Waterfront Homes for Sale in Summerland Key, FL

• 

  

  

  /36

  $779,000

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  1719 Narcissus Ave, Big Pine Key, FL 33043

  Located in the peaceful National Key Deer Refuge, this charming 2BD/2BA canal front home in Eden Pines offers the perfect blend of tranquility and classic Florida Keys living. Enjoy frequent visits from the beloved Key Deer while relaxing on one of the screened porches. The property features a fenced yard, outdoor shower, garage, storage area, and rainwater collection system for easy landscape

  Karen Haack Coldwell Banker Schmitt RE Co.

  1719 Narcissus Ave, Big Pine Key, FL 33043
• 

  

  

  /74

  $2,950,000

  Open House 7/03 $550K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,812 Sq Ft

  16805 Tamarind Rd, Summerland Key, FL 33042

  OPEN WATER RESORT STYLE CONCRETE POOL home on sought after Southpoint, Sugarloaf Shores. This exceptional 4-bedroom, 3-bath concrete waterfront residence captures breathtaking open water views from nearly every room and delivers the ultimate Florida Keys lifestyle.Positioned on a generous, beautifully landscaped lot with mature palms and established tropical greenery, the property welcomes

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  16805 Tamarind Rd, Summerland Key, FL 33042
• 

  

  

  /25

  $569,700

  • 2 Beds
  • 1 Bath
  • 718 Sq Ft

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042

  Licensed nightly rental. Brand new raised Sea Wall!! Discover island living at 701 Spanish Main Dr, Unit 335 in Cudjoe Key, FL. 2Bd/1Ba successful vacation rental located in a premium location on the water with open water views and features a 35' concrete seawall for docking a boat. Dock is equipped with dock posts, cleats, water, and storage. Large patio space to enjoy paradise overlooking the

  Sarah Dolson Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042
• 

  

  

  /35

  $1,250,000

  $49K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,774 Sq Ft

  30525 Winifred St, Big Pine Key, FL 33043

  Nestled in the heart of Big Pine Key, this private canal-front retreat with screened in POOL offers the perfect blend of comfort, space, and island living. Situated on an oversized 21,438 fenced in corner lot with a private gated entrance, the property provides exceptional privacy and a peaceful setting surrounded by tropical beauty. Plenty of space for your RV, Boat Trailer and more. It's a

  Joyce Craul Expert Realty LLC (HQ)

  30525 Winifred St, Big Pine Key, FL 33043
• 

  

  

  /49

  $1,499,000

  • 4 Beds
  • 3 Baths
  • 1,800 Sq Ft

  27372 W Indies Dr, Summerland Key, FL 33042

  Offered for the first time, this custom-built 4 bedroom, 3 bathroom waterfront residence on Ramrod Key showcases refined coastal design, exceptional craftsmanship, and magnificent ocean views. Completed in 2020, the two-story stilted home was thoughtfully designed to maximize light, views, and seamless indoor-outdoor living, with one master bedroom ensuite on each level for comfort and

  Sandra Dolowy KeyIsle Realty

  27372 W Indies Dr, Summerland Key, FL 33042
• 

  

  /54

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,095 Sq Ft

  667 Caribbean Dr E, Summerland Key, FL 33042

  PILOTS and BOATERS will love this! Tucked away in the heart of Summerland Key, this charming 2-bedroom, 2-bath home captures the essence of true Florida Keys living. Surrounded by swaying palms and coastal breezes, the property features inviting wraparound balconies--perfect for morning coffee or unwinding after a day on the water. Designed with boaters in mind, you'll appreciate the deep,

  Donna Pezzi Keller Williams Key West Compass Realty

  667 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /7

  $3,995,900

  New Construction $4K PRICE DROP

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

  231 E Shore Dr Unit 1, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 1, Summerland Key, FL 33042
• 

  

  /42

  $875,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  324 Airport Dr S, Summerland Key, FL 33042

  Rare opportunity to own a canal-front home directly on the private Summerland Cove Airport--where you can fly in, dock up, and be on open water in minutes. This solid CBS home offers 960 sq ft of elevated living space, currently configured as a spacious 1-bedroom, 1-bath upstairs (originally a 2-bedroom--easily converted back). Downstairs features a fully enclosed, permitted bonus area with an

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  324 Airport Dr S, Summerland Key, FL 33042
• 

  

  /55

  $2,299,999

  New Construction

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

  17210 Angelfish Ln, Summerland Key, FL 33042

  Experience the best of waterfront living in this brand-new home on Lower Sugarloaf Key. Thoughtfully designed and meticulously built, this 3-bedroom, 2.5-bath residence offers 2,288 square feet of modern coastal comfort. Situated on an expansive 16,445-square-foot lot, the property features a private seawall for direct boating access and a sparkling pool perfect for relaxing after a day on the

  The Spottswood Team Truman & Co. (KW)

  17210 Angelfish Ln, Summerland Key, FL 33042
• 

  

  /54

  $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
• 

  

  /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
• 

  

  /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
• 

  

  /60

  $175,000

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,120 Sq Ft

  27433 Antigua Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION CO-OWNERSHIP POOL HOME! 1/10 Shares. 8 Shares are still available for sale for this brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and

  Kelly Gardner Bluescape Real Estate

  27433 Antigua Rd, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /73

  $1,599,000

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

  1136 W Shore Dr, Big Pine Key, FL 33043

  Not a drive by- Must see inside and the back yard too.....Located on the West Side of the Island with excellent boating access this beautiful pool home is an entertainer's dream place. Stunning Sunsets & Sparkling waters for swimming, snorkeling, paddleboarding. Home features 3 bedroom suites with full baths plus a powder room too. Impact doors and windows, tile floors throughout, Viking

  Beata Sharpe Coldwell Banker Vanguard Realty

  1136 W Shore Dr, Big Pine Key, FL 33043
• 

  

  /22

  $839,000

  New Construction

  • 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 find: A spacious, open

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  27215 Mariposa Rd, Summerland Key, FL 33042
• 

  

  /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 approximate

  Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  1634 Lantana Ln, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /12

  $420,000

  • Land
  • 6,098 Sq Ft
  • $3,000,000 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
• 

  

  /21

  $575,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042

  Affordable piece of paradise! Fully furnished, move in ready, open concept, bright and airy, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you'll be amazed. All new furnishings included! It has a very large kitchen and living area that looks out over the canal, with sliding glass doors out on to the newly painted deck. Minisplits in each room that cool, heat and

  Mary Conklin Action Keys Realty of the Lower FL Keys LLC

  701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
• 

  

  /51

  $910,000

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

  813 Hawksbill Ln, Summerland Key, FL 33042

  Charming 2BR/2BA Keys home on Upper Sugarloaf. FULL HOUSE GENERATOR WITH TRANSFER SWITCH,Built on sturdy concrete pilings with Hardie board siding and a metal roof, Large workshop, storage space on first level with Laundry room, this three-story retreat of island living. Inside, you’ll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys

  Guadalupe Perez Douglas Elliman

  813 Hawksbill Ln, Summerland Key, FL 33042
• 

  

  /33

  $1,099,000

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

  1615 Fern Ave, Big Pine Key, FL 33043

  Welcome to this beautifully updated 3-bedroom, 2.5-bath waterfront home situated on a rare 12,000 sq. ft. double lot in the heart of Big Pine Key. Thoughtfully renovated throughout, this spacious two-story home offers bright, comfortable living with plenty of room for family and guests. Inside, you'll find a large living room filled with natural light, a versatile office/den, and an updated

  Taron Wirth Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  1615 Fern Ave, Big Pine Key, FL 33043
• 

  

  /43

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  27426 Martinique Ln, Summerland Key, FL 33042

  Oceanside canal-front home in the desirable Breezeswept Beach Estates neighborhood of Ramrod Key. This 3-bedroom, 2-bath residence features a private pool and is ideally positioned for enjoying the Florida Keys lifestyle, with quick access to world-class boating, fishing, diving, and snorkeling at nearby Looe Key Reef.The adjacent buildable lot is also included, offering buyers the

  Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  27426 Martinique Ln, Summerland Key, FL 33042
• 

  

  /7

  $4,375,000

  New Construction $50K PRICE INCREASE

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

  231 E Shore Dr Unit 3, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept layouts with 10'

  Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 3, Summerland Key, FL 33042
• 

  

  /16

  $320,000

  $5K PRICE DROP

  • Land
  • 4,356 Sq Ft
  • $3,200,000 per Acre

  27935 Tarpon Terrace, Summerland Key, FL 33042

  Heather Mason Coastal Collection Real Estate Inc.

  27935 Tarpon Terrace, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /19

  $1,750,000

  New Construction $250K PRICE INCREASE

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

  29558 Ranger Ave, Big Pine Key, FL 33043

  Experience the Ultimate Keys Lifestyle - New Construction with 75' of Waterfront on a Wide Boating CanalComing Fall 2025 - Nestled on a spacious 7,500 sqft lot (75x100) along a deep, wide boating canal, this brand new 1,500 sqft home offers the perfect blend of modern coastal living and exceptional boating access. With quick entry to Pine Channel, you're just minutes from both the Atlantic Ocean

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  29558 Ranger Ave, Big Pine Key, FL 33043
• 

  

  /6

  $499,000

  • Land
  • 6,969 Sq Ft
  • $3,118,750 per Acre

  22552 Jolly Roger Dr, Cudjoe Key, FL 33042

  Oceanfront lot in the Lower Keys overlooking Cudjoe Bay. Build your dream with expansive open-water views and ocean breezes. Prime waterfront setting with incredible potential. No current building permit; buyer to verify process and timelines. Rare opportunity to own a slice of paradise.

  Lauren Dunn Coldwell Banker Schmitt Islamorada

  22552 Jolly Roger Dr, Cudjoe Key, FL 33042

Showing Results 201 - 228, Page 6 of 6