Featured Listings · Hilton Head Island, Bluffton & Okatie, SC

Our Current Listings

Real homes, real inventory, updated the second something new hits the market.

Nicky Gleason Real Estate · Luxury Homes of Hilton Head

This list is live, straight from the MLS. New listings show up the moment they go live, and sold ones drop off on their own. This is my team's current inventory, and I'm glad to walk you through any of it myself, from what a listing photo doesn't show to how a home actually lives day to day.

For Buyers

Looking for a Home?

I work closely with my team on everything represented here, so I can help you get past the photos, whether that's porch orientation, POA fees, or anything else the listing sheet leaves out.

  • Private tours on your schedule
  • Early word on listings before they hit the market
  • Real advice on communities, not just square footage
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For Sellers

Thinking About Selling?

Every home on this page started with a conversation like this one. I build a plan around your house, not a template I use for everyone.

  • Free home valuation, no strings attached
  • A pricing and marketing plan built for your home
  • Professional photos and real exposure
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Local Expertise · Credentials

Boutique Service, Real Credentials

I've been selling real estate on Hilton Head Island, Bluffton, and Okatie for 8+ years, and I'm currently brokered by Luxury Homes of Hilton Head. I keep my client list small on purpose, so every home and every client gets my full attention.

CLHMS · RENE · ABR · SRS · PSA · 2025 WCR Lowcountry Member of the Year

Frequently Asked

A Few Common Questions

How often is this list updated?

Constantly. It's tied straight to the MLS, so new listings show up the moment they go live and sold or pending homes drop off on their own.

Does this cover all of Hilton Head, Bluffton, and Okatie?

Yes. Everything my team and I currently represent across the Lowcountry lives on this one page.

Can I see a home before it's publicly listed?

Sometimes. I often hear about a home before it's fully marketed. Reach out and tell me what you're looking for, and I'll keep an eye out.

What does a home valuation cost?

Nothing. It's free, no strings attached, and gives you a real number to work with.

What makes your marketing different?

No templates. I build a strategy for every listing, with professional photos and pricing set around that specific home and buyer pool.

Whether you're buying or selling, lot position, pricing, and timing matter more than the listing photos suggest. That's what I'm here for.

I don't sell homes. I make matches.

Talk to Nicky

Information deemed reliable but not guaranteed. Listing availability, pricing, and terms are subject to change and should be independently verified. Equal Housing Opportunity.

Featured Properties

8 Dinghy, Hilton Head Island
$6,795,000
7 Beds ⋅ 6 Baths ⋅ 4,000 SqFt. ⋅ HILTONHEAD-512572 MLS
Where Pаlmetto Duneѕ mеetѕ thе ѕeа, уou get the sunrise bеforе anyone else even reaches the beach. 8 Dinghy is true direct oceanfront in Palmetto Dunes, with the timeless coastal style built for the way Lowcountry living is supposed to feel. The Atlantic is already outside your door, no walk required. Fully remodeled top to bottom with new fixtures, appliances, furniture, kitchen and baths with an additional laundry added to the second floor and the expansion of the screen porch are all exceptional features of this 4,000 square foot home. Seven bedrooms and five and a half baths give you room to bring the whole family without anyone getting in anyone else's way. The gourmet kitchen has two refrigerators built for real entertaining, and the oceanfront pool, large deck, and screened porch turn every meal into an event. The owner turned the garage into a game room during rental season for added family fun and the multiple outdoor living spaces give everyone incredible places to enjoy their time while on Hilton Head Island. A gated path leads directly to the stretch of wide soft sandy beaches and is located just far enough away from the crowded beach areas but yet close enough for a short walk to the heart of Palmetto Dunes. Golf, tennis, and resort amenities are part of everyday life here. Direct oceanfront rarely comes to market on Hilton Head Island. This one is available now, but likely not for long. Owner willing to finance 50% for 5yrs at a reasonable rate.

8 Dinghy, Hilton Head Island

Listing courtesy of Luxury Homes of Hilton Head.

15 Dewberry Lane, Hilton Head Island
$1,495,000
5 Beds ⋅ 3 Baths ⋅ 2,504 SqFt. ⋅ HILTONHEAD-512460 MLS
Some hοmes givе уou а рlаcе tο stay in Sea Ρinеs. 15 Dewberry gives you a reason to stay in. This five-bedroom home in Greenwood Forest pairs the Sea Pines lifestyle with the kind of amenities that make the house itself part of the vacation. And yes, the bikes come with the house. THE PUTTING GREEN: A professionally designed three-hole green spans 35 to 38 feet with an 11 stimp rating and real break, good for a morning warm-up or one more round after dinner. THE HANGOUT: A separate in-law suite with its own kitchenette turned wet bar, ice maker included. One of the home's five bedrooms currently serves as the suite's living room, and flexes just as easily into a bunk room when more sleeping space is needed. THE SPACE: Brazilian hardwood floors, a tongue and groove ceiling, quartz counters, and GE Cafe appliances run throughout the single story home, with new flooring added in the bedrooms. A Carolina room with a daybed and porch swing gives everyone one more place to land. THE NEIGHBORHOOD: Greenwood Forest is one of the few pockets of Sea Pines with its own community pool, tennis and pickleball, and a playground, a short distance from the Shops at Sea Pines and Beach Trolley access through a wooded community path. Easy distance to either HarbourTown or the Beach! Already an active vacation rental, the home has a confirmed booking of 91 nights for 2027 alone, worth more than $19,000, a sign of how much demand a house like this can hold.

15 Dewberry Lane, Hilton Head Island

Listing courtesy of Luxury Homes of Hilton Head.

125 Shipyard Drive Unit 124, Hilton Head Island
$695,000
2 Beds ⋅ 3 Baths ⋅ 1,400 SqFt. ⋅ HILTONHEAD-508081 MLS
Ideallу posіtіonеd јuѕt off thе bеach path in Shiрyаrd, this updated villa offers easy access to both the sand and pool, along with a strong history as a short-term rental. Set in the closest building to the beach within the villa complex, the location offers a distinct advantage for both owners and guests. This beautifully updated villa, renovated within the past five years, is a proven short-term rental with a solid track record. The interior features quality upgrades throughout, including custom tile showers, updated flooring, and a well-designed kitchen and living area that balance style and functionality. Step outside to a spacious rear deck that opens directly to the beach path, offering quick and easy access to the sand. The community pool is just steps away, creating an ideal setup for vacationers seeking both beach and pool access. Shipyard is a gated, 800-acre community located in the heart of Hilton Head's south end, known for its convenient access by bike to beaches, golf, tennis, and nearby amenities. Residents and guests enjoy direct beach access via the Shipyard Beach Club, as well as access to Van Der Meer Tennis Center and Shipyard Golf Club's 27 holes. The community's central location near Coligny makes it especially attractive for both personal use and rental demand. An excellent opportunity for investors or second-home buyers seeking a turn-key property with proven income potential in one of Hilton Head's most established resort communities.

125 Shipyard Drive Unit 124, Hilton Head Island

Listing courtesy of Luxury Homes of Hilton Head.

70 Paddle Boat Lane Unit 411C, Hilton Head Island
$359,900
1 Beds ⋅ 2 Baths ⋅ 1,028 SqFt. ⋅ HILTONHEAD-510189 MLS
Limitеd Time Gеt $10,000 tοwardѕ уοur clοѕing costs! Nothіng to rеnovate or update, just show up and enjoy the convenience of being close to everything. Somebody put real thought into every corner of this Penthouse unit at Palmetto Bay Marina, and it shows the moment you walk in. The kitchen is the first thing people talk about: large quartz island with, white maple shaker cabinets, GE Profile stainless appliances, blue-green handmade tile backsplash, exposed wood beam, and pendant lights that actually look incredible. It's genuinely a beautiful kitchen. This property has two full baths that have been completely remodeled with one being on the main floor. The primary bath upstairs has double quartz vanities, a frameless glass shower with Carrara-style tile, and matte black fixtures throughout. The full bath downstairs is its own thing entirely: a vessel sink carved from natural stone on a live-edge wood top, cedar shiplap wall, corrugated metal ceiling. Guests notice it every time. The bonus room has a Murphy bed already installed with built-in shelving, so it works as an office, a gym, or a guest room depending on the week. Views of Broad Creek and Palmetto Bay Marina from the secluded outside balcony whcih has new rails and flooring. Elevator gives ease of access and you can enjoy the fabulous pool or grill anc chill on the waterfront deck area. Close to waterfront dining, the marina, and everything that makes this part of Hilton Head worth owning.This is a top-floor penthouse unit which means more windows, more light, and more quiet enjoyment. Turn-key and move-in ready.

70 Paddle Boat Lane Unit 411C, Hilton Head Island

Listing courtesy of Luxury Homes of Hilton Head.

399 Pineland Estates Road, Pineland
$283,900
2 Beds ⋅ 1 Baths ⋅ 1,180 SqFt. ⋅ HILTONHEAD-500607 MLS
Set on 3.46 open acres, 399 Pineland Estates offers the space and freedom to create the life you want, on your terms. Beautiful, fully-cleared land includes fruit trees (plums, peaches, and two bananas), abundant elderberry bushes, a chicken coop, and a fenced garden. With no HOA and minimal restrictions, you're free to grow your own food, build a workshop, keep animals, store your toys, or simply enjoy the freedom and peace of your own land. The 2-bedroom, 1-bath ranch home features low-maintenance LVP flooring, a one-car garage, and a new whole-house water purification system for clean, fresh water at every tap. Located just 20 minutes to downtown Ridgeland, an hour from both Hilton Head's famous beaches and historic Beaufort, and less than two from Charleston, this generous property offers a winning combination of rural tranquility, personal freedom, relative convenience, and value. Welcome home.

399 Pineland Estates Road, Pineland

Listing courtesy of Luxury Homes of Hilton Head.

663 William Hilton Parkway Unit 2101, Hilton Head Island
$251,500
2 Beds ⋅ 2 Baths ⋅ 843 SqFt. ⋅ HILTONHEAD-505142 MLS
Excеptionаl іnveѕtmеnt οpрοrtunity in the heart of Ηiltοn Head. This beautifully maintained villa offers everything today's vacation renters are searching for. Perfectly positioned mere steps away from all the resorts considerable amenities. Whether visitors come for championship golf, world-class tennis, water sports, or simply to relax by the ocean, they'll appreciate the convenience of being close to it all. Walkability and easy beach access are top priorities for vacation renters-and this villa delivers. Modern finishes and coastal-inspired decor create an inviting retreat that guests are eager to return to year after year. The kitchen features updated appliances and ample prep space. Spacious bedrooms and well-appointed baths provide comfort for families and groups, increasing rental appeal and revenue potential. With Hilton Head Island's established reputation as a premier vacation destination and a history of steady visitor demand, this villa represents a compelling opportunity for investors seeking both lifestyle enjoyment and income potential. Whether you self-manage or use a rental program, this is the type of property that stands out on line, books consistently, and keeps guests coming back. Capitalize on location, condition, and amenities (the three pillars of successful vacation rental investing) all in one exceptional Hilton Head Island condo.

663 William Hilton Parkway Unit 2101, Hilton Head Island

Listing courtesy of Luxury Homes of Hilton Head.

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