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 paradise is renowned for its stunning natural beauty, vibrant marine life, and laid-back island lifestyle. With its crystal-clear turquoise waters, lush tropical landscapes, and gentle ocean breezes, Summerland Key offers an idyllic setting for those seeking a tranquil escape from the hustle and bustle of everyday life.

As you explore this charming community, you'll discover a wealth of outdoor activities, from world-class fishing and snorkeling to kayaking and paddleboarding. The island's proximity to the Florida Keys National Marine Sanctuary ensures that residents can enjoy some of the best diving and water sports in the country, all just moments from their doorstep. With its friendly neighbors and tight-knit community spirit, Summerland Key is not just a place to live; it’s a place to thrive.

For those looking to make Summerland Key their home, there are a variety of homes for sale that cater to diverse tastes and preferences. Whether you're dreaming of a waterfront property with private dock access, a cozy cottage surrounded by lush greenery, or a luxurious estate with breathtaking ocean views, Summerland Key has something for everyone. Each home is a unique opportunity to embrace the island lifestyle and create lasting memories in this tropical paradise.

Discover the charm and beauty of Summerland Key, where your dream home awaits. Embrace the island life and start your journey today!

Newest Summerland Key Homes for Sale

$899,000
2 Beds ⋅ 1 Baths ⋅ 621091 MLS
Tropical Waterfront Living in the Florida Keys! Welcome to 24923 Park Drive in beautiful Summerland Key, where laid back Florida Keys living meets ultimate waterfront lifestyle. This charming canal-front property offers an opportunity to create your own paradise in one of the Keys' most desirable boating communities. Positioned along a wide protected canal, the property features direct waterfront access to both Ocean & Gulf, 60 ft. concrete seawall, two boat lifts, private dockage. Making it ideal for boating, fishing, kayaking, and enjoying everything the Florida Keys has to offer. The spacious large open grassy yard offers room to personalize the outside space with a pool or outdoor kitchen, tiki, fire-pit or resort style entertaining oasis. This existing home offers a wonderful opportunity for a buyer looking to renovate, expand, or create a custom island retreat. With its metal roof, single level layout, tropical surroundings and exceptional waterfront setting this property provides the perfect foundation for a Florida Keys getaway, full-time residence, or investment opportunity. Bring your vision and transform this waterfront gem into your own private Keys paradise. Florida Keys Heritage trail for biking & walking close by. Summerland Key Private Air strip walking distance away.

24923 Park Dr, Summerland
$1,300,000
2 Beds ⋅ 2 Baths ⋅ 620934 MLS
Summerland Key Cove -- Come by Sea or by Plane A unique opportunity in Summerland Key Cove offering both canal-front living and access to the community's private airport. Whether your Florida Keys lifestyle revolves around boating, flying, fishing, diving, or simply enjoying the water, this property offers a combination that is increasingly hard to find. Built in 1982, this 1,240 sq. ft. concrete block home features 2 bedrooms plus a versatile bonus room that can serve as a guest room, home office, gym, TV room, or additional living space. An approximately 400 sq. ft. screened room overlooking the canal adds substantial outdoor living space. Some major improvements have already been completed, including a 2022 metal roof, 2023 impact windows and doors on the upper level, and updated central A/C in 2020. Connected to central sewer. One of the property's standout features is the approximately 1,240 sq. ft. airplane hangar height of 9ft. Hard-to-find amenity in the Florida Keys--plus approximately 400 sq. ft. of additional storage and a concrete driveway. On the water, the property offers approximately 60 feet of concrete seawall on a 60-foot-wide canal, along with a davit. Two canal exits provide access to Kemp Channel, opening the way to both Atlantic Ocean and Gulf-side boating for fishing, diving, exploring, and enjoying the surrounding Keys waters. Located in an improved subdivision on a Tier III lot in AE-10 flood zone. Fencing is permitted. Access to the Summerland Key Cove airport and marina is available through membership. The home is currently tenant occupied with pets; advance notice is required for showings. NO tresspassing. Rented

486 S Airport Dr, Summerland
$799,000
3 Beds ⋅ 1 Baths ⋅ 620897 MLS
Welcome to the Mango Cottage on Summerland Key! Tucked away on a quiet dead-end street, this 3 bedroom, 1 bath canal front CBS home combines the laid back Florida Keys lifestyle with excellent boating access and a few features you simply don't find everywhere. Surrounded by multiple mature fruit trees, including several mango trees! This property has a distinctly tropical feel from the moment you arrive. Inside, the home offers an open floor plan, a bright kitchen with a skylight, and a spacious Florida room featuring a cool Hemingway style bar, the perfect spot to mix a drink, entertain friends, or unwind after a day on the water. An good sized laundry and utility room provides plenty of additional storage and functionality. CBS construction and a post-Irma metal roof add to the home's appeal. Out back, the pavered yard creates a low maintenance outdoor living space with plenty of room to add a pool. A 60-foot concrete dock puts your boat right outside your door, with excellent access from Summerland Key and marine fuel and ice conveniently located just down the canal. The location also puts you close to Ace Hardware, fantastic local restaurants, and everyday conveniences while still enjoying the peace of a tucked away residential dead end street. Aviation enthusiasts will appreciate the neighborhood's unique private airstrip setting, offering the potential for a true fly in/fly out Keys lifestyle. With tropical fruit trees, great boating, a concrete dock, generous outdoor space, and plenty of classic Keys character, Mango Cottage is ready for its next chapter.

27 N Lake Dr, Summerland
$3,500,000
3 Beds ⋅ 3 Baths ⋅ 620742 MLS
Experience the pinnacle of Florida Keys waterfront living in this exceptional 3-bedroom, 3-bathroom oceanfront estate offering breathtaking open water views, deep-water dockage, and sophisticated modern design throughout. Thoughtfully designed for luxury, comfort, and entertaining, this stunning residence seamlessly blends elegant architecture with the beauty of its coastal surroundings. The open-concept living area is filled with natural light from expansive arched windows and walls of glass, creating a seamless connection between the interior and the sparkling Atlantic. The chef's kitchen features a dramatic waterfall quartz island, premium stainless steel appliances, custom high-gloss cabinetry, designer lighting, and generous space for gathering with family and friends. The spectacular primary suite spans over 1,000 square feet, creating a true private retreat. The spa-inspired primary bath is a showpiece featuring striking blue agate-inspired porcelain walls, an oversized walk-in rainfall shower, freestanding soaking tub, dual vanities with custom wood countertops, and an expansive custom walk-in closet with illuminated cabinetry. Two spacious guest bedrooms and beautifully appointed bathrooms provide exceptional accommodations for family and visitors. Throughout the home, luxury finishes include oversized porcelain tile flooring, custom ceiling details, recessed LED lighting, contemporary glass accents, and designer fixtures that elevate every space. Step outside to your private waterfront oasis where tropical landscaping, a sandy beach area, and a deep-water dock provide direct access to world-class boating, fishing, paddleboarding, kayaking, and the crystal-clear waters of the Atlantic Ocean. Enjoy spectacular sunrises and endless ocean breezes from multiple outdoor living areas designed to embrace the Florida Keys lifestyle.

25361 1st St, Summerland
$1,199,000
3 Beds ⋅ 2 Baths ⋅ 617789 MLS
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 boat lift and a quick ride to Looe Key, American Shoal, and the Adolf Bush wreck. The 1232 sq ft home sits on a 6,000 sq ft lot and features hurricane-impact windows, offering peace of mind and energy efficiency. The home has been tastefully remodeled within the last two years, including new kitchen and new bathrooms. Additional major upgrades include 2-year-old A/C the roof is just 4 years old. Bright, inviting, this home is ideal for enjoying the relaxed island lifestyle with world-class boating, fishing, and diving right at your doorstep. The supply lift will make it easy to transfer items to the second floor.

24347 W Caribbean Dr, Summerland
$2,999,000
5 Beds ⋅ 4 Baths ⋅ 620578 MLS
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 Keys. Recognizable by its signature pink façade and blue metal roof, this exceptional Summerland Key residence captures the spirit of island living while offering the quality, comfort, and peace of mind of modern CBS construction. Set along a protected canal with 125 feet of concrete dockage, two boat lifts, and direct deep-water access to both the Atlantic Ocean and Gulf of Mexico, this waterfront home is perfectly positioned for effortless days on the water, from world-class fishing and diving to sunset cruises and sandbar adventures. Impact windows and doors and thoughtfully designed indoor-outdoor living spaces create a home that is as durable as it is inviting. Sweeping open ocean views from the main living level and third-story observation deck provide the perfect backdrop for sunrise mornings and starlit evenings. A charming detached guest cottage connected by a covered breezeway creates a private compound ideal for hosting family and friends. The oversized homesite offers exceptional flexibility with ample room to add a custom pool, expand outdoor entertaining areas, or further enhance the property to suit your vision. Just 35 minutes from Key West, Pink Sands feels as though it belongs on Harbour Island while remaining firmly rooted in the authentic charm of Summerland Key. Blending Bahamian-inspired architecture with the confidence of newer CBS construction, exceptional boat dockage, direct ocean and Gulf access, and endless opportunities for future customization, this is a rare opportunity to own a distinctive Florida Keys waterfront home. Minutes from Looe Key Reef, Content Keys, and the backcountry flats, this exceptional location offers unparalleled access to some of the Florida Keys' most sought-after boating, fishing, diving, and paddleboarding destinations right from your private dock

23950 Overseas Hwy, Summerland
$649,000
2 Beds ⋅ 2 Baths ⋅ 620563 MLS
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 Key Airport neighborhood. The recently updated interior features an inviting open floor plan and a stunning kitchen complete with quartz countertops, modern cabinetry, and updated appliances. The bright living and dining areas create a welcoming space for everyday living and entertaining. Step outside from the dining area to a private patio, perfect for enjoying your morning coffee, outdoor dining, or relaxing in the tropical breeze. The seamless connection between the living room, dining area, and patio creates an ideal indoor-outdoor Florida Keys lifestyle. Community boat ramp available for easy water access. Located in the desirable Summerland Key Airport community and just minutes from world-class boating, fishing, waterfront dining, and all the recreational opportunities the Lower Florida Keys have to offer, this home is perfect as a full-time residence, vacation getaway, or investment property. Don't miss this opportunity to own an updated slice of paradise in one of the Florida Keys' most desirable communities!

24740 Park Dr, Summerland
$3,100,000
2 Beds ⋅ 3 Baths ⋅ 620532 MLS
Beach House Paradise in Summerland Key. Nestled in one of the Lower Keys' most desirable oceanside communities, this exceptional oceanfront retreat offers the perfect blend of luxury, privacy, and island living. A charming thatched-covered lanai and custom bamboo-etched glass doors welcome you into an open-concept floor plan where floor to ceiling windows frame breathtaking Atlantic Ocean views. The spacious living area flows effortlessly to an expansive waterfront terrace overlooking the pool, creating the ultimate indoor-outdoor lifestyle. Designed for entertaining, the lower level features a custom tiki-style bar, outdoor cooking area, hot tub, and multiple gathering spaces. Relax by the resort-style pool, unwind on your private sandy beach beneath the swaying palms, and enjoy the unparalleled beauty of oceanfront living. Located just minutes is Summerland Key's private airstrip, world class boating, fishing, diving and the renowned Looe Key reef, this exceptional property offers the very best of the Florida Keys lifestyle. 361 Avenue D is a rare opportunity to own your own slice of paradise.

361 Ave D, Summerland
$899,000
3 Beds ⋅ 2 Baths ⋅ 620512 MLS
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 design & trim. A durable metal roof, Hardie-board siding, impact windows and doors. Enjoy relaxing or entertaining on the covered porch, step out on the composite dock and be on the open ocean or Gulf in minutes, perfect for boating, fishing and sunset cruses. Keys biking trail steps away. Great local restaurants, convenient local island grocery store. Private Summerland Key Airstrip. Centrally located between Marathon and Key West, this property combines modern construction, waterfront convenience, low maintenance and easy access to both Keys' amenities. Ideal for a vacation retreat or full time home. Schedule your private showing today.

23940 Overseas Hwy, Summerland
$535,000
3 Beds ⋅ 2 Baths ⋅ 620439 MLS
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 condition, offers ample parking, and provides a wonderful opportunity for affordable homeownership in the Lower Keys. Subject to affordable housing deed restrictions.

96 John St, Summerland
$16,900,000
5 Beds ⋅ 4 Baths ⋅ 620413 MLS
Discover one of the Florida Keys' most extraordinary private island retreats. Encompassing 9.69 acres of pristine tropical landscape, Howell Key offers an unparalleled opportunity to own an off-grid luxury island with two building rights, allowing for one additional residence, surrounded by breathtaking open water views from sunrise to sunset. Designed for those who value privacy, adventure, and refined coastal living, the island features groomed trails, resort-style pool, sandy beach, pickleball court, chicken coop, pasture, and expansive barn. At the heart of the island sits a beautifully crafted 5-bedroom, 4-bath residence encompassing 3,352 sq. ft. Cathedral ceilings, elegant coastal interiors, and expansive gathering spaces create a warm yet sophisticated atmosphere, while walls of impact-rated glass invite natural light and panoramic water views. The layout comfortably accommodates family and guests with an attached primary suite featuring a generous walk-in closet. A separate guest wing, accessed via a breezeway, includes its own living room, breakfast bar, and two private bedrooms. Wander the groomed trails, relax by the saltwater pool, launch kayaks from the sandy beach, enjoy pickleball, or watch the sunset from your dock. Built for resilience and efficiency, the home features SIP construction, Hardie Board siding, a standing seam metal roof, impact windows and doors, whole-house reverse osmosis water filtration, and an off-grid solar power system. Elevated approximately 10 feet above base flood elevation, the property offers sustainability and peace of mind. The purchase includes a barge, golf cart, tractor, and a private mainland lot for car storage. Howell Key offers a private island lifestyle few will ever have the opportunity to experience.

Howell Ky, Summerland
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 620321 MLS
DOUBLE the Lot. DOUBLE the Waterfront. Endless Possibilities. Positioned on a rare spacious double lot near the Summerland Key airport, this waterfront property is tailor-made for boating enthusiasts and aviation lovers alike. Featuring 120 feet of concrete seawall on a desirable flow-through canal, you'll enjoy quick access to open water and some of the Lower Keys' best fishing, diving, and cruising grounds. Afterwards, sit under the tiki and watch the world go by. The ground-level home exhibits a Keys charm with polished terrazzo floors and a relaxed, welcoming feel. Outside, ample parking provides room for boats, trailers, RVs, and guests. Inside, a unique electric train display serves as a nod to the historic Overseas Railroad that once connected the Keys. A rare opportunity to enjoy the classic Florida Keys lifestyle with room to spread out, easy boating access, and the convenience of nearby aviation amenities. Bring your big boats to this deep water canal - no bridges to the Atlantic Ocean. Plane tie downs are located in the driveway. For additional airport info - see summerlandkeyairport.com

466 W Shore Dr, Summerland
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