Studio to 4 Bedroom Homes for Sale in Summerland Key, FL

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  /29

  $899,000

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

  463 Lesrohde Dr, Ramrod Key, FL 33042

  Don't miss the chance to own this exceptional piece of paradise--schedule a private showing today!Be the first to call this stunning, newly constructed Affinity-built home yours! Located in desirable Ramrod Key, this energy-efficient 3-bedroom, 2-bathroom residence boasts premium quality throughout. Featuring high-end fixtures, Pella impact-resistant windows and doors, and thoughtful

  Sarah Dolson Keller Williams Key West Compass Realty

  463 Lesrohde Dr, Ramrod Key, FL 33042
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  /54

  $1,850,000

  • 4 Beds
  • 3 Baths
  • 2,198 Sq Ft

  27365 Barbuda Ln, Summerland Key, FL 33042

  Located on an expansive double lot in Ramrod Key, this stunning 4-bedroom, 3-bath canal-front retreat blends luxury, comfort, and true Florida Keys living. With quick boating access, a 10,000 lb boat lift, and a dedicated fish cleaning station, this home is a dream for anglers and boating enthusiasts alike. Step inside and enjoy a bright, coastal-inspired layout with plenty of room for family and

  Halley Haack Coldwell Banker Schmitt RE Co.

  27365 Barbuda Ln, Summerland Key, FL 33042
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  /125

  $1,190,000

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  22748 Blackbeard Ln, Cudjoe Key, FL 33042

  Welcome home to this impressively spacious 2-bedroom, 2-bath Keys retreat, offering an elevated blend of comfort, functionality, and coastal living. The outdoor living space is a dream with a new concrete pool & waterfall feature, 12k lb boat lift, 60' concrete seawall, & an expansive 10 foot deep back porch (total of nearly 700 sq ft of porches), all perfect for outdoor dining, lounging, &

  Lindsay Ryan EXP Realty LLC

  22748 Blackbeard Ln, Cudjoe 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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  /30

  $524,000

  • 2 Beds
  • 1 Bath
  • 1,253 Sq Ft

  31541 Avenue A, Big Pine Key, FL 33043

  Welcome to this Key West-style home located on Big Pine Key! Situated on a generous 7500 square-foot fully fenced lot, this property offers ample space for parking and storage, making it a perfect island retreat for those looking to escape the hustle and bustle. As you step inside, you'll be greeted by the cozy charm of two bedrooms and a well-appointed bathroom, providing a comfortable living

  Melissa Graham Bluescape Real Estate

  31541 Avenue A, Big Pine Key, FL 33043
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  /52

  $425,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

  Vacation Rental Property with Transient Rentals Allowed! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen,

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
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  /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
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  /45

  $1,295,000 Open Sun 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft

  17144 Coral Dr, Summerland Key, FL 33042

  Located in prestigious Sugarloaf Shores, a coastal community of waterfront homes just 15 miles from the magic of Key West. As you enter the 3-bedroom, 2-bath home, a massive Great Room with a cathedral ceiling will greet you, highlighted by remodeled cabinetry, kitchen, and stainless steel appliances, including a gas range, where friends and family can gather. Enjoy the full-length porch

  Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  17144 Coral Dr, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /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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  /43

  $625,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

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

  Affordable piece of paradise! 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 dehumidify! Plus, a 5

  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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  /34

  $1,789,000

  • 4 Beds
  • 3 Baths
  • 2,323 Sq Ft

  31450 Avenue G, Big Pine Key, FL 33043

  This expansive 4 bedroom, 3 bathroom home offers over 2,300 sq ft of solid concrete construction, built in 2023 with hurricane impact windows/doors and a metal roof for total peace of mind.Step inside to a bright, open-concept floor plan with sleek tile flooring throughout. Prepare your Keys Fresh Catch in your Chef's Kitchen with custom cabinets and quartz countertops. The massive master suite

  Solaris Gregory Expert Realty LLC (HQ)

  31450 Avenue G, Big Pine Key, FL 33043
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  /32

  $1,689,000

  • 3 Beds
  • 2 Baths
  • 2,144 Sq Ft

  1151 Sugarloaf Blvd, Summerland Key, FL 33042

  Truly unique and private estate property on the desired Sugarloaf Blvd. in Sugarloaf Shores. Ground level CBS house sits on 2 waterfront lots. Totaling over 1.3 acres of land and approx. 400 ft. of canal front. Amazing view up the canal to the open water. The large floor plan featuring 3 bedrooms, 2 baths, den/office and fireplace. Kitchen has stainless appliances, quartz countertops and lots of

  Wendy Zintsmaster Truman & Co. (KW)

  1151 Sugarloaf Blvd, Summerland Key, FL 33042
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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 with 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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  /30

  $975,000

  • 3 Beds
  • 3 Baths
  • 1,492 Sq Ft

  31490 Avenue F, Big Pine Key, FL 33043

  This all-concrete, meticulously designed 3-bedroom, 2.5-bath home offers both luxury and functionality. Featuring impact windows and doors and a durable metal roof, this home provides peace of mind and protection for years to come. The open-concept living area is perfect for both relaxation and entertaining, with a modern kitchen boasting quartz countertops and stainless steel appliances. The

  Austin Kimbler Expert Realty LLC (HQ)

  31490 Avenue F, Big Pine Key, FL 33043
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  /18

  $1,275,000

  • 3 Beds
  • 1 Bath
  • 1,043 Sq Ft

  550 Pine Ln, Big Pine Key, FL 33043

  This newly remodeled 2-bedroom, 1-bathroom home is perfectly positioned on two spacious lots in the heart of Big Pine Key, offering over 20,000 sq ft of land and an incredible 297 feet of waterfront. With 75 feet of concrete dockage and quick access to the ocean via Spanish Harbor Channel, this is a boater's dream come true.Inside, enjoy peace of mind with impact-rated windows and doors, a sturdy

  Justyn Ewald Expert Realty LLC (HQ)

  550 Pine Ln, Big Pine Key, FL 33043
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  /98

  $2,800,000

  • 3 Beds
  • 3 Baths
  • 3,013 Sq Ft

  680 Cruikshank Island, Summerland Key, FL 33042

  Welcome to 680 Cruikshank Isle, an extraordinary waterfront estate in the heart of Summerland Key that captures the essence of Florida Keys luxury living. Offering over 3,000 sq. ft. of interior space, this three-bedroom, three-bath residence is thoughtfully designed for both elegance and comfort, blending open living areas with timeless architectural details.Inside, soaring ceilings and

  Barbara Crespo Keller Williams Key West Compass Realty

  680 Cruikshank Island, Summerland Key, FL 33042
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  /43

  $1,795,000

  • 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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  /79

  $1,999,999

  • 4 Beds
  • 3.5 Baths
  • 2,422 Sq Ft

  17054 Coral Dr, Summerland Key, FL 33042

  Waterfront retreat in prestigious Sugarloaf Key, just 20 mins from Key West! This 4BD/3BA home sits on a 12,500 sq ft lot with 100' of seawall, davits, and wide canal access—just one in from open water. Enjoy a split-bedroom layout with two primary suites, an open kitchen with stainless appliances, and a theater room. Outdoor living shines with covered entertaining space, custom bar, fire pit,

  Will Langley Berkshire Hathaway Knight & Gardner Realty

  17054 Coral Dr, Summerland Key, FL 33042
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  /35

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,420 Sq Ft

  2231 Middle Torch Rd, Summerland Key, FL 33042

  Opportunities like this are few and far between. This extraordinary offering includes two adjoining 2.5-acre parcels, totaling 5 acres of land -- Truly a rare find in the Florida Keys. Each lot measures 110 x 990 feet, offering an abundance of space, privacy, and potential.The property features two dwellings -- a single-family residence and a manufactured dwelling on the other -- each with 1

  Stephany Duvall Engel & Volkers Marathon

  2231 Middle Torch Rd, Summerland Key, FL 33042
• 

  

  /19

  $1,499,999 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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  /26

  $268,000

  • 2 Beds
  • 1 Bath
  • 664 Sq Ft

  701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042

  2 bedroom 1 bath mobile home located at 701 Spanish Main Dr Lot #457 Cudjoe Key FL in Venture Out, an individually owned residential condominium community with 24hr gated security located 20 miles from world famous Key West. This mobile home is on a non-waterfront lot w/ a peek-a-boo view of eastern facing canal. Other ideal use as a ROGO exempt buildable lot for a new elevated home. No age

  Deirdre Praught Florida Keys Realty, Inc.

  701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042
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  /54

  $899,000

  • 2 Beds
  • 2 Baths
  • 998 Sq Ft

  2123 Spanish Channel Dr, Big Pine Key, FL 33043

  Ocean Views, Direct canal frontage , in the ocean water in 2 minutes. Concrete Dock, Solid pour concrete column house is ready for making your own . Beautiful trees, planted newly landscaped with custom design fencing. Wildlife is amazing, quiet location near end of the road. Grocery store 1 mile away close to Key West or Marathon Roof replaced in 2018 also all new hurricane window, doors,

  Anne Press Lokation Real Estate

  2123 Spanish Channel Dr, Big Pine Key, FL 33043
• 

  

  /25

  $349,000

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft

  27944 Tarpon Terrace, Little Torch Key, FL 33042

  Don't miss this amazing opportunity to own a great piece of waterfront property on a clean plugged canal. Excellent for swimming, kayaking, paddle boarding, fishing and snorkeling in your own backyard. This well maintained updated home has stainless steel appliances with an ample amount of cabinets in the kitchen and a nice bright open living room. Just a few steps down the hall, is your comfy

  Tracy Shields KeyIsle Realty

  27944 Tarpon Terrace, Little Torch Key, FL 33042
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  /22

  $742,000

  • 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

  Kristen Brenner/Margie Casey T Florida Keys Real Estate Group

  3943 Venna Rd, Big Pine Key, FL 33043
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  /86

  $1,939,000

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

  16640 Cypress Rd, Summerland Key, FL 33042

  RARE Solar-Powered Waterfront Tropical Gem with TESLA Storage Banks on Prestigious Sugarloaf Key! A rare opportunity to own a fully solar-powered waterfront residence featuring 26 solar panels and two Tesla Powerwall storage banks, offering exceptionally low energy costs, backup power, and the potential to earn credits by supplying excess energy back to the grid. This elevated 3 BD, 2 BA, 1,764

  Lisa Swanson The Agency Florida Keys

  16640 Cypress Rd, Summerland Key, FL 33042
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  /42

  $1,299,000

  • 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
• 

  

  /32

  $1,099,000

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  17137 Bonita Ln W, Summerland Key, FL 33042

  Enjoy this ideal custom built Keys home located in beautiful Sugarloaf Shores! A very welcoming home with 3 bedrooms, 2 baths and a lovely enclosed porch with a captivating tong and groove ceiling. Attractive wood flooring throughout the living room, dining area and bedrooms with tile in the kitchen and baths. Two solid wide staircases lead up to the main entrance and another descending to

  Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  17137 Bonita Ln W, Summerland Key, FL 33042
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  /27

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,070 Sq Ft

  18 W Circle Dr, Key West, FL 33040

  This beautifully remodeled 3-bedroom, 2-bath stilted home sits canal-side behind Baby's Coffee, offering open water views and great opportunity. Built in 2000, it features a durable metal roof, impact windows, and sliding glass doors for comfort and great insurance options. Launch your boat from your own private ramp or use the community ramp nearby, then relax in the sparkling pool or tinker in

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 783-6419

  18 W Circle Dr, Key West, FL 33040
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  /9

  $472,000

  • 2 Beds
  • 1 Bath
  • 460 Sq Ft

  6 Beach Dr, Key West, FL 33040

  Rare DOUBLE LOT on OPEN WATER with BOATING ACCESS and ROGO EXEMPT LETTER IN HAND!! This lot can be cleared providing huge wide water sunset views and the ability to add dockage with shallow boating access. Located in the Saddlebunch Keys, just 10 minutes from all of the superior dining and nightlife of Key West, Florida. Repair trailer that is on site under the 50% rule, or build your dream home

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 756-8747

  6 Beach Dr, Key West, FL 33040
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  /44

  $837,000

  • 3 Beds
  • 3 Baths
  • 1,380 Sq Ft

  57 Palm Dr, Key West, FL 33040

  Tropical Waterfront Oasis - Affordable Island Living Just 15 Mins from Key West.Discover the perfect blend of adventure, comfort and peace of mind in this elevated 3-bedroom, 3 bath coastal retreat, located in one of the Lower Keys most affordable and family friendly neighborhoods. Just a short 15 min drive to Key West, this move-in ready home is freshly painted and waiting for your next chapter

  Suzanne Moore Suzanne Moore Real Estate

  57 Palm Dr, Key West, FL 33040
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  /15

  $425,000

  • 2 Beds
  • 1 Bath
  • 798 Sq Ft

  69 Palm Dr, Key West, FL 33040

  ROGO exempt! Opportunity to easily replace existing mobile with a hurricane-rated modular, wood frame or Concrete home in a relaxed Lower Keys community just 15 minutes from Key West. Located on a 60+ ft wide deep-water canal with a solid seawall that spans the width of the property, 35 feet--ideal for boating or fishing right from your backyard. Enjoy neighborhood amenities like tennis and

  Natallie Liz Expert Realty LLC (HQ)

  69 Palm Dr, Key West, FL 33040
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  /18

  $119,000

  • 1 Bed
  • 1 Bath
  • 357 Sq Ft

  38801 Overseas Hwy Unit 153, Big Pine Key, FL 33043

  This is your chance to own your very own vacation cottage at a top rated Florida Keys RV resort. This cottage is fully set-up onsite and comes fully furnished. The Island Cottage features a fully equipped kitchenette, LED SmartTVs, central air conditioning, and a full bath. Enjoy your island view of paradise from your covered porch. You'll have access to top notch amenities and activities: Scuba

  Michael Weber

  38801 Overseas Hwy Unit 153, Big Pine Key, FL 33043
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  /51

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,372 Sq Ft

  56 Bay Dr, Saddlebunch, FL

  Island Life, unequalled waterfront sunsets, ocean breezes and crystal clear waters. And you can drive to your Caribbean Island Escape! This location is exceptional on all fronts, more than 2X the avg lot size, a craftsman remodeled 3/2 converted to a 2/2 with a spacious convertible home office, gorgeous high quality materials throughout, including Walnut Engineered Flooring, Brazilian Quartzite

  Stephanie Wise Keller Williams Key West Compass Realty

  56 Bay Dr, Saddlebunch, FL
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  /113

  $1,999,999

  • 4 Beds
  • 4 Baths
  • 2,454 Sq Ft

  78 Bay Dr, Key West, FL 33040

  Set on a quater-acre lot in Bay Point, a quiet residential enclave celebrated for its natural surroundings, water views, and relaxed tropical lifestyle, this waterfront estate embodies the very best of Keys living. Residents enjoy the serenity of a low-density neighborhood framed by mangroves and open water, while remaining just minutes from the world-class dining, shopping, and entertainment of

  Jenny Benson Coastal Collection Real Estate Inc.

  78 Bay Dr, Key West, FL 33040
• 

  

  /19

  $699,000

  • 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
• 

  

  /42

  $574,000

  • 2 Beds
  • 2 Baths
  • 873 Sq Ft

  4 Coral Dr, Key West, FL 33040

  Cash Credit for New Metal Roof Available with reasonable offer! VA Assumable Rate at 3.5% for eligible Buyers!Own your own slice of the Keys! This efficient 2-bedroom, 2-bath home offers comfort, functionality, and a wonderful outdoor lifestyle. The inviting floor plan flows easily between the living, dining, and kitchen areas, making everyday living and entertaining effortless. Step outside to a

  Lindsay Ryan EXP Realty LLC

  4 Coral Dr, Key West, FL 33040

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