Hilton Head Island Homes with Free Form, Other, Private, Community Pool Description

Welcome to Hilton Head Island, South Carolina – a stunning coastal paradise renowned for its breathtaking beaches, lush landscapes, and vibrant community spirit. Nestled in Beaufort County, this idyllic island is not just a vacation destination; it’s a lifestyle choice that offers a perfect blend of relaxation and adventure.

Hilton Head Island boasts a rich tapestry of activities for all ages. From world-class golf courses and tennis facilities to miles of scenic bike trails and pristine beaches, there’s no shortage of outdoor enjoyment. The island’s commitment to preserving its natural beauty is evident in its abundant parks and nature preserves, making it a haven for nature lovers and outdoor enthusiasts alike.

When it comes to real estate, Hilton Head Island offers a diverse range of homes that cater to various tastes and lifestyles. Imagine living in a beautifully designed home that features a private community pool, perfect for those warm summer days. Many of these properties come with free-form pools that seamlessly blend into the landscape, creating a tranquil oasis for relaxation and entertaining. Whether you’re looking for a cozy villa, a luxurious waterfront estate, or a charming cottage, Hilton Head has it all.

With its inviting atmosphere and a close-knit community, Hilton Head Island is more than just a place to live; it’s a place to thrive. Experience the charm of island life while enjoying the modern conveniences that come with it. Come discover your dream home in this enchanting coastal community – where every day feels like a vacation!

Newest Hilton Head Island Homes with Free Form, Other, Private, Community Pool Description

$1,195,000

4 Beds ⋅ 5 Baths ⋅ HILTONHEAD-511954 MLS

Offered for the first time by its original owners, 342 Long Cove Drive is a rare opportunity to own one of Long Cove Club's distinctive custom residences. Thoughtfully designed and impeccably maintained since its construction, including a new roof in 2025, this timeless brick home blends enduring craftsmanship with exceptional architectural character. Privately sited on a beautifully landscaped homesite, the residence enjoys sweeping golf-to-lagoon views while offering remarkable privacy. Soaring ceilings, expansive windows, and light-filled living spaces create an open, airy atmosphere throughout, while the home's unique design offers warmth, flexibility, and timeless appeal. Designed for comfortable everyday living and gracious entertaining, the floor plan features two spacious primary suites, one on each level, elevator access to all levels, a dedicated office, generous gathering spaces, and a detached two-car garage. The private front brick courtyard surrounds a sparkling swimming pool, creating a secluded outdoor retreat unlike any other. Lovingly cared for over the years, the home presents an outstanding opportunity for its next owner to personalize the interiors while preserving the quality and architectural integrity that make it so special. Combining classic design, exceptional maintenance, and one of Long Cove's most desirable settings, this is a truly rare offering in one of Hilton Head Island's premier private communities. Long Cove Club is a community that features world-class amenities, including a top ranked Pete Dye designed golf course, deep water marina facilities, Jr. Olympic size pool, tennis, pickleball, bocce ball, basketball court, dog park, playground and community garden.

342 Long Cove Drive, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$995,000

4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-510654 MLS

Exceptional value on superbly maintained residence with spacious floor plan and expansive private pool in amenity rich Moss Creek. Features include natural stone flooring, granite counters, custom built-ins, vaulted ceilings, walls of windows to pool & grounds, stone surround gas fireplace, stainless steel appliances, max cabinet/counter space, recessed lighting, skylights, impressive storage space including walk-in attic, oversize 2 car garage + newer roof & energy efficient HVAC systems. Very livable/flexible floor plan boasts kitchen with breakfast bar, open to formal/casual dining, den/study, great room, 2 large 4 season Carolina rooms (screened + plexi-glass windows), well-appointed & private primary suite, 2 ample guest BR's & bath, powder room, large laundry room + huge bonus suite with kitchenette/BR/Living Area/Bath and pool view terrace! Owner groomed landscape/hardscape offers mature plantings, specimen trees, stay cool pool deck, secret garden, carriage lighting, and maximum privacy. All on quiet cul-de-sac street with primo central locale close to all this private club community has to offer!

18 Saw Timber Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$449,900

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-509589 MLS

Welcome to **Hilton Head Beach Club Villas**-where coastal convenience meets ultimate privacy. As one of the island's most desirable low-density complexes, it places you less than a 5-minute walk from the sand and just steps away from premier shopping, dining, and entertainment. This pet-friendly community features a relaxing on-site pool, while the property itself boasts a fenced-in courtyard and rear patio for your own private oasis. Whether you are looking for a lucrative short-term rental investment or your dream beachside second home, this property delivers it all!

11 Tanglewood Drive Unit 7, Hilton Head Island

Listing courtesy of Hilton Head Area Properties, LLC.

$485,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-507582 MLS

Beautifully situated in a quiet corner of the island, this charming villa offers the perfect blend of comfort, privacy, and convenience. Featuring two spacious bedrooms and one and a half baths, the villa provides ample room for relaxing and entertaining. Enjoy outdoor living on the inviting front patio or the beautiful brick patio, which backs up to serene woods, perfect for morning coffee or evening gatherings. Located just moments from Coligny Plaza's vibrant shopping and dining, Lowcountry Celebration Park, and the famous Coligny Beach, you'll be close to the best of island living. This pet-friendly villa is currently on the short-term rental market, offering excellent income potential for investors or a flexible vacation retreat. With one of the lowest monthly regime fees on the island-including insurance, this property is both an exceptional value and a rare find. Perfect for those seeking a peaceful getaway or a strong rental performer near Hilton Head's most beloved amenities.

11 Tanglewood Drive Unit 2, Hilton Head Island

Listing courtesy of Collins Group Realty.

$750

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-506994 MLS

Discover your perfect spring retreat at Swallowtail in Sea Pines with Week 10 ownership! Set in the heart of Hilton Head Island, this mid-March getaway offers a refreshing change of pace, with mild coastal weather, blooming scenery, and a more relaxed island vibe. Overlooking the 12th fairway of the Heron Point Golf Course, the property combines scenic golf views with easy access to everything that makes Sea Pines so special. You're just a short distance from the Harbour Town lighthouse, the Beach Club, and an array of dining, shopping, and outdoor experiences. Spend your days enjoying early rounds of golf, beach walks, or biking beneath moss-draped oaks, and your evenings unwinding in the charm of Harbour Town. With its low-maintenance ownership and prime location, Swallowtail offers an effortless way to enjoy Hilton Head year after year. Take advantage of this opportunity to claim your own slice of Sea Pines in one of the island's most inviting seasons-Week 10 is waiting.

70 Lighthouse Road Unit 2879, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$475,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-505362 MLS

Seller is offering a $5000 credit at closing with an acceptable offer! Discover the perfect getaway at this updated villa, ideally situated near Hilton Head Island's best beaches, dining, shopping, and entertainment. Rare opportunity to own a piece of HHI paradise with 2 private courtyards in Hilton Head Beach Club Villas! This 2-bedroom, 1.5 bath villa is being sold fully furnished and ready for the new owners and their guests! The open floor plan is bright & airy w/a full kitchen ready for your cooking & entertaining needs. The living area walks out to the spacious rear courtyard, complete with a dining table and gas grill nestled under the lush palm trees, with access to the sundeck and pool. You will find two bedrooms and a shared, recently remodeled bath upstairs. The Primary bedroom has a private balcony for enjoying coffee or a cocktail. The villa is a quick walk to the beach, Coligny Plaza with its shops and restaurants, or Low Country Celebration Park. Don't miss your opportunity to call this villa your favorite escape!! Currently, an active vacation rental that is managed by a local professional property management company!

11 Tanglewood Drive Unit 34, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$99,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-503819 MLS

Direct Harbourfront View! What are you waiting for? Come own a piece of paradise! Completely renovated quarter-share condo in a Mediterranean-style Harbour community. Enjoy live music & entertainment from the balcony. Enjoy everything the area has to offer without ever getting in the car. Amenities include a private pool, hot tub, gas grills, private secure parking, & access to Palmetto Dunes. Experience world-class amenities: beach, golf, tennis, lagoon system & leisure trails. Yearly fee incl: taxes, insurance, utilities, etc! Just bring your suitcase. Hassle-free deeded ownership provides 13 rotating weeks of use on Hilton Head.

9 Harbourside Lane Unit 7312B, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC.

$1,300

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-503185 MLS

Own Your Spring Escape at Swallowtail in Sea Pines - Week 11! Claim your perfect spring retreat with deeded Week 11 in the heart of Hilton Head Island's premier Sea Pines community. This beautifully situated Swallowtail villa overlooks the 12th fairway of the Heron Point Golf Course, delivering that ideal mix of peaceful golf-course views and effortless access to the island's best amenities. Nestled between the iconic Harbour Town lighthouse and the sun-soaked Sea Pines Beach Club, you'll enjoy quick access to world-class golf, pristine beaches, waterfront dining, and boutique shopping. Mornings on the course, afternoons by the ocean, evenings exploring Harbour Town-your spring getaway is always ready when you are. This is carefree, low-maintenance island living at its best. Don't miss the opportunity-secure your Week 11 spring escape today!

70 Lighthouse Road Unit 2890, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$2,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-501423 MLS

Experience the magic of Hilton Head Island. Prime deeded summer weeks 31. Swallowtail at Sea Pines, a beloved and cherished property, offers the dream vacation lifestyle luxurious, carefree. Nestled midway between Harbour Towns iconic lighthouse and the sun-soaked Beach Club, Swallowtail places you steps from world-class golf, pristine beaches, waterfront dining, and vibrant arts. Whether you crave serene mornings by the ocean, sunset sails, or championship fairways, everything you love is just moments away! Your Summer, Your Way Flexibility Included!

70 Lighthouse Road Unit 2901, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$12,900,000

8 Beds ⋅ 15 Baths ⋅ HILTONHEAD-452855 MLS

This architectural masterpiece spans two waterfront lots and features a primary residence and guest home. The estate offers eight bedrooms, eleven full baths, and four half baths. Exceptional amenities include a grand foyer, a great room with coffered ceilings, a gourmet kitchen, a movie theater, a bowling alley, a media room, and a wine cellar. Additional highlights include an elevator, extensive millwork, an outdoor kitchen, pool, hot tub, Koi pond, piers, five fireplaces, a seven-car garage, and a spa area. This one-of-a-kind property does not exist anywhere else! Enjoy all that Wexford has to offer along with the luxury of 80 Bridgetown!

80 Bridgetown Ln, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$6,000,000

5 Beds ⋅ 7 Baths ⋅ HILTONHEAD-452750 MLS

Stately, Sound front home with Ocean views. 199 ft of Waterfront. Water views from every room to include Ocean, Sound, Lagoon and #6 Oyster Reef Golf green. The home boasts man-made and natural elements that make it Dazzle. Designed for Cooking and Entertaining with large open concept spaces surrounded by glass. Well designed Chefs Kitchen to include Sub zero refrigerators, Wolf cooktop and Miele appliances. Formal living spaces include Cypress ceilings, Rosewood inlays, White Oak flooring, Teak inlays and 2-story Stone and Copper clad Fireplace. Expansive Resort style Pool with Spa, Wading area, new decking and Pool House. 4 Car Garage with quiet lift door mechanisms. Glass door Elevator, Wine Room, Den, Game & Theater rooms.

16 Oyster Shell Lane, Hilton Head Island

Listing courtesy of Lighthouse Realty.

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