8,633

Summerland Key, FL Homes

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  • /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 $933,341

    Last Listing Agent Scott Brisson KeyIsle Realty

    29175 Aster Ln, Big Pine Key, FL 33043
    • /22

      Est $786,393

      Not Listed For Sale

      29548 Enterprise Ave, Big Pine Key, FL 33043

      • 4 Beds
      • 4 Baths
      • 2,232 Sq Ft
      • Built 1974
      29548 Enterprise Ave, Big Pine Key, FL 33043

      Last Sold Summary

      • 523 Days On Market

  • /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
  • /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 $820,416

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    681 W Indies Dr, Summerland Key, FL 33042
    • /2

      Est $818,532

      Not Listed For Sale

      677 Heck Ave, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 875 Sq Ft
      • Built 1977
      677 Heck Ave, Summerland Key, FL 33042

  • /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
  • /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 $923,911

    Last Listing Agent Melissa Graham Internet Realty of the Florida Keys

    421 Ixora Dr, Big Pine Key, FL 33043
    • /19

      Est $1,031,401

      Not Listed For Sale

      825 Pirates Rd, Summerland Key, FL 33042

      • 4 Beds
      • 4 Baths
      • 1,920 Sq Ft
      • Built 1982
      825 Pirates Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 32 Days On Market

  • /32

    $995,000

    • 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 Action Keys Realty of the Lower FL Keys LLC

    29131 Watson Blvd, Big Pine Key, FL 33043
  • /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
    • /2

      Est $885,940

      Not Listed For Sale

      337 46th St, Summerland Key, FL 33042

      • 4 Beds
      • 3 Baths
      • 1,600 Sq Ft
      • Built 1958
      337 46th St, Summerland Key, FL 33042

  • /58

    $649,000

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

    31147 Avenue H, Big Pine Key, FL 33043

    Big Pine Key Pool Home - Nature Lover's Paradise! 3BR/2BA single-family home with pool, outdoor kitchen, and gazebo -- perfect for entertaining and enjoying the Florida Keys lifestyle! Located in beautiful Big Pine Key, this property offers an abundance of parking and is ideal for boating, guests, RVs, or multiple vehicles.Surrounded by the natural beauty of Big Pine Key and its famous Key

    Jamie Caudill Lokation Real Estate

    31147 Avenue H, Big Pine Key, FL 33043
  • /31

    $799,000

    Sold May 29, 2026

    31226 Hollerich Dr, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft
    • Built 1980

    Last Sold Summary

    • $768/SF
    • 11 Days On Market

    Current Estimated Value $797,421

    Last Listing Agent Wyatt Tucker Expert Realty LLC (HQ)

    31226 Hollerich Dr, Big Pine Key, FL 33043
    • /15

      Est $197,659

      Not Listed For Sale

      29859 Overseas Hwy Unit 54, Big Pine Key, FL 33043

      29859 Overseas Hwy Unit 54, Big Pine Key, FL 33043

      Last Sold Summary

      • 13 Days On Market

  • /51

    $1,599,900

    $75K PRICE DROP
    • 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 living room

    Bobby Coe RE/MAX Keys Connection (KW)

    559 Powell Ave, Little Torch Key, FL 33042
  • /96

    $1,575,000

    Sold Mar 23, 2026

    17176 Bonita Ln W, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,353 Sq Ft
    • Built 1974

    Last Sold Summary

    • 7% Below List Price
    • $669/SF
    • 63 Days On Market

    Current Estimated Value $1,656,103

    Last Listing Agent Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

    17176 Bonita Ln W, Summerland Key, FL 33042
    • /35

      Est $997,498

      Not Listed For Sale

      346 Blackbeard Rd, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,188 Sq Ft
      • Built 1996
      346 Blackbeard Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 62 Days On Market

  • /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
  • /40

    $1,050,000

    Sold Jan 12, 2026

    32734 Bimini Ln, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,654 Sq Ft
    • Built 1995

    Last Sold Summary

    • 14% Below List Price
    • $635/SF
    • 235 Days On Market

    Current Estimated Value $1,112,534

    Last Listing Agent Ally Kelley Ocean Sotheby's International

    32734 Bimini Ln, Big Pine Key, FL 33043
    • /2

      Est $698,392

      Not Listed For Sale

      30827 Baileys Ln, Big Pine Key, FL 33043

      • 2 Beds
      • 2 Baths
      • 998 Sq Ft
      • Built 1980
      30827 Baileys Ln, Big Pine Key, FL 33043

  • /73

    $3,300,000

    New Construction
    • 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
  • /30

    $440,000

    Sold Apr 30, 2026

    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

    • 2 Beds
    • 1.5 Baths
    • 604 Sq Ft
    • Built 1976

    Last Sold Summary

    • 9% Below List Price
    • $728/SF
    • 170 Days On Market

    Last Listing Agent Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
    • /2

      Est $591,810

      Not Listed For Sale

      30323 Poinciana Rd, Big Pine Key, FL 33043

      • 5 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1971
      30323 Poinciana Rd, 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
  • /2

    $1,400,000

    Sold Sep 17, 2025

    491 W Indies Dr, Ramrod Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 2020

    Last Sold Summary

    • $1,163/SF
    • 0 Days On Market

    Current Estimated Value $1,412,669

    Last Listing Agent Mark Gable Engel & Volkers Marathon

    491 W Indies Dr, Ramrod Key, FL 33042
    • /2

      Est $3,619,556

      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

  • /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
  • /10

    $100,000

    Sold Apr 17, 2026

    BK 24 LT 2 Pandorea Ln, Big Pine Key, FL 33043

    • Land
    • 8,276 Sq Ft
    • $526,316 per Acre

    Last Sold Summary

    • 8 Days On Market

    Last Listing Agent Vanessa J. Chamizo, Professional Agent Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

    BK 24 LT 2 Pandorea Ln, Big Pine Key, FL 33043
    • /3

      Est $1,135,890

      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

  • /42

    $995,000

    $155K 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, including

    Mary Conklin Action Keys Realty of the Lower FL Keys LLC

    750 W Indies Dr, Summerland Key, FL 33042
  • /9

    $175,000

    Sold Apr 06, 2026

    Vacant Picard Ln, Cudjoe Key, FL 33042

    • Land
    • 6,000 Sq Ft
    • $1,270,500 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 219 Days On Market

    Last Listing Agent Lee Sanders/Sunnie SanLorenzo KeyIsle Realty

    Vacant Picard Ln, Cudjoe Key, FL 33042
    • /38

      Est $926,038

      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

  • /42

    $1,449,000

    New Construction Open Wed 12PM - 2PM
    • 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. Indoor-outdoor living

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    22872 Buccaneer Ln, Cudjoe Key, FL 33042
  • /30

    $430,000

    Sold May 11, 2026

    21857 Disturbed Pine Rd, Summerland Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 415 Sq Ft
    • Built 1975

    Last Sold Summary

    • $1,036/SF
    • 94 Days On Market

    Current Estimated Value $453,211

    Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

    21857 Disturbed Pine Rd, Summerland Key, FL 33042
    • /55

      Est $1,427,944

      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

  • /3

    $284,999

    $104K PRICE DROP
    • Land
    • 23,958 Sq Ft
    • $518,180 per Acre

    0 Sunset Blvd Unit MFRA4697420, Summerland Key, FL 33042

    Beautiful .55 acre lot in Summerland Key, FL. Summerland Key is a unique fly-in community with a private airstrip and marina close by. SUMMERLAND ESTATES SUMMERLAND KEY PB2-167 PT LT 25 (LOT A 90 FT X 264.75 FT). Buyer is responsible for conducting due diligence on the property prior to purchase.

    Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

    0 Sunset Blvd Unit MFRA4697420, Summerland Key, FL 33042
  • /23

    $710,000

    Sold Aug 20, 2025

    19603 Seminole St, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Built 2014

    Last Sold Summary

    • 3% Below List Price
    • $598/SF
    • 5 Days On Market

    Current Estimated Value $735,565

    Last Listing Agent Steven Koleno Beycome of Florida, LLC

    19603 Seminole St, Summerland Key, FL 33042
    • /37

      Est $1,773,608

      Not Listed For Sale

      1008 Buttonwood Dr E, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 2008
      1008 Buttonwood Dr E, Summerland Key, FL 33042

      Last Sold Summary

      • 42 Days On Market

  • /40

    $894,000

    $31K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,034 Sq Ft

    28571 Buccaneer Rd, Summerland Key, FL 33042

    Embrace the ultimate Keys lifestyle in this charming waterfront hone, where every day feels like a vacation. Located just minutes from ocean access no bridges, this property is a fisherman's paradiseThis 3-bedroom, 2-bath home offers Hardie board Siding metal roof an open floor plan. The newly updated kitchen features exquisite granite countertops, stainless steel appliances, and a large

    Diane Corliss Coldwell Banker Schmitt RE Co.

    28571 Buccaneer Rd, Summerland Key, FL 33042
  • /30

    $628,000

    Sold Sep 05, 2025

    31256 Avenue H, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft
    • Built 2005

    Last Sold Summary

    • 4% Below List Price
    • $549/SF
    • 106 Days On Market

    Current Estimated Value $639,349

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    31256 Avenue H, Big Pine Key, FL 33043

Showing Results 361 - 400, Page 10 of 18

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