Refine Search
Sort by
$2,295,000
7 Beds 5 Baths HILTONHEAD-509321 MLS
Brand-new 7-Bedroom, 4.5 Bath Hilton Head Island home with private pool, and elevator to all floors. This spacious luxury home features 10-foot ceilings on the main level, and in the primary suite, 9-foot ceilings upstairs, wide-plank flooring, a hand-hewn exposed beam ceiling from reclaimed wood, an electric fireplace, and a grand staircase with a chandelier. The chef's kitchen includes quartz countertops, built-in wine chiller, Forno gas double oven and stove, Forno double refrigerator/freezer combo, stainless appliances, and oversized island. Dual sliders open from the living room to a huge covered balcony. The home offers two laundry areas, a first-floor primary suite with dual vanities, four bedrooms upstairs, two additional garage-level bedrooms, and an oversized garage. Enjoy an in-ground private pool, large side yard, and generous spacing from neighboring homes. Ideal as a primary residence, second home, or investment property. Listed price is for the real property only. Turnkey Pottery Barn furniture package available for separate purchase by bill of sale.

37 Oleander Street, Hilton Head Island

$2,295,000
7 Beds 5 Baths HILTONHEAD-506962 MLS
Brand-new 7-Bedroom, 4.5 Bath Hilton Head Island home with private pool, and elevator to all floors. This spacious luxury home features 10-foot ceilings on the main level, and in the primary suite, 9-foot ceilings upstairs, wide-plank flooring, a hand-hewn exposed beam ceiling from reclaimed wood, an electric fireplace, and a grand staircase with a chandelier. The chef's kitchen includes quartz countertops, built-in wine chiller, Forno gas double oven and stove, Forno double refrigerator/freezer combo, stainless appliances, and oversized island. Dual sliders open from the living room to a huge covered balcony. The home offers two laundry areas, a first-floor primary suite with dual vanities, four bedrooms upstairs, two additional garage-level bedrooms, and an oversized garage. Enjoy an in-ground private pool, large side yard, and generous spacing from neighboring homes. Ideal as a primary residence, second home, or investment property. Listed price is for the real property only. Turnkey Pottery Barn furniture package available for separate purchase by bill of sale.

35 Oleander Street, Hilton Head Island

$2,195,000
4 Beds 5 Baths HILTONHEAD-510279 MLS
Welcome to your coastal dream home just steps from the beach! Completed in 2024 and offered fully-furnished, this stunning 4-bedroom, 4.5-bath Lowcountry retreat is perfectly located in Hilton Head Island's sought-after Folly Field beachside neighborhood. Designed for effortless island living, the bright and open floor plan showcases relaxed coastal charm, spacious gathering areas, and designer finishes throughout. The first-floor primary suite offers privacy and convenience, while three generously sized guest suites (each with their own full bath) upstairs provide plenty of room for family and friends. Step outside to your own private backyard oasis featuring a sparkling pool and spa, screened-in outdoor bar and spacious lounge area - perfect for entertaining, relaxing, or unwinding after a day on the beach. Folly Field does have a private beach entrance for owners. Whether you're searching for a luxury second home, a turnkey vacation rental, or the perfect blend of both, this exceptional property offers modern construction, resort-style amenities, and outstanding rental potential in one of Hilton Head Island's most desirable beachside communities.

8 Moonshell Road, Hilton Head Island

$1,799,999
4 Beds 3 Baths HILTONHEAD-452326 MLS
Stunning Custom-Built 4-Bedroom Home in Prime Folly Field, Hilton Head - Steps from the Beach. Discover your dream coastal retreat in the highly desirable Folly Field neighborhood of Hilton Head Island. This exceptional custom-built 4-bedroom (plus unique loft), 3-bath home offers 2,523 square feet of timeless elegance and modern luxury on a generous lot. Just a short 7-10 minute stroll to Folly Field Beach Park, this property delivers the perfect blend of beach access, privacy, and investment potential. Step inside to an inviting open-concept floor plan flooded with natural light. Soaring vaulted ceilings and a dramatic wall of windows frame the gorgeous great room, creating an airy, spacious feel ideal for relaxing and entertaining. The chef's dream gourmet kitchen features elegant marble countertops, high-end stainless steel appliances (including a premium Bertazzoni range, Bosch, and Blomberg), and beautiful custom stone and tile work. Charming barn doors, a step-down living area, and an expansive balcony add character and functionality. Bonus First-Floor Apartment: This home includes a completely separate 1-bedroom, 1-bath apartment with its own full kitchen and private lanai - offering two distinct living/rental units for the price of one. Whether you're looking for a primary residence, second home, or turnkey investment, the strong short-term rental demand in Folly Field makes this a high-performing opportunity.

9 Mimosa St, Hilton Head Island

$1,699,000
5 Beds 4 Baths HILTONHEAD-511679 MLS
Sandcastles by the Sea is a gated community gem centrally located mid-island and a 5-min walk (by direct bike path) to one of Hilton Head Island's most desired public beaches. This 6BR|4BA versatile luxury property has an array of opportunities including primary or secondary residence, multigenerational utilization, short/long term rental revenue or corporate investment for perks & prospects. Enjoy year-round swimming in the heated private pool or throw your cares to the southern breeze from a large balcony overlooking a wildlife haven in the neighborhood lagoon. An elevator provides seamless access to all three levels, offering everyday convenience while enhancing the home's comfort and refined design. Nestled within a gated, golf cart and low-speed vehicle-friendly community with nightly security patrols, this exceptional property offers the perfect blend of privacy, convenience, and coastal elegance. Just moments from the beach, the spacious residence is designed for effortless indoor-outdoor living, making it a rare opportunity to own a premier luxury retreat in one of Hilton Head Island's most desirable beachfront communities. Excellent rental history available upon request. House will be sold FULLY FURNISHED.

124 Sandcastle Court, Hilton Head Island

$1,695,000
5 Beds 6 Baths HILTONHEAD-511552 MLS
Welcome to 90 Sandcastle Court, a spacious, beautifully appointed beach home in the gated Sandcastles by the Sea community. One of the larger homes in the neighborhood, this fully furnished, turnkey property offers five bedrooms, four full baths, two half baths, and elevator access to every level. The open-concept main living area is designed for gathering and entertaining, with a gourmet kitchen featuring granite countertops, GE Monogram appliances, a gas range, generous dining space, and an inviting living area. The lower level provides flexible recreation and additional living space with direct access to the private pool, hot tub, patio, and outdoor entertaining areas. Additional highlights include a large deck, low-maintenance artificial turf lawn, EV charging outlet, and multiple indoor and outdoor spaces for relaxing with family and guests. Ideally located just a short walk from the beach and close to Hilton Head Island's restaurants, shopping, golf, and attractions. Offered fully furnished with approximately $110,000 in gross rental revenue already booked for 2026, this exceptional property is ready to enjoy as a primary residence, vacation home, or income-producing short-term rental.

90 Sandcastle Court, Hilton Head Island

$1,650,000
6 Beds 4 Baths HILTONHEAD-509596 MLS
Folly Field rental machine built in 2020! Popular Wilmington floorplan. Sandcastles by the Sea is an ocean-oriented gated community approximately 780 yards to the beach! This 6-bedroom, 4 Full bath home has an open floor plan and is perfect for large groups on vacation! The elevator serves the garage and all three floors above. Ride from the private heated in-ground pool to the top floor that has a 3D Projection Movie Theater with 120 inch screen! All theater electronics included. Luxury Vinyl Plank (LVP) throughout, epoxy garage floor, 220 Volt Level 2 EV car charger, and a large paver patio with hot tub! Kids bunk room complete with 4 arcade machines. Sold fully furnished. Sleeps 22. Great opportunity for a primary home, secondary home or investment property! Currently on the Short Term Rental Market.

83 Sandcastle Court, Hilton Head Island

$1,645,000
6 Beds 4 Baths HILTONHEAD-504810 MLS
Rental machine grossing over $100K the past two years! Ideally positioned within a private gated community just a 9-minute stroll to the beach. Designed for both grand entertaining and relaxed seaside living, this six-bedroom, four-bath, three-story residence offers exceptional scale, comfort, and privacy. An elevator services all three levels, providing effortless access throughout the home and adding both convenience and sophistication. Expansive living areas are thoughtfully arranged to accommodate 20+ guests, making the property ideal for multi-generational gatherings, executive retreats, or hosting extended family in style. Outdoors, a private heated in-ground pool creates a true resort-style experience, while the backyard paver patio overlooks a peaceful wooded backdrop. Located in a golf cart and Low Speed Vehicle-friendly neighborhood with nighttime security patrol, the community offers both leisure and peace of mind. The combination of gated access, quick proximity to the beach, and spacious design makes this property a standout in the coastal luxury market.

119 Sandcastle Court, Hilton Head Island

$1,599,000
6 Beds 4 Baths HILTONHEAD-504713 MLS
Turnkey. Proven. Profitable. Welcome to 99 Sandcastle Court-an exceptional, fully furnished short-term rental opportunity just a short walk from the sand at Folly Field Beach on Hilton Head Island. Built in 2020 and never before offered for sale, this 6-bedroom, 4-bath coastal retreat spans 3,222 square feet and delivers the rare combination of luxury design and consistent income performance. With over 50 five-star reviews in the past 24 months alone, this property has already established a powerful online presence, repeat guest base, and exceptional guest satisfaction, key drivers of short-term rental success. The heavy lifting has been done. Step into a fully operational, high-demand asset from day one. Designed to maximize occupancy and nightly rates, the spacious open-concept floor plan comfortably accommodates large groups and multi-family bookings, Hilton Head's most profitable rental segment. The expansive living area flows seamlessly into a chef-inspired kitchen and generous dining space, creating an inviting environment guests consistently rave about. The private heated pool and oversized back patio elevate the guest experience and extend the rental season, supporting premium pricing throughout the year. Outdoor entertaining space is a major draw for vacationers and this home delivers in a way that sets it apart from older inventory. Six well-appointed bedrooms and four full baths provide flexibility for owners and guests alike. Modern construction (2020) means lower maintenance expectations, updated systems, and enhanced insurability compared to legacy beach homes. Located within near distance to one of Hilton Head's most desirable beaches, this property offers a location that drives consistent occupancy year after year. Beach access, bike paths, dining, and island amenities are all just moments away-exactly what today's vacationers seek. Whether you're expanding your portfolio or securing a luxury second home that generates strong income while you're away, 99 Sandcastle Court is a rare opportunity to acquire a fully furnished, income-producing asset with an established track record in one of the Southeast's premier vacation markets. This is not a startup rental. This is a performing property ready for its next owner.

99 Sandcastle Court, Hilton Head Island

$1,395,000
5 Beds 4 Baths HILTONHEAD-447145 MLS
Sale subject to third-party/lender approval. Seller pursuing short sale. Property sold as-is. Folly Field Rental Machine built in 2019! Buxton Floorplan. Gated community only 10 minutes to the beach! This 5-bedroom, 4 full bath home has an open floor plan with a large kitchen, dining area, and living room with an attached screened porch! One bedroom furnished as a bunk room. The elevator takes you from the garage to all 3 floors above. Luxury Vinyl Plank (LVP) throughout. Private heated in-ground pool overlooking a brick paver patio and landscaped view. Sold fully furnished. Sleeps 18. Great opportunity for a primary home, secondary home, or investment property! Currently on the Short Term Rental Market.

101 Sandcastle Court, Hilton Head Island

$955,000
3 Beds 2 Baths HILTONHEAD-508893 MLS
Nestled just steps from the ocean, this charming beach cottage offers the perfect blend of coastal comfort and relaxed seaside living. Three bedrooms and two full baths plus a huge kitchen, breakfast room and light-filled great room. A huge laundry room/mud room is great for extra storage. A one-car carport keeps your car out of the sun. The massive backyard is fenced and has an oversized deck with a hot tub, a sandy area great for your hammock, and a storage shed. The impressive live oak tree welcomes you as you drive up. With sunlit interiors, breezy open spaces, and thoughtfully curated décor inspired by the ocean, the cottage creates a warm and inviting weekend getaway or permanent beach home. Spend mornings on the back deck enjoying a cup of coffee, afternoons spent on sandy beaches, and evenings under stunning coastal sunsets. Whether you're seeking a peaceful getaway or a memorable beachside escape, this cottage provides a cozy haven where every day feels like a vacation. Folly Field is a quaint community just a short stroll to Nalas Beach Bar, a short bike ride to Shelter Cove, and all of its fun spots (restaurants, shopping, nightlife, and waterfront activities). This home has been lovingly updated and you will be totally impressed!

8 Azalea Street, Hilton Head Island

$329,900
2 Beds 2 Baths HILTONHEAD-511507 MLS
Beautifully updated, fully furnished 2-bedroom, 2-bath end-unit villa located in the highly sought-after Hilton Head Beach & Tennis Resort. Whether you're looking for a turnkey vacation home, a full-time residence, or an established investment property, this villa offers the perfect combination of comfort, convenience, and coastal living. The bright, open floor plan features luxury vinyl plank flooring, an updated kitchen with newer appliances, tasteful coastal décor, and a private balcony overlooking the pickleball courts. Being offered fully furnished, this villa is truly move-in or rental ready. Located just a short walk from the beach, owners and guests enjoy access to an impressive array of resort amenities, including one of Hilton Head's largest oceanfront pools, three on-site restaurants, a beach bar, pickleball and tennis courts, a fitness center, bike rentals, playground, 24-hour gated security, and beautifully maintained grounds. Ideally situated near Coligny Plaza, Shelter Cove, Harbour Town, championship golf courses, shopping, dining, and miles of scenic bike paths, this property offers everything buyers love about Hilton Head Island. With a strong rental history and exceptional resort amenities, this is a rare opportunity to own a beautifully maintained coastal retreat with outstanding investment potential.

40 Folly Field Road Unit APT E17, Hilton Head Island

board logo

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.

board logo

This information is deemed reliable, but not guaranteed. Neither the Lowcountry Regional MLS, nor the listing broker, nor their agents or subagents are responsible for the accuracy of the information. The buyer is responsible for verifying all information. This information is provided by the Lowcountry Regional MLS for use by its members and is not intended for use for any other purpose.