Houses for Sale near Horace O'Bryant School

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  /24

  $4,995,000

  • 4 Beds
  • 3 Baths
  • 2,064 Sq Ft

  924 Flagler Ave, Key West, FL 33040

  924 Flagler, a large corner property is in the heart of the sought after Casa Marina area on sprawling grounds of over 12,300+ square feet. Built for the Edward Strunk family, this iconic estate home has had only two owners. The current owners completely restored and upgraded the property both inside and out, using the finest materials and incredible attention to detail. One of the four bedrooms

  Laura McChesney Preferred Properties (KW)

  924 Flagler Ave, Key West, FL 33040
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  /33

  $1,799,900

  • 3 Beds
  • 4 Baths
  • 1,572 Sq Ft

  908 Catherine St, Key West, FL 33040

  Essentially a Brand-New Home at an Unbeatable Price Per Square Foot!Nestled in the coveted X flood zone, this historic Key West gem has been completely reimagined from the inside out. With all-new plumbing, electrical, roof, and impact-resistant windows, this property offers the charm of the past with the peace of mind of modern construction.Step beyond the charming Caribbean gate and into a

  Jessica Celli Berkshire Hathaway HomeServices Knight & Gardner Realty

  908 Catherine St, Key West, FL 33040
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  /57

  $2,600,000

  • 5 Beds
  • 3 Baths
  • 2,303 Sq Ft

  710 Ashe St Unit Front and Back, Key West, FL 33040

  Welcome to 710 Ashe Street, a masterfully restored 1889 Eyebrow home, where historic charm and contemporary comfort converge in one of Key West's most sought-after locations. This exceptional property, complete with a detached guest house, offers a versatile and elegant living experience--perfect for families, in-laws, or lucrative rental opportunities (rental figures available upon request). The

  Team Kaufelt Truman & Co. (KW)

  710 Ashe St Unit Front and Back, Key West, FL 33040
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  /26

  $1,150,000

  • 2 Beds
  • 1 Bath
  • 1,021 Sq Ft

  710 Ashe St Unit Rear, Key West, FL 33040

  Tucked away on one of the best streets in Old Town Key West, 710 Ashe Street Rear is a beautifully remodeled 2 bedroom, 1 bath residence offering the perfect balance of family living and an optional vacation rental opportunity. Upon entering, an expansive open floor plan invites you in, with the living, dining, and kitchen areas flow effortlessly into one another. Framed by four sets of French

  Team Kaufelt Truman & Co. (KW)

  710 Ashe St Unit Rear, Key West, FL 33040
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  /52

  $2,999,000

  • 3 Beds
  • 4 Baths
  • 1,620 Sq Ft

  608 Grinnell St, Key West, FL 33040

  High style in a highly desirable location. Amidst the quaint lanes and the best restaurants on the island you will find this completely renovated, incredibly designed and decorated 1,620 square foot, three bedroom and three and one-half bathroom delightful Conch home. In arguably the best location in Old Town you are close enough to walk or bike to everywhere you want to go yet tucked away

  Karen Lane Berkshire Hathaway HomeServices Knight & Gardner Realty

  608 Grinnell St, Key West, FL 33040
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  /40

  $3,450,000

  • 5 Beds
  • 6 Baths
  • 3,081 Sq Ft

  1717 Thompson St, Key West, FL 33040

  Extraordinary transformation of this luxurious elevated midtown home boasting 5 spacious bedrooms each with stunning designer ensuite baths. Originally built in 1997 with a full scale ground up renovation completed in 2024, this home boasts the gorgeous custom details at every turn. The elevated main floor of the home features an open floor plan and wet bar that leads seamlessly to a sprawling

  Wendy Zintsmaster Truman & Co. (KW)

  1717 Thompson St, Key West, FL 33040
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  /32

  $1,499,000 Open Fri 4PM - 6PM

  • 2 Beds
  • 2 Baths
  • 877 Sq Ft

  412 Louisa St, Key West, FL 33040

  Welcome to 412 Louisa Street, an enchanting Key West Conch Cottage nestled on a serene one-way street between Duval and Whitehead in Old Town. This charming 2-bedroom, 2-bathroom home offers a pool, parking and proximity to all that Key West has to offer. Built in 1933, the property seamlessly blends historic charm with modern comforts. As you step inside, you'll be greeted by an open-concept

  Bobby Coe RE/MAX Keys Connection (KW)

  412 Louisa St, Key West, FL 33040
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  /50

  $2,495,000

  • 3 Beds
  • 3 Baths
  • 1,391 Sq Ft

  410 Catherine St, Key West, FL 33040

  Dona Calabash - Located just a half a block from the upper end of Duval Street this charming Old Town beauty has it all! Three bedrooms including a luxurious master suite with spa bath, two guest bedrooms and two full baths. The gourmet kitchen features commercial grade stainless appliances, granite countertops and plenty of storage. Rear French doors open to a covered deck and the refreshing

  The Behmke Group Keller Williams Key West Compass Realty

  410 Catherine St, Key West, FL 33040
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  /54

  $2,950,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 2,397 Sq Ft

  827 Eisenhower Dr, Key West, FL 33040

  This is one of the very few waterfront homes in Old Town Key West that comes with a private boat slip and open water views. The house features a large living room and kitchen area and a gorgeous sunroom with floor to ceiling windows overlooking the water and leading out to a spacious deck. A private path from the deck gives access to a heated pool that is part of the HOA fees that also include

  Ralph Sanchez Century 21 All Keys Inc (KW)

  827 Eisenhower Dr, Key West, FL 33040
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  /28

  $1,699,000

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  819 Elizabeth St, Key West, FL 33040

  Welcome to Casa Bella Petite le Bleu., an architectural gem in the heart of Old Town Key West, honored with a prestigious Ceramic Star for historic preservation. Nestled in the desirable X-Flood Zone, this home blends timeless charm with contemporary upgrades, off street parking and a private pool making it the perfect tropical retreat. From the moment you arrive, the classic front porch invites

  Paige Bethel Island Home Realty Inc.

  819 Elizabeth St, Key West, FL 33040
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  /20

  $799,000

  • 3 Beds
  • 1 Bath
  • 1,154 Sq Ft

  1704 Duncan St, Key West, FL 33040

  Introducing 1704 Duncan Street, a delightful 3-bedroom, 1-bathroom home located in the desirable Newtown Key West neighborhood. This property features a generously sized backyard, ideal for outdoor enjoyment, along with a separate storage and laundry room for added convenience. The home is currently tenant-occupied; kindly allow 24 hours' notice for showings.

  Justyn Ewald Expert Realty LLC (HQ)

  1704 Duncan St, Key West, FL 33040
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  /45

  $1,799,000

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

  626 Margaret St, Key West, FL 33040

  Welcome to this captivating historic Conch home, where the essence of Key West island luxury comes alive. This charming residence boasts a classic front porch that beckons you to sit back and enjoy the tropical breeze, making it an ideal space for leisurely mornings or cozy evenings. Upon entering, you are greeted by a sun-drenched interior adorned with exotic hardwood flooring and soaring high

  Shad Knapp Beach Club Brokers (KW)

  626 Margaret St, Key West, FL 33040
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  /26

  $925,000

  • 2 Beds
  • 2 Baths
  • 1,592 Sq Ft

  1105 Watson St, Key West, FL 33040

  Nestled in Key West's Historic District, this two-story, 2-bedroom, 2-bathroom home sits on a small, manageable lot, offering a unique renovation opportunity. The property's classic architecture and historical charm are just waiting to be restored and personalized to your taste. With a bit of vision, this space can become the perfect island retreat or vacation rental.Though the lot is compact,

  Francesca Santiago Chavez Keller Williams Realty Professionals (KW)

  1105 Watson St, Key West, FL 33040
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  /58

  $3,150,000

  • 3 Beds
  • 3 Baths
  • 1,615 Sq Ft

  1511 Johnson St, Key West, FL 33040

  Discover your dream Transient Vacation Rental in the heart of mid-town Key West! This beautifully refreshed home boasts a light and airy atmosphere and is sold fully furnished with rentals on the books and ready to go. Featuring three bedroooms, including a spacious primary suite and three baths, this property offers an inviting open living and kitchen area, highlighted by soft hues and vibrant

  Shad Knapp Beach Club Brokers (KW)

  1511 Johnson St, Key West, FL 33040
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  /46

  $3,600,000

  • 3 Beds
  • 4 Baths
  • 1,890 Sq Ft

  715 Frances St, Key West, FL 33040

  Impeccably preserved historic residence located in the heart of Old Town Key West. Discover the enticing charm of Key West and stroll through the majestic tree lined streets from 715 Frances Street. A rare combination of Key West luxury and historic architecture, this beautiful eyebrow home is perfectly positioned on a large spacious lot on sought after X Flood zone keeping you high and

  Suzanne Moore Suzanne Moore Real Estate

  715 Frances St, Key West, FL 33040
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  /47

  $3,999,000

  • 7 Beds
  • 7 Baths
  • 3,015 Sq Ft

  919 Thomas St Unit 1A, Key West, FL 33040

  This property has a glamourous three bedroom, three and a half bath owners' unit with private pool and hot tub, plus three lucrative long-term rentals. It is the entire Lighthouse View Condominium Association, currently inactive. Enter thru the electric gate to a bricked courtyard with parking for several cars and many bicycles and access to a covered carport. The main residence with its heated

  Mabry Binnicker Preferred Properties (KW)

  919 Thomas St Unit 1A, Key West, FL 33040
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  /37

  $1,790,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  613 Olivia St, Key West, FL 33040

  Welcome to 613 Olivia Street, a charming single-family home nestled in the heart of Old Town, Key West. Built in 1933, and located in the X Flood Zone, this historic residence offers 1,680 square feet of living space on two floors and on a 3,240 square foot lot. This property has been owner occupied for over 30 years. First time on the market in generations. Here is your chance to have that

  Bobby Coe RE/MAX Keys Connection (KW)

  613 Olivia St, Key West, FL 33040
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  /41

  $1,750,000

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

  205 Virginia St, Key West, FL 33040

  Welcome to 205 Virginia Street, a meticulously crafted single-family home nestled in the heart of Old Town Key West. Built in 2019, this residence seamlessly blends the historic charm of the area with modern construction standards. As you step inside, you'll be greeted by an open and inviting living space adorned with wood floors and bathed in natural light. The gourmet kitchen boasts quartz

  Jimmy Lane Island Life Realty Experts

  205 Virginia St, Key West, FL 33040
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  /32

  $1,680,000

  • 3 Beds
  • 2 Baths
  • 1,463 Sq Ft

  1211 Catherine St, Key West, FL 33040

  This charming historic home is located just steps off vibrant White St and close to the beach, tennis courts, pickle ball and a short walk to famous Duval St. It's close to the action but in a tranquil area of the White St District.This property has many great features such as 10ft high ceilings through out the entire home, abundance of large windows, open floor plan with spacious living area,

  Haydee Stewart Bascom Grooms Real Estate (KW)

  1211 Catherine St, Key West, FL 33040
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  /64

  $4,250,000

  • 5 Beds
  • 7 Baths
  • 2,681 Sq Ft

  1311 Grinnell St, Key West, FL 33040

  This stunning home in Casa Marina is a complete restoration of the original historic structure. Just 5 blocks from Higgs Beach and 6 blocks from Duval Street this property has a large master bedroom and two guest bedrooms on the main floor all with private baths and their own entrances opening to over 900 square feet of wraparound porches. The wide entrance hallway has an additional 1/2 bath and

  Jennifer Newman Truman & Co. (KW)

  1311 Grinnell St, Key West, FL 33040
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  /40

  $1,749,000

  • 3 Beds
  • 3 Baths
  • 1,897 Sq Ft

  1033 Catherine St, Key West, FL 33040

  Step into Key West history with a modern twist at the Kali Zoi House, a meticulously maintained gem nestled in lush tropical surroundings in Old Town Key West. Originally built in the early 1900s & updated in 1988, this fully furnished home offers nearly 1,900sqft of spacious living. Located near everything (Duval Street, beaches, etc.), this home combines historic charm with unbeatable

  Madeleine Lowe Expert Realty LLC (HQ)

  1033 Catherine St, Key West, FL 33040
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  /22

  $2,895,000

  • 4 Beds
  • 3 Baths
  • 2,880 Sq Ft

  1100 South St, Key West, FL 33040

  Located in the highly regarded Casa Marina neighborhood, this exceptional property offers a unique opportunity to own a piece of Key West history. Ernest Hemingway the iconic literary figure once called this house his Winter retreat during 1928 -1929, where he penned the timeless classic, 'A FAREWELL TO ARMS.'' This sprawling single story property spans an impressive 8100 square feet, occupying a

  Key West Luxury Finders Preferred Properties (KW)

  1100 South St, Key West, FL 33040
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  /21

  $4,999,000

  • 5 Beds
  • 6 Baths
  • 3,434 Sq Ft

  515 Amelia St, Key West, FL 33040

  Discover the charm of Casa Grande, a stunning TRANSIENT residence with a strong rental history. Nestled on a tranquil dead-end street, just one block from the vibrant Duval Street in Key West, this exceptional home offers off-street parking for two vehicles.Designed for entertaining, Casa Grande features an expansive open floor plan that seamlessly connects the spacious living room to the

  Jenny Perry Preferred Properties (KW)

  515 Amelia St, Key West, FL 33040
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  /30

  $998,000

  • 2 Beds
  • 2 Baths
  • 1,700 Sq Ft

  608 Roberts Ln, Key West, FL 33040

  OLD TOWN CONCH HOUSE on a lovely Lane tucked away but close to all of your favorite shops, cafes and Key West attractions! First time on the market in over 45 years! This historic home built by the Roberts Family is located on a quiet cul-de-sac lane in Old Town Key West. Tucked away and just off Frances St, 608 Roberts Lane (formerly known as Cates Lane as well as Darwin Court dates back to the

  Bascom Grooms Bascom Grooms Real Estate (KW)

  608 Roberts Ln, Key West, FL 33040
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  /24

  $1,270,000

  • 2 Beds
  • 3 Baths
  • 976 Sq Ft

  1123 Petronia St, Key West, FL 33040

  Take advantage of this $24,000 price improvement!Located in the heart of Old Town, this modern redesigned historic home is filled with light and love as a welcomed new addition to the Key West real estate market. On an intimate less traveled street, an inviting front porch brings you into a truly wonderful haven that is entirely move in ready with no loose ends or repairs needed. Distressed pine

  Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

  1123 Petronia St, Key West, FL 33040
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  /30

  $1,668,000

  • 3 Beds
  • 2 Baths
  • 1,051 Sq Ft

  1202 Whitehead St, Key West, FL 33040

  This beautifully restored old Key West home offers the perfect tropical escape. Located just a block from Duval Street, Garden of Roses combines historic charm with modern upgrades, making it an ideal vacation home. Currently being rented as a monthly vacation rental!Enjoy a spacious layout with 3 bedrooms, a high-end kitchen, and bright, open living areas. Relax outdoors with a private hot tub,

  Richard Haskins Buy The Keys

  1202 Whitehead St, Key West, FL 33040
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  /63

  $3,100,000

  • 5 Beds
  • 4 Baths
  • 2,711 Sq Ft

  1419 Thompson St, Key West, FL 33040

  Stately Key West home has undergone a stunning renovation but maintains classic Keys charm with a beautiful wood staircase, stained glass window and transom, Dade County pine walls, and wraparound porches on both levels. Centrally located in Key West this home is the perfect island residence with POOL! The main level offers plenty of room for entertaining with large spaces for conversation,

  Bascom Grooms Bascom Grooms Real Estate (KW)

  1419 Thompson St, Key West, FL 33040
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  /51

  $4,295,000

  • 5 Beds
  • 3 Baths
  • 3,300 Sq Ft

  1319 Olivia St, Key West, FL 33040

  Built in 1943, and Originally owned within the Singleton Estate, 1319 Olivia St. is more than just a home, it's a legacy, embodying beauty, elegance and history at every turn.Ideally located within the heart of the meadows, this Historic Grand Dame is one of the most impressive homes in Key West today, known for it's stunning architecture and superb craftsmanship.Both kitchen and living rooms

  Suzanne Moore Suzanne Moore Real Estate

  1319 Olivia St, Key West, FL 33040
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  /39

  $2,599,000

  • 5 Beds
  • 4 Baths
  • 2,703 Sq Ft

  1701 Atlantic Blvd, Key West, FL 33040

  A stunning new renovation transforms this spacious elevated home to a total of 5bd/4ba plus a bonus space and is offered fully furnished with brand new coastal decor. Situated on a spacious corner parcel this home also offers multiple covered patios, maintenance free green space, a large heated pool and covered parking. An open concept floor plan welcomes you to a stunning great room, spacious

  Wendy Zintsmaster Truman & Co. (KW)

  1701 Atlantic Blvd, Key West, FL 33040
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  /24

  $3,650,000

  • 3 Beds
  • 3 Baths
  • 1,524 Sq Ft

  628 William St, Key West, FL 33040

  ** BREATHTAKING RENOVATION** Nestled in the heart of Old Town, this century-old gem has been lovingly renovated and is waiting for you to call it home. This historic residence perfectly balances convenience and tranquility, offering a true slice of paradise just waiting for you.Every inch of this home has been thoughtfully updated and perfected--from the floors to the air ducts to the attic. The

  Patrick DeKeyrel Last Key Realty, Inc (KW)

  628 William St, Key West, FL 33040
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  /47

  $2,950,000

  • 4 Beds
  • 4 Baths
  • 2,028 Sq Ft

  831 Georgia St, Key West, FL 33040

  Beautiful Meadows Masterpiece located one of Key West's idyllic neighborhoods. Built in 2020 using the finest materials and craftsmanship, this home combines the best of Key West Architecture with modern luxury finishes.Exquisite Nickel-grooved walls and stunning hardwood floors that create a warm and inviting atmosphere. The coffered ceilings, adorned with Dade County Pine add that extra touch

  Suzanne Moore Suzanne Moore Real Estate

  831 Georgia St, Key West, FL 33040
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  /31

  $2,850,000

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

  410 Louisa St, Key West, FL 33040

  Experience the epitome of luxury in this exquisite 3BD/3BA residence nestled on a quiet Lane in the heart of Old Town Key West, just a stone's throw from the world famous Southernmost Point and 1 block from the iconic Duval Street. Indulge in the unparalleled convenience of having Key West's renowned restaurants, museums, and art galleries at your doorstep, with the beach a leisurely bike ride

  Team Spottswood/Vazquez Truman & Co. (KW)

  410 Louisa St, Key West, FL 33040
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  /34

  $3,799,000

  • 5 Beds
  • 4 Baths
  • 2,960 Sq Ft

  1214 White St, Key West, FL 33040

  Introducing ''Blu on White'' one of Key West's most stunning historic single level residences in desirable Old Town Key West. Exceptional location scoring a full 10 on the walkability scale with easy access to the beaches, White St. Pier, an array of galleries, restaurants and cafes.Taking full advantage of the generous 5800 sq ft. lot, this 5BD/4BA home offers so much space and versatility with

  Suzanne Moore Suzanne Moore Real Estate

  1214 White St, Key West, FL 33040
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  /43

  $1,450,000

  • 3 Beds
  • 4 Baths
  • 1,932 Sq Ft

  1409 Truman Ave, Key West, FL 33040

  Welcome to 1409 Truman Avenue, a stunning Key West Eyebrow home that combines historical charm with modern amenities. Key Features, Historical Architecture, Enjoy high ceilings, beautiful Dade County Pine throughout, an open staircase, all signature elements of this classic Key West home. Spacious Layout, The home boasts 3 bedrooms one being a large master bedroom with a walk in closet, each with

  Michael Sorah Truman & Co. (KW)

  1409 Truman Ave, Key West, FL 33040
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  /26

  $2,849,000

  • 3 Beds
  • 3 Baths
  • 2,361 Sq Ft

  1011 South St, Key West, FL 33040

  Gorgeous tropical gardens greet you to this enchanting home in the coveted Casa Marina neighborhood. Enjoy a spacious 3 beds/ 2.5 baths with pool and off-street parking. While the home is complete with all the amenities one would expect in an island home the improvements are intentionally simple yet thoughtful to preserve its vintage charm. Through the front door you will be welcomed to a

  Wendy Zintsmaster Truman & Co. (KW)

  1011 South St, Key West, FL 33040
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  /36

  $2,449,000

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  2 Aronovitz Ln, Key West, FL 33040

  Tucked away on a hidden lane just a half of block off of Duval Street, 1 and 2 Aronovitz Lane is a true diamond in the rough! A one of a kind opportunity that is being offered for the first time ever. This listing consists of two platted lots with a total of three development rights and 5,614 sq. ft. of land. The existing well maintained house at 2 Aronovitz Lane is a two bedroom/one bathroom

  Terry Garcia Keller Williams Key West Compass Realty

  2 Aronovitz Ln, Key West, FL 33040
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  /4

  $1,349,000

  • 3 Beds
  • 3 Baths
  • 1,520 Sq Ft

  818 Elizabeth St Unit Front, Key West, FL 33040

  Unique opportunity to renovate this historic Old Town eyebrow home on a quiet, one-way, block of Elizabeth Street. Situated on a 2623 Sq.ft. lot there is ample space for off-street parking, a pool and 5 bedrooms with a renovation. Seller financing possible. Please note that advanced notice is required to arrange showings.

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  818 Elizabeth St Unit Front, Key West, FL 33040
• 

  

  /17

  $870,000

  • 6 Beds
  • 4 Baths
  • 2,050 Sq Ft

  1304 Elizabeth St, Key West, FL 33040

  SELLER FINANCING NOW AVAILABLE!Attention developers and investors:Located just 2 blocks from the beach on a quiet one-way street, 1304 Elizabeth Street presents a rare opportunity for those looking to build in Key West's beloved Casa Marina District. This is currently a legal three-unit property in the X flood zone. Additionally, the neighboring property is also available for

  Lori Langton Berkshire Hathaway HomeServices Knight & Gardner Realty

  1304 Elizabeth St, Key West, FL 33040
• 

  

  /22

  $799,999

  • 2 Beds
  • 1 Bath
  • 1,057 Sq Ft

  1102 Whitehead St, Key West, FL 33040

  Location, Location, Location! A renovation project that will increase the value of your investment exponentially! This home is located between the Southernmost Point and the Hemingway House in the world-renowned City of Key West Florida. Besides the excellent location, this home has concrete fences, a concrete gated entry from Whitehead Street, a nice sized rear deck/patio, front sitting/garden

  Margarita Villoch Island Group Realty (KW)

  1102 Whitehead St, Key West, FL 33040
• 

  

  /9

  $1,510,000

  • 3 Beds
  • 2 Baths
  • 1,170 Sq Ft

  1909 Seidenberg Ave, Key West, FL 33040

  Welcome to your Rare 10,000+ Square Foot property - Nearly a quarter acre on the Island of Key West! Remodel the current existing home with a bonus detached garage or Build your Florida Island Dream compound. Developers this one is for you too! Excellent ultra private location. A Rare Opportunity, this exquisite property nestled in the prime location of Midtown East, spans over two lots and over

  Gregg Powers Keller Williams Key West Compass Realty

  1909 Seidenberg Ave, Key West, FL 33040

Showing Results 81 - 120, Page 3 of 4