368

Recently Sold Summerland Key, FL Homes

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  • /9

    $2,150,000

    Sold Jun 25, 2026

    24356 Overseas Hwy, Summerland Key, FL 33042

    • Land
    • 23,958 Sq Ft
    • $3,909,091 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 254 Days On Market

    Last Listing Agent Scott Brisson KeyIsle Realty

    24356 Overseas Hwy, Summerland Key, FL 33042
  • /2

    $50,000

    Sold May 07, 2026

    12 Trin Ln, Torch Key, FL 33042

    • Land
    • 6,098 Sq Ft
    • $357,143 per Acre

    Last Sold Summary

    • 0 Days On Market

    12 Trin Ln, Torch Key, FL 33042
  • /64

    $650,000

    Sold Jun 30, 2026

    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft
    • Built 1997

    Last Sold Summary

    • 3% Below List Price
    • $797/SF
    • 62 Days On Market

    Last Listing Agent Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
  • /5

    $320,000

    Sold Apr 22, 2026

    248 Yardarm Rd, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 980 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Below List Price
    • $327/SF
    • 21 Days On Market

    Last Listing Agent Joe Ordini Keller Williams Key West Compass Realty

    248 Yardarm Rd, Cudjoe Key, FL 33042
  • /46

    $760,000

    Sold Nov 12, 2025

    30335 Warbler Ln, Big Pine Key, FL 33043

    • 4 Beds
    • 3 Baths
    • 2,285 Sq Ft
    • Built 1973

    Last Sold Summary

    • 20% Below List Price
    • $333/SF
    • 254 Days On Market

    Current Estimated Value $839,113

    Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.

    30335 Warbler Ln, Big Pine Key, FL 33043
  • /27

    $724,000

    Sold Oct 20, 2025

    25081 Overseas Hwy, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft
    • Built 2006

    Last Sold Summary

    • 4% Above List Price
    • $633/SF
    • 75 Days On Market

    Current Estimated Value $770,691

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    25081 Overseas Hwy, Summerland Key, FL 33042
  • /28

    $375,000

    Sold Aug 25, 2026

    290 46th St, Summerland Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 1,184 Sq Ft
    • Built 1958

    Last Sold Summary

    • 12% Below List Price
    • $317/SF
    • 43 Days On Market

    Current Estimated Value $411,000

    Last Listing Agent Christina Davis Coldwell Banker Schmitt RE Co.

    290 46th St, Summerland Key, FL 33042
  • /41

    $835,000

    Sold May 29, 2026

    154 Cutthroat Dr, Summerland Key, FL 33042

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

    Last Sold Summary

    • 4% Below List Price
    • $870/SF
    • 50 Days On Market

    Current Estimated Value $841,000

    Last Listing Agent Pamela Stangler Expert Realty LLC

    154 Cutthroat Dr, Summerland Key, FL 33042
  • /52

    $1,006,000

    Sold Mar 19, 2026

    27360 Barbados Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft
    • Built 1995

    Last Sold Summary

    • 4% Below List Price
    • $967/SF
    • 21 Days On Market

    Current Estimated Value $1,006,361

    Last Listing Agent Brian Kruszewski LoKation Real Estate

    27360 Barbados Ln, Summerland Key, FL 33042
  • /39

    $1,100,000

    Sold Apr 27, 2026

    857 Caribbean Dr E, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 1987

    Last Sold Summary

    • 15% Below List Price
    • $914/SF
    • 112 Days On Market

    Current Estimated Value $1,110,181

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    857 Caribbean Dr E, Summerland Key, FL 33042
  • /2

    $175,000

    Sold Dec 10, 2025

    ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042

    • Land
    • 1.78 Acres
    • $98,361 per Acre

    Last Sold Summary

    • 17% Below List Price
    • 23 Days On Market

    Last Listing Agent Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

    ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042
  • /38

    $887,000

    Sold Jan 27, 2026

    1633 Lantana Ln, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 2021

    Last Sold Summary

    • 11% Below List Price
    • $737/SF
    • 265 Days On Market

    Current Estimated Value $915,989

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    1633 Lantana Ln, Big Pine Key, FL 33043
  • /2

    $2,030,000

    Sold Nov 17, 2025

    27450 W Indies Dr, Summerland Key, FL 33042

    • 2 Beds
    • 4 Baths
    • 1,968 Sq Ft
    • Built 1984

    Last Sold Summary

    • 22% Below List Price
    • $1,032/SF
    • 273 Days On Market

    Current Estimated Value $2,209,291

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

    27450 W Indies Dr, Summerland Key, FL 33042
  • /30

    $400,000

    Sold Jun 26, 2026

    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 748 Sq Ft
    • Built 1987

    Last Sold Summary

    • 20% Below List Price
    • $535/SF
    • 481 Days On Market

    Last Listing Agent Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 342, Cudjoe 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 $2,894,333

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

    16805 Tamarind Rd, Summerland Key, FL 33042
  • /60

    $938,000

    Sold Dec 11, 2025

    460 Barry Ave, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1985

    Last Sold Summary

    • 22% Below List Price
    • $651/SF
    • 196 Days On Market

    Current Estimated Value $991,015

    Last Listing Agent Noel Betancourt Tropic Shores Realty

    460 Barry Ave, Summerland Key, FL 33042
  • /38

    $1,460,000

    Sold Jul 02, 2026

    1113 de Lussan Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,127 Sq Ft
    • Built 1992

    Last Sold Summary

    • $1,295/SF
    • 0 Days On Market

    Current Estimated Value $1,440,406

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    1113 de Lussan Ln, Summerland Key, FL 33042
  • /82

    $2,495,000

    Sold Mar 02, 2026

    835 Gulf Dr, Summerland Key, FL 33042

    • 4 Beds
    • 3.5 Baths
    • 2,416 Sq Ft
    • Built 2023

    Last Sold Summary

    • 11% Below List Price
    • $1,033/SF
    • 195 Days On Market

    Current Estimated Value $2,526,832

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    835 Gulf Dr, Summerland Key, FL 33042
  • /25

    $625,000

    Sold Jan 20, 2026

    29849 Newfound Blvd, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,201 Sq Ft
    • Built 1977

    Last Sold Summary

    • 21% Below List Price
    • $520/SF
    • 160 Days On Market

    Current Estimated Value $669,753

    Last Listing Agent Taron Wirth Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    29849 Newfound Blvd, Big Pine Key, FL 33043
  • /49

    $1,300,000

    Sold Aug 24, 2026

    27372 W Indies Dr, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • Built 2020

    Last Sold Summary

    • 13% Below List Price
    • $722/SF
    • 137 Days On Market

    Current Estimated Value $1,421,730

    Last Listing Agent Sandra Dolowy KeyIsle Realty

    27372 W Indies Dr, Summerland Key, FL 33042
  • /5

    $170,000

    Sold Dec 04, 2025

    27313 Antigua Rd, Ramrod Key, FL 33042

    • Land
    • 6,000 Sq Ft
    • $1,234,200 per Acre

    Last Sold Summary

    • 41% Below List Price
    • 7 Days On Market

    Current Estimated Value $167,000

    Last Listing Agent Pamela Stangler Expert Realty LLC

    27313 Antigua Rd, Ramrod Key, FL 33042
  • /50

    $635,000

    Sold Mar 09, 2026

    31047 Avenue I, Big Pine Key, FL 33043

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Built 2007

    Last Sold Summary

    • 9% Below List Price
    • $423/SF
    • 97 Days On Market

    Current Estimated Value $656,787

    Last Listing Agent Loren Rea Truman & Co. (KW)

    31047 Avenue I, Big Pine Key, FL 33043
  • /47

    $935,000

    Sold Dec 31, 2025

    786 Jamaica Ln, Little Torch Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 2016

    Last Sold Summary

    • 5% Below List Price
    • $649/SF
    • 89 Days On Market

    Current Estimated Value $942,730

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    786 Jamaica Ln, Little Torch Key, FL 33042
  • /5

    $840,000

    Sold Mar 03, 2026

    23012 Snapper Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 950 Sq Ft
    • Built 2004

    Last Sold Summary

    • 7% Below List Price
    • $884/SF
    • 113 Days On Market

    Current Estimated Value $873,758

    Last Listing Agent Bobby Coe RE/MAX Keys Connection (KW)

    23012 Snapper Ln, Summerland Key, FL 33042
  • /3

    $75,000

    Sold Dec 08, 2025

    29141 Mango Ln, Big Pine Key, FL 33043

    • Land
    • 6,999 Sq Ft
    • $466,714 per Acre

    Last Sold Summary

    • 42% Below List Price
    • 14 Days On Market

    Current Estimated Value $77,000

    Last Listing Agent David Kaufmann Century 21 Circle

    29141 Mango Ln, Big Pine Key, FL 33043
  • /33

    $1,100,000

    Sold Jul 06, 2026

    3167 Stewart Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,222 Sq Ft
    • Built 1971

    Last Sold Summary

    • 31% Below List Price
    • $900/SF
    • 67 Days On Market

    Current Estimated Value $1,197,877

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

    3167 Stewart Rd, Summerland Key, FL 33042
  • /27

    $905,000

    Sold Dec 11, 2025

    22852 John Silver Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 1980

    Last Sold Summary

    • 5% Below List Price
    • $559/SF
    • 75 Days On Market

    Current Estimated Value $949,782

    Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

    22852 John Silver Ln, Summerland Key, FL 33042
  • /45

    $565,000

    Sold Sep 29, 2025

    2421 Pensacola Rd, Big Pine Key, FL 33043

    • 3 Beds
    • 1 Bath
    • 1,055 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $536/SF
    • 101 Days On Market

    Current Estimated Value $580,725

    Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

    2421 Pensacola Rd, Big Pine Key, FL 33043
  • /86

    $5,250,000

    Sold Feb 23, 2026

    4500 Filer Cove Rd, Summerland Key, FL 33042

    • 4 Beds
    • 4 Baths
    • 4,315 Sq Ft
    • Built 1994

    Last Sold Summary

    • 12% Below List Price
    • $1,217/SF
    • 246 Days On Market

    Current Estimated Value $5,455,224

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    4500 Filer Cove Rd, Summerland Key, FL 33042
  • /74

    $750,000

    Sold Apr 24, 2026

    701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 766 Sq Ft
    • Built 1989

    Last Sold Summary

    • 6% Below List Price
    • $979/SF
    • 90 Days On Market

    Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042
  • /75

    $1,265,000

    Sold Apr 27, 2026

    29653 Saratoga Ave, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,596 Sq Ft
    • Built 1980

    Last Sold Summary

    • 2% Below List Price
    • $793/SF
    • 3 Days On Market

    Current Estimated Value $1,279,748

    Last Listing Agent Patti Nickless Coldwell Banker Schmitt Real E

    29653 Saratoga Ave, Big Pine Key, FL 33043
  • /47

    $1,400,000

    Sold Sep 18, 2026

    1136 W Shore Dr, Big Pine Key, FL 33043

    • 3 Beds
    • 3.5 Baths
    • 2,295 Sq Ft
    • Built 1966

    Last Sold Summary

    • 12% Below List Price
    • $610/SF

    Current Estimated Value $1,658,579

    Last Listing Agent Beata Sharpe COLDWELL BANKER VANGUARD REALTY

    1136 W Shore Dr, Big Pine Key, FL 33043
  • /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 $1,548,467

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17227 Allamanda Dr, Summerland Key, FL 33042
  • /20

    $600,000

    Sold Nov 20, 2025

    9 W, Cook Island Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 574 Sq Ft
    • Built 1948

    Last Sold Summary

    • 20% Below List Price
    • $1,045/SF
    • 31 Days On Market

    Current Estimated Value $752,500

    Last Listing Agent Greg Gordon The Island Collective Realty

    9 W, Cook Island Key, FL 33043
  • /2

    $390,000

    Sold Apr 29, 2026

    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 2002

    Last Sold Summary

    • 5% Below List Price
    • $451/SF
    • 61 Days On Market

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
  • /54

    $1,650,000

    Sold Feb 27, 2026

    27365 Barbuda Ln, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,198 Sq Ft
    • Built 1996

    Last Sold Summary

    • 11% Below List Price
    • $751/SF
    • 73 Days On Market

    Current Estimated Value $1,637,621

    Last Listing Agent Halley Haack Coldwell Banker Schmitt RE Co.

    27365 Barbuda Ln, Summerland Key, FL 33042
  • /42

    $825,000

    Sold Aug 18, 2026

    324 Airport Dr S, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1981

    Last Sold Summary

    • 11% Below List Price
    • $859/SF
    • 34 Days On Market

    Current Estimated Value $855,016

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

    324 Airport Dr S, 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
  • /7

    $737,000

    Sold Mar 31, 2026

    701 Spanish Main Dr Unit LOT 102, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 865 Sq Ft
    • Built 2005

    Last Sold Summary

    • 4% Below List Price
    • $852/SF
    • 1 Day On Market

    Last Listing Agent Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 102, Cudjoe Key, FL 33042
  • /41

    $2,425,000

    Sold Nov 21, 2025

    281 W Indies Dr, Summerland Key, FL 33042

    • 3 Beds
    • 3.5 Baths
    • 2,914 Sq Ft
    • Built 2020

    Last Sold Summary

    • 12% Below List Price
    • $832/SF
    • 203 Days On Market

    Current Estimated Value $2,492,559

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    281 W Indies Dr, Summerland Key, FL 33042

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