Most of the properties in the Florida Keys peninsula are either on the bay / gulf side or on the ocean side of the island. The following Waterfront Summerland Key homes for sale below are on the gulf side / bay side.
NEW WATERFRONT LISTING! MOTIVATED SELLER! Beautifully updated waterfront home with breathtaking views and 40 seawall. All major improvements are complete including roof, HVAC,impact windows, door, new kitchen and appliances with gas range, electrical panel,tankless water heater,and lower level kitchenette. DIRECT boating access to Niles Channel. The downstairs is a LEGAL nonconforming grandfathered space with 2 bedrooms. This property has a strong rental history with optional bookings through March of 2026. The home is owned by a FL licensed real estate broker.
Paradise awaits you in this Florida Keys waterfront home! Located on Summerland Key, this 2-bedroom, 2-bathroom, canal front home is a perfect blend of comfort and coastal charm. Boaters will love the full Length 40 ft concrete seawall on a wide deep-water canal. The home has quick access to Niles Channel and both the Gulf and Atlantic sides for great fishing and diving. The securely fenced yard adds privacy and a secure place for children and pets, as well as a great outside space to entertain and enjoy the day. Make your appointment to come see this today!
Seize this rare opportunity to own a prime working waterfront property with exceptional Highway visibility. This unique offering includes two waterfront buildings located at 24931 & 24933 Overseas Highway in Summerland Key, each with separate water, electric, and sewer connections for added flexibility. Situated on a 10,673 SF lot, the property features a 813 SF building, a 1,152 SF building, and a 192 SF utility/storage building for additional space. Additionally, the property includes a private boat ramp, providing convenient water access. Whether youre looking to expand or open a business or invest in a high-exposure location located on the water, this property offers incredible potential. Buyer to verify property rights.
Welcome to Howell Key! This unique island oasis, purchased in 2010, was developed as an off-grid, private family retreat for a multi-generational remote getaway. Now, this breathtaking 9.69-acre turnkey opportunity is on the market, inviting you to live your offshore island dream or invest in a one-of-a-kind vacation rental experience. Situated off mile marker 25 in Summerland Key, Florida Keys, Howell Key is just a 5-minute boat ride from your private masterpiece. With direct access to both the Atlantic Ocean and the Gulf of Mexico, your watersport dreams can come true daily. Proximity by boat is close to Looe Key National Marine Sanctuary, many sand bars, and the famous 5-star Little Palm Island Resort and Spa. This inviting island sanctuary features dockage accommodating vessels up to 50 feet and an electric gate leading to the marina lagoon. The energy-efficient, immaculate five-bedroom, four-bath home boasts a saltwater pool, exposed beam ceilings, travertine tile throughout, and SIPS panel technology construction. Additional structures on Howell Key include a guest house, garage, animal pens, pickleball court, tiki hut with beach, helipad, and finger dock with a covered sitting area. Plus, a second ROGO-exempt permit allows for constructing another dream home. This is a completely turnkey, fully furnished property that provides a peaceful, tropical escape from the ordinary. This purchase includes a Shore Station Lot completely fenced in to leave vehicles and has a 58 seawall to accommodate your personal ferry. Full list of amenities included in the documents tab.