8,628

Summerland Key, FL Homes

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  • /8

    $553,000 Sold Mar 06, 2026

    3 W Cook, Cook Island Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 704 Sq Ft
    • Built 1985

    Last Sold Summary

    • 8% Below List Price
    • $786/SF
    • 267 Days On Market

    Last Listing Agent Stephen Hachey

    3 W Cook, Cook Island Key, FL 33043
    • /46

      Est $2,886,507 Not Listed For Sale

      661 Sugarloaf Blvd, Summerland Key, FL 33042

      • 3 Beds
      • 4 Baths
      • 2,371 Sq Ft
      • Built 1967
      661 Sugarloaf Blvd, Summerland Key, FL 33042

      Last Sold Summary

      • 2% Above List Price
      • $1,244/SF
      • 78 Days On Market

      Last Sold Price $2,950,000

      Last Listing Agent Heather Bennett Keller Williams Key West Compass Realty

  • /15

    $1,395,000

    • Land
    • 2.29 Acres
    • $609,173 per Acre

    1261 Avenue A, Big Pine Key, FL 33043

    An ultra rare opportunity awaits on Big Pine Key. Spanning 2.29 acres with bay bottom and one-of-a-kind 35 by 70 foot saltwater tide pool, this remarkable parcel showcases panoramic open water views across Bogie Channel. A true sanctuary of privacy and natural beauty, the property sits at the end of a quiet street beside a peaceful County park, bordered further by County owned land to the west

    Ally Kelley Ocean Sotheby's International Realty

    1261 Avenue A, Big Pine Key, FL 33043
  • /36

    $755,000 Sold Sep 22, 2025

    1590 Gardenia Ln, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1977

    Last Sold Summary

    • 6% Below List Price
    • $629/SF
    • 104 Days On Market

    Current Estimated Value $765,862

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    1590 Gardenia Ln, Big Pine Key, FL 33043
    • /2

      Est $1,088,668 Not Listed For Sale

      467 Almond Ln, Big Pine Key, FL 33043

      • 3 Beds
      • 2 Baths
      • 1,390 Sq Ft
      • Built 1995
      467 Almond Ln, Big Pine Key, FL 33043

      Last Sold Summary

      • 2% Below List Price
      • $770/SF

      Last Sold Price $1,070,000

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

  • /24

    $259,000

    • Land

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

    RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

    Ian Calderwood Bluescape Real Estate

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
  • /42

    $775,000 Sold Oct 01, 2025

    22988 Port Royal Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,122 Sq Ft
    • Built 1998

    Last Sold Summary

    • 6% Below List Price
    • $691/SF
    • 68 Days On Market

    Current Estimated Value $779,721

    Last Listing Agent Walter Ceballos, P.A. Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    22988 Port Royal Ln, Summerland Key, FL 33042
    • /44

      Est $710,629 Not Listed For Sale

      29135 Camellia Ln, Big Pine Key, FL 33043

      • 3 Beds
      • 2 Baths
      • 1,238 Sq Ft
      • Built 1988
      29135 Camellia Ln, Big Pine Key, FL 33043

      Last Sold Summary

      • 2% Above List Price
      • $561/SF
      • 3 Days On Market

      Last Sold Price $695,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /24

    $350,000 Under Contract

    • Land

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

    The Ultimate Canal-Front RV Oasis in Venture Out at Cudjoe KeySeller says bring offers..Escape to your own slice of paradise with this prime waterfront RV lot in the sought-after, gated community of Venture Out on Cudjoe Key. This lot is built for the avid water enthusiast and provides a perfect base for exploring the best of the Lower and Middle Florida Keys.Fully Prepped RV Pad: Bring your rig

    Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
  • /77

    $2,500,000 Sold Jul 15, 2025

    943 Flagship Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 2001

    Last Sold Summary

    • 7% Below List Price
    • $1,395/SF
    • 121 Days On Market

    Current Estimated Value $2,511,873

    Last Listing Agent Lisa Swanson The Agency Florida Keys

    943 Flagship Dr, Summerland Key, FL 33042
    • /46

      Est $1,264,332 Not Listed For Sale

      137 Caribbean Dr E, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1986
      137 Caribbean Dr E, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Below List Price
      • $1,187/SF
      • 8 Days On Market

      Last Sold Price $1,329,000

      Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  • /2

    $275,000

    • Land

    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042

    Builders and Developers take a look at this 24 point lot that has a letter from Monroe County to be used toward building in the ROGO system. Contact Monroe County Building Department and/or the Monroe County Planning Department to verify use of this point lot. A great deal for anyone needing points to be competitive in the ROGO system.

    Pamela Stangler Expert Realty LLC

    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042
  • /39

    $650,000 Sold Apr 25, 2025

    25161 Center St, Summerland Key, FL 33042

    • 1 Bed
    • 1.5 Baths
    • 1,024 Sq Ft
    • Built 1958

    Last Sold Summary

    • 4% Below List Price
    • $635/SF
    • 6 Days On Market

    Current Estimated Value $628,335

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

    25161 Center St, Summerland Key, FL 33042
    • /26

      Est $730,519 Not Listed For Sale

      30946 Edward Rd, Big Pine Key, FL 33043

      • 4 Beds
      • 3 Baths
      • 1,794 Sq Ft
      • Built 2007
      30946 Edward Rd, Big Pine Key, FL 33043

      Last Sold Summary

      • 19% Above List Price
      • $343/SF
      • 19 Days On Market

      Last Sold Price $615,000

      Last Listing Agent Jenny Perry Preferred Properties (KW)

  • /73

    $1,699,000

    • 3 Beds
    • 3.5 Baths
    • 2,295 Sq Ft

    1136 W Shore Dr, Big Pine Key, FL 33043

    Seller says SELL IT! - Not a drive by- Must see inside and the back yard too.....Located on the West Side of the Island with excellent boating access this beautiful pool home is an entertainer's dream place. Stunning Sunsets & Sparkling waters for swimming, snorkeling, paddleboarding. Home features 3 bedroom suites with full baths plus a powder room too. Impact doors and windows, tile floors

    Beata Sharpe Coldwell Banker Vanguard Realty

    1136 W Shore Dr, Big Pine Key, FL 33043
  • /2

    $545,000 Sold May 22, 2025

    30276 Watson Blvd, Big Pine Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1989

    Last Sold Summary

    • $631/SF
    • 0 Days On Market

    Current Estimated Value $545,532

    Last Listing Agent Ally Kelley Ocean Sotheby's International Realty

    30276 Watson Blvd, Big Pine Key, FL 33043
    • /2

      Est $922,401 Not Listed For Sale

      22842 Buccaneer Ln, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,326 Sq Ft
      • Built 1998
      22842 Buccaneer Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 4% Below List Price
      • $671/SF

      Last Sold Price $890,000

      Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  • /46

    $2,250,000

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft

    1330 Sugarloaf Blvd, Summerland Key, FL 33042

    Discover the rare opportunity to own a masterfully renovated waterfront property that has remained entirely unoccupied and never lived in since its completion. This three-bedroom, two-bathroom residence offers the luxury of a home where every single element is 100% brand new and unused. The home comes completely turn-key and fully furnished with a curated collection of brand-new furniture,

    Brenda Donnelly Brenda Donnelly Real Estate LLC

    1330 Sugarloaf Blvd, Summerland Key, FL 33042
  • /41

    $970,000 Sold May 27, 2025

    366 Sawyer Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,390 Sq Ft
    • Built 1988

    Last Sold Summary

    • 19% Below List Price
    • $698/SF
    • 4 Days On Market

    Current Estimated Value $1,009,209

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    366 Sawyer Dr, Summerland Key, FL 33042
    • /24

      Est $1,006,457 Not Listed For Sale

      19453 Seminole St, Sugarloaf Key, FL 33042

      • 3 Beds
      • 2.5 Baths
      • 1,482 Sq Ft
      • Built 1986
      19453 Seminole St, Sugarloaf Key, FL 33042

      Last Sold Summary

      • 1% Above List Price
      • $675/SF
      • 2 Days On Market

      Last Sold Price $1,000,000

      Last Listing Agent The Donnelly Lowe Group Berkshire Hathaway HomeServices Knight & Gardner Realty

  • /34

    $469,000

    • 1 Bed
    • 1.5 Baths
    • 735 Sq Ft

    701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042

    Welcome to your opportunity in the gated waterfront community of Venture Out! This 1 bedroom, 1.5 bath property offers 35 feet of concrete seawall and direct canal access -- making it a true gem for boating enthusiasts and water lovers alike.Whether you're an investor searching for your next income-producing property or a creative buyer ready to design your own slice of paradise, this home offers

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042
  • /54

    $1,035,000 Sold Apr 14, 2025

    29013 Marigold Dr, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,614 Sq Ft
    • Built 1969

    Last Sold Summary

    • 13% Below List Price
    • $641/SF
    • 45 Days On Market

    Current Estimated Value $1,070,370

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    29013 Marigold Dr, Big Pine Key, FL 33043
    • /23

      Est $1,380,566 Not Listed For Sale

      30891 Granada Ave, Big Pine Key, FL 33043

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1987
      30891 Granada Ave, Big Pine Key, FL 33043

      Last Sold Summary

      • 2% Below List Price
      • $894/SF
      • 73 Days On Market

      Last Sold Price $1,402,000

      Last Listing Agent Sunnie San Lorenzo KeyIsle Realty

  • /32

    $1,125,000

    • 2 Beds
    • 2 Baths
    • 1,175 Sq Ft

    27821 Leeward South Rd, Little Torch Key, FL 33042

    ***OPEN HOUSE*** Saturday March 28th 10am-12pm. Location Location Location! This property offers lots of space, tons of privacy and stunning views. This home is situated on 2.38 acres of land with breathtaking open water views. Walk on to your newly refinished composite stairs to a walk around porch. Making access to the exterior of the home super easy. Interior layout is a large open floor plan

    Tracy Shields KeyIsle Realty

    27821 Leeward South Rd, Little Torch Key, FL 33042
  • /3

    $65,000 Sold Aug 04, 2025

    0 Spanish Channel Dr, No Name Key, FL 33043

    • Land

    Last Sold Summary

    • 86% Below List Price
    • 54 Days On Market

    Last Listing Agent Barbara Eads Barbara Eads Realty

    0 Spanish Channel Dr, No Name Key, FL 33043
    • /55

      Est $1,395,142 Not Listed For Sale

      350 W Shore Dr, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 2,108 Sq Ft
      • Built 1988
      350 W Shore Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 14% Above List Price
      • $581/SF
      • 279 Days On Market

      Last Sold Price $1,225,000

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

  • /24

    $580,175

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

    Licensed Nightly Rental Property!! Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for investors or those seeking a tranquil retreat. Currently operating as a successful vacation rental, this home is perfectly positioned to generate income or serve as your own private oasis. This property promises both convenience

    Sarah Dolson Keller Williams Key West Compass Realty

    701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
  • /53

    $615,000 Sold Mar 31, 2026

    29073 Iris Dr, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,336 Sq Ft
    • Built 1974

    Last Sold Summary

    • 2% Below List Price
    • $460/SF
    • 4 Days On Market

    Current Estimated Value $629,404

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

    29073 Iris Dr, Big Pine Key, FL 33043
    • /28

      Est $1,190,797 Not Listed For Sale

      2237 San Remo Dr, Big Pine Key, FL 33043

      • 2 Beds
      • 2 Baths
      • 1,244 Sq Ft
      • Built 1994
      2237 San Remo Dr, Big Pine Key, FL 33043

      Last Sold Summary

      • 1% Above List Price
      • $965/SF
      • 26 Days On Market

      Last Sold Price $1,200,000

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

  • /76

    $859,999

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    19512 Aztec St, Summerland Key, FL 33042

    Motivated seller! Bring all Reasonable offers 2 bedrooms, 1.5 baths with a 500sq ft screened lanai in the main building. There are 2 additional buildings that could be used as offices or bedrooms. Custom Pool with jacuzzi and swim jet. Completely remodeled in 2020 with new roof, new A/C. Located in the established Indian Mound Estates neighborhood w/ Access to private boat ramp with cabana and

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    19512 Aztec St, Summerland Key, FL 33042
  • /62

    $1,035,000 Sold Apr 01, 2026

    231 W Indies Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,377 Sq Ft
    • Built 1990

    Last Sold Summary

    • 4% Below List Price
    • $752/SF
    • 173 Days On Market

    Current Estimated Value $1,048,293

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    231 W Indies Dr, Summerland Key, FL 33042
    • /27

      Est $740,110 Not Listed For Sale

      1537 Pandorea Ln, Big Pine Key, FL 33043

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1973
      1537 Pandorea Ln, Big Pine Key, FL 33043

      Last Sold Summary

      • 64% Above List Price
      • $365/SF
      • 3 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Deni Heintzelman KeyIsle Realty

  • /4

    $275,000

    • Land

    27426 Martinique Ln, Summerland Key, FL 33042

    Vacant 6,000 SF lot in desirable Ramrod Key, ideally positioned near the world-class Looe Key Reef and just a five-minute boat ride to Picnic Island. This property offers an exceptional opportunity to build in one of the Lower Keys' most sought-after lifestyle locations. Walking distance to local favorites including The Tiki Bar and Boondocks Grille & Draft House. Buyer to obtain building permit

    Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    27426 Martinique Ln, Summerland Key, FL 33042
  • /58

    $835,000 Sold May 28, 2025

    23920 Overseas Hwy, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,242 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $672/SF
    • 60 Days On Market

    Current Estimated Value $868,963

    Last Listing Agent Aleida Ramirez United Realty Group Inc

    23920 Overseas Hwy, Summerland Key, FL 33042
    • /31

      Est $734,622 Not Listed For Sale

      174 Newfound Blvd, Big Pine Key, FL 33043

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1987
      174 Newfound Blvd, Big Pine Key, FL 33043

      Last Sold Summary

      • 5% Above List Price
      • $570/SF
      • 3 Days On Market

      Last Sold Price $702,500

      Last Listing Agent Melissa Graham Bluescape Real Estate

  • /35

    $699,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    31147 Avenue H, Big Pine Key, FL 33043

    Spring into summer with this gorgeous sparkling swimming pool! Enjoy snacks & meals poolside with handy outdoor kitchen which lends itself to awesome laid back island style entertaining! That's what we love about this remarkably well kept property! 3 comfortably sized bedrooms, 2 full bathrooms & a screened in porch contribute to what makes this the perfect place to call home! The up-to-date

    Jamie Caudill Lokation Real Estate

    31147 Avenue H, Big Pine Key, FL 33043
  • /35

    $945,000 Sold May 15, 2025

    17182 Starfish Ln W, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft
    • Built 1991

    Last Sold Summary

    • 3% Below List Price
    • $747/SF
    • 6 Days On Market

    Current Estimated Value $970,628

    Last Listing Agent Daniel Urban Expert Realty LLC (HQ)

    17182 Starfish Ln W, Summerland Key, FL 33042
    • /64

      Est $1,613,175 Not Listed For Sale

      553 Indies Rd, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,801 Sq Ft
      • Built 1996
      553 Indies Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 10% Below List Price
      • $999/SF
      • 76 Days On Market

      Last Sold Price $1,800,000

      Last Listing Agent Monica Barrett Coldwell Banker Schmitt Real Estate Co.

  • /12

    $599,000

    • Land

    16841 Driftwood Ln, Sugarloaf Shores, FL 33042

    **Tier III Beautiful Buildable Canal Front Lot in Sugarloaf Shores!**Discover an exceptional opportunity in the prestigious Sugarloaf Shores neighborhood with this oversized canal front lot, boasting 11,950 square feet. This prime piece of real estate offers quick boating access to both the Gulf of Mexico and the Atlantic Ocean.Key features include:- **Unparalleled Location:** Just 14 miles from

    Daiane Sardinas Carvalho Centennial Realty Group, LLC

    16841 Driftwood Ln, Sugarloaf Shores, FL 33042
  • /2

    $553,000 Sold Mar 06, 2026

    3 W Cook, Cook Island Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 750 Sq Ft
    • Built 1985

    Last Sold Summary

    • 8% Below List Price
    • $737/SF
    • 312 Days On Market

    Current Estimated Value $459,667

    Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

    3 W Cook, Cook Island Key, FL 33043

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