Summerland Key Homes with Cash Finance Terms

Summerland Key Homes with Cash Finance Terms

Welcome to Summerland Key, a hidden gem nestled in the heart of the Florida Keys, within Monroe County. This enchanting island offers a unique blend of natural beauty, vibrant marine life, and a tight-knit community atmosphere that makes it an ideal location for your dream home.

Summerland Key is known for its stunning waterfront properties, where crystal-clear waters meet lush tropical landscapes. Whether you're drawn to the allure of sun-soaked beaches, the thrill of water sports, or simply the tranquility of island life, this charming locale has something for everyone. Residents enjoy easy access to world-class fishing, snorkeling, and diving spots, making it a paradise for outdoor enthusiasts.

The real estate market in Summerland Key is diverse, featuring everything from cozy cottages to luxurious waterfront estates. Many of these homes are available with cash finance terms, making it easier for buyers to secure their slice of paradise without the complexities of traditional financing. This flexibility opens the door for a range of buyers, from investors seeking rental opportunities to families looking for a permanent residence in this idyllic setting.

As you explore Summerland Key, you'll discover a warm community spirit, with local shops, restaurants, and recreational facilities just a stone's throw away. The island's charm is matched only by its natural beauty, making it a perfect place to call home. Embrace the laid-back lifestyle and make Summerland Key your sanctuary in the Florida Keys—where every day feels like a vacation!

Newest Summerland Key Homes with Cash Finance Terms

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
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
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
361 Ave D, 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
23940 Overseas Hwy, 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
Howell Ky, 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
Start Your Search

How much is your home worth?

Get instant property value now!