8,476

Summerland Key, FL Homes

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    • /2

      Est $3,977,169

      Not Listed For Sale

      1152 W Shore Dr, Big Pine Key, FL 33043

      • 3 Beds
      • 3 Baths
      • 4,030 Sq Ft
      • Built 2008
      1152 W Shore Dr, Big Pine Key, FL 33043

  • /24

    $259,000

    $6K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $5,180,000 per Acre

    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

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
  • /40

    $640,000

    Sold Sep 15, 2025

    3806 Dyer Rd, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft
    • Built 1990

    Last Sold Summary

    • 8% Below List Price
    • $702/SF
    • 54 Days On Market

    Current Estimated Value $671,988

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

    3806 Dyer Rd, Big Pine Key, FL 33043
    • /3

      Est $1,330,609

      Not Listed For Sale

      Unlisted Address

      • 5 Beds
      • 4 Baths
      • 1,702 Sq Ft
      • Built 1967
      Unlisted Address

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  • /52

    $2,300,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    30995 Watson Blvd, Big Pine Key, FL 33043

    Brand-New Waterfront Home - Completed and Move-In Ready. This elevated CBS single-level residence offers 4 bedrooms, 3 bathrooms, 10-foot ceilings, impact-rated windows and doors, durable metal roof, stainless steel appliances, quartz countertops, open-concept living areas, screened porch, private in-ground pool, and covered parking below. Built with modern coastal construction in mind, the CBS

    Banks Prevatt Coldwell Banker Schmitt RE Co.

    30995 Watson Blvd, Big Pine Key, FL 33043
  • /36

    $1,100,000

    Sold Jun 12, 2026

    22874 Bluegill Ln, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 1,518 Sq Ft
    • Built 1972

    Last Sold Summary

    • 6% Below List Price
    • $725/SF
    • 7 Days On Market

    Current Estimated Value $1,121,314

    Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

    22874 Bluegill Ln, Summerland Key, FL 33042
    • /49

      Est $768,721

      Not Listed For Sale

      25121 Center St, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 2008
      25121 Center St, Summerland Key, FL 33042

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Gregory Sullivan BYOWNER.COM

  • /51

    $425,000

    • 2 Beds
    • 1 Bath
    • 748 Sq Ft

    701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042

    Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom, 1 bathroom manufactured home has high ceilings that allow great entertaining from the kitchen, dining room, and living room area. Features a large master bedroom, full size bathroom with new vanity and new stackable washer/dryer, well stocked kitchen with a full line of appliances, metal roof, and tile

    Justyn Ewald Expert Realty LLC

    701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042
  • /57

    $925,000

    Sold Mar 13, 2026

    2123 Spanish Channel Dr, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,185 Sq Ft
    • Built 1991

    Last Sold Summary

    • 6% Below List Price
    • $781/SF
    • 49 Days On Market

    Current Estimated Value $929,282

    Last Listing Agent Anne Press Lokation Real Estate

    2123 Spanish Channel Dr, Big Pine Key, FL 33043
    • /38

      Est $937,968

      Not Listed For Sale

      22971 Hawkins Ln, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,142 Sq Ft
      • Built 1987
      22971 Hawkins Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  • /32

    $975,000

    $20K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft

    29131 Watson Blvd, Big Pine Key, FL 33043

    Peaceful serenity found on this 22,077 square foot property with a cozy two bedroom one and one-half bath. Open concept large kitchen and living room leading out to the expansive deck overlooking the canal. Both bedrooms also have doors leading to the wrap around deck! The cathedral ceilings and wood trims give this home beach cottage character! The lower level has an amazing amount of storage

    Mary Conklin Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    29131 Watson Blvd, Big Pine Key, FL 33043
  • /9

    $100,000

    Sold Oct 29, 2025

    4W Cook Island, Big Pine Key, FL 33043

    • Land
    • 14,809 Sq Ft
    • $294,126 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 194 Days On Market

    Current Estimated Value $126,333

    Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.

    4W Cook Island, Big Pine Key, FL 33043
    • /55

      Est $1,424,874

      Not Listed For Sale

      266 Colson Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,943 Sq Ft
      • Built 1975
      266 Colson Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /51

    $1,599,900

    $75K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft

    559 Powell Ave, Little Torch Key, FL 33042

    Built in 2019 on a Double Lot! This modern home features three (3) bedrooms and two (2) bathrooms, offering everything you need. It's low maintenance yet packed with amenities. Enjoy a pool, a double lot, an extra-long dock, affordable insurance, a quiet, peaceful neighborhood, and excellent fishing opportunities.Step inside to an open-concept design that boasts a bright & fantastic

    Bobby Coe RE/MAX Keys Connection (KW)

    559 Powell Ave, Little Torch Key, FL 33042
  • /47

    $1,399,000

    Sold Jun 17, 2026

    823 Indies Rd, Ramrod Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 2006

    Last Sold Summary

    • $925/SF
    • 5 Days On Market

    Current Estimated Value $1,367,857

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    823 Indies Rd, Ramrod Key, FL 33042
    • /2

      Est $1,016,359

      Not Listed For Sale

      29552 Independence Ave, Big Pine Key, FL 33043

      • 2 Beds
      • 2 Baths
      • 1,280 Sq Ft
      • Built 1976
      29552 Independence Ave, Big Pine Key, FL 33043

  • /12

    $599,000

    • Land
    • 11,950 Sq Ft
    • $2,183,468 per Acre

    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
  • /37

    $800,000

    Sold Dec 19, 2025

    923 Indies Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,079 Sq Ft
    • Built 2002

    Last Sold Summary

    • 6% Below List Price
    • $741/SF
    • 60 Days On Market

    Current Estimated Value $822,192

    Last Listing Agent Christina Davis Coldwell Banker Schmitt RE Co.

    923 Indies Rd, Summerland Key, FL 33042
    • /46

      Est $2,811,256

      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

      • 78 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /61

    $2,700,000

    $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,100 Sq Ft

    1553 Sunrise Dr, Big Pine Key, FL 33043

    Walk into this luxurious palace with captivating open water views. Light colors accenting the beautiful interior with matching large Porcelain floors and counter tops enhancing the large windows bringing the natural light inside. Gourmet kitchen for any chef to create great memories viewing the sunsets. Open patio with a great view of the pool and the outdoor entertaining areas. Four roomy suites

    1553 Sunrise Dr, Big Pine Key, FL 33043
  • /42

    $1,750,000

    Sold Feb 26, 2026

    20771 2nd Ave W, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 2,047 Sq Ft
    • Built 2010

    Last Sold Summary

    • 17% Below List Price
    • $855/SF
    • 161 Days On Market

    Current Estimated Value $1,771,553

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    20771 2nd Ave W, Summerland Key, FL 33042
    • /28

      Est $515,552

      Not Listed For Sale

      31124 Avenue E, Big Pine Key, FL 33043

      • 2 Beds
      • 1 Bath
      • 912 Sq Ft
      • Built 1963
      31124 Avenue E, Big Pine Key, FL 33043

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Derrick Johnson Coco Plum Real Estate

  • /73

    $2,999,000

    New Construction Open Sun 2PM - 4PM $301K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,886 Sq Ft

    23950 Overseas Hwy, Summerland Key, FL 33042

    Welcome to Pink Sands, a Glenn Gray-designed waterfront retreat where the vibrant colors and laid-back elegance of the Bahamas meet the timeless beauty of the Florida Keys. Recognizable by its signature pink façade and blue metal roof, this exceptional Summerland Key residence captures the spirit of island living while offering the quality, comfort, and peace of mind of modern CBS construction.

    TEAM Walters Gloria, Rachel and Michae Ocean Sotheby's International Realty

    23950 Overseas Hwy, Summerland Key, FL 33042
  • /48

    $935,000

    Sold Jun 08, 2026

    29175 Aster Ln, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 2019

    Last Sold Summary

    • 2% Below List Price
    • $812/SF
    • 8 Days On Market

    Current Estimated Value $929,062

    Last Listing Agent Scott Brisson KeyIsle Realty

    29175 Aster Ln, Big Pine Key, FL 33043
    • /2

      Est $1,060,712

      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

  • /27

    $1,950,000

    • 3 Beds
    • 3 Baths
    • 1,797 Sq Ft

    860 Lagoon Dr, Summerland Key, FL 33042

    This stately concrete home has all the best of everything on one of the best boating areas in the Lower KeysThís home is being offered completely furnished with electronics & most of the artwork, All kitchen and bedding items. The large great room has lots of seating. with soaring ceilings and lots of natural light. The kitchen is a chef's delight with sub zero appliances and induction chef's

    Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

    860 Lagoon Dr, Summerland Key, FL 33042
  • /43

    $815,000

    Sold Jan 23, 2026

    681 W Indies Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft
    • Built 1987

    Last Sold Summary

    • 18% Below List Price
    • $894/SF
    • 211 Days On Market

    Current Estimated Value $828,140

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    681 W Indies Dr, Summerland Key, FL 33042
    • /44

      Est $734,018

      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

      • 3 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /60

    $2,699,999

    • 4 Beds
    • 2.5 Baths
    • 2,452 Sq Ft

    20833 4th Ave W, Cudjoe Key, FL 33042

    Welcome to one of Cudjoe Gardens' most desirable waterfront addressesBuilt in 2018, 20833 4th Avenue West is an exceptional CBS waterfront estate offering 4 bedrooms, 3 bathrooms, and more than 2,400 square feet of thoughtfully designed living space. Perfectly positioned on an oversized waterfront lot, this home combines outstanding boating amenities, resort-style outdoor living, and

    Diane Corliss Coldwell Banker Schmitt RE Co.

    20833 4th Ave W, Cudjoe Key, FL 33042
  • /21

    $745,000

    Sold Aug 05, 2026

    9W Cooks, Cook Island Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 574 Sq Ft
    • Built 1988

    Last Sold Summary

    • 17% Below List Price
    • $1,298/SF
    • 80 Days On Market

    Current Estimated Value $752,000

    Last Listing Agent Greg Gordon The Island Collective Realty

    9W Cooks, Cook Island Key, FL 33043
    • /46

      Est $1,328,008

      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

      • 8 Days On Market

      Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  • /42

    $980,000

    $170K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,782 Sq Ft

    750 W Indies Dr, Summerland Key, FL 33042

    This three bedroom , two bathroom home sits on an expansive 12,200 square foot piece of property in the highly sought after Breezeswept Beach Estates neighborhood on Ramrod Key. Upstairs there are two bedrooms and one bath, and a large kitchen and living room. Downstairs is a one bedroom, one bathroom bungalow with a complete kitchen!The exterior of the property has several updates,

    Mary Conklin Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    750 W Indies Dr, Summerland Key, FL 33042
  • /39

    $940,000

    Sold Apr 13, 2026

    421 Ixora Dr, Big Pine Key, FL 33043

    • 2 Beds
    • 3 Baths
    • 1,120 Sq Ft
    • Built 1982

    Last Sold Summary

    • 6% Below List Price
    • $839/SF
    • 70 Days On Market

    Current Estimated Value $932,323

    Last Listing Agent Melissa Graham Internet Realty of the Florida Keys

    421 Ixora Dr, Big Pine Key, FL 33043
    • /2

      Est $913,429

      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

  • /56

    $1,400,000

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    1518 Sunrise Dr, Big Pine Key, FL 33043

    Discover your paradise in the heart of Big Pine Key! This beautifully maintained 3-bedroom 2-bath CBS, stilted home offers the perfect blend of Lower Keys Island charm and all the modern comforts. Step inside to find a bright, wide-open living space designed for relaxed Keys living and entertaining, with plenty of room for family & friends. Outside, your private backyard oasis awaits. Take a

    Paul Rogers Coldwell Banker Schmitt RE Co.

    1518 Sunrise Dr, Big Pine Key, FL 33043
  • /83

    $3,299,000

    Sold Jul 17, 2026

    17042 Starfish Ln W, Summerland Key, FL 33042

    • 6 Beds
    • 4.5 Baths
    • 3,700 Sq Ft
    • Built 1982

    Last Sold Summary

    • $892/SF
    • 3 Days On Market

    Current Estimated Value $3,216,125

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17042 Starfish Ln W, Summerland Key, FL 33042
    • /23

      Est $1,370,761

      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

      • 73 Days On Market

      Last Listing Agent Lee Sanders/Sunnie SanLorenzo KeyIsle Realty

  • /42

    $1,449,000

    New Construction Under Contract
    • 3 Beds
    • 3 Baths
    • 1,500 Sq Ft

    22872 Buccaneer Ln, Cudjoe Key, FL 33042

    *SWIMMING POOL BEING BUILT NOW! Construction process underway. *Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West!Tucked away in a quiet, peaceful neighborhood.Inside, the home features generous living space, providing ample room to stretch out and make it your own.

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    22872 Buccaneer Ln, Cudjoe Key, FL 33042
  • /24

    $360,000

    Sold Apr 27, 2026

    27735 Sea Whip St, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,032 Sq Ft
    • Built 1978

    Last Sold Summary

    • 16% Below List Price
    • $349/SF
    • 12 Days On Market

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    27735 Sea Whip St, Summerland Key, FL 33042
    • /115

      Est $6,772,577

      Not Listed For Sale

      785 Sawyer Dr, Cudjoe Key, FL 33042

      • 7 Beds
      • 6 Baths
      • 4,888 Sq Ft
      • Built 2019
      785 Sawyer Dr, Cudjoe Key, FL 33042

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

Showing Results 361 - 400, Page 10 of 18

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