8,633

Summerland Key, FL Homes

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  • /48

    $291,000

    Sold Mar 03, 2026

    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1985

    Last Sold Summary

    • 9% Below List Price
    • $404/SF
    • 133 Days On Market

    Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
    • /9

      Not Listed For Sale

      22819 Blackbeard Ln, Cudjoe Key, FL 33042

      22819 Blackbeard Ln, Cudjoe Key, FL 33042

      Last Sold Summary

      • 543 Days On Market

  • /29

    $775,000

    $25K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,162 Sq Ft

    28452 Yucatan Ln, Summerland Key, FL 33042

    Must be sold after Jan 1, 2027. Canal front home with quick exit out of the canal to Pine Channel for Atlantic or Gulf access. 7200 sq.ft. lot. Back yard big enough for a pool. Pack your toothbrush and your ready for your salt life to begin. Being sold mostly furnished 2bd/2bth 1162 sq.ft. Home, plus, southerly facing screen porch, which has accordian shutters,porch faces back yard and canal.

    Rose Dell Keller Williams Key West Compass Realty

    28452 Yucatan Ln, Summerland Key, FL 33042
  • /47

    $1,282,000

    Sold Nov 12, 2025

    29436 Independence Ave, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $855/SF
    • 82 Days On Market

    Current Estimated Value $1,289,959

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    29436 Independence Ave, Big Pine Key, FL 33043
    • /2

      Not Listed For Sale

      30919 Edward Rd Unit A & B, Big Pine Key, FL 33043

      • 3 Beds
      • 2 Baths
      • 1,170 Sq Ft
      • Built 1943
      30919 Edward Rd Unit A & B, Big Pine Key, FL 33043

  • /21

    $430,000

    $35K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 799 Sq Ft

    701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042

    A place to live, winter or Airbnb. Daily rentals allowed. Waterfront view down the canal. 17 ft seawall. Covered back patio for grilling or lounging. Front covered balcony. and back covered patio deck with mini sink, mini fridge & mini freezer. 1993' Manufactured home with Florida Room totaling 799 sq. ft. approx. 1 Bedroom w/a bonus room. Updated Bathroom with walk in shower, glass doors, hand

    Rose Dell Keller Williams Key West Compass Realty

    701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042
  • /43

    $1,410,000

    Sold Apr 30, 2026

    17152 Marlin Dr, Sugarloaf Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1989

    Last Sold Summary

    • 12% Below List Price
    • $1,175/SF
    • 70 Days On Market

    Current Estimated Value $1,428,779

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17152 Marlin Dr, Sugarloaf Key, FL 33042
    • /2

      Not Listed For Sale

      430 Les Rohde Dr, Ramrod Key, FL 33042

      430 Les Rohde Dr, Ramrod Key, FL 33042

  • /46

    $1,599,000

    Under Contract
    • 2 Beds
    • 3 Baths
    • 1,244 Sq Ft

    2237 San Remo Dr, Big Pine Key, FL 33043

    The Angler's Retreat -- Big Pine Key Resort-style canal front living beneath a majestic Banyan.Some places don't just change your pace -- they change your life. Tucked within the protected beauty of the National Key Deer Refuge on Doctors Arm, this fully reimagined waterfront estate sits on half an acre of lush, private grounds where a resident family of Key deer wander freely and the outside

    Suzanne Moore Suzanne Moore Real Estate

    2237 San Remo Dr, Big Pine Key, FL 33043
  • /2

    $255,000

    Sold Oct 20, 2025

    150 Coral Ave, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Built 1993

    Last Sold Summary

    • $232/SF
    • 0 Days On Market

    Current Estimated Value $652,631

    Last Listing Agent User Kristen Brenner/Margie Casey T Florida Keys Real Estate Group

    150 Coral Ave, Summerland Key, FL 33042
    • /2

      Est $542,521

      Not Listed For Sale

      20874 4th Ave, Cudjoe Key, FL 33042

      • Studio
      20874 4th Ave, Cudjoe Key, FL 33042

  • /36

    $750,000

    • Land
    • 9.25 Acres
    • $81,081 per Acre

    0 Niles Rd Unit MLS A11925960, Summerland Key, FL 33042

    Discover the perfect opportunity to build your dream home in the Lower Keys on this desirable parcel located on Summerland Key, FL. Set within a peaceful residential neighborhood, this property offers an inviting blend of tranquility and convenience—just minutes from US-1, local marinas, boat ramps, dining, beaches, and world-class fishing. Enjoy the relaxed island lifestyle, tropical breezes,

    Javier Santana Sunland Real Estate, LLC.

    0 Niles Rd Unit MLS A11925960, Summerland Key, FL 33042
  • /3

    $325,000

    Sold Oct 09, 2025

    29153 Tulip Ln, Big Pine Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1984

    Last Sold Summary

    • $356/SF
    • 0 Days On Market

    Current Estimated Value $383,171

    Last Listing Agent Ryan Gernaat Coldwell Banker Schmitt Lower Keys (KW)

    29153 Tulip Ln, Big Pine Key, FL 33043
    • /2

      Not Listed For Sale

      1138 Basque Ln, Summerland Key, FL 33042

      • 7,000 Sq Ft
      1138 Basque Ln, Summerland Key, FL 33042

  • /59

    $3,750,000

    • 4 Beds
    • 3.5 Baths
    • 2,409 Sq Ft

    17387 E Dolphin St, Sugarloaf Key, FL 33042

    Welcome to Morning Glory - The Dolphin House, a rare direct oceanfront retreat in the Florida Keys. Situated on an oversized oceanfront lot, this 4BR/3.5BA home offers 2,478 SqFt of coastal elegance, breathtaking Atlantic views, and the peaceful lifestyle buyers dream about. Wake up to stunning sunrises, relax by the pool beneath swaying palms, enjoy waterfront dining with guests and friends, or

    17387 E Dolphin St, Sugarloaf Key, FL 33042
  • /51

    $420,000

    Sold Nov 21, 2025

    701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 816 Sq Ft
    • Built 1979

    Last Sold Summary

    • 8% Below List Price
    • $515/SF
    • 185 Days On Market

    Last Listing Agent Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
    • /61

      Est $2,864,337

      Not Listed For Sale

      20886 4th Ave W, Summerland Key, FL 33042

      • 4 Beds
      • 3 Baths
      • 3,042 Sq Ft
      • Built 2008
      20886 4th Ave W, Summerland Key, FL 33042

      Last Sold Summary

      • 66 Days On Market

  • /68

    $879,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042

    This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042
  • /84

    $1,600,000

    Sold Apr 09, 2026

    17125 Wahoo Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • Built 1982

    Last Sold Summary

    • $971/SF
    • 8 Days On Market

    Current Estimated Value $1,570,095

    Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

    17125 Wahoo Ln, Summerland Key, FL 33042
    • /2

      Est $258,322

      Not Listed For Sale

      31380 Ave G, Big Pine Key, FL 33043

      • 2 Beds
      • 2 Baths
      • 1,104 Sq Ft
      • Built 1971
      31380 Ave G, Big Pine Key, FL 33043

  • /41

    $800,000

    Under Contract
    • Land
    • 20 Acres
    • $40,000 per Acre

    33000 Old State Road 4a, No Name Key, FL 33043

    YOU CAN HELP SAVE THE FLORIDA KEYS REEFS..!! THIS 20 ACRE PARCEL WITH A 17 ACRE SALTWATER LAKE WAS RECENTLY MARKETED AS A PRIVATE LAKE FOR PERSONAL USE. IT MAY STILL BE USED FOR THAT. THIS PROPERTY CANNOT BE DEVELOPED...!!!! NO HOME, NO COMMERCIAL USE. HOWEVER IN RECENT MONTHS RESEARCHERS FROM FLORIDA INTERNATIONAL UNIVERSITY HAVE BEEN STUDYING THE GROWTH OF SPIDER CRABS THAT THRIVE ON ALGAE. THE

    Tony Paterniti Tony Paterniti

    33000 Old State Road 4a, No Name Key, FL 33043
  • /4

    $50,000

    Sold Dec 19, 2025

    0 Old State Rd Unit 616986, Cudjoe Key, FL 33042

    • Land
    • 7,450 Sq Ft
    • $292,349 per Acre

    Last Sold Summary

    • 41% Below List Price
    • 25 Days On Market

    Last Listing Agent Sabre Mendoza Coldwell Banker Schmitt RE Co.

    0 Old State Rd Unit 616986, Cudjoe Key, FL 33042
    • /6

      Not Listed For Sale

      31450 Avenue C, Big Pine Key, FL 33043

      • 2 Beds
      • 1 Bath
      • 480 Sq Ft
      • Built 1963
      31450 Avenue C, Big Pine Key, FL 33043

      Last Sold Summary

      • 19 Days On Market

  • /35

    $530,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,184 Sq Ft

    27967 Coral Shores Rd, Little Torch Key, FL 33042

    Canal-front living at its finest! This beautifully remodeled 2-bedroom, 2-bath home is truly a must-see. Step inside to discover a bright and inviting interior featuring new flooring, an updated kitchen, and stylishly renovated bathrooms. The home is enhanced with numerous impact windows, filling the space with natural light and added peace of mind.Relax and unwind on the screened patio, or

    Diane Corliss Coldwell Banker Schmitt RE Co.

    27967 Coral Shores Rd, Little Torch Key, FL 33042
  • /2

    $50,000

    Sold Nov 11, 2025

    Lot P No Name Key, No Name Key, FL 33043

    • Land
    • 21,780 Sq Ft
    • $100,000 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 55 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot P No Name Key, No Name Key, FL 33043
    • /107

      Est $5,033,269

      Not Listed For Sale

      220 E Caribbean Dr, Summerland Key, FL 33042

      • 5 Beds
      • 7 Baths
      • 4,981 Sq Ft
      • Built 2025
      220 E Caribbean Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 165 Days On Market

  • /4

    $1,050,000

    • 3 Beds
    • 2.5 Baths
    • 1,954 Sq Ft

    27403 Antigua Ln, Summerland Key, FL 33042

    Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly found in the Keys. The elevated concrete home features a spacious layout, multiple balconies, and abundant natural light

    Sonia Petraitis Caffroni Capital Intl Realty LLC

    27403 Antigua Ln, Summerland Key, FL 33042
  • /39

    $705,000

    Sold Sep 08, 2025

    181 Doubloon Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,090 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Above List Price
    • $647/SF
    • 7 Days On Market

    Current Estimated Value $768,255

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    181 Doubloon Ln, Summerland Key, FL 33042
    • /29

      Not Listed For Sale

      28131 Helen Ave, Little Torch Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 856 Sq Ft
      • Built 1972
      28131 Helen Ave, Little Torch Key, FL 33042

      Last Sold Summary

      • 91 Days On Market

  • /28

    $740,000

    $98K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    3856 Donna Rd, Big Pine Key, FL 33043

    48k Price Improvement from original Listing, Priced to SELL, Motivated Seller, Bring all Offers. Sportsman Paradise. 2 Bedroom House with Permitted Concrete BOAT RAMP, concrete sea wall, concrete fish cleaning table with Permitted downstairs bathroom. Real short idle to open water. Back country fishing, lobster diving/snorkel and stone crabs right in your back yard. Easy access to to Atlantic &

    Alan Ballas Alan Ballas Realty

    3856 Donna Rd, Big Pine Key, FL 33043
  • /5

    $235,000

    Sold Sep 09, 2025

    1388 Avenue B, Big Pine Key, FL 33043

    • Land
    • 7,500 Sq Ft
    • $1,364,880 per Acre

    Last Sold Summary

    • 33% Below List Price
    • 212 Days On Market

    Current Estimated Value $248,086

    Last Listing Agent Sarah Dolson Keller Williams Key West Compass Realty

    1388 Avenue B, Big Pine Key, FL 33043
    • /2

      Est $244,109

      Not Listed For Sale

      27328 St Vincent Ln, Ramrod Key, FL 33042

      • Studio
      27328 St Vincent Ln, Ramrod Key, FL 33042

  • /20

    $550,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    27910 Porgie Path, Summerland Key, FL 33042

    Great chance to own waterfront paradise with this elevated double-wide home situated on a rare double lot. Corner lot allows you to enjoy water on two sides of the property (plugged canals) —perfect for swimming, kayaking, paddle boarding, and relaxing by the water. Tucked away on a quiet cul-de-sac with lovely views, this property offers both privacy and charm, enhanced by mature landscaping.

    Alexis Seldin Xcellence

    27910 Porgie Path, Summerland Key, FL 33042
  • /42

    $550,000

    Sold Dec 01, 2025

    27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042

    • 4 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 1984

    Last Sold Summary

    • 19% Below List Price
    • $637/SF
    • 125 Days On Market

    Current Estimated Value $605,856

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

    27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042
    • /49

      Est $302,405

      Not Listed For Sale

      701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

      Last Sold Summary

      • 27 Days On Market

  • /64

    $1,480,000

    New Construction $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,120 Sq Ft

    27433 Antigua Rd, Summerland Key, FL 33042

    NEW CONSTRUCTION POOL HOME - COMPLETED 2025 & MOVE-IN READY!Welcome to your brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and impact-rated windows &

    Kelly Gardner Bluescape Real Estate

    27433 Antigua Rd, Summerland Key, FL 33042
  • /33

    $1,075,000

    Sold Feb 20, 2026

    17226 Jamaica Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1998

    Last Sold Summary

    • 10% Below List Price
    • $861/SF
    • 32 Days On Market

    Current Estimated Value $1,103,834

    Last Listing Agent Stephen Hachey

    17226 Jamaica Ln, Summerland Key, FL 33042
    • /2

      Est $1,069,933

      Not Listed For Sale

      783 Pirates Rd, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,188 Sq Ft
      • Built 2017
      783 Pirates Rd, Summerland Key, FL 33042

  • /25

    $615,000

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    31243 E Ave E, Big Pine Key, FL 33043

    **Price Improvement** Welcome to your slice of paradise in Big Pine Key! This charming 3-bedroom, 2-bath home is an ideal opportunity for families or first-time homebuyers seeking the quintessential Florida Keys lifestyle. Step inside to discover a comfortable and inviting living space, perfect for creating lasting memories. Outside, a small, fenced area provides a safe and convenient space for

    Sabre Mendoza Coldwell Banker Schmitt RE Co.

    31243 E Ave E, Big Pine Key, FL 33043
  • /42

    $635,000

    Sold Feb 19, 2026

    3231 Pompano St, Big Pine Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1985

    Last Sold Summary

    • 2% Below List Price
    • $735/SF
    • 6 Days On Market

    Current Estimated Value $634,523

    Last Listing Agent Dawn McComish Lokation Real Estate

    3231 Pompano St, Big Pine Key, FL 33043

Showing Results 241 - 280, Page 7 of 18

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