Waterfront Homes for Sale in Summerland Key, FL

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  /9

  $2,400,000

  • Land
  • 0.55 Acre
  • $4,356,000 per Acre

  24356 Overseas Hwy, Summerland Key, FL 33042

  Begin your Florida Keys venture at this exceptional waterfront Commercial property. The site consists of four lots measuring 60'x100' each, creating a 24,000-square-foot parcel with 240 feet of concrete seawall. The property comes equipped with water and electrical connections. Its strategic location offers excellent access to both the Atlantic and Gulf waters, including proximity to Looe Key

  Scott Brisson KeyIsle Realty

  24356 Overseas Hwy, Summerland Key, FL 33042
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  /56

  $2,200,000 Open House 2/28

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft

  1631 Sunrise Dr, Big Pine Key, FL 33043

  Seller motivated and furnishings can convey. This 2023 new construction waterfront home in Tropical Bay Estates offers luxury coastal living with stunning sunrise and water views from nearly every room. Built with full CBS construction on 10-foot stilts, it features 10-foot ceilings, 8-foot doors, impact windows, and a metal roof for durability and storm protection. The 2,000+ sq ft open floor

  Hector Vazquez Premium Properties Real Estate

  1631 Sunrise Dr, Big Pine Key, FL 33043
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  /83

  $4,400,000

  • 4 Beds
  • 4.5 Baths
  • 2,907 Sq Ft

  16745 Tamarind Rd, Sugarloaf Shores, FL 33042

  Step into your own waterfront sanctuary, 'Casa Del Mar' in prestigious Sugarloaf Shores on Lower Sugarloaf Key, where clean, modern design meets unmistakable Florida Keys ease. This beautifully built CBS home with impact windows delivers 4 spacious bedrooms and 4.5 baths, wrapped in contemporary style and coastal charm.Inside, the heart of the home is a true chef's kitchen with high-end

  Carlos Lorenzo American Caribbean Real Estate, Christie's International Real Estate

  16745 Tamarind Rd, Sugarloaf Shores, FL 33042
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  /40

  $1,250,000

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft

  857 Caribbean Dr E, Summerland Key, FL 33042

  HOME is where the BOAT IS!Discover effortless access to world-class boating on one of the widest, deepest, and most desirable canals in the Lower Keys. Your 17,000-lb boat lift sits on a pristine flow-through canal--meaning clean, clear water and quick access. In just minutes, you can be fishing the Atlantic, exploring the backcountry in the Gulf, or gliding toward a perfect Key West sunset.This

  Donna Pezzi Keller Williams Key West Compass Realty

  857 Caribbean Dr E, Summerland Key, FL 33042
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  /16

  $499,000

  • Land
  • 0.44 Acre
  • $1,141,020 per Acre

  Vacant Lot Canal St, Big Pine Key, FL 33043

  Prime Commercial Fishing Property in the Florida Keys!Discover a rare opportunity to own and operate a commercial fishing business in the coveted Commercial Fishing Special District of Big Pine, FL. This unique zoning allows unparalleled access to open water, making it a fisherman's paradise. Here are the highlights:- Buildable Property: Your vision can come to life with ease on this buildable

  Sam Williams Coldwell Banker Schmitt Real Estate Co.

  Vacant Lot Canal St, Big Pine Key, FL 33043
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  /30

  $460,000

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

  Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
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  /15

  $1,495,000

  • Land
  • 2.29 Acres
  • $652,838 per Acre

  1261 Avenue A, Big Pine Key, FL 33043

  NO WAIT TO BUILD!! ROGO Exempt 2.29 private and exclusive estate acreage with Bay Bottom on Bogie Channel with spectacular open water views. Property rests at the end of a quiet street and neighbors a park. USACE permitted a 412' dock before the pandemic that recently expired but is in discussion for renewal. Former home on property was damaged in Hurricane Irma and has since been demolished and

  Sasha Naimi Charles Rutenberg Realty FTL

  1261 Avenue A, Big Pine Key, FL 33043
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  /46

  $487,000 Open Mon 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

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

  Seller is motivated!Coastal Charm Meets Modern Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key--a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright and airy

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
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  /31

  $740,000

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  4099 Egret Ln, Summerland Key, FL 33042

  Excellent Investment Opportunity! Classic waterfront home in quiet Big Torch Key. This home features 2 bedrooms, two bathrooms and a spacious open living/dining/kitchen area. Water from a 12k gallon cistern with a reverse osmosis system. City water is available and the home is connected to sewer. This home is being sold as a life estate. The homeowner will remain in place after purchase of the

  Banks Prevatt Coldwell Banker Schmitt RE Co.

  4099 Egret Ln, Summerland Key, FL 33042
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  /7

  $3,995,900 Open Sat 11AM - 3PM

  • 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 Muzzillo Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 1, Summerland Key, FL 33042
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  /41

  $840,000

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft

  3635 Trade Winds 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 dock with no bridges to the ocean, ideal for quick access to the water. Located in a quiet neighborhood, this home features a 2018 roof,

  Michel Luna Lifestyle International Realty

  3635 Trade Winds St, Big Pine Key, FL 33043
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  /60

  $175,000 Open Mon 11AM - 1PM

  • 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
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  /41

  $840,000

  • 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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  /17

  $1,449,000 New Construction

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

  27355 Guadaloupe Ln, Ramrod Key, FL 33042

  New Construction coming Spring 2026. Step into the laid-back charm of the Florida Keys with this spacious 1,500 sqft home, perfectly situated along a peaceful boating canal in the Lower Keys, a short boat ride out to Looe Key Reef. Inside the home: An open, airy floor plan that allows you to spread out and personalize your living space. A seamless connection between indoor and outdoor living,

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  27355 Guadaloupe Ln, Ramrod Key, FL 33042
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  /16

  $989,999

  • 3 Beds
  • 3 Baths
  • 960 Sq Ft

  22961 John Avery Ln, Summerland Key, FL 33042

  Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower

  Rayden Vega CASA MIAMI REAL ESTATE

  22961 John Avery Ln, Summerland Key, FL 33042
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  /44

  $1,199,000

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

  27426 Martinique Ln, Summerland Key, FL 33042

  Oceanside canal-front opportunity in Ramrod Key. This 3-bedroom, 2-bath home with a pool is ideally located near Looe Key Reef and Picnic Island, and is just a 10-minute walk to the local watering hole, The Tiki.The property includes an additional buildable lot, creating a rare opportunity to construct a second residence, guest house, or future income-producing property--significantly enhancing

  Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  27426 Martinique Ln, Summerland Key, FL 33042
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  /6

  $825,000

  • 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
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  /23

  $3,750,000

  • 4 Beds
  • 4.5 Baths
  • 3,228 Sq Ft

  22815 Port Royal Ln, Summerland Key, FL 33042

  DIRECT OCEAN FRONT 323FT of Water Frontage- BOATERS PARADISE FOUND w/room for 3 Boats on unobstructed sunset view over open water - oversized corner lot with water on 2 sides at end of a private road offering picture perfect sunsets in a protected bay! INCOME PRODUCING!, includes 175' of open water and 148' of canal frontage featuring a 90' concrete dock, and a private kayak launch. The main

  Rhonda Gailey Gailey Enterprises Real Estate

  22815 Port Royal Ln, Summerland Key, FL 33042
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  /43

  $1,785,000

  • 3 Beds
  • 3 Baths
  • 1,837 Sq Ft

  30363 Flamingo Ln, Big Pine Key, FL 33043

  Tranquility meets coastal living, discover this stunning concrete constructed home built in 1993. Located in the desirable subdivision of Tropical Bay Estates this elevated waterfront residence offers unparalleled access to both the ocean and bay, just 15 minutes by boat. The iconic No Name Pub is just a 2-minute drive or a 15-minute walk away for some of the best pizza in the Keys. A few

  Jo Ann Cook Ocean Sotheby's International

  30363 Flamingo Ln, Big Pine Key, FL 33043
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  /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
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  /15

  $250,000

  • Land

  27057 Angelfish Rd, Ramrod Key, FL 33042

  6000 square foot lot with a building permit IN-PROCESS for a 3 bedroom / 2 bath stilted single family residence. 1320 square feet. The plans are for an Affinity home with features that include impact doors and windows and built to 180 mph with a cistern and designed using the Green Building code. Great for the environment, great for your insurance rates.Located a bike ride away from Boondocks

  Donna Pezzi Keller Williams Key West Compass Realty

  27057 Angelfish Rd, Ramrod Key, FL 33042
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  /7

  $4,375,000 Open Sat 11AM - 3PM

  • 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 Muzzillo Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 3, Summerland Key, FL 33042
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  /17

  $450,000

  • Land

  132 Blackbeard Rd, Little Torch Key, FL 33042

  This beautiful oversized lot is located in Jolly Rogers Estates, Little Torch Key. Corner lot with two sides of canal front with some open water views. The seller is in the process of obtaining a building permit for a 1227 sq ft 3 bedrooms & 2 baths, Modular Home. The building department has the property ranked with 41 points. Buyer to finish the permitting process. Enjoy quick boating access to

  Halley Haack Coldwell Banker Schmitt RE Co.

  132 Blackbeard Rd, Little Torch Key, FL 33042
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  /11

  $480,000

  • Land

  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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  /19

  $1,750,000 New Construction

  • 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
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  /22

  $715,000

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  3943 Venna Rd, Big Pine Key, FL 33043

  Welcome to your island retreat in the sought-after community of Port Pine Heights on Big Pine Key. This charming stilted waterfront home offers quick boating access to Pine Channel, perfect for those who love life on the water. Families are drawn to this serene neighborhood for its privacy, friendly Key Deer, and close proximity to No Name Key, as well as the sparkling beaches and crystal-clear

  Thomas Carden Keys to the Coast Real Estate LLC

  3943 Venna Rd, Big Pine Key, FL 33043
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  /13

  $895,000

  • Land
  • 0.34 Acre
  • $2,643,849 per Acre

  30988 Witters Ln, Big Pine Key, FL 33043

  Beautiful extra large lot with open water view and full active building permit. The lot also has an active permit for in-ground pool. Plans are included for single level elevated CBS 4 Bedroom 4.5 Bathroom luxury home over parking, with superb boating access to both the Atlantic Ocean and Gulf of Mexico.

  Banks Prevatt Coldwell Banker Schmitt RE Co.

  30988 Witters Ln, Big Pine Key, FL 33043
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  /42

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft

  29662 Independence Ave, Big Pine Key, FL 33043

  Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home nestled on a double-fenced lot in Big Pine Key. Perfectly positioned along a scenic canal, this property offers Southern charm, with an inviting wraparound porch to enjoy the gentle breeze and picturesque views. This home is ideal for both relaxation and entertaining.Step outside to a seawall that leads

  Karen Haack Coldwell Banker Schmitt RE Co.

  29662 Independence Ave, Big Pine Key, FL 33043
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  /45

  $4,375,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,103 Sq Ft

  231 E Shore Dr Unit 3, Key West, FL 33040

  Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available—each starting at $4 million—this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West. Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5

  Stephanie Muzzillo Serhant

  231 E Shore Dr Unit 3, Key West, FL 33040
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  /16

  $4,375,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,103 Sq Ft

  231 E Shore Dr Unit 5, Key West, FL 33040

  Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available—each starting at $4 million—this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West. Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5

  Stephanie Muzzillo Serhant

  231 E Shore Dr Unit 5, Key West, FL 33040
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  /47

  $4,250,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,103 Sq Ft

  231 E Shore Dr Unit 2, Key West, FL 33040

  Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available—each starting at $4 million—this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West. Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5

  Stephanie Muzzillo Serhant

  231 E Shore Dr Unit 2, Key West, FL 33040
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  /54

  $1,599,000

  • 4 Beds
  • 3 Baths
  • 1,633 Sq Ft

  34 Bay Dr, Key West, FL 33040

  Experience refined Florida Keys living in this fully renovated canal-front residence offering privacy, quality craftsmanship and effortless coastal elegance. Located just 15 minutes from Key West this ground- level home is set on an expansive 15,047 sq. ft. lot with a fully fenced yard creating a serene and private setting.Designed for the flats fisherman boating enthusiast the property features

  Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  34 Bay Dr, Key West, FL 33040
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  /19

  $694,000

  • 2 Beds
  • 2 Baths
  • 1,010 Sq Ft

  4 Shore Dr, Key West, FL 33040

  Million dollar views! Ocean and Gulf views make this an affordable waterfront gem. Situated in the quiet and peaceful Bay Point neighborhood, this home is only 17 miles from Key West allowing quick city access and return to waterfront bliss. This Keys-style fish camp offers a waterfront manufactured home with 2 bedrooms and 2 baths. The side yard was once an orchid house and could be returned as

  Elizabeth Jolin Coldwell Banker Schmitt Islamorada

  4 Shore Dr, Key West, FL 33040
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  /39

  $4,375,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,103 Sq Ft

  231 E Shore Dr Unit 6, Key West, FL 33040

  Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available—each starting at $4 million—this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West. Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5

  Stephanie Muzzillo Serhant

  231 E Shore Dr Unit 6, Key West, FL 33040

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