Summerland Key, FL Homes for Sale

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  /31

  $740,000

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  4099 Egret Ln, Summerland Key, FL 33042

  Excellent Investment Opportunity! Classic waterfront home in quiet Big Torch Key. This home features 2 bedrooms, two bathrooms and a spacious open living/dining/kitchen area. Water from a 12k gallon cistern with a reverse osmosis system. City water is available and the home is connected to sewer. This home is being sold as a life estate. The homeowner will remain in place after purchase of the

  Banks Prevatt Coldwell Banker Schmitt RE Co.

  4099 Egret Ln, Summerland Key, FL 33042
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  /43

  $1,145,000

  • 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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  /29

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  463 Lesrohde Dr, Ramrod Key, FL 33042

  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

  Sarah Dolson Keller Williams Key West Compass Realty

  463 Lesrohde Dr, Ramrod 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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  /7

  $3,995,900 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft

  231 E Shore Dr Unit 1, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 1, Summerland 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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  /30

  $519,000

  • 2 Beds
  • 1 Bath
  • 1,253 Sq Ft

  31541 Avenue A, Big Pine Key, FL 33043

  Welcome to this Key West-style home located on Big Pine Key! Situated on a generous 7500 square-foot fully fenced lot, this property offers ample space for parking and storage, making it a perfect island retreat for those looking to escape the hustle and bustle. As you step inside, you'll be greeted by the cozy charm of two bedrooms and a well-appointed bathroom, providing a comfortable living

  Melissa Graham Bluescape Real Estate

  31541 Avenue A, Big Pine Key, FL 33043
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  /60

  $175,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,120 Sq Ft

  27433 Antigua Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION CO-OWNERSHIP POOL HOME! 1/10 Shares. 8 Shares are still available for sale for this brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and

  Kelly Gardner Bluescape Real Estate

  27433 Antigua Rd, Summerland Key, FL 33042
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  /41

  $840,000

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft

  3635 Tradewinds St, Big Pine Key, FL 33043

  Beautifully Renovated Single-Family Home in the Florida Keys This stunning 2-bedroom, 2-bathroom home with extra guess room downstairs, fully renovated in 2024, is perfect for fishing enthusiasts and those seeking a serene island lifestyle. The property boasts a 50-foot dock with no bridges to the ocean, ideal for quick access to the water. Located in a quiet neighborhood, this home features a

  Michel Luna Lifestyle International Realty

  3635 Tradewinds St, Big Pine Key, FL 33043
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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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  /44

  $1,174,000

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  27426 Martinique Ln, Summerland Key, FL 33042

  Oceanside canal-front opportunity in Ramrod Key. This 3-bedroom, 2-bath home with a pool is ideally located near Looe Key Reef and Picnic Island, and is just a 10-minute walk to the local watering hole, The Tiki.The property includes an additional buildable lot, creating a rare opportunity to construct a second residence, guest house, or future income-producing property--significantly enhancing

  Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  27426 Martinique Ln, Summerland Key, FL 33042
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  /41

  $799,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  1634 Lantana Ln, Big Pine Key, FL 33043

  Custom-built 2-bedroom, 2-bathroom home (1987) situated on a boating canal in the sought-after Eden Pines neighborhood of Big Pine Key where the Key Deer roam. Short stilted home located on a 6,000 sq. ft. lot the property offers 60 feet of concrete seawall ideal for your boat of choice, with excellent boating access via Pine Channel. Boaters should note two bridges en route with approximate

  Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  1634 Lantana Ln, Big Pine Key, FL 33043
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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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  /18

  $849,000

  • 3 Beds
  • 1 Bath
  • 1,043 Sq Ft

  550 Pine Ln, Big Pine Key, FL 33043

  This newly remodeled 3-bedroom, 1-bathroom home is perfectly positioned on a spacious lot in the heart of Big Pine Key, offering 10,275 sq ft of land and an incredible 75 feet of waterfrontage, with a concrete seawall. With quick access to the ocean via Spanish Harbor Channel, this is a boater's dream come true.Inside, enjoy peace of mind with impact-rated windows and doors, a sturdy metal roof,

  Justyn Ewald Expert Realty LLC (HQ)

  550 Pine Ln, Big Pine Key, FL 33043
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  /31

  $849,000

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  31226 Hollerich Dr, Big Pine Key, FL 33043

  Buy a slice of the Florida Keys with this sturdy CBS 2-2 located in one of the most convenient locations available! Boating is a short ride to Bogie channel which offers easy access to both the Gulf of Mexico and the Atlantic! World-class fishing at your fingertips! Also nearby is Big Pine Park, and many amenities like the Winn-Dixie shopping center. More about the house; the first floor

  Wyatt Tucker Action Keys Realty of the Lower FL Keys LLC

  31226 Hollerich Dr, Big Pine Key, FL 33043
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  /101

  $2,499,999

  • 3 Beds
  • 3 Baths
  • 3,013 Sq Ft

  680 Cruikshank Island, Summerland Key, FL 33042

  Welcome to 680 Cruikshank Isle, an extraordinary waterfront estate in the heart of Summerland Key that captures the essence of Florida Keys luxury living. Offering over 3,000 sq. ft. of interior space, this three-bedroom, three-bath residence is thoughtfully designed for both elegance and comfort, blending open living areas with timeless architectural details.Inside, soaring ceilings and

  Barbara Crespo Keller Williams Key West Compass Realty

  680 Cruikshank Island, Summerland Key, FL 33042
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  /43

  $1,750,000

  • 3 Beds
  • 3 Baths
  • 1,837 Sq Ft

  30363 Flamingo Ln, Big Pine Key, FL 33043

  Tranquility meets coastal living, discover this stunning concrete constructed home built in 1993. Located in the desirable subdivision of Tropical Bay Estates this elevated waterfront residence offers unparalleled access to both the ocean and bay, just 15 minutes by boat. The iconic No Name Pub is just a 2-minute drive or a 15-minute walk away for some of the best pizza in the Keys. A few

  Jo Ann Cook Ocean Sotheby's International Realty

  30363 Flamingo Ln, Big Pine Key, FL 33043
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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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  /62

  $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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  /27

  $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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  /15

  $250,000

  • Land

  27057 Angelfish Rd, Ramrod Key, FL 33042

  6000 square foot lot with a building permit IN-PROCESS for a 3 bedroom / 2 bath stilted single family residence. 1320 square feet. The plans are for an Affinity home with features that include impact doors and windows and built to 180 mph with a cistern and designed using the Green Building code. Great for the environment, great for your insurance rates.Located a bike ride away from Boondocks

  Donna Pezzi Keller Williams Key West Compass Realty

  27057 Angelfish Rd, Ramrod Key, FL 33042
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  /7

  $4,375,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft

  231 E Shore Dr Unit 3, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept layouts with 10'

  Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 3, Summerland Key, FL 33042
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  /16

  $325,000

  • Land

  27935 Tarpon Terrace, Summerland Key, FL 33042

  Heather Mason Coastal Collection Real Estate Inc.

  27935 Tarpon Terrace, Summerland Key, FL 33042
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  /17

  $450,000

  • Land

  132 Blackbeard Rd, Little Torch Key, FL 33042

  This beautiful oversized lot is located in Jolly Rogers Estates, Little Torch Key. Corner lot with two sides of canal front with some open water views. PERMIT HAS BEEN ALLOCATED, get ready to build. Permit is for a 1227 sq ft 3 bedrooms & 2 baths, Modular Home. Seawall permit is with the county. Enjoy quick boating access to the Gulf and Atlantic. Dolphin Marina is across the canal from this

  Halley Haack Coldwell Banker Schmitt RE Co.

  132 Blackbeard Rd, Little Torch 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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  /19

  $1,750,000 New Construction

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft

  29558 Ranger Ave, Big Pine Key, FL 33043

  Experience the Ultimate Keys Lifestyle - New Construction with 75' of Waterfront on a Wide Boating CanalComing Fall 2025 - Nestled on a spacious 7,500 sqft lot (75x100) along a deep, wide boating canal, this brand new 1,500 sqft home offers the perfect blend of modern coastal living and exceptional boating access. With quick entry to Pine Channel, you're just minutes from both the Atlantic Ocean

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  29558 Ranger Ave, Big Pine Key, FL 33043
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  /26

  $229,000

  • 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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  /22

  $695,000

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  3943 Venna Rd, Big Pine Key, FL 33043

  Welcome to your island retreat in the sought-after community of Port Pine Heights on Big Pine Key. This charming stilted waterfront home offers quick boating access to Pine Channel, perfect for those who love life on the water. Families are drawn to this serene neighborhood for its privacy, friendly Key Deer, and close proximity to No Name Key, as well as the sparkling beaches and crystal-clear

  Thomas Carden Keys to the Coast Real Estate LLC

  3943 Venna Rd, Big Pine Key, FL 33043
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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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  /43

  $4,500,000

  • 2 Beds
  • 2 Baths
  • 1,467 Sq Ft

  4670 Dorn Rd, Summerland Key, FL 33042

  Discover a rare offering in the Florida Keys--an exceptional 2.84-acre waterfront estate on Big Torch Key, where serenity, seclusion, and world-class boating converge. Gracefully positioned on a coveted point lot, this remarkable property delivers sweeping open-water views, a private beach with boat launch, and protected dockage, offering an unparalleled coastal lifestyle.From sunrise to sunset,

  Sharon Davison Keller Williams Key West Compass Realty

  4670 Dorn Rd, Summerland Key, FL 33042
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  /4

  $245,000

  • Land

  30921 Bailey Rd, Big Pine Key, FL 33043

  Ready..Set.. Build!! Welcome to the future home site in the sought-after neighborhood of Big Pine Key! There are two ROGO-exempt vacant lots available for $245,000 each that offer a rare opportunity to build your dream home in paradise. No waiting for permit allocation!!

  Maryann Warren Coldwell Banker - Ft. Lauderdale

  30921 Bailey Rd, Big Pine Key, FL 33043
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  /7

  $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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