Sugarloaf, FL Homes for Sale

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  /125

  $10,700,000

  • 6 Beds
  • 8 Baths
  • 4,894 Sq Ft

  1041 Buttonwood Dr E, Sugarloaf Key, FL 33042

  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

  Lisa Swanson The Agency Florida Keys

  1041 Buttonwood Dr E, Sugarloaf Key, FL 33042
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  /75

  $915,000 Open Sun 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042

  This is the house for your boat!ENDLESS OCEANFRONT LIVING - 47' SEAWALLWake up every morning to sweeping sunrises & unobstructed views of the turquoise Atlantic at this extraordinary one-of-a-kind, oceanfront residence. The 'Crown Jewel of the Ocean' located just 19 miles from Key West, this beautifully appointed 2-bedroom, 2-bath mid-rise home offers front-row seats to the water & an unmatched

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
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  /17

  $969,000

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft

  17171 Seagrape Ln, Summerland Key, FL 33042

  RARE OPPORTUNITY HERE! Seller IS the listing Agent!! Let's make a deal! This home is perfect for a DIY or Builder. Bring your imagination as it's located in very desirable location of Sugarloaf Shores where homes are over 2++ million dollars. It just needs a makeover but has great bones and many things you won't get now. Full 2 car garage with impact doors and shop. Legal downstairs bath. Large

  Marie Howe Century 21 Circle - Key West

  17171 Seagrape Ln, Summerland Key, FL 33042
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  /42

  $650,000

  • Land

  22948 Drake Ln, Summerland Key, FL 33042

  Boater/Angler special: 70-foot concrete seawall features hard-to-find boat slip/basin, plus 10,000-pound boat lift . This canal front-vacant lot is ROGO exempt and ready to build on. It corners Drake Lane's dead end and is second from Cudjoe Bay's open water. Perfect location for new build. Previous house removed and lot is ready for your vision. Electric was in place, buyer to verify FKAA

  Barbara Bowers Preferred Properties (KW)

  22948 Drake Ln, Summerland Key, FL 33042
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  /3

  $135,000

  • Land

  19617 Date Palm Dr, Sugarloaf Key, FL 33042

  Best priced lot in popular Upper Sugarloaf Key and priced for immediate sale! Take advantage of this opportunity to develop this larger 150 x 100 Tier III platted lot (infill lot located in a developed subdivision with adequate infrastructure). With its prime location and desirable features, this property is a rare find in today's market. Convenient to the community boat ramp and near the

  Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

  19617 Date Palm Dr, Sugarloaf Key, FL 33042
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  /46

  $419,000

  • 2 Beds
  • 1 Bath
  • 833 Sq Ft

  701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042

  This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 1 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
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  /19

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,010 Sq Ft

  4 Shore Dr, Key West, FL 33040

  Million dollar views! Ocean and Gulf views make this an affordable waterfront gem. Situated in the quiet and peaceful Bay Point neighborhood, this home is only 17 miles from Key West allowing quick city access and return to waterfront bliss. This Keys-style fish camp offers a waterfront manufactured home with 2 bedrooms and 2 baths. The side yard was once an orchid house and could be returned as

  Elizabeth Jolin Coldwell Banker Schmitt Islamorada

  4 Shore Dr, Key West, FL 33040
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  /4

  $100,000

  • Land
  • 1.01 Acres
  • $99,010 per Acre

  0 Acosta Rd, Summerland Key, FL 33042

  Vacant 1.01-acre parcel on Acosta Trail in Upper Sugarloaf Key, Monroe County, FL. Approx. 20 miles to Key West, 10 miles to Big Pine Key, and 5 miles to Cudjoe Key. Unimproved land offering future development or investment potential in the Lower Florida Keys. Additional 1.01-acre lot on Mira Rd (behind subject property) also available for sale. Buyer to verify zoning, ROGO status, flood zone,

  0 Acosta Rd, Summerland Key, FL 33042
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  /77

  $450,000

  • Land

  701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042

  Ocean View Canal Front RV Lot in Venture Out - 35' Concrete SeawallBuild, park, invest, or simply pull in and start living the Keys lifestyle. This 35' x 69' beautiful, waterfront RV lot in the private, gated community of Venture Out offers ocean views, a 35' concrete seawall, and direct boating access to both the Atlantic and backcountry waters.The lot features a concrete pad and walkway,

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
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  /56

  $579,900

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042

  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

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
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  /39

  $4,375,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,103 Sq Ft

  231 E Shore Dr Unit 6, Key West, FL 33040

  Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available—each starting at $4 million—this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West. Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5

  Stephanie Muzzillo Serhant

  231 E Shore Dr Unit 6, Key West, FL 33040
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  /5

  $24,500

  • Land
  • 0.5 Acre
  • $49,000 per Acre

  2351 Alamanda Dr, Sugarloaf Shores, FL 33042

  Excellent Location within Indian Lake Estates, close to club house! Enjoy inexpensive golf on an improved golf course and remodeled Club house! Have a Great Lunch on the outside Patio at the 19th Hole! Enjoy a vast view in a peaceful setting! You will be sold! Plus you have a 7500 Acre Lake to fish for large mouth Bass! Enjoy the tranquility and being able to see the stars again in this rural

  Robert Burns Allstar Realty Inc

  2351 Alamanda Dr, Sugarloaf Shores, FL 33042
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  /49

  $669,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042

  OCEANFRONT TRANSIENT RENTAL IN VENTURE OUT - CUDJOE KEYAmazing open water views of the sparkling Atlantic set the tone the moment you arrive. From this premier waterfront location, you'll enjoy sweeping vistas of the marina, lagoon, Tiki hut, and the iconic Bird Point sanctuary. Sunrise glows over endless blue water, creating a peaceful and ever-changing coastal backdrop.Positioned on a 35-foot

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
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  /5

  $324,999

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  230 Yardarm Rd, Summerland Key, FL 33042

  Joseph Ordini Keller Williams Key West Compass Realty

  230 Yardarm Rd, Summerland Key, FL 33042
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  /83

  $4,400,000

  • 4 Beds
  • 4.5 Baths
  • 2,907 Sq Ft

  16745 Tamarind Rd, Sugarloaf Shores, FL 33042

  Step into your own waterfront sanctuary, 'Casa Del Mar' in prestigious Sugarloaf Shores on Lower Sugarloaf Key, where clean, modern design meets unmistakable Florida Keys ease. This beautifully built CBS home with impact windows delivers 4 spacious bedrooms and 4.5 baths, wrapped in contemporary style and coastal charm.Inside, the heart of the home is a true chef's kitchen with high-end

  Carlos Lorenzo American Caribbean Real Estate, Christie's International Real Estate

  16745 Tamarind Rd, Sugarloaf Shores, FL 33042
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  /44

  $869,000 Open Sun 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  154 Cutthroat Dr, Summerland Key, FL 33042

  Beautifully updated 2 bedroom, 2 bathroom home with spacious covered, screened porch overlooking the canal with access to both the Gulf of Mexico and the Atlantic Ocean in just a few minutes. With pride of ownership, this house has been upgraded and well maintained. Many upgrades include: 2024 - New fence with double gates and an entrance gate, gutters, landscaping, tile flooring, freshly painted

  Pamela Stangler Expert Realty LLC

  154 Cutthroat Dr, Summerland Key, FL 33042
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  /30

  $460,000

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

  Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
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  /75

  $3,500,000

  • 4 Beds
  • 3 Baths
  • 2,812 Sq Ft

  16805 Tamarind Rd, Summerland Key, FL 33042

  OPEN WATER ELEGANCE on prestigious Southpoint, Sugarloaf Key. This exceptional 4-bedroom, 3-bath concrete waterfront residence captures breathtaking open water views from nearly every room and delivers the ultimate Florida Keys lifestyle.Positioned on a generous, beautifully landscaped lot with mature palms and established tropical greenery, the property welcomes you with a paved circular

  Lisa Swanson The Agency Florida Keys

  16805 Tamarind Rd, Summerland Key, FL 33042
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  /25

  $569,700

  • 2 Beds
  • 1 Bath
  • 718 Sq Ft

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042

  Licensed nightly rental. Brand new raised Sea Wall!! Discover island living at 701 Spanish Main Dr, Unit 335 in Cudjoe Key, FL. 2Bd/1Ba successful vacation rental located in a premium location on the water with open water views and features a 35' concrete seawall for docking a boat. Dock is equipped with dock posts, cleats, water, and storage. Large patio space to enjoy paradise overlooking the

  Sarah Dolson Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042
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  /2

  $55,000

  • Land

  0 Vacant Land Unit 618301, Sugarloaf Key, FL 33042

  ROGO land dedication lot worth 2 points with paperwork completed and Monroe County letter of eligibility on file. No hidden expenses with this lot. Cost-effective way to get your permit faster! This lot is not buildable and is sold for land dedication purposes only.

  Nate Meyer Meyer and Boumerhi Realty LLC

  0 Vacant Land Unit 618301, Sugarloaf Key, FL 33042
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  /46

  $487,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

  Seller is motivated!Coastal Charm Meets Modern Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key--a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright and airy

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
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  /43

  $1,299,000

  • 3 Beds
  • 2 Baths
  • 1,968 Sq Ft

  19267 Hansen Trail, Summerland Key, FL 33042

  Set on over an acre of land, 19267 Hansen Trail is a truly one-of-a-kind property where modern luxury meets refined homestead living.Offering nearly 2,000 square feet of beautifully remodeled living space, this 3-bedroom, 2-bathroom residence has been thoughtfully upgraded with high-end finishes and smart-home conveniences throughout.The open-concept design creates a seamless flow from the

  Justyn Ewald Expert Realty LLC (HQ)

  19267 Hansen Trail, Summerland Key, FL 33042
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  /38

  $1,490,000

  • 2 Beds
  • 2 Baths
  • 1,127 Sq Ft

  1113 de Lussan Ln, Summerland Key, FL 33042

  Breathtaking Open Water Home in Cudjoe Key - Comes FULLY FURNISHED!Welcome to paradise! This stunning 2-bedroom, 2-bath home captures magnificent open water views and embodies the ultimate Florida Keys lifestyle.Main Living Area:Step inside to an open-concept kitchen, living room, and dining area bathed in natural light. Every detail is designed to highlight the beauty of the surrounding water

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  1113 de Lussan Ln, Summerland Key, FL 33042
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  /52

  $410,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

  Vacation Rental Property with Transient Rentals Allowed! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen,

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
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  /49

  $2,100,000

  • 4 Beds
  • 3 Baths
  • 2,440 Sq Ft

  22542 Jolly Roger Dr, Summerland Key, FL 33042

  This striking 4-bedroom, 3-bathroom home is a testament to coastal architecture, blending rustic design with open, light-filled living spaces that showcase a breathtaking oceanfront setting. Situated on a double lot totaling .32 acres, the property offers an impressive 120 feet of frontage overlooking Cudjoe Bay—creating a rare and commanding presence along the shoreline.Broad covered

  Lauren Dunn Coldwell Banker Schmitt R.E.

  22542 Jolly Roger Dr, Summerland Key, FL 33042
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  /16

  $989,999

  • 3 Beds
  • 3 Baths
  • 960 Sq Ft

  22961 John Avery Ln, Summerland Key, FL 33042

  Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower

  Rayden Vega Casa Miami Real Estate

  22961 John Avery Ln, Summerland Key, FL 33042
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  /4

  $100,000

  • Land
  • 1.01 Acres
  • $99,010 per Acre

  0 Mira Rd, Sugerloaf, FL 33042

  Vacant 1.01-acre parcel on Mira Rd in Upper Sugarloaf Key, Monroe County, FL. Approx. 20 miles to Key West, 10 miles to Big Pine Key, 5 miles to Cudjoe Key, and a short drive to local restaurants, marinas, and waterfront attractions throughout the Lower Florida Keys. Unimproved land offering future development or investment potential. Adjacent 1.01-acre lot on Acosta Trail (in front of subject

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  0 Mira Rd, Sugerloaf, FL 33042
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  /6

  $225,000

  • Land

  124 Cutthroat Dr, Cudjoe Key, FL 33042

  Canal front lot in beautiful Cutthroat Harbor Estates. Excellent opportunity to be on the water in a great location. Property currently has concrete columns and slab in place. Possible short sale.

  Jimmy Lane Island Life Realty Experts

  124 Cutthroat Dr, Cudjoe Key, FL 33042
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  /32

  $1,649,000

  • 3 Beds
  • 2 Baths
  • 2,144 Sq Ft

  1151 Sugarloaf Blvd, Summerland Key, FL 33042

  Truly unique and private estate property on the desired Sugarloaf Blvd. in Sugarloaf Shores. Ground level CBS house sits on 2 waterfront lots. Totaling over 1.3 acres of land and approx. 400 ft. of canal front. Amazing view up the canal to the open water. The large floor plan featuring 3 bedrooms, 2 baths, den/office and fireplace. Kitchen has stainless appliances, quartz countertops and lots of

  Wendy Zintsmaster Truman & Co. (KW)

  1151 Sugarloaf Blvd, Summerland Key, FL 33042
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  /21

  $575,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042

  Affordable piece of paradise! Fully furnished, move in ready, open concept, bright and airy, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you'll be amazed. All new furnishings included! It has a very large kitchen and living area that looks out over the canal, with sliding glass doors out on to the newly painted deck. Minisplits in each room that cool, heat and

  Mary Conklin Action Keys Realty of the Lower FL Keys LLC

  701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
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  /64

  $840,000

  • 3 Beds
  • 3 Baths
  • 1,592 Sq Ft

  19611 Tequesta St, Summerland Key, FL 33042

  Relaxed living at its finest on Sugarloaf Key. This peacefully landscaped 10,000 sq ft double parcel offers a 3 bedroom, 2.5 bath, 1564 sq ft stilted home, with in ground pool, generous off street parking, storage and sheds. Enjoy your morning coffee or afternoon cocktail on one of 3 sprawling porches this home offers. This open concept home provides endless natural light, high ceilings, wooden

  Jessica Forsythe eXp Realty LLC

  19611 Tequesta St, Summerland Key, FL 33042
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  /51

  $910,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  813 Hawksbill Ln, Summerland Key, FL 33042

  Charming 2BR/2BA Keys home on Upper Sugarloaf. FULL HOUSE GENERATOR WITH TRANSFER SWITCH,Built on sturdy concrete pilings with Hardie board siding and a metal roof, Large workshop, storage space on first level with Laundry room, this three-story retreat of island living. Inside, you’ll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys

  Guadalupe Perez Douglas Elliman

  813 Hawksbill Ln, Summerland Key, FL 33042
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  /11

  $480,000

  • Land

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

  Discover the ultimate escape! This highly sought-after waterfront RV lot offers everything the coastal enthusiast dreams of, combining luxury amenities with unparalleled nautical access. Located on a wide street this lot is easily accessible for larger RV's and 5th wheels. Features a newer separate concrete parking area for your vehicle and a large level concrete pad for the Rv. Comes complete

  Carmen Brake Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
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  /26

  $259,000

  • 2 Beds
  • 1 Bath
  • 664 Sq Ft

  701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042

  2 bedroom 1 bath mobile home located at 701 Spanish Main Dr Lot #457 Cudjoe Key FL in Venture Out, an individually owned residential condominium community with 24hr gated security located 20 miles from world famous Key West. This mobile home is on a non-waterfront lot w/ a peek-a-boo view of eastern facing canal. Other ideal use as a ROGO exempt buildable lot for a new elevated home. No age

  Deirdre Praught Florida Keys Realty, Inc.

  701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042
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  /86

  $1,795,000

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft

  16640 Cypress Rd, Summerland Key, FL 33042

  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

  Lisa Swanson The Agency Florida Keys

  16640 Cypress Rd, Summerland Key, FL 33042
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  /40

  $300,000

  • Land

  701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042

  Transient (1 Day Rental) Rentals Opportunity in the Lower Keys! Buildable RV Lot. Nestled in a serene, well-maintained community, this RV lot offers the ideal spot for your home on wheels, or the opportunity to build your dream home. Boasting a private lot with new landscaping, pea rock and concrete parking pad and is equipped with full hookups including water, sewer, and 30, and 50 amp electric

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042

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