370

Recently Sold Summerland Key, FL Homes

Section Image
  • /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 $1,075,879

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    325 Pirates Rd, Summerland Key, FL 33042
  • /50

    $1,632,000

    Sold Apr 30, 2026

    29678 Constitution Ave, Big Pine Key, FL 33043

    • 3 Beds
    • 2.5 Baths
    • 2,172 Sq Ft
    • Built 1972

    Last Sold Summary

    • 5% Below List Price
    • $751/SF
    • 62 Days On Market

    Current Estimated Value $1,635,619

    Last Listing Agent Callie Harris Brenda Donnelly Real Estate LLC

    29678 Constitution Ave, Big Pine Key, FL 33043
  • /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 $942,462

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

    76 W Shore Dr, 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 $920,617

    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 $1,532,219

    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 $656,089

    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 $724,124

    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 $269,729

    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 $930,560

    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 $1,906,466

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

    1058 Buttonwood Dr E, Summerland Key, FL 33042
  • /2

    $510,000

    Sold Sep 08, 2025

    Unlisted Address

    • 3 Beds
    • 2 Baths
    • 972 Sq Ft
    • Built 1989

    Last Sold Summary

    • $525/SF

    Current Estimated Value $528,837

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    Unlisted Address
  • /3

    $510,000

    Sold Jun 18, 2026

    57 Pelican Ln, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 948 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $538/SF
    • 23 Days On Market

    Current Estimated Value $545,931

    Last Listing Agent Elsa Machado Elsa Realty, LLC

    57 Pelican Ln, Big Pine Key, FL 33043
  • /65

    $4,000

    Sold Jul 06, 2026

    30361 Hardin Rd, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 888 Sq Ft
    • Built 1963

    Last Sold Summary

    • 20% Below List Price
    • $5/SF
    • 79 Days On Market

    Current Estimated Value $942,308

    Last Listing Agent Maris Delgado LoKation Real Estate - Key Largo

    30361 Hardin Rd, Big Pine Key, FL 33043
  • /58

    $572,000

    Sold May 27, 2026

    175 E Cahill Ct, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1991

    Last Sold Summary

    • 5% Below List Price
    • $567/SF
    • 40 Days On Market

    Current Estimated Value $569,942

    Last Listing Agent Darlene Alferes Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    175 E Cahill Ct, Big Pine Key, FL 33043
  • /38

    $790,000

    Sold May 22, 2026

    30471 Coconut Hwy, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,513 Sq Ft
    • Built 1959

    Last Sold Summary

    • 14% Below List Price
    • $522/SF
    • 319 Days On Market

    Current Estimated Value $773,879

    Last Listing Agent Richard Haskins Buy The Keys

    30471 Coconut Hwy, Big Pine Key, FL 33043
  • /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 $1,138,333

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    570 Blackbeard Rd, Summerland Key, FL 33042
  • /61

    $592,000

    Sold May 29, 2026

    29951 Pine Channel Rd, Big Pine Key, FL 33043

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

    Last Sold Summary

    • 9% Below List Price
    • $649/SF
    • 80 Days On Market

    Current Estimated Value $589,549

    Last Listing Agent Lindsay Ryan EXP Realty LLC

    29951 Pine Channel Rd, Big Pine Key, FL 33043
  • /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 $4,618,358

    Last Listing Agent Sylvia Werling Keller Williams Key West Compass Realty

    24200 Overseas Hwy, Summerland 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 $2,152,594

    Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

    1330 Sugarloaf Blvd, 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 $703,608

    Last Listing Agent Diana Fiddes Coldwell Banker Schmitt Key Largo

    27317 Cayman Ln, Summerland 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 $1,378,552

    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 $2,256,263

    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 $751,332

    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 $774,846

    Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

    22939 Privateer Dr, Summerland Key, FL 33042
  • /36

    $1,120,000

    Sold Mar 24, 2026

    2148 Bahia Shores Rd, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $933/SF
    • 1 Day On Market

    Current Estimated Value $1,127,151

    Last Listing Agent Anne Press Lokation Real Estate

    2148 Bahia Shores Rd, Big Pine Key, FL 33043
  • /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 $3,070,667

    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 $5,200,087

    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 $627,743

    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 $50,000

    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 $916,582

    Last Listing Agent Jimmy Lane Island Life Realty Experts

    554 W Shore Dr, Summerland Key, FL 33042
  • /66

    $1,715,000

    Sold Jul 31, 2026

    30985 Watson Blvd, Big Pine Key, FL 33043

    • 4 Beds
    • 3.5 Baths
    • 2,639 Sq Ft
    • Built 2022

    Last Sold Summary

    • $650/SF
    • 0 Days On Market

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    30985 Watson Blvd, Big Pine Key, FL 33043
  • /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 $3,342,758

    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 $208,609

    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 $1,184,520

    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 $318,560

    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 $749,551

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    27312 Anguila Ln, Summerland Key, FL 33042

Showing Results 1 - 40, Page 1 of 10

Frequently Asked Questions

What is the average home price in Summerland Key, FL?
Homes for sale in Summerland Key, FL have an average home price of $1,750,319.
What is the average time to sell a house in Summerland Key, FL?
The houses for sale in Summerland Key, FL spend an average of 113 days on the market.
What is the number of active homes for sale in Summerland Key, FL?
There are 44 active homes for sale in Summerland Key, FL.
How many homes have sold over the last 12 months in Summerland Key, FL?
112 homes have sold in Summerland Key, FL over the last 12 months.

Home Price Trends

Median Sale Price
$1,102,500
Median Single Family Sale Price
$1,185,000
Median Townhouse Sale Price
$1,750,000
Median 2 Bedroom Sale Price
$1,000,000
Median 1 Bedroom Sale Price
$689,000
Average Price Per Sq Ft
$913
Number of Homes for Sale
44
Last 12 months Home Sales
112
Months of Supply
4.70
Median List Price
$1,290,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
5%
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