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Summerland Key Real Estate - Lower Florida Keys

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.

Neighborhoods on Summerland Key

  • Cruikshank Island
  • Dobie's Subdivision
  • Knock-Em-Down Keys
  • Snug Harbor Subdivision
  • Summerland Beach
  • Summerland Cove Isle
  • Summerland Estates
  • Summerland Key Cove

Summerland Key Homes For Sale

25361 1st St, Summerland image
25361 1st St, Summerland $3,500,000

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...

  • 3 Beds
  • 3 Baths
  • 620742 MLS
1044 Lagoon Dr, Summerland image
1044 Lagoon Dr, Summerland $2,900,000

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 ...

  • 4 Beds
  • 2 Baths
  • 620644 MLS
1046 Flagship Dr, Summerland image
1046 Flagship Dr, Summerland $5,200,000

Experience the PINNACLE of luxury waterfront living at this exceptional oceanfront residence on prestigious Flagship Drive. Completely reimagined with uncompromising atte...

  • 4 Beds
  • 4 Baths
  • 620606 MLS
24347 W Caribbean Dr, Summerland image
24347 W Caribbean Dr, Summerland $1,199,000 ▼

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...

  • 3 Beds
  • 2 Baths
  • 617789 MLS
673 Indies Rd, Summerland image
673 Indies Rd, Summerland $989,000

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...

  • 3 Beds
  • 2 Baths
  • 620596 MLS
23950 Overseas Hwy, Summerland image
23950 Overseas Hwy, Summerland $3,300,000

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...

  • 5 Beds
  • 4 Baths
  • 620578 MLS
24740 Park Dr, Summerland image
24740 Park Dr, Summerland $675,000

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...

  • 2 Beds
  • 2 Baths
  • 620563 MLS
361 Ave D, Summerland image
361 Ave D, Summerland $3,100,000

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...

  • 2 Beds
  • 3 Baths
  • 620532 MLS
23940 Overseas Hwy, Summerland image
23940 Overseas Hwy, Summerland $899,000

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...

  • 3 Beds
  • 2 Baths
  • 620512 MLS
96 John St, Summerland image
96 John St, Summerland $550,800

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...

  • 3 Beds
  • 2 Baths
  • 620439 MLS
Howell Ky, Summerland image
Howell Ky, Summerland $16,900,000

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...

  • 5 Beds
  • 4 Baths
  • 620413 MLS
466 W Shore Dr, Summerland image
466 W Shore Dr, Summerland $1,300,000

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...

  • 2 Beds
  • 2 Baths
  • 620321 MLS
706 E Caribbean Dr, Summerland image
706 E Caribbean Dr, Summerland $1,185,000

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...

  • 3 Beds
  • 2 Baths
  • 620281 MLS
848 E Caribbean Dr, Summerland image
848 E Caribbean Dr, Summerland $2,246,000

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...

  • 3 Beds
  • 2 Baths
  • 620177 MLS
596 W Shore Dr, Summerland image
596 W Shore Dr, Summerland $998,000

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...

  • 5 Beds
  • 3 Baths
  • 620094 MLS
290 46th St, Summerland image
290 46th St, Summerland $415,000 ▼

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...

  • 2 Beds
  • 1 Baths
  • 620034 MLS
414 E Caribbean Dr, Summerland image
414 E Caribbean Dr, Summerland $3,495,000

OCEANFRONT , POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, jus...

  • 4 Beds
  • 4 Baths
  • 620024 MLS
24285 W Caribbean Dr, Summerland image
24285 W Caribbean Dr, Summerland $395,000

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...

  • 620006 MLS
324 S Airport Dr, Summerland image
324 S Airport Dr, Summerland $849,999 ▼

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 ...

  • 2 Beds
  • 2 Baths
  • 619732 MLS
319 Shore, Not Provided image
319 Shore, Not Provided $180,000

Skip the lengthy ROGO allocation process! Market Rate Transferable ROGO Exemption (TRE) available. One (1) lot transferable development right to use for residential co...

  • 619543 MLS
637 E Caribbean Dr, Summerland image
637 E Caribbean Dr, Summerland $1,200,000

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...

  • 2 Beds
  • 2 Baths
  • 619455 MLS
24225 W Caribbean Dr, Summerland image
24225 W Caribbean Dr, Summerland $999,000 ▼

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 ...

  • 3 Beds
  • 2 Baths
  • 619447 MLS
24764 Overseas Hwy, Summerland image
24764 Overseas Hwy, Summerland $899,000

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...

  • 619387 MLS
24774 Overseas Hwy, Summerland image
24774 Overseas Hwy, Summerland $899,000

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...

  • 619383 MLS
667 E Caribbean Dr, Summerland image
667 E Caribbean Dr, Summerland $1,100,000

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...

  • 2 Beds
  • 2 Baths
  • 619318 MLS
937 Gulf Dr, Summerland image
937 Gulf Dr, Summerland $2,220,000 ▼

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...

  • 3 Beds
  • 2 Baths
  • 619294 MLS
24348 Caribbean Dr, Summerland image
24348 Caribbean Dr, Summerland $3,295,000 ▼

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...

  • 3 Beds
  • 3 Baths
  • 619204 MLS
00000 Lagoon Dr, Summerland image
00000 Lagoon Dr, Summerland $1,450,000

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...

  • 618940 MLS
Melody, Summerland image
Melody, Summerland $7,000,000

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...

  • 3 Beds
  • 4 Baths
  • 616249 MLS
Lot 8 Lot 8 Little Knockemdown Ky Unit AKA Parcel 23, Summerland image
Lot 8 Lot 8 Little Knockemdown Ky Unit AKA Parcel 23, Summerland $85,000

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...

  • 615890 MLS
1331 Hudgins Dr, Summerland image
1331 Hudgins Dr, Summerland $1,050,000 ▼

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...

  • 2 Beds
  • 2 Baths
  • 618229 MLS
231 E Shore Dr Unit 5, Summerland image
231 E Shore Dr Unit 5, Summerland $4,400,000

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...

  • 5 Beds
  • 6 Baths
  • 616704 MLS
231 E Shore Dr Unit 1, Summerland image
231 E Shore Dr Unit 1, Summerland $3,995,900

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...

  • 5 Beds
  • 6 Baths
  • 616700 MLS
887 Bay Dr, Summerland image
887 Bay Dr, Summerland $1,595,000

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...

  • 3 Beds
  • 3 Baths
  • 618272 MLS
860 Lagoon Dr, Summerland image
860 Lagoon Dr, Summerland $1,950,000

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...

  • 3 Beds
  • 3 Baths
  • 616756 MLS
231 E Shore Dr Unit 4, Summerland image
231 E Shore Dr Unit 4, Summerland $4,375,000

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...

  • 5 Beds
  • 6 Baths
  • 616703 MLS
195 W Shore Dr, Summerland image
195 W Shore Dr, Summerland $799,000 ▼

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...

  • 3 Beds
  • 2 Baths
  • 617998 MLS
24840 Park Dr, Summerland image
24840 Park Dr, Summerland $950,000 ▼

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 ...

  • 3 Beds
  • 2 Baths
  • 617590 MLS
360 W Shore Dr, Summerland image
360 W Shore Dr, Summerland $749,500

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...

  • 3 Beds
  • 1 Baths
  • 617776 MLS

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