Summerland Key sits around Mile Marker 24 in the Lower Keys, between Cudjoe Key to the south and Ramrod Key to the north. It has a established permanent residential community alongside second-home owners drawn to the relaxed Lower Keys lifestyle and easy boating access to both the Atlantic and Gulf.
One feature that sets Summerland apart: a private grass airstrip runs through the community, and some homes have direct taxiway access -- a genuine draw for fly-in buyers. Beyond that, the island offers the usual Lower Keys mix of canalfront, open-water, and non-waterfront properties, which accounts for the wide range in asking prices.
Experience the pinnacle of Florida Keys waterfront living in this exceptional 3-bedroom, 3-bathroom oceanfront estate offering breathtaking open water views, deep-water d...
Welcome to an exceptional waterfront property on Summerland Key, where three contiguous canal-front lots create an expansive Florida Keys retreat. Situated on a combined ...
Experience the PINNACLE of luxury waterfront living at this exceptional oceanfront residence on prestigious Flagship Drive. Completely reimagined with uncompromising atte...
Welcome to Summerland Key Cove! This beautifully home is perfectly situated on a deep-water canal with excellent boating access. Boaters will appreciate the new 17,000-lb...
Elevated Coastal Living in Breezeswept Beach Estates. Skip the typical vacation rentals & step into a home designed specifically for the genuine Florida Keys lifestyle. S...
Welcome to Pink Sands, a Glenn Gray-designed waterfront retreat where the vibrant colors and laid-back elegance of the Bahamas meet the timeless beauty of the Florida Key...
Move-in ready and beautifully updated! This charming 2-bedroom, 2-bath home offers approximately 960 square feet of comfortable living space in the desirable Summerland K...
Beach House Paradise in Summerland Key. Nestled in one of the Lower Keys' most desirable oceanside communities, this exceptional oceanfront retreat offers the perfect ble...
Bring your water toys & experience island living in this newly built waterfront home in Summerland Key. The residence offers 3 bedrooms 2 bathrooms spacious modern desig...
Well-maintained 3-bedroom, 2-bath home offering 1,120 square feet of comfortable living space in a small, well-kept community in Summerland Key. This home is in excellent...
Discover one of the Florida Keys' most extraordinary private island retreats. Encompassing 9.69 acres of pristine tropical landscape, Howell Key offers an unparalleled op...
DOUBLE the Lot. DOUBLE the Waterfront. Endless Possibilities. Positioned on a rare spacious double lot near the Summerland Key airport, this waterfront property is tai...
OVERSIZED GARAGE. WATERFRONT LIVING. Bring the boat, tackle, dive gear, kayaks, and all the Keys toys-there's room for everything at 706 Caribbean Drive East. With can...
Built for the offshore lifestyle, this exceptional Summerland Key waterfront home blends luxury coastal living with the kind of boating access serious anglers dream about...
Waterfront duplex located on a wide, deep boating canal with excellent boating access and 60 ft. of dockage, split between both units, offering approximately 30 ft. per s...
Pilots, this is a great opportunity to build your dream home with access to Summerland Key's private airport, and enjoy access to the Blanche Bergin Marina Park, complete...
OCEANFRONT , POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, jus...
Purchase this deep draft canal front LOT in Summerland Key in the Florida Keys. The building permit is in-process for a 3 bedroom/ 2 bath stilted single family residence...
Rare opportunity to own a canal-front home directly on the private Summerland Cove Airport--where you can fly in, dock up, and be on open water in minutes. This solid ...
Skip the lengthy ROGO allocation process! Market Rate Transferable ROGO Exemption (TRE) available. One (1) lot transferable development right to use for residential co...
Elevated COASTAL LIVING meets clean, modern design in this beautifully remodeled 2BD/2BA stilted home in sought-after Summerland Key. Designed with a striking monochromat...
Sailor's Dream -- waterfront living at its best! Beautifully maintained tropical home with 3 bedrooms and 2 baths on a deep, wide canal with spectacular open-water views ...
Rare opportunity in the heart of Summerland Key, two contiguous waterfront lots totaling 12,000 SF in the SC (Suburban Commercial) zoning district. Offering over 120 feet...
Rare opportunity in the heart of Summerland Key, two contiguous waterfront lots totaling 12,000 SF in the SC (Suburban Commercial) zoning district. Offering over 120 feet...
PILOTS and BOATERS will love this! Tucked away in the heart of Summerland Key, this charming 2-bedroom, 2-bath home captures the essence of true Florida Keys living. Surr...
High quality concrete 3/2 in Summerland Cove. One of the best boating communities in the lower Keys for deep water, aqua blue canal water, and oceanside access with no br...
A stunning location with all attributes geared to the view of the beautiful open bay of Summerland Cove. This OCEANFRONT 3 bedroom 3 bath home is on the market for the fi...
Excellent opportunity to build your dream in paradise. This 6,140 sq foot lot with 70.65 ft. of water frontage has a beautiful open water and ocean view. This is the last...
An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity—an off-grid sanctuary offering complete privacy, turquoise wat...
Offshore island 4 acre lot in the heart of the Great White Heron Wildlife refuge is suitable for temporary camping and exploration. World class flats fishing for bonefish...
A Turnkey Boater's Paradise with Direct Open Water Access! Nestled on a crystal-clear, 60-foot-wide canal, this exceptional waterfront property sits just 600 feet from op...
Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residen...
Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residen...
Priced at Current appraised value, this 3-bedroom, 3-bath concrete fortress on deep water canal (5' draft) is located in the highly sought-after Summerland Cove with quic...
This stately concrete home has all the best of everything on one of the best boating areas in the Lower Keys Thís home is being offered completely furnished with electro...
Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residen...
Welcome to a truly unique aviation property in the heart of Summerland Key! Located at the end of the exclusive Summerland Key airstrip on a 12,425 sq. ft. double lot, th...
Hard to find a home in a Park like setting with a boat ramp right out the back door! 3 bedrooms 2 full baths and open living space. Summerland key cove is just 25 miles ...
Discover island living in this charming 3-bedroom, 1-bath canal-front home located in desirable Summerland Key, featuring fabulous sunset views. Set on a 60-foot-wide dee...

Jim Signor: 305-394-4449