279

Recently Sold Homes in 33042

Section Image
  • /27

    $837,000

    Sold Jul 11, 2025

    27417 Cayman Ln, Summerland Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 1,085 Sq Ft
    • Built 1975

    Last Sold Summary

    • 14% Below List Price
    • $771/SF
    • 274 Days On Market

    Current Estimated Value $878,121

    Last Listing Agent Karen Quist Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    27417 Cayman Ln, Summerland Key, FL 33042
  • /60

    $950,000

    Sold Oct 17, 2025

    76 W Shore Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,028 Sq Ft
    • Built 2001

    Last Sold Summary

    • 13% Below List Price
    • $924/SF
    • 369 Days On Market

    Current Estimated Value $945,746

    Last Listing Agent Cardenas & Krug Team Coastal Collection Real Estate Inc.

    76 W Shore Dr, Summerland Key, FL 33042
  • /2

    $1,030,000

    Sold Nov 19, 2025

    22521 Jolly Roger Dr, Cudjoe Key, FL 33042

    • 4 Beds
    • 2.5 Baths
    • 1,728 Sq Ft
    • Built 2010

    Last Sold Summary

    • $596/SF
    • 0 Days On Market

    Current Estimated Value $1,108,949

    Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

    22521 Jolly Roger Dr, Cudjoe Key, FL 33042
  • /56

    $1,725,000

    Sold Jul 11, 2025

    17159 Amberjack Ln, Summerland Key, FL 33042

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

    Last Sold Summary

    • 14% Below List Price
    • $1,039/SF
    • 258 Days On Market

    Current Estimated Value $1,733,649

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

    17159 Amberjack Ln, Summerland Key, FL 33042
  • /33

    $910,000

    Sold Apr 13, 2026

    151 Cutthroat Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2.5 Baths
    • 1,140 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Below List Price
    • $798/SF
    • 46 Days On Market

    Current Estimated Value $915,727

    Last Listing Agent Heather Bennett Florida Keys Real Estate Co. (KW)

    151 Cutthroat Dr, Summerland Key, FL 33042
  • /45

    $1,550,000

    Sold Jan 30, 2026

    28538 John Silver Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $1,242/SF
    • 164 Days On Market

    Current Estimated Value $1,521,588

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    28538 John Silver Rd, Summerland Key, FL 33042
  • /45

    $630,000

    Sold Dec 08, 2025

    22970 Sharp Ln, Summerland Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 576 Sq Ft
    • Built 1985

    Last Sold Summary

    • 10% Below List Price
    • $1,094/SF
    • 4 Days On Market

    Current Estimated Value $664,476

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    22970 Sharp Ln, Summerland Key, FL 33042
  • /88

    $732,000

    Sold Apr 21, 2026

    40 Munson Ave, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 1998

    Last Sold Summary

    • 2% Below List Price
    • $693/SF
    • 128 Days On Market

    Current Estimated Value $739,364

    Last Listing Agent Lindsay Ryan EXP Realty LLC

    40 Munson Ave, Summerland Key, FL 33042
  • /37

    $268,000

    Sold Apr 27, 2026

    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042

    • Land
    • 2,178 Sq Ft
    • $5,360,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 52 Days On Market

    Current Estimated Value $285,512

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
  • /60

    $930,000

    Sold Jan 23, 2026

    27405 Guadaloupe Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 2008

    Last Sold Summary

    • 2% Below List Price
    • $722/SF
    • 51 Days On Market

    Current Estimated Value $938,861

    Last Listing Agent Mark Gable Engel & Volkers Marathon

    27405 Guadaloupe Ln, Summerland Key, FL 33042
  • /6

    $1,937,500

    Sold Jun 05, 2026

    1058 Buttonwood Dr E, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,767 Sq Ft
    • Built 2001

    Last Sold Summary

    • $1,096/SF
    • 0 Days On Market

    Current Estimated Value $1,592,238

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

    1058 Buttonwood Dr E, Summerland Key, FL 33042
  • /73

    $2,925,000

    Sold Jun 10, 2025

    17018 Wahoo Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft
    • Built 1991

    Last Sold Summary

    • 25% Below List Price
    • $1,987/SF
    • 122 Days On Market

    Current Estimated Value $3,040,513

    Last Listing Agent Coby Taylor Expert Realty LLC (HQ)

    17018 Wahoo Ln, Summerland Key, FL 33042
  • /16

    $1,400,000

    Sold Mar 16, 2026

    570 Blackbeard Rd, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 1,500 Sq Ft
    • Built 2026

    Last Sold Summary

    • 3% Below List Price
    • $933/SF
    • 14 Days On Market

    Current Estimated Value $1,397,000

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    570 Blackbeard Rd, Summerland Key, FL 33042
  • /49

    $650,000

    Sold Aug 20, 2025

    27317 Cayman Ln, Summerland Key, FL 33042

    • 2 Beds
    • 1.5 Baths
    • 1,029 Sq Ft
    • Built 2012

    Last Sold Summary

    • 28% Below List Price
    • $632/SF
    • 262 Days On Market

    Current Estimated Value $709,465

    Last Listing Agent Diana Fiddes Coldwell Banker Schmitt Key Largo

    27317 Cayman Ln, Summerland Key, FL 33042
  • /5

    $725,000

    Sold Jul 30, 2025

    19462 Canal Dr, Summerland Key, FL 33042

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

    Last Sold Summary

    • 6% Below List Price
    • $520/SF
    • 3 Days On Market

    Current Estimated Value $748,620

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

    19462 Canal Dr, Summerland Key, FL 33042
  • /27

    $300,000

    Sold Nov 26, 2025

    27983 Snapper Ln, Little Torch Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft
    • Built 1987

    Last Sold Summary

    • 9% Below List Price
    • $446/SF
    • 60 Days On Market

    Last Listing Agent Sandra Dolowy KeyIsle Realty

    27983 Snapper Ln, Little Torch Key, FL 33042
  • /2

    $55,000

    Sold Oct 22, 2025

    Lot 2 Rainbow Beach, Big Torch Key, FL 33042

    • Land
    • 5,000 Sq Ft
    • $479,160 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 2 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot 2 Rainbow Beach, Big Torch Key, FL 33042
  • /49

    $280,000

    Sold Jun 03, 2026

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft
    • Built 1976

    Last Sold Summary

    • $406/SF
    • 98 Days On Market

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
  • /46

    $1,390,000

    Sold Aug 26, 2025

    229 Caribbean Dr E, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Below List Price
    • $1,207/SF
    • 30 Days On Market

    Current Estimated Value $1,397,387

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

    229 Caribbean Dr E, Summerland Key, FL 33042
  • /68

    $2,250,000

    Sold Apr 03, 2026

    24266 Caribbean Dr W, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,055 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $1,095/SF
    • 14 Days On Market

    Current Estimated Value $2,231,985

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    24266 Caribbean Dr W, Summerland Key, FL 33042
  • /29

    $740,000

    Sold Oct 31, 2025

    27138 Dolphin Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Built 2022

    Last Sold Summary

    • 14% Below List Price
    • $561/SF
    • 181 Days On Market

    Current Estimated Value $759,458

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    27138 Dolphin Rd, Summerland Key, FL 33042
  • /47

    $1,100,000

    Sold Jun 27, 2025

    21014 7th Ave, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,361 Sq Ft
    • Built 1988

    Last Sold Summary

    • 19% Below List Price
    • $808/SF
    • 102 Days On Market

    Current Estimated Value $1,146,300

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    21014 7th Ave, Summerland Key, FL 33042
  • /7

    $4,275,000

    Sold Mar 04, 2026

    231 E Shore Dr Unit 7, Summerland Key, FL 33042

    • 5 Beds
    • 5.5 Baths
    • 3,119 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $1,371/SF
    • 114 Days On Market

    Last Listing Agent Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

    231 E Shore Dr Unit 7, Summerland Key, FL 33042
  • /41

    $775,000

    Sold May 01, 2026

    22939 Privateer Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 1988

    Last Sold Summary

    • $602/SF
    • 3 Days On Market

    Current Estimated Value $769,267

    Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

    22939 Privateer Dr, Summerland Key, FL 33042
  • /67

    $3,150,000

    Sold Jun 09, 2026

    270 E Caribbean Dr, Summerland Key, FL 33042

    • 4 Beds
    • 4 Baths
    • 2,375 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Below List Price
    • $1,326/SF
    • 22 Days On Market

    Current Estimated Value $2,722,116

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    270 E Caribbean Dr, Summerland Key, FL 33042
  • /55

    $5,003,500

    Sold Jan 05, 2026

    1151 Ocean Dr, Summerland Key, FL 33042

    • 5 Beds
    • 6 Baths
    • 3,952 Sq Ft
    • Built 2007

    Last Sold Summary

    • 28% Below List Price
    • $1,266/SF
    • 47 Days On Market

    Current Estimated Value $5,708,488

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

    1151 Ocean Dr, Summerland Key, FL 33042
  • /34

    $600,000

    Sold Sep 22, 2025

    19557 Mayan St, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 989 Sq Ft
    • Built 1958

    Last Sold Summary

    • 5% Below List Price
    • $607/SF
    • 186 Days On Market

    Current Estimated Value $643,990

    Last Listing Agent Lola McKee eXp Realty LLC

    19557 Mayan St, Summerland Key, FL 33042
  • /2

    $48,000

    Sold Mar 13, 2026

    0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042

    • Land

    Last Sold Summary

    • 26% Below List Price
    • 250 Days On Market

    Current Estimated Value $999,000

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042
  • /64

    $815,422

    Sold Nov 06, 2025

    554 W Shore Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,407 Sq Ft
    • Built 1963

    Last Sold Summary

    • 9% Below List Price
    • $580/SF
    • 34 Days On Market

    Current Estimated Value $898,311

    Last Listing Agent Jimmy Lane Island Life Realty Experts

    554 W Shore Dr, Summerland Key, FL 33042
  • /42

    $1,900,000

    Sold Jun 29, 2025

    20867 5th Ave W, Cudjoe Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,702 Sq Ft
    • Built 2011

    Last Sold Summary

    • 5% Below List Price
    • $1,116/SF
    • 17 Days On Market

    Current Estimated Value $1,922,382

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    20867 5th Ave W, Cudjoe Key, FL 33042
  • /71

    $3,150,000

    Sold Aug 28, 2025

    225 Colson Dr, Summerland Key, FL 33042

    • 6 Beds
    • 6.5 Baths
    • 4,976 Sq Ft
    • Built 2010

    Last Sold Summary

    • 10% Below List Price
    • $633/SF
    • 118 Days On Market

    Current Estimated Value $3,360,263

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    225 Colson Dr, Summerland Key, FL 33042
  • /20

    $207,000

    Sold Apr 09, 2026

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

    • Land
    • 1,742 Sq Ft
    • $5,175,000 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 375 Days On Market

    Current Estimated Value $247,743

    Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
  • /24

    $50,000

    Sold May 07, 2026

    13 Yuca Ln, Torch Key, FL 33042

    • Land
    • 5,000 Sq Ft
    • $435,540 per Acre

    Last Sold Summary

    • 24 Days On Market

    Last Listing Agent Regine Mercier The Keyes Company

    13 Yuca Ln, Torch Key, FL 33042
  • /43

    $1,150,000

    Sold Sep 22, 2025

    1032 Caribbean Dr E, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Built 1990

    Last Sold Summary

    • 18% Below List Price
    • $833/SF
    • 175 Days On Market

    Current Estimated Value $1,187,553

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    1032 Caribbean Dr E, Summerland Key, FL 33042
  • /24

    $310,000

    Sold Apr 16, 2026

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

    • Land
    • 2,178 Sq Ft
    • $6,200,000 per Acre

    Last Sold Summary

    • 19% Below List Price
    • 118 Days On Market

    Current Estimated Value $317,747

    Last Listing Agent Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
  • /37

    $705,000

    Sold Aug 21, 2025

    27312 Anguila Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • Built 1989

    Last Sold Summary

    • 15% Below List Price
    • $614/SF
    • 127 Days On Market

    Current Estimated Value $758,576

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    27312 Anguila Ln, Summerland Key, FL 33042
  • /31

    $725,000

    Sold Jan 05, 2026

    27235 Mariposa Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,364 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Below List Price
    • $532/SF
    • 127 Days On Market

    Current Estimated Value $745,281

    Last Listing Agent Brent Bishop Internet Realty of the Florida Keys

    27235 Mariposa Rd, Summerland Key, FL 33042
  • /35

    $817,500

    Sold Dec 01, 2025

    22878 Privateer Dr, Summerland Key, FL 33042

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

    Last Sold Summary

    • 7% Below List Price
    • $862/SF
    • 133 Days On Market

    Current Estimated Value $825,324

    Last Listing Agent Pamela Stangler Expert Realty LLC

    22878 Privateer Dr, Summerland Key, FL 33042
  • /83

    $3,300,000

    Sold Jul 11, 2025

    16705 Tamarind Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 3,086 Sq Ft
    • Built 2015

    Last Sold Summary

    • 27% Below List Price
    • $1,069/SF
    • 299 Days On Market

    Current Estimated Value $3,306,557

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

    16705 Tamarind Rd, Summerland Key, FL 33042
  • /3

    $75,000

    Sold Oct 10, 2025

    0 Asturias Rd, Cudjoe Key, FL 33042

    • Land
    • 1.01 Acres
    • $74,124 per Acre

    Last Sold Summary

    • 62% Below List Price
    • 41 Days On Market

    Last Listing Agent Maryann Warren Coldwell Banker - Ft. Lauderdale

    0 Asturias Rd, Cudjoe Key, FL 33042

Showing Results 1 - 40, Page 1 of 7

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