8,633

Summerland Key, FL Homes

Section Image
    • /40

      Est $831,843

      Not Listed For Sale

      27337 Tobago Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,080 Sq Ft
      • Built 1958
      27337 Tobago Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 7 Days On Market

  • /21

    $459,000

    $16K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 668 Sq Ft

    701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

    Ocean-View Retreat in Gated Waterfront Community on Cudjoe Key!NIGHTLY RENTALS ALLOWEDWelcome to your slice of paradise in the heart of the Florida Keys. This well-maintained 1-bedroom, 1-bathroom waterfront home is located inside the highly desirable, gated community of Venture Out, offering ocean views, direct boating access, and a plethora of amenities just steps away.The home features

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
  • /45

    $1,910,000

    Sold Feb 26, 2026

    1659 Long Beach Dr, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft
    • Built 1996

    Last Sold Summary

    • 4% Below List Price
    • $1,146/SF
    • 7 Days On Market

    Current Estimated Value $1,915,053

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    1659 Long Beach Dr, Big Pine Key, FL 33043
    • /2

      Est $2,584,723

      Not Listed For Sale

      20820 7th Ave W, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 2,000 Sq Ft
      • Built 1972
      20820 7th Ave W, Summerland Key, FL 33042

  • /61

    $639,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

    Spectacular peekaboo open water views abound with this updated 2 bed/2 bath canal front home with 35 foot seawall. Located in a gated community with tons of amenities. New kitchen w/Caesar quartz countertops, full backsplash, new stainless steel appliances, Koehler sink, modern, white cabinets with an abundance of storage, including a large center Island. Open concept floor plan with open water

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042
  • /12

    $650,000

    Sold Jul 08, 2026

    0 Dominica Ln Unit 615842, Ramrod Key, FL 33042

    • Land
    • 12,632 Sq Ft
    • $2,241,379 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 308 Days On Market

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    0 Dominica Ln Unit 615842, Ramrod Key, FL 33042
    • /48

      Est $1,000,115

      Not Listed For Sale

      27342 Anguila Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,320 Sq Ft
      • Built 1976
      27342 Anguila Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 36 Days On Market

  • /43

    $750,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    27024 Shannahan Rd, Summerland Key, FL 33042

    Well-maintained elevated home offering the perfect combination of comfort, functionality, and peace of mind. Built above flood elevation, this move-in-ready property features an open-concept floor plan with spacious living and dining areas, durable flooring throughout, and a bright kitchen with abundant cabinetry, stainless steel appliances, and generous counter space. The covered and screened

    Jenna Stauffer Ocean Sotheby's International Realty

    27024 Shannahan Rd, Summerland Key, FL 33042
  • /52

    $2,300,000

    Sold Sep 12, 2025

    23086 Snapper Ln, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,586 Sq Ft
    • Built 1985

    Last Sold Summary

    • 8% Below List Price
    • $889/SF
    • 147 Days On Market

    Current Estimated Value $2,325,082

    Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

    23086 Snapper Ln, Summerland Key, FL 33042
    • /68

      Est $2,607,325

      Not Listed For Sale

      531 Seminole Dr, Summerland Key, FL 33042

      • 4 Beds
      • 3 Baths
      • 2,604 Sq Ft
      • Built 1985
      531 Seminole Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 57 Days On Market

  • /65

    $1,595,000

    • 3 Beds
    • 3 Baths
    • 2,022 Sq Ft

    887 Bay Dr, Summerland Key, FL 33042

    Priced at Current appraised value, this 3-bedroom, 3-bath concrete fortress on deep water canal (5' draft) is located in the highly sought-after Summerland Cove with quick access to both the Gulf and Atlantic--just a 15-minute boat ride to open ocean--this home is a true boater's paradise. Additionally, enjoy Airstrip rights as part of the Summerland Airport community. Set on a generous 75' x

    Amy Hanson Realty Executives Florida Keys Summerland Branch

    887 Bay Dr, Summerland Key, FL 33042
  • /32

    $455,000

    Sold Feb 25, 2026

    31129 Avenue G, Big Pine Key, FL 33043

    • 3 Beds
    • 2.5 Baths
    • 844 Sq Ft
    • Built 1994

    Last Sold Summary

    • $539/SF
    • 52 Days On Market

    Last Listing Agent Ted Stewart Truman & Co. (KW)

    31129 Avenue G, Big Pine Key, FL 33043
    • /30

      Est $2,314,280

      Not Listed For Sale

      17082 Starfish Ln W, Summerland Key, FL 33042

      • 6 Beds
      • 3 Baths
      • 3,000 Sq Ft
      • Built 1988
      17082 Starfish Ln W, Summerland Key, FL 33042

      Last Sold Summary

      • 38 Days On Market

  • /34

    $899,000

    • 1 Bed
    • 1 Bath
    • 552 Sq Ft

    31342 Avenue I, Big Pine Key, FL 33043

    This recently built canal front home is situated in a highly desirable area of Big Pine just minutes to the open water. The home has a bright open kitchen with plenty of cabinets, stainless appliances, attractive tile backsplash and built in table with seating overlooking the living area.......From the bedroom with adjoined bathroom there are partial ocean views. There is also a utility room with

    Rob Severin Rob Severin Real Estate Co

    31342 Avenue I, Big Pine Key, FL 33043
  • /22

    $649,000

    Sold May 20, 2026

    19591 Navajo St, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft
    • Built 1994

    Last Sold Summary

    • 4% Below List Price
    • $624/SF
    • 25 Days On Market

    Current Estimated Value $657,742

    Last Listing Agent Mike Kane Internet Realty of the Florida Keys

    19591 Navajo St, Summerland Key, FL 33042
    • /2

      Est $979,663

      Not Listed For Sale

      17174 Kingfish Ln W, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,218 Sq Ft
      • Built 1975
      17174 Kingfish Ln W, Summerland Key, FL 33042

  • /42

    $849,000

    • 3 Beds
    • 2 Baths
    • 984 Sq Ft

    937 Loggerhead Ln, Summerland Key, FL 33042

    Opportunities like this are hard to find in the Lower Keys--this fully renovated 3-bedroom, 2-bath home sits on a generous half-acre lot in the highly desirable Sugarloaf Key area, offering space, privacy, and modern upgrades throughout. Designed for easy coastal living, the home features durable Hardie board siding, a long-lasting metal roof, tile flooring throughout, and an energy-efficient

    Richard Haskins Buy The Keys

    937 Loggerhead Ln, Summerland Key, FL 33042
  • /42

    $630,000

    Sold Jul 21, 2025

    92 Frazier Ln, Summerland Key, FL 33042

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

    Last Sold Summary

    • 9% Below List Price
    • $820/SF
    • 43 Days On Market

    Current Estimated Value $563,620

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

    92 Frazier Ln, Summerland Key, FL 33042
    • /50

      Est $1,966,976

      Not Listed For Sale

      21025 Hamilton Ave, Summerland Key, FL 33042

      • 6 Beds
      • 3.5 Baths
      • 4,060 Sq Ft
      • Built 1983
      21025 Hamilton Ave, Summerland Key, FL 33042

      Last Sold Summary

      • 47 Days On Market

  • /3

    $179,000

    $20K PRICE DROP Pending
    • Land
    • 4,791 Sq Ft
    • $1,627,273 per Acre

    Lot 32 Caloosa St, Sugarloaf, FL 33042

    Lot with ROGO letter for 5 points. Not ROGO exempt, use points towards building on another lot or contact the Monroe County Planning Department for information about building on this lot or how to use these points. Tier 3 AE11. Contact Monroe County to verify all information. ROGO letter available upon request.

    Pamela Stangler MMLS Assoc.-Inactive Member

    Lot 32 Caloosa St, Sugarloaf, FL 33042
  • /29

    $1,400,000

    Sold Apr 24, 2026

    20841 8th Ave W, Cudjoe Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 1994

    Last Sold Summary

    • 10% Below List Price
    • $748/SF
    • 82 Days On Market

    Current Estimated Value $1,491,708

    Last Listing Agent Collin Tingle Coldwell Banker Schmitt Lower Keys (KW)

    20841 8th Ave W, Cudjoe Key, FL 33042
    • /2

      Est $1,045,974

      Not Listed For Sale

      152 Sugarloaf Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft
      • Built 1995
      152 Sugarloaf Dr, Summerland Key, FL 33042

  • /46

    $899,000

    $150K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    288 Spanish Main Dr, Summerland Key, FL 33042

    MAJOR PRICE IMPROVEMENT -- AN EXCEPTIONAL VALUE FOR A BEAUTIFULLY UPDATED CUDJOE KEY CANAL-FRONT HOME! This updated 3-bedroom, 2-bath canal-front home on Cudjoe Key offers approximately 60 feet of concrete dockage directly behind the property, with plenty of room for your boat and convenient access to Gulf and Atlantic waters for fishing, diving, sandbar trips, and cruising the Lower Keys. The

    Richard Haskins Buy The Keys

    288 Spanish Main Dr, Summerland Key, FL 33042
  • /16

    $785,000

    Sold Jul 25, 2025

    27384 Barbuda Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft
    • Built 1993

    Last Sold Summary

    • 17% Below List Price
    • $668/SF
    • 125 Days On Market

    Current Estimated Value $847,836

    Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

    27384 Barbuda Ln, Summerland Key, FL 33042
    • /31

      Est $657,302

      Not Listed For Sale

      701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042

      • 2 Beds
      • Built 1991
      701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042

      Last Sold Summary

      • 15 Days On Market

  • /20

    $4,200

    Pending
    • 2 Beds
    • 2 Baths
    • 1,332 Sq Ft

    1129 Gordon Dr, Big Pine Key, FL 33043

    Tropical Island Living in Big Pine Key! Welcome to your slice of paradise! This beautifully renovated property offers: a long term residential lease for 1 yearTwo bedroom and two bathrooms for $4,200 +$300 for one monthly cleaning. plus $175 additional for the yard care and utility expenses energy, water, propane for generator. Tank will be full at commencement of lease. Upstairs: A fully

    Jennifer Howe Coastal Collection Real Estate Inc.

    1129 Gordon Dr, Big Pine Key, FL 33043
  • /14

    $1,250,000

    Sold Aug 11, 2025

    365 Pirates Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $893/SF
    • 47 Days On Market

    Current Estimated Value $1,273,183

    Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.

    365 Pirates Rd, Summerland Key, FL 33042
    • /15

      Est $740,460

      Not Listed For Sale

      16991 Shore Dr, Summerland Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 1,134 Sq Ft
      • Built 1958
      16991 Shore Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 17 Days On Market

  • /7

    $170,000

    • Land
    • 5,662 Sq Ft
    • $1,307,692 per Acre

    Lot 27 Dorn Rd, Torch Key, FL 33042

    If you love fishing, love the water, and hate the big crowds, this is the place for you! Upon arrival, the first thing you will notice is the peace and quiet. Easy access to the Gulf of America and Atlantic Ocean. This property is adjacent to my other listing which is owned by the same person. This would be an excellent opportunity to own a double lot on Big Torch Key! Adjacent property (blue

    Dylan Calhoun Luxe Properties

    Lot 27 Dorn Rd, Torch Key, FL 33042
  • /59

    $900,000

    Sold Oct 31, 2025

    28550 Doubloon Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 2,371 Sq Ft
    • Built 1996

    Last Sold Summary

    • 18% Below List Price
    • $380/SF
    • 181 Days On Market

    Current Estimated Value $956,934

    Last Listing Agent Kelly Randin RE/MAX All Keys Real Estate

    28550 Doubloon Rd, Summerland Key, FL 33042
    • /56

      Est $1,799,871

      Not Listed For Sale

      20966 8th Ave W, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 2,166 Sq Ft
      • Built 1982
      20966 8th Ave W, Summerland Key, FL 33042

      Last Sold Summary

      • 31 Days On Market

  • /42

    $727,000

    $58K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,008 Sq Ft

    31033 Hibiscus Dr, Big Pine Key, FL 33043

    Nestled in the heart of Big Pine Key, this charming A-frame home offers classic Florida Keys character on an oversized DOUBLE LOT with canal frontage and excellent boating access to Bogie Channel. Built in 1973 and constructed with metal beams, this just-over-1,000-square-foot home blends durability with coastal charm. Or you may just want to demo the house and build your Keys Dream Home on two

    Karen Haack Coldwell Banker Schmitt RE Co.

    31033 Hibiscus Dr, Big Pine Key, FL 33043
  • /47

    $1,100,000

    Sold Jun 12, 2026

    43 Venetian Way, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Built 1982

    Last Sold Summary

    • 17% Below List Price
    • $880/SF
    • 497 Days On Market

    Current Estimated Value $1,089,361

    Last Listing Agent Lori Cameron Buy The Keys

    43 Venetian Way, Summerland Key, FL 33042
    • /21

      Est $769,175

      Not Listed For Sale

      19570 Mayan St, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,424 Sq Ft
      • Built 1958
      19570 Mayan St, Summerland Key, FL 33042

      Last Sold Summary

      • 1 Day On Market

  • /12

    $240,000

    Pending
    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    28177 Julia Ave, Little Torch Key, FL 33042

    Opportunity to purchase for land value in Little Torch Key. Large lot with existing mobile home on site that is not habitable. Property is being marketed as land only. Lot is zoned IS (Improved Subdivision District), which typically allows for single-family residential construction subject to Monroe County Land Development Code and applicable ROGO requirements. Conveniently located less than 5

    Maria Acosta Keller Williams Capital Realty

    28177 Julia Ave, Little Torch Key, FL 33042
  • /24

    $710,000

    Sold Dec 18, 2025

    31120 Avenue J, Big Pine Key, FL 33043

    • 2 Beds
    • 1.5 Baths
    • 864 Sq Ft
    • Built 2022

    Last Sold Summary

    • 9% Below List Price
    • $822/SF
    • 83 Days On Market

    Current Estimated Value $714,739

    Last Listing Agent David Kaufmann Century 21 Circle

    31120 Avenue J, Big Pine Key, FL 33043
    • /73

      Est $1,101,368

      Not Listed For Sale

      103 Shore Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,128 Sq Ft
      • Built 1989
      103 Shore Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 24 Days On Market

  • /49

    $1,450,000

    $150K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,396 Sq Ft

    29635 Saratoga Ave, Big Pine Key, FL 33043

    Welcome to your slice of island paradise in Pine Channel Estates in Big Pine Key! This beautifully built 3bedroom, 2bath CBS home offers the perfect blend of durability, comfort, and laid-back Keys living. Constructed with poured concrete floors and designed for peace of mind, the home features a tiled interior, a tiled roof, and convenient accordion shutters throughout. Step outside and embrace

    Karen Haack Coldwell Banker Schmitt RE Co.

    29635 Saratoga Ave, Big Pine Key, FL 33043
  • /5

    $328,000

    Sold Mar 27, 2026

    28292 Dorothy Ave, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 830 Sq Ft
    • Built 1975

    Last Sold Summary

    • $395/SF
    • 4 Days On Market

    Last Listing Agent Lauren Dunn Coldwell Banker Schmitt Islamorada

    28292 Dorothy Ave, Summerland Key, FL 33042
    • /46

      Est $1,318,593

      Not Listed For Sale

      817 Grenada Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2.5 Baths
      • 1,819 Sq Ft
      • Built 1993
      817 Grenada Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 25 Days On Market

Showing Results 521 - 560, Page 14 of 18

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