1,773

Sugarloaf Key, FL Homes

Section Image
    • 17213 Snapper Ln, Summerland Key, FL 33042
      17213 Snapper Ln, Summerland Key, FL 33042
      17213 Snapper Ln, Summerland Key, FL 33042
      /23

      Est $853,641

      Not Listed For Sale

      17213 Snapper Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,008 Sq Ft
      • Built 1988
      17213 Snapper Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Wendy Holifield Berkshire Hathaway HomeServices Knight & Gardner Realty

  • 231 E Shore Dr Unit 2, Key West, FL 33040
    231 E Shore Dr Unit 2, Key West, FL 33040
    231 E Shore Dr Unit 2, Key West, FL 33040
    /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
  • 16805 Tamarind Rd, Summerland Key, FL 33042
    16805 Tamarind Rd, Summerland Key, FL 33042
    16805 Tamarind Rd, 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
    • 19648 Caribe St, Summerland Key, FL 33042
      19648 Caribe St, Summerland Key, FL 33042
      19648 Caribe St, Summerland Key, FL 33042
      /26

      Est $924,154

      Not Listed For Sale

      19648 Caribe St, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 961 Sq Ft
      • Built 1957
      19648 Caribe St, Summerland Key, FL 33042

      Last Sold Summary

      • 176 Days On Market

      Last Listing Agent Rey Delgado Cohen & Roth, LLC

  • 17227 Allamanda Dr, Summerland Key, FL 33042
    17227 Allamanda Dr, Summerland Key, FL 33042
    17227 Allamanda Dr, Summerland Key, FL 33042
    /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
    • 19518 Caloosa St, Summerland Key, FL 33042
      19518 Caloosa St, Summerland Key, FL 33042
      19518 Caloosa St, Summerland Key, FL 33042
      /21

      Est $716,051

      Not Listed For Sale

      19518 Caloosa St, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,143 Sq Ft
      • Built 1992
      19518 Caloosa St, Summerland Key, FL 33042

      Last Sold Summary

      • 159 Days On Market

      Last Listing Agent Wendy Holifield Berkshire Hathaway HomeServices Knight & Gardner Realty

  • 19594 Caloosa St Unit LOT 29, Summerland Key, FL 33042
    19594 Caloosa St Unit LOT 29, Summerland Key, FL 33042
    /2

    $70,000

    Sold Aug 12, 2026

    19594 Caloosa St Unit LOT 29, Summerland Key, FL 33042

    • Land
    • 4,791 Sq Ft
    • $636,364 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Mike Kane Internet Realty of the Florida Keys

    19594 Caloosa St Unit LOT 29, Summerland Key, FL 33042
    • 20 Shore Dr, Key West, FL 33040
      20 Shore Dr, Key West, FL 33040
      20 Shore Dr, Key West, FL 33040
      /15

      Est $930,019

      Not Listed For Sale

      20 Shore Dr, Key West, FL 33040

      • 2 Beds
      • 2 Baths
      • 1,513 Sq Ft
      • Built 1953
      20 Shore Dr, Key West, FL 33040

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  • 17144 Coral Dr, Summerland Key, FL 33042
    17144 Coral Dr, Summerland Key, FL 33042
    17144 Coral Dr, Summerland Key, FL 33042
    /45

    $1,200,000

    Sold Feb 23, 2026

    17144 Coral Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,437 Sq Ft
    • Built 1993

    Last Sold Summary

    • 7% Below List Price
    • $835/SF
    • 162 Days On Market

    Current Estimated Value $1,224,818

    Last Listing Agent Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    17144 Coral Dr, Summerland Key, FL 33042
    • 46 Blue Water Dr, Key West, FL 33040
      46 Blue Water Dr, Key West, FL 33040
      46 Blue Water Dr, Key West, FL 33040
      /64

      Est $1,368,085

      Not Listed For Sale

      46 Blue Water Dr, Key West, FL 33040

      • 3 Beds
      • 2 Baths
      • 1,728 Sq Ft
      • Built 2007
      46 Blue Water Dr, Key West, FL 33040

      Last Sold Summary

      • 178 Days On Market

      Last Listing Agent Emily Lombard Saltwater Real Estate Florida Keys, Inc

  • 37 Blue Water Dr, Key West, FL 33040
    37 Blue Water Dr, Key West, FL 33040
    37 Blue Water Dr, Key West, FL 33040
    /45

    $5,000

    Sold May 01, 2026

    37 Blue Water Dr, Key West, FL 33040

    • 2 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1983

    Last Sold Summary

    • $4/SF
    • 17 Days On Market

    Current Estimated Value $1,014,315

    Last Listing Agent Justyn Ewald Expert Realty LLC

    37 Blue Water Dr, Key West, FL 33040
    • 340 S Point Dr, Summerland Key, FL 33042
      340 S Point Dr, Summerland Key, FL 33042
      340 S Point Dr, Summerland Key, FL 33042
      /43

      Est $2,399,615

      Not Listed For Sale

      340 S Point Dr, Summerland Key, FL 33042

      • 4 Beds
      • 4 Baths
      • 2,935 Sq Ft
      • Built 1973
      340 S Point Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 214 Days On Market

      Last Listing Agent Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

  • 17230 Angelfish Ln, Sugarloaf Shores, FL 33042
    17230 Angelfish Ln, Sugarloaf Shores, FL 33042
    17230 Angelfish Ln, Sugarloaf Shores, FL 33042
    /12

    $687,500

    Sold Mar 16, 2026

    17230 Angelfish Ln, Sugarloaf Shores, FL 33042

    • Land
    • 8,164 Sq Ft
    • $3,667,789 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 136 Days On Market

    Current Estimated Value $689,695

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

    17230 Angelfish Ln, Sugarloaf Shores, FL 33042
    • 33 Bay Dr, Key West, FL 33040
      33 Bay Dr, Key West, FL 33040
      33 Bay Dr, Key West, FL 33040
      /35

      Est $1,579,235

      Not Listed For Sale

      33 Bay Dr, Key West, FL 33040

      • 3 Beds
      • 3 Baths
      • 2,181 Sq Ft
      • Built 1958
      33 Bay Dr, Key West, FL 33040

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Dawn McComish Lokation Real Estate

  • 19611 Tequesta St, Summerland Key, FL 33042
    19611 Tequesta St, Summerland Key, FL 33042
    19611 Tequesta St, Summerland Key, FL 33042
    /64

    $810,000

    Sold May 29, 2026

    19611 Tequesta St, Summerland Key, FL 33042

    • 3 Beds
    • 2.5 Baths
    • 1,592 Sq Ft
    • Built 1992

    Last Sold Summary

    • 5% Below List Price
    • $509/SF
    • 104 Days On Market

    Current Estimated Value $862,000

    Last Listing Agent Jessica Forsythe eXp Realty LLC Southernmost Branch

    19611 Tequesta St, Summerland Key, FL 33042
    • 35 Palm Dr, Key West, FL 33040
      35 Palm Dr, Key West, FL 33040
      35 Palm Dr, Key West, FL 33040
      /56

      Est $653,763

      Not Listed For Sale

      35 Palm Dr, Key West, FL 33040

      • 3 Beds
      • 2 Baths
      • 1,173 Sq Ft
      • Built 1978
      35 Palm Dr, Key West, FL 33040

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Tracey Petrusha LoKation

  • 146 Sugarloaf Dr, Summerland Key, FL 33042
    146 Sugarloaf Dr, Summerland Key, FL 33042
    146 Sugarloaf Dr, Summerland Key, FL 33042
    /55

    $935,000

    Sold Jan 20, 2026

    146 Sugarloaf Dr, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 1,859 Sq Ft
    • Built 1995

    Last Sold Summary

    • $503/SF
    • 0 Days On Market

    Current Estimated Value $1,040,277

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    146 Sugarloaf Dr, Summerland Key, FL 33042
    • 85 Bay Dr, Key West, FL 33040
      85 Bay Dr, Key West, FL 33040
      85 Bay Dr, Key West, FL 33040
      /51

      Est $2,817,215

      Not Listed For Sale

      85 Bay Dr, Key West, FL 33040

      • 3 Beds
      • 2.5 Baths
      • 2,380 Sq Ft
      • Built 2016
      85 Bay Dr, Key West, FL 33040

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Leigh Ann Roach Berkshire Hathaway HomeServices Knight & Gardner Realty

  • 2950 Overseas Hwy Unit 16, Key West, FL 33040
    2950 Overseas Hwy Unit 16, Key West, FL 33040
    2950 Overseas Hwy Unit 16, Key West, FL 33040
    /3

    $1,050,000

    Sold Mar 13, 2026

    2950 Overseas Hwy Unit 16, Key West, FL 33040

    • Land
    • 4,165 Sq Ft
    • $10,978,877 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 11 Days On Market

    Current Estimated Value $1,058,898

    Last Listing Agent Oleksandr Khiznichenko Keller Williams Key West Compass Realty

    2950 Overseas Hwy Unit 16, Key West, FL 33040
    • 17177 Bonita Ln W, Summerland Key, FL 33042
      17177 Bonita Ln W, Summerland Key, FL 33042
      17177 Bonita Ln W, Summerland Key, FL 33042
      /42

      Est $1,462,541

      Not Listed For Sale

      17177 Bonita Ln W, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,425 Sq Ft
      • Built 1978
      17177 Bonita Ln W, Summerland Key, FL 33042

      Last Sold Summary

      • 362 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • 16640 Cypress Rd, Summerland Key, FL 33042
    16640 Cypress Rd, Summerland Key, FL 33042
    16640 Cypress Rd, Summerland Key, FL 33042
    /86

    $1,595,000

    Sold Jul 24, 2026

    16640 Cypress Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,764 Sq Ft
    • Built 1991

    Last Sold Summary

    • 18% Below List Price
    • $904/SF
    • 7 Days On Market

    Current Estimated Value $1,638,732

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

    16640 Cypress Rd, Summerland Key, FL 33042
    • 19461 Canal Dr, Summerland Key, FL 33042
      19461 Canal Dr, Summerland Key, FL 33042
      19461 Canal Dr, Summerland Key, FL 33042
      /48

      Est $637,367

      Not Listed For Sale

      19461 Canal Dr, Summerland Key, FL 33042

      • 3 Beds
      • 1 Bath
      • 1,136 Sq Ft
      • Built 1963
      19461 Canal Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 84 Days On Market

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

  • 17166 Wahoo Ln W, Summerland Key, FL 33042
    17166 Wahoo Ln W, Summerland Key, FL 33042
    17166 Wahoo Ln W, Summerland Key, FL 33042
    /48

    $1,400,000

    Sold Jan 14, 2026

    17166 Wahoo Ln W, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1982

    Last Sold Summary

    • 7% Below List Price
    • $810/SF
    • 172 Days On Market

    Current Estimated Value $1,415,220

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17166 Wahoo Ln W, Summerland Key, FL 33042
    • 70 Bay Dr, Key West, FL 33040
      70 Bay Dr, Key West, FL 33040
      70 Bay Dr, Key West, FL 33040
      /69

      Est $2,193,455

      Not Listed For Sale

      70 Bay Dr, Key West, FL 33040

      • 5 Beds
      • 2 Baths
      • 2,450 Sq Ft
      • Built 1993
      70 Bay Dr, Key West, FL 33040

      Last Sold Summary

      • 174 Days On Market

      Last Listing Agent Stephanie Wise Keller Williams Key West Compass Realty

  • 17137 Bonita Ln W, Summerland Key, FL 33042
    17137 Bonita Ln W, Summerland Key, FL 33042
    17137 Bonita Ln W, Summerland Key, FL 33042
    /32

    $850,000

    Sold Mar 17, 2026

    17137 Bonita Ln W, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Built 1988

    Last Sold Summary

    • 23% Below List Price
    • $611/SF
    • 240 Days On Market

    Current Estimated Value $905,065

    Last Listing Agent Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    17137 Bonita Ln W, Summerland Key, FL 33042
    • 91 Frazier Ln, Summerland Key, FL 33042
      91 Frazier Ln, Summerland Key, FL 33042
      91 Frazier Ln, Summerland Key, FL 33042
      /29

      Est $869,173

      Not Listed For Sale

      91 Frazier Ln, Summerland Key, FL 33042

      • 4 Beds
      • 2 Baths
      • 1,544 Sq Ft
      • Built 1948
      91 Frazier Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 90 Days On Market

      Last Listing Agent Keys Team Bryant and Kat Expert Realty LLC (HQ)

  • Lot 15 bk2 Bad George Rd, Sugarloaf Key, FL 33042
    Lot 15 bk2 Bad George Rd, Sugarloaf Key, FL 33042
    Lot 15 bk2 Bad George Rd, Sugarloaf Key, FL 33042
    /7

    $150,000

    Sold Aug 03, 2026

    Lot 15 bk2 Bad George Rd, Sugarloaf Key, FL 33042

    • Land
    • 1.02 Acres
    • $147,059 per Acre

    Last Sold Summary

    • 21% Below List Price

    Last Listing Agent Elizabeth Greco-DeGrenier Coldwell Banker Schmitt RE Co.

    Lot 15 bk2 Bad George Rd, Sugarloaf Key, FL 33042
    • 17177 Dolphin St W, Summerland Key, FL 33042
      17177 Dolphin St W, Summerland Key, FL 33042
      /2

      Est $1,427,378

      Not Listed For Sale

      17177 Dolphin St W, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,216 Sq Ft
      • Built 1986
      17177 Dolphin St W, Summerland Key, FL 33042

    • 82 Palm Dr, Key West, FL 33040
      82 Palm Dr, Key West, FL 33040
      /2

      Est $1,261,720

      Not Listed For Sale

      82 Palm Dr, Key West, FL 33040

      • 2 Beds
      • 2 Baths
      • 1,528 Sq Ft
      • Built 1988
      82 Palm Dr, Key West, FL 33040

    • 9 Bay Dr, Key West, FL 33040
      9 Bay Dr, Key West, FL 33040
      9 Bay Dr, Key West, FL 33040
      /67

      Est $3,550,037

      Not Listed For Sale

      9 Bay Dr, Key West, FL 33040

      • 5 Beds
      • 4.5 Baths
      • 3,272 Sq Ft
      • Built 2014
      9 Bay Dr, Key West, FL 33040

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Dan Serban Key West Luxury Real Estate Inc (KW)

    • 23 Boulder Dr, Key West, FL 33040
      23 Boulder Dr, Key West, FL 33040
      /2

      Est $1,778,963

      Not Listed For Sale

      23 Boulder Dr, Key West, FL 33040

      • 3 Beds
      • 3 Baths
      • 2,209 Sq Ft
      • Built 1956
      23 Boulder Dr, Key West, FL 33040

    • 96 Bay Dr, Key West, FL 33040
      96 Bay Dr, Key West, FL 33040
      96 Bay Dr, Key West, FL 33040
      /18

      Est $1,250,168

      Not Listed For Sale

      96 Bay Dr, Key West, FL 33040

      • 2 Beds
      • 1 Bath
      • 1,026 Sq Ft
      • Built 1976
      96 Bay Dr, Key West, FL 33040

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Barbara Crespo Coldwell Banker Schmitt Real Estate Co. (KW)

    • 17182 Starfish Ln W, Summerland Key, FL 33042
      17182 Starfish Ln W, Summerland Key, FL 33042
      17182 Starfish Ln W, Summerland Key, FL 33042
      /35

      Est $1,051,982

      Not Listed For Sale

      17182 Starfish Ln W, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,265 Sq Ft
      • Built 1991
      17182 Starfish Ln W, Summerland Key, FL 33042

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Daniel Urban Expert Realty LLC (HQ)

    • 17279 Pinetree Ln, Summerland Key, FL 33042
      17279 Pinetree Ln, Summerland Key, FL 33042
      17279 Pinetree Ln, Summerland Key, FL 33042
      /33

      Est $2,324,070

      Not Listed For Sale

      17279 Pinetree Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,016 Sq Ft
      • Built 1956
      17279 Pinetree Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 288 Days On Market

      Last Listing Agent Dan Serban Key West Luxury Real Estate Inc (KW)

    • 17365 Keystone Rd, Summerland Key, FL 33042
      17365 Keystone Rd, Summerland Key, FL 33042
      17365 Keystone Rd, Summerland Key, FL 33042
      /47

      Est $1,684,018

      Not Listed For Sale

      17365 Keystone Rd, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1995
      17365 Keystone Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Daniel Urban Expert Realty LLC (HQ)

    • 81 Johnson Rd, Summerland Key, FL 33042
      81 Johnson Rd, Summerland Key, FL 33042
      81 Johnson Rd, Summerland Key, FL 33042
      /23

      Est $324,536

      Not Listed For Sale

      81 Johnson Rd, Summerland Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 600 Sq Ft
      • Built 1943
      81 Johnson Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    • 17206 Jamaica Ln, Summerland Key, FL 33042
      17206 Jamaica Ln, Summerland Key, FL 33042
      17206 Jamaica Ln, Summerland Key, FL 33042
      /27

      Est $1,102,813

      Not Listed For Sale

      17206 Jamaica Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,326 Sq Ft
      • Built 2003
      17206 Jamaica Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 254 Days On Market

      Last Listing Agent Elizabeth Chamberlain Truman & Co. (KW)

    • 17024 Green Turtle Ln W, Summerland Key, FL 33042
      17024 Green Turtle Ln W, Summerland Key, FL 33042
      17024 Green Turtle Ln W, Summerland Key, FL 33042
      /70

      Est $4,060,010

      Not Listed For Sale

      17024 Green Turtle Ln W, Summerland Key, FL 33042

      • 4 Beds
      • 4 Baths
      • 3,014 Sq Ft
      • Built 1979
      17024 Green Turtle Ln W, Summerland Key, FL 33042

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    • 92 Bay Dr, Key West, FL 33040
      92 Bay Dr, Key West, FL 33040
      /2

      Est $1,340,214

      Not Listed For Sale

      92 Bay Dr, Key West, FL 33040

      • 3 Beds
      • 2 Baths
      • 1,443 Sq Ft
      • Built 1964
      92 Bay Dr, Key West, FL 33040

    • 257 Venetian Way, Summerland Key, FL 33042
      257 Venetian Way, Summerland Key, FL 33042
      257 Venetian Way, Summerland Key, FL 33042
      /30

      Est $1,141,129

      Not Listed For Sale

      257 Venetian Way, Summerland Key, FL 33042

      • 4 Beds
      • 2.5 Baths
      • 1,984 Sq Ft
      • Built 2015
      257 Venetian Way, Summerland Key, FL 33042

      Last Sold Summary

      • 70 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

Showing Results 161 - 200, Page 5 of 18

Florida Monroe County

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