368

Recently Sold Summerland Key, FL Homes

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  • /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
  • /58

    $625,000

    Sold Aug 10, 2026

    31147 Avenue H, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1996

    Last Sold Summary

    • 11% Below List Price
    • $651/SF
    • 96 Days On Market

    Current Estimated Value $638,341

    Last Listing Agent Jamie Caudill Lokation Real Estate

    31147 Avenue H, Big Pine Key, FL 33043
  • /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
  • /32

    $3,500

    Sold May 20, 2026

    29850 Journeys End Rd, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1988

    Last Sold Summary

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

    Current Estimated Value $1,289,717

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    29850 Journeys End Rd, Big Pine Key, FL 33043
  • /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
  • /40

    $790,000

    Sold Jul 02, 2026

    3686 Gulfstream St, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,292 Sq Ft
    • Built 1989

    Last Sold Summary

    • 2% Below List Price
    • $611/SF
    • 56 Days On Market

    Current Estimated Value $793,822

    Last Listing Agent Gidget Jackson RE/MAX Realty Group

    3686 Gulfstream St, Big Pine Key, FL 33043
  • /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
  • /38

    $840,000

    Sold Sep 30, 2025

    3611 S Seas St, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,068 Sq Ft
    • Built 1990

    Last Sold Summary

    • 3% Below List Price
    • $787/SF
    • 183 Days On Market

    Last Listing Agent Scott Brisson KeyIsle Realty

    3611 S Seas St, Big Pine Key, FL 33043
  • /43

    $1,100,000

    Sold May 14, 2026

    1011 Caribbean Dr E, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft
    • Built 1997

    Last Sold Summary

    • 8% Below List Price
    • $962/SF
    • 0 Days On Market

    Current Estimated Value $1,116,759

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    1011 Caribbean Dr E, Summerland Key, FL 33042
  • /42

    $1,449,000

    Sold Sep 01, 2026

    22872 Buccaneer Ln, Cudjoe Key, FL 33042

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

    Last Sold Summary

    • $966/SF
    • 22 Days On Market

    Current Estimated Value $1,143,910

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    22872 Buccaneer Ln, Cudjoe Key, FL 33042
  • /70

    $1,290,000

    Sold May 19, 2026

    403 Indies Rd, Ramrod Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1991

    Last Sold Summary

    • 4% Below List Price
    • $960/SF
    • 63 Days On Market

    Current Estimated Value $1,288,115

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    403 Indies Rd, Ramrod Key, FL 33042
  • /50

    $1,900,000

    Sold Mar 27, 2026

    711 W Indies Dr, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,000 Sq Ft
    • Built 2025

    Last Sold Summary

    • 5% Below List Price
    • $950/SF
    • 62 Days On Market

    Current Estimated Value $1,723,933

    Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

    711 W Indies Dr, Summerland Key, FL 33042
  • /26

    $610,000

    Sold Apr 03, 2026

    29030 Iris Dr, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,353 Sq Ft
    • Built 1974

    Last Sold Summary

    • 15% Below List Price
    • $451/SF
    • 449 Days On Market

    Current Estimated Value $626,789

    Last Listing Agent Justyn Ewald Expert Realty LLC (HQ)

    29030 Iris Dr, Big Pine Key, FL 33043
  • /41

    $1,105,000

    Sold Sep 26, 2025

    22946 Bluegill Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1975

    Last Sold Summary

    • 14% Below List Price
    • $921/SF
    • 255 Days On Market

    Current Estimated Value $1,157,108

    Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt RE Co.

    22946 Bluegill Ln, Summerland Key, FL 33042
  • /46

    $1,599,000

    Sold Jul 28, 2026

    2237 San Remo Dr, Big Pine Key, FL 33043

    • 2 Beds
    • 3 Baths
    • 1,244 Sq Ft
    • Built 1994

    Last Sold Summary

    • $1,285/SF
    • 27 Days On Market

    Current Estimated Value $1,571,872

    Last Listing Agent Suzanne Moore Suzanne Moore Real Estate

    2237 San Remo Dr, Big Pine Key, FL 33043
  • /47

    $1,075,000

    Sold May 13, 2026

    110 Doubloon Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Below List Price
    • $853/SF
    • 9 Days On Market

    Current Estimated Value $1,071,736

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    110 Doubloon Ln, Summerland Key, FL 33042
  • 22963 Anne Bonny Ln, Summerland Key, FL 33042

    $560,000

    Sold Jun 18, 2026

    22963 Anne Bonny Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 834 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $671/SF
    • 43 Days On Market

    Current Estimated Value $572,321

    Last Listing Agent Judith Exposito Luxe Properties

    22963 Anne Bonny Ln, Summerland Key, FL 33042
  • /61

    $1,750,000

    Sold Mar 09, 2026

    876 Gulf Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,172 Sq Ft
    • Built 1978

    Last Sold Summary

    • 20% Below List Price
    • $1,493/SF
    • 122 Days On Market

    Current Estimated Value $1,748,154

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

    876 Gulf Dr, Summerland Key, FL 33042
  • /97

    $1,090,000

    Sold Sep 01, 2026

    17151 Marlin Dr, Sugarloaf Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $716/SF
    • 32 Days On Market

    Current Estimated Value $1,210,142

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17151 Marlin Dr, Sugarloaf Key, FL 33042
  • /17

    $190,000

    Sold Apr 29, 2026

    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 300 Sq Ft
    • Built 2018

    Last Sold Summary

    • 14% Below List Price
    • $633/SF
    • 66 Days On Market

    Current Estimated Value $192,055

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

    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
  • /34

    $840,207

    Sold Jul 03, 2026

    131 Doubloon Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1999

    Last Sold Summary

    • 14% Below List Price
    • $577/SF
    • 61 Days On Market

    Current Estimated Value $877,890

    Last Listing Agent Jenifer Hirsch Bluescape Real Estate

    131 Doubloon Ln, Summerland Key, FL 33042
  • /37

    $615,000

    Sold Aug 31, 2026

    27732 Astrangia Ave, Little Torch Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • $563/SF
    • 38 Days On Market

    Last Listing Agent Monika Rydzak eXp Realty LLC KW Branch

    27732 Astrangia Ave, Little Torch Key, FL 33042
  • /5

    $75,000

    Sold Jun 22, 2026

    Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

    • Land
    • 14,810 Sq Ft
    • $220,588 per Acre

    Last Sold Summary

    • 46% Below List Price
    • 177 Days On Market

    Last Listing Agent Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

    Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
  • /64

    $809,000

    Sold Nov 12, 2025

    3714 Pine St, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1989

    Last Sold Summary

    • 17% Below List Price
    • $722/SF
    • 194 Days On Market

    Current Estimated Value $830,185

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    3714 Pine St, Big Pine Key, FL 33043
  • /91

    $3,675,000

    Sold May 11, 2026

    493 Coral Ave, Ramrod Key, FL 33042

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Below List Price
    • $2,127/SF
    • 10 Days On Market

    Current Estimated Value $3,604,401

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    493 Coral Ave, Ramrod Key, FL 33042
  • /8

    $340,000

    Sold Dec 11, 2025

    0 Overseas Hwy, Summerland Key, FL 33042

    • Land
    • 12,500 Sq Ft
    • $1,184,832 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 328 Days On Market

    Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

    0 Overseas Hwy, Summerland Key, FL 33042
  • /52

    $1,530,000

    Sold Jan 16, 2026

    1370 Long Beach Dr, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,181 Sq Ft
    • Built 2011

    Last Sold Summary

    • 4% Below List Price
    • $1,296/SF
    • 33 Days On Market

    Current Estimated Value $1,539,138

    Last Listing Agent Coby Taylor Expert Realty LLC (HQ)

    1370 Long Beach Dr, Big Pine Key, FL 33043
  • /74

    $2,450,000

    Sold Aug 17, 2026

    17385 Keystone Rd, Summerland Key, FL 33042

    • 4 Beds
    • 4 Baths
    • 1,804 Sq Ft
    • Built 1985

    Last Sold Summary

    • 25% Below List Price
    • $1,358/SF
    • 168 Days On Market

    Current Estimated Value $2,797,731

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

    17385 Keystone Rd, Summerland Key, FL 33042
  • /32

    $575,000

    Sold Jul 07, 2026

    29961 Pine Channel Rd, Big Pine Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Built 1975

    Last Sold Summary

    • 8% Below List Price
    • $676/SF
    • 100 Days On Market

    Current Estimated Value $576,644

    Last Listing Agent Terrance Sullivan Saltwater Real Estate Florida Keys, Inc

    29961 Pine Channel Rd, Big Pine Key, FL 33043
  • /21

    $775,000

    Sold Mar 23, 2026

    27360 Saint Croix Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1983

    Last Sold Summary

    • 16% Below List Price
    • $673/SF
    • 272 Days On Market

    Current Estimated Value $799,287

    Last Listing Agent Terry Bush Bluescape Real Estate

    27360 Saint Croix Ln, Summerland Key, FL 33042
  • /14

    $205,000

    Sold May 20, 2026

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042

    • Land
    • 1,742 Sq Ft
    • $5,125,000 per Acre

    Last Sold Summary

    • 21% Below List Price
    • 56 Days On Market

    Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
  • /43

    $1,700,000

    Sold Jan 30, 2026

    22562 Jolly Roger Dr, Summerland Key, FL 33042

    • 4 Beds
    • 2 Baths
    • 2,074 Sq Ft
    • Built 1987

    Last Sold Summary

    • 12% Below List Price
    • $820/SF
    • 140 Days On Market

    Current Estimated Value $1,694,538

    Last Listing Agent Krystal Thomas eXp Realty LLC

    22562 Jolly Roger Dr, Summerland Key, FL 33042
  • /156

    $1,400,000

    Sold Jul 23, 2026

    142 Peg Leg Ln, Cudjoe Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,136 Sq Ft
    • Built 2024

    Last Sold Summary

    • 12% Below List Price
    • $655/SF
    • 324 Days On Market

    Current Estimated Value $1,467,506

    Last Listing Agent Jose Cabrera AmeriFirst Realty

    142 Peg Leg Ln, Cudjoe Key, FL 33042
  • /44

    $700,000

    Sold Jan 09, 2026

    701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 2000

    Last Sold Summary

    • 10% Below List Price
    • $810/SF
    • 23 Days On Market

    Last Listing Agent Holly Burger RE/MAX Keys Connection (KW)

    701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
  • /2

    $813,000

    Sold Sep 01, 2026

    29115 Rose Dr, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Built 2000

    Last Sold Summary

    • 3% Below List Price
    • $650/SF
    • 57 Days On Market

    Current Estimated Value $819,054

    Last Listing Agent Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

    29115 Rose Dr, Big Pine Key, FL 33043
  • /57

    $1,250,000

    Sold Jun 30, 2026

    25368 2nd St, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Built 1958

    Last Sold Summary

    • 24% Below List Price
    • $898/SF
    • 241 Days On Market

    Current Estimated Value $1,239,000

    Last Listing Agent Ally Kelley Ocean Sotheby's International

    25368 2nd St, Summerland Key, FL 33042

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