Summerland Key FL Real Estate & Homes for Sale

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Beds:
2
Baths:
3.00
Sq.Ft.:
960
Status:
NEW LISTING
MLS#:
621999
Type:
Single Family
Subdivision:
Breezeswept Bch Est (27.5)
Lot size:
0.13 Acres
Year built:
1984
Courtesy: Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys 305-735-4962
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ADDITIONAL INFORMATION

Looking for your own slice of Keys paradise in the highly desirable Breezeswept Estates neighborhood on Ramrod Key? Here's your opportunity to bring your vision to life in one of the Lower Keys favorite boating neighborhoods! This charming 2 bedroom, 3 bath Keys home is full of character and potential, featuring beautiful Miami-Dade pine ceilings and possibly original pine flooring just waiting to be uncovered! The open living and kitchen area offers a great starting point to make this home your own, with a convenient Jack-and-Jill-style bathroom connecting the bedrooms. The fully fenced property offers privacy, room to enjoy the outdoors, and your own dock! Downstairs, you'll find a spacious 480 sq. ft. area, plus additional storage for all your fishing, boating, and island gear. And let's talk location! You're just minutes from open water, some of the best fishing grounds in the Lower Keys, and those phenomenal sandbars we all love. Hop on your bike and head over to the famous Looe Key Tiki Bar for live music, cold drinks, and a little island fun! Boondocks is just across the street, offering food, entertainment, and miniature golf. Don't forget the local farmers market every Saturday, right here on Ramrod Key! All this island charm with Key West and the airport just a short drive away. Whether you're looking for a weekend getaway, a full-time Keys home, or a place to put your own personal touches, this property offers the location, character and potential to become something special. Bring your dreams, your flip-flops, and your vision. Your Keys canvas awaits!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,851
Status:
NEW LISTING
MLS#:
621937
Type:
Single Family
Subdivision:
Cudjoe Gardens (21.0)
Lot size:
0.23 Acres
Year built:
1968
Courtesy: Internet Realty of the Florida Keys 305-745-9088
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ADDITIONAL INFORMATION

Welcome to the ''Oceanfront Gardens'' of Cudjoe Gardens! This magnificent, lush tropical paradise is truly one of a kind. Nestled directly along the Atlantic Ocean and tucked among mature tropical trees, the property is adorned with orchids, hanging chairs, and hammocks, while the sounds of numerous bird species create a peaceful, natural soundtrack. Even the birds appreciate the privacy! This tastefully updated Florida Keys property makes you feel as though you're living on your own private island. The offering includes two amazing, contiguous lots. The first is a direct Atlantic Oceanfront property featuring an immaculate 3-bedroom, 2-bath home complete with a fitness room, new kitchen and appliances, storage/workshop, updated bathrooms, custom closets, and floor-to-ceiling impact windows showcasing beautiful ocean views. There's even a private, ocean-view ''She Shed''! The second contiguous lot, measuring 80' x 100', is also located at the end of this peaceful street in Cudjoe Gardens. This exceptional property boasts 80 feet of concrete dockage with deep-draft, protected access, a 12,000-lb. hydraulic boat lift, 10,000-lb. davits, a jet ski dock, electric, water, and lighting. With instant access to open water, this very private mini marina offers some of the most desirable boating access in all of the Florida Keys. Cudjoe Gardens Marina is located within the neighborhood for easy fuel fill ups and provisions. The dock and surrounding deep water can accommodate larger vessels, making the combination of oceanfront living and protected dockage an exceptionally rare find in the Keys. The additional lot has also been beautifully landscaped to complement the main home's peaceful, tropical atmosphere. Both lots have good elevation with no water issues in past storms. Come explore this extraordinary oceanfront compound and experience what Florida Keys living is truly all about. This could be the funnest home you'll ever own! :) Easy and a pleasure to show

Beds:
2
Baths:
3.00
Sq.Ft.:
1,156
Status:
Active
MLS#:
A12116383
Type:
Other
Subdivision:
SACARMA
Lot size:
0.02 Acres
Year built:
2007
Courtesy: Florida Realty of Miami Corp Marilin Palenzuela 786-760-9703
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ADDITIONAL INFORMATION

Experience the best of the Lower Keys with this rare opportunity to own a property that blends personal enjoyment with exceptional income potential. Whether you're searching for a private waterfront getaway, vacation retreat, or proven income-producing investment, this property delivers on all fronts. Successfully operated as a short-term rental since 2018, this home has consistently generated over $100,000 annually in rental income, offering a turnkey investment opportunity while enjoying the Florida Keys lifestyle. One of the property's most valuable features is its fully transferable transient rental license, valued at approximately $400,000. Unlike many Lower Keys properties with strict rental limitations, this license allows hotel-style rentals with no minimum night restrictions — a rare and highly desirable advantage. Each home includes a private dock slip, perfect for boats, jet skis, kayaks, and other water toys. This exclusive community of just 11 homes offers exceptional privacy, a shared heated pool, and a low, owner-operated HOA. Offered fully furnished and turnkey, the property includes established rental history and everything needed to continue operating immediately. Enjoy boating, fishing, diving, and the ultimate Florida Keys lifestyle from this ideally located Cudjoe Key property.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,638
Status:
Active
MLS#:
B26095818
Type:
Residential
Subdivision:
CUTTHROAT HARBOR ESTATES 1ST ADD
Lot size:
0.14 Acres
Year built:
1993
Courtesy: Your Esquire Realty 954-247-1491
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ADDITIONAL INFORMATION

Spend the day on the water and catch the sunset from your wraparound balcony. This custom-built home offers 60 feet of canal frontage, a private dock, a launch ramp for kayaks and small boats, and access to the Atlantic and Gulf with no fixed bridges. Inside, 2,638 square feet of living space includes four bedrooms, each with its own full bath. Impact French doors open the main living area to the balcony, and the kitchen features quartz countertops, solid wood cabinetry, and a dedicated ice maker. The top-floor primary suite has its own balcony with ocean and bay views. For movie nights, a 120-inch motorized screen, projector, and built-in Dolby Atmos sound turn the living area into a home theater. An enclosed workshop, covered parking with EV charging, and space for an RV or boat trailer.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,928
Status:
Active
MLS#:
621887
Type:
Single Family
Subdivision:
Summerland Cove Isle (25.5)
Lot size:
0.17 Acres
Year built:
1988
Courtesy: Keller Williams Key West Compass Realty 305-292-0020
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ADDITIONAL INFORMATION

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 with a heater and chiller, 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!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,175
Status:
Active
MLS#:
621860
Type:
Single Family
Subdivision:
Misc Little Torch KE (28.0)
Lot size:
2.38 Acres
Year built:
1991
Courtesy: KeyIsle Realty 305-926-8559
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ADDITIONAL INFORMATION

Location Location Location! This property offers lots of space, tons of privacy and stunning views. This home is situated on 2.38 acres of land with breathtaking open water views. Walk on to your newly refinished composite stairs to a walk around porch. Making access to the exterior of the home super easy. Interior layout is a large open floor plan living room with an abundance of space for entertaining or just relaxing. The lovely kitchen boasts plenty of cabinets, an eat in island, stainless steel appliances and granite countertops. The main living area seamlessly flows to large sliding glass pocket doors onto your 50' covered tiled porch. Where you can experience the open water view. Just a few paces down the hall the master suite shares the same spectacular view. Additional highlights include the laundry room on the porch with space for extra storage. Downstairs, a storage enclosure provides ample space for fishing gear, bicycles and all your extras. There is also plenty of covered parking beneath the house keeping vehicles cool and shaded. The yard provides more than enough room for your RV, boat and all your other toys. Add a pool and tiki hut to make this your tropical oasis. RV hookup is also available on the property. Located on a very quiet road with only one neighbor. You are just minutes from a public boat ramp, local restaurants, and a shopping center. Don't miss out on this rare opportunity to own your own generous amount of private property in the Florida Keys. Seller is motivated! Bring your offers!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,450
Status:
Active
MLS#:
TB8562058
Type:
Single Family
Subdivision:
INDIAN MOUND ESTATES
Lot size:
0.23 Acres
Year built:
1953
A broker reciprocity listing Courtesy: MERIDIAN RESIDE 727-777-6676
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ADDITIONAL INFORMATION

Discover the charm and tropical character of the Florida Keys at 19552 Aztec Street in Summerland Key! Surrounded by spectacular, mature Banyan-style trees with sprawling trunks and cascading aerial roots, this property offers a truly unique tropical setting. The main home features 3 bedrooms, 2 bathrooms, a spacious living room, functional kitchen, and a screened porch perfect for enjoying the surrounding greenery and island breezes. The primary bedroom offers a generous layout and walk-in closet, while the additional rooms provide flexibility for guests, an office, or hobbies. Adding even more versatility, a separate detached living space in the backyard features 1 bedroom, 1 bathroom, a kitchen, and a living room, offering potential for guest accommodations or multigenerational living. Conveniently located near US-1, this property provides access to local amenities, boating, fishing, and the laid-back lifestyle of the Lower Florida Keys, with Key West just a scenic drive away. A unique opportunity to enjoy tropical surroundings and flexible living options!

Beds:
1
Baths:
1.00
Sq.Ft.:
316
Status:
Active
MLS#:
621828
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.04 Acres
Year built:
1980
Courtesy: Bluescape Real Estate 305-203-2537
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ADDITIONAL INFORMATION

Enjoy the Florida Keys lifestyle at Conch Hideaway #423, a charming 1-bedroom, 1-bath retreat in the gated oceanfront community of Venture Out on Cudjoe Key. This successful vacation rental has future reservations already on the books, offering an appealing opportunity for a personal island getaway, an income-producing property, or both. The bright, open living area features coastal touches, a Smart TV, and a pull-out sofa for extra sleeping space. The kitchen makes meals at home easy, while the bedroom and full bathroom offer a comfortable place to recharge after a day on the water. Step outside for morning coffee or an evening in the tropical breeze. A separate storage shed provides space for fishing gear, bicycles, and beach essentials. Located at Mile Marker 23, Venture Out offers a heated oceanfront saltwater pool, hot tub, saltwater swimming lagoon, boat ramp, fuel dock, and ship store. Stay active with tennis, pickleball, basketball, and bocce courts, or enjoy the convenience of the recreation center, market, post office, and golf cart-friendly streets. A 24-hour gated entrance adds to the community's private setting. Whether you're planning winter escapes, weekends on the water, or continuing its vacation rental use, Conch Hideaway #423 is a welcoming home base for enjoying the Lower Florida Keys.

Beds:
6
Baths:
8.00
Sq.Ft.:
4,894
Status:
Active
MLS#:
A12112168
Type:
Other
Subdivision:
SUGARLOAF SHORES PLAT #2
Lot size:
0.3 Acres
Year built:
2025
Courtesy: Compass Florida, LLC. Wesley Ferreira
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ADDITIONAL INFORMATION

THE AZURE ESTATE Where Luxury Meets Wellness. Discover a stunning, brand-new solid concrete architectural masterpiece on the open waters of Sugarloaf Key, where striking design, coastal resilience, and wellness-inspired luxury create an extraordinary Florida Keys lifestyle. Designed for strength and peace of mind, this remarkable elevated residence pairs hurricane-resistant design features with walls of glass and endless ocean views. Step inside to a breathtaking 19-foot, double-height living room filled with natural light. Porcelain floors, elegant glass railings, and a private hydraulic elevator bring comfort and sophistication to every level. The chef's kitchen dazzles with quartzite countertops and Monogram appliances, complemented by a custom bar and dramatic stone wine display. Four private suites in the main residence open to covered waterfront terraces, inviting you to wake up to endless ocean views and gentle island breezes. Crowning the home, a full rooftop deck offers sweeping 360-degree panoramas from sunrise to sunset-an inspiring retreat for morning yoga, meditation, or unforgettable gatherings under the stars. Outside, a resort-style pool and spa, outdoor shower, convenient poolside bathroom, landscape lighting, and expansive covered entertaining areas invite you to slow down and savor island life. A planned 226-foot dock, included in the purchase price, will further elevate the boating experience. One of the property's most distinctive features is its solid reinforced-concrete parking structure, designed to accommodate up to 6 vehicles, with generous overhead storage space and convenient dual access. Boasting an impressive elevation of 11 ft 2 inch NGVD, above the designated 10-ft NGVD flood elevation, this structure offers a significant advantage in the Florida Keys, providing an added measure of protection against potential flooding during hurricanes, storm surges, and severe weather conditions. Built with solid structural concrete throughout.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,337
Status:
Active
MLS#:
621795
Type:
Single Family
Subdivision:
Summerland Key Cove (25.0)
Lot size:
0.14 Acres
Year built:
1988
Courtesy: Keller Williams Key West Compass Realty 305-292-0020
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,994
Status:
Active
MLS#:
B26092211
Type:
Residential
Subdivision:
BREEZESWEPT BEACH ESTS
Lot size:
0.14 Acres
Year built:
1987
Courtesy: William Raveis Real Estate 561-655-6570
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ADDITIONAL INFORMATION

Fully Furnished Tropical Keys Oasis - Waterfront Luxury Living Just unpack and start living the island life in this completely renovated, one-of-a-kind tropical oasis that rivals any luxury 5-star resort. Relax in the sparkling pool surrounded by lush, mature landscaping, including coconut palms, banana trees, mango trees and a Hass avocado tree. Vibrant bougainvillea archways create a stunning entry to one of the most exquisitely landscaped homes on the island. Outdoor living here is elevated to the next level and is perfect for entertaining. Enjoy 60 feet of waterfront with an expansive maintenance-free deck, a 15,000-lb boat lift and a drop dock perfect for swimming in the lagoon or launching kayaks. Inside, discover a beautiful 4-bedroom, 2.5-bath home featuring a chef's kitchen with a 6-burner gas stove, double farm sink, all-new stainless-steel appliances and a massive center island with abundant storage, so you can enjoy everyday luxury living. Gorgeous tile flooring flows throughout. The first floor offers three guest bedrooms, a stylishly renovated bath, a convenient half bath and a full laundry room with gas dryer. The spacious living room opens through triple sliding glass pocket doors to a screened porch secluded by palms, bringing your indoor living outdoors in the winter and ideal for morning coffee or dining al fresco year-round. Upstairs, the primary suite is a private retreat with panoramic water views, a custom walk-in closet and a spa-inspired bathroom with an oversized shower featuring six body jets, a handheld sprayer and a ceiling-mounted rain shower. Dual vanities and a lighted mirror complete this luxurious sanctuary. Additional features include: - Brand-new impact windows and doors throughout - Metal roof - Fully fenced backyard, perfect for pets and privacy - 300 sq. ft. storage room with impact windows and doors - Irrigation system - Propane gas - Endless on-demand gas water heater - And so much more!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,728
Status:
Active
MLS#:
621715
Type:
Single Family
Subdivision:
Summerland Key Cove (25.0)
Lot size:
0.13 Acres
Year built:
1980
Courtesy: Keller Williams Key West Compass Realty 305-292-0020
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ADDITIONAL INFORMATION

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).

Beds:
2
Baths:
2.00
Sq.Ft.:
836
Status:
Active
MLS#:
621700
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.05 Acres
Year built:
1999
Courtesy: Bluescape Real Estate 305-203-2537
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ADDITIONAL INFORMATION

Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean. Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private deck—an ideal spot for your morning coffee or evening entertaining. This tropical retreat sits on a large, lushly landscaped corner lot, offering both privacy and ample space. The home itself is in excellent condition and is move-in ready, featuring modern, high-end appliances and the peace of mind that comes with accordion hurricane shutters. The versatile layout includes significant bonus space underneath the house, perfect for storage, entertaining, working on projects or just relaxing in the shade in your hammock. This is not just a home; it's a prime investment. With nightly rentals allowed and plenty of opportunities for success on platforms like Airbnb and VRBO to help offset your costs. Don't miss your chance to own a piece of paradise. Schedule your private showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,040
Status:
Active
MLS#:
621672
Type:
Single Family
Subdivision:
Summerland Key Cove (25.0)
Lot size:
0.14 Acres
Year built:
1993
Courtesy: Keller Williams Key West Compass Realty 305-292-0020
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ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,295
Status:
Active
MLS#:
621664
Type:
Single Family
Subdivision:
Cutthroat Harbor Est (23.0)
Lot size:
0.35 Acres
Year built:
1992
Courtesy: Island Welcome Real Estate 305-923-9161
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ADDITIONAL INFORMATION

Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking water views, where dolphins, rays, and vibrant marine life become part of your daily backdrop. Three luxurious en-suite bedrooms offer refined comfort and privacy, including a main-level guest suite and two upper-level retreats--one featuring a spa-inspired bath with a glass-tiled walk-in shower, the other with a soaking tub overlooking the ocean. Outdoor living is truly resort-inspired, with a private pool, expansive pool deck, and a fully appointed cabana lounge complete with bar, TV, and entertaining space. A rare private beach invites effortless paddle-outs into crystal-clear, opal-toned waters. Multiple balconies and a spectacular rooftop deck provide unforgettable sunrise and sunset views. The chef's kitchen is both functional and striking, featuring an oversized island with unique stone countertops, walk-in pantry, and direct access to a balcony with grilling area. Additional highlights include a poolside grill, ground-level laundry and storage, private dock, and boat ramp with immediate access to world-class fishing and diving. Located just 30 minutes from Key West, this exceptional waterfront retreat delivers the ultimate blend of modern luxury, privacy, and the unmatched lifestyle of the Lower Florida Keys.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,954
Status:
Active
MLS#:
A12106999
Type:
Other
Subdivision:
BREEZESWEPT BEACH ESTS
Lot size:
0.41 Acres
Year built:
2013
Courtesy: Capital Intl Realty LLC Sonia Petraitis 954-882-9059
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ADDITIONAL INFORMATION

Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly found in the Keys. The elevated concrete home features a spacious layout, multiple balconies, and abundant natural light throughout. With kitchen and bathrooms ready for renovation, this is the perfect canvas to create a custom waterfront residence or maximize value through a strategic upgrade. Enjoy ample outdoor space with room for expansion, a pool, additional storage or enhanced landscaping - making this property uniquely versatile for both end-users and investors. Ideally located within close proximity to Key West, offering convenient access to world class dining, entertainment and boating, while still enjoying the privacy and tranquility of canal front living.

Beds:
2
Baths:
2.00
Sq.Ft.:
748
Status:
Active
MLS#:
621559
Type:
Single Family
Subdivision:
Venture Out (23.0)
Lot size:
0.05 Acres
Year built:
1988
Courtesy: Bluescape Real Estate 305-203-2537
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ADDITIONAL INFORMATION

Enjoy your own Florida Keys getaway with the flexibility of nightly rentals! Located on a spacious corner lot in the gated Venture Out community on Cudjoe Key, this 2-bedroom, 1.5-bath home is offered fully furnished and currently operates as a vacation rental. Inside, the kitchen features generous cabinet space and tiled countertops, with an open connection to the dining area that makes everyday living and entertaining easy. Tile flooring throughout, built-in bedroom and hallway storage, and a stackable washer and dryer add comfort and convenience. Updates include central air conditioning and heat installed in 2024, plus impact-resistant windows and a sliding door installed in July 2024. Vinyl siding and a metal roof complement the home's easy-care appeal. Venture Out offers 69 acres of waterfront community living with access to both Atlantic and Gulf waters. Boaters will appreciate the community boat ramp, marina store with fuel and bait, and boat washdown station. Spend your days enjoying the 80-foot heated pool, hot tub, kiddie pool, saltwater swimming lagoon, lighted tennis courts, basketball, and bocce. A convenience market, post office, and golf-cart-friendly setting make island life even more convenient. Whether you're looking for a personal retreat, an income-producing vacation property, or a combination of both, this furnished corner-lot home offers a welcoming place to make it happen with Key West just a short drive away.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,696
Status:
Active
MLS#:
621554
Type:
Single Family
Subdivision:
Cudjoe Acres (21.5)
Lot size:
0.5 Acres
Year built:
2023
Courtesy: Island Welcome Real Estate 305-923-9161
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ADDITIONAL INFORMATION

Beautiful modern design meets tropical estate living in this stunning half-acre property on Cudjoe Key! Just 21 miles from Key West, with Key West International Airport offering a growing list of flights reaching all over the country, this private retreat puts island life within easy reach. Built in 2023, this 3 bed / 2 bath coastal contemporary offers 1,696 sq ft of light-filled living beneath soaring 15-ft vaulted ceilings, plus expansive covered porches that catch the ocean breeze and frame stunning open-water views. Thoughtfully upgraded by the current owners, the property now offers a complete Keys lifestyle with a new concrete pool and sun shelf, poolside tiki hut, lush grass lawn, new tropical landscaping, and custom black aluminum fencing - a rare bonus in the Keys and a dream for four-legged family members. Offered beautifully furnished and move-in ready, with like-new Restoration Hardware and Room & Board furnishings, making it easy to begin enjoying the Keys lifestyle from day one. Built to last with CGI impact windows and doors, metal roof, blown-in foam insulation, Cambria Quartz, and Sonos throughout. Wired for an exterior elevator lift, with a free-standing storage shed built to 180 mph, and ample parking for an RV, trailer, and toys. No HOA. Public utilities include FKAA water service, connection to municipal sewer, Keys Energy for electric service, and high speed digital cable. For boating, access to the Blimp Rd community boat ramp or the Cudjoe Gardens Marina are just five minutes away. Enjoy some of the Keys' best restaurants and cafes nearby, with nightly live music and outdoor dining. This is fantastic Keys living! Check out the video to see more.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,006
Status:
Active
MLS#:
621530
Type:
Single Family
Subdivision:
Breezeswept Bch Est (27.5)
Lot size:
0.14 Acres
Year built:
1998
Courtesy: KeyIsle Realty 305-926-8559
View additional info

ADDITIONAL INFORMATION

**OPEN HOUSE SUNDAY NOV. 1 FROM 11:00AM - 1:00PM** Welcome to 27416 Tobago Lane, where waterfront living and the Florida Keys lifestyle come together. This home offers open-water views and an abundance of indoor and outdoor spaces designed to make the most of island living. Boaters will appreciate the 10,000-lb boat lift and Jet Ski davit, while the fenced yard, lush tropical landscaping and multiple outdoor areas create your own private retreat. One of the home's most memorable features is the 3rd-story observation and sun deck. Take in the open-water views and ocean breeze during the day, then enjoy unobstructed stargazing and meteor showers at night. Tucked into the tropical landscaping you'll also discover a private meditation garden, orchid garden, mature fruit trees and a charming outdoor shower -- special spaces that give this property a personality all its own. Inside, high-end custom finishes and electric fireplaces add comfort and character, while an enclosed garage and oversized storage rooms provide the practical space that's so valuable in the Keys. Recent improvements include a 2025 A/C system along with a 2026 pool pump and saltwater system. Whether your perfect Keys day means heading out on the boat, relaxing by the pool, enjoying the gardens or ending the evening under the stars, 27416 Tobago Lane offers so many ways to enjoy life in the Florida Keys. Come see what makes this home special.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,488
Status:
Active
MLS#:
621510
Type:
Single Family
Subdivision:
Misc Summerland Key (25.0)
Lot size:
0.18 Acres
Year built:
2013
Courtesy: Luxur Realty LLC dba: Realty One Group Evolution 786-477-4715
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ADDITIONAL INFORMATION

Beautiful furnished waterfront home in Summerland Key offering 3 bedrooms and 2 bathrooms, available for seasonal or extended stays with a 28-day minimum. Enjoy the relaxed Florida Keys lifestyle from this inviting canal-front property featuring a private concrete dock and convenient access to surrounding waterways and open water. The home offers a fully equipped kitchen, spacious living and dining areas, comfortable bedrooms, A/C, washer and dryer, high-speed Wi-Fi, private parking, and a covered outdoor area overlooking the canal--perfect for relaxing and enjoying the peaceful waterfront setting. An excellent option for boating and fishing enthusiasts, as well as guests looking to enjoy kayaking, snorkeling, nearby islands, or simply unwind in the Keys. The property is conveniently located near marinas, local restaurants, and other area attractions, with Key West just a short drive away. Ideal for seasonal stays, extended vacations, or remote work in a beautiful waterfront setting. Preferred pricing may be available for stays of 60, 90, or more days. An optional private pontoon boat may also be available for an additional fee, subject to a separate agreement, insurance requirements, and applicable boating qualifications. Come experience waterfront living and everything the Florida Keys lifestyle has to offer from your own private retreat in Summerland Key. FOR SHOWINGS OR ADDITIONAL INFO PLEASE SEE AGENT REMARKS

Beds:
2
Baths:
2.00
Sq.Ft.:
1,095
Status:
Active
MLS#:
621488
Type:
Single Family
Subdivision:
Summerland Key Cove (25.0)
Lot size:
0.14 Acres
Year built:
1986
Courtesy: Keller Williams Key West Compass Realty 305-292-0020
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ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
2.00
Sq.Ft.:
963
Status:
Active
MLS#:
621504
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.04 Acres
Year built:
2005
Courtesy: Bluescape Real Estate 305-203-2537
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ADDITIONAL INFORMATION

Boating is at the heart of life at Venture Out Unit 321. This elevated, canal-front 2-bedroom, 2-bath home has a 35-foot concrete dock and seawall, with easy access from the community to both the Atlantic Ocean and the Gulf of Mexico. Enjoy canal and open-water views from the covered porch after a day on the water. Inside, 963 square feet of living space includes an open kitchen with stainless steel appliances and a breakfast bar. Below the home are covered parking, shaded outdoor space, and storage. The property also features a metal roof, impact windows, and accordion shutters and is offered furnished. Venture Out at Cudjoe Cay permits nightly rentals and offers two onsite boat ramps, an onsite boat fuel station, a marina & convenience store, oceanfront heated pool and spa, and sports courts. Plus lots of community activities! With your boat docked at home and so much close at hand, Unit 321 is ready for the Florida Keys lifestyle.

Beds:
1
Baths:
1.00
Sq.Ft.:
768
Status:
Active
MLS#:
621464
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.05 Acres
Year built:
1988
Courtesy: Coldwell Banker Schmitt RE Co. 305-872-3050
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ADDITIONAL INFORMATION

Looking for your own little piece of paradise? This waterfront home may be the one. Situated along a canal, it offers beautiful water views from the 17-foot concrete dock, complete with a covered back patio ideal for grilling or relaxing. The patio also features a mini sink, mini fridge, and mini freezer for your entertaining pleasure. The spacious primary suite includes a king-size bed, custom closets with built-in drawers, and large windows overlooking the back patio. The beautifully updated bathroom features a walk-in shower with glass doors, handrail, built-in bench, skylight, humidifier, and exhaust fan. A versatile bonus room can serve as a second bedroom, office, or additional living space. The upgraded kitchen boasts granite countertops, a glass-tile backsplash, and stainless-steel appliances, including a gas range with convection oven and air fryer, center burner includes a griddle feature, a refrigerator with bottom drawer freezer, a microwave, and disposal. Additional features include a pantry with drawers, a 70-pound propane tank, an on-demand hot water heater, four ductless AC units, and a full-size stackable washer and dryer conveniently tucked into the hallway closet. Numerous hallway closets provide ample storage. All windows are double paned. The home features a gable metal hip roof, gutters, Bahama and panel shutters, and reinforced FEMA-approved piers. The oversized concrete driveway provides parking for both a car and a golf cart. Large doors offer easy access to plenty of additional storage beneath the home. Venture Out offers an abundance of amenities, including oceanfront picnic areas and tiki huts, boat ramps, a marina with fuel dock and store, heated saltwater pool, hot tub, tennis and pickleball courts, bocce courts, basketball courts, community bathhouses, laundry facilities, and a clubhouse with ongoing activities. The community is completely walled, gated, and secured with on-site security guards.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,400
Status:
Active
MLS#:
621442
Type:
Single Family
Subdivision:
Summerland Cove Isle (25.5)
Lot size:
0.14 Acres
Year built:
1988
Courtesy: Coldwell Banker Schmitt Real Estate Co. 305-743-5181
View additional info

ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,088
Status:
Active
MLS#:
621388
Type:
Single Family
Subdivision:
Summerland Estates (25.0)
Lot size:
1.07 Acres
Year built:
1992
Courtesy: Berkshire Hathaway HomeServices Keys Real Estate 305-743-7636
View additional info

ADDITIONAL INFORMATION

Exceptional Investment Opportunity in the Lower Florida Keys! Seller financing is available with a 20% down payment, 6.5% interest in a 5-year balloon. Other additional terms are subject to seller approval. 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!

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Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Florida Keys Board of Realtors® Florida Keys MLS, Inc. Real Estate listings held by brokerage firms other than the owner of this site are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Use of search facilities of data on the site, other than a consumer looking to purchase real estate, is prohibited. © 2026 MIAMI Association of REALTORS®, all rights reserved.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.


Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of {{last updated}}. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2026, My Florida Regional MLS DBA Stellar MLS.



Summerland Key 33042 Real Estate

Summerland Key is located in Florida. Summerland Key, Florida 33042has a population of 6,609. Summerland Key 33042 is less family-centric than the surrounding county with 17.31% of the households containing married families with children. The county average for households married with children is 20.65%.

The median household income in Summerland Key, Florida 33042 is $95,365. The median household income for the surrounding county is $73,153 compared to the national median of $69,021. The median age of people living in Summerland Key 33042 is 50.4 years.

Summerland Key Weather

The average high temperature in July is 89.4 degrees, with an average low temperature in January of 63.4 degrees. The average rainfall is approximately 44.4 inches per year, with 0 inches of snow per year.

Summerland Key Map

Summerland Key Real Estate Market Conditions

  • Median sales price

    $900,000
    26.6%
    change since last quarter
  • # Active listings

    285
    30-day change

Summerland Key Schools and Demographics

Education near Summerland Key, FL

City County
High School Graduates 96.84 92.07
College Degree - 2 year 7.68 7.93
College Degree - 4 year 41.72 35.69
Graduate Degree 10.7 9.88
Expenditures per Student 20,907 20,907
Students per Teacher 14.7 14.7

Elementary Schools near Summerland Key, FL

Grades Students P/T Ratio ZIP
Big Pine Academy PK - 08 177 12.6 33043
Gerald Adams Elementary School PK - 05 544 13.3 33040
Horace O'Bryant School PK - 08 1,059 14.3 33040
Key Largo School PK - 08 847 14.1 33037
Key West Montessori Charter School KG - 08 149 16.6 33040
Monroe Virtual Instruction Program (District Provided) KG - 05 6 33040
Ocean Studies Charter KG - 05 104 11.2 33070
Plantation Key School PK - 08 435 12.8 33070
Poinciana Elementary School PK - 05 663 15.1 33040
Sigsbee Charter School KG - 08 478 17.1 33040
Stanley Switlik Elementary School PK - 05 566 14.2 33050
Sugarloaf School PK - 08 526 15 33042
Treasure Village Montessori Charter School PK - 08 213 14.2 33036

Middle Schools near Summerland Key, FL

Grades Students P/T Ratio ZIP
Glynn Archer Elementary School PK - 05 394 15.8 33040

High Schools near Summerland Key, FL

Grades Students P/T Ratio ZIP
Coral Shores High School 09 - 12 733 17.4 33070
Key West Collegiate School 09 - 12 78 15.3 33040
Key West High School 09 - 12 1,193 16.8 33040

Ungraded Schools near Summerland Key, FL

Grades Students P/T Ratio ZIP
* Keys Center 08 - 12 11 11 33040
Academic Connections for Excellence 06 - 12 11 33040
Adult/Vocational/Community Education AE - AE 0 33040
Hurricane Island Outward Bound 06 - 12 12 33037
Marathon School 06 - 12 667 18.5 33050
Monroe Virtual Academy (Course Offerings) 06 - 12 0 33040
Monroe Virtual Franchise 06 - 12 4 33040
Monroe Virtual Instruction Program KG - 12 0 33040

Demographics near Summerland Key, FL 33042

Zip Code City
Neighborhood Type Small town
Population 6,609 82,244
Population Density 259 84
Median Age 50.4 48
People per Household 2.4 2.4
Median Household Income 95,365 73,153
Average Income per Capita 61,118 50,050

Real estate near Summerland Key