Summerland Key, FL Homes for Sale with Pool

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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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  /33

  $255,000

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area.The home is clean and well cared for, offering a functional layout appropriate for full-time

  Bea Evelyn Citron Compass Florida, LLC

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
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  $859,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

  VACATION RENTAL OPPORTUNITY - OPEN WATER VIEWS + 43' DOCK - 2BR/2BA | 864 SQ. FT.Beautifully maintained 2-bedroom, 2-bath waterfront home offering open water views and excellent rental potential. This 864 sq. ft. property features a 43-foot dock with quick access to world-class boating, fishing, and diving in the Florida Keys. Ideal for investors or owners seeking a turn-key vacation rental

  Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
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  $1,380,000

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft

  30890 Granada Ave, Big Pine Key, FL 33043

  Welcome to your tropical oasis--where the true spirit of the Florida Keys comes to life. This spacious 3-bedroom waterfront home blends casual island style with relaxed coastal living, offering 1,764 square feet designed for comfort and ease. High ceilings lined with tongue-and-groove wood immediately set the island tone as you enter the open living space. The kitchen flows seamlessly into the

  Sunnie San Lorenzo Keyisle Realty

  30890 Granada Ave, Big Pine Key, FL 33043
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  /54

  $799,000

  • 2 Beds
  • 2 Baths
  • 640 Sq Ft

  701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042

  Luxurious Waterfront Living - Welcome to your perfect coastal oasis in the sought-after community of Venture Out! This contemporary high-rise boasts million-dollar views from every angle, including a screened patio for ultimate enjoyment. With an outside elevator providing easy access, this stunning home features a serene primary suite with stylish decor and a beautiful walk-in shower in the

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
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  /56

  $579,900

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042

  Introducing an exceptional waterfront investment opportunity in the heart of the Florida Keys! This beautifully remodeled waterfront home in the highly desirable gated community of Venture Out on Cudjoe Key is zoned for minimum one-day vacation rentals, making it an ideal choice for investors or those seeking a turnkey coastal retreat. Step inside and you'll immediately appreciate the home's

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
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  $2,069,000

  • 3 Beds
  • 2 Baths
  • 1,849 Sq Ft

  1733 Sunrise Dr, Big Pine Key, FL 33043

  Beautiful Waterfront Ocean & Canal property 3BD/2BA concrete block (CBS) direct ocean and canal access Property sits at 10 ft. elevation lot and features a durable aluminum roof, impact-resistant windows, and low-maintenance construction built for longevity in the Florida Keys. A 75 ft concrete dock, ideal for larger vessels, water toys, and fishing trips straight to open water. Spacious outdoor

  Norman De la Cruz Florida Realty of Miami Corp

  1733 Sunrise Dr, Big Pine Key, FL 33043
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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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  /59

  $535,000

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
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  /76

  $859,999

  • 2 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  19512 Aztec St, Summerland Key, FL 33042

  Motivated seller! Bring all Reasonable offers 2 bedrooms, 1.5 baths with a 500sq ft screened lanai in the main building. There are 2 additional buildings that could be used as offices or bedrooms. Custom Pool with jacuzzi and swim jet. Completely remodeled in 2020 with new roof, new A/C. Located in the established Indian Mound Estates neighborhood w/ Access to private boat ramp with cabana and

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  19512 Aztec St, Summerland Key, FL 33042
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  /18

  $445,000

  • Land

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

  Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

  Bea Evelyn Citron Compass Florida, LLC

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
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  /49

  $2,450,000

  • 3 Beds
  • 4 Baths
  • 2,087 Sq Ft

  31473 Warner St, Big Pine Key, FL 33043

  Welcome to an exquisite open-water retreat in Big Pine Key, an unparalleled blend of modern luxury and authentic Keys lifestyle. This completely updated and remodeled 3BD/4BA pool home offers panoramic water views from every angle, setting the stage for endless sunrises, sunsets, and starry nights. Designed with sophistication and comfort in mind, each bedroom is an ensuite, ensuring privacy and

  Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  31473 Warner St, Big Pine Key, FL 33043
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  /47

  $5,390,000

  • 3 Beds
  • 3 Baths
  • 4,687 Sq Ft

  3742 Seagrape St, Big Pine Key, FL 33043

  Escape to “The Castle”, a luxurious gated Gulf-front estate spanning 1.14 acres on Big Pine Key. Built in 2014 with poured concrete, impact windows/doors, elevator, and generator, this 4,600+ sq. ft. masterpiece offers 3 bedrooms, 3 baths, and breathtaking Gulf views. Boaters enjoy 235’ of dockage: 140’ protected canal dock with lift, ramp, and slip, plus 95’ open-water pier dock with lift and

  Jo Ann Cook Ocean Sotheby's International

  3742 Seagrape St, Big Pine Key, FL 33043
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  /55

  $329,000

  • 2 Beds
  • 1.5 Baths
  • 748 Sq Ft

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042

  Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental as

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
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  /30

  $430,000

  • 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

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
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  /46

  $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 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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  /24

  $259,000

  • Land

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

  RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

  Ian Calderwood Bluescape Real Estate

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
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  /73

  $1,699,000

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

  1136 W Shore Dr, Big Pine Key, FL 33043

  Seller says SELL IT! - 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

  Beata Sharpe Coldwell Banker Vanguard Realty

  1136 W Shore Dr, Big Pine Key, FL 33043
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  $1,349,000 New Construction

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

  335 Pirates Rd, Summerland Key, FL 33042

  *SWIMMING POOL TO BE BUILT IN SUMMER OF 2026*Escape to paradise with this incredible waterfront property located on a deep boating canal in the heart of the Lower Florida Keys. Perfectly suited for boating enthusiasts and water lovers, this home offers dockage and a boat lift, and direct, easy access to the open waters of the Atlantic Ocean and Gulf of Mexico, making it a dream come true for

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  335 Pirates Rd, Summerland Key, FL 33042
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  /32

  $2,100,000 New Construction

  • 5 Beds
  • 4 Baths
  • 2,886 Sq Ft

  662 Blackbeard Rd, Little Torch Key, FL 33042

  Pre-Construction Luxury Home | Jolly Roger EstatesIntroducing a rare pre-construction opportunity in the desirable waterfront community of Jolly Roger Estates. This CBS-built, fortress-like home is designed for durability, efficiency, and modern coastal living. The two-story floor plan offers 5 bedrooms, 4 bathrooms, and 2,886 square feet of living space, along with a spacious downstairs storage

  Lanny Gardner Bluescape Real Estate

  662 Blackbeard Rd, Little Torch Key, FL 33042
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  /18

  $1,349,000 New Construction

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

  27374 Guadaloupe Ln, Summerland Key, FL 33042

  New Construction coming Fall 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. 12x22 Swimming Pool and luscious landscaping.Inside the home: An open, airy floor plan that allows you to spread out and personalize your living space. A seamless

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  27374 Guadaloupe Ln, Summerland Key, FL 33042
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  /67

  $1,790,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,639 Sq Ft

  30985 Watson Blvd, Big Pine Key, FL 33043

  MODERN ISLAND RETREAT ON BOGIE CHANNEL - BIG PINE KEY, FLDiscover the epitome of Lower Keys living in this luxurious 4-bedroom, 3.5-bath CBS pool home, ideally positioned on Bogie Channel with direct BOATING access. Built in 2022 and offered furnished, this elevated residence combines modern design, coastal charm, and unmatched functionality. It's a rare find to own approximately .62 of an acre

  Donna Pezzi Keller Williams Key West Compass Realty

  30985 Watson Blvd, Big Pine Key, FL 33043
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  /110

  $2,800,000 New Construction

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  1553 Sunrise Dr, Big Pine Key, FL 33043

  Walk into this luxurious palace with captivating open water views. Light colors accenting the beautiful interior with matching large porcelain floors enhancing the large windows bringing the natural light inside. Gourmet kitchen for any chef to create great memories viewing the sunsets. Open patio with a great view of the pool and the outdoor entertaining areas. Three roomy suites for your family

  Barbara Eads Barbara Eads Realty

  1553 Sunrise Dr, Big Pine Key, FL 33043
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  /24

  $269,999 New Construction

  • 1 Bed
  • 1 Bath
  • 312 Sq Ft

  29859 Overseas Hwy Unit 37, Big Pine Key, FL 33043

  Welcome to easy island living in this 2021 Skyline Park Model Home located in the desirable Breeze Pines RV Estate. Thoughtfully designed, this 1-bedroom, 1-bath residence with a loft offers comfort, style, and functionality in a welcoming community setting. The home comes fully furnished and features a cozy fireplace, three mini-split A/C units for efficient climate control, and a well-equipped

  Halley Haack Coldwell Banker Schmitt RE Co.

  29859 Overseas Hwy Unit 37, Big Pine Key, FL 33043
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  /7

  $4,375,000 New Construction

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

  231 E Shore Dr Unit 6, 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 6, Summerland Key, FL 33042
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  /7

  $4,375,000 New Construction

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

  231 E Shore Dr Unit 4, 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 4, Summerland Key, FL 33042
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  /7

  $4,150,000 New Construction

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

  231 E Shore Dr Unit 2, 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 2, Summerland Key, FL 33042
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  /7

  $4,400,000 New Construction

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

  231 E Shore Dr Unit 5, 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 5, Summerland Key, FL 33042
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  /7

  $4,375,000 New Construction

  • 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
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  /7

  $3,995,900 New Construction

  • 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
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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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  /53

  $2,300,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  30995 Watson Blvd, Big Pine Key, FL 33043

  FINISHED -- NEW CONSTRUCTION!!! Luxury water view home with an in-ground pool on a 14,680 sq ft lot with dock and boating access. Brand new single level elevated CBS home over parking. Impact windows and doors, metal roof, 10-foot interior ceilings, stainless appliances and much more. Construction is completed, ready for occupancy.The property has a beautiful view over the water and a magnificent

  Banks Prevatt Coldwell Banker Schmitt RE Co.

  30995 Watson Blvd, Big Pine Key, FL 33043
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  /2

  $1,700,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft

  2211 San Sebastian Dr, Big Pine Key, FL 33043

  Brand New Home! Oversized Custom 4 bedroom 3 bath home located on a beautiful protected deep water canal with excellent access to the Gulf and Atlantic. This 2000 sq ft home is situated in a quiet neighborhood and features an open living area design with chef's kitchen/ quartz counter tops, high ceilings, covered porch, custom railings, impact windows and doors, custom concrete heated and chilled

  Greg MacLaren Internet Realty of the Florida Keys

  2211 San Sebastian Dr, Big Pine Key, FL 33043

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