Sugarloaf Key, FL Homes

• 

  

  

  /48

  $649,000

  $50K PRICE DROP

  • Land
  • 2,613 Sq Ft
  • $10,816,667 per Acre

  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

  Oleksandr Khiznichenko Keller Williams Key West Compass Realty

  2950 Overseas Hwy Unit 24, Key West, FL 33040
• 

  

  

  /3

  $1,150,000

  Sold Jul 29, 2026

  56 Bay Dr, Saddlebunch, FL

  • 3 Beds
  • 2 Baths
  • 1,372 Sq Ft
  • Built 1978

  Last Sold Summary

  • 11% Below List Price
  • $838/SF
  • 235 Days On Market

  Current Estimated Value $1,294,938

  Last Listing Agent Stephanie Wise Keller Williams Key West Compass Realty

  56 Bay Dr, Saddlebunch, FL
• 

  

  

  /50

  Est $971,213

  Not Listed For Sale

  17396 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft
  • Built 1992

  17396 Jamaica Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)
• 

  

  

  /42

  $829,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 984 Sq Ft

  937 Loggerhead Ln, Summerland Key, FL 33042

  Opportunities like this are hard to find in the Lower Keys--this fully renovated 3-bedroom, 2-bath home sits on a generous half-acre lot in the highly desirable Sugarloaf Key area, offering space, privacy, and modern upgrades throughout. Designed for easy coastal living, the home features durable Hardie board siding, a long-lasting metal roof, tile flooring throughout, and an energy-efficient

  Richard Haskins Buy The Keys

  937 Loggerhead Ln, Summerland Key, FL 33042
• 

  

  

  /29

  $825,000

  Sold Feb 27, 2026

  17245 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2000

  Last Sold Summary

  • 11% Below List Price
  • $661/SF
  • 104 Days On Market

  Current Estimated Value $873,424

  Last Listing Agent Team Kaufelt Truman & Co. (KW)

  17245 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /30

  Est $2,394,316

  Not Listed For Sale

  17082 Starfish Ln W, Summerland Key, FL 33042

  • 6 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • Built 1988

  17082 Starfish Ln W, Summerland Key, FL 33042

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Andrea Goodwin KeyIsle Realty - Florida Keys
• 

  

  /3

  $179,000

  $20K PRICE DROP Pending

  • Land
  • 4,791 Sq Ft
  • $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
• 

  

  /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 $983,288

  Last Listing Agent Margarita Villoch Island Group Realty (KW)

  76 Palm Dr, Key West, FL 33040
• 

  /2

  Est $987,814

  Not Listed For Sale

  17174 Kingfish Ln W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,218 Sq Ft
  • Built 1975

  17174 Kingfish Ln W, Summerland Key, FL 33042
• 

  

  /49

  $890,000

  $20K PRICE DROP

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

  813 Hawksbill Ln, Summerland Key, FL 33042

  Charming 2BR/2BA PLUS A LOFT, Keys home on Upper Sugarloaf, the perfect blend of comfort and waterfront living. Built on sturdy concrete pilings with Hardie board siding and a metal roof, this three-story retreat of island living. with GENERAC Generator. Inside, you'll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys lifestyle. What truly

  Miguel Solis Berkshire Hathaway HomeServices EWM Realty - Coral Gables

  813 Hawksbill Ln, Summerland Key, FL 33042
• 

  

  /47

  $1,375,000

  Sold May 20, 2026

  16823 E Point Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 1,740 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • $790/SF
  • 46 Days On Market

  Current Estimated Value $1,388,000

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  16823 E Point Dr, Summerland Key, FL 33042
• 

  

  /15

  Est $720,110

  Not Listed For Sale

  16991 Shore Dr, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1958

  16991 Shore Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Daniel Urban Expert Realty LLC (HQ)
• 

  

  /58

  $1,299,000

  $100K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft

  885 Hawksbill Ln, Summerland Key, FL 33042

  Recently updated canal-front home in highly desirable Upper Sugarloaf Key with direct boating access to the world famous Florida Keys back-country and Gulf of America. Located at 885 Hawksbill Lane, this waterfront property sits on a 6,120 sq ft lot and features a concrete seawall with boat davits, pavers and a heated swimming pool and spa completed in 2022. Enjoy canal and mangrove views plus

  Tommy Mack Coastal Collection Real Estate Inc.

  885 Hawksbill Ln, Summerland Key, FL 33042
• 

  

  /6

  $1,400,000

  Sold May 28, 2026

  17195 Hibiscus Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1987

  Last Sold Summary

  • $1,080/SF
  • 0 Days On Market

  Current Estimated Value $1,392,754

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17195 Hibiscus Ln W, Summerland Key, FL 33042
• 

  

  /21

  Est $818,731

  Not Listed For Sale

  19570 Mayan St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1958

  19570 Mayan St, Summerland Key, FL 33042

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Thomas Mack SBX Real Estate, LLC (KW)
• 

  

  /39

  $450,000

  • 2 Beds
  • 2 Baths
  • 873 Sq Ft

  4 Coral Dr, Key West, FL 33040

  Affordable Living in the Florida Keys Has Arrived! Welcome to this charming 2-bedroom, 2-bathroom home offering comfortable living space, an open-concept layout, and inviting outdoor areas perfect for dining, entertaining, or simply enjoying our beautiful Florida Keys lifestyle. Step inside to a bright and open living room and kitchen just off the front entry. Both bedrooms are privately situated

  Bobby Coe RE/MAX Keys Connection (KW)

  4 Coral Dr, Key West, FL 33040
• 

  

  /94

  $3,150,000

  Sold Jul 21, 2026

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042

  • 5 Beds
  • 4 Baths
  • 3,060 Sq Ft
  • Built 1970

  Last Sold Summary

  • 10% Below List Price
  • $1,029/SF
  • 130 Days On Market

  Current Estimated Value $3,123,049

  Last Listing Agent Daniel Urban Expert Realty LLC (HQ)

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042
• 

  

  /73

  Est $1,119,110

  Not Listed For Sale

  103 Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft
  • Built 1989

  103 Shore Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Stephany Duvall Engel & Völkers Marathon
• 

  

  /49

  $755,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  19543 Navajo St, Cudjoe Key, FL 33042

  3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size

  Pamela Stangler Expert Realty LLC

  19543 Navajo St, Cudjoe Key, FL 33042
• 

  

  /22

  $649,000

  Sold May 20, 2026

  19591 Navajo St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1994

  Last Sold Summary

  • 4% Below List Price
  • $624/SF
  • 25 Days On Market

  Current Estimated Value $657,807

  Last Listing Agent Mike Kane Internet Realty of the Florida Keys

  19591 Navajo St, Summerland Key, FL 33042
• 

  

  /29

  Est $1,364,178

  Not Listed For Sale

  17081 Starfish Ln W, Summerland Key, FL 33042

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

  17081 Starfish Ln W, Summerland Key, FL 33042

  Last Sold Summary

  • 175 Days On Market

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt RE Co
• 

  

  /53

  $2,375,000

  • 5 Beds
  • 4 Baths
  • 2,772 Sq Ft

  205 S Point Dr, Summerland Key, FL 33042

  Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bedroom, four-bathroom residence is thoughtfully designed to host family and guests with ease, featuring a desirable split-floor plan and expansive living spaces framed by endless turquoise views. The primary suite is a private

  Dawn McComish Lokation Real Estate

  205 S Point Dr, Summerland Key, FL 33042
• 

  

  /3

  $1,150,000

  Sold Mar 02, 2026

  2950 Overseas Hwy Unit 38, Key West, FL 33040

  • Land
  • 4,780 Sq Ft
  • $10,479,916 per Acre

  Last Sold Summary

  • 30% Below List Price
  • 227 Days On Market

  Last Listing Agent Oleksandr Khiznichenko Keller Williams Key West Compass Realty

  2950 Overseas Hwy Unit 38, Key West, FL 33040
• 

  

  /27

  Est $2,122,867

  Not Listed For Sale

  17022 Starfish Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,990 Sq Ft
  • Built 1994

  17022 Starfish Ln W, Summerland Key, FL 33042

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Kieran Mahoney Sugarloaf Realty LLC
• 

  

  /31

  $998,000

  $57K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,225 Sq Ft

  83 Sugarloaf Dr, Summerland Key, FL 33042

  Botanical Waterfront Compound ~ 3 bedroom/2 bath elevated CBS home on a fenced half-acre, just 20 minutes from Key West and near Sugarloaf schools. Potential for a fourth (4) bedroom, office, hobby room, etc.. Features a swimming pool with full screened outdoor patio surround, and lush tropical landscaping with palms, orchids, agave, and mature mango trees. Two cistern tanks for watering plants,

  Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  83 Sugarloaf Dr, Summerland Key, FL 33042
• 

  

  /47

  $1,100,000

  Sold Jun 12, 2026

  43 Venetian Way, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Built 1982

  Last Sold Summary

  • 17% Below List Price
  • $880/SF
  • 497 Days On Market

  Current Estimated Value $1,104,521

  Last Listing Agent Lori Cameron Buy The Keys

  43 Venetian Way, Summerland Key, FL 33042
• 

  

  /29

  Est $1,772,526

  Not Listed For Sale

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft
  • Built 1963

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  Last Sold Summary

  • 275 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /4

  $100,000

  Pending

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

  0 Acosta Trail Unit MFRS5141973, Sugarloaf 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,

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042
• 

  

  /61

  $750,000

  Sold Jul 31, 2026

  17326 Jamaica Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 1987

  Last Sold Summary

  • 18% Below List Price
  • $493/SF
  • 115 Days On Market

  Current Estimated Value $862,948

  Last Listing Agent Stephanie Wise Keller Williams Key West Compass Realty

  17326 Jamaica Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,257,321

  Not Listed For Sale

  19563 Canal Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft
  • Built 1990

  19563 Canal Dr, Summerland Key, FL 33042
• 

  

  /3

  $799,000

  $50K PRICE DROP Pending

  • Land
  • 10 Acres
  • $79,900 per Acre

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042

  Rare opportunity to acquire approximately 10 acres of vacant residential land in Sugarloaf Key, an area known for its low-density character, natural surroundings, and limited land availability. Large parcels of this size are increasingly scarce in the Lower Florida Keys, positioning this property as a strategic long-term holding or future planning opportunity. On Monroe county records, the

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042
• 

  

  /64

  $1,425,000

  Sold May 28, 2026

  17215 Bonita Ln E, Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Built 2008

  Last Sold Summary

  • 5% Below List Price
  • $933/SF
  • 71 Days On Market

  Current Estimated Value $1,422,883

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17215 Bonita Ln E, Sugarloaf Key, FL 33042
• 

  

  /56

  Est $1,697,564

  Not Listed For Sale

  17159 Amberjack Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • Built 1989

  17159 Amberjack Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 258 Days On Market

  Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty
• 

  

  /23

  $705,000

  $90K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  180 Sugarloaf Dr, Summerland Key, FL 33042

  **BACK ON THE MARKE, BUYERS FINANCING FELL THROUGH **This charming 3 bedroom 2 bath house in Sugarloaf Shores sits on an oversized 12,000 sq ft lot. Fenced for privacy with plenty of room for a pool, park your boat or RV. Outside you have a large paver patio, outdoor shower and lush gardens. Step inside to find a warm inviting interior space, remodeled kitchen and bathroom, bonus HUGE

  Jenny Perry Preferred Properties (KW)

  180 Sugarloaf Dr, Summerland Key, FL 33042
• 

  

  /32

  $970,000

  Sold Jul 08, 2026

  17287 Cayman Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 2013

  Last Sold Summary

  • 3% Below List Price
  • $652/SF
  • 42 Days On Market

  Current Estimated Value $1,042,746

  Last Listing Agent Jonathan Minerick Homecoin.com

  17287 Cayman Dr, Summerland Key, FL 33042
• 

  

  /82

  Est $1,880,869

  Not Listed For Sale

  17175 Allamanda Dr W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,116 Sq Ft
  • Built 1999

  17175 Allamanda Dr W, Summerland Key, FL 33042

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty
• 

  

  /143

  $19,750,000

  • 6 Beds
  • 6.5 Baths
  • 4,402 Sq Ft

  15760 Old State Road 4a, Summerland Key, FL 33042

  RARE PRIVATE SANDY BEACH | OCEANFRONT ESTATE | 30 MINUTES TO KEY WESTA truly extraordinary opportunity on coveted Sugarloaf Beach--over 5 acres of private oceanfront property offering endless open-water views, exceptional privacy and a rare natural sandy beach in the Lower Keys. This remarkable estate includes two County-recognized residential dwelling units with an established history of

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  15760 Old State Road 4a, Summerland Key, FL 33042
• 

  

  /19

  $650,000

  Sold Mar 20, 2026

  14 Coral Dr, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1989

  Last Sold Summary

  • 4% Below List Price
  • $565/SF
  • 9 Days On Market

  Current Estimated Value $683,917

  Last Listing Agent Christopher Scott,PA Expert Realty LLC (HQ)

  14 Coral Dr, Key West, FL 33040
• 

  /2

  Est $783,918

  Not Listed For Sale

  19720 Date Palm Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft
  • Built 1958

  19720 Date Palm Dr, Summerland Key, FL 33042
• 

  

  /3

  $799,000

  $50K PRICE DROP Pending

  • Land
  • 10 Acres
  • $79,934 per Acre

  0 Rocky Rd, Sugarloaf Key, FL 33042

  Rare opportunity to acquire approximately 10 acres of vacant residential land in Sugarloaf Key, an area known for its low-density character, natural surroundings, and limited land availability. Large parcels of this size are increasingly scarce in the Lower Florida Keys, positioning this property as a strategic long-term holding or future planning opportunity. On Monroe county records, the

  Eugenia Hernandez Premium Properties R.E. Svc.

  0 Rocky Rd, Sugarloaf Key, FL 33042

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