Summerland Key Real Estate

Summerland Key Real Estate

Welcome to Summerland Key, a picturesque gem nestled in the heart of the Florida Keys, Monroe County. This enchanting island paradise offers a unique blend of laid-back island living, stunning natural beauty, and a vibrant community spirit. With its pristine waters, lush landscapes, and a warm tropical climate, Summerland Key is the perfect destination for those seeking a tranquil escape or a new place to call home.

Summerland Key is renowned for its breathtaking sunsets and abundant outdoor activities. Whether you’re an avid fisherman, a boating enthusiast, or simply someone who enjoys the serenity of nature, this island has something for everyone. The surrounding waters are teeming with marine life, making it a prime location for snorkeling and diving. Explore the stunning coral reefs or take a leisurely kayak ride through the mangroves, immersing yourself in the vibrant ecosystem that thrives here.

The community of Summerland Key is tight-knit and welcoming, with a variety of local events and activities that foster connections among residents. From farmers' markets to art festivals, there’s always something happening that brings people together. Additionally, the island’s proximity to Key West means that the vibrant nightlife, dining, and cultural experiences of the mainland are just a short drive away.

Real estate opportunities in Summerland Key range from charming waterfront homes to spacious lots ready for your dream build. Whether you’re looking for a vacation retreat or a permanent residence, this idyllic island offers a lifestyle that is both relaxing and fulfilling. Embrace the beauty of island living in Summerland Key, where every day feels like a vacation!

Newest Listings in Summerland Key

836 Gulf Dr, Summerland
$1,975,000
3 Beds ⋅ 3 Baths ⋅ 621887 MLS
GULF DRIVE GETAWAY - Beautifully Remodeled Florida Keys Living Enjoy the best of Florida Keys living in this beautifully remodeled home situated at the end of a cul-de-sac, ideally located, and just minutes from open-water access. Flow through canals with 2 boat lifts make this a boater's dream property. Offering far more than meets the eye, this property features an abundance of bonus space, providing flexibility for a home office, hobbies, guests, entertaining, or whatever your Keys lifestyle calls for. The thoughtfully updated interior offers a fresh, inviting feel, while impact windows provide added peace of mind. Step outside to enjoy your private pool, perfect for relaxing after a day on the water. A garage adds valuable storage and convenience for a vehicle and golf cart, boating gear, and all the extras that come with island living. Beautifully updated, wonderfully versatile, and close to open water, this is a special opportunity to make the Florida Keys lifestyle your own!

836 Gulf Dr, Summerland
312 E Caribbean Dr, Summerland
$2,400,000
3 Beds ⋅ 2 Baths ⋅ 621795 MLS
OPEN WATER VIEWS. ENDLESS POSSIBILITIES. YOUR SUMMERLAND KEY WATERFRONT RETREAT. Some properties are all about the location - and this is one of them. Set along the open water in sought-after Summerland Key, this well-maintained 3-bedroom, 2-bath concrete home offers incredible unobstructed views, easy boating access, and the opportunity to create your own vision of Florida Keys living. Outside, the open-water setting takes center stage, with expansive views that bring the beauty of the Florida Keys into everyday life. The concrete construction offers a solid foundation, while the fenced property and electric entry gate provide added convenience. From the covered screened balcony upstairs, you can soak in the beauty and catch spectacular sunset views. The existing interior retains its original character, providing a wonderful starting point for buyers ready to reimagine the space and make it their own. Whether your dream is a modern coastal retreat, a relaxed waterfront getaway, or a personal island escape, the possibilities are here. For boaters, waterfront living is about more than a view - it's about getting out on the water and enjoying everything the Keys have to offer. Here, the setting provides the backdrop for days spent exploring, fishing, lobstering, and returning home to spectacular open-water scenery. Straight access to the Atlantic and Gulf waters. Opportunities to secure an open-water property in Summerland Key and transform it to suit your own style are increasingly appealing. Bring your vision, embrace the location, and create something special in the Florida Keys. The views are already here. The next chapter is yours to create.

312 E Caribbean Dr, Summerland
86 S Airport Dr, Summerland
$2,195,000
3 Beds ⋅ 3 Baths ⋅ 621715 MLS
RARE RUNWAY-TO-REEF LIVING Fly in. Boat out. Live the Florida Keys lifestyle few properties can offer. At 86 S Airport Drive on Summerland Key, aviation and boating come together in one exceptional property. This CBS 3-bedroom, 3-bath home sits directly on the runway and alongside a flow-through canal, offering the rare convenience of keeping your plane and boat close to home. Built for island living, the home features a durable metal roof and impact windows. Outside, a waterfront tiki invites you to unwind after a day on the water, while a 20,000-pound boat lift, commercial ice maker, and deep draft make this a compelling base for serious boaters. Follow the well-marked channel to the ocean, or head toward the Gulf via Kemp Channel. Explore offshore waters, cruise the backcountry, or spend an afternoon relaxing on the sandbars at Snipes or Marvin Key. Here, your next adventure can begin in the air or on the water. For the pilot who loves to fish, the fisherman who loves to fly, or anyone drawn to the freedom of both, this is more than a home - it's a distinctive way to experience the Florida Keys. Runway access and flow-through canal boating at one address make this a truly rare find! See the additional features on the Document tab. Airport information is available at: https://www.summerlandkeyairport.com/ Note: 2022 40' WorldCat is also for sale (separately).

86 S Airport Dr, Summerland
251 County Road 939, Summerland
$99,000
621712 MLS
The Ultimate Waterfront Investment: Why just buy a boat when you can own a profitable, self-sustaining business that pays for your time on the water? Sugarloaf Pontoon Adventure Tours is officially on the market! This is a fully operational, turnkey charter business designed for an owner who wants all the perks of the boating lifestyle without the heavy lifting. What's Included in the Sale: • The Vessel: A spacious 30ft pontoon boat equipped with a practically brand-new engine (only 100 hours of use!). • Turnkey Operations: Fully insured with active commercial charter insurance already in place. • The Crew: A professional, licensed captain is already running the charters. No captain's license required for the new owner! • Digital Assets: High-converting, fully functional booking website (sugarloafpontoonadventuretours.com) ready to keep taking reservations.

251 County Road 939, Summerland
637 E Caribbean Dr, Summerland
$1,100,000
2 Beds ⋅ 2 Baths ⋅ 621672 MLS
YOUR SUMMERLAND KEY WATERFRONT ESCAPE AWAITS! Enjoy the best of Florida Keys living in this beautifully remodeled 2-bedroom, 2-bath stilt home in sought-after Summerland Key. Fresh, modern interiors and a crisp monochromatic palette create a welcoming retreat, while the waterfront setting brings the boating lifestyle right to your doorstep. Step onto the porch and take in the views of a remarkable 60-foot-wide, crystal-clear flow-through canal. With excellent water circulation and a 10,000-pound boatlift, this property is designed for those who appreciate life on the water and the freedom to explore the surrounding waterways. Outside, lush, well-maintained tropical landscaping and colorful orchids add to the island charm. The fenced yard offers space for your four-legged companions, while the generous downstairs storage area provides room for fishing gear, paddleboards, and all the essentials of Keys living. Neat, well cared for, and freshly painted in 2021, this versatile property is ideal as a full-time residence, weekend getaway, or investment opportunity. Whether you're heading out for a day on the water or unwinding at home after a day of adventure, this is your opportunity to embrace the relaxed waterfront lifestyle that makes Summerland Key so special. Come discover your place in the Keys. Easy to show!

637 E Caribbean Dr, Summerland
667 E Caribbean Dr, Summerland
$1,050,000
2 Beds ⋅ 2 Baths ⋅ 621488 MLS
A BOATER'S HAVEN - Island living, exceptional boating access, and a little aviation charm come together at this inviting waterfront home in Summerland Key. Set along a deep, flow-through canal with excellent water quality and convenient access to both the Atlantic and Gulf, this 2-bedroom, 2-bath residence offers the relaxed, connected lifestyle that makes the Florida Keys so special. Surrounded by tropical landscaping and coconut palms, the home features spacious wraparound balconies that create wonderful outdoor living spaces for morning coffee, sunset cocktails, or simply enjoying the island breezes. Brick walkways weave through the grounds, adding character while keeping the outdoor spaces easy to enjoy and maintain. For boaters, the property delivers where it counts--with a 15,000-pound boat lift and deep-water canal access that makes getting out on the water effortless. Atlantic and Gulf access. Downstairs, a covered patio and generous L-shaped storage area provide practical space for gear, water toys, and island essentials. And there's an unexpected bonus: a private airstrip lies directly across the canal, adding a distinctive touch for pilots and aviation enthusiasts. Whether you're searching for a full-time island residence, a weekend retreat, or a waterfront home designed around life on the water, 677 E Caribbean Drive offers an authentic Summerland Key experience--with boating, tropical surroundings, and the freedom to enjoy the Keys at your own pace.

667 E Caribbean Dr, Summerland
947 Gulf Dr, Summerland
$1,559,000
3 Beds ⋅ 2 Baths ⋅ 621442 MLS
Clear canal waters and easy Atlantic access set the scene for waterfront living at this well-maintained Summerland Key home. Situated on a deep, clean, flow-through canal enjoyed for swimming, the property offers approximately 60 feet of dockage, davits, and two swim ladders. With no bridges to the Atlantic, it's an inviting home base for boating, fishing, diving, and enjoying the water right from your backyard. Inside, three bedrooms and two baths complement bright, open living and dining spaces with travertine flooring throughout the main living areas. The kitchen features granite countertops, stainless steel appliances, generous cabinetry, and ample workspace. An approximately 280-square-foot screened veranda overlooks the canal, offering a breezy setting for outdoor dining and relaxing. The primary suite includes a private bath, generous closet space, and direct access to the outdoor living area, while two additional bedrooms accommodate family or guests. The elevated design provides extensive covered parking and storage for vehicles, boats, trailers, and recreational gear. A fenced lot, mature palms, and tropical landscaping complete the waterfront setting. Pool renderings illustrate the potential for a private waterfront pool, drawing on a pool builder's survey-based layout. They offer a conceptual view of the proposed design; final dimensions, placement, and installation remain subject to site verification and permitting. Close to Summerland Key dining, shopping, and everyday conveniences, this home pairs clear canal waters with excellent boating access and comfortable spaces for full-time or seasonal living.

947 Gulf Dr, Summerland
481 E Shore Dr, Summerland
$5,500,000
3 Beds ⋅ 3 Baths ⋅ 621388 MLS
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!

481 E Shore Dr, Summerland
24923 Park Dr, Summerland
$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
486 S Airport 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
27 N Lake 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
24171 Overseas Hwy, Summerland
$1,300,000
3 Baths ⋅ 620841 MLS
Prime commercial property and investment opportunity! An exceptional multi-faceted real estate opportunity the the heart of the Florida Keys. Whether you are looking to hold a strong income-generating asset or immediately capitalize on aggressive redevelopment, this property delivers on both fronts. Key highlights and value drivers: 1. Immediate revenue stream: Turnkey restaurant and offices with solid existing leases in place. Collect strong passive income from day one while finalizing design, architectural or permitting plans. Suburban commercial (SC) zoning. 2. Live Local Act authorization: Authorized under Florida's Live Local Act, unlocking unprecedented density, floor area ratio (FAR) and height allowances for mixed-use or affordable/workforce residential development. 3. Unmatched visibility and location: Direct highway exposure along the primary artery connecting Key West to the Middle Keys, capturing continuous tourist traffic and serving the local community 4. Development and investment potential: Enjoy stable rental yields from established commercial tenants while holding the land for long-term appreciation or future phase expansion

24171 Overseas Hwy, Summerland
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