297

Recently Sold Homes in 33042

Section Image
  • /62

    $1,500,000

    Sold Aug 10, 2026

    22410 Jolly Roger Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,587 Sq Ft
    • Built 1982

    Last Sold Summary

    • $945/SF
    • 10 Days On Market

    Current Estimated Value $1,674,544

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    22410 Jolly Roger Dr, Summerland Key, FL 33042
  • /41

    $1,065,000

    Sold Jun 26, 2026

    325 Pirates Rd, Summerland Key, FL 33042

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

    Last Sold Summary

    • 9% Below List Price
    • $807/SF
    • 148 Days On Market

    Current Estimated Value $1,076,103

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    325 Pirates Rd, 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 $966,101

    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 $1,103,268

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

    22521 Jolly Roger Dr, Cudjoe 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 $929,773

    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 $1,578,659

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    28538 John Silver Rd, Summerland Key, FL 33042
  • /32

    $950,000

    Sold Aug 13, 2026

    1129 Hawksbill Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,150 Sq Ft
    • Built 1984

    Last Sold Summary

    • 1% Below List Price
    • $826/SF
    • 3 Days On Market

    Current Estimated Value $964,524

    Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

    1129 Hawksbill Ln, Summerland Key, FL 33042
  • /35

    $495,000

    Sold Sep 17, 2026

    27967 Coral Shores Rd, Little Torch Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,184 Sq Ft
    • Built 1980

    Last Sold Summary

    • 8% Below List Price
    • $418/SF
    • 84 Days On Market

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    27967 Coral Shores Rd, Little Torch 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 $670,720

    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 $736,539

    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 $271,779

    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 $934,544

    Last Listing Agent Mark Gable Engel & Völkers 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 $1,917,952

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

    1058 Buttonwood Dr E, 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 $1,380,500

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    570 Blackbeard Rd, Summerland Key, FL 33042
  • /125

    $5,000,000

    Sold Jun 18, 2026

    24200 Overseas Hwy, Summerland Key, FL 33042

    • 5 Beds
    • 5.5 Baths
    • 3,000 Sq Ft
    • Built 1977

    Last Sold Summary

    • 19% Below List Price
    • $1,667/SF
    • 106 Days On Market

    Current Estimated Value $5,010,172

    Last Listing Agent Sylvia Werling Keller Williams Key West Compass Realty

    24200 Overseas Hwy, Summerland Key, FL 33042
  • /47

    $1,075,000

    Sold Aug 28, 2026

    401 Coral Ave, Ramrod Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 2016

    Last Sold Summary

    • 6% Below List Price
    • $899/SF

    Current Estimated Value $1,130,028

    Last Listing Agent Coby Taylor Expert Realty LLC (HQ)

    401 Coral Ave, Ramrod Key, FL 33042
  • /46

    $2,000,000

    Sold Jul 14, 2026

    1330 Sugarloaf Blvd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft
    • Built 1979

    Last Sold Summary

    • 9% Below List Price
    • $1,232/SF
    • 62 Days On Market

    Current Estimated Value $1,986,572

    Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

    1330 Sugarloaf Blvd, 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
  • /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 $2,255,015

    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 $773,048

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    27138 Dolphin Rd, 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 $777,752

    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 $3,117,582

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    270 E Caribbean Dr, Summerland Key, FL 33042
  • /72

    $2,100,000

    Sold Aug 24, 2026

    27356 Dominica Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 2007

    Last Sold Summary

    • 5% Below List Price
    • $1,389/SF
    • 4 Days On Market

    Current Estimated Value $1,908,615

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

    27356 Dominica Ln, 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 $5,365,305

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

    1151 Ocean Dr, 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 $49,500

    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
  • /38

    $850,000

    Sold Sep 15, 2026

    437 Pirates Rd, Little Torch Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 2015

    Last Sold Summary

    • 5% Below List Price
    • $656/SF
    • 78 Days On Market

    Current Estimated Value $893,261

    Last Listing Agent Jo Ann Cook Ocean Sotheby's International

    437 Pirates Rd, 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 $889,371

    Last Listing Agent Jimmy Lane Island Life Realty Experts

    554 W Shore 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 $214,387

    Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
  • 13 Yuca Ln, Torch Key, FL 33042

    $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
  • /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 $322,422

    Last Listing Agent Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 181, Cudjoe 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 $757,131

    Last Listing Agent Brent Bishop Internet Realty of the Florida Keys

    27235 Mariposa Rd, Summerland Key, FL 33042
  • /6

    $1,540,750

    Sold Sep 10, 2026

    559 Powell Ave, Little Torch Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 2019

    Last Sold Summary

    • 8% Below List Price
    • $1,288/SF
    • 115 Days On Market

    Current Estimated Value $1,425,417

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

    559 Powell Ave, Little Torch 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 $841,657

    Last Listing Agent Pamela Stangler Expert Realty LLC

    22878 Privateer Dr, 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 Prudential Keyswide Properties

    0 Asturias Rd, Cudjoe Key, FL 33042
  • /42

    $1,065,000

    Sold Jun 22, 2026

    27345 Barbuda Ln, Summerland Key, FL 33042

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

    Last Sold Summary

    • 3% Below List Price
    • $807/SF
    • 18 Days On Market

    Last Listing Agent Madeleine Young Island Welcome Real Estate LLC

    27345 Barbuda Ln, Summerland Key, FL 33042
  • /2

    $49,000

    Sold Oct 03, 2025

    Lot 24 Rainbow Beach, Big Torch Key, FL 33042

    • Land
    • 5,499 Sq Ft
    • $388,080 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 50 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot 24 Rainbow Beach, Big Torch Key, FL 33042
  • /61

    $2,675,000

    Sold Jun 01, 2026

    20844 4th Ave W, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,951 Sq Ft
    • Built 1997

    Last Sold Summary

    • 4% Below List Price
    • $906/SF
    • 10 Days On Market

    Current Estimated Value $2,678,878

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

    20844 4th Ave W, Summerland Key, FL 33042

Showing Results 1 - 40, Page 1 of 8

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