8,608

Summerland Key, FL Homes

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    • /49

      Est $850,853

      Not Listed For Sale

      29765 Osprey Ln, Big Pine Key, FL 33043

      • 2 Beds
      • 1.5 Baths
      • 1,456 Sq Ft
      • Built 1988
      29765 Osprey Ln, Big Pine Key, FL 33043

      Last Sold Summary

      • 52 Days On Market

  • /22

    $685,000

    $29K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    4039 Egret Ln, Summerland Key, FL 33042

    Charming 2 bed, 1 bath home in Big Torch Key featuring hardiplank siding, impact windows throughout, and a metal roof. The 12,000 sq ft lot offers 120 ft of waterfront, including 60 ft along the canal cleared for dockage. The spacious yard provides room to add a pool, tiki hut, outdoor entertaining areas, and still have ample space for boat, trailer or RV parking. Located on a deep-water canal

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (645) 238-9391

    4039 Egret Ln, Summerland Key, FL 33042
  • /50

    $1,900,000

    Sold Mar 27, 2026

    711 W Indies Dr, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,000 Sq Ft
    • Built 2025

    Last Sold Summary

    • 5% Below List Price
    • $950/SF
    • 62 Days On Market

    Current Estimated Value $1,933,329

    Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

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

      Est $274,678

      Not Listed For Sale

      701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

      • Studio
      • Built 1981
      701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

      Last Sold Summary

  • /46

    $795,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    29034 Rose Dr, Big Pine Key, FL 33043

    Experience the laid-back Florida Keys lifestyle in this beautifully updated, turn-key canal-front retreat, nestled in the quiet Eden Pines neighborhood among the roaming Key Deer. Situated on a 50-foot concrete seawall with step-down access, fish cleaning station, and a new boat lift, this property offers excellent boating access to both the ocean and bay. Inside, the open concept living area is

    Agent Photo

    Ryan Gernaat

    Coldwell Banker Schmitt Lower Keys (KW)

    (866) 610-4443

    29034 Rose Dr, Big Pine Key, FL 33043
  • /26

    $610,000

    Sold Apr 03, 2026

    29030 Iris Dr, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,353 Sq Ft
    • Built 1974

    Last Sold Summary

    • 15% Below List Price
    • $451/SF
    • 449 Days On Market

    Current Estimated Value $674,926

    Last Listing Agent Justyn Ewald Expert Realty LLC (HQ)

    29030 Iris Dr, Big Pine Key, FL 33043
    • /2

      Est $700,149

      Not Listed For Sale

      27188 Dolphin Rd, Ramrod Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1991
      27188 Dolphin Rd, Ramrod Key, FL 33042

      Last Sold Summary

  • /38

    $1,399,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    51 Drost Dr, Summerland Key, FL 33042

    Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 808-1276

    51 Drost Dr, Summerland Key, FL 33042
  • /41

    $1,105,000

    Sold Sep 26, 2025

    22946 Bluegill Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1975

    Last Sold Summary

    • 14% Below List Price
    • $921/SF
    • 255 Days On Market

    Current Estimated Value $1,108,393

    Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt RE Co.

    22946 Bluegill Ln, Summerland Key, FL 33042
    • /68

      Est $952,612

      Not Listed For Sale

      31670 Avenue C, Big Pine Key, FL 33043

      • 3 Beds
      • 2 Baths
      • 1,227 Sq Ft
      • Built 1956
      31670 Avenue C, Big Pine Key, FL 33043

      Last Sold Summary

      • 28 Days On Market

  • /85

    $1,695,000

    • 4 Beds
    • 3 Baths
    • 2,136 Sq Ft

    30363 Flamingo Ln, Big Pine Key, FL 33043

    Welcome to the ultimate angler's retreat in Tropical Bay Estates. This elevated concrete waterfront home offers quick access to both the Atlantic and Gulf, putting you in the heart of world-class fishing and diving. Located just a few miles from Bahia Honda State Park, you're ideally positioned for elite tarpon fishing, backcountry action, reef trips, and offshore runs. The dock is built for

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    (855) 922-5281

    30363 Flamingo Ln, Big Pine Key, FL 33043
  • /47

    $1,075,000

    Sold May 13, 2026

    110 Doubloon Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Below List Price
    • $853/SF
    • 9 Days On Market

    Current Estimated Value $1,000,215

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    110 Doubloon Ln, Summerland Key, FL 33042
    • /3

      Not Listed For Sale

      27732 Astrangia Ave, Little Torch Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,092 Sq Ft
      • Built 1985
      27732 Astrangia Ave, Little Torch Key, FL 33042

      Last Sold Summary

      • 275 Days On Market

  • /43

    $1,799,000

    • 3 Beds
    • 3 Baths
    • 2,456 Sq Ft

    51 Sawyer Dr, Cudjoe Key, FL 33042

    Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (866) 618-8489

    51 Sawyer Dr, Cudjoe Key, FL 33042
  • /61

    $1,750,000

    Sold Mar 09, 2026

    876 Gulf Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,172 Sq Ft
    • Built 1978

    Last Sold Summary

    • 20% Below List Price
    • $1,493/SF
    • 122 Days On Market

    Current Estimated Value $1,693,259

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

    876 Gulf Dr, Summerland Key, FL 33042
    • /14

      Not Listed For Sale

      12, 13, 14 Cook Island, Cook Island Key, FL 33043

      12, 13, 14 Cook Island, Cook Island Key, FL 33043

      Last Sold Summary

      • 24 Days On Market

  • /73

    $2,999,000

    • 3 Beds
    • 2 Baths
    • 2,170 Sq Ft

    17041 Marlin Dr, Sugarloaf Key, FL 33042

    Experience breathtaking sunsets over Sugarloaf Sound from this 2-story CBS open water estate offering 3 bedrooms, 2 baths, and 2,170 sq ft of elevated coastal living just 20 minutes from Key West. Situated on a generous 15,650 sq ft lot, this meticulously maintained home features impact doors and windows, metal roof, exterior elevator, and lush tropical landscaping including a dedicated orchid

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 684-0921

    17041 Marlin Dr, Sugarloaf Key, FL 33042
  • /17

    $190,000

    Sold Apr 29, 2026

    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 300 Sq Ft
    • Built 2018

    Last Sold Summary

    • 14% Below List Price
    • $633/SF
    • 66 Days On Market

    Current Estimated Value $215,115

    Last Listing Agent Darlene Alferes Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
    • /8

      Not Listed For Sale

      0000 Dorn Rd, Big Torch Key, FL 33042

      0000 Dorn Rd, Big Torch Key, FL 33042

      Last Sold Summary

      • 103 Days On Market

  • /5

    $285,000

    • Land
    • 1.01 Acres
    • $282,178 per Acre

    Unlisted Address

    Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    (645) 219-1669

    Unlisted Address
  • /26

    $390,000

    Sold Jul 10, 2025

    27873 Coral Shores Rd, Little Torch Key, FL 33042

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

    Last Sold Summary

    • 19% Below List Price
    • $569/SF
    • 70 Days On Market

    Last Listing Agent Tracy Shields KeyIsle Realty

    27873 Coral Shores Rd, Little Torch Key, FL 33042
    • /3

      Not Listed For Sale

      Vacant Lot Diane Rd, Big Pine Key, FL 33043

      Vacant Lot Diane Rd, Big Pine Key, FL 33043

      Last Sold Summary

      • 35 Days On Market

  • /9

    $899,000

    • Land
    • 12,000 Sq Ft
    • $3,263,370 per Acre

    24764 Overseas Hwy, Summerland Key, FL 33042

    Rare opportunity in the heart of Summerland Key, two contiguous waterfront lots totaling 12,000 SF in the SC (Suburban Commercial) zoning district. Offering over 120 feet of premium frontage - both on the highly visible Overseas Highway and on deep-water accessible oceanside canal - this property delivers exceptional visibility and flexible commercial potential. 120' concrete dockage with direct

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    (786) 952-6715

    24764 Overseas Hwy, Summerland Key, FL 33042
  • /64

    $809,000

    Sold Nov 12, 2025

    3714 Pine St, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1989

    Last Sold Summary

    • 17% Below List Price
    • $722/SF
    • 194 Days On Market

    Current Estimated Value $809,236

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    3714 Pine St, Big Pine Key, FL 33043
    • /34

      Not Listed For Sale

      27772 Astrangia Ave, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,012 Sq Ft
      • Built 1978
      27772 Astrangia Ave, Summerland Key, FL 33042

      Last Sold Summary

      • 44 Days On Market

  • /28

    $649,000

    Open Sat 11AM - 1PM
    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft

    19464 Seminole St, Summerland Key, FL 33042

    Move-In Ready Sugarloaf Key Retreat! Ideally located on beautiful Sugarloaf Key, this charming elevated 2-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and island living. Just moments from a wonderful elementary and middle school, this bright and airy home welcomes you with an open floor plan filled with beautiful natural light, creating a warm and inviting atmosphere

    Agent Photo

    Miriam Novotny

    Compass Florida, LLC

    (645) 231-3946

    19464 Seminole St, Summerland Key, FL 33042
  • /91

    $3,675,000

    Sold May 11, 2026

    493 Coral Ave, Ramrod Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 1,728 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Below List Price
    • $2,127/SF
    • 10 Days On Market

    Current Estimated Value $3,733,938

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    493 Coral Ave, Ramrod Key, FL 33042
    • /2

      Est $936,646

      Not Listed For Sale

      1581 State Rd Unit 4A, Little Torch Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,144 Sq Ft
      • Built 2007
      1581 State Rd Unit 4A, Little Torch Key, FL 33042

      Last Sold Summary

  • /49

    $1,399,000

    $200K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft

    21250 Conch Dr, Cudjoe Key, FL 33042

    Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 959-3732

    21250 Conch Dr, Cudjoe Key, FL 33042
  • /8

    $340,000

    Sold Dec 11, 2025

    0 Overseas Hwy, Summerland Key, FL 33042

    • Land
    • 12,500 Sq Ft
    • $1,184,832 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 328 Days On Market

    Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

    0 Overseas Hwy, Summerland Key, FL 33042
    • /2

      Not Listed For Sale

      0 Vacant Unit 607262, Saddlebunch, FL 33040

      0 Vacant Unit 607262, Saddlebunch, FL 33040

      Last Sold Summary

  • /2

    $45,000

    $5K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $281,250 per Acre

    0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042

    Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. worth 2 pts applying for Letter 2 additional lots available each for $50,000

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    (844) 484-2446

    0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042
  • /52

    $1,530,000

    Sold Jan 16, 2026

    1370 Long Beach Dr, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,181 Sq Ft
    • Built 2011

    Last Sold Summary

    • 4% Below List Price
    • $1,296/SF
    • 33 Days On Market

    Current Estimated Value $1,550,432

    Last Listing Agent Coby Taylor Expert Realty LLC (HQ)

    1370 Long Beach Dr, Big Pine Key, FL 33043
    • /14

      Est $399,149

      Not Listed For Sale

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

      • 3 Beds
      • Built 1943
      30919 Edward Rd Unit A, Big Pine Key, FL 33043

      Last Sold Summary

      • 119 Days On Market

  • /64

    $1,080,000

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    22852 Buccaneer Ln, Summerland Key, FL 33042

    Experience the best of Keys living in this beautifully renovated waterfront home in sought-after Cudjoe Key--just minutes from local favorites like Square Grouper, 420 Lounge, and The Morning Joint. Boaters will appreciate the excellent access, complete with a concrete dock and 10,000 lb boat lift, making it easy to get on the water whenever you like. Privacy sets this property apart. The

    Agent Photo

    Austin Kimbler

    Expert Realty LLC (HQ)

    (645) 220-0519

    22852 Buccaneer Ln, Summerland Key, FL 33042
  • /21

    $775,000

    Sold Mar 23, 2026

    27360 Saint Croix Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1983

    Last Sold Summary

    • 16% Below List Price
    • $673/SF
    • 272 Days On Market

    Current Estimated Value $847,043

    Last Listing Agent Terry Bush Bluescape Real Estate

    27360 Saint Croix Ln, Summerland Key, FL 33042
    • /2

      Est $514,749

      Not Listed For Sale

      17172 Marlin Dr, Sugarloaf Shores, FL 33042

      • Studio
      17172 Marlin Dr, Sugarloaf Shores, FL 33042

      Last Sold Summary

  • /8

    $120,000

    • Land

    Lot 6 Vacant Land, Big Pine Key, FL 33043

    Positioned just off US-1 (Jimmy Buffett Memorial Highway), this parcel of land benefits from excellent visibility and accessibility, supporting a wide variety of potential commercial uses.Potential for securing valuable ROGO points for future permitting needs in Monroe County (buyer to verify the number of ROGO points with the County).

    Agent Photo

    Austin Kimbler

    Expert Realty LLC (HQ)

    (833) 721-5033

    Lot 6 Vacant Land, Big Pine Key, FL 33043
  • /58

    $760,000

    Sold Aug 19, 2025

    640 Carolyn Ave, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 848 Sq Ft
    • Built 2021

    Last Sold Summary

    • 2% Below List Price
    • $896/SF
    • 66 Days On Market

    Current Estimated Value $753,580

    Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

    640 Carolyn Ave, Summerland Key, FL 33042
    • /2

      Not Listed For Sale

      701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 897 Sq Ft
      • Built 2000
      701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

      Last Sold Summary

Showing Results 161 - 200, Page 5 of 18

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