Sugarloaf Key, FL Homes

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  /11

  $475,000

  Sold May 27, 2026

  19264 Acosta Trail, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 832 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $571/SF
  • 9 Days On Market

  Current Estimated Value $441,960

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  19264 Acosta Trail, Summerland Key, FL 33042
• 

  

  

  /45

  Est $1,978,522

  Not Listed For Sale

  19527 Indian Mound Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,752 Sq Ft
  • Built 1996

  19527 Indian Mound Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 96 Days On Market

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

  

  

  /43

  $1,100,000

  • Land
  • 2,613 Sq Ft
  • $18,333,333 per Acre

  2950 Overseas Hwy Unit 57, Key West, FL 33040

  Golden Bayside RV Lot in Bluewater Key RV Resort! Discover Lot #57 in the prestigious 'Bluewater Key RV Resort', one of America's top-rated RV communities just 10 miles from Key West. This coveted Golden-rated lot offers a perfect blend of comfort and adventure in a private bayside setting.Highlights include a spacious tiki hut ideal for entertaining, relaxing, or soaking in the tropical

  Oleksandr Khiznichenko Keller Williams Key West Compass Realty

  2950 Overseas Hwy Unit 57, Key West, FL 33040
• 

  

  

  /29

  $360,000

  Sold Jul 24, 2026

  17 Palm Dr, Key West, FL 33040

  • 2 Beds
  • 1 Bath
  • 812 Sq Ft
  • Built 1984

  Last Sold Summary

  • 10% Below List Price
  • $443/SF
  • 8 Days On Market

  Last Listing Agent Tonya Cabanas Truman & Co. (KW)

  17 Palm Dr, Key West, FL 33040
• 

  

  

  /29

  Est $1,031,856

  Not Listed For Sale

  1107 Hawksbill Ln, Summerland Key, FL 33042

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

  1107 Hawksbill Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Richard Haskins Buy The Keys
• 

  

  /70

  $950,000

  Open Sun 10AM - 12PM

  • 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
• 

  

  /116

  $1,725,000

  Sold May 01, 2026

  78 Bay Dr, Key West, FL 33040

  • 4 Beds
  • 4 Baths
  • 2,454 Sq Ft
  • Built 1963

  Last Sold Summary

  • 44% Above List Price
  • $703/SF
  • 206 Days On Market

  Current Estimated Value $1,701,418

  Last Listing Agent Jenny Benson Coastal Collection Real Estate Inc.

  78 Bay Dr, Key West, FL 33040
• 

  /2

  Est $774,442

  Not Listed For Sale

  19514 Canal Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1995

  19514 Canal Dr, Summerland Key, FL 33042
• 

  

  /19

  $100,000

  • Land
  • 30.75 Acres
  • $3,252 per Acre

  14 67 26 Saddlebunch Key, Saddlebunch, FL 33040

  30 acres, two private islands on the gulf side of Saddlebunch Key. Not buildable, use can be private recreation, eco-preservation, or conservation. Listing includes parcel00120060-000000 and parcel 00120080-000000.If you love nature, here's s your spot!

  The Florida Keys Sold Sisters Ocean Sotheby's International Realty

  14 67 26 Saddlebunch Key, Saddlebunch, FL 33040
• 

  

  /7

  $3,500

  Sold May 24, 2026

  19525 Date Palm Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2006

  Last Sold Summary

  • 9% Below List Price
  • $3/SF
  • 20 Days On Market

  Current Estimated Value $793,317

  Last Listing Agent Cliff Glansen FlatFee.com

  19525 Date Palm Dr, Summerland Key, FL 33042
• 

  

  /5

  Est $740,553

  Not Listed For Sale

  19462 Canal Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft
  • Built 1990

  19462 Canal Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Jacqui Norman Berkshire Hathaway HomeServices Knight & Gardner Realty
• 

  

  /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
• 

  /2

  $75,000

  Sold Jun 29, 2026

  Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042

  • Land
  • 14,810 Sq Ft
  • $220,588 per Acre

  Last Sold Summary

  • 83% Below List Price
  • 346 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
• 

  

  /42

  Est $549,775

  Not Listed For Sale

  92 Frazier Ln, Summerland Key, FL 33042

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

  92 Frazier Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 43 Days On Market

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

  

  /61

  $3,900,000

  Sold Feb 27, 2026

  16200 Old State Rd Unit 4A, Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,964 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $1,986/SF
  • 25 Days On Market

  Current Estimated Value $3,861,398

  Last Listing Agent Madeleine Young Island Welcome Real Estate LLC

  16200 Old State Rd Unit 4A, Sugarloaf Key, FL 33042
• 

  

  /26

  Est $521,324

  Not Listed For Sale

  19910 Flamingo Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft
  • Built 1947

  19910 Flamingo Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Melissa Graham Bluescape Real Estate
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  /4

  $100,000

  Pending

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

  0 Acosta Rd, Summerland 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. Svc.

  0 Acosta Rd, Summerland Key, FL 33042
• 

  

  /17

  $850,000

  Sold Mar 30, 2026

  17171 Seagrape Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft
  • Built 1982

  Last Sold Summary

  • 22% Below List Price
  • $607/SF
  • 132 Days On Market

  Current Estimated Value $943,256

  Last Listing Agent Marie Howe Century 21 Circle - Key West

  17171 Seagrape Ln, Summerland Key, FL 33042
• 

  /2

  Est $610,599

  Not Listed For Sale

  19616 Aztec St, Summerland Key, FL 33042

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

  19616 Aztec St, Summerland Key, FL 33042
• 

  

  /49

  $1,175,000

  • Land
  • 3,051 Sq Ft
  • $16,770,315 per Acre

  2950 Overseas Hwy Unit 64, Key West, FL 33040

  Platinum opportunities in Bluewater Key are rare -- and Bayside Lot #64 is truly one of the finest. Located in the highly sought-after Bluewater Key Luxury RV Resort on Saddlebunch Key, this bayside property delivers an elevated RV lifestyle just minutes from Key West within one of the nation's most celebrated RV resort communities.Designated as a Platinum Lot, this is one of the resort's

  Oleksandr Khiznichenko Keller Williams Key West Compass Realty

  2950 Overseas Hwy Unit 64, Key West, FL 33040
• 

  

  /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

  Current Estimated Value $1,832,486

  Last Listing Agent Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  17054 Coral Dr, Summerland Key, FL 33042
• 

  

  /26

  Est $1,239,013

  Not Listed For Sale

  105 S Point Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1984

  105 S Point Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Tara Thoman-Wood,P.A. Berkshire Hathaway Homeservices Knight & Gardner Realty
• 

  

  /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
• 

  

  /50

  $1,100,000

  Sold Mar 06, 2026

  19749 Date Palm Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,464 Sq Ft
  • Built 2017

  Last Sold Summary

  • 15% Below List Price
  • $446/SF
  • 151 Days On Market

  Current Estimated Value $1,202,083

  Last Listing Agent Richard Lively Coldwell Banker Schmitt Real Estate Co. (KW)

  19749 Date Palm Dr, Summerland Key, FL 33042
• 

  

  /32

  Est $1,819,710

  Not Listed For Sale

  17023 Allamanda Dr W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1979

  17023 Allamanda Dr W, Summerland Key, FL 33042

  Last Sold Summary

  • 77 Days On Market

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

  

  /4

  $100,000

  Pending

  • 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. Svc.

  0 Mira Rd, Sugerloaf, FL 33042
• 

  

  /52

  $1,650,000

  Sold Jan 28, 2026

  17213 Starfish Ln E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1993

  Last Sold Summary

  • 15% Below List Price
  • $943/SF
  • 111 Days On Market

  Current Estimated Value $1,641,455

  Last Listing Agent The Spottswood Team Truman & Co. (KW)

  17213 Starfish Ln E, Summerland Key, FL 33042
• 

  /2

  Est $1,809,412

  Not Listed For Sale

  17150 La Brisa Ct, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,810 Sq Ft
  • Built 1980

  17150 La Brisa Ct, Summerland Key, FL 33042
• 

  

  /43

  $599,000

  $50K PRICE DROP

  • Land
  • 2,613 Sq Ft
  • $9,983,333 per Acre

  2950 Overseas Hwy Unit 33, Key West, FL 33040

  Welcome to Lot 33 at Bluewater Luxury RV Resort -- a premier destination for upscale RV living in the Florida Keys.This deeded Tropical Luxury RV lot offers an exceptional blend of comfort, convenience, and elegance in a lush, tropical setting. Spacious and level, Lot 33 easily accommodates your RV or motorhome and is surrounded by vibrant landscaping, swaying palms, and colorful island

  Oleksandr Khiznichenko Keller Williams Key West Compass Realty

  2950 Overseas Hwy Unit 33, Key West, FL 33040
• 

  

  /4

  $175,000

  Sold Dec 23, 2025

  Lot 2 Overseas Hwy, Summerland Key, FL 33042

  • Land
  • 12,500 Sq Ft
  • $609,840 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 25 Days On Market

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

  Lot 2 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /40

  Est $1,016,375

  Not Listed For Sale

  17236 Keystone Rd, Summerland Key, FL 33042

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

  17236 Keystone Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 184 Days On Market

  Last Listing Agent Everett Watkins Keller Williams Key West Compass Realty
• 

  

  /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
• 

  

  /67

  $1,900,000

  Sold Nov 06, 2025

  17077 Bonita Ln W, Summerland Key, FL 33042

  • 4 Beds
  • 3.5 Baths
  • 2,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Below List Price
  • $792/SF
  • 87 Days On Market

  Current Estimated Value $1,894,285

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17077 Bonita Ln W, Summerland Key, FL 33042
• 

  

  /59

  Est $2,271,050

  Not Listed For Sale

  17346 Keystone Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,192 Sq Ft
  • Built 2019

  17346 Keystone Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty
• 

  

  /55

  $2,299,999

  New Construction Under Contract

  • 3 Beds
  • 2.5 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
• 

  

  /74

  $2,650,000

  Sold Aug 10, 2026

  16805 Tamarind Rd, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,812 Sq Ft
  • Built 1978

  Last Sold Summary

  • 24% Below List Price
  • $942/SF
  • 140 Days On Market

  Current Estimated Value $3,011,505

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

  16805 Tamarind Rd, Summerland Key, FL 33042
• 

  

  /42

  Est $1,020,428

  Not Listed For Sale

  17214 La Brisa Ln, Summerland Key, FL 33042

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

  17214 La Brisa Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 50 Days On Market

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

  

  /56

  $799,000

  $16K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $15,980,000 per Acre

  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

  Oleksandr Khiznichenko Keller Williams Key West Compass Realty

  2950 Overseas Hwy Unit 2, Key West, FL 33040
• 

  

  /45

  $1,525,000

  Sold Mar 06, 2026

  17227 Allamanda Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • $853/SF
  • 96 Days On Market

  Current Estimated Value $1,532,383

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17227 Allamanda Dr, Summerland Key, FL 33042

Showing Results 121 - 160, Page 4 of 18