Summerland Key Homes for Sale

Summerland Key Homes for Sale

Welcome to Summerland Key, a hidden gem nestled in the heart of the Florida Keys, within Monroe County. This enchanting island community is renowned for its stunning coastal views, vibrant marine life, and laid-back lifestyle that embodies the true essence of island living. With its tropical climate, Summerland Key offers year-round sunshine and a warm, inviting atmosphere that beckons both residents and visitors alike.

Summerland Key is not just a picturesque paradise; it’s a thriving community where neighbors become friends and life moves at a leisurely pace. The area boasts an array of outdoor activities, from kayaking through crystal-clear waters to fishing in the abundant Gulf Stream. The nearby nature preserves and parks provide ample opportunities for hiking, birdwatching, and enjoying the breathtaking scenery that surrounds this idyllic locale.

For those looking to make Summerland Key their home, a variety of charming properties are available for sale. Whether you’re in search of a cozy waterfront cottage, a modern family home, or a luxurious estate with panoramic ocean views, the real estate market here offers something for everyone. Many homes feature private docks, expansive outdoor spaces, and easy access to the best fishing and boating spots in the Keys.

Embrace the opportunity to live in a place where every day feels like a vacation. Discover your dream home in Summerland Key and immerse yourself in the beauty and serenity of island life. Your slice of paradise awaits!

Newest Summerland Key Homes for Sale

$1,775,000
4 Beds ⋅ 4 Baths ⋅ A12042729 MLS
Brand new waterfront in the Keys, built for you from the ground up. This is a preconstruction home in Cutthroat Harbor Estates. You buy now and it gets built for you, delivered turnkey. Picture it: your boat at the private dock on approx. 102 ft of canal seawall, a pool and jacuzzi below, coffee on the rooftop deck. Elevated 4 bed, 4 bath, outdoor kitchen, solar and efficient systems, brand new and low maintenance. And the best part? The permit is already secured, so your home gets built now instead of years from now.

193 Galleon Lane, Summerland Key
$1,100,000
3 Beds ⋅ 2 Baths ⋅ A12018522 MLS
Welcome to your slice of paradise! Down in Big Torch Key, you'll feel a sense of solitude, satisfaction and serenity. Minimal, if any, noise or light pollution on this Key; look up at night and you will see stars you've never seen before! Quick and easy access to the Atlantic and Gulf of America, plenty of fishing spots and places to relax on the water without those big upper Key crowds. The adjacent vacant lot for sale is owned by the same person - a perfect opportunity to purchase two lots and transform into one! With this dock size already at 65', imagine how many more boats you could dock with both lots!Vacant land MLS#A12018646**Water photos at the end are for reference to show what the water looks like at the end of the canal. This home does not directly have this view**

4276 Dorn Road, Summerland Key
$1,050,000
3 Beds ⋅ 3 Baths ⋅ A11986220 MLS
Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly found in the Keys. The elevated concrete home features a spacious layout, multiple balconies, and abundant natural light throughout. With kitchen and bathrooms ready for renovation, this is the perfect canvas to create a custom waterfront residence or maximize value through a strategic upgrade.Enjoy ample outdoor space with room for expansion, a pool, additional storage or enhanced landscaping - making this property uniquely versatile for both end-users and investors.Ideally located within close proximity to Key West, offering convenient access to world class dining, entertainment and boating, while still enjoying the privacy and tranquility of canal front living.

27403 Antigua Lane, Summerland Key
$895,000
3 Beds ⋅ 2 Baths ⋅ A11998100 MLS
Offered in the highly sought-after Jolly Roger Estates, this beautifully maintained, one-owner canal-front home is just 11 years old and truly move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence offers three bedrooms and two bathrooms, enhanced by refined finishes including crown molding, tray ceilings, tile showers, and a bright, open-concept living space ideal for coastal living. Built for both comfort and peace of mind, the home features a metal roof installed in 2018 along with impact-rated windows and doors throughout. Enjoy added privacy and nightly sunset views over the protected salt marsh directly across the street—an unspoiled natural backdrop that will never be developed. Boaters will appreciate the free-flowing, clear-water canal with excellent access to both the ocean and the bay. The private dock with a 7,000-lb side-lift boat elevator makes heading out for fishing, diving, or sunset cruises effortless. The spacious lot offers a large driveway, double covered parking, and ample room for boat trailers and additional vehicles. Downstairs, a full concrete pad and enclosed angler's room provide the perfect space for storing fishing gear, dive equipment, and all your island toys. Located near mile marker 28.5, Jolly Roger Estates is a peaceful, palm-lined waterfront community on the Atlantic side of Little Torch Key, offering direct access to Pine Channel and world-class boating, fishing, and diving at nearby Looe Key Reef.

437 Pirates Road, Summerland Key
$4,250,000
5 Beds ⋅ 6 Baths ⋅ R11113452 MLS ⋅ The Seven Palms - A Key West Oasis BLDG.
Welcome home to an exceptional new-construction residence in a private, gated community offering resort-style amenities, a boat slip and nightly rental opportunities. Conveniently located next to Summerland Key Airport, this fully upgraded home features a private elevator, a stunning infinity pool overlooking the water and an expansive rooftop deck perfect for enjoying breathtaking Florida Keys sunsets. Only have two homes remaining.

231 E Shore Drive Unit Unit 2, Summerland Key
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