Sugarloaf Key, FL Homes

• 

  

  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,110 Sq Ft

  42 Beach Dr, Key West, FL 33040

  42 Beach Dr, Key West, FL 33040
• 

  

  

  /5

  $139,000

  • Land

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

  Tier 3 Lot.Discover the potential of this expansive 15,000 sq ft dry lot in Sugarloaf Key, just 20 minutes from Key West, FL. Ideal for creating your dream island retreat, this property offers ample space.

  Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
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  /46

  $951,000 Sold Sep 10, 2025

  76 Palm Dr, Key West, FL 33040

  • 3 Beds
  • 3 Baths
  • 1,598 Sq Ft
  • Built 2016

  Last Sold Summary

  • 27% Below List Price
  • $595/SF
  • 194 Days On Market

  Current Estimated Value $983,035

  Last Listing Agent Margarita Villoch Island Group Realty (KW)

  76 Palm Dr, Key West, FL 33040
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  /42

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 846 Sq Ft

  18 Shore Dr, Key West, FL 33040

  18 Shore Dr, Key West, FL 33040
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  /33

  $1,195,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  17226 Jamaica Ln, Summerland Key, FL 33042

  Completely remodeled, turn key 3 bed 2 bath canal front home that.backs up to the nature's preserve. Home features large pool with a bar area and 300 square feet enclosed storage ,mature landscaping and concrete wall with automatic gate . Easy boating access from new concrete dock to Atlantic ocean side and the Gulf. Actively profitable Airbnb home

  Stephen Hachey

  17226 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /45

  $799,000 Sold Aug 29, 2025

  17338 Dolphin St E, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,875 Sq Ft
  • Built 1963

  Last Sold Summary

  • 30% Below List Price
  • $426/SF
  • 171 Days On Market

  Current Estimated Value $902,238

  Last Listing Agent Alexa Morgan Buy The Keys

  17338 Dolphin St E, Summerland Key, FL 33042
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  /37

  Est $1,729,718 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  1008 Buttonwood Dr E, Summerland Key, FL 33042
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  /9

  $3,500,000

  • Land

  19657 Seminole St, Sugarloaf Key, FL 33042

  Unique Waterfront Property with Opportunity to Build Your Dream MansionWelcome to your once-in-a-lifetime opportunity to own a truly exceptional waterfront property in the Florida Keys. This expansive property boasts a total of 3 lots ensuring unparalleled potential for building your waterfront mansion.Property comes with build back letter. There's not another property like this south of

  Derek Epperly Engel & Volkers Key West

  19657 Seminole St, Sugarloaf Key, FL 33042
• 

  

  /22

  $820,000 Sold Feb 28, 2025

  93 Palm Dr, Key West, FL 33040

  • 3 Beds
  • 3 Baths
  • 1,307 Sq Ft
  • Built 2016

  Last Sold Summary

  • 7% Below List Price
  • $627/SF
  • 60 Days On Market

  Current Estimated Value $841,781

  Last Listing Agent Cliff Glansen FlatFee.com

  93 Palm Dr, Key West, FL 33040
• 

  

  /46

  Est $2,802,074 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,371 Sq Ft

  661 Sugarloaf Blvd, Summerland Key, FL 33042

  661 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /53

  $1,710,000

  • 4 Beds
  • 2 Baths
  • 2,605 Sq Ft

  1481 Sugarloaf Blvd, Summerland Key, FL 33042

  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

  Jenna Stauffer Ocean Sotheby's International Realty

  1481 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /35

  $945,000 Sold May 15, 2025

  17182 Starfish Ln W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Built 1991

  Last Sold Summary

  • 3% Below List Price
  • $747/SF
  • 6 Days On Market

  Current Estimated Value $962,221

  Last Listing Agent Daniel Urban Expert Realty LLC (HQ)

  17182 Starfish Ln W, Summerland Key, FL 33042
• 

  /2

  Est $1,600,155 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042
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  /82

  $3,699,000

  • 3 Beds
  • 3.5 Baths
  • 1,744 Sq Ft

  17183 Coral Dr, Summerland Key, FL 33042

  Nestled within this 280 ft of concrete walled and gated property lies a tropical oasis that epitomizes Keys living. Situated on a huge,12,000 sq ft corner lot that provides an exclusive island vibe with lots of privacy that comes complete with 200' of canal frontage, a 133' concrete dock, a new 10k lb boat lift, fish cleaning station, and travertine steps into the sparkling water for an enjoyable

  Jan Fritz Coldwell Banker Schmitt RE Co.

  17183 Coral Dr, Summerland Key, FL 33042
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  /42

  $1,450,000 Sold Jun 23, 2025

  17177 Bonita Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft
  • Built 1978

  Last Sold Summary

  • 19% Below List Price
  • $1,018/SF
  • 362 Days On Market

  Current Estimated Value $1,479,558

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  17177 Bonita Ln W, Summerland Key, FL 33042
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  /24

  Est $967,374 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,482 Sq Ft

  19453 Seminole St, Sugarloaf Key, FL 33042

  19453 Seminole St, Sugarloaf Key, FL 33042
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  /15

  $644,500

  • Land

  132 Sugarloaf Dr, Summerland Key, FL 33042

  Looking for your ROGO exempt slice of paradise. Look no further, build your dream home now. Large lush private lot. access from two streets to drive through. ROGO Exempt letter in hand, no waiting!! Community Marina and Ramp across the road.Great boating access to both Gulf and Atlantic. This beautiful lot awaits you to build your dream home. There is plenty space for Pool, storage, garage,

  Heather Mason Coastal Collection Real Estate Inc.

  132 Sugarloaf Dr, Summerland Key, FL 33042
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  /42

  $630,000 Sold Jul 21, 2025

  92 Frazier Ln, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 768 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $820/SF
  • 43 Days On Market

  Current Estimated Value $600,261

  Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  92 Frazier Ln, Summerland Key, FL 33042
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  /49

  Est $6,932,053 Not Listed For Sale

  • 10 Beds
  • 11.5 Baths
  • 10,607 Sq Ft

  17279 Oleander Ln, Sugarloaf Key, FL 33042

  17279 Oleander Ln, Sugarloaf Key, FL 33042
• 

  

  /100

  $9,950,000

  • 6 Beds
  • 5 Baths
  • 5,208 Sq Ft

  16750 Old State Road 4a, Summerland Key, FL 33042

  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

  Lisa Swanson The Agency Florida Keys

  16750 Old State Road 4a, Summerland Key, FL 33042
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  /44

  $900,000 Sold Sep 15, 2025

  2950 Overseas Hwy Unit 57, Key West, FL 33040

  • Land

  Last Sold Summary

  • 10% Below List Price
  • 4 Days On Market

  Current Estimated Value $938,843

  Last Listing Agent Oleksandr Khiznichenko Keller Williams Key West Compass Realty

  2950 Overseas Hwy Unit 57, Key West, FL 33040
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  /40

  Est $912,672 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  93 Venetian Way, Summerland Key, FL 33042

  93 Venetian Way, Summerland Key, FL 33042
• 

  

  /41

  $825,000

  • Land

  2950 Overseas Hwy Unit 2, Key West, FL 33040

  Oceanside Elegance Awaits - Your Ultimate Waterfront RetreatDiscover an unparalleled waterfront escape with this brand-new Luxury Canal-front Platinum RV Lot 2, thoughtfully designed to accommodate RVs of all sizes. This premium lot boasts an expansive Tiki Hut, adorned with custom handcrafted wooden cabinets and modern Trex decking, creating an inviting outdoor sanctuary.Indulge in top-tier

  Oleksandr Khiznichenko Keller Williams Key West Compass Realty

  2950 Overseas Hwy Unit 2, Key West, FL 33040
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  /35

  $560,000 Sold Aug 29, 2025

  19616 Aztec St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,129 Sq Ft
  • Built 1953

  Last Sold Summary

  • 20% Below List Price
  • $496/SF
  • 196 Days On Market

  Current Estimated Value $584,724

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  19616 Aztec St, Summerland Key, FL 33042
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  /61

  Est $1,926,703 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft

  17153 Buttonwood Dr W, Summerland Key, FL 33042

  17153 Buttonwood Dr W, Summerland Key, FL 33042
• 

  

  /48

  $689,000

  • Land

  2950 Overseas Hwy Unit 24, Key West, FL 33040

  **Welcome to Lot 24 at Bluewater Luxury RV Resort - a premier destination for upscale RV living in the Florida Keys.**This deeded Tropical Luxury RV lot offers the perfect blend of comfort, convenience, and elegance in a lush tropical setting. Spacious and level, the lot easily accommodates an RV or motorhome and is surrounded by vibrant landscaping, swaying palms, and colorful flowers.Designed

  Oleksandr Khiznichenko Keller Williams Key West Compass Realty

  2950 Overseas Hwy Unit 24, Key West, FL 33040
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  /29

  $1,245,000 Sold Jul 28, 2025

  17081 Starfish Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,542 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $807/SF
  • 199 Days On Market

  Current Estimated Value $1,285,971

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

  17081 Starfish Ln W, Summerland Key, FL 33042
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  /39

  Est $1,710,187 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,426 Sq Ft

  17056 Wahoo Ln, Summerland Key, FL 33042

  17056 Wahoo Ln, Summerland Key, FL 33042
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  /16

  $4,375,000 New Construction

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

  231 E Shore Dr Unit 5, 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 5, Key West, FL 33040
• 

  

  /42

  $895,000 Sold May 21, 2025

  17214 La Brisa Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft
  • Built 1992

  Last Sold Summary

  • 10% Below List Price
  • $666/SF
  • 50 Days On Market

  Current Estimated Value $948,429

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  17214 La Brisa Ln, Summerland Key, FL 33042
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  /43

  Est $1,103,725 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft

  17055 Kingfish Ln W, Summerland Key, FL 33042

  17055 Kingfish Ln W, Summerland Key, FL 33042
• 

  

  /96

  $1,698,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,353 Sq Ft

  17176 Bonita Ln W, Summerland Key, FL 33042

  ***Open House Saturday, February 7th from 1-3Experience island living in this 2,353 sq ft, 4-bed, 3-bath Sugarloaf Shores home on a 12,500 sq ft lot. The split-level design includes two ensuite bedrooms with balcony access, plus two guest rooms on the ground floor. Skylights brighten the open living areas, flowing seamlessly to a 44' screened balcony.Out back, enjoy a 22' x 10' pool, gazebo,

  Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  17176 Bonita Ln W, Summerland Key, FL 33042
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  /40

  $785,000 Sold Mar 12, 2025

  17236 Keystone Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft
  • Built 1974

  Last Sold Summary

  • 21% Below List Price
  • $680/SF
  • 184 Days On Market

  Current Estimated Value $831,110

  Last Listing Agent Everett Watkins Keller Williams Key West Compass Realty

  17236 Keystone Rd, Summerland Key, FL 33042
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  /50

  Est $924,486 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft

  17396 Jamaica Ln, Summerland Key, FL 33042

  17396 Jamaica Ln, Summerland Key, FL 33042
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  /3

  $179,000 Pending

  • Land
  • 0.11 Acre
  • $1,627,273 per Acre

  Lot 32 Caloosa St, Sugarloaf, FL 33042

  Lot with ROGO letter for 5 points. Not ROGO exempt, use points towards building on another lot or contact the Monroe County Planning Department for information about building on this lot or how to use these points. Tier 3 AE11. Contact Monroe County to verify all information. ROGO letter available upon request.

  Pamela Stangler MMLS Assoc.-Inactive Member

  Lot 32 Caloosa St, Sugarloaf, FL 33042
• 

  

  /85

  $1,800,000 Sold Jan 23, 2026

  17054 Coral Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,422 Sq Ft
  • Built 2004

  Last Sold Summary

  • 10% Below List Price
  • $743/SF
  • 240 Days On Market

  Last Listing Agent Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  17054 Coral Dr, Summerland Key, FL 33042
• 

  

  /30

  Est $2,298,604 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,000 Sq Ft

  17082 Starfish Ln W, Summerland Key, FL 33042

  17082 Starfish Ln W, Summerland Key, FL 33042
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  /71

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft

  19881 Date Palm Dr, Summerland Key, FL 33042

  Escape to your own private paradise at 19881 Date Palm Drive in Sugarloaf Key! This beautifully updated single-family home is tucked away in a quiet, secluded location and offers 100 feet of pristine canal frontage with a cut-in boat slip--perfect for boating enthusiasts with no neighbors across the canal!Step inside to find rich Brazilian hardwood floors, custom wood cabinetry, and sleek

  Jimmy Lane Island Life Realty Experts

  19881 Date Palm Dr, Summerland Key, FL 33042
• 

  

  /29

  $980,000 Sold May 29, 2025

  1107 Hawksbill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1984

  Last Sold Summary

  • 11% Below List Price
  • $851/SF
  • 54 Days On Market

  Current Estimated Value $991,949

  Last Listing Agent Richard Haskins Buy The Keys

  1107 Hawksbill Ln, Summerland Key, FL 33042
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  /2

  Est $939,373 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,218 Sq Ft

  17174 Kingfish Ln W, Summerland Key, FL 33042

  17174 Kingfish Ln W, Summerland Key, FL 33042

Showing Results 81 - 120, Page 3 of 18