Summerland Key Homes with Canal Front Waterfront features

Summerland Key Homes with Canal Front Waterfront features

Welcome to Summerland Key, a hidden gem nestled in the heart of the Florida Keys, within Monroe County. This idyllic island paradise offers a unique blend of natural beauty, vibrant community life, and exceptional waterfront living. With its pristine beaches, lush tropical landscapes, and stunning sunsets, Summerland Key is the perfect destination for those seeking a serene escape from the hustle and bustle of everyday life.

One of the most alluring features of Summerland Key is its stunning canal-front homes, which provide direct access to the sparkling waters of the Atlantic Ocean. Imagine waking up each morning to the gentle sound of waves lapping against your dock, with the sun rising over the horizon, casting a golden glow on your private oasis. These homes are designed for both relaxation and adventure, offering ample space for entertaining, outdoor living, and, of course, boating enthusiasts will appreciate the convenience of having their vessels right at their doorstep.

The community of Summerland Key is known for its friendly atmosphere, where neighbors become friends and everyone shares a love for the outdoors. Whether you're exploring the nearby nature trails, enjoying water sports, or simply lounging by the water, you'll find that life here is all about embracing the beauty of nature.

With a variety of canal-front properties available, ranging from cozy cottages to luxurious estates, Summerland Key truly has something for everyone. Experience the magic of island living and make your dream home a reality in this enchanting corner of Florida. Your waterfront paradise awaits!

Newest Summerland Key Homes with Canal Front Waterfront features

$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
$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
$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
$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
$2,246,000
3 Beds ⋅ 2 Baths ⋅ 620177 MLS
Built for the offshore lifestyle, this exceptional Summerland Key waterfront home blends luxury coastal living with the kind of boating access serious anglers dream about. Completely renovated from top to bottom, the property sits on a deep water canal with 60 feet of brand new concrete dockage and quick direct access to open water, making it ideal for larger center consoles, sportfish boats, and offshore cruising. Inside, the home was designed for relaxed Keys living with vaulted ceilings, impact windows and doors, quartz countertops, custom wood cabinetry, stainless steel appliances, and an open layout filled with natural light and canal views. The spacious primary suite is privately situated on the second floor, offering a peaceful retreat with elevated views and added separation from the guest accommodations below. The outdoor living experience is what truly sets this property apart. The waterfront pool features all brand-new equipment, including a heater and chiller, allowing for year-round enjoyment in every season. A portion of the pool area is partially covered, creating the perfect shaded outdoor lounge space after a day on the water. Covered balconies, spacious patios, and tropical landscaping give the property a true private resort feel. The custom putting green and mini golf area adds a unique touch rarely found in the Keys, creating an incredible space for entertaining guests while enjoying the waterfront setting. Whether you're heading offshore for tuna and swordfish, running to the reef, or enjoying sunset cruises through the Lower Keys, this location puts you minutes from some of the best boating and fishing in the Florida Keys. Built with durable Hardie board construction, a metal roof, impact windows and doors, covered parking, and more than 1,000 square feet of enclosed storage space underneath the home, this turnkey waterfront retreat offers the perfect balance of luxury, functionality, and the authentic Florida Keys boating lifestyle.

848 E Caribbean Dr, Summerland
$395,000
620006 MLS
Purchase this deep draft canal front LOT in Summerland Key in the Florida Keys. The building permit is in-process for a 3 bedroom/ 2 bath stilted single family residence (cost of the home is additional). The plans shown are for a 1320 sq ft' 3/2 elevated Affinity home with features that include impact doors and windows and built to 180 mph which is great for your insurance rates. This canal has incredibly easy access to the Atlantic and Gulf with deep draft. Buy the land now and when your permit comes in, you can start building or you can change the plans. Price does not include the home and will increase as construction progresses. Limited lots are available in this upscale neighborhood. DOCK permit update from Army Corp.

24285 W 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
$899,000
619387 MLS
Rare opportunity in the heart of Summerland Key, two contiguous waterfront lots totaling 12,000 SF in the SC (Suburban Commercial) zoning district. Offering over 120 feet of premium frontage - both on the highly visible Overseas Highway and on deep-water accessible oceanside canal - this property delivers exceptional visibility and flexible commercial potential. 120' concrete dockage with direct deep-water boating access. Ideal for restaurants, retail, marine services, storage or a signature mixed-use development, this prime waterfront parcel promises high-impact exposure and unmatched convenience in a sought-after Florida Keys location. Summerland Key is a unique fly-in community with private airstrip and marina close by.

24764 Overseas Hwy, Summerland
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