Hosting is made easy with an open floor plan, large kitchen, and the back of the home was reimagined to include a large climate controlled “Carolina Room” complete with wet bar, ice machine, and 2 keg taps-plus two large decks-one off each side. This home has been well maintained and is move-in-ready!

31 Willow Oak W Road, Hilton Head Island

Listing courtesy of Dunes Real Estate. Selling Office: Collins Group Realty.

$1,750,000
4 Beds ⋅ 4 Baths ⋅ 2,756 SqFt. ⋅ HILTONHEAD-439009 MLS
Sea Pines Escape! As soon as you walk inside your eye will be drawn to the sweeping lagoon to golf course views over the private pool. It features two primary bedrooms on the first level, a gourmet chef's kitchen, massive wet/wine bar, screened-in porch, & windows everywhere flooding the space with sunlight. Meticulously crafted down to the studs, this newly renovated 4 bed, 3.5 bath coastal gem boasts high-end finishes everywhere you look. EVERYTHING new! Sold furnished. Projected to do over 150k in rentals. Prime location! Quick walk to the beach, harbour town, shops/restaurants. Live the coastal lifestyle you've been dreaming of!

44 Willow Oak W Road, Hilton Head Island

Listing courtesy of Hilton Head Properties. Selling Office: William Raveis - Carolina LLC.

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