Sugarloaf, FL Homes for Sale

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  /59

  $535,000

  $14K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042

  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

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
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  /3

  $275,000

  • Land
  • 0 Sq Ft

  0 Disturbed Pine Rd Unit 620297, Cudjoe Key, FL 33042

  Take a look at this 24 point lot that has a letter from Monroe County to be used toward building in the ROGO system. Contact Monroe County Building Department and/or the Monroe County Planning Department to verify use of this point lot. A great deal for anyone needing points to be competitive in the ROGO system.

  Pamela Stangler Expert Realty LLC

  0 Disturbed Pine Rd Unit 620297, Cudjoe Key, FL 33042
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  /70

  $950,000

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft

  123 Venetian Way, Summerland Key, FL 33042

  On a quiet dead-end street in the highly sought-after Sugarloaf Shores community, sits this fully renovated tropical retreat thats reminiscent of something straight out of a secret garden. Set on an oversized, gated and partially fenced parcel spanning over a quarter acre, this rare non-waterfront property offers the kind of lush green space that's nearly impossible to find in the Florida Keys.

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  123 Venetian Way, Summerland Key, FL 33042
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  /45

  $1,150,000

  $100K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  20868 5th Ave W, Summerland Key, FL 33042

  Welcome to your cozy coastal retreat in Cudjoe Gardens in the beautiful Florida Keys! This well maintained 2bedroom, 2bath CBS home offers 1,344 sq ft of comfortable island living with thoughtful upgrades throughout. Step inside to find custom cabinetry, adding both style and functionality to the home's inviting interior. Outside is where this property truly shines, featuring a private, small man

  Karen Haack Coldwell Banker Schmitt RE Co.

  20868 5th Ave W, Summerland Key, FL 33042
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  /13

  $85,000

  • Land
  • 4 Acres
  • $21,250 per Acre

  LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042

  Offshore island 4 acre lot in the heart of the Great White Heron Wildlife refuge is suitable for temporary camping and exploration. World class flats fishing for bonefish, tarpon, permit and redfish nearby. Located on Southwest end of Little Knockemdown Key. Accessible by kayak, paddle board and shallow draft vessels. Privacy and nature abound here on Little Knockemdown Key - No roads or

  Banks Prevatt Coldwell Banker Schmitt RE Co.

  LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042
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  /55

  $329,000

  $98K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 748 Sq Ft

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042

  Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental as

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
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  /32

  $339,000

  $210K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

  Great opportunity to own an income-producing home in the gated community of Venture Out on Cudjoe Key. This 2-bedroom, 1-bath mobile home features a cozy layout with a true Florida Keys feel throughout. The property is ideally situated on a private lot with no neighbors on one side or behind, offering added privacy and tranquility. Whether you're looking for a full-time residence or a turnkey

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
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  /42

  $1,299,000

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,741 Sq Ft

  21025 3rd Ave, Summerland Key, FL 33042

  Experience the best of ocean-side living with no bridges to open water--a true boater's dream! This spacious 3-bedroom, 2-bath home offers 1,741 square feet of comfortable living designed for both relaxation and entertaining.A charming paver walkway welcomes you to elegant double-door entry, opening into a bright and expansive living area with soaring high ceilings. The open layout flows

  Diane Corliss Coldwell Banker Schmitt RE Co.

  21025 3rd Ave, Summerland Key, FL 33042
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  /16

  $895,900

  $94K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22961 John Avery Ln, Summerland Key, FL 33042

  Reduced over 100k for a quick sale! Boater's Paradise in Cudjoe Key under 1 million!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

  Rayden Vega Casa Miami Real Estate

  22961 John Avery Ln, Summerland Key, FL 33042
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  /16

  $2,195,000

  Pre-Foreclosure

  • 5 Beds
  • 3 Baths
  • 1,903 Sq Ft

  125 Colson Dr, Summerland Key, FL 33042

  TRANSIENT LICENSE * NIGHTLY RENTALS* PROVEN RENTAL INCOME* IDEAL 1031 EXCHANGE OPPORTUNITY Casa De Las Palmas Rarely does a Florida Keys property combine proven income, privacy, and future potential like this. Situated on nearly two acres spanning four lots, this unique compound offers a coveted transient license allowing nightly rentals and a well-established vacation rental business with a

  Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

  125 Colson Dr, Summerland Key, FL 33042
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  /3

  $120,000

  $15K PRICE DROP

  • Land
  • 15,000 Sq Ft
  • $348,480 per Acre

  19617 Date Palm Dr, Sugarloaf Key, FL 33042

  Now only $120,000. 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

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

  19617 Date Palm Dr, Sugarloaf Key, FL 33042
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  /21

  $750,000

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  19421 Canal Dr, Summerland Key, FL 33042

  Great opportunity to have your home in a charming neighborhood on Sugarloaf key, MM 19.5. Enjoy your 3-bedroom 2-bath single family home on a large 15000 sq ft lot with screened front porch and open patio in the backyard. This large yard has plenty of room for a pool, Boats, RV, Trailers and your toys! Home is located down the street from Sugarloaf School, 20 miles to Key West and 27 miles to

  Rosa Cappiello Century 21 Circle- Islamorada

  19421 Canal Dr, Summerland Key, FL 33042
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  /14

  $255,000

  $255K PRICE INCREASE

  • Land
  • 2,178 Sq Ft
  • $5,100,000 per Acre

  701 Spanish Main Dr Unit LOT 399, Cudjoe Key, FL 33042

  Welcome to island living at its best in the gated waterfront community of Venture Out on Cudjoe Key. Lot 399 is a desirable 35' x 69' corner RV lot offering ocean peeks, full hookups, and endless possibilities. Whether you're looking for a personal Florida Keys retreat, an income-producing investment, or the perfect spot to build your future island home, this ROGO-exempt property checks all the

  Monika Rydzak eXp Realty LLC KW Branch

  701 Spanish Main Dr Unit LOT 399, Cudjoe Key, FL 33042
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  /53

  $449,999

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft

  701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

  Ocean-View Waterfront Retreat in Gated Venture Out on Cudjoe Key.NIGHTLY RENTALS ALLOWEDEnjoy the Florida Keys lifestyle in this well-maintained 1-bedroom, 1-bathroom waterfront home located in the highly desirable gated community of Venture Out. With ocean views, direct boating access, excellent amenities, and nightly rentals permitted, this property is ideal as a vacation home,

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
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  /5

  $249,000

  $26K PRICE DROP

  • Land
  • 6,969 Sq Ft
  • $1,556,250 per Acre

  1155 Thatch Ln, Cudjoe Key, FL 33042

  Build your Florida Keys dream in Cudjoe Key just 3 lots from open water. Dock has already been approved and house plans are ready to submit to the county to begin the ROGO process.

  Tommy Mack Coastal Collection Real Estate Inc.

  1155 Thatch Ln, Cudjoe Key, FL 33042
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  /25

  $4,375,000

  New Construction $125K PRICE INCREASE

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

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

  Welcome home to an exceptional new-construction residence in a private, gated community offering resort-style amenities, a boat slip and nightly rental opportunities. Conveniently located next to Summerland Key Airport, this fully upgraded home features a private elevator, a stunning infinity pool overlooking the water and an expansive rooftop deck perfect for enjoying breathtaking Florida Keys

  Stephanie Marinucci Serhant

  231 E Shore Dr Unit 6, Key West, FL 33040
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  /36

  $5,995,000

  $295K PRICE DROP

  • 13 Beds
  • 7 Baths
  • 5,022 Sq Ft

  21470 Overseas Hwy, Cudjoe Key, FL 33042

  Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest

  Jennifer Weeks Select Properties of NWFL

  21470 Overseas Hwy, Cudjoe Key, FL 33042
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  /43

  $899,000

  $400K PRICE DROP

  • 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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  /52

  $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 ComfortWelcome to your island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located within the gated waterfront community of Venture Out on Cudjoe Key.Inside, you'll find a bright, open-concept layout featuring a spacious living area that flows seamlessly into a thoughtfully designed

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
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  /6

  $225,000

  $25K PRICE DROP

  • Land
  • 6,098 Sq Ft
  • $1,607,143 per Acre

  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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  /8

  $365,000

  • Land
  • 2,178 Sq Ft
  • $7,300,000 per Acre

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

  Discover your own piece of paradise in Venture Out! This beautifully maintained waterfront lot offers 17 feet of seawall and a private tropical setting enhanced by mature landscaping and thoughtful care. Whether you're looking for the perfect RV getaway, seasonal retreat, or future homesite, this property provides the ideal blend of privacy, beauty, and waterfront living.Located within the

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042
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  /27

  $350,000

  $25K PRICE DROP

  • 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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  /11

  $460,000

  $20K PRICE DROP

  • Land
  • 1,742 Sq Ft
  • $11,500,000 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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  /77

  $12,999,999

  $1M PRICE DROP

  • 31 Beds
  • 19 Baths

  21470 Overseas Hwy, Cudjoe Key, FL 33042

  Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean.

  Jennifer Weeks Select Properties of NWFL

  21470 Overseas Hwy, Cudjoe Key, FL 33042
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  /6

  $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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  /52

  $4,250,000

  New Construction $36M PRICE DROP

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

  231 E Shore Dr Unit 2, Key West, FL 33040

  Welcome home to an exceptional new-construction residence in a private, gated community offering resort-style amenities, a boat slip and nightly rental opportunities. Conveniently located next to Summerland Key Airport, this fully upgraded home features a private elevator, a stunning infinity pool overlooking the water and an expansive rooftop deck perfect for enjoying breathtaking Florida Keys

  Hope Firestone Serhant

  231 E Shore Dr Unit 2, Key West, FL 33040
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  /4

  $985,000

  • Land
  • 6,098 Sq Ft
  • $7,035,714 per Acre

  Unlisted Address

  ROGO EXEMPT CANALFRONT WITH GREAT SUNSETS AND OPEN WATER VIEWS READY FOR YOU TO BRING YOUR BOAT WITH STEP DOWN DOCK. DOCK NEEDS SOME TLC. ACTIVE WATER METER ON SITE, SEWER STUBBED IN AND READY FOR CONNECTION AS A PRIOR HOME WAS DEMOLISHED. BUYER TO VERIFY ALL INFORMATION. POWER IN FRONT. SURVEY AVIALABLE. TWO STORY HOME WOULD PROVIDE SPECTACULAR VIEWS AND A TREMENDOUS OPPORTUNITY FOR YOUR VISION,

  Unlisted Address

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