Homes for Sale near Key West High School

• 

  

  

  /46

  $4,350,000

  • 4 Beds
  • 4 Baths
  • 2,458 Sq Ft

  3 Evergreen Ave, Key West, FL 33040

  Experience the ultimate Key West lifestyle in this new construction (2025) waterfront home in the exclusive Key Haven community. Situated on the coveted final canal, this 4BR+office/4BA entertainer's paradise offers 2,458 sqft of luxury living and 2,400 sqft of covered outdoor space. This home features a completely private top-floor guest quarters offering ultimate flexibility--perfect as a

  Steven Koleno Beycome of Florida, LLC

  3 Evergreen Ave, Key West, FL 33040
• 

  

  

  /25

  $1,049,000

  • 3 Beds
  • 3 Baths
  • 1,740 Sq Ft

  1210 Virginia St, Key West, FL 33040

  Currently this is a two-story duplex in the popular Bayview Park neighborhood in Old Town. It could be converted back to the original single-family home. There are a total of three bedrooms and 2.5 baths. As currently configured, the first floor has 2 bedrooms,1.5 baths and features 9.5-foot ceilings, doors with transom windows, and hardwood floors. French doors open to the rear yard and porch.

  The Behmke Group Keller Williams Key West Compass Realty

  1210 Virginia St, Key West, FL 33040
• 

  

  

  /44

  $6,850,000

  • 3 Beds
  • 3 Baths
  • 4,200 Sq Ft

  103 Front St, Key West, FL 33040

  103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. A dramatic staircase leads to a second floor walkway which is open to the main level. On one end is

  Laura McChesney Preferred Properties (KW)

  103 Front St, Key West, FL 33040
• 

  

  

  /60

  $1,490,000 New Construction

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

  27433 Antigua Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION POOL HOME - COMPLETED 2025 & MOVE-IN READY!Welcome to your 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 impact-rated windows & doors,

  Kelly Gardner Bluescape Real Estate

  27433 Antigua Rd, Summerland Key, FL 33042
• 

  

  

  /25

  $634,900

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

  31243 E Ave E, Big Pine Key, FL 33043

  **Price Enhancement* Welcome to your slice of paradise in Big Pine Key! This charming 3-bedroom, 2-bath home is an ideal opportunity for families or first-time homebuyers seeking the quintessential Florida Keys lifestyle. Step inside to discover a comfortable and inviting living space, perfect for creating lasting memories.Outside, a small, fenced area provides a safe and convenient space for

  Sabre Mendoza Coldwell Banker Schmitt RE Co.

  31243 E Ave E, Big Pine Key, FL 33043
• 

  

  /22

  $1,675,000

  • 2 Beds
  • 2 Baths
  • 1,002 Sq Ft

  404 Porter Ln Unit 16, Key West, FL 33040

  404 Porter Lane is located in the sought after Porter Court community inside the Truman Annex. Duval, shops and restaurants are only a short stroll away. Homes rarely come on the market at Porter Court and 404 Porter Lane is a rare find. This corner unit is flooded with natural light from windows on three sides. It features private front and rear porches plus a separate gate to the deeded

  Laura McChesney Preferred Properties (KW)

  404 Porter Ln Unit 16, Key West, FL 33040
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  /88

  $750,000

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  40 Munson Ave, Summerland Key, FL 33042

  Welcome home to your peaceful island retreat! This stunning 3-bed, 2-bath home is move-in ready & full of charm. Enjoy soaring vaulted ceilings, an open layout, & a bright kitchen with Quartz countertops, stainless steel appliances, & large island with ample seating. Recent updates include new luxury vinyl plank flooring, new upgraded refrigerator, & new outdoor bar & sitting area perfect for

  Lindsay Ryan EXP Realty LLC

  40 Munson Ave, Summerland Key, FL 33042
• 

  

  /60

  $949,900

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  27405 Guadaloupe Ln, Summerland Key, FL 33042

  Soak up the Keys lifestyle from this bright, modern 3-bed/2-bath home in the coveted oceanside community of Breezeswept Beach Estates on Ramrod Key. Built in 2008 with high-end finishes--sleek cabinetry, quality flooring, and fresh, airy decor--this turnkey residence is neat, clean, and move-in ready.Outdoor living shines here: two open decks (front and back) capture breezes and sunset glow,

  Mark Gable Engel & Volkers Marathon

  27405 Guadaloupe Ln, Summerland Key, FL 33042
• 

  

  /39

  $699,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  30881 Witters Ln, Big Pine Key, FL 33043

  Updated cottage with all the necessities you need with minimal maintenance. This CBS home has a newer metal roof, mini split A/c, updated kitchen on 3 lots only a very short ride to Boggie Channel, the only market channel to the Atlantic and Gulf in the Lower Keys. This is a great opportunity for boaters and naturalist as this is only a short walk or kayak to No Name Key and surrounding waters

  John Nazzaro Keller Williams Realty Premier Properties - Kendall

  30881 Witters Ln, Big Pine Key, FL 33043
• 

  

  /23

  $675,000

  • 2 Beds
  • 1 Bath
  • 643 Sq Ft

  409 Margaret St Unit 202 / B, Key West, FL 33040

  Close to the Historic Seaport, restaurants, art galleries, and more!. Recently renovated, this 2 bedroom, 1 bath condo has high impact windows and door, washer/ dryer, tankless hot water heater, new flooring, kitchen, mini splits, appliances, and is being sold furnished! Prime Old Town location, walk or bike to everything! This is easy island living- close to everything, and no need for a car.

  Elaine Coyle Keller Williams Key West Compass Realty

  409 Margaret St Unit 202 / B, Key West, FL 33040
• 

  

  /48

  $1,700,000

  • 3 Beds
  • 5 Baths
  • 1,442 Sq Ft

  1001 United St Unit B, Key West, FL 33040

  Enjoy your tropical retreat in the heart of Old Town Key West with this stunning, fully remodeled, three-story corner lot island oasis. The first floor of this expansive attached home welcomes you with soaring vaulted ceilings, an open floor plan drenched in natural light, and seamless indoor-outdoor living. Throw open the French doors and lounge on your poolside veranda, or take a dip in the

  Michael Sorah Truman & Co. (KW)

  1001 United St Unit B, Key West, FL 33040
• 

  

  /54

  $1,900,000

  • 4 Beds
  • 3 Baths
  • 1,440 Sq Ft

  1082 Bay Dr, Summerland Key, FL 33042

  Rare Yacht-Ready Waterfront? It doesn't get better than this in the Lower Florida Keys! Embraced by the emerald waters of the American Caribbean, pristine, wide and flow-through canals, and nearly 200 feet of concrete seawall sits this extraordinary opportunity to own prime waterfront. A prized combination coveted by the most discerning boating enthusiasts. Sitting on an oversized 7,900 sq. ft.

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  1082 Bay Dr, Summerland Key, FL 33042
• 

  

  /30

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3930 S Roosevelt Blvd Unit E104, Key West, FL 33040

  Welcome to Las Salinas Unit E104 - a beautifully updated 3-bedroom, 2-bath condo offering a turnkey lifestyle in Key West. Recently painted, brand new hot water tank (2025), and carefully maintained, this unit is move-in ready with no deferred maintenance to worry about. Furnishings are negotiable too, making it even easier to settle in and start enjoying island life right away. Inside, you'll

  Ted Stewart Truman & Co. (KW)

  3930 S Roosevelt Blvd Unit E104, Key West, FL 33040
• 

  

  /19

  $2,095,000

  • 8 Beds
  • 4 Baths
  • 3,383 Sq Ft

  905 Grinnell St, Key West, FL 33040

  Located in the heart of Key West's Historic District, 905 Grinnell Street is a distinctive multi-unit property that blends architectural character with strong investment performance. Originally built as a church, the structure has been thoughtfully converted into four residential units totaling 3,383 square feet. Each unit is individually metered and currently leased, offering a stable and

  Team Kaufelt Truman & Co. (KW)

  905 Grinnell St, Key West, FL 33040
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  /82

  $5,395,000

  • 5 Beds
  • 6 Baths
  • 3,597 Sq Ft

  18 Hilton Haven Rd, Key West, FL 33040

  Double waterfront MM 2 in Key West. Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront

  The Behmke Group Keller Williams Key West Compass Realty

  18 Hilton Haven Rd, Key West, FL 33040
• 

  

  /59

  $1,569,999 New Construction

  • 4 Beds
  • 3 Baths
  • 2,136 Sq Ft

  142 Peg Leg Ln, Cudjoe Key, FL 33042

  Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies -- ideal for soaking in the sunrise or entertaining guests in true Keys

  Alejandro Perez Amerifirst Realty

  142 Peg Leg Ln, Cudjoe Key, FL 33042
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  /25

  $2,789,000

  • 3 Beds
  • 3 Baths
  • 2,212 Sq Ft

  3206 Riviera Dr, Key West, FL 33040

  Welcome to 3206 Riviera Drive, Key West - a stunning canal-front retreat designed for the ultimate Key West lifestyle. This fully gated residence offers 60 feet of waterfront with no neighbors across, creating unmatched privacy and serene water views.Inside, a bright open floor plan with a wall of glass impact sliders connects indoor living to the outdoors. The spacious kitchen features a large

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  3206 Riviera Dr, Key West, FL 33040
• 

  

  /20

  $1,475,000

  • 1 Bed
  • 1 Bath
  • 405 Sq Ft

  422 Amelia St Unit 6, Key West, FL 33040

  Don't miss this TRANSIENT licensed condo just steps away from the famous Duval Street. This second floor 1 bedroom 1 bath unit with 14ft high ceilings is being offered turnkey. Currently operating as a very successful short term vacation rental business. Experience all that Key West has to offer nearby with restaurants, shops, art galleries, beaches and more all in walking or biking distance!

  Tonya Cabanas Truman & Co. (KW)

  422 Amelia St Unit 6, Key West, FL 33040
• 

  

  /22

  $599,000

  • 2 Beds
  • 1 Bath
  • 691 Sq Ft

  2521 Flagler Ave Unit 4, Key West, FL 33040

  This is your chance to own a piece of paradise in the middle of Key West. This two bedroom home is located in a prime midtown location and has been completely renovated with all the modern amenities you could want. The vinyl plank flooring, recessed lighting, and lighted crown moldings create a sleek and stylish look, while the stone countertops, wood cabinetry, and stainless steel appliances

  Jimmy Lane Island Life Realty Experts

  2521 Flagler Ave Unit 4, Key West, FL 33040
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  /8

  $120,000

  • Land

  Lot 6 Vacant Land, Big Pine Key, FL 33043

  Positioned just off US-1 (Jimmy Buffett Memorial Highway), this parcel of land benefits from excellent visibility and accessibility, supporting a wide variety of potential commercial uses.Potential for securing valuable ROGO points for future permitting needs in Monroe County (buyer to verify the number of ROGO points with the County).

  Austin Kimbler Expert Realty LLC (HQ)

  Lot 6 Vacant Land, Big Pine Key, FL 33043
• 

  

  /53

  $2,925,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 4 Baths
  • 3,656 Sq Ft

  1610 von Phister St, Key West, FL 33040

  Fully renovated and redefined mid-century home, perfectly tailored for modern island living. Located on one of the most desirable streets in Key West, this turnkey property sits on an oversized 9,500 square foot lot in the heart of the island. Offering over 3,600 square feet of thoughtfully designed living space, the home features four bedrooms, four full bathrooms and a bonus room ideal for

  Jenna Stauffer Ocean Sotheby's International Realty

  1610 von Phister St, Key West, FL 33040
• 

  

  /20

  $4,920,000

  • 24 Beds
  • 12 Baths
  • 9,000 Sq Ft

  1819 Atlantic Blvd, Key West, FL 33040

  PRIME OPPORTUNITY! 1819 Atlantic Blvd, 1719/21 Josephine St, 1723/25 Josephine St, 1821 Atlantic Blvd & 1823 Atlantic Blvd. EMPLOYEE HOUSING, DEVELOPERS, CONDO CONVERSION! 3 FOURPLEXES 12 units offering 9,000 sq ft of Floor Living Area, and 2 vacant lots for a total of 23,340 sq ft of land. All 12 units are each a 2/1, for a total of 24 bedrooms and 12 baths. Buyer to verify with the governing

  Jeffrey Dunaway Key West Realty, LLC (KW)

  1819 Atlantic Blvd, Key West, FL 33040
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  /2

  $375,000

  • Land
  • 2.39 Acres
  • $156,904 per Acre

  6810 Front St Unit 22, Stock Island, FL 33040

  Great Opportunity and location. 25X60 deep water slip.

  Marc Ulanowski Equestrian Sotheby's International Realty Inc.

  6810 Front St Unit 22, Stock Island, FL 33040
• 

  

  /5

  $1,095,000

  • Land

  416 Applerouth Ln, Key West, FL 33040

  Prime Vacant Lot in Historic Old Town Key West - Rare Opportunity! Located in a vibrant community with rich history, this vacant lot offers endless possibilities for development.

  Jenny Perry Preferred Properties (KW)

  416 Applerouth Ln, Key West, FL 33040
• 

  

  /46

  $735,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  30920 Baileys Ln, Big Pine Key, FL 33043

  Discover the perfect blend of coastal living and convenience in this CBS-built home offering exceptional access to open water--just minutes to both the Gulf and the Atlantic. Situated on a spacious double lot, the property includes a 30 ft. Step down boat slip cut in, ideal for docking your boat and enjoying effortless days on the water.Designed for seamless indoor-outdoor living, the home

  Deni Heintzelman KeyIsle Realty

  30920 Baileys Ln, Big Pine Key, FL 33043
• 

  

  /15

  $4,580,000

  • 10 Beds
  • 9 Baths
  • 7,193 Sq Ft

  1005 Flagler Ave, Key West, FL 33040

  INVESTORS, DEVELOPERS, CONDO CONVERSION--1005 FLAGLER AVE AND 1009 FLAGLER AVE--Two fourplexes in the highly desirable Casa Marina neighborhood on 18,371 sq ft of land, with 7,193 sq ft of Floor Living Area, for a total of 10 bedrooms and 9 baths. 1005 Flagler is 4 units, 3 of which are 1/1, ground floor unit #1 is a 3/2 with a courtyard. There's an on site coin laundry, as well as a garage and

  Jeffrey Dunaway Key West Realty, LLC (KW)

  1005 Flagler Ave, Key West, FL 33040
• 

  

  /80

  $7,495,000

  • 5 Beds
  • 7 Baths
  • 4,000 Sq Ft

  616 Eaton St, Key West, FL 33040

  Nestled in the heart of Key West's historic district, 616 Eaton Street is a testament to quality, timeless beauty, and refined living. This single-family residence was constructed in 1911 and painstakingly renovated and reimagined over the last few years culminating in 2024 with the spectacular like new home. Most hidden from the Street, it exudes classic Key West architecture blended with modern

  Terri Spottswood Truman & Co. (KW)

  616 Eaton St, Key West, FL 33040
• 

  

  /35

  $580,000

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft

  3210 Eagle Ave, Key West, FL 33040

  Back on the market at no fault to the Sellers! Welcome to Key West Estates, a charming family community ideally situated just a short bike ride from the beautiful beaches, vibrant Duval Street, delightful restaurants, the theater, and shopping centers. This peaceful neighborhood features light one-way traffic and no HOA fees, making it a perfect place to call home.Step inside to discover an

  Bobby Baker Brightwild Real Estate

  3210 Eagle Ave, Key West, FL 33040
• 

  

  /24

  $1,950,000

  • 3 Beds
  • 3 Baths
  • 1,672 Sq Ft

  1310 Atlantic Dr, Key West, FL 33040

  ''A turnkey retreat designed for comfort, connection, and carefree living just minutes from the beach.''Discover serenity in this elevated 3-bedroom, 3-bath Key West retreat, built in 2013, including modern impact doors and windows. The thoughtful two-story design features a convenient first-floor bedroom and two upstairs en suite bedrooms, each opening to private balconies for morning coffee or

  Elizabeth Chamberlain Truman & Co. (KW)

  1310 Atlantic Dr, Key West, FL 33040
• 

  

  /30

  $362,000

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft

  27960 Porgie Path, Little Torch Key, FL 33042

  Canal Front Coral Shores Estates! This 3 Bedroom home with Open Water views of South Pine Channel has a wonderful Swimming Canal ,perfect for kayaking, SUP, and can be easily accessed from the beautiful large new deck- with ladder access to the water. The front of the yard has new fencing, and room to park several cars off street. The inside has 3 bedrooms and a bath, and 2 living room areas.

  Elaine Coyle Keller Williams Key West Compass Realty

  27960 Porgie Path, Little Torch Key, FL 33042
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  /7

  $4,325,000 New Construction

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

  231 E Shore Dr Unit 7, 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 7, Summerland Key, FL 33042
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  /43

  $1,125,000

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

  22837 Calico Jack Cir, Summerland Key, FL 33042

  Seller says Bring Offers....Open Water Views & Sunset Skies with great boating access describes this Concrete Block Construction Home with pre-stress concrete beams holding up a poured concrete floor. Home features open floor plan with vaulted ceilings, tile floors throughout, partial walk-around, storm shutters, 2018 A/C, impact front door and metal roof. Storage room below and ample parking

  Beata Sharpe Coldwell Banker Vanguard Realty

  22837 Calico Jack Cir, Summerland Key, FL 33042
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  /47

  $2,290,000

  • 5 Beds
  • 4 Baths
  • 2,366 Sq Ft

  1519 Johnson St, Key West, FL 33040

  Discover the perfect blend of modern elegance and island charm in this updated 5-bedroom, 4-bathroom Key West retreat. Just blocks from the beach and moments from the vibrant energy of Duval Street, this fully furnished home is ideal for full-time residency or a high-performing investment property.Step inside to an inviting open floor plan featuring gorgeous gray-blue tile flooring and a stylish

  Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  1519 Johnson St, Key West, FL 33040
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  /38

  $4,325,000 New Construction

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

  231 E Shore Dr Unit 7, 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 7, Key West, FL 33040
• 

  

  /54

  $2,585,000

  • 4 Beds
  • 3 Baths
  • 1,957 Sq Ft

  13 Arbutus Dr, Key West, FL 33040

  Welcome to 13 Arbutus Drive, an exceptional waterfront residence located in the coveted Key Haven community--just minutes from vibrant Key West, yet worlds away in peace and privacy. This beautifully maintained home offers the ideal blend of indoor-outdoor living with expansive canal views, deepwater boating access, and luxury finishes throughout, with all impact windows and doors.Bathed in

  Bobby Coe RE/MAX Keys Connection (KW)

  13 Arbutus Dr, Key West, FL 33040
• 

  

  /19

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,032 Sq Ft

  2 Riviera Dr, Key West, FL 33040

  Coastal Paradise: Adorable Mobile Home in the Florida Keys. Discover your piece of paradise in the Florida Keys with this charming single-wide mobile home featuring a spacious addition. Nestled in a quiet, friendly neighborhood, this property offers the perfect blend of comfort and Keys living. This home provides a generous, low-maintenance lot with abundant parking space--perfect for your

  Clarence Clark Key West Luxury Real Estate Inc (KW)

  2 Riviera Dr, Key West, FL 33040
• 

  

  /41

  $795,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  251 Pelican Ln, Big Pine Key, FL 33043

  Tropical Retreat on Two Lots. Discover your slice of paradise with this lovely updated concrete block home, perfectly positioned on an oversized property with serene canal frontage. Move-in ready, meticulously maintained, this home offers both comfort and functionality. Inside, you'll love the cheerful white kitchen with granite counters and backsplash, flowing seamlessly into the open living and

  Sunnie San Lorenzo KeyIsle Realty

  251 Pelican Ln, Big Pine Key, FL 33043
• 

  /2

  $52,000

  • Land

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042

  ROGO lot worth 2 points for DEDICATION purposes. Seller has county ROGO Letter of Land Dedication verifying lot is eligible for land dedication/2 points. Want to build quicker? This is a path. Buyer to verify points and process with Monroe County. See Documents tab for letter.

  Donna Pezzi Keller Williams Key West Compass Realty

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042
• 

  

  /7

  $195,000

  • Land
  • 1.02 Acres
  • $191,177 per Acre

  0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042

  Build your dream home. Imagine waking up to the natural beauty of the Florida Keys on this 44,431sqft lot. It is a special lot that features mature trees. Near Sugarloaf School. 25 minutes to Key West.

  Elizabeth Greco-DeGrenier Florida Keys Realty, Inc.

  0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042
• 

  

  /21

  $1,100,000

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

  817 Terry Ln, Key West, FL 33040

  Step into a piece of Old Town Key West history.Built in 1928, this storybook Old Town cottage captures everything to love about Key West including its timeless character and that easy island rhythm you can feel the moment you arrive.Light, bright, and beautifully furnished, it's move-in ready, the perfect turn-key retreat for anyone dreaming of a second home or an easy vacation rental in the

  Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

  817 Terry Ln, Key West, FL 33040

Showing Results 161 - 200, Page 5 of 18