Recently Sold Summerland Key, FL Homes

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  /21

  $1,000,000 Sold Aug 29, 2025

  419 Blackbeard Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 1988

  Last Sold Summary

  • 17% Below List Price
  • $952/SF
  • 250 Days On Market

  Current Estimated Value $957,041

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  419 Blackbeard Rd, Summerland Key, FL 33042
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  /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 $908,753

  Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

  22852 John Silver Ln, Summerland Key, FL 33042
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  /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 $569,916

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

  2421 Pensacola Rd, Big Pine Key, FL 33043
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  /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 $5,965,907

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  4500 Filer Cove Rd, Summerland Key, FL 33042
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  /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 $1,562,772

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17227 Allamanda Dr, Summerland Key, FL 33042
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  /61

  $1,636,000 Sold Aug 19, 2025

  227 La Fitte Rd, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 1,260 Sq Ft
  • Built 1982

  Last Sold Summary

  • 9% Below List Price
  • $1,298/SF
  • 6 Days On Market

  Current Estimated Value $1,610,719

  Last Listing Agent Jennifer Chaney Chaney Homes

  227 La Fitte Rd, Summerland Key, FL 33042
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  /36

  $925,050 Sold Apr 24, 2025

  3666 S Seas St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,519 Sq Ft
  • Built 1988

  Last Sold Summary

  • 18% Below List Price
  • $609/SF
  • 89 Days On Market

  Current Estimated Value $958,185

  Last Listing Agent Scott Brisson KeyIsle Realty

  3666 S Seas St, Big Pine Key, FL 33043
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  /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 $757,500

  Last Listing Agent Greg Gordon The Island Collective Realty

  9 W, Cook Island Key, FL 33043
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  /13

  $265,000 Sold Jun 30, 2025

  31014 Avenue E, Big Pine Key, FL 33043

  • Land

  Last Sold Summary

  • 29% Below List Price
  • 103 Days On Market

  Current Estimated Value $284,514

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

  31014 Avenue E, Big Pine Key, FL 33043
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  /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 $1,772,126

  Last Listing Agent Halley Haack Coldwell Banker Schmitt RE Co.

  27365 Barbuda Ln, Summerland Key, FL 33042
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  /39

  $1,116,000 Sold Jun 25, 2025

  591 Blackbeard Rd, Summerland Key, FL 33042

  • 4 Beds
  • 5 Baths
  • 2,512 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $444/SF
  • 25 Days On Market

  Current Estimated Value $1,199,538

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  591 Blackbeard Rd, Summerland Key, FL 33042
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  /46

  $1,900,000 Sold Mar 27, 2025

  271 W Indies Dr, Ramrod Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,358 Sq Ft
  • Built 2023

  Last Sold Summary

  • 36% Below List Price
  • $806/SF
  • 342 Days On Market

  Current Estimated Value $1,900,480

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  271 W Indies Dr, Ramrod Key, FL 33042
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  /2

  $49,000 Sold Sep 22, 2025

  Lot 23 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 23 Rainbow Beach, Big Torch Key, FL 33042
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  /40

  $825,000 Sold Aug 04, 2025

  260 Airport Dr S, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 918 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $899/SF
  • 157 Days On Market

  Current Estimated Value $835,219

  Last Listing Agent Francesca Santiago Keller Williams Realty Professionals (KW)

  260 Airport Dr S, Summerland Key, FL 33042
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  /44

  $650,000 Sold Apr 17, 2025

  268 Spanish Main Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Below List Price
  • $616/SF
  • 86 Days On Market

  Current Estimated Value $691,548

  Last Listing Agent Ally Kelley Ocean Sotheby's International Realty

  268 Spanish Main Dr, Summerland Key, FL 33042
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  /49

  $689,000 Sold Aug 29, 2025

  156 Pelican Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft
  • Built 1992

  Last Sold Summary

  • 4% Below List Price
  • $489/SF
  • 48 Days On Market

  Current Estimated Value $726,502

  Last Listing Agent Solaris Gregory Expert Realty LLC (HQ)

  156 Pelican Ln, Big Pine Key, FL 33043
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  /41

  $2,425,000 Sold Nov 21, 2025

  281 W Indies Dr, Summerland Key, FL 33042

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

  Last Sold Summary

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

  Current Estimated Value $2,430,933

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  281 W Indies Dr, Summerland Key, FL 33042
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  /82

  $1,800,000 Sold Jun 20, 2025

  17175 Allamanda Dr W, Summerland Key, FL 33042

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

  Last Sold Summary

  • 5% Below List Price
  • $851/SF
  • 19 Days On Market

  Current Estimated Value $1,833,430

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  17175 Allamanda Dr W, Summerland Key, FL 33042
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  /39

  $640,000 Sold Nov 18, 2025

  1341 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 1993

  Last Sold Summary

  • 15% Below List Price
  • $441/SF
  • 123 Days On Market

  Current Estimated Value $655,984

  Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

  1341 Avenue C, Big Pine Key, FL 33043
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  /46

  $760,000 Sold Apr 02, 2025

  31028 Hollerich Dr, Big Pine Key, FL 33043

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

  Last Sold Summary

  • 4% Below List Price
  • $792/SF
  • 5 Days On Market

  Current Estimated Value $886,565

  Last Listing Agent Vladimir Prokhodnoy Expert Realty LLC (HQ)

  31028 Hollerich Dr, Big Pine Key, FL 33043
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  /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 $1,241,349

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

  17144 Coral Dr, Summerland Key, FL 33042
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  /38

  $900,000 Sold May 30, 2025

  22971 Hawkins Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,142 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Below List Price
  • $788/SF
  • 46 Days On Market

  Current Estimated Value $915,491

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  22971 Hawkins Ln, Summerland Key, FL 33042
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  /2

  $280,000 Sold Apr 09, 2025

  31368 E Ave, Big Pine Key, FL 33043

  • Land

  Last Sold Summary

  • 14% Below List Price
  • 11 Days On Market

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.

  31368 E Ave, Big Pine Key, FL 33043
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  /46

  $699,000 Sold May 08, 2025

  25022 Palm Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2015

  Last Sold Summary

  • 4% Below List Price
  • $582/SF
  • 35 Days On Market

  Current Estimated Value $715,017

  Last Listing Agent Stephany Duvall Engel & Volkers Marathon

  25022 Palm Ln, Summerland Key, FL 33042
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  /48

  $780,000 Sold Nov 13, 2025

  3978 Gordon Rd, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Below List Price
  • $677/SF
  • 2 Days On Market

  Current Estimated Value $779,274

  Last Listing Agent Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

  3978 Gordon Rd, Big Pine Key, FL 33043
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  /66

  $910,000 Sold Jul 23, 2025

  246 Colson Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,541 Sq Ft
  • Built 1990

  Last Sold Summary

  • 43% Below List Price
  • $591/SF
  • 427 Days On Market

  Current Estimated Value $981,246

  Last Listing Agent Tracey Petrusha Venture Realty Group

  246 Colson Dr, Summerland Key, FL 33042
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  /39

  $1,150,000 Sold Nov 04, 2025

  29676 Ranger Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 1987

  Last Sold Summary

  • 8% Below List Price
  • $1,081/SF
  • 87 Days On Market

  Current Estimated Value $1,135,650

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

  29676 Ranger Ave, Big Pine Key, FL 33043
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  /33

  $665,000 Sold Aug 14, 2025

  21161 Old State Road 4a, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 855 Sq Ft
  • Built 1975

  Last Sold Summary

  • 5% Below List Price
  • $778/SF
  • 74 Days On Market

  Current Estimated Value $635,321

  Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

  21161 Old State Road 4a, Summerland Key, FL 33042
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  /2

  $55,000 Sold Jan 16, 2026

  0 State Rd Unit 4A, Little Torch Key, FL 33042

  • Land
  • 0.26 Acre
  • $213,187 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 35 Days On Market

  Last Listing Agent Nate Meyer Meyer and Boumerhi Realty LLC

  0 State Rd Unit 4A, Little Torch Key, FL 33042
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  /26

  $730,000 Sold Nov 28, 2025

  23930 Overseas Hwy, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,360 Sq Ft
  • Built 1946

  Last Sold Summary

  • 9% Below List Price
  • $537/SF
  • 137 Days On Market

  Current Estimated Value $749,309

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  23930 Overseas Hwy, Summerland Key, FL 33042
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  /34

  $578,000 Sold Jun 23, 2025

  31142 Avenue I, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Below List Price
  • $602/SF
  • 12 Days On Market

  Current Estimated Value $596,883

  Last Listing Agent Jimmy Lane Island Life Realty Experts

  31142 Avenue I, Big Pine Key, FL 33043
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  /49

  $864,000 Sold Jan 20, 2026

  3987 Gordon Rd, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1989

  Last Sold Summary

  • 1% Below List Price
  • $857/SF
  • 24 Days On Market

  Current Estimated Value $855,541

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

  3987 Gordon Rd, Big Pine Key, FL 33043
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  /22

  $650,000 Sold Aug 19, 2025

  27384 Saint Lucie Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 888 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Below List Price
  • $732/SF
  • 28 Days On Market

  Current Estimated Value $677,012

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  27384 Saint Lucie Ln, Summerland Key, FL 33042
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  /23

  $510,000 Sold Jul 30, 2025

  27390 Barbados Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1982

  Last Sold Summary

  • 27% Below List Price
  • $455/SF
  • 176 Days On Market

  Current Estimated Value $617,923

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  27390 Barbados Ln, Summerland Key, FL 33042
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  /4

  $810,250 Sold Oct 20, 2025

  23745 Barbuda Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $614/SF
  • 0 Days On Market

  Current Estimated Value $843,337

  Last Listing Agent Nate Meyer Meyer and Boumerhi Realty LLC

  23745 Barbuda Ln, Summerland Key, FL 33042
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  /68

  $2,600,000 Sold May 30, 2025

  531 Seminole Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,604 Sq Ft
  • Built 1985

  Last Sold Summary

  • 13% Below List Price
  • $998/SF
  • 57 Days On Market

  Current Estimated Value $2,606,179

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  531 Seminole Dr, Summerland Key, FL 33042
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  /47

  $1,150,000 Sold Sep 04, 2025

  1021 Caribbean Dr E, Summerland Key, FL 33042

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

  Last Sold Summary

  • 8% Below List Price
  • $1,331/SF
  • 135 Days On Market

  Current Estimated Value $1,125,367

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1021 Caribbean Dr E, Summerland Key, FL 33042
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  /51

  $1,725,000 Sold Feb 06, 2026

  1082 Bay Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,440 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $1,198/SF
  • 5 Days On Market

  Current Estimated Value $1,850,819

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

  1082 Bay Dr, Summerland Key, FL 33042
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  /40

  $900,000 Sold Jul 01, 2025

  1342 Ocean Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft
  • Built 1983

  Last Sold Summary

  • 18% Below List Price
  • $907/SF
  • 137 Days On Market

  Current Estimated Value $935,388

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  1342 Ocean Dr, Summerland Key, FL 33042
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  /22

  $257,500 Sold Feb 17, 2026

  701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 2% Below List Price
  • 21 Days On Market

  Current Estimated Value $257,237

  Last Listing Agent Mary Bryant Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042

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