297

Recently Sold Homes in 33042

Section Image
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /29

    $435,000

    Sold Feb 23, 2026

    27997 Coral Shores Rd, Little Torch Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft
    • Built 1985

    Last Sold Summary

    • 13% Below List Price
    • $647/SF
    • 11 Days On Market

    Last Listing Agent Jamie Caudill Lokation Real Estate

    27997 Coral Shores Rd, Little Torch 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
  • /22

    $2,250,000

    Sold Sep 11, 2026

    17210 Angelfish Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2.5 Baths
    • 2,288 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $983/SF
    • 105 Days On Market

    Current Estimated Value $2,316,905

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

    17210 Angelfish Ln, Summerland Key, FL 33042
  • /18

    $570,000

    Sold May 28, 2026

    27970 Lobster Tail Trail, Little Torch Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,449 Sq Ft
    • Built 1980

    Last Sold Summary

    • 1% Below List Price
    • $393/SF
    • 3 Days On Market

    Last Listing Agent Miranda Dender Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    27970 Lobster Tail Trail, Little Torch Key, FL 33042
  • /30

    $355,000

    Sold Jul 01, 2026

    27960 Porgie Path, Little Torch Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 1,044 Sq Ft
    • Built 1986

    Last Sold Summary

    • $340/SF
    • 141 Days On Market

    Last Listing Agent Elaine Coyle Keller Williams Key West Compass Realty

    27960 Porgie Path, Little Torch 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 $1,231,100

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

    17144 Coral Dr, Summerland Key, FL 33042
  • /6

    $2,500,000

    Sold Jun 15, 2026

    653 Sawyer Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,714 Sq Ft
    • Built 1995

    Last Sold Summary

    • $1,459/SF

    Current Estimated Value $2,264,727

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

    653 Sawyer Dr, Summerland Key, FL 33042
  • /24

    $555,000

    Sold Mar 27, 2026

    219 Caribbean Dr E, Summerland Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1981

    Last Sold Summary

    • 31% Below List Price
    • $578/SF
    • 32 Days On Market

    Current Estimated Value $730,332

    Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

    219 Caribbean Dr E, Summerland Key, FL 33042
  • /33

    $965,000

    Sold Apr 08, 2026

    27417 Tobago Ln, Ramrod Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,494 Sq Ft
    • Built 2010

    Last Sold Summary

    • 20% Below List Price
    • $646/SF
    • 205 Days On Market

    Current Estimated Value $981,060

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    27417 Tobago Ln, Ramrod Key, FL 33042
  • /107

    $2,800,000

    Sold May 22, 2026

    747 La Fitte Rd, Summerland Key, FL 33042

    • 3 Beds
    • 3.5 Baths
    • 2,538 Sq Ft
    • Built 2024

    Last Sold Summary

    • 12% Below List Price
    • $1,103/SF
    • 223 Days On Market

    Current Estimated Value $2,752,947

    Last Listing Agent John L. Markle Keller Williams Realty Premier Properties - Kendall

    747 La Fitte Rd, Summerland Key, FL 33042
  • /43

    $849,000

    Sold May 13, 2026

    25057 7th St, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • Built 1987

    Last Sold Summary

    • 11% Below List Price
    • $404/SF
    • 85 Days On Market

    Current Estimated Value $867,550

    Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.

    25057 7th St, Summerland Key, FL 33042
  • /2

    $55,000

    Sold Jan 16, 2026

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

    • Land
    • 11,237 Sq Ft
    • $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
  • /26

    $730,000

    Sold Nov 28, 2025

    23930 Overseas Hwy, Summerland Key, FL 33042

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

    Last Sold Summary

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

    Current Estimated Value $776,074

    Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

    23930 Overseas Hwy, Summerland Key, FL 33042
  • /22

    $685,000

    Sold Aug 24, 2026

    4039 Egret Ln, Summerland Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $892/SF
    • 66 Days On Market

    Current Estimated Value $684,703

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    4039 Egret Ln, Summerland Key, FL 33042
  • /97

    $2,000,000

    Sold Jun 11, 2026

    680 Cruikshank Island, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 3,013 Sq Ft
    • Built 1987

    Last Sold Summary

    • 29% Below List Price
    • $664/SF
    • 214 Days On Market

    Current Estimated Value $2,014,441

    Last Listing Agent Barbara Crespo Keller Williams Key West Compass Realty

    680 Cruikshank Island, Summerland Key, 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 $695,833

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

    17230 Angelfish Ln, Sugarloaf Shores, FL 33042
  • /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 $915,309

    Last Listing Agent Nate Meyer Meyer and Boumerhi Realty LLC

    23745 Barbuda Ln, 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 $813,000

    Last Listing Agent Jessica Forsythe eXp Realty LLC Southernmost Branch

    19611 Tequesta St, Summerland Key, FL 33042
  • /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 $1,756,548

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

    1082 Bay Dr, Summerland Key, FL 33042
  • /22

    $257,500

    Sold Feb 17, 2026

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

    • Land
    • 2,078 Sq Ft
    • $5,397,834 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 21 Days On Market

    Current Estimated Value $264,274

    Last Listing Agent Mary Bryant Keller Williams Key West Compass Realty

    701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042
  • /55

    $2,220,000

    Sold Mar 30, 2026

    948 Gulf Dr, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 2,010 Sq Ft
    • Built 2000

    Last Sold Summary

    • 3% Below List Price
    • $1,104/SF
    • 111 Days On Market

    Current Estimated Value $2,231,245

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    948 Gulf Dr, Summerland Key, FL 33042
  • /43

    $975,000

    Sold Aug 26, 2026

    27426 Martinique Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1982

    Last Sold Summary

    • 11% Below List Price
    • $692/SF
    • 21 Days On Market

    Current Estimated Value $981,420

    Last Listing Agent Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    27426 Martinique Ln, Summerland Key, FL 33042
  • /7

    $4,325,000

    Sold May 28, 2026

    231 E Shore Dr Unit 3, Summerland Key, FL 33042

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

    Last Sold Summary

    • $1,387/SF
    • 237 Days On Market

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

    231 E Shore Dr Unit 3, 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 $1,009,381

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    146 Sugarloaf Dr, Summerland Key, FL 33042

Showing Results 241 - 280, Page 7 of 8

How to Buy a Home How to Finance a Home How to Sell a Home