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Group DiNenna is a top 10 buyer-focused team in the Hilton Head Island real estate sales area. This includes Hilton Head Island, Sun City, Bluffton, Hardeeville, and the Okatie area. We specialize in helping buyers new to the area identify their ideal community.

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Our search engine offers every real estate listing currently for sale in Hilton Head Island, Bluffton, Okatie, and Sun City areas.

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A Note About Community Access

Looking for a home in the Hilton Head, Bluffton, Sun City, and Okatie area presents a unique challenge. Many of the communities can only be accessed by owners, guests, and registered businesses. What does that mean for you?Well, as a future homeowner you’ll be excited to know that many communities offer 24/7 security. As a prospective homeowner, that means you need someone to help you gain access to the communities.

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Latest Hilton Head & Bluffton Listings For Sale

$8,900,000

2 Beds ⋅ 3 Baths ⋅ 2,845 SqFt. ⋅ HILTONHEAD-514253 MLS

Acreage within the gates of this community is rare, land at this scale rarely comes to market. Set within the Equestrian Neighborhood of Longfield, 65 Laurel Oak Bay Road offers 37.3 acres of Lowcountry landscape in one of the world's most celebrated private communities. This is land with a future as grand as its setting. Envision a world-class equestrian estate, pastures, stables, and barns unfolding across open ground. How about a multigenerational family retreat, where additional residences and outbuildings can take shape around a shared landscape, each with room to breathe and land to call its own. The canvas is here, most of the infrastructure to build upon it is already in place. At its heart stands a three-year-old custom cottage of approximately 2,845 square feet, ready to be lived in today while the larger vision unfolds. Thoughtfully sited to overlook a private pond, it offers the rare combination of immediate comfort and long horizon: move in now, dream in decades. Life in Palmetto Bluff is defined by amenities few communities on earth can match. The Montage resort and spa anchors the community, alongside the May River Golf Club, the Longfield Stables equestrian center, a marina on the May River, and Wilson Village with its dining, shops, and gathering places, all connected by miles of trails through maritime forest, marsh, and riverfront. It is a world unto itself, and a way of life that cannot be replicated. Defined by preservation, by water and marsh and maritime forest. To own 37.3 acres within it is to hold something enduring, a legacy property for a family, a horseman, or a visionary who understands that land like this, in a community like this, is the rarest luxury of all.

65 Laurel Oak Bay Road, Bluffton

Listing courtesy of SERHANT.

$2,195,000

5 Beds ⋅ 5 Baths ⋅ 4,000 SqFt. ⋅ HILTONHEAD-514248 MLS

Discover an exceptional opportunity to build a custom H2 Builders home in the prestigious gated community of Indigo Run. Situated on a beautiful .44-acre lagoon homesite, this thoughtfully designed 4,000 SF residence offers a flexible floor plan with up to 5 bedrooms, 5 baths, and a 2-car garage with golf cart bay. The main level features a spacious primary suite, two additional bedrooms, one designed as a study/office, an inviting great room with coffered ceilings, eat-in kitchen, and screened outdoor living area overlooking the lagoon. Upstairs, a media room, guest accommodations, and versatile bonus space provide flexibility for family and guests. With architectural plans preliminarily approved by the Indigo Run ARB, buyers can bypass approximately 6-10 months of planning and design while retaining the opportunity to personalize selections and finishes. Offered at $2,195,000 as a complete homesite and new construction package. The $389,000 homesite must be purchased and closed on separately prior to construction. Construction with H2 Builders is required.

46 Branford Lane, Hilton Head Island

Listing courtesy of Hilton Head Real Estate Partners.

$1,795,000

5 Beds ⋅ 6 Baths ⋅ 3,783 SqFt. ⋅ HILTONHEAD-514137 MLS

Bright, spacious, and designed for the Hilton Head lifestyle, this beautiful 5-bedroom, 5.5-bath home sits in the sought-after gated community of Indigo Run. Filled with natural light, the home offers an inviting atmosphere with plenty of room for both everyday living and entertaining. Outdoors, a large in-ground pool and hot tub create the perfect setting for relaxing or gathering with friends and family. Indigo Run offers a wonderful combination of privacy, natural beauty, and convenience, with scenic leisure trails, two Jack Nicklaus-designed golf courses, and golf-cart-friendly living. Ideally situated near Hilton Head's beaches, shopping, dining, and everyday conveniences, this home offers the best of Lowcountry living.

69 Wedgefield Drive, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$449,900

2 Beds ⋅ 2 Baths ⋅ 1,978 SqFt. ⋅ HILTONHEAD-513487 MLS

Meticulously cared for and exceptionally well maintained, this Franklin Whitney model in Sun City Hilton Head is sure to impress! VERY gently lived in, this home offers an abundance of storage with an incredible 11 closets! The spacious sunroom is a standout feature, with multiple sliding glass doors that beautifully bring the outdoors in. Updates and improvements are plentiful, including newer windows, a newer hot water heater, hurricane shutters and six-inch seamless gutters. The kitchen features a newer Bosch dishwasher, electric range, microwave, & garbage disposal, plus a refrigerator just two years old. The oversized garage offers even more functionality with a utility sink, man door, and storage cabinets that convey. Additional garage upgrades include a newer garage screen, keypad, steel garage door replaced in 2024, LiftMaster Wi-Fi opener and new garage spring. Situated on a quiet cul-de-sac street, the home also boasts newer landscaping and a wonderful setting. If you are looking for a lovingly maintained home with an abundance of storage, a fabulous sunroom and a long list of improvements, this one deserves a look! Sun City Hilton Head has just completed a $50 million expansion. This new phase features a state-of-the-art amenity center, & a 41,000-42,000+ sq ft Clubhouse. A Two-Story Fitness Center has 15,000+ sq. ft. facility with an indoor walking track & a multi-sports court. There is a15,000 sq. ft. pool, pool-side food bar, Baja sun deck, & poolside cabanas + Indoor lap pool, outdoor & indoor courts, outdoor & indoor tennis courts and so much more! In addition to the new expansion, residents have access to the established world-class infrastructure. Three 18-hole golf courses, 4 outdoor & 3 indoor pools. Town Center consists of 45-acres featuring social halls, a 540-seat performing arts theater, & 3 onsite restaurants. There are over 200 chartered clubs, a 20-acre fishing lake, woodshop, art studios, & miles of walking trails. Live your best retirement life!

1 Humbert Court, Bluffton

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$435,000

HILTONHEAD-514229 MLS

A Rare Development Opportunity in the Heart of Old Town Bluffton!Position your next investment in one of the Lowcountry's most sought-after and rapidly growing markets. Ideally situated in the heart of Old Town Bluffton, this exceptional parcel offers a rare opportunity to secure land in one of the area's most desirable and historically significant locations.Located directly across from Martin Family Park, the property enjoys outstanding visibility, walkability, and proximity to the charm, shopping, dining, and attractions that make Old Town Bluffton so special. With developable land becoming increasingly scarce in this highly coveted historic district, opportunities like this are truly hard to find.The property has received Planning Commission approval for a 2.5-story building encompassing approximately 3,000+ square feet, offering an exciting head start for your next development vision. Whether you envision a commercial investment, residential project, or a thoughtfully designed mixed-use opportunity, the possibilities are compelling.An added bonus: the adjoining Lot 67 is also available for purchase, creating an opportunity to expand your footprint and maximize the potential of this exceptional location.Don't miss your chance to be part of the continued growth and revitalization of Old Town Bluffton! Public water and sewer are available.

69 Boundary Street, Bluffton

Listing courtesy of Maxey Blackstream Christie's International Real Estate.

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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.