Waterfront Homes for Sale in Summerland Key, FL

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  /44

  $2,246,000

  • 3 Beds
  • 1.5 Baths
  • 2,016 Sq Ft

  848 Caribbean Dr E, Summerland Key, FL 33042

  Built for the offshore lifestyle, this exceptional Summerland Key waterfront home blends luxury coastal living with the kind of boating access serious anglers dream about. Completely renovated from top to bottom, the property sits on a deep water canal with 60 feet of brand new concrete dockage and quick direct access to open water, making it ideal for larger center consoles, sportfish boats, and

  Jonathan Minerick Homecoin.com

  848 Caribbean Dr E, Summerland Key, FL 33042
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  /19

  $685,000

  • 3 Beds
  • 2 Baths
  • 986 Sq Ft

  29175 Violet Dr, Big Pine Key, FL 33043

  Eden Pines Gem: Fully updated, low assumable flood Modern Island Living: Updated Stilted Retreat in Golf-Cart Friendly Eden Pines!Welcome to 29175 Violet Drive, a fully updated 3-bedroom, 2-bathroom stilted sanctuary in the heart of Big Pine Key. This home is tucked into the vibrant, family-oriented community of Eden Pines Colony-a neighborhood where neighbors are friends and the island lifestyle

  Ralph Harvey LISTWITHFREEDOM.COM

  29175 Violet Dr, Big Pine Key, FL 33043
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  /52

  $487,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

  Seller is Motivated!Coastal Charm Meets Modern ComfortWelcome to your island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located within the gated waterfront community of Venture Out on Cudjoe Key.Inside, you'll find a bright, open-concept layout featuring a spacious living area that flows seamlessly into a thoughtfully designed

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
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  /24

  $300,000

  • Land
  • 2,178 Sq Ft
  • $6,000,000 per Acre

  701 Spanish Main Dr Unit 236, Cudjoe Key, FL 33042

  LOWEST-PRICED WATERFRONT LOT IN VENTURE OUT!Discover your own slice of the Florida Keys at Lot 236 in Venture Out on Cudjoe Key. This beautifully landscaped waterfront lot offers a rare combination of privacy, tropical surroundings, and incredible potential in one of the Keys' most sought-after gated communities.Tucked along a peaceful canal, the property features a 13.25-foot

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 236, Cudjoe Key, FL 33042
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  /41

  $840,000

  $40K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft

  3635 Tradewinds St, Big Pine Key, FL 33043

  Beautifully Renovated Single-Family Home in the Florida Keys This stunning 2-bedroom, 2-bathroom home with extra guess room downstairs, fully renovated in 2024, is perfect for fishing enthusiasts and those seeking a serene island lifestyle. The property boasts a 50-foot dock with no bridges to the ocean, ideal for quick access to the water. Located in a quiet neighborhood, this home features a

  Michel Luna Lifestyle International Realty

  3635 Tradewinds St, Big Pine Key, FL 33043
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  /22

  $819,000

  New Construction $20K PRICE DROP

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

  27215 Mariposa Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION!This charming 1,500 sqft home is a true retreat, perfectly positioned in the Lower Keys, just a moments walk from the popular Looe Key Tiki Bar and Boondocks restaurants. Tucked away in a quiet, low-traffic neighborhood, this property offers the ideal combination of peace and convenience, allowing you to embrace the relaxed Keys lifestyle.Inside, you'll

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  27215 Mariposa Rd, Summerland Key, FL 33042
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  /38

  $799,000

  $26K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  1634 Lantana Ln, Big Pine Key, FL 33043

  Custom-built 2-bedroom, 2-bathroom home (1987) situated on a boating canal in the sought-after Eden Pines neighborhood of Big Pine Key where the Key Deer roam.Short stilted home located on a 6,000 sq. ft. lot the property offers 60 feet of concrete seawall ideal for your boat of choice, with excellent boating access via Pine Channel. Boaters should note two bridges en route with

  Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  1634 Lantana Ln, Big Pine Key, FL 33043
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  /8

  $365,000

  • Land
  • 2,178 Sq Ft
  • $7,300,000 per Acre

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

  Discover your own piece of paradise in Venture Out! This beautifully maintained waterfront lot offers 17 feet of seawall and a private tropical setting enhanced by mature landscaping and thoughtful care. Whether you're looking for the perfect RV getaway, seasonal retreat, or future homesite, this property provides the ideal blend of privacy, beauty, and waterfront living.Located within the

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042
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  /74

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  27772 Astrangia Ave, Summerland Key, FL 33042

  Bring your boat and start enjoying the waterfront lifestyle from this beautifully remodeled 2-bedroom, 2-bath canal-front home in the Lower Keys. Ideally positioned near open water, the property offers approximately 46 feet of concrete seawall along a wide canal with convenient boating access to both the Atlantic and backcountry. Fishing, diving, kayaking, and days on the water are right outside

  Monika Rydzak eXp Realty LLC KW Branch

  27772 Astrangia Ave, Summerland Key, FL 33042
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  /46

  $785,000

  $10K PRICE DROP

  • 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

  Ryan Gernaat Coldwell Banker Schmitt Lower Keys (KW)

  29034 Rose Dr, Big Pine Key, FL 33043
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  /12

  $400,000

  $20K PRICE DROP

  • Land
  • 6,098 Sq Ft
  • $2,857,143 per Acre

  29517 Big Pine St, Big Pine Key, FL 33043

  Commercial waterfront lot at 29517 Big Pine St, Big Pine Key. Deep-water canal with quick access to both the Gulf of Mexico and the Atlantic Ocean, icommercial fishing, marine operations, boating, or waterfront business use. Located on a quiet cul-de-sac with exceptional privacy--no neighbors in front or on either side. Nearly surrounded by county-owned land that is not expected to be developed.

  Steven Koleno Beycome of Florida, LLC

  29517 Big Pine St, Big Pine Key, FL 33043
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  /55

  $1,799,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft

  22970 Gasparilla Ln, Cudjoe Key, FL 33042

  OPEN WATER VIEWS - BRAND NEW CUSTOM WATERFRONT HOME - DOUBLE LOT & MOVE IN READY. This ELEVATED 3 bedroom, 2 bathroom CBS home is a must see! Solid steel and concrete, standing seam white metal roof with impact windows and doors rated to 185 MPH. 2,050 total sq ft of living space includes a front porch, utility room on the lower level and a lanai off the back. A total of 1500 sq ft of living

  Joyce Craul Expert Realty LLC (HQ)

  22970 Gasparilla Ln, Cudjoe Key, FL 33042
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  /33

  $1,049,000

  $50K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,143 Sq Ft

  1615 Fern Ave, Big Pine Key, FL 33043

  Welcome to an incredible opportunity to enjoy an exceptional amount of home and land in the Lower Keys. This beautifully updated 3-bedroom, 2.5-bath waterfront home sits on a rare 12,000 sq. ft. double lot in the heart of Big Pine Key, offering generous space both inside and out without sacrificing the relaxed Keys lifestyle. Thoughtfully renovated throughout, the home features a bright, spacious

  Taron Wirth Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  1615 Fern Ave, Big Pine Key, FL 33043
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  /16

  $305,000

  $20K PRICE DROP

  • Land
  • 4,356 Sq Ft
  • $3,050,000 per Acre

  27935 Tarpon Terrace, Summerland Key, FL 33042

  Heather Mason Coastal Collection Real Estate Inc.

  27935 Tarpon Terrace, Summerland Key, FL 33042
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  /11

  $460,000

  $20K PRICE DROP

  • Land
  • 1,742 Sq Ft
  • $11,500,000 per Acre

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

  Discover the ultimate escape! This highly sought-after waterfront RV lot offers everything the coastal enthusiast dreams of, combining luxury amenities with unparalleled nautical access. Located on a wide street this lot is easily accessible for larger RV's and 5th wheels. Features a newer separate concrete parking area for your vehicle and a large level concrete pad for the Rv. Comes complete

  Carmen Brake Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

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