6,968

Homes in ZIP Code 33042

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  • /48

    $1,299,000

    $51K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    24347 Caribbean Dr W, Summerland Key, FL 33042

    Welcome to Summerland Key Cove! This beautifully home is perfectly situated on a deep-water canal with excellent boating access. Boaters will appreciate the new 17,000-lb boat lift and a quick ride to Looe Key, American Shoal, and the Adolf Bush wreck.The 1232 sq ft home sits on a 6,000 sq ft lot and features hurricane-impact windows, offering peace of mind and energy efficiency. The home has

    Agent Photo

    Shirley Carey

    Berkshire Hathaway HomeServices Knight & Gardner Realty

    24347 Caribbean Dr W, Summerland Key, FL 33042
  • /125

    $5,000,000

    Sold Jun 18, 2026

    24200 Overseas Hwy, Summerland Key, FL 33042

    • 5 Beds
    • 5.5 Baths
    • 3,000 Sq Ft
    • Built 1977

    Last Sold Summary

    • 19% Below List Price
    • $1,667/SF
    • 106 Days On Market

    Current Estimated Value $4,618,358

    Last Listing Agent Sylvia Werling Keller Williams Key West Compass Realty

    24200 Overseas Hwy, Summerland Key, FL 33042
    • /59

      Not Listed For Sale

      701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 2000
      701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

      Last Sold Summary

      • 76 Days On Market

  • /34

    $749,900

    • 3 Beds
    • 2 Baths
    • 1,431 Sq Ft

    28110 Dorothy Ave, Little Torch Key, FL 33042

    Island living comes easy here, with a free community boat ramp, nearby waterfront basin, and natural Lower Keys scenery all close to home. Set on a large 7,814 sq. ft. corner lot along State Road 4A in Ladies Acre, this 3 bedroom, 2 bath property offers 1,431 sq. ft. of comfortable living space surrounded by mature tropical greenery that adds privacy and natural beauty. Inside, the open living,

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    28110 Dorothy Ave, Little Torch Key, FL 33042
  • /49

    $650,000

    Sold Aug 20, 2025

    27317 Cayman Ln, Summerland Key, FL 33042

    • 2 Beds
    • 1.5 Baths
    • 1,029 Sq Ft
    • Built 2012

    Last Sold Summary

    • 28% Below List Price
    • $632/SF
    • 262 Days On Market

    Current Estimated Value $715,382

    Last Listing Agent Diana Fiddes Coldwell Banker Schmitt Key Largo

    27317 Cayman Ln, Summerland Key, FL 33042
    • /40

      Not Listed For Sale

      701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 816 Sq Ft
      • Built 1996
      701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

      Last Sold Summary

      • 22 Days On Market

  • /43

    $1,175,000

    $75K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,368 Sq Ft

    27395 Saint Lucie Ln, Summerland Key, FL 33042

    Welcome to your piece of paradise in Breezeswept Beach Estates, where laid-back island living meets premier canal-frontage. From here, it's an easy cruise to open water--perfect for early morning fishing runs, sunset sails, or spontaneous sandbar days. Inside, this bright and breezy retreat has been thoughtfully updated with stainless steel appliances, sleek Silestone countertops, and warm

    Agent Photo

    Michelle Vanhoose

    Coldwell Banker Schmitt Real Estate Co.

    27395 Saint Lucie Ln, Summerland Key, FL 33042
  • /5

    $725,000

    Sold Jul 30, 2025

    19462 Canal Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,394 Sq Ft
    • Built 1990

    Last Sold Summary

    • 6% Below List Price
    • $520/SF
    • 3 Days On Market

    Current Estimated Value $751,268

    Last Listing Agent Jacqui Norman Berkshire Hathaway HomeServices Knight & Gardner Realty

    19462 Canal Dr, Summerland Key, FL 33042
    • /37

      Not Listed For Sale

      27883 Coral Shores Rd, Little Torch Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft
      • Built 1973
      27883 Coral Shores Rd, Little Torch Key, FL 33042

      Last Sold Summary

      • 9 Days On Market

  • /22

    $685,000

    $29K PRICE DROP Under Contract
    • 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

    4039 Egret Ln, Summerland Key, FL 33042
  • /27

    $300,000

    Sold Nov 26, 2025

    27983 Snapper Ln, Little Torch Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft
    • Built 1987

    Last Sold Summary

    • 9% Below List Price
    • $446/SF
    • 60 Days On Market

    Last Listing Agent Sandra Dolowy KeyIsle Realty

    27983 Snapper Ln, Little Torch Key, FL 33042
    • /50

      Est $833,230

      Not Listed For Sale

      489 Pirates Rd, Little Torch Key, FL 33042

      • 4 Beds
      • 4 Baths
      • 1,638 Sq Ft
      • Built 1984
      489 Pirates Rd, Little Torch Key, FL 33042

      Last Sold Summary

      • 38 Days On Market

  • /43

    $1,799,000

    • 3 Beds
    • 2.5 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

    51 Sawyer Dr, Cudjoe Key, FL 33042
  • /2

    $55,000

    Sold Oct 22, 2025

    Lot 2 Rainbow Beach, Big Torch Key, FL 33042

    • Land
    • 5,000 Sq Ft
    • $479,160 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 2 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot 2 Rainbow Beach, Big Torch Key, FL 33042
    • /54

      Not Listed For Sale

      701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1999
      701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

      Last Sold Summary

      • 194 Days On Market

  • /73

    $2,849,000

    $150K PRICE DROP
    • 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

    17041 Marlin Dr, Sugarloaf Key, FL 33042
  • /49

    $280,000

    Sold Jun 03, 2026

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft
    • Built 1976

    Last Sold Summary

    • $406/SF
    • 98 Days On Market

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    • /35

      Est $235,021

      Not Listed For Sale

      701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

      Last Sold Summary

      • 22 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

    24764 Overseas Hwy, Summerland Key, FL 33042
  • /46

    $1,390,000

    Sold Aug 26, 2025

    229 Caribbean Dr E, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Below List Price
    • $1,207/SF
    • 30 Days On Market

    Current Estimated Value $1,404,471

    Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    229 Caribbean Dr E, Summerland Key, FL 33042
    • /51

      Not Listed For Sale

      701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 2006
      701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

      Last Sold Summary

      • 27 Days On Market

  • /28

    $689,000

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft

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

    A Classic Keys Boating Cottage! Exceptional value for a 3 bedroom 2 bath waterfront home in the Lower Keys! With 60' of seawall, enjoy easy boating access to nearby hot spots in the gulf and ocean side. The State Road 4a boat ramp is just a few doors away which is so convenient to launch your boat. Plenty of parking out front and room for a pool. Featuring laminate floors, a dedicated laundry

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    711 State Rd Unit 4A, Little Torch Key, FL 33042
  • /68

    $2,250,000

    Sold Apr 03, 2026

    24266 Caribbean Dr W, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,055 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $1,095/SF
    • 14 Days On Market

    Current Estimated Value $2,283,117

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    24266 Caribbean Dr W, Summerland Key, FL 33042
    • /3

      Not Listed For Sale

      Lot 24 Vacant Land, Big Torch Key, FL 33042

      Lot 24 Vacant Land, Big Torch Key, FL 33042

      Last Sold Summary

      • 206 Days On Market

  • /43

    $4,500,000

    • 2 Beds
    • 2 Baths
    • 1,800 Sq Ft

    4670 Dorn Rd, Summerland Key, FL 33042

    A must see to appreciate Boater's Paradise in the Lower Florida Keys. Experience a truly rare offering on Big Torch Key--an extraordinary 2.84-acre waterfront estate designed for the serious boater and those seeking complete seclusion. With over 1,000 feet of waterfront access on a premier point lot, this property delivers unmatched access, panoramic open-water views, and the ultimate in privacy.

    Agent Photo

    Sharon Davison

    Keller Williams Key West Compass Realty

    4670 Dorn Rd, Summerland Key, FL 33042
  • /29

    $740,000

    Sold Oct 31, 2025

    27138 Dolphin Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Built 2022

    Last Sold Summary

    • 14% Below List Price
    • $561/SF
    • 181 Days On Market

    Current Estimated Value $777,862

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    27138 Dolphin Rd, Summerland Key, FL 33042
    • /11

      Not Listed For Sale

      LOT 38 W Indies Dr, Ramrod Key, FL 33042

      LOT 38 W Indies Dr, Ramrod Key, FL 33042

      Last Sold Summary

      • 144 Days On Market

  • /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

    21250 Conch Dr, Cudjoe Key, FL 33042
  • /7

    $4,275,000

    Sold Mar 04, 2026

    231 E Shore Dr Unit 7, Summerland Key, FL 33042

    • 5 Beds
    • 5.5 Baths
    • 3,119 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $1,371/SF
    • 114 Days On Market

    Last Listing Agent Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

    231 E Shore Dr Unit 7, Summerland Key, FL 33042
    • /14

      Est $206,964

      Not Listed For Sale

      27391 W Indies Dr, Ramrod Key, FL 33042

      27391 W Indies Dr, Ramrod Key, FL 33042

      Last Sold Summary

      • 2 Days On Market

  • /62

    $1,499,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,587 Sq Ft

    22410 Jolly Roger Dr, Summerland Key, FL 33042

    Welcome to your oceanfront retreat on Cudjoe Key, where panoramic wide open ocean views, exceptional outdoor living, and easy boating access come together to create the quintessential Florida Keys lifestyle. Built on a lot and a half with durable CBS construction, this inviting 2-bedroom, 2-bath, 1,587 sq. ft. home is perfectly positioned to take advantage of its spectacular waterfront setting.

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    22410 Jolly Roger Dr, Summerland Key, FL 33042
  • /41

    $775,000

    Sold May 01, 2026

    22939 Privateer Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 1988

    Last Sold Summary

    • $602/SF
    • 3 Days On Market

    Current Estimated Value $772,519

    Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

    22939 Privateer Dr, Summerland Key, FL 33042
    • /21

      Not Listed For Sale

      701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 770 Sq Ft
      • Built 1978
      701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

      Last Sold Summary

      • 0 Days On Market

  • /2

    $30,000

    $20K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $187,500 per Acre

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

    Still time to submit to receive 2 points into ROGO. Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter attach 2 additional lots available each for $40,000

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042
  • /67

    $3,150,000

    Sold Jun 09, 2026

    270 E Caribbean Dr, Summerland Key, FL 33042

    • 4 Beds
    • 4 Baths
    • 2,375 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Below List Price
    • $1,326/SF
    • 22 Days On Market

    Current Estimated Value $3,087,223

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    270 E Caribbean Dr, Summerland Key, FL 33042
    • /38

      Est $1,340,710

      Not Listed For Sale

      17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,600 Sq Ft
      • Built 1994
      17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

      Last Sold Summary

      • 15 Days On Market

  • /65

    $2,499,000

    • 4 Beds
    • 2 Baths
    • 2,739 Sq Ft

    21023 2nd Ave, Summerland Key, FL 33042

    Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    21023 2nd Ave, Summerland Key, FL 33042
  • /55

    $5,003,500

    Sold Jan 05, 2026

    1151 Ocean Dr, Summerland Key, FL 33042

    • 5 Beds
    • 6 Baths
    • 3,952 Sq Ft
    • Built 2007

    Last Sold Summary

    • 28% Below List Price
    • $1,266/SF
    • 47 Days On Market

    Current Estimated Value $5,352,024

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

    1151 Ocean Dr, Summerland Key, FL 33042
    • /8

      Est $242,112

      Not Listed For Sale

      1135 Hakluyt Ln, Cudjoe Key, FL 33042

      1135 Hakluyt Ln, Cudjoe Key, FL 33042

      Last Sold Summary

      • 7 Days On Market

  • /2

    $30,000

    $20K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $187,500 per Acre

    0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042

    Still time to submit to receive 2 points into ROGO. Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter attach 2 additional lots available each for $40,000

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042

Showing Results 41 - 80, Page 2 of 18

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