Refine Search
Map
Sort by
$490,000
2 Beds ⋅ 2 Baths ⋅ 1,281 SqFt. ⋅ HILTONHEAD-512155 MLS
Enjoy easy island living in this 2BR/2BA second-floor residence in the gated community of The Preserve at Indigo Run. With no neighbors above, this home offers an added level of privacy and a quiet setting. The interior features wood flooring, updated appliances, a convenient coffee bar, pantry storage, and finished closets. Recent improvements include brand new carpet in the bedrooms, an updated main bathroom in 2025 and a screened-in porch completed the same year, creating a comfortable outdoor living space to enjoy throughout the seasons. Residents of The Preserve have access to a community pool, fitness center, tennis courts, and clubhouse. Located on Hilton Head's desirable North End, you're convenient to the beach, restaurants, shopping, and other island amenities. Short-term rentals are not permitted, making this an appealing option for a primary home, second residence, or long-term rental property.

4 Indigo Run Drive Unit 3810, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$75,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512544 MLS
This beautifully renovated Tennis Villa offers a unique opportunity to enjoy your own place at the beach at a fraction of the cost of full ownership. This is a DEEDED 1/5equity ownership share of Villa F13-not a timeshare-shared with just four other owners. Enjoy 12+ rotating weeks each year while paying only 1/5 of the operating and regime costs. The bright end unit features a modern kitchen, updated bathrooms, new flooring, stylish furnishings, and extra natural light. With two bedrooms, two bathrooms, and a pull-out sofa, the villa comfortably accommodates 6-8 guests. All within just steps from the beach. Located in the Hilton Head Beach and Tennis community, owners enjoy a large outdoor pool, two onsite bars and restaurants, bike rentals, pickleball courts, tennis courts, and easy access to the beach. It's an affordable and convenient way to have your own Hilton Head Island getaway without the expense and responsibilities of full ownership. Ownership is for personal and family use only. No rentals or pets permitted.

40 Folly Field Road Unit APT F 13, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$579,000
2 Beds ⋅ 2 Baths ⋅ 1,665 SqFt. ⋅ HILTONHEAD-512420 MLS
One of the Preserve at Indigo Run's most popular model and very nicely updated and upgraded. This a second floor unit with high ceilings, wood burning fireplace, and an over-sized two car attached garage. Private wooded views, an updated kitchen and bathroom add to the appeal of this very special villa adjacent to the prestigious Indigo Run community. The spacious Magnolia floor plan features two nicely-sized bedrooms, two full baths, 1,665 square feet and a great layout with many windows and plenty of natural light. Enjoy a dining area, eat in kitchen with island and pantry, laundry room (washer and dryer convey), and large entry way. Security gate, pool, tennis, club house, cabana and fitness center. No POA fees.

4 Indigo Run Drive Unit 3320, Hilton Head Island

Listing courtesy of Real Estate Five Of The Lowcountry.

$5,000
3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512391 MLS
Experience luxury Hilton Head Island living without the full-time ownership costs in a private gated enclave and a part of prestigious Indigo Run, featuring beautifully furnished 3-bedroom, 3-bath detached homes and one of the Island's most flexible fractional ownership opportunities. Owners enjoy 27 annual days and nights with customizable reservation options perfect for weekend escapes, golf getaways, family vacations, or extended coastal stays throughout the year. This resort-style community offers exclusive amenities including a private clubhouse with concierge services, sparkling pool, two hot tubs, fitness center, billiards room, and spacious big-screen TV lounges. Unlimited golf playing privileges at 7 premier Hilton Head golf courses for only a nominal cart fee. Owners have access to Golden Bear, Indigo Run tennis facilities, Sunningdale Park pool, scenic paved leisure trails, and an easy bike ride to the beach creating the ULTIMATE Lowcountry lifestyle experience. High speed WiFi, outdoor grills and multiple TVs are available throughout all residences and clubhouse facilities. Ideal for vacation homeowners, golf enthusiasts, and buyers seeking affordable luxury ownership in one of Hilton Head Island's most desirable gated communities.

55 Aberdeen Court, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$299,900
2 Beds ⋅ 3 Baths ⋅ 1,389 SqFt. ⋅ HILTONHEAD-512130 MLS
Hilton Head living without the Hilton Head price tag! This inviting 2-bedroom, 2.5-bath villa in The Gatherings offers a rare opportunity to own on Hilton Head Island at an approachable price point, with the added benefit of a low-maintenance lifestyle. Ideally positioned near the foot of the Hilton Head bridge, this location provides quick access to everything the Island offers while keeping Bluffton, Bluffton Parkway, shopping, dining, and everyday conveniences just minutes away. Inside, an updated kitchen opens to a generous dining and living area, creating a comfortable, spacious feel for everyday living or entertaining. Step outside to the wooden deck overlooking a peaceful lagoon setting-an ideal spot for morning coffee, relaxing at the end of the day, or simply enjoying the Lowcountry surroundings. What truly sets The Gatherings apart is its unique ownership structure. Although legally classified as a condominium, the community includes a variety of home styles, and the regime handles many major exterior responsibilities, simplifying ownership. Regime services include building maintenance, landscaping, insurance components, common water and sewer, pest control, refuse, pool maintenance, and more. The community also offers a pool, assigned parking, and a convenient residential setting. Whether you're looking for a primary residence, lock-and-leave second home, downsizing opportunity, or an affordable way to establish your Hilton Head Island address, this property delivers an appealing combination of location, lifestyle, and value.

111 Sutherland Way Unit 111, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$1,650
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512324 MLS
Your Spicebush Fall Week 37 Awaits! Tucked within the heart of Hilton Head Island's prestigious Sea Pines community, this ownership places you just moments from the Sea Pines Beach Club and Plantation Club Golf Course. Perfectly situated, your Spicebush Week 37 offers effortless access to world-class golf, pristine beaches, waterfront dining, and the island's most celebrated events. Embrace coastal living at its best-start your mornings by the sea, unwind beneath golden sunsets, and savor the timeless charm of Sea Pines Resort. With refined, low-maintenance ownership, your annual island escape is always ready when you are.

124 N Sea Pines Drive Unit 582, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$1,500
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512325 MLS
Own Your Late Winter Escape! Make Hilton Head your tranquil tradition! Enjoy the islands serene off-season with deeded ownership of Week 8 at Swallowtail, nestled in the heart of Hilton Heads prestigious Sea Pines community. Perfectly positioned between the iconic Harbour Town Lighthouse and the Beach Club, this property places you steps from world-class golf, uncrowded beaches, waterfront dining, and early-spring cultural events. Experience coastal living at its most peaceful stroll mild, sunny beaches, sail into crisp sunset evenings, and savor the charm of Harbour Town without the crowds. With luxurious, low-maintenance ownership, your late-winter retreat is forever waiting.

70 Lighthouse Road Unit 2875, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$25,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512232 MLS
Welcome to your coastal getaway! Own a deeded 2BR, 2BA quartershare at Brigantine Quarters in Shipyard. Enjoy 13 rotating weeks a year in this beautifully designed residence with vaulted ceilings and a large balcony with golf views. Prime weeks for 2027 include 4th of July and December 18th through New Year's Day 2028. This mini-resort includes tennis, pickleball, pools, a playground, and a private beach gate for BQ owners and guests. Maintenance fee covers appliances, furniture, maintenance upkeep, taxes, Shipyard fees, and more, ensuring a stress-free experience, ideal for personal use or rentals.

55 Barcelona Road Unit 242C, Hilton Head Island

Listing courtesy of The Homesfinder Realty Group.

$2,300
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512178 MLS
Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 20, ideally positioned in the late May when the island is at its springtime best. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. This desirable villa overlooks a lush lagoon, providing peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with refreshing ocean breezes and serene golf course vistas, then setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. May's comfortable temperatures and blooming landscapes create the perfect setting for beach walks, outdoor dining, dolphin cruises, and all that Sea Pines has to offer-without the crowds of peak summer. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep.

70 Lighthouse Road Unit 2885, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$350,000
2 Beds ⋅ 2 Baths ⋅ 1,072 SqFt. ⋅ HILTONHEAD-511911 MLS
Beautifully updated and move-in ready, this first-floor 2-bedroom, 2-bath villa offers easy, stair-free living in one of Hilton Head Island's most convenient communities. The light-filled interior features an open floor plan with updated flooring throughout, a spacious living area, and a beautifully renovated kitchen with crisp white cabinetry, granite countertops, stainless steel appliances, and a large peninsula with bar seating. Both bedrooms are generously sized, while the updated baths feature fresh, timeless finishes, including a walk-in shower. An in-unit laundry room adds everyday convenience, and the covered outdoor living area provides the perfect spot to relax and enjoy the island setting. Ideally located mid-island, Summer House offers a peaceful, gated setting just minutes from Folly Field Beach, shopping, dining, golf, and everyday conveniences. Community amenities include a resort-style pool, hot tub, fitness center, clubhouse, tennis court, car wash station, and beautifully landscaped grounds. Whether you're looking for a primary residence, lock-and-leave island retreat, or investment opportunity, this turnkey villa is ready to enjoy.

380 Marshland Road Unit C17, Hilton Head Island

Listing courtesy of Charter One Realty.

$35,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511949 MLS
Why own more than you can use? Premium location and walking distance to the beach! Ocean Palms is a 1/5th deeded fractional ownership property allowing each owner 10 weeks of use per year on a calendar rotation of 2 weeks back to back 5 times annually. Management by the Westin Oceanfront Resort & Spa allows use of the hotel amenities, fitness center, oceanfront pool complex, beach access and resort shuttle. A great golf & tennis package is included with ownership. This wonderful 2 bedroom/2 bath designer furnished 1st floor Sanibel floor plan has 1350 htd sq ft, a screened porch, with great golf & lagoon views. Onsite open house/model villa open daily.

14 Wimbledon Court Unit 407-4, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$1,800
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511928 MLS
Enjoy the laid-back elegance of Hilton Head Island during deeded Week 15 in late April, when the island is in full bloom and spring has settled in beautifully. Swallowtail at Sea Pines delivers a refined, low-maintenance vacation experience in an unbeatable setting. Perfectly positioned between Harbour Town's famous lighthouse and the sun-filled Beach Club, you're just a short stroll from top-tier golf courses, unspoiled beaches, waterfront restaurants, and a lively arts and culture scene. Imagine starting your days with gentle ocean breezes and warm spring sunshine, exploring miles of shaded bike paths beneath towering live oaks, or spending afternoons on award-winning fairways in ideal weather. However you like to unwind, it's all right at your doorstep, your spring getaway, tailored to you, with flexibility built in.

70 Lighthouse Road Unit 2871, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$466,000
2 Beds ⋅ 2 Baths ⋅ 1,281 SqFt. ⋅ HILTONHEAD-511916 MLS
This 2 BDRM/ 2 BA Hawthorne modle. 2nd floor flat with 1 car garage. walk in closets, newer laminant flooring in the family areas, and a newly renovated kitchen with updated appliances. This is an outstanding layout with privacy bedrooms on each side. The Preserve is a gated residential ( no short term rentals allowed) condo community located right off of 278 on the North End of Hilton Head Island. Amenities abound with old growth trees, 24 hour gym, tennis/pickleball courts, and onsite management. Minutes from Main Street, Hilton Head Hospital, and multiple grocery stores, restaurants, and retail stores.

4 Indigo Run Drive Unit 711, Hilton Head Island

Listing courtesy of Charter One Realty.

$259,000
2 Beds ⋅ 2 Baths ⋅ 864 SqFt. ⋅ HILTONHEAD-511637 MLS
Unbeatable value and an incredible location 2 blocks from the beach! This beautifully updated 2-bedroom, 1.5-bath condo is an ideal choice for a primary residence, vacation getaway, or income-producing short- or long-term rental. Recent renovations include brand-new luxury vinyl plank flooring throughout, freshly painted ceilings and walls after removing the popcorn ceilings, updated light fixtures, washer & dryer, and more. The thoughtfully designed layout offers each bedroom its own private vanity with sink and toilet, connected by a shared walk-in shower for added convenience and privacy. Step outside onto the private balcony to enjoy sunny afternoons and warm coastal evenings. The property also boasts an excellent rental history, making it an attractive investment opportunity. Just around the corner from The Bank brewery and restaurant, Harris Teeter and Publix grocery, and a variety of shopping and dining options. So close to Lowcountry Celebration Park/Coligny and all the area has to offer! Many brand-new furnishings have recently been purchased and are included with the sale, making this a truly turnkey opportunity. Professional photos will be available the week of 7/27.

104 Cordillo Parkway Unit I3, Hilton Head Island

Listing courtesy of Coldwell Banker Realty.

$1,500
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511868 MLS
Owner is also selling Week 17 (Unit 2874) and is open to offering a discounted price if both weeks are purchased together-an excellent opportunity to enjoy two consecutive weeks in paradise! Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 18, ideally positioned in the first week of May when the island is at its springtime best. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. This desirable villa overlooks a lush lagoon, providing peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with refreshing ocean breezes and serene golf course vistas, then setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. May's comfortable temperatures and blooming landscapes create the perfect setting for beach walks, outdoor dining, dolphin cruises, and all that Sea Pines has to offer-without the crowds of peak summer. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep. With the option to purchase the adjoining Week 17 at a discounted package price, this is a rare opportunity to enjoy two consecutive weeks in one of Hilton Head Island's premier vacation destinations.

70 Lighthouse Road Unit 2875, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$230,000
2 Beds ⋅ 2 Baths ⋅ 864 SqFt. ⋅ HILTONHEAD-511836 MLS
Investor Opportunity! This 2 bedroom, 1.5 bath condo offers excellent income-producing potential in highly sought-after location. Just minutes from Coligny Plaza, the beach, dining, shopping, and entertainment, this property is ideally positioned to attract both vacation and long-term renters. With strong rental appeal, low entry cost, and the opportunity for consistent cash flow and long-term appreciation, this condo is an outstanding addition to any investment portfolio. Don't miss your chance to own an affordable property on Hilton Head Island.

104 Cordillo Parkway Unit M2, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$900
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511802 MLS
Own Your Spring Escape at Swallowtail in Sea Pines - Week 13! Seize the opportunity to own deeded Week 13 in the heart of Hilton Head Island's premier Sea Pines community. This stunning Swallowtail property, situated along the 12th fairway of the Heron Point Golf Course, offers the perfect blend of golf course tranquility and coastal adventure. Positioned between Harbour Town's iconic lighthouse and the Beach Club's sun-kissed shores, Swallowtail offers easy access to championship golf, pristine beaches, waterfront dining, and luxury boutiques. Whether you're spending your mornings on the green, afternoons lounging on the beach, or evenings exploring the charming Harbour Town, Swallowtail offers the low-maintenance luxury lifestyle you've been dreaming of. Don't miss the chance to make this slice of paradise yours - secure your Week 13 getaway today!

70 Lighthouse Road Unit 2890, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$1,500
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511798 MLS
Owner is also selling Week 18 (Unit 2875) and is open to offering a discounted price if both weeks are purchased together-an excellent opportunity to enjoy two consecutive weeks in paradise! Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 17, ideally positioned in the first week of May when the island is at its springtime best. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. This desirable villa overlooks a lush lagoon, providing peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with refreshing ocean breezes and serene golf course vistas, then setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. May's comfortable temperatures and blooming landscapes create the perfect setting for beach walks, outdoor dining, dolphin cruises, and all that Sea Pines has to offer-without the crowds of peak summer. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep. With the option to purchase the adjoining Week 18 at a discounted package price, this is a rare opportunity to enjoy two consecutive weeks in one of Hilton Head Island's premier vacation destinations.

70 Lighthouse Road Unit 2874, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$285,000
3 Beds ⋅ 3 Baths ⋅ 1,250 SqFt. ⋅ HILTONHEAD-511388 MLS
Perfectly situated for easy access to Hilton Head Island or Bluffton! This well maintained 3 bed, 3 bath stand alone condo offers spacious living with a large outdoor deck and onsite amenities! Approximately 1,250 square feet, this property presents an outstanding opportunity as a full-time residence, vacation getaway, or investment property. This light and bright home features an eat-in kitchen that opens up to the large living room, enjoy wood floors, stainless steel appliances, granite countertops and plantation shutters throughout! The first floor offers two comfortable bedrooms, two full baths, and a conveniently located laundry closet. Upstairs, you'll find a spacious private suite complete with a large bedroom, full bath, and generous closet space, as well as storage -perfect as a primary retreat or private guest suite. The Gatherings is an established neighborhood with a welcoming atmosphere and longtime residents. Close to shopping and restaurants, this home is a must see!

38 Wee Drive Unit 38, Hilton Head Island

Listing courtesy of Engel & Volkers.

$35,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511529 MLS
Why own more than you can use? Premium location and walking distance to the beach! Ocean Palms is a 1/5th deeded fractional ownership property allowing each owner 10 weeks of use per year on a calendar rotation of 2 weeks back to back 5 times annually. Management by the Westin Oceanfront Resort & Spa allows use of the hotel amenities, fitness center, oceanfront pool complex, beach access and resort shuttle. A great golf & tennis package is included with ownership. This wonderful 2 bedroom/2 bath designer furnished 2nd floor Sanibel floor plan has 1350 htd sq ft, screened porch & balcony, and overlooks the front pool area. Onsite open house/model villa open most days.

14 Wimbledon Court Unit 204-1, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$35,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511423 MLS
Why own more than you can use? Premium location and walking distance to the beach! Ocean Palms is a 1/5th deeded fractional ownership property allowing each owner 10 weeks of use per year on a calendar rotation of 2 weeks back to back 5 times annually. Management by the Westin Oceanfront Resort & Spa allows use of the hotel amenities, fitness center, oceanfront pool complex, beach access and resort shuttle. A great golf & tennis package is included with ownership. This wonderful 2 bedroom/2 bath designer furnished 2nd floor Sanibel floor plan has 1350 htd sq ft, a screened porch & balcony, and overlooks the front pool area. Onsite open house/model villa open daily.

14 Wimbledon Court Unit 202-1, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$25,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511398 MLS
Why own more than you can use? Premium location and walking distance to the beach! Ocean Palms is a 1/5th deeded fractional ownership property allowing each owner 10 weeks of use per year on a calendar rotation of 2 weeks back to back 5 times annually. Management by the Westin Oceanfront Resort & Spa allows use of the hotel amenities, fitness center, oceanfront pool complex, beach access and resort shuttle. A great golf & tennis package is included with ownership. This wonderful 2 bedroom/2 bath designer furnished 1st floor Captiva floor plan has 1300 htd sq ft, a spacious back deck, and overlooks the back pool area. Onsite open house/model villa open daily.

14 Wimbledon Court Unit 135-5, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$2,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511359 MLS
Owner is also selling Week 17 (Unit 2900) and is open to offering a discounted price if both weeks are purchased together - an excellent opportunity to enjoy two consecutive weeks in paradise! Experience the relaxed sophistication of Hilton Head Island during deeded Week 16, ideally positioned in the last week of April, when spring is in full bloom and the island is at its most beautiful. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of Hilton Head's most sought-after communities. This desirable end-unit villa, located next to the pool, offers added privacy, extra natural light, and exceptional convenience. Overlooking the lush fairways of the golf course, it provides peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and the vibrant coastal arts and culture that make Sea Pines so special. Imagine beginning your mornings with refreshing ocean breezes and serene golf course views before setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. Late April offers warm, comfortable temperatures, colorful spring blooms, and ideal conditions for beach walks, outdoor dining, dolphin cruises, tennis, and all that Sea Pines has to offer-before the peak summer crowds arrive. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep. With the option to purchase the adjoining Week 17 at a discounted package price, this is a rare opportunity to enjoy two consecutive weeks in one of Hilton Head Island's premier vacation destinations.

70 Lighthouse Road Unit 2896, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$1,900
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511357 MLS
Owner is also selling Week 16 (Unit 2896) and is open to offering a discounted price if both weeks are purchased together-an excellent opportunity to enjoy two consecutive weeks in paradise! Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 17, ideally positioned in the first week of May when the island is at its springtime best. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. This desirable villa overlooks the lush fairways of the golf course, providing peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with refreshing ocean breezes and serene golf course vistas, then setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. May's comfortable temperatures and blooming landscapes create the perfect setting for beach walks, outdoor dining, dolphin cruises, and all that Sea Pines has to offer-without the crowds of peak summer. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep. With the option to purchase the adjoining Week 17 at a discounted package price, this is a rare opportunity to enjoy two consecutive weeks in one of Hilton Head Island's premier vacation destinations.

70 Lighthouse Road Unit 2900, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$284,000
3 Beds ⋅ 3 Baths ⋅ 1,254 SqFt. ⋅ HILTONHEAD-511188 MLS
Great Value You Don't Want to Miss! Finding a 3-bedroom, 3-bath home on Hilton Head Island at this price is becoming increasingly rare. Offering approximately 1,250 square feet, this free-standing condo in The Gatherings presents an outstanding opportunity as a full-time residence, vacation getaway, or investment property. Well-maintained and move-in-ready, featuring a bright, inviting living room and a cheerful eat-in kitchen that serves as the heart of the home. The first floor offers two comfortable bedrooms, two full baths, and a conveniently located laundry closet. Upstairs, you'll find a spacious private suite complete with a large bedroom, full bath, and generous walk-in closet-perfect as a primary retreat or private guest suite. Step outside to enjoy the private deck or take advantage of the community pool located directly across the street. The Gatherings is an established neighborhood with a welcoming atmosphere, longtime residents, and an exceptionally convenient location offering easy access to both Hilton Head Island and Bluffton. Select restaurants and shopping are within near distance, adding to the convenience of everyday island living.If you've been searching for an affordable Hilton Head address without sacrificing space, comfort, or convenience, this home deserves a place at the top of your list.

36 Wee Road Unit 36, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,645,000
3 Beds ⋅ 3 Baths ⋅ 1,762 SqFt. ⋅ HILTONHEAD-511199 MLS
Wake up to the Atlantic at Captain's Walk - a rare, direct-oceanfront villa that's almost never open to tour. Six steps off your private back porch put you on the beach path, with sand underfoot in under two minutes. As a first-floor corner residence, it offers true single-level living - no elevators, no stairs to your door - looking straight out to the ocean. Inside, roughly 1,762 square feet of bright, open-concept living opens to the view. The updated kitchen features quartz countertops, custom cabinetry, and stainless-steel appliances, flowing into spacious dining and living areas with a sleeper sofa for extra guests, plus in-unit washer and dryer. All three bedrooms are en suite - a primary with a king and ocean views, a second with two queens, and a third with a king - comfortably sleeping eight. Just outside your door: an oceanfront pool, children's pool, cabana, expansive sundecks, a grilling area, and a boardwalk to the sand. Ownership unlocks all of Palmetto Dunes - an 11-mile lagoon system, three championship golf courses, a tennis and pickleball center, and the seasonal Dunes Buggy to Shelter Cove Marina's shops and dining. Offered fully turnkey, it's income-ready from day one - an established rental with a 10/10 guest rating across 28 reviews. And with owner pet privileges for up to two dogs, it's a rarity among resort rental villas. Homes like this rarely come open - see it while you can.

21 Ocean Lane Unit 401, Hilton Head Island

Listing courtesy of Charter One Realty.

$5,000
3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511193 MLS
Experience luxury ownership in Indigo Run's exclusive Owners Club. This deeded equity share home offers 27 days of annual use in a beautifully furnished 3BR/3BA residence of approximately 2,000 square feet. Designed for effortless "lock-and-leave" living, the home features dual primary suites, an open floor plan, a fully equipped kitchen, and a relaxing porch for enjoying the Lowcountry lifestyle.The all-inclusive annual ownership fee of $4,900 covers property taxes, insurance, utilities, housekeeping, and all interior and exterior maintenance. Owners enjoy exceptional amenities including a clubhouse, fitness center, resort-style pool, hot tubs, tennis, and unlimited golf at Indigo Run's Golden Bear Golf Club plus seven additional courses (cart fees apply). Exchange opportunities through RCI and Interval International provide access to vacation destinations worldwide. Enjoy luxury Hilton Head Island ownership without the responsibilities of full-time homeownership.

32 Aberdeen Court, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$375,000
4 Beds ⋅ 3 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-511055 MLS
Perfectly positioned between Hilton Head Island and Bluffton, this rare detached home in The Gatherings offers the best of both worlds - single-family living with the ease of a condo association's worry-free exterior maintenance. Nestled on a quiet cul-de-sac, this elevated 4-bedroom home is one of only a few true four-bedroom properties in the community, making it a highly sought-after find in the Hilton Head Island real estate market. Enjoy serene marsh views right from home, plus a 1-car garage and additional storage space beneath. Residents of The Gatherings enjoy access to community amenities, including a pool and tennis courts, all just minutes from the shopping, dining, beaches, and golf that make Hilton Head Island and Bluffton, SC, two of the most desirable places to live on the East Coast.

19 Pine Burr E Road Unit 16, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$1,350
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511051 MLS
Enjoy the peaceful elegance of Hilton Head Island during deeded Week 45, perfectly timed for the crisp beauty of late autumn and, in many years, the Thanksgiving holiday. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most coveted settings. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and the island's rich coastal arts and culture scene.Imagine beginning your mornings with cool ocean breezes and uncrowded beaches, biking beneath majestic live oaks draped in Spanish moss, or spending leisurely afternoons on award-winning fairways before gathering with family and friends for memorable holiday meals or spectacular waterfront sunsets. Whether you're seeking a relaxing seasonal escape, an active golf retreat, or a warm-weather destination for Thanksgiving celebrations, Week 45 offers the perfect blend of tranquility, natural beauty, and island charm; all with the flexibility and convenience of deeded ownership.

70 Lighthouse Road Unit 2875, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$45,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-510746 MLS
Located in the closest building to the beach, The Westin, and Golf. Ocean Palms @ The Westin Resort & Spa | 2BR/2BA Fractional Ownership. This 1st floor designer-furnished 2 bedroom, 2 bath Sanibel townhouse located in building 1, rarely available, offers 1,328 sqft, w/private porch and screened in porch overlooking a wildlife filled lagoon, the Barony Golf Course, & lush Spanish Moss draped trees. Ocean Palms is a 1/5th deeded fractional ownership community, giving each owner 10 weeks of use per year - structured as 5 rotations of 2 consecutive weeks - on a simple calendar system that's fair, predictable, & flexible.Ownership comes fully loaded. Access to the full Westin Oceanfront Resort & Spa: oceanfront pools, gym, beach access, resort shuttle, free golf/tennis/pickleball daily. The Westin's professional management team handles everything - you just show up.Walking distance to the beach. Model open Monday-Saturday, noon to 5pm. Sundays by appointment.It won't last. New furnishings being installed this year.

14 Wimbledon Court Unit 101-1, Hilton Head Island

Listing courtesy of NorthGroup Real Estate LLC.

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.