Summerland Key FL Real Estate & Homes for Sale

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Beds:
3
Baths:
3.00
Sq.Ft.:
1,700
Status:
Active
MLS#:
617678
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.23 Acres
Year built:
1979
Courtesy: Taylor & Assoc. RE, Inc. 305-509-9928
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ADDITIONAL INFORMATION

There are homes that check boxes, and then there are homes that speak to you the moment you step inside. This custom, meticulously crafted 3BR/3BA, 1,700 sq ft CBS masterpiece in the heart of Sugarloaf Shores is the latter, where thoughtful design, quiet elegance, and a touch of whimsy blend into a living experience that feels both luxurious and deeply personal. Set just 19 minutes from Key West, the property sits along a beautiful, clear canal, offering water views and easy access to the Lower Keys' favorite boating and backcountry destinations. Inside, light spills across creamy stone floors, warm wood accents glow overhead, and every detail feels intentional, curated, and truly one-of-a-kind. The kitchen is unforgettable: a sculpted metal vent hood, rich bronze farmhouse sink, hand-selected stone counters, custom pot filler, and Miele appliances. With wood-paneled ceilings and soft ambient lighting, the space feels like a European countryside retreat blended with island luxury, a kitchen you dream of cooking in, where mornings feel peaceful and evenings linger. The open living area flows naturally for gathering and connection. A split bedroom design enhances privacy, and the primary suite offers a walk-in closet and spa-inspired bath wrapped in warm textures and indulgent finishes. Outside, the property continues to impress with approximately 100 feet of concrete dockage with davits, perfect for days spent boating, fishing, or exploring hidden mangroves. The oversized 10,050 sq ft lot provides ample room to design the tropical pool of your dreams, surrounded by swaying palms and breezy outdoor living spaces. Built with solid CBS construction, metal roof, and full impact windows/doors, this home offers durability without sacrificing its soulful, custom aesthetic. Every inch feels chosen with care. Every finish feels meaningful. Every space tells a story.

Beds:
1
Baths:
1.00
Sq.Ft.:
368
Status:
Active
MLS#:
617682
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.06 Acres
Year built:
1978
Courtesy: Bluescape Real Estate 305-203-2537
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ADDITIONAL INFORMATION

Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area. The home is clean and well cared for, offering a functional layout appropriate for full-time living or seasonal use. While it has not been a strong rental performer, transient rentals are permitted within the community with no minimum night requirement, allowing flexibility for future use. Venture Out is a gated, waterfront community offering a variety of amenities, including a large saltwater swimming pool and lagoon, a full-service marina with boat ramp and fuel dock, and boating access to both the Gulf of Mexico and the Atlantic Ocean. Additional amenities include pickleball, tennis, bocce ball, and basketball courts, a playground, two community centers, organized activities, and on-site church services. This property may also offer alternative use potential, as the lot can be converted to an RV lot or built to suit, subject to current building regulations. Schedule a showing to explore the possibilities.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,764
Status:
Active
MLS#:
617675
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.34 Acres
Year built:
1991
Courtesy: The Agency Florida Keys 305-916-1105
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ADDITIONAL INFORMATION

RARE Solar-Powered Waterfront Tropical Gem with TESLA Solar Storage Banks on Prestigious Sugarloaf Key! A rare opportunity to own a fully solar-powered waterfront residence featuring 26 solar panels and two Tesla Solar Powerwall storage banks, offering exceptionally low energy costs, backup power, and the potential to earn credits by supplying excess energy back to the grid. This elevated 3 BD, 2 BA, 1,764 SF home sits on exclusive Southpoint—only three homes from open water and just 20 minutes to Key West. Step inside to a breathtaking cathedral Cupola, soaring above the open living, dining, and great room. Impact-glass windows fill the space with natural light, highlighting the home's tropical architecture and warm coastal finishes. The kitchen is designed for effortless entertaining with a double island, stainless steel appliances, and new quartz countertops. The split floor plan creates exceptional privacy. The primary suite features a large walk-in shower, jacuzzi tub, double vanity, and a spacious walk-in closet that connects to a versatile laundry/fitness/office room—also home to the Tesla storage banks. The opposite wing offers two guest bedrooms and a dual-access bathroom with two private vanities. Enhance your waterfront lifestyle with an impressive concrete boat ramp for jet skis, boats, kayaks, and paddleboards, plus a newly installed 10,000 lb boat lift on a deep, wide, crystal-clear canal providing fast access to both the Gullf and Atlantic. The oversized 15,000 SF lot bursts with vibrant tropical landscaping and includes a newly completed tropical pool with natural rock feature. Enjoy sunset views and star-filled nights from the rooftop observation deck. Additional features include Andersen impact windows and sliding glass doors, low insurance costs, covered parking, and excellent storage below the home. A rare Keys offering combining sustainable energy, modern resilience, and luxurious waterfront living—an exceptional opportunity in today's m

Beds:
6
Baths:
8.00
Sq.Ft.:
4,894
Status:
Active
MLS#:
617664
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.3 Acres
Year built:
2025
Courtesy: The Agency Florida Keys 305-916-1105
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ADDITIONAL INFORMATION

Masterpiece of Modern Strength & Luxury Brand-New Concrete Waterfront Estate on Prestigious Sugarloaf Key! This extraordinary new construction stunner is engineered as a rare modern fortress— built entirely of concrete, built to the most stringent hurricane-resistant codes, and designed for the discerning buyer who demands architectural excellence, security, and elevated coastal living. Set on prime open water with sweeping panoramic views, this property delivers the rare combination of minimalist modernism, structural integrity, and luxury resort-style design. The residence showcases a dramatic full flat rooftop deck spanning the entire top of the main home, offering uninterrupted 360° ocean sunrise and sunset views - private viewing platform unlike anything else in the Lower Keys. Inside, a breathtaking 19-ft double-volume open living area is wrapped in walls of glass, flooding the space with natural light. Sleek interior glass railings, porcelain floors, and refined finishes create a sophisticated aesthetic. Stunning chef's kitchen appointed with quartzite countertops, Monogram appliances, a bespoke bar, and a stone wine-display feature, all designed for high-end entertaining. The main residence features four luxurious private suites, each oriented to capture open-water views with direct access to generous covered terraces. A rare architectural highlight is the elevated above-flood concrete garage with soaring ceilings, loft storage space, dual cisterns, and luxury living quarters above, with kitchenette, washer/dryer, full bath, and a versatile flex room ideal for a bedroom, gym or office. A dedicated cabana bath opens directly to the pool. Outdoor living is elevated with a stunning pool and spa, outdoor shower, landscape lighting, and expansive covered entertaining and parking. A 230-ft dock is included in the sale. A statement of power, design, and luxury—brand new, turnkey, and crafted for the UHNW buyer seeking an exceptional coastal masterpiece!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,167
Status:
Active
MLS#:
617652
Type:
Single Family
Subdivision:
Summerland Key Cove (25.0)
Lot size:
0.15 Acres
Year built:
1974
Courtesy: Berkshire Hathaway HomeServices Knight & Gardner Realty 305-294-5155
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ADDITIONAL INFORMATION

MOTIVATED SELLERS! The sea writes the script at this 3 bed, 3 bath oceanfront retreat on the most highly sought after neighborhoods on Summerland Key, and it stands in a class of its own. Western exposure delivers nightly golden-hour performances over the Atlantic, while deep-draft boating--among the best this side of the 7-Mile Bridge--begins right from your backyard. You'll love deep channel access to the Atlantic AND the Gulf of America! Inside, a wide-open floor plan crowned by cathedral ceilings, terracotta floors warming space throughout, and wall-to-wall sliders framing the Atlantic like a moving piece of art. A custom infinity-edge pool with in-water seating and sun shelf creates the perfect transition between home and horizon. Heated or chilled for year round comfort. The chef's kitchen impresses with elevated appliances including a 36' Wolf gas range, wine chiller, and twin beer taps. Relish the Keys breeze from the lanai and enjoy your morning coffee watching Summerland Cove wake up. End your day with alfresco dinning and famous Keys sunsets. A pre-FIRM lower level offers convenient guest quarters, an important Keys commodity. There's also flexible options for a pool house, tackle room, or storage - your choice. Plus a deep 1-car garage! A well maintained 10,000-lb boat lift--easily modified for larger vessels--completes the ideal waterfront lifestyle. Fuel your boat at Venture Out Marina less than two miles away from your seawall. With Niles Channel providing a 40-foot vertical bridge clearance, the highest in the Lower Keys, your Ocean or Gulf boating options are limitless. With just under 2,200 sq ft of living space- and backed by the security of a whole-house generator and whole-house water filter - this property embodies the rarest blend of comfort, craftsmanship, and blue-water possibility. Discover why Summerland Key remains the unsung hero of the Lower Keys--before opportunities like this are simply untouchable.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,565
Status:
Active
MLS#:
617590
Type:
Single Family
Subdivision:
Summerland Key Cove (25.0)
Lot size:
0.14 Acres
Year built:
2005
Courtesy: LAER Realty 561-429-2070
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ADDITIONAL INFORMATION

Hard to find a home in a Park like setting with a boat ramp right out the back door! 3 bedrooms 2 full baths and open living space. Summerland key cove is just 25 miles from Key West. Great place to raise a family or to retire. Be it you're a boater, pilot, fisherman or just want the open space to walk and enjoy privacy of the park. This quit Island neighborhood offers rare access to the laid-back Florida Keys. There is a possibility of being able to convert the lower level into an in-law apartment. This home has deeded reserved exclusive rights to the Park, Boat ramp and Pond PLEASE NOTE! OWNER FINANCING POSSIBLE!

Beds:
2
Baths:
2.00
Sq.Ft.:
861
Status:
Active
MLS#:
617604
Type:
Single Family
Subdivision:
Venture Out (23.0)
Lot size:
0.05 Acres
Year built:
1999
Courtesy: Lokation Real Estate 954-545-5583
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ADDITIONAL INFORMATION

VACATION RENTAL OPPORTUNITY - OPEN WATER VIEWS + 43' DOCK - 2BR/2BA 864 SQ. FT. Beautifully maintained 2-bedroom, 2-bath waterfront home offering open water views and excellent rental potential. This 864 sq. ft. property features a 43-foot dock with quick access to world-class boating, fishing, and diving in the Florida Keys. Ideal for investors or owners seeking a turn-key vacation rental property. PROPERTY FEATURES: • 864 sq. ft., efficient and well-designed floor plan • 2 Bedrooms / 2 Full Bathrooms • Open water views from the living area and outdoor spaces • 43' dock suitable for larger vessels • New hot water heater • Stainless steel appliances in updated kitchen • Protection from north winds for comfortable year-round outdoor enjoyment • Open-concept living/dining area ideal for guest appeal • Strong rental history potential in a desirable waterfront community Located minutes from top Keys attractions, marinas, and dining, this home offers excellent guest appeal and easy access to the best of island living. Perfect for buyers seeking a high-performing vacation rental or a personal getaway with income potential. Turn-key, income-ready, and perfectly positioned for the ultimate Keys lifestyle.

Beds:
4
Baths:
9.00
Sq.Ft.:
2,907
Status:
Active
MLS#:
A11913445
Type:
Single Family
Subdivision:
SUGARLOAF SHORES SEC F RE
Lot size:
0.29 Acres
Year built:
2022
Courtesy: American Caribbean Real Estate Carlos Lorenzo 786-251-4823
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ADDITIONAL INFORMATION

Step into your own exquisite waterfront sanctuary, Casa Del Mar, in Sugarloaf Shores is where clean, modern design meets relaxed Florida Keys ease. This beautifully built CBS home with impact windows and doors delivers 4 spacious bedrooms and 4.5 baths, wrapped in contemporary style and coastal charm. Inside, the heartbeat of the home is a true chef's kitchen featuring high-end appliances, huge quartz waterfall island, and an open-concept design that flows into bright living and dining spaces. Oversized terraces extend your outdoor living space, complete with a summer kitchen made for alfresco cooking under sunlit skies and moonlit nights. The primary suite is its own private retreat, an entire level devoted just to you. Enjoy a sun-washed deck, generous walk-in closet, and a balcony that frames shimmering water views. It's a Zen-zone where you can start and end the day in absolute calm. Boaters will love the serious waterfront access: a 100-ft seawall, a 25K lb boat lift, plus a floating dock/jet ski platform. From here, your days can go in any direction: fishing, sandbars, or just a quick ride out to open water. Outside, the heated pool and masterfully designed lounging and cooking areas create an effortless indoor-outdoor lifestyle. Just 20 minutes from Key West. This home strikes the perfect balance between turnkey serenity and easy access to everything that makes the Florida Keys so remarkable. Casa Del Mar is your luxury waterfront escape, ready to enjoy from day one.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,820
Status:
Active
MLS#:
617537
Type:
Single Family
Subdivision:
Jolly Roger Estates (28.5)
Lot size:
0.14 Acres
Year built:
1999
Courtesy: Coldwell Banker Schmitt Lower Keys (KW) 305-872-3050
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ADDITIONAL INFORMATION

Enjoy indoor-outdoor living with multiple inviting porches and excellent, oceanside boat access to the Atlantic and back-country. Features include a gated entry to covered parking, garage, fenced backyard, outdoor shower, tropical landscaping, 60 ft. canal-frontage, and a composite dock. Inside the ground-level foyer an oak staircase leads up to the main living area and continues to the upper-level. The main level of this Glenn Gray-designed, 1820 sq. ft. home has quartzite kitchen counters and abundant cabinets, comfortable living and dining areas, two bedrooms, one bath, washer/dryer, and tile floors. The upper level has the third, primary bedroom with a small refrigerator in the ensuite bath, and another porch with views of neighborhood views and glimpses of Newfound Harbor. A convenient second staircase leads from the large back porch to the back yard and dock. Hardie plank siding, metal roof; some of the upper-level windows are impact-resistant; doors and remaining windows have shutters. Solar-assisted water heater. Although not currently in use, the 2,500-gallon rainwater cistern provides the potential of supplemental water for plants and washing vehicles.

Beds:
6
Baths:
7.00
Sq.Ft.:
4,402
Status:
Active
MLS#:
617534
Type:
Single Family
Subdivision:
Sugarloaf Beach (17.0)
Lot size:
5.33 Acres
Year built:
1976
Courtesy: The Agency Florida Keys 305-916-1105
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ADDITIONAL INFORMATION

Rare Private Sandy Beach - Oceanfront Estate with endless open ocean views, just 30 minutes to Key West! This is a once-in-a-lifetime opportunity to own over 5 acres of sprawling oceanfrontage on exclusive Sugarloaf Beach, with over 500 feet of pristine sandy shoreline. Zoned Sub Urban Residential, this rare estate offers unmatched potential—create a private luxury compound, a boutique resort rental, or VIP luxury retreat. One of the few properties in the Lower Keys where lucrative nightly rentals are allowed with Special Vacation Rental Permits, this remarkable estate provides exceptional flexibility with ample room to expand. This estate has two existing homes - the main house has 4 bedrooms 4 bathrooms and the guest house has 2 bedrooms, 2 bathrooms and 1 half bath. Currently set up as two luxury nightly vacation rental homes! A new 430-foot dock is currently under construction with stainless steel pilings, stainless steel support beams and composite decking. Completion estimated in Feb/Mar included in the sale. The 5-foot draft welcomes larger boats! Arrange private charter pick ups at the dock for your guests. Enjoy world-class boating, fishing and diving on your doorstep. American Shoal Lighthouse is only 5 miles directly in front of this spectacular property. Located on highly desirable Lower Sugarloaf Key in the Lower Keys, only 30 minutes to Key West, this hidden sanctuary is an unmatched offering for a discerning buyer seeking privacy, scale, and re-development potential. Nothing comparable exists in the area! Sugarloaf Beach remains one of the most coveted and rare stretches of beachfront in the Florida Keys. Whether you envision a secluded tropical retreat, a boutique luxury rental, or a visionary new oceanfront compound, this property is incredible with amazing potential to redefine with your personal touch. Opportunities like this come once in a lifetime. Take your private tour today and unlock the full potential of this iconic oceanfront estate!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,284
Status:
Active
MLS#:
617545
Type:
Single Family
Subdivision:
Cutthroat Harbor Est (23.0)
Lot size:
0.14 Acres
Year built:
1989
Courtesy: EXP Realty LLC 888-883-8509
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ADDITIONAL INFORMATION

Welcome home to this impressively spacious 2-bedroom, 2-bath Keys retreat, offering an elevated blend of comfort, functionality, and coastal living. The outdoor living space is a dream with a new concrete pool & waterfall feature, 12k lb boat lift, 60' concrete seawall, & an expansive 10 foot deep back porch (total of nearly 700 sq ft of porches), all perfect for outdoor dining, lounging, & savoring tropical breezes year-round. This home is a dream for boaters with quick easy access to Cudjoe Bay & the open water, favorite sandbars, and world class fishing & diving. Inside, you'll find upgraded stainless steel appliances, granite waterfall counters, a cedar closet in the primary suite, and beautiful slate flooring throughout, adding modern elegance to the easy living layout. Additional features include plantation shutters throughout, Miami-Dade rated accordion shutters, a hip metal roof, excellent insurance rates, plus transferable flood insurance for added savings. The nearly 700 sq ft enclosed ground level offers an extra-large storage area, workshop, or game room, with plenty of space for an outdoor kitchen & lots of covered parking, while tropical landscaping frames the private, serene atmosphere. With thoughtful upgrades throughout & every amenity in place, this property is turn-key & ready for you to enjoy the incredible Florida Keys lifestyle.

Beds:
2
Baths:
1.00
Sq.Ft.:
806
Status:
Active
MLS#:
617499
Type:
Single Family
Subdivision:
Venture Out (23.0)
Lot size:
0.04 Acres
Year built:
2002
Courtesy: RE/MAX Keys Connection (KW) 305-296-1400
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ADDITIONAL INFORMATION

********Nightly Licensed Transient Rental!!!******** This amazing, two bedroom / one bathroom, open water front, nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rental license. The floor plan makes the open water views as its main focus. Cook the catch of the day overlooking the waters that you just caught that prized fish in. Sit back and watch your friends and family enjoy those waters with your favorite beverage in hand, and enjoy those fruits of your hard labor. This home is built with easy maintenance in mind, don't worry just enjoy. This home does come with approved engineered plans to build a second bathroom if needed. There is covered parking and a covered storage for all your needs. Just sit back and enjoy this amazing location. This one is location, location, location! Enjoy tropical breezes and island living in this amenity-rich resort-style neighborhood. Venture Out features 24-hour gated security, an oceanfront heated pool, hot tub, fuel station, marina, boat ramp, tennis and pickleball courts, a waterfront picnic pavilion, and much more. Located just 19 miles from Key West and minutes from world-class fishing, diving, and boating, this home offers everything the Keys lifestyle promises - sun, sea, and serenity. Call today for a showing!

Beds:
5
Baths:
3.00
Sq.Ft.:
1,903
Status:
Active
MLS#:
617496
Type:
Single Family
Subdivision:
Cudjoe Acres (21.5)
Lot size:
1.57 Acres
Year built:
1986
Courtesy: Berkshire Hathaway HomeServices Knight & Gardner Realty 305-294-5155
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ADDITIONAL INFORMATION

TRANSIENT LICENSE FOR NIGHTLY RENTALS BRINGING IN 250k+! WITH OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! THIS PROPERTY IS A ONE OF A KIND! A TRUE ''UNICORN!'' Turnkey Vacation Rental with 4 bedrooms and 2 baths in Main House which is a charming and OLD FLORIDA KEYS STYLE PROPERTY! Privacy, lush vegetation, stunning Open water views from the balconies from almost every room! Original hardwood floor, tons of character and warmth in this lovely home! Large resort style pool with plenty of poolside space for lounging and taking up the gorgeous Florida keys sunshine. Plus a solid concrete hurricane bunker with an upper level bedroom, bath, and kitchenette and more views! Perfect for grounds keeper or property manager. Walk thru the property grounds and take in all of the magic it has to offer! With over 200 species of fruit, and palm trees, and tropical flowers, as well as Fresh coconuts! Fully fenced in so perfect for the family or guests pets. With 2 private entrances. Get lost in the tranquility of this Gem and make it your own private estate or an excellent investment with tons of income potential! Leave as is, or build additional casitas or consider the potential of the additional lots. Historically brought in average of 220K in rental income annually. This year projection is closer to 250-300k. This one won't last long as this is a great price considering all you are getting! A solid INVESTMENT with an excellent ROI! Not on the water but has the stunning open water views and also has access at end of Colson to put in kayaks and paddle boards. Plenty of space to keep your RV and boat trailers and put your boat in the water at nearby ramps, 1 Ocean side and 1 Gulf side. Vacationers love this property! Excellent reviews and comments are feels like 'old Florida Keys' and 'Tropical Oasis Hidden Away'. Buy this and start making money day 1!

Beds:
2
Baths:
2.00
Sq.Ft.:
640
Status:
Active
MLS#:
617476
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.04 Acres
Year built:
2018
Courtesy: Coldwell Banker Schmitt RE Co. 305-872-3050
View additional info

ADDITIONAL INFORMATION

Luxurious Waterfront Living - Welcome to your perfect coastal oasis in the sought-after community of Venture Out! This contemporary high-rise boasts million-dollar views from every angle, including a screened patio for ultimate enjoyment. With an outside elevator providing easy access, this stunning home features a serene primary suite with stylish decor and a beautiful walk-in shower in the bathroom. The second bedroom is ideal for a small bunk bed or a cozy office, and the guest bathroom has a convenient walk-in shower and laundry area. The kitchen is fully equipped with a bar and stainless-steel appliances, and the open-floor plan allows for seamless entertainment in the living area. Keep your boat at the 37-foot concrete seawall and take advantage of the prime location for offshore fishing and world-class diving. Venture Out offers exclusive amenities such as a large, heated pool, marina, boat ramp, and courts for various sports like tennis, bocce ball, basketball, and pickleball. This property would also be the perfect investment property for daily, weekly, or monthly rentals. Do not miss the chance to join this vibrant community and live the ultimate island lifestyle!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,204
Status:
Active
MLS#:
617468
Type:
Single Family
Subdivision:
Summerland Key Cove (25.0)
Lot size:
0.14 Acres
Year built:
1987
Courtesy: Keller Williams Key West Compass Realty 305-292-0020
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ADDITIONAL INFORMATION

HOME is where the BOAT IS! Discover effortless access to world-class boating on one of the widest, deepest, and most desirable canals in the Lower Keys. Your 17,000-lb boat lift sits on a pristine flow-through canal—meaning clean, clear water and quick access. In just minutes, you can be fishing the Atlantic, exploring the backcountry in the Gulf, or gliding toward a perfect Key West sunset. This concrete block, 3-bedroom, 2-bath stilted home on Summerland Key offers the ideal blend of low-maintenance living and coastal comfort. Exterior upkeep is a breeze with pea gravel landscaping and a new 6' privacy fence. A spacious downstairs storage room provides plenty of space for all your gear, while the screened-in upstairs balcony with hot tub creates the perfect spot to unwind after a day on the water. Just installed, a new meter box with 200 amps to the meter. All this, and it's one of the most affordable stilted waterfront homes in Summerland Cove—a rare opportunity in an established boating community. Don't miss your chance to own a true Keys lifestyle home!

Beds:
2
Baths:
2.00
Sq.Ft.:
864
Status:
Active
MLS#:
617465
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.05 Acres
Year built:
1999
Courtesy: Bluescape Real Estate 305-203-2537
View additional info

ADDITIONAL INFORMATION

Introducing an exceptional waterfront investment opportunity in the heart of the Florida Keys! This beautifully remodeled waterfront home in the highly desirable gated community of Venture Out on Cudjoe Key is zoned for minimum one-day vacation rentals, making it an ideal choice for investors or those seeking a turnkey coastal retreat. Step inside and you'll immediately appreciate the home's modern elegance paired with classic coastal charm. This 2-bedroom, 2-bath residence was completely renovated in 2020, offering stylish, contemporary finishes and comfortable functionality throughout. Enjoy direct boating access from your private seawall to both the Atlantic Ocean and the Gulf of Mexico—perfect for fishing, exploring, or simply taking in the natural beauty of the Lower Keys. The spacious kitchen serves as the centerpiece of the home, featuring newer appliances and a thoughtful layout ideal for entertaining. The kitchen flows seamlessly into a bright dining area and out to the covered patio giving an inviting outdoor space perfect for relaxing and enjoying stunning Keys sunsets. Venture Out offers an impressive list of amenities, including a heated oceanside pool, marina and boat launch, tennis courts, community events from November through April, gated security and well-maintained common areas. This property is offered fully furnished, providing a true turn-key opportunity. A newer metal roof adds durability and peace of mind, ensuring the home is ready for your immediate enjoyment. Whether you're looking for an income-producing rental or a personal Keys getaway, this waterfront gem delivers the lifestyle you've been dreaming of.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,766
Status:
Active
MLS#:
617413
Type:
Single Family
Subdivision:
Summerland Key Cove (25.0)
Lot size:
0.14 Acres
Year built:
1970
Courtesy: The Agency Florida Keys 305-916-1105
View additional info

ADDITIONAL INFORMATION

Discover the Ultimate in Luxury Waterfront Living at This Prime Oceanfront Tropical Gem in Summerland Key.Located in the prestigious community of Summerland Cove—just 30 minutes from Key West—this exceptional deep-water oceanfront estate offers the perfect blend of privacy, beauty, and unparalleled boating access. Completely rebuilt in 2006, this elevated 4BR/3.5BA residence spans 2,766 sq. ft. and is designed to showcase sweeping, unobstructed views of the Atlantic. The grand open living and entertaining space features soaring ceilings and walls of glass that frame endless turquoise water vistas, creating an airy coastal ambiance throughout. Step outside to your own private resort with a sparkling oceanfront pool and spa, surrounded by expansive decks ideal for sunset cocktails or gatherings with family and friends. A rare concrete dock with a cut-in boat slip provides quick, direct access to world-class fishing, diving, and boating—an extraordinary feature highly coveted in the Florida Keys. Outdoor living is elevated with a poolside summer kitchen, multiple lounging decks, and panoramic views in every direction. Upstairs, the spacious primary suite offers breathtaking ocean views, a private balcony, and the ultimate retreat for rest and relaxation. Additional features include impact windows and doors, a metal roof, and a chef's kitchen with granite countertops and stainless steel appliances. This is Luxury Coastal Living at its Finest—a premier oceanfront home offering rare amenities, deepwater access, and unforgettable views in one of the Florida Keys' most sought-after communities.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,232
Status:
Active
MLS#:
617402
Type:
Single Family
Subdivision:
Dobie's Sub (24.0)
Lot size:
0.17 Acres
Year built:
2002
Courtesy: Island Real Estate Company Florida Keys 305-395-0696
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ADDITIONAL INFORMATION

Oceanfront retreat with sandy beach, protected dockage & direct access to the Ocean & Gulf. Wake each morning to breathtaking Atlantic sunrises and unwind beneath glowing sunsets in this custom-built, two-story CBS oceanfront home. Tucked away on a private street shared by only four residences, this exceptional island inspired sanctuary offers panoramic ocean views, unmatched privacy, and the quintessential Florida Keys lifestyle. The thoughtfully designed home features bright, open-concept living space. Expansive windows, oversized glass doors, and multiple covered porches that flood the interior with natural light while showcasing sweeping ocean views. The chef's kitchen includes stainless steel appliances, tall custom wood cabinetry and generous granite counter space-perfect for entertaining. Outdoors, enjoy your own private resort setting with a custom built in ground lagoon-style pool, cascading waterfall, hot tub, lush mature tropical landscaping, fruit trees, butterfly plants and a poolside tiki hut. Relax under the palms on the beach, or entertain on beautifully paved travertine grounds. For boaters, this property is a rare gem. The 62 ft concrete dock offers quick, direct access to both the Ocean and Gulf, along with protected dockage. Features a new 17,000 LB boat lift, 3 additional davits, and approximately 300 ft of bay bottom frontage. This extraordinary oceanfront offering seamlessly blends privacy, tropical elegance, boating convenience, and stunning sunrise-to-sunset views. Walking & biking-Florida Keys Heritage Trail just foot steps away. A private airstrip on the island, excellent local restaurants, and close proximity to both Key West & Marathon make this home ideal for year-round living or a luxurious island escape.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,605
Status:
Active
MLS#:
617353
Type:
Single Family
Subdivision:
Sugarloaf Shores (17.0)
Lot size:
0.64 Acres
Year built:
1973
Courtesy: Ocean Sotheby's International Realty 305-294-1117
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ADDITIONAL INFORMATION

Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy. Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're exploring by paddleboard or kayak, or heading out on your boat to world-class fishing and diving, this location makes it effortless. The backyard is designed for relaxation and connection, featuring a pool, spa, and multiple outdoor patio areas, all surrounded by lush, mature tropical landscaping. Inside, the home features a renovated kitchen, bright open living spaces, and a large enclosed back porch that extends your living area and overlooks the pool, spa, and canal. With four bedrooms, generous square footage, and seamless indoor-outdoor flow, the home is ideal as a primary residence, seasonal getaway, or investment property with tremendous upside. Located just minutes from Key West yet surrounded by the peace and natural beauty of Sugarloaf, this property offers the best of both worlds—space, privacy, and direct water access that's hard to find, along with the freedom to create your ideal island retreat.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,994
Status:
Active
MLS#:
R11141078
Type:
Single Family
Subdivision:
BREEZESWEPT BEACH ESTS
Lot size:
0.14 Acres
Year built:
1987
A broker reciprocity listing Courtesy: William Raveis Real Estate 561-576-7085
View additional info

ADDITIONAL INFORMATION

Tropical Keys Oasis -- Waterfront Luxury Living -- Come experience this one-of-a-kind tropical oasis that feels like living at a Keys resort. Surrounded by lush landscaping, vibrant grass is the backdrop for nine coconut palms, five banana trees, two mango trees, and an avocado tree, this property bursts with natural beauty. Vibrant bougainvillea archways create a stunning entry to one of the most exquisitely landscaped homes on the island. Enjoy 60 feet of waterfront with an expansive maintenance free deck, a 15,000-lb boat lift for up to a 33-foot boat and a drop dock perfect for swimming in the lagoon or launching kayaks. Outdoor living is elevated to the next level--exactly what you'd expect in the Florida Keys. Inside, discover a newly renovated beautiful 4-bedroom

Beds:
6
Baths:
5.00
Sq.Ft.:
5,208
Status:
Active
MLS#:
617329
Type:
Single Family
Subdivision:
Sugarloaf Beach (17.0)
Lot size:
2.33 Acres
Year built:
1959
Courtesy: The Agency Florida Keys 305-916-1105
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ADDITIONAL INFORMATION

Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach — a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and diving. A protected 6-boat basin with room for extra boats is the centerpiece of the waterfront, complete with 25K and 16K lifts, a boat ramp, sandy beach, lookout point, and composite observation deck. After a day on the water, unwind in the lagoon-style saltwater pool with heater, chiller, and custom water features. The expansive tiki bar includes TVs, True refrigerator/freezer drawers, and an ice machine—perfect for effortless outdoor entertaining. Additional features include a firepit, private sandy beach, and a full outdoor kitchen equipped with built-in BBQ, Viking appliances, and True refrigeration. The upper level offers a bright and open Great Room with sweeping ocean views, a spacious dining area, and a chef's kitchen with stainless appliances. Two covered verandas provide ideal spaces for taking in the breezes and panoramic vistas. The primary suite features an office, en suite bath, walk-in closet with laundry, sunroom, and loft. Two additional upstairs guest rooms comfortably accommodate visitors, while the separate downstairs living area offers three more guest bedrooms for privacy and flexibility. Designed for hosting and convenience, the home is equipped with a Sonos sound system, property-wide Wi-Fi, abundant storage, a two-car garage with fishing lockers, and generous parking along a winding paver driveway. Lush, mature landscaping surrounds the property, creating a serene and secluded Sugarloaf Key retreat. Call for more information today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,500
Status:
Active
MLS#:
617297
Type:
Single Family
Subdivision:
Ramrod Shores (27.0)
Lot size:
0.14 Acres
Year built:
2023
Courtesy: Keller Williams Key West Compass Realty 305-292-0020
View additional info

ADDITIONAL INFORMATION

Don't miss the chance to own this exceptional piece of paradise—schedule a private showing today! Be the first to call this stunning, newly constructed Affinity-built home yours! Located in desirable Ramrod Key, this energy-efficient 3-bedroom, 2-bathroom residence boasts premium quality throughout. Featuring high-end fixtures, Pella impact-resistant windows and doors, and thoughtful craftsmanship, this home is built to last. The spacious open floor plan is designed for modern living, with a chef's kitchen showcasing top-of-the-line appliances and custom cabinetry. Each bedroom offers ample space and natural light, while the primary suite provides a private oasis with a spa-like bathroom and luxurious walk-in closet. Step outside to your private oasis—a beautiful custom cement pool with both heating and chilling capabilities, perfect for year-round enjoyment. Whether you're cooling off in the summer or warming up in the winter, the pool offers the ultimate relaxation. With a pristine swimming canal. This never-lived-in home is the epitome of island luxury, combining cutting-edge energy efficiency with stylish design. Don't miss this opportunity to own a piece of paradise in the Florida Keys! Schedule your private tour today.

Beds:
2
Baths:
2.00
Sq.Ft.:
860
Status:
Active
MLS#:
617289
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.05 Acres
Year built:
2008
Courtesy: Bluescape Real Estate 305-203-2537
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ADDITIONAL INFORMATION

Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day on the water. A resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area with tiki huts and more! Cruise around the property in your golf cart to the community store or to join in on the numerous community activities. Live with peace of mind in an exclusive gated community which adds a sense of security and prestige. This home is ready for you to move in and enjoy! Don't miss this rare opportunity to own a piece of paradise! Nightly Rentals Allowed! Plenty of potential for rental income.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,500
Status:
Active
MLS#:
617216
Type:
Single Family
Subdivision:
Indian Mound Estates (19.5)
Lot size:
0.24 Acres
Year built:
1968
Courtesy: Meyer and Boumerhi Realty LLC 305-587-0268
View additional info

ADDITIONAL INFORMATION

Motivated seller! Bring all Reasonable offers 2 bedrooms, 1.5 baths with a 500sq ft screened lanai in the main building. There are 2 additional buildings that could be used as offices or bedrooms. Custom Pool with jacuzzi and swim jet. Completely remodeled in 2020 with new roof, new A/C. Located in the established Indian Mound Estates neighborhood w/ Access to private boat ramp with cabana and beach. School and nature preserve is within walking distance. This property is surrounded by lots of tropical Landscaping and privacy fencing. Many upgrades including automated lighting, huge outdoor shower, custom storage cabinets, custom concrete decks, terrazzio flooring, patios and a three bowl sink fish cleaning station. There are adjacent lots available to purchase for RV Boats and Storage. Annual flood, and wind insurance approximately $8500

Beds:
3
Baths:
2.00
Sq.Ft.:
1,851
Status:
Active
MLS#:
617442
Type:
Single Family
Subdivision:
Cudjoe Gardens (21.0)
Lot size:
0.41 Acres
Year built:
1968
Courtesy: Ocean Sotheby's International Realty 305-294-1117
View additional info

ADDITIONAL INFORMATION

In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping — buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys for. Inside, the home has been thoughtfully updated: custom kitchen cabinets, granite countertops, new appliances, new electric, propane, all-PVC plumbing (no cast iron), renovated bath, custom closet, impact doors and windows, and split A/C's. A whole-house generator adds peace of mind. Set along a quiet street in prestigious Cudjoe Gardens, this property also includes a beautifully landscaped 8,000 sq. ft. canalfront lot directly across the road, offering protected deep-water access just three houses from open water. Featuring a new 80-foot concrete dock, a 12K hydraulic lift, two 5K davits, and a jet ski dock. With a 4 foot control depth it's ideal for large vessels and avid boaters seeking effortless ocean access. The professional landscaping mirrors the elegance of the main residence, creating a cohesive tropical aesthetic on both sides. With big-boat capability and endless possibilities — including the potential to build — this rare combination of oceanfront living and deep-water convenience defines the ultimate Keys lifestyle. A move-in-ready, renovated home in Cudjoe Gardens with its own separate boating compound is almost never available — this one delivers the serene Keys lifestyle from oceanfront to canalfront. Perfect for your ''Key West to Key Largo'' buyers who want boating without giving up privacy.

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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.




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

    $1,100,000
    26.6%
    change since last quarter
  • # Active listings

    281
    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