Cudjoe Key, FL Homes

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  $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 Bea Evelyn Citron Compass Florida, LLC

  701 Spanish Main Dr Unit LOT 102, Cudjoe Key, FL 33042
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  /60

  Est $936,788 Not Listed For Sale

  52 Cutthroat Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1988

  52 Cutthroat Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 6% Above List Price
  • $636/SF
  • 58 Days On Market

  Last Sold Price $885,000

  Last Listing Agent Pamela Stangler Expert Realty LLC
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  /37

  $879,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

  VACATION RENTAL OPPORTUNITY - OPEN WATER VIEWS + 43' DOCK - 2BR/2BA | 864 SQ. FT.Beautifully maintained 2-bedroom, 2-bath waterfront home offering open water views and excellent rental potential. This 864 sq. ft. property features a 43-foot dock with quick access to world-class boating, fishing, and diving in the Florida Keys. Ideal for investors or owners seeking a turn-key vacation rental

  Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
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  $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
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  /34

  Est $775,837 Not Listed For Sale

  191 Doubloon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1963

  191 Doubloon Ln, Summerland Key, FL 33042

  Last Sold Summary

  • $578/SF
  • 10 Days On Market

  Last Sold Price $775,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  $190,000

  • Land
  • 6,000 Acres
  • $32 per Acre

  1145 Hakluyt Ln, Cudjoe Key, FL 33042

  Discover one of Cudjoe Key’s desirable vacant parcels — a 6,000 sq ft waterfront lot offering direct access to the Lower Keys’. Located on a quiet road, this property pairs privacy with easy access to local conveniences and the laid-back lifestyle of the Lower Keys. Enjoy morning coffee with ocean breezes, evening skies, and endless outdoor living possibilities.(Information provided herein is

  Daniel Pacheco United Realty Group Inc

  1145 Hakluyt Ln, Cudjoe Key, FL 33042
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  /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 $682,721

  Last Listing Agent Ally Kelley Ocean Sotheby's International Realty

  268 Spanish Main Dr, Summerland Key, FL 33042
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  /77

  Est $5,872,168 Not Listed For Sale

  200 Erie Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 4,514 Sq Ft
  • Built 2002

  200 Erie Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 11% Below List Price
  • $1,468/SF
  • 295 Days On Market

  Last Sold Price $6,625,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /55

  $925,000

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042

  ********Nightly Licensed Transient Rental!!!********This amazing, two bedroom / one bathroom, open water front, nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rental license. The floor plan makes the open water views as its main focus. Cook the catch of the day overlooking the waters that you just caught that prized fish in. Sit

  Bobby Coe RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
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  /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 $890,916

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  22971 Hawkins Ln, Summerland Key, FL 33042
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  /41

  Est $1,395,564 Not Listed For Sale

  20785 5th Ave W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • Built 1990

  20785 5th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 1% Above List Price
  • $917/SF
  • 77 Days On Market

  Last Sold Price $1,375,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /59

  $535,000

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
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  $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 $986,468

  Last Listing Agent Tracey Petrusha Venture Realty Group

  246 Colson Dr, Summerland Key, FL 33042
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  /45

  Est $1,356,582 Not Listed For Sale

  622 Sawyer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3.5 Baths
  • 2,156 Sq Ft
  • Built 1986

  622 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 46% Below List Price
  • $1,169/SF
  • 156 Days On Market

  Last Sold Price $2,520,000

  Last Listing Agent Laura Derrickson Keller Williams Coastal Partners
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  /18

  $445,000

  • Land

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

  Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

  Bea Evelyn Citron Compass Florida, LLC

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
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  /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 $636,290

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

  21161 Old State Road 4a, Summerland Key, FL 33042
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  /43

  Est $1,398,326 Not Listed For Sale

  408 Sawyer Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,330 Sq Ft
  • Built 1989

  408 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 7% Below List Price
  • $1,128/SF
  • 16 Days On Market

  Last Sold Price $1,500,000

  Last Listing Agent Kathryn Baldwin Bluescape Real Estate
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  /55

  $339,000

  • 2 Beds
  • 1.5 Baths
  • 748 Sq Ft

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042

  Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental as

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
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  /68

  $2,600,000 Sold May 30, 2025

  531 Seminole Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,604 Sq Ft
  • Built 1985

  Last Sold Summary

  • 13% Below List Price
  • $998/SF
  • 57 Days On Market

  Current Estimated Value $2,647,654

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  531 Seminole Dr, Summerland Key, FL 33042
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  /14

  Est $2,884,713 Not Listed For Sale

  683 Sawyer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,561 Sq Ft
  • Built 1985

  683 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 4% Above List Price
  • $1,922/SF
  • 22 Days On Market

  Last Sold Price $3,000,000

  Last Listing Agent Ashkarian Ardis Team Coldwell Banker Schmitt Real Estate Co.
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  /54

  $799,000

  • 2 Beds
  • 2 Baths
  • 640 Sq Ft

  701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042

  Luxurious Waterfront Living - Welcome to your perfect coastal oasis in the sought-after community of Venture Out! This contemporary high-rise boasts million-dollar views from every angle, including a screened patio for ultimate enjoyment. With an outside elevator providing easy access, this stunning home features a serene primary suite with stylish decor and a beautiful walk-in shower in the

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
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  /22

  $257,500 Sold Feb 17, 2026

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

  • Land

  Last Sold Summary

  • 2% Below List Price
  • 21 Days On Market

  Current Estimated Value $257,870

  Last Listing Agent Mary Bryant Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042
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  /32

  Est $1,968,703 Not Listed For Sale

  21018 4th Ave, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,966 Sq Ft
  • Built 1994

  21018 4th Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 24% Above List Price
  • $534/SF
  • 302 Days On Market

  Last Sold Price $1,585,000

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)
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  /18

  $255,000

  • Land

  701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042

  Welcome to RV Lot 642, located in the gated, waterfront community of Venture Out on Cudjoe Key. This well-positioned lot offers the perfect setup for your Florida Keys getaway, seasonal stay, or investment opportunity.Enjoy all the perks of a golf-cart-friendly community with resort-style amenities, including a large saltwater pool, marina with boat ramp, pickleball and tennis courts, bocce,

  Bea Evelyn Citron Compass Florida, LLC

  701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
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  /15

  $250,000 Sold Sep 30, 2025

  701 Spanish Main Dr Unit 147, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 12% Below List Price
  • 60 Days On Market

  Last Listing Agent Bea Evelyn Citron Compass Florida, LLC

  701 Spanish Main Dr Unit 147, Cudjoe Key, FL 33042
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  Est $880,377 Not Listed For Sale

  21702 Asturias Rd, Summerland Key, FL 33042

  • 4 Beds
  • 2.5 Baths
  • 1,584 Sq Ft
  • Built 1982

  21702 Asturias Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 27% Above List Price
  • $439/SF
  • 47 Days On Market

  Last Sold Price $695,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  $349,000

  • 2 Beds
  • 1 Bath
  • 388 Sq Ft

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

  Great opportunity to own an income-producing home in the gated community of Venture Out on Cudjoe Key. This 2-bedroom, 1-bath mobile home features a cozy layout with a true Florida Keys feel throughout. The property is ideally situated on a private lot with no neighbors on one side or behind, offering added privacy and tranquility. Whether you're looking for a full-time residence or a turnkey

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
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  /2

  $55,000 Sold Dec 04, 2025

  Lot 16 Treasure Chest Dr, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 90% Above List Price
  • 73 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 16 Treasure Chest Dr, Cudjoe Key, FL 33042
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  Est $1,248,700 Not Listed For Sale

  21790 Spain Blvd, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,790 Sq Ft
  • Built 1978

  21790 Spain Blvd, Summerland Key, FL 33042

  Last Sold Summary

  • 9% Above List Price
  • $642/SF
  • 86 Days On Market

  Last Sold Price $1,150,000

  Last Listing Agent Nate Meyer Meyer and Boumerhi Realty LLC
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  /75

  $915,000 Open Thu 10:30AM - 1:30PM

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042

  This is the house for your boat!ENDLESS OCEANFRONT LIVING - 47' SEAWALLWake up every morning to sweeping sunrises & unobstructed views of the turquoise Atlantic at this extraordinary one-of-a-kind, oceanfront residence. The 'Crown Jewel of the Ocean' located just 19 miles from Key West, this beautifully appointed 2-bedroom, 2-bath mid-rise home offers front-row seats to the water & an unmatched

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
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  /34

  $950,000 Sold Mar 03, 2026

  1193 de Lussan Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2012

  Last Sold Summary

  • 5% Below List Price
  • $800/SF
  • 6 Days On Market

  Current Estimated Value $999,865

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  1193 de Lussan Ln, Cudjoe Key, FL 33042
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  /29

  Est $1,108,275 Not Listed For Sale

  23034 Wahoo Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1992

  23034 Wahoo Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 8% Above List Price
  • $1,153/SF
  • 27 Days On Market

  Last Sold Price $1,199,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /42

  $650,000

  • Land

  22948 Drake Ln, Summerland Key, FL 33042

  Boater/Angler special: 70-foot concrete seawall features hard-to-find boat slip/basin, plus 10,000-pound boat lift . This canal front-vacant lot is ROGO exempt and ready to build on. It corners Drake Lane's dead end and is second from Cudjoe Bay's open water. Perfect location for new build. Previous house removed and lot is ready for your vision. Electric was in place, buyer to verify FKAA

  Barbara Bowers Preferred Properties (KW)

  22948 Drake Ln, Summerland Key, FL 33042
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  /39

  Est $1,404,786 Not Listed For Sale

  21076 3rd Ave, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,732 Sq Ft
  • Built 1992

  21076 3rd Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 8% Below List Price
  • $886/SF
  • 33 Days On Market

  Last Sold Price $1,535,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /55

  $999,000

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  22978 Port Royal Ln, Summerland Key, FL 33042

  Ocean side location enjoy diving , fishing, dining from your boat come home to relax on your deck watching the sunset. Open floor plan new upgrades throughout.Several pictures added with staged furnishing for you to see what rooms could look like.Extra large property with plenty of room for your R/V, boats. Your own boat launch with plenty of dockage on your concrete seawall. Beautifully

  Anne Press Lokation Real Estate

  22978 Port Royal Ln, Summerland Key, FL 33042
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  /28

  Est $991,640 Not Listed For Sale

  340 Spanish Main Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1997

  340 Spanish Main Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 2% Above List Price
  • $821/SF
  • 11 Days On Market

  Last Sold Price $975,000

  Last Listing Agent Lindsay Ryan EXP Realty LLC
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  /46

  $409,000

  • 2 Beds
  • 1 Bath
  • 833 Sq Ft

  701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042

  This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 1 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
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  /36

  Est $1,449,416 Not Listed For Sale

  20878 5th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1992

  20878 5th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 2% Above List Price
  • $955/SF
  • 296 Days On Market

  Last Sold Price $1,480,000

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt Lower Keys (KW)
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  /77

  $440,000

  • Land

  701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042

  Ocean View Canal Front RV Lot in Venture Out - 35' Concrete SeawallBuild, park, invest, or simply pull in and start living the Keys lifestyle. This 35' x 69' beautiful, waterfront RV lot in the private, gated community of Venture Out offers ocean views, a 35' concrete seawall, and direct boating access to both the Atlantic and backcountry waters.The lot features a concrete pad and walkway,

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
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  /53

  Est $899,746 Not Listed For Sale

  22977 Long Ben Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1987

  22977 Long Ben Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 6% Above List Price
  • $746/SF
  • 46 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

Showing Results 241 - 280, Page 7 of 18