8,633

Summerland Key, FL Homes

Section Image
  • /40

    $1,115,000

    Sold Sep 10, 2025

    28552 Maracaibo Rd, Little Torch Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 988 Sq Ft
    • Built 1989

    Last Sold Summary

    • 3% Below List Price
    • $1,129/SF
    • 8 Days On Market

    Current Estimated Value $1,148,414

    Last Listing Agent Teri Hiller Coldwell Banker Schmitt Real Estate Co.

    28552 Maracaibo Rd, Little Torch Key, FL 33042
    • /2

      Est $1,405,979

      Not Listed For Sale

      27362 Anguila Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,842 Sq Ft
      • Built 1975
      27362 Anguila Ln, Summerland Key, FL 33042

  • /50

    $3,495,000

    • 4 Beds
    • 3.5 Baths
    • 2,766 Sq Ft

    414 Caribbean Dr E, Summerland Key, FL 33042

    OCEANFRONT , POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, just 30 minutes from Key West. Designed for serious boaters and lovers of open water, this premier deep-water home offers breathtaking Atlantic views, immediate boating access, and the ultimate Florida Keys lifestyle. Beautiful

    Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

    414 Caribbean Dr E, Summerland Key, FL 33042
  • /49

    $950,000

    Sold Apr 27, 2026

    29559 Ranger Ave, Big Pine Key, FL 33043

    • 2 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Built 1984

    Last Sold Summary

    • 25% Below List Price
    • $792/SF
    • 499 Days On Market

    Current Estimated Value $948,249

    Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

    29559 Ranger Ave, Big Pine Key, FL 33043
    • /12

      Est $711,622

      Not Listed For Sale

      27007 Angelfish Rd, Summerland Key, FL 33042

      • 2 Beds
      • 1,201 Sq Ft
      • Built 1967
      27007 Angelfish Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 281 Days On Market

  • /9

    $225,000

    • Land
    • 7,405 Sq Ft
    • $1,323,529 per Acre

    26837 Overseas Hwy, Summerland Key, FL 33042

    Rare opportunity to acquire a commercially zoned, vacant land parcel, fronting on U.S. Highway 1 in Ramrod Key, Florida. The subject property is 7,340 square foot vacant parcel with 50 feet of direct Overseas Highway frontage. Zoned Suburban Commercial (SC) under the Monroe County Land Development Code.

    Casey Prindle Nicklaus Vance

    26837 Overseas Hwy, Summerland Key, FL 33042
  • /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
    • /34

      Est $957,407

      Not Listed For Sale

      320 Spanish Main Dr, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1989
      320 Spanish Main Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 18 Days On Market

  • /55

    $3,025,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,288 Sq Ft

    17210 Angelfish Ln Unit + 17220, Summerland Key, FL 33042

    A rare double-parcel waterfront opportunity in Lower Sugarloaf Key - offering a newly constructed home plus an adjacent buildable lot, creating the ultimate private boating compound.The newly built 3BD/2.5BA residence with an office/den & laundry/utility room spans 2,288sf on a 16,445sf lot and is thoughtfully designed with an open-concept layout, abundant natural light, and sweeping water

    The Spottswood Team Truman & Co. (KW)

    17210 Angelfish Ln Unit + 17220, Summerland Key, FL 33042
  • /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 $786,336

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    1590 Gardenia Ln, Big Pine Key, FL 33043
    • /37

      Est $933,974

      Not Listed For Sale

      139 Le Grand Ln, Summerland Key, FL 33042

      • 3 Beds
      • 1 Bath
      • 1,300 Sq Ft
      • Built 1994
      139 Le Grand Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 48 Days On Market

  • /99

    $4,995,000

    • 3 Beds
    • 3 Baths
    • 4,687 Sq Ft

    3742 Seagrape St, Big Pine Key, FL 33043

    Escape to ''The Castle'', a luxurious gated Gulf-front estate rarely spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a graceful blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected canal-front dockage featuring a 15,000 lb

    Ally Kelley Ocean Sotheby's International

    3742 Seagrape St, Big Pine Key, FL 33043
  • /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 $819,515

    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
    • /27

      Est $1,658,196

      Not Listed For Sale

      22836 Port Royal Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,406 Sq Ft
      • Built 1987
      22836 Port Royal Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 6 Days On Market

  • /19

    $430,000

    $45K PRICE DROP
    • Land
    • 2,078 Sq Ft
    • $9,013,859 per Acre

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

    Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 551, 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 $2,506,761

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

    943 Flagship Dr, Summerland Key, FL 33042
    • /37

      Est $1,070,241

      Not Listed For Sale

      81 Coral Ave, Summerland Key, FL 33042

      • 2 Beds
      • 3 Baths
      • 1,535 Sq Ft
      • Built 1988
      81 Coral Ave, Summerland Key, FL 33042

      Last Sold Summary

      • 13 Days On Market

  • /13

    $450,000

    $92K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $2,812,500 per Acre

    1147 Basque Ln, Cudjoe Key, FL 33042

    BUILDING & DOCK PERMITS IN HAND for this Buildable Vacant Lot! This proposed engineered house is a large 2,132 Sq Ft 2 story plus 1,066 w/ potential parking & storage below at ground level. Current design and engineering calls for 4 Bedrooms 3.5 Baths with 4 Exterior Balcony/Decks providing approximately 450 Sq Ft of additional space for Open Water Views plus the house will also have Open Water

    Brad Baker Key to the Keys Real Estate, Inc

    1147 Basque Ln, Cudjoe Key, FL 33042
  • /6

    $1,400,000

    Sold May 28, 2026

    17195 Hibiscus Ln W, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1987

    Last Sold Summary

    • $1,080/SF
    • 0 Days On Market

    Current Estimated Value $1,214,236

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17195 Hibiscus Ln W, Summerland Key, FL 33042
    • /34

      Est $804,796

      Not Listed For Sale

      28551 Buccaneer Rd, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 841 Sq Ft
      • Built 1976
      28551 Buccaneer Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 48 Days On Market

  • /13

    $5,357

    • 2 Beds
    • 2.5 Baths
    • 1,080 Sq Ft

    28513 Channel View Dr, Little Torch Key, FL 33042

    This is a waterfront 3 story, 2 bedroom, 2.5 bathroom unfurnished or furnished townhome for rent on a year lease. It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, full size front load stackable washer and dryer, tile floors, hurricane windows and doors, 3 balconies, 2 heated community pools, 24 hour

    Joseph Danieli AKT Realty LLC

    28513 Channel View Dr, Little Torch Key, FL 33042
  • /3

    $65,000

    Sold Aug 04, 2025

    0 Spanish Channel Dr, No Name Key, FL 33043

    • Land
    • 8,510 Sq Ft
    • $332,714 per Acre

    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
    • /45

      Est $2,058,287

      Not Listed For Sale

      20942 6th Ave W, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 2,772 Sq Ft
      • Built 1994
      20942 6th Ave W, Summerland Key, FL 33042

      Last Sold Summary

      • 42 Days On Market

  • /18

    $799,000

    • 3 Beds
    • 1 Bath
    • 1,043 Sq Ft

    550 Pine Ln, Big Pine Key, FL 33043

    This newly remodeled 3-bedroom, 1-bathroom home is perfectly positioned on a spacious lot in the heart of Big Pine Key, offering 10,275 sq ft of land and an incredible 75 feet of waterfrontage, with a concrete seawall. With quick access to the ocean via Spanish Harbor Channel, this is a boater's dream come true. Inside, enjoy peace of mind with impact-rated windows and doors, a sturdy metal roof,

    Justyn Ewald Expert Realty LLC

    550 Pine Ln, Big Pine Key, FL 33043
  • /32

    $895,000

    Sold Jun 23, 2026

    30451 Hibiscus Ln, Big Pine Key, FL 33043

    • 4 Beds
    • 3 Baths
    • 2,503 Sq Ft
    • Built 2010

    Last Sold Summary

    • 8% Below List Price
    • $358/SF
    • 117 Days On Market

    Current Estimated Value $1,011,115

    Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

    30451 Hibiscus Ln, Big Pine Key, FL 33043
    • /43

      Est $1,101,392

      Not Listed For Sale

      17055 Kingfish Ln W, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,184 Sq Ft
      • Built 1988
      17055 Kingfish Ln W, Summerland Key, FL 33042

      Last Sold Summary

      • 38 Days On Market

  • /60

    $799,000

    $88K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 806 Sq Ft

    701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042

    ********Nightly Licensed Transient Rental!!!******** This amazing, two bedroom / one bathroom, open water front views , nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rental license. The floor plan makes the open water views as its main focus. Cook the catch of the day overlooking the waters that you just caught that prized fish

    Bobby Coe RE/MAX Keys Connection (KW)

    701 Spanish Main Dr Unit 49, 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 $633,770

    Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

    29073 Iris Dr, Big Pine Key, FL 33043
    • /50

      Est $960,995

      Not Listed For Sale

      17396 Jamaica Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,224 Sq Ft
      • Built 1992
      17396 Jamaica Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 1 Day On Market

  • /40

    $689,000

    • 1 Bed
    • 1 Bath
    • 820 Sq Ft

    2231 Middle Torch Rd, Summerland Key, FL 33042

    Imagine having the freedom to create your own secluded retreat in the heart of the Lower Florida Keys. This remarkable offering includes two adjacent 2.5-acre parcels, combining for approximately 5 acres--an exceptionally rare amount of land in the Florida Keys. Existing improvements include two separate residences, each offering one bedroom and one bathroom. One parcel is improved with a

    Justyn Ewald Expert Realty LLC

    2231 Middle Torch Rd, Summerland Key, FL 33042
  • /55

    $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 $1,061,843

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    231 W Indies Dr, Summerland Key, FL 33042
    • /74

      Est $3,012,672

      Not Listed For Sale

      22572 Jolly Roger Dr, Summerland Key, FL 33042

      • 6 Beds
      • 4 Baths
      • 3,225 Sq Ft
      • Built 1963
      22572 Jolly Roger Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 313 Days On Market

  • /41

    $949,000

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

    342 Spanish Main Dr, Summerland Key, FL 33042

    Welcome to 342 Spanish Main Drive, a beautiful canal-front home in the heart of Cudjoe Key, offering the perfect combination of waterfront living, modern comfort, and laid-back Florida Keys charm. This two-story residence features 3 bedrooms and 2 full bathrooms, thoughtfully designed for both everyday living and relaxing island escapes. The bright, open interior is move-in ready and includes a

    Monika Rydzak eXp Realty LLC KW Branch

    342 Spanish Main Dr, Summerland Key, FL 33042
  • /19

    $595,000

    Sold Jun 02, 2026

    27147 Dolphin Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • Built 1991

    Last Sold Summary

    • 8% Below List Price
    • $539/SF
    • 50 Days On Market

    Current Estimated Value $627,250

    Last Listing Agent Robin Nilsson Keller Williams Key West Compass Realty

    27147 Dolphin Rd, Summerland Key, FL 33042
    • /40

      Est $1,055,505

      Not Listed For Sale

      22983 Anne Bonny Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,320 Sq Ft
      • Built 1986
      22983 Anne Bonny Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 109 Days On Market

  • /21

    $847,000

    $50K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 574 Sq Ft

    9W Cooks, Cook Island Key, FL 33043

    Situated just offshore in the Lower Florida Keys, Cook's Key Lime Cottage offers a sublime blend of modern comfort and tropical allure. Perfect for avid fishermen and outdoor enthusiasts, real estate investors with a desire for an entirely unique Florida Keys experiential property to add to their portfolio, or those seeking a piece of the Florida Keys to where they can escape. Beautiful inside

    Greg Gordon The Island Collective Realty

    9W Cooks, Cook Island Key, FL 33043
  • /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 $458,000

    Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

    3 W Cook, Cook Island Key, FL 33043
    • /6

      Est $674,188

      Not Listed For Sale

      79 Coral Ave, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,144 Sq Ft
      • Built 2004
      79 Coral Ave, Summerland Key, FL 33042

      Last Sold Summary

      • 32 Days On Market

  • /36

    $1,169,000

    $81K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft

    29662 Independence Ave, Big Pine Key, FL 33043

    DOUBLE LOT waterfront opportunity in Big Pine Key! This charming 2 bedroom, 2 bathroom home is ideally situated on a fenced double lot along a canal with excellent boating access and a prime Lower Keys location. Boaters will appreciate the quick and convenient access to both the Atlantic Ocean and the Gulf , making this property an ideal home base for fishing, diving, and exploring the

    Halley Haack Coldwell Banker Schmitt RE Co.

    29662 Independence Ave, Big Pine Key, FL 33043
  • /35

    $669,000

    Sold Oct 24, 2025

    28212 Gato Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,077 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $621/SF
    • 80 Days On Market

    Current Estimated Value $714,026

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    28212 Gato Rd, Summerland Key, FL 33042

Showing Results 481 - 520, Page 13 of 18

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