Summerland Key Florida homes for sale starting at Fifty Thousand Dollars

$21,900,000 - Summerland Key, FL

0 Howell Key Summerland Key, FL - 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.

$8,455,000 - Summerland Key, FL

1151 Ocean Drive Summerland Key, FL - TROPHY OCEANFRONT ESTATE! This one-of-a-kind luxury estate offers an unparalleled coastal lifestyle on 120 feet of prime oceanfront. Designed for the discerning buyer, this breathtaking property combines elegance with the ultimate boating experience.The centerpiece of this estate is the 120,000 lb boat lift, capable of accommodating a 70 ft yacht--a rare find in the Keys. The property also features a private mooring buoy, 2 additional boat lifts, and a private boat basin equipped with a compressor-operated bubbler system to keep seaweed at bay. With exclusive bay bottom rights, it's a true boater's paradise, offering the perfect space to keep your vessels safe. Inside, the estate is a showcase of luxury. It features 5 spacious bedrooms, an exercise room, 4 full baths, and 2 half baths, all thoughtfully designed for comfort and style. The main living area boasts vaulted ceilings and opens onto a massive tiled patio surrounding a raised pool and spa. This elevated design allows for a seamless flow between indoor and outdoor living, complete with a covered bar area for entertaining and breathtaking panoramic views of the Atlantic Ocean and Little Palm Island.The chef's kitchen is equipped with high-end appliances and an open layout, perfect for grand gatherings. A separate dining area is adjacent to the kitchen and living area. There is a laundry room and the 5th bedroom is currently set up as an office for added flexibility. The single-car garage provides peace of mind for your vehicle, large storage area under the house.Set on an expansive 37,400 sq. ft. lot, this estate is beautifully landscaped, resembling a resort with lush tropical gardens. A desalination plant and backup generator ensure complete self-sufficiency, while the private beach offers your own slice of paradise. This is a trophy property with unmatched boating capabilities and luxurious living. Don't miss your chance! Schedule your private tour today! Video tour https://tinyurl.com/1151Ocean

$5,992,000 - Summerland Key, FL

220 E Caribbean Drive Summerland Key, FL - Experience unparalleled luxury in this Brand New 2025 Custom Built Smart Home. 6,128 SQ FT concrete-constructed oceanfront home, situated in prestigious Summerland Key. With 90 feet of ocean frontage and breathtaking southwest views of the Atlantic Ocean, this home is the ultimate retreat for those seeking elegance, comfort, and adventure.The third floor is the heart of this home, featuring an infinity-edge pool and spa that frame magnificent sunsets and ocean vistas. Seamlessly blending indoor and outdoor living, the expansive entertainment areas promise unforgettable gatherings. This magnificent custom home offers five spacious bedrooms with ensuite bathrooms, including a dual primary suite that can serve as a 6th bedroom or an office. Additional features include: A state-of-the-art sound proof home theater room with Marantz 11.2 surround sound, 16' screen, and 8K JVC projector.Custom Canadian birch cabinetry and Thermador WiFi-enabled appliances throughout. A boater's Paradise  designed for water enthusiasts, the property features: Two boat lifts (25,000 LB and 10,000 LB), A 6' x 90' concrete dock with two tiers for jet skis and kayaks. Deepwater access with a 90' wide, 28' deep channel leading directly to the Atlantic and Gulf.Proximity to world-class snorkeling and diving at Looe Key Coral Reef.Unmatched durability and sustanibility, built to exceed 180 MPH wind loads, solid concrete floors, walls & roof.This home includes: All high-impact Marvin & Euro-Wall windows and doors.70 solar panels (34.5 KW of power) and 4 Tesla Power Walls 57.6KW powers home.Three on-demand hot water systems and a 10,000-gallon rainwater cistern.Exceptional features include; Private elevator servicing all three levels. RV/Boat garage (15' W x 50' D x 14' H) with 50 AMP/220V service. Tesla charging station. WiFi-enabled smart home systems, including AC, pool pumps, and appliances. See Documents Tab / Possible Seller Financing.

$5,500,000 - Summerland Key, FL

481 E Shore Drive Summerland Key, FL - Exceptional Investment Opportunity in the Lower Florida Keys!Owner and private financing are available. This is one of the very few vacation rental properties licensed for daily, weekly, or monthly rentals. Boasting an impressive occupancy rate and generating up to $400,000 annually, this property offers stress-free, passive income in Summerland Key, a premier location.Discover a rare gem in the heart of the Lower Keys! Recently remodeled to perfection, this luxurious three-bedroom beach house includes a sunroom with a palatial ocean view, currently used as a fourth bedroom. Just 20 miles from vibrant Key West, this coastal retreat features a private natural beach, breathtaking ocean views, and access to a private airport for island residents less than two blocks from the property.Don't miss this unparalleled investment opportunity!Please note that I have a personal interest in this property.

$3,199,000 - Summerland Key, FL

23941 Henry Street Summerland Key, FL - Oceanfront Oasis - A Rare Coastal Retreat! Wake up to breathtaking Sunrises over the Atlantic and unwind with stunning Sunsets each evening in this Custom-built 3 story Solid CBS & Concrete home Nestled on an exclusive private street with only four homes, this island-inspired escape offers the perfect blend of luxury, Tropical charm, and Panoramic Ocean views.Step inside to an open-concept design, that showcases soaring arched windows, oversized glass doors, and covered porches, allowing natural light to flood the home while maximizing the stunning water views.The chef's kitchen is a dream for entertainers, featuring stainless steel appliances, tall custom wood cabinetry, and generous counter space. This home offers two spacious bedrooms, two bathrooms, plus a separate office, ideal for remote work or additional space. Lower level provides a formal foryer entrance, with large storage room, man cave and two+ car garage.Outdoors, indulge in your private lagoon-style pool with a cascading waterfall and hot tub, all surrounded by lush mature tropical landscaping, swaying palm trees, and a variety of fruit trees. Relax under the poolside tiki hut or under the palms by the ocean, entertain on the landscaped travertine-paved grounds, creating the ultimate tropical outdoor retreat.For boating enthusiasts, the 62-ft concrete dock offers quick, direct access to both the Ocean and Gulf. Complete with a New 17K boat lift, three additional boat davits, with protected dockage, this property also includes a Private Beach & 300 feet of bay bottom ownership--a unique find!Additional features include a large two-car CBS drive-through garage, a separate storage room man cave and a welcoming foyer entrance.This one-of-a-kind oceanfront sanctuary is truly a boater's paradise and a tropical haven--offering the best of coastal living.Seller is a Florida RE agent.

$2,599,000 - Summerland Key, FL

943 Flagship Drive Summerland Key, FL - Spectacular Open Ocean Views Across from Open Water! Rare opportunity to own this coastal jewel located on the most prestigious and sought-after Flagship Drive in the exclusive Summerland Cove Isle neighborhood on Summerland Key. This beautifully designed CBS 3-bedroom, 2-bathroom canal-front pool home offers breathtaking, unobstructed open ocean views that will captivate you from sunrise to sunset. Situated on an oversized 10,080 sq. ft. lot, larger than most in the area, this waterfront retreat is perfectly positioned across from open water, allowing you to enjoy mesmerizing sunset cocktails from the open deck with panoramic sunset views in one direction and exquisite moonrises in the other--all in one evening. The property boasts a concrete dock, a boat ramp for launching jet skis, small boats, paddleboards, and kayaks, as well as two boat lifts each 14k lb on a, deep, flow-through canal with quick and easy deep-water access to the Atlantic Ocean--a true boater's dream. Inside, the home features a modern coastal feel, inviting open-plan living, dining, and kitchen area with soaring vaulted ceilings, creating an airy and light-filled atmosphere. The split floor plan offers privacy, with the primary suite situated in a separate wing. This serene retreat also includes a flexible bonus space that can be closed off and used as a sitting area, office, gym, or nursery, with access to a covered deck. The exterior is equally impressive, featuring a sparkling concrete pool with canal-front views, a garage within a 1088 sqft storage area, and a carport offering ample space for boat storage or the option to transform it into a spacious covered entertaining area. Located near a local airstrip for small planes, this rare property is a haven for those seeking both luxury and convenience in a prime Keys location.Don't miss this rare opportunity to own a coastal jewel with ocean views and deep-water boating access. Insurances $12k Video https://tinyurl.com/4ff3aan8

$1,999,900 - Summerland Key, FL

1165 Lagoon Drive Summerland Key, FL - Exceptional waterfront pool home in Summerland Key! This beautifully updated 2156sqft concrete home is located in the desirable neighborhood of Summerland Cove, known for its incredible boating access, deep-water flow through canals and close location to Key West (just 24 miles). Enjoy the ocean and lagoon views from the kitchen, living room, dining room, loft and screened patio, or from the 64' long concrete dock! Dock comes equipped with boat davits, fish cleaning station with water and swim ladder. With no rear neighbors there is plenty of privacy to lounge by the pool (has a pool heater/chiller), throw in a paddle board or kayak and cruise the lagoon or take advantage of the incredible boating/ fishing that Summerland has to offer with quick access to the Atlantic Ocean and the Gulf! This newly updated home includes 2 bedrooms on the main level, 600 sqft loft upstairs used for a 3rd bedroom and 2 bathrooms, brand new kitchen with quartz counters and stainless appliances, impact windows and new impact sliders, 2016 metal roof, newer 263 sqft garage/storage and plenty of room for parking with a higher than usual 12' clearance under the house, able to park boats, trailers and/or RV (and yes there are RV hook ups!)

$1,999,900 - Summerland Key, FL

$1,850,000 - Summerland Key, FL

1323 Hudgins Drive Summerland Key, FL - Discover your slice of paradise with this beautifully remodeled 2-bedroom, 2-bathroom home, perfectly situated in the desirable Snug Harbor subdivision of Summerland Key, just 30 minutes from the vibrant atmosphere of Key West. This exceptional property boasts a solid concrete block construction, upgraded with hurricane impact doors and windows and a metal roof.Step inside to experience the airy ambiance with soaring ceilings and abundant natural light. The modern, fully furnished kitchen is a culinary dream, featuring contemporary finishes and ample space for entertaining. Each ensuite bedroom offers generous walk-in closets and spacious bathrooms, ensuring a comfortable retreat for family and guests alike.Enjoy year-round outdoor living with a full wrap-around porch overlooking the expansive yard and wide canal with straight shot to open water. Unwind in the soothing hot tub, perfect for relaxation after a day of adventures. The oversized yard provides plenty of room for vehicles and all your recreational toys, RVs, and trailers, along with an additional great entertainment area with additional space that adds versatility for your needs.After a fun-filled day on the water, dock your boat at the impressive 100 ft. concrete sea wall, equipped with boat davits for easy on off access. unwind with a cocktail in hand at your charming outdoor Chickee Hut, all while soaking in serene waterfront views and relax atmosphere.This property offers an idyllic coastal living experience. With rentals allowed (with restrictions) and minimum rental days set at 28, this home poses a fantastic investment opportunity as well. For those interested, furnishings can be purchased separately, offering the option to move in and start enjoying your new home/investment immediatelyExperience the serenity of Summerland Key living today!

$1,749,000 - Summerland Key, FL

25081 Overseas Highway Summerland Key, FL - So many opportunities at this 3 Bedroom 2 Bath canal front property located in the Commercial Fishing District boasting 240' of road frontage with excellent highway visibility and 240' of waterfront with full concrete dock and seawall, just one property in from the open water. Located in the Special Fishing District on Summerland Key where home businesses including commercial fishing and boat mechanics are allowed. Excellent canal dockage with quick and easy access to the gulf and ocean. The newly remodeled coastal style home offers impact windows, metal roof, vinyl plank flooring, open kitchen with white shaker cabinetry and quartz counters, new baths and a split floor plan. The 3 adjacent lots are cleared and buildable, offering full concrete docks. Commercial Fishing Zoning allows for many uses.

Summerland Key, Florida listings for sale

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