Summerland Key Homes with Conventional Finance Terms

Summerland Key Homes with Conventional Finance Terms

Welcome to Summerland Key, a hidden gem nestled in the heart of the Florida Keys, Monroe County. This picturesque island offers a unique blend of tranquil island living and vibrant community spirit, making it an ideal destination for those seeking a slice of paradise. With its stunning waterfront views, lush tropical landscapes, and proximity to both the Atlantic Ocean and the Gulf of Mexico, Summerland Key is a haven for boating enthusiasts, fishing aficionados, and anyone who appreciates the great outdoors.

Homebuyers will find a variety of charming properties, from cozy cottages to luxurious waterfront estates, all designed to embrace the island lifestyle. Whether you're looking for a vacation retreat or a permanent residence, Summerland Key offers homes that are not only beautiful but also accessible through conventional financing options. This means that your dream home can be within reach, allowing you to invest in a slice of paradise without the complexities often associated with alternative financing.

The community in Summerland Key is warm and welcoming, with a strong emphasis on outdoor activities and a relaxed pace of life. Enjoy kayaking through mangroves, fishing off the local docks, or simply soaking in the sun on your private deck. With a range of local amenities, including quaint shops and delicious dining options, you'll find everything you need right at your fingertips.

Discover the allure of Summerland Key, where the sunsets are as breathtaking as the homes. Embrace the opportunity to live in this idyllic setting and make your dream of island living a reality!

Newest Summerland Key Homes with Conventional Finance Terms

$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
$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
$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
$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
$1,185,000
3 Beds ⋅ 2 Baths ⋅ 620281 MLS
OVERSIZED GARAGE. WATERFRONT LIVING. Bring the boat, tackle, dive gear, kayaks, and all the Keys toys-there's room for everything at 706 Caribbean Drive East. With canal frontage, a 10,000-pound boat lift, and quick ocean access, this property is built for life on the water. The massive 1,188-square-foot garage below is a dream setup for serious boaters, offering space for storage, a workshop, multiple vehicles, and gear. Inside you'll love the kitchen layt up for cooking and entertaining. Hardi-board siding, new metal roof (installed in 2018), and a fenced yard complete the exterior. If you've been searching for waterfront living without sacrificing storage, this Summerland Key Cove home delivers.

706 E Caribbean Dr, Summerland
$1,200,000
2 Beds ⋅ 2 Baths ⋅ 619455 MLS
Elevated COASTAL LIVING meets clean, modern design in this beautifully remodeled 2BD/2BA stilted home in sought-after Summerland Key. Designed with a striking monochromatic palette, the interiors feel fresh, cohesive, and effortlessly sophisticated--ready for you to start living the Keys lifestyle. Step outside to a relaxing porch overlooking a 60' wide, crystal-clear flow-through canal--perfect for enjoying morning coffee, evening cocktails, or simply watching the boats pass by. Boaters will appreciate the excellent water flow and easy access, ideal for keeping your vessel in prime condition. on the 10,000 pound boatlift. The property is framed by lush, meticulously maintained grounds, where vibrant orchids add a soft tropical elegance and a welcoming sense of tranquility. Downstairs, you'll find ample storage space with room for all your gear--whether it's fishing equipment, paddleboards, or even a dedicated workout area. Fenced and ready for your furry pets. Clean, neat, and thoughtfully updated, this home is the perfect blend of style, function, and island charm--ideal as a full-time residence, weekend escape, or investment opportunity. Freshly painted in 2021. Come experience simple, refined Keys living at its best--schedule your private showing today. EASY to show!

637 E Caribbean Dr, Summerland
$1,100,000
2 Beds ⋅ 2 Baths ⋅ 619318 MLS
PILOTS and BOATERS will love this! Tucked away in the heart of Summerland Key, this charming 2-bedroom, 2-bath home captures the essence of true Florida Keys living. Surrounded by swaying palms and coastal breezes, the property features inviting wraparound balconies--perfect for morning coffee or unwinding after a day on the water. Designed with boaters in mind, you'll appreciate the deep, flow-through canal offering excellent water quality and easy access to the Atlantic and Gulf, along with a 15,000 lb boat lift ready for your next adventure. Brick walkways add warmth and character, guiding you through the lush, tropical setting and creating a welcoming, low-maintenance outdoor space. Downstairs you'll love the covered patio and L-shaped storage area. Across the canal is a private airstrip calling PILOTS and BOATERS. Whether you're looking for a weekend escape or a full-time island home, this property delivers comfort, functionality, and that laid-back Keys lifestyle buyers are chasing.

667 E Caribbean Dr, Summerland
$2,220,000
3 Beds ⋅ 2 Baths ⋅ 619294 MLS
High quality concrete 3/2 in Summerland Cove. One of the best boating communities in the lower Keys for deep water, aqua blue canal water, and oceanside access with no bridges! Brand new 60' concrete dock has just been installed. Step inside to find the fresh, modern renovation done in 2024. Featuring 3 bedrooms 2 baths with the private 3rd floor primary suite. 24'' modern white tile throughout, impact windows and doors with custom window blinds with a filtered light or privacy mode. Expansive great room with vaulted ceiling, all new recessed lighting, coastal kitchen with quartz countertops and waterfall edge. The large covered back porch overlooks the canal. Rear stairs to the custom concrete pool and 60' concrete dock. Lower storage room and covered parking. Enjoy access to world class fishing and diving sites in just minutes. Situated on a 60x100 ft lot in one of the most desirable neighborhoods in the Lower Keys.

937 Gulf Dr, Summerland
$3,295,000
3 Beds ⋅ 3 Baths ⋅ 619204 MLS
A stunning location with all attributes geared to the view of the beautiful open bay of Summerland Cove. This OCEANFRONT 3 bedroom 3 bath home is on the market for the first time since construction in 1996 and features an extensive renovation nearly complete. The property includes a stunning covered & heated pool with screened enclosure, a 28 foot concrete dock with davits, deep water boating access, a spacious 2 car garage(~700sqft), majority impact glass, and a standing seam metal roof installed June 2018 with 140 mph rating. The layout of the home includes a split floor plan with a generous master suite with a large walk-in closet and an ensuite with floor to ceiling Italian polished marble. There are 3 full baths upstairs, a spacious living room with a 3 paneled pocket slider that creates a seamless indoor to outdoor transition with the stunning ocean view. The kitchen remodel includes quartz counters, stainless appliances, and soft close cabinets & drawers. In addition to the pool & the garage, the downstairs expands the air-conditioned living with a family room & foyer with designed room to add an elevator as well as a covered outdoor kitchen on a pavered patio. With the current renovation nearing completion, this spectacular location is ready for new owners and their vision of a fabulous Florida Keys tropical retreat.

24348 Caribbean Dr, Summerland
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