Recently Sold Summerland Key, FL Homes

/34
$650,000 Sold Sep 10, 2025

558 E Shore Dr, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,392 Sq Ft
- Built 1994
Last Sold Summary
- 12% Below List Price
- $467/SF
- 22 Days On Market
Current Estimated Value $697,360

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

558 E Shore Dr, Summerland Key, FL 33042
/40
$1,075,000 Sold Jun 16, 2025

791 W Indies Dr, Summerland Key, FL 33042
- 4 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1982
Last Sold Summary
- 20% Below List Price
- $933/SF
- 191 Days On Market
Current Estimated Value $1,108,003

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

791 W Indies Dr, Summerland Key, FL 33042
/22
$360,500 Sold Feb 07, 2025

27954 Tarpon Terrace, Little Torch Key, FL 33042
- 2 Beds
- 1.5 Baths
- 735 Sq Ft
- Built 1985
Last Sold Summary
- 10% Below List Price
- $490/SF
- 96 Days On Market
Last Listing Agent Anne Press Lokation Real Estate

27954 Tarpon Terrace, Little Torch Key, FL 33042
/3
$75,000 Sold Dec 08, 2025

29141 Mango Ln, Big Pine Key, FL 33043
- Land
Last Sold Summary
- 42% Below List Price
- 14 Days On Market
Last Listing Agent David Kaufmann Century 21 Circle

29141 Mango Ln, Big Pine Key, FL 33043
/21
$1,000,000 Sold Aug 29, 2025

419 Blackbeard Rd, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,050 Sq Ft
- Built 1988
Last Sold Summary
- 17% Below List Price
- $952/SF
- 250 Days On Market
Current Estimated Value $1,013,657

Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

419 Blackbeard 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
Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

22852 John Silver Ln, Summerland Key, FL 33042
/45
$565,000 Sold Sep 29, 2025

2421 Pensacola Rd, Big Pine Key, FL 33043
- 3 Beds
- 1 Bath
- 1,055 Sq Ft
- Built 1988
Last Sold Summary
- 5% Below List Price
- $536/SF
- 101 Days On Market
Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

2421 Pensacola Rd, Big Pine Key, FL 33043
/61
$1,636,000 Sold Aug 19, 2025

227 La Fitte Rd, Summerland Key, FL 33042
- 2 Beds
- 3 Baths
- 1,260 Sq Ft
- Built 1982
Last Sold Summary
- 9% Below List Price
- $1,298/SF
- 6 Days On Market
Current Estimated Value $1,640,704

Last Listing Agent Jennifer Chaney Chaney Homes

227 La Fitte Rd, Summerland Key, FL 33042
/36
$925,050 Sold Apr 24, 2025

3666 S Seas St, Big Pine Key, FL 33043
- 2 Beds
- 2 Baths
- 1,519 Sq Ft
- Built 1988
Last Sold Summary
- 18% Below List Price
- $609/SF
- 89 Days On Market
Current Estimated Value $936,496

Last Listing Agent Scott Brisson KeyIsle Realty

3666 S Seas St, Big Pine Key, FL 33043
/31
$219,900 Sold Mar 01, 2025

29859 Overseas Hwy Unit 8, Big Pine Key, FL 33043
- 1 Bed
- 1 Bath
- 396 Sq Ft
- Built 2007
Last Sold Summary
- 17% Below List Price
- $555/SF
- 254 Days On Market
Last Listing Agent Kathleen Gomez Coldwell Banker Schmitt RE Co.

29859 Overseas Hwy Unit 8, Big Pine Key, FL 33043
/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
Last Listing Agent Greg Gordon The Island Collective Realty

9 W, Cook Island Key, FL 33043
/13
$265,000 Sold Jun 30, 2025

31014 Avenue E, Big Pine Key, FL 33043
- Land
Last Sold Summary
- 29% Below List Price
- 103 Days On Market
Current Estimated Value $269,937

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

31014 Avenue E, Big Pine Key, FL 33043
/39
$1,116,000 Sold Jun 25, 2025

591 Blackbeard Rd, Summerland Key, FL 33042
- 4 Beds
- 5 Baths
- 2,512 Sq Ft
- Built 1989
Last Sold Summary
- 17% Below List Price
- $444/SF
- 25 Days On Market
Current Estimated Value $1,190,796

Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

591 Blackbeard Rd, Summerland Key, FL 33042
/46
$1,900,000 Sold Mar 27, 2025

271 W Indies Dr, Ramrod Key, FL 33042
- 4 Beds
- 4 Baths
- 2,358 Sq Ft
- Built 2023
Last Sold Summary
- 36% Below List Price
- $806/SF
- 342 Days On Market
Current Estimated Value $1,909,499

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

271 W Indies Dr, Ramrod Key, FL 33042
/2
$49,000 Sold Sep 22, 2025

Lot 23 Rainbow Beach, Big Torch Key, FL 33042
- Land
Last Sold Summary
- 21 Days On Market
Last Listing Agent Pamela Stangler Expert Realty LLC

Lot 23 Rainbow Beach, Big Torch Key, FL 33042
/40
$825,000 Sold Aug 04, 2025

260 Airport Dr S, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 918 Sq Ft
- Built 1959
Last Sold Summary
- 8% Below List Price
- $899/SF
- 157 Days On Market
Current Estimated Value $820,701

Last Listing Agent Francesca Santiago Keller Williams Realty Professionals (KW)

260 Airport Dr S, Summerland Key, FL 33042
/74
$3,300,000 Sold Feb 18, 2025

22572 Jolly Roger Dr, Summerland Key, FL 33042
- 6 Beds
- 4 Baths
- 3,225 Sq Ft
- Built 1963
Last Sold Summary
- 27% Below List Price
- $1,023/SF
- 313 Days On Market
Current Estimated Value $3,200,481

Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

22572 Jolly Roger Dr, Summerland Key, FL 33042
/44
$650,000 Sold Apr 17, 2025

268 Spanish Main Dr, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
- Built 1979
Last Sold Summary
- 7% Below List Price
- $616/SF
- 86 Days On Market
Current Estimated Value $666,448

Last Listing Agent Ally Kelley Ocean Sotheby's International

268 Spanish Main Dr, Summerland Key, FL 33042
/49
$689,000 Sold Aug 29, 2025

156 Pelican Ln, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 1,410 Sq Ft
- Built 1992
Last Sold Summary
- 4% Below List Price
- $489/SF
- 48 Days On Market
Current Estimated Value $696,859

Last Listing Agent Solaris Gregory Expert Realty LLC (HQ)

156 Pelican Ln, Big Pine Key, FL 33043
/41
$2,425,000 Sold Nov 21, 2025

281 W Indies Dr, Summerland Key, FL 33042
- 3 Beds
- 4 Baths
- 2,914 Sq Ft
- Built 2020
Last Sold Summary
- 12% Below List Price
- $832/SF
- 203 Days On Market
Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

281 W Indies Dr, Summerland Key, FL 33042
/31
$800,000 Sold Jan 31, 2025

22727 Jolly Roger Dr, Cudjoe Key, FL 33042
- 3 Beds
- 2 Baths
- 1,008 Sq Ft
- Built 2001
Last Sold Summary
- 8% Below List Price
- $794/SF
- 146 Days On Market
Current Estimated Value $803,690

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

22727 Jolly Roger Dr, Cudjoe Key, FL 33042
/35
$590,000 Sold Mar 28, 2025

2361 Pensacola Rd, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 1,184 Sq Ft
- Built 1984
Last Sold Summary
- 1% Below List Price
- $498/SF
- 54 Days On Market
Current Estimated Value $604,955

Last Listing Agent Nira Tocco Coldwell Banker Schmitt RE Co.

2361 Pensacola Rd, Big Pine Key, FL 33043
/82
$1,800,000 Sold Jun 20, 2025

17175 Allamanda Dr W, Summerland Key, FL 33042
- 4 Beds
- 3 Baths
- 2,116 Sq Ft
- Built 1999
Last Sold Summary
- 5% Below List Price
- $851/SF
- 19 Days On Market
Current Estimated Value $1,788,477

Last Listing Agent Lisa Swanson The Agency Florida Keys

17175 Allamanda Dr W, Summerland Key, FL 33042
/33
$725,000 Sold Feb 21, 2025

22918 Cudjoe Dr, Cudjoe Key, FL 33042
- 3 Beds
- 2 Baths
- 1,431 Sq Ft
- Built 2016
Last Sold Summary
- 9% Below List Price
- $507/SF
- 175 Days On Market
Current Estimated Value $774,250

Last Listing Agent Pamela Stangler Expert Realty LLC

22918 Cudjoe Dr, Cudjoe Key, FL 33042
/39
$640,000 Sold Nov 18, 2025

1341 Avenue C, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 1,452 Sq Ft
- Built 1993
Last Sold Summary
- 15% Below List Price
- $441/SF
- 123 Days On Market
Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

1341 Avenue C, Big Pine Key, FL 33043
/46
$760,000 Sold Apr 02, 2025

31028 Hollerich Dr, Big Pine Key, FL 33043
- 2 Beds
- 2 Baths
- 960 Sq Ft
- Built 1986
Last Sold Summary
- 4% Below List Price
- $792/SF
- 5 Days On Market
Current Estimated Value $740,439

Last Listing Agent Vladimir Prokhodnoy Expert Realty LLC (HQ)

31028 Hollerich Dr, Big Pine Key, FL 33043
/45
$1,230,000 Sold Jan 31, 2025

27379 Jamaica Ln, Ramrod Key, FL 33042
- 3 Beds
- 2 Baths
- 1,376 Sq Ft
- Built 2019
Last Sold Summary
- 2% Below List Price
- $894/SF
- 44 Days On Market
Current Estimated Value $1,188,032

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

27379 Jamaica Ln, Ramrod Key, FL 33042
/38
$900,000 Sold May 30, 2025

22971 Hawkins Ln, Summerland Key, FL 33042
- 3 Beds
- 3 Baths
- 1,142 Sq Ft
- Built 1987
Last Sold Summary
- 10% Below List Price
- $788/SF
- 46 Days On Market
Current Estimated Value $908,646

Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

22971 Hawkins Ln, Summerland Key, FL 33042
/2
$280,000 Sold Apr 09, 2025

31368 E Ave, Big Pine Key, FL 33043
- Land
Last Sold Summary
- 14% Below List Price
- 11 Days On Market
Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.

31368 E Ave, Big Pine Key, FL 33043
/14
$225,000 Sold Mar 07, 2025

701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
- Land
Last Sold Summary
- 12% Below List Price
- 246 Days On Market
Current Estimated Value $224,496

Last Listing Agent Mary Conklin Action Keys Realty of the Lower FL Keys LLC

701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
/46
$699,000 Sold May 08, 2025

25022 Palm Ln, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 2015
Last Sold Summary
- 4% Below List Price
- $582/SF
- 35 Days On Market
Current Estimated Value $713,000

Last Listing Agent Stephany Duvall Engel & Volkers Marathon

25022 Palm Ln, Summerland Key, FL 33042
/48
$780,000 Sold Nov 13, 2025

3978 Gordon Rd, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1978
Last Sold Summary
- 1% Below List Price
- $677/SF
- 2 Days On Market
Last Listing Agent Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

3978 Gordon Rd, Big Pine Key, FL 33043
/66
$910,000 Sold Jul 23, 2025

246 Colson Dr, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,541 Sq Ft
- Built 1990
Last Sold Summary
- 43% Below List Price
- $591/SF
- 427 Days On Market
Current Estimated Value $959,711

Last Listing Agent Tracey Petrusha Venture Realty Group

246 Colson Dr, Summerland Key, FL 33042
/20
$800,000 Sold Feb 24, 2025

27370 W Indies Dr, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 1992
Last Sold Summary
- 9% Below List Price
- $667/SF
- 118 Days On Market
Current Estimated Value $806,106

Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

27370 W Indies Dr, Summerland Key, FL 33042
/39
$1,150,000 Sold Nov 04, 2025

29676 Ranger Ave, Big Pine Key, FL 33043
- 2 Beds
- 2 Baths
- 1,064 Sq Ft
- Built 1987
Last Sold Summary
- 8% Below List Price
- $1,081/SF
- 87 Days On Market
Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

29676 Ranger Ave, Big Pine Key, FL 33043
/2
$73,000 Sold Feb 21, 2025

0 Valencia Rd, Cudjoe Key, FL 33042
- Land
- 1.01 Acres
- $72,147 per Acre
Last Sold Summary
- 64% Below List Price
- 30 Days On Market
Last Listing Agent Lauren Elliott EXP Realty, LLC

0 Valencia Rd, Cudjoe Key, FL 33042
/33
$665,000 Sold Aug 14, 2025

21161 Old State Road 4a, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 855 Sq Ft
- Built 1975
Last Sold Summary
- 5% Below List Price
- $778/SF
- 74 Days On Market
Current Estimated Value $669,907

Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

21161 Old State Road 4a, Summerland Key, FL 33042
/26
$730,000 Sold Nov 28, 2025

23930 Overseas Hwy, Summerland Key, FL 33042
- 3 Beds
- 3 Baths
- 1,360 Sq Ft
- Built 1946
Last Sold Summary
- 9% Below List Price
- $537/SF
- 137 Days On Market
Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

23930 Overseas Hwy, Summerland Key, FL 33042
/19
$335,000 Sold Feb 18, 2025

31008 Avenue B, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 684 Sq Ft
- Built 1973
Last Sold Summary
- 16% Below List Price
- $490/SF
- 264 Days On Market
Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

31008 Avenue B, Big Pine Key, FL 33043
/38
$680,000 Sold Feb 27, 2025

29842 Journeys End Rd, Big Pine Key, FL 33043
- 2 Beds
- 2 Baths
- 1,040 Sq Ft
- Built 1989
Last Sold Summary
- 1% Below List Price
- $654/SF
- 36 Days On Market
Current Estimated Value $680,856

Last Listing Agent Tracy Chacksfield Berkshire Hathaway HomeServices Keys Real Estate

29842 Journeys End Rd, Big Pine Key, FL 33043

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