Summerland Key, FL Homes

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  /51

  $990,000

  Sold Oct 28, 2025

  22841 Buccaneer Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Below List Price
  • $516/SF
  • 139 Days On Market

  Current Estimated Value $1,122,753

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22841 Buccaneer Ln, Summerland Key, FL 33042
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  /41

  Est $1,461,702

  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

  • 77 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  

  /28

  $995,000

  $204K PRICE DROP

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

  27452 Anguila Ln, Summerland Key, FL 33042

  OWNER FINANCING. 27452 ANGUILA LANE RAMROD KEY FOR RENT. REPAINTED INSIDE AND OUT. ALL NEW FLOORING. 1400 SQFT 180 MPH RATED 3/2 HOME. 300SQFT ENCLOSURE FOR ALL YOUR FISHING NEEDS.40' DOCK ON AN OVERSIZED CORNER LOT WITH LOTS OF ROOM FOR RV AN BOAT PARKING. MINUTES FROM LOOE KEY REEF. 9' CEILINGS, CROWN MOLDING AND CENTRAL AC. FULLY PEA ROCKED YARD FOR LOW MAINTENANCE. NEW METAL ROOF, HURRICANE

  Charles Roberts ICAMCO Realty LLC, dba Cosgrove Realty

  27452 Anguila Ln, Summerland Key, FL 33042
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  /7

  $1,600,000

  Sold Nov 21, 2025

  23038 Overseas Hwy, Cudjoe Key, FL 33042

  • Land
  • 1.37 Acres
  • $1,164,531 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 141 Days On Market

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  23038 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  

  /13

  Est $1,869,383

  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

  • 0 Days On Market

  Last Listing Agent Laura Derrickson Keller Williams Coastal Partners
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  /59

  $535,000

  $14K PRICE DROP

  • 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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  /47

  $895,000

  Sold Dec 10, 2025

  22880 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 1,256 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Below List Price
  • $713/SF
  • 34 Days On Market

  Current Estimated Value $906,336

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22880 Blackbeard Ln, Summerland Key, FL 33042
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  /43

  Est $1,394,754

  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

  • 16 Days On Market

  Last Listing Agent Kathryn Baldwin Bluescape Real Estate
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  /50

  $289,000

  Under Contract

  • 1 Bed
  • 1 Bath
  • 340 Sq Ft

  701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042

  Welcome to Coconut Cottage #653, a charming island retreat located in the gated waterfront community of Venture Out on Cudjoe Key. This cozy 1BD/1BA home is the perfect Florida Keys getaway, ideal as a vacation rental investment, seasonal escape, or personal retreat. Turn-key and ready to enjoy or rent immediately, this property offers excellent income potential with nightly rentals allowed in

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042
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  /38

  $775,000

  Sold Sep 11, 2025

  22957 Drake Ln, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $769/SF
  • 7 Days On Market

  Current Estimated Value $818,910

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22957 Drake Ln, Cudjoe Key, FL 33042
• 

  

  /29

  Est $1,031,856

  Not Listed For Sale

  1107 Hawksbill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1984

  1107 Hawksbill Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Richard Haskins Buy The Keys
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  /46

  $695,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  29172 Rose Dr, Big Pine Key, FL 33043

  Remodeled waterfront home! Located in a lovely neighborhood with a boat ramp right around the corner! Exterior of property has open parking as well as covered parking for multiple vehicles. Below home is surrounded by lattice to give additional shade and privacy. So much potential downstairs for outdoor entertainment.The main living area has gone through a full renovation. Kitchen boast sleek

  Deni Heintzelman KeyIsle Realty

  29172 Rose Dr, Big Pine Key, FL 33043
• 

  

  /24

  $430,000

  Sold Nov 25, 2025

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042

  • Land
  • 2,078 Sq Ft
  • $9,013,859 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 287 Days On Market

  Current Estimated Value $426,687

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042
• 

  /2

  Est $774,442

  Not Listed For Sale

  19514 Canal Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1995

  19514 Canal Dr, Summerland Key, FL 33042
• 

  

  /52

  $949,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  22811 Buccaneer Ln, Summerland Key, FL 33042

  Looking for a move-in-ready waterfront home with concrete block construction and quick boating access? This beautifully updated Cudjoe Key retreat checks all the boxes! Tucked away on the south side of the neighborhood, you'll be just minutes from open water while enjoying a peaceful setting away from the noise of US-1. At the same time, you'll still be close to Lower Keys favorites like Square

  Madeleine Young Island Welcome Real Estate LLC

  22811 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /52

  $865,000

  Sold Apr 23, 2026

  1539 Lantana Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1999

  Last Sold Summary

  • 3% Below List Price
  • $792/SF
  • 19 Days On Market

  Current Estimated Value $868,429

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

  1539 Lantana Ln, Big Pine Key, FL 33043
• 

  

  /5

  Est $740,553

  Not Listed For Sale

  19462 Canal Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft
  • Built 1990

  19462 Canal Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Jacqui Norman Berkshire Hathaway HomeServices Knight & Gardner Realty
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  /63

  $3,295,000

  $400K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft

  24348 Caribbean Dr W, Summerland Key, FL 33042

  A stunning location with all attributes geared to the view of the beautiful open bay of Summerland Cove. This OCEANFRONT 3 bedroom 3 bath home is on the market for the first time since construction in 1996 and features an extensive renovation nearly complete. The property includes a stunning covered & heated pool with screened enclosure, a 28 foot concrete dock with davits, deep water boating

  Caroline Bauer Key West Sales, LLC

  24348 Caribbean Dr W, Summerland Key, FL 33042
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  /61

  $2,000,000

  Sold Mar 18, 2026

  743 Pattison Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Built 1997

  Last Sold Summary

  • 11% Below List Price
  • $1,195/SF
  • 135 Days On Market

  Current Estimated Value $2,007,884

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  743 Pattison Dr, Summerland Key, FL 33042
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  /42

  Est $549,775

  Not Listed For Sale

  92 Frazier Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2.5 Baths
  • 768 Sq Ft
  • Built 1980

  92 Frazier Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 43 Days On Market

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

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