Sugarloaf, FL Homes for Sale

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  $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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  $1,099,000

  • 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, all new impact windows and doors, and smart-home conveniences throughout. The open-concept design

  Justyn Ewald Expert Realty LLC (HQ)

  19267 Hansen Trail, Summerland Key, FL 33042
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  $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

  Diane Corliss Coldwell Banker Schmitt RE Co.

  1113 de Lussan Ln, Summerland Key, FL 33042
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  $2,299,999 New Construction

  • 3 Beds
  • 3 Baths
  • 2,288 Sq Ft

  17210 Angelfish Ln, Summerland Key, FL 33042

  Experience the best of waterfront living in this brand-new home on Lower Sugarloaf Key. Thoughtfully designed and meticulously built, this 3-bedroom, 2.5-bath residence offers 2,288 square feet of modern coastal comfort. Situated on an expansive 16,445-square-foot lot, the property features a private seawall for direct boating access and a sparkling pool perfect for relaxing after a day on the

  The Spottswood Team Truman & Co. (KW)

  17210 Angelfish Ln, Summerland Key, FL 33042
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  $1,490,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,136 Sq Ft

  142 Peg Leg Ln, Cudjoe Key, FL 33042

  Welcome to your dream coastal retreat! This newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies, ideal for soaking in the sunrise or entertaining guests in true Keys style. Canal with direct access to the open ocean. No

  Jose Cabrera AmeriFirst Realty

  142 Peg Leg Ln, Cudjoe 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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  $599,000 New Construction

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042

  Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

  Ian Calderwood Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
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  $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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  $1,599,000

  • 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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  $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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  $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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  $1,075,000

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft

  165 Cutlass Ln, Summerland Key, FL 33042

  Discover your dream waterfront retreat in the Florida Keys. This canal-front home features 4 spacious bedrooms and 3 bathrooms with 2,448 sq. ft. of thoughtfully designed living space, perfect for accommodating family, guests, and entertaining. Enjoy expansive covered balconies on both levels, where you can relax and take in peaceful canal views and the laid-back island lifestyle. The generous

  Justyn Ewald Expert Realty LLC (HQ)

  165 Cutlass Ln, Summerland Key, FL 33042
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  $375,000

  • 2 Beds
  • 1 Bath
  • 726 Sq Ft

  701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042

  Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom turnkey home is move-in ready — whether you're looking for a full-time residence, vacation getaway, or income-producing rental. Step inside to a fresh, inviting living space designed for relaxed island living. The bright white

  Monika Rydzak EXP Realty LLC

  701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
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  $650,000

  • 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 is a leafy oasis or reconfigured for parking.

  Elizabeth Jolin Coldwell Banker Schmitt RE Co

  4 Shore Dr, Key West, FL 33040
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  $285,000

  • Land
  • 1.01 Acres
  • $282,178 per Acre

  Unlisted Address

  Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

  Coby Taylor Expert Realty LLC (HQ)

  Unlisted Address
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  /11

  $480,000

  • Land
  • 1,920 Sq Ft
  • $10,890,000 per Acre

  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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  $1,595,000

  • 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 Berkshire Hathaway HomeServices Knight & Gardner Realty

  16640 Cypress Rd, Summerland Key, FL 33042
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  $499,000

  • Land
  • 6,969 Sq Ft
  • $3,118,750 per Acre

  22552 Jolly Roger Dr, Cudjoe Key, FL 33042

  Oceanfront lot in the Lower Keys overlooking Cudjoe Bay. Build your dream with expansive open-water views and ocean breezes. Prime waterfront setting with incredible potential. No current building permit; buyer to verify process and timelines. Rare opportunity to own a slice of paradise.

  Lauren Dunn Coldwell Banker Schmitt Islamorada

  22552 Jolly Roger Dr, Cudjoe Key, FL 33042
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  /40

  $300,000

  • Land
  • 2,178 Sq Ft
  • $6,000,000 per Acre

  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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  $190,000

  • Land
  • 1.02 Acres
  • $186,275 per Acre

  Lot 15 bk2 Bad George Rd, Sugarloaf Key, FL 33042

  Build your dream home. Imagine waking up to the natural beauty of the Florida Keys on this 44,431sqft lot. Great location near Sugarloaf school. Easy commute to Key West, only 25 minutes. Nearby boat ramps.

  Elizabeth Greco-DeGrenier Coldwell Banker Schmitt RE Co.

  Lot 15 bk2 Bad George Rd, Sugarloaf Key, FL 33042

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