8,476

Summerland Key, FL Homes

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  • /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
  • /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
    • /2

      Not Listed For Sale

      29527 Constitution Ave, Big Pine Key, FL 33043

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1982
      29527 Constitution Ave, 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
  • /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 $1,560,242

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

    17125 Wahoo Ln, Summerland Key, FL 33042
    • /31

      Est $944,110

      Not Listed For Sale

      27373 Antigua Ln, Ramrod Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,188 Sq Ft
      • Built 2016
      27373 Antigua Ln, Ramrod Key, FL 33042

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Sandra Dolowy KeyIsle Realty

  • /35

    $530,000

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

    27967 Coral Shores Rd, Little Torch Key, FL 33042

    Experience relaxed Florida Keys living in this beautifully remodeled 2-bedroom, 2-bath canal-front home. The bright, welcoming interior features new flooring, an updated kitchen, and stylishly renovated bathrooms, creating a fresh and comfortable space ready to enjoy.Numerous impact windows fill the home with natural light while offering added protection and peace of mind. Step outside to the

    Diane Corliss Coldwell Banker Schmitt RE Co.

    27967 Coral Shores Rd, Little Torch Key, FL 33042
  • /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
    • /9

      Est $358,937

      Not Listed For Sale

      31456 Ave F, Big Pine Key, FL 33043

      • 2 Beds
      • Built 1972
      31456 Ave F, Big Pine Key, FL 33043

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Kirksten Irick Preferred Properties (KW)

  • /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
  • /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
    • /2

      Est $843,058

      Not Listed For Sale

      53 Gold Boullion Rd, Cudjoe Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2016
      53 Gold Boullion Rd, Cudjoe Key, FL 33042

  • /28

    $710,000

    $128K 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
  • /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 $749,570

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    181 Doubloon Ln, Summerland Key, FL 33042
    • /69

      Not Listed For Sale

      701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

      • 1 Bed
      • 1 Bath
      • 420 Sq Ft
      • Built 1988
      701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

      Last Sold Summary

      • 461 Days On Market

      Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.

  • /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
  • /88

    $2,750,000

    Sold Jul 28, 2026

    1044 Lagoon Dr, Summerland Key, FL 33042

    • 4 Beds
    • 2 Baths
    • 1,917 Sq Ft
    • Built 1979

    Last Sold Summary

    • 5% Below List Price
    • $1,435/SF
    • 2 Days On Market

    Current Estimated Value $2,360,411

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    1044 Lagoon Dr, Summerland Key, FL 33042
    • /14

      Est $434,000

      Not Listed For Sale

      29167 Cactus Ln, Big Pine Key, FL 33043

      29167 Cactus Ln, Big Pine Key, FL 33043

      Last Sold Summary

      • 121 Days On Market

      Last Listing Agent Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  • /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
  • /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 $425,333

      Not Listed For Sale

      Lot 2 Egret Ln, Big Pine Key, FL 33043

      • Studio
      Lot 2 Egret Ln, Big Pine Key, FL 33043

  • /2

    $54,000

    $6K PRICE DROP
    • Land

    0 Bk 4 Lt 9 Pine Crest Rd Unit 618082, Big Pine Key, FL 33043

    ROGO lot worth 2 points for DEDICATION purposes. Seller has county ROGO Letter of Land Dedication verifying lot is eligible for land dedication/2 points. Want to build quicker? This is a path. Buyer to verify points and process with Monroe County. See Documents tab for letter.

    Donna Pezzi Keller Williams Key West Compass Realty

    0 Bk 4 Lt 9 Pine Crest Rd Unit 618082, Big Pine Key, FL 33043
  • /24

    $1,000,000

    Sold Aug 21, 2026

    1331 Hudgins Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,023 Sq Ft
    • Built 1983

    Last Sold Summary

    • 13% Below List Price
    • $978/SF
    • 195 Days On Market

    Current Estimated Value $1,061,825

    Last Listing Agent Camilo Perez Home Sold Realty, LLC

    1331 Hudgins Dr, Summerland Key, FL 33042
    • /47

      Not Listed For Sale

      701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

      • 1 Bed
      • 1 Bath
      • 520 Sq Ft
      • Built 2000
      701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

      Last Sold Summary

      • 194 Days On Market

      Last Listing Agent Anne Press Lokation Real Estate

  • /51

    $1,250,000

    • 1 Bed
    • 3 Baths
    • 1,234 Sq Ft

    27001 Overseas Hwy, Ramrod Key, FL 33042

    Prime Lower Keys Commercial Property for sale on Ramrod Key. 3 Lots total 28,132 sf. or .65 acres with nearly 189' of frontage on Overseas Hwy aka Jimmy Buffett Memorial Hwy.!! Excellent visibility from the highway going both North and Southbound. This is a Corner lot at Coral Ave and Overseas Hwy with additional rear access off Old State Rd. 4A. Three sides with roads give this property ample

    Bobby Coe RE/MAX Keys Connection (KW)

    27001 Overseas Hwy, Ramrod 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 $577,783

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

    27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042
    • /46

      Est $1,896,703

      Not Listed For Sale

      271 W Indies Dr, Ramrod Key, FL 33042

      • 4 Beds
      • 3.5 Baths
      • 2,358 Sq Ft
      • Built 2023
      271 W Indies Dr, Ramrod Key, FL 33042

      Last Sold Summary

      • 342 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /17

    $255,000

    $10K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $5,100,000 per Acre

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

    Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out—golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 643, Cudjoe 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 $1,100,713

    Last Listing Agent Stephen Hachey Flat Fee MLS Realty

    17226 Jamaica Ln, Summerland Key, FL 33042
    • /35

      Not Listed For Sale

      701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 849 Sq Ft
      • Built 1992
      701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

      Last Sold Summary

      • 191 Days On Market

  • /22

    $535,000

    $16K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    96 John St Unit 2, Summerland Key, FL 33042

    Well-maintained 3-bedroom, 2-bath home offering 1,120 square feet of comfortable living space in a small, well-kept community in Summerland Key. This home is in excellent condition, offers ample parking, and provides a wonderful opportunity for affordable homeownership in the Lower Keys. Subject to affordable housing deed restrictions.

    Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

    96 John St Unit 2, Summerland Key, FL 33042
  • /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 $635,454

    Last Listing Agent Dawn McComish Lokation Real Estate

    3231 Pompano St, Big Pine Key, FL 33043
    • /58

      Est $1,817,028

      Not Listed For Sale

      1106 Thatch Ln, Summerland Key, FL 33042

      • 4 Beds
      • 3.5 Baths
      • 2,548 Sq Ft
      • Built 2016
      1106 Thatch Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real E

  • /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.

    27910 Porgie Path, Summerland Key, FL 33042
  • /17

    $395,000

    Sold Sep 22, 2025

    10W Cooks Unit B, Cook Island Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 596 Sq Ft
    • Built 1948

    Last Sold Summary

    • 12% Below List Price
    • $663/SF
    • 13 Days On Market

    Current Estimated Value $425,000

    Last Listing Agent Greg Gordon Island Home Realty Inc.

    10W Cooks Unit B, Cook Island Key, FL 33043
    • /6

      Not Listed For Sale

      Lot 27 Angelfish Rd, Ramrod Key, FL 33042

      Lot 27 Angelfish Rd, Ramrod Key, FL 33042

      Last Sold Summary

      • 291 Days On Market

      Last Listing Agent Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  • /26

    $989,000

    • 3 Beds
    • 2 Baths
    • 1,329 Sq Ft

    673 Indies Rd, Summerland Key, FL 33042

    Elevated Coastal Living in Breezeswept Beach Estates. Skip the typical vacation rentals & step into a home designed specifically for the genuine Florida Keys lifestyle. Situated on a quiet street within Breezeswept Beach Estates, this well-maintained 3-bedroom, 2-bathroom stilt home perfectly balances premier boating access with a peaceful, scenic setting. The property's positioning is truly

    Gregory Sullivan BYOWNER.COM

    673 Indies Rd, Summerland Key, FL 33042
  • /60

    $2,512,500

    Sold Oct 31, 2025

    1260 Sugarloaf Blvd, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,886 Sq Ft
    • Built 1991

    Last Sold Summary

    • 3% Below List Price
    • $871/SF
    • 60 Days On Market

    Current Estimated Value $2,448,936

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    1260 Sugarloaf Blvd, Summerland Key, FL 33042
    • /30

      Est $823,470

      Not Listed For Sale

      124 Yardarm Rd, Cudjoe Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,064 Sq Ft
      • Built 2023
      124 Yardarm Rd, Cudjoe Key, FL 33042

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent The Spottswood Team Truman & Co. (KW)

  • /58

    $267,000

    $28K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042

    $21,000+ Gross Rental Revenue so far in 2026!Welcome to Conch Hideaway #423, a charming and income-producing tropical retreat located within the highly sought-after gated community of Venture Out in the Lower Florida Keys. This 1-bedroom, 1-bath island getaway offers the perfect blend of relaxed coastal living and strong investment potential.Currently operating as a successful vacation

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042

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