8,608

Summerland Key, FL Homes

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  • /66

    $525,000

    $14K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 836 Sq Ft

    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

    Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private deck—an ideal spot for your morning coffee or evening

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    (645) 666-0297

    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
  • /19

    $4,500 Per Month

    • 2 Beds
    • 1 Bath
    • 884 Sq Ft
    • House for Rent

    27346 Martinique Ln, Summerland Key, FL 33042

    Welcome to your private slice of paradise in the Florida Keys. This fully remodeled, exquisitely furnished 2-bedroom, 1-bathroom waterfront home is a true island escape. Where turquoise waters, swaying palms, and golden sunsets become your everyday view. Enjoy direct ocean access from your private dock, no bridges to slow you down. Lounge by the heated pool, dine under the stars, and feel the

    Alicia Rufino Island Living Realty, LLC

    27346 Martinique Ln, Summerland Key, FL 33042
  • /2

    $510,000

    Sold Sep 08, 2025

    Unlisted Address

    • 3 Beds
    • 2 Baths
    • 972 Sq Ft
    • Built 1989

    Last Sold Summary

    • $525/SF

    Current Estimated Value $513,495

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    Unlisted Address
    • /22

      Not Listed For Sale

      133 Freedom Ln, Big Pine Key, FL 33043

      • 2 Beds
      • 1.5 Baths
      • 720 Sq Ft
      • Built 1972
      133 Freedom Ln, Big Pine Key, FL 33043

      Last Sold Summary

      • 49 Days On Market

  • /73

    $2,775,000

    • 3 Beds
    • 2 Baths
    • 2,232 Sq Ft

    23941 Henry St, Summerland Key, FL 33042

    Beach House Oceanfront retreat with protected dockage & direct access to both the Ocean & Gulf. Wake each morning to breathtaking Atlantic sunrises and unwind beneath glowing sunsets in this custom-built, two-story CBS oceanfront home. Tucked away on a private street shared by only four residences, this exceptional island inspired sanctuary offers panoramic ocean views, unmatched privacy, and the

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    (305) 395-0696

    23941 Henry St, Summerland Key, FL 33042
  • /73

    $2,925,000

    Sold Jun 10, 2025

    17018 Wahoo Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft
    • Built 1991

    Last Sold Summary

    • 25% Below List Price
    • $1,987/SF
    • 122 Days On Market

    Current Estimated Value $2,946,581

    Last Listing Agent Coby Taylor Expert Realty LLC (HQ)

    17018 Wahoo Ln, Summerland Key, FL 33042
    • /14

      Not Listed For Sale

      1639 Pine Channel Dr, Little Torch Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 6,725 Sq Ft
      • Built 1975
      1639 Pine Channel Dr, Little Torch Key, FL 33042

      Last Sold Summary

      • 7 Days On Market

  • /48

    $799,000

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft

    1672 Pandorea Ln, Big Pine Key, FL 33043

    Discover canal-front living in Eden Pines Colony where local amenities are within easy reach! The owners have maximized this 8,063 sq. ft. property for outdoor living, from the screened sitting and grilling area below, to the lush gardens surrounding the amazing outdoor shower. The inside is bright and airy featuring a wood-planked cathedral ceiling in the great room, granite counters in the

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (855) 508-0388

    1672 Pandorea Ln, Big Pine Key, FL 33043
  • /58

    $572,000

    Sold May 27, 2026

    175 E Cahill Ct, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1991

    Last Sold Summary

    • 5% Below List Price
    • $567/SF
    • 40 Days On Market

    Current Estimated Value $596,391

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

    175 E Cahill Ct, Big Pine Key, FL 33043
    • /29

      Not Listed For Sale

      1693 Bayview Dr, Little Torch Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 917 Sq Ft
      • Built 1976
      1693 Bayview Dr, Little Torch Key, FL 33042

      Last Sold Summary

      • 60 Days On Market

  • /43

    $763,000

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

    30374 Oleander Blvd, Big Pine Key, FL 33043

    If you want a spacious home with plenty of privacy, this property delivers. Set within a lushly landscaped 12,500 sq. ft. double lot, the 2,136 sq. ft. living area provides ample space for family and guests with 4-bedrooms, 2-baths, a family room, laundry room and additional room that could be a 5th bedroom. Refreshing colors complement the space, and the tasteful furnishings are included with

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (877) 357-0409

    30374 Oleander Blvd, Big Pine Key, FL 33043
  • /38

    $790,000

    Sold May 22, 2026

    30471 Coconut Hwy, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,513 Sq Ft
    • Built 1959

    Last Sold Summary

    • 14% Below List Price
    • $522/SF
    • 319 Days On Market

    Current Estimated Value $804,027

    Last Listing Agent Richard Haskins Buy The Keys

    30471 Coconut Hwy, Big Pine Key, FL 33043
    • /29

      Not Listed For Sale

      701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 828 Sq Ft
      • Built 2001
      701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

      Last Sold Summary

      • 14 Days On Market

  • /67

    $1,435,000

    Open Sat 11AM - 1PM $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,310 Sq Ft

    29562 Saratoga Ave, Big Pine Key, FL 33043

    Embrace island living in your own tropical paradise, where comfort, space, and waterfront access create a remarkable oasis for boating and relaxation. Welcome to Pine Channel Estates, the ultimate destination for anglers and water enthusiasts. Currently operating as a successful vacation rental, this gem is ideal for a second home that can offset some of the annual costs of ownership, and

    Agent Photo

    Ryan Gernaat

    Coldwell Banker Schmitt Lower Keys (KW)

    (833) 404-4618

    29562 Saratoga Ave, Big Pine Key, FL 33043
  • /16

    $1,400,000

    Sold Mar 16, 2026

    570 Blackbeard Rd, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 1,500 Sq Ft
    • Built 2026

    Last Sold Summary

    • 3% Below List Price
    • $933/SF
    • 14 Days On Market

    Current Estimated Value $1,433,000

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    570 Blackbeard Rd, Summerland Key, FL 33042
    • /15

      Not Listed For Sale

      8 Calico Jack Circle Cir, Verifying, FL 33042

      8 Calico Jack Circle Cir, Verifying, FL 33042

      Last Sold Summary

      • 18 Days On Market

  • /34

    $1,575,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,667 Sq Ft

    22865 Redfish Ln, Summerland Key, FL 33042

    The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to

    Agent Photo

    Anneliese Dietrick

    Coldwell Banker Schmitt RE Co.

    (645) 230-1445

    22865 Redfish Ln, Summerland Key, FL 33042
  • /45

    $780,000

    Sold Jul 18, 2025

    29025 Geranium Dr, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft
    • Built 1981

    Last Sold Summary

    • 6% Below List Price
    • $855/SF
    • 44 Days On Market

    Current Estimated Value $790,366

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    29025 Geranium Dr, Big Pine Key, FL 33043
    • /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

  • /42

    $924,900

    $74K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    22954 Buccaneer Ln, Cudjoe Key, FL 33042

    Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water—ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (877) 542-8054

    22954 Buccaneer Ln, Cudjoe 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 $709,465

    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

  • /37

    $899,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,203 Sq Ft

    153 Peg Leg Ln, Cudjoe Key, FL 33042

    Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (877) 317-2645

    153 Peg Leg Ln, Cudjoe 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 $733,282

    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

  • /71

    $2,795,000

    $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,913 Sq Ft

    20920 5th Ave W, Summerland Key, FL 33042

    Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

    Agent Photo

    Miriam Novotny

    Compass Florida, LLC

    (877) 939-4083

    20920 5th Ave W, Summerland 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
    • /64

      Not Listed For Sale

      15 W Cooks, Cook Island Key, FL 33043

      • 3 Beds
      • 3 Baths
      • 1,551 Sq Ft
      • Built 1977
      15 W Cooks, Cook Island Key, FL 33043

      Last Sold Summary

      • 16 Days On Market

  • /45

    $849,000

    $76K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    195 W Shore Dr, Summerland Key, FL 33042

    Welcome to a truly unique aviation property in the heart of Summerland Key! Located at the end of the exclusive Summerland Key airstrip on a 12,425 sq. ft. double lot, this concrete block home offers the ultimate blend of sky, sea, and space. Featuring a 37' x 27' airplane hangar, 2-car garage, and expansive driveway, this 3-bedroom, 2-bathroom plus bonus/4th Bedroom residence is tailor-made for

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (844) 619-6402

    195 W Shore Dr, 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 $1,392,633

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

    229 Caribbean Dr E, Summerland Key, FL 33042
    • /20

      Not Listed For Sale

      28587 Peg Leg Rd, Little Torch Key, FL 33042

      28587 Peg Leg Rd, Little Torch Key, FL 33042

      Last Sold Summary

      • 80 Days On Market

  • /70

    $2,800,000

    • 4 Beds
    • 3 Baths
    • 3,286 Sq Ft

    21640 Overseas Hwy, Summerland Key, FL 33042

    SPECIAL DAILY TRANSIENT LICENSE!!!Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers

    Agent Photo

    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    (855) 799-5158

    21640 Overseas Hwy, Summerland 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 $2,273,007

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    24266 Caribbean Dr W, Summerland Key, FL 33042
    • /50

      Est $825,130

      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

  • /69

    $3,500,000

    • 3 Beds
    • 3 Baths
    • 2,295 Sq Ft

    1083 Labat Ln, Cudjoe Key, FL 33042

    Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (645) 233-0155

    1083 Labat Ln, Cudjoe 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 $739,756

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    27138 Dolphin Rd, Summerland Key, FL 33042
    • /35

      Est $219,010

      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

  • /27

    $987,500

    • 4 Beds
    • 2 Baths
    • 1,536 Sq Ft

    3962 No Name Rd, Big Pine Key, FL 33043

    Waterfront DUPLEX ~ CBS Construction 4BD/2BA with 2BD|1BA on each side. Property features, excellent boating access, full 70' concrete seawall, covered porch for both units, tile flooring, accordion shutters, separate utility/laundry rooms on each side, 2 central AC units and 2 electric meters. Newer metal roof within 2 years. Fenced yard with room to park your boat trailer. Great investment

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    (888) 275-1086

    3962 No Name Rd, Big Pine Key, FL 33043
  • /47

    $1,100,000

    Sold Jun 27, 2025

    21014 7th Ave, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,361 Sq Ft
    • Built 1988

    Last Sold Summary

    • 19% Below List Price
    • $808/SF
    • 102 Days On Market

    Current Estimated Value $1,106,731

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    21014 7th Ave, 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

Showing Results 41 - 80, Page 2 of 18

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