Homes for Sale near Horace O'Bryant School

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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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  /60

  $2,399,000

  • 6 Beds
  • 5 Baths
  • 2,570 Sq Ft

  1609 United St, Key West, FL 33040

  This mid-town multi-family home offers a remarkable living experience. Designed for comfort and privacy, it features 2 distinct apartments, each w/its own charm & functionality & it can become a 30 day vacation rental w/appropriate licensing. Downstairs: 2 spacious bedrooms & 2 well-appointed bathrooms. The Master has a walk-in closet system, a built-in office; the large Master bath a spacious

  Andrea Weitz Island Life Realty Experts

  1609 United St, Key West, FL 33040
• 

  

  

  /42

  $2,750,000

  • 3 Beds
  • 3 Baths
  • 2,038 Sq Ft

  1500 Atlantic Blvd Unit 414, Key West, FL 33040

  Life is BETTER at the Beach!Enjoy penthouse style living with panoramic ocean views from this two story oceanfront condo!This waterfront setting is magical and simply serene, peaceful and beautiful! Floor to ceiling windows invite natural light, revealing the breathtaking water views from inside as well as the outdoor ocean facing deck - perfect for entertaining, lounging and absorbing sunrises.

  The Behmke Group Keller Williams Key West Compass Realty

  1500 Atlantic Blvd Unit 414, Key West, FL 33040
• 

  

  /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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  /28

  $1,999,999

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

  1438 Virginia St, Key West, FL 33040

  Renovated, highest quality. New heated pool, ipe deck, new metal shingle roof, entire two bedroom is brand new. 6,254 square feet of land, corner lot, park your RV, add guest house, etc. Two on site parking spaces. Home was renovated to convert to single family, currently set up as two units, one two bedroom, two bath with large sleeping loft and a one bedroom, one bath, (two legal units). Both

  Yvette Talbott Appraisers of the Keys Inc (KW)

  1438 Virginia St, Key West, FL 33040
• 

  

  /32

  $1,450,000

  • 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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  /37

  $1,299,000

  • 2 Beds
  • 2 Baths
  • 1,099 Sq Ft

  1901 S Roosevelt Blvd Unit 202W, Key West, FL 33040

  This rare transiently licensed condo is designed to embrace tropical luxury exuding natural light, open concept, practicality and privacy thus creating a serene and inviting environment for you and your guests. Located at La Brisa, a gated condo community, just steps from the beach ,the updated and stylish unit lovingly named ''Moondance'' is the unforgettable retreat you have been dreaming of.

  Robert Donahue Key West Luxury Real Estate Inc (KW)

  1901 S Roosevelt Blvd Unit 202W, Key West, FL 33040
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  /21

  $950,000

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft

  2601 S 2601 Roosevelt Blvd Unit 304C, Key West, FL 33040

  This 3-bedroom 2-bathroom condo is located on the 3rd floor in the gated community Key West by the Sea and is ready for you to move in. This spacious condo offers amazing views of the green lush yard and pool. Perfect place to relax and enjoy Key West. The common area features 2 swimming pools, barbecue area and 2 tennis courts, not to mention you are just steps from Smathers Beach.

  Andrea Otava Last Key Realty, Inc (KW)

  2601 S 2601 Roosevelt Blvd Unit 304C, Key West, FL 33040
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  /54

  $2,950,000

  • 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
• 

  

  /17

  $975,000

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  2601 S Roosevelt Blvd Unit 305, Key West, FL 33040

  Desirable Oceanfront, third floor corner end unit, with panoramic ocean views located in the beautiful, gated condominium complex, Key West By The Sea. Enjoy the ocean views and warm tropical breezes while sitting on your private balcony. The living room/dining area is an open floor plan with direct ocean view. The unit has two large bedrooms, the main bedroom has windows with ocean views

  Daniel Hampson Sutter & Nugent, Inc.

  2601 S Roosevelt Blvd Unit 305, Key West, FL 33040
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  /28

  $1,650,000

  • 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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  /9

  $4,632,100

  • 9 Beds
  • 11 Baths
  • 8,004 Sq Ft

  1812 Flagler Ave, Key West, FL 33040

  Motivated seller!10 Unit Apartment building with ground floor commercial. 9 one bedrooms with one studio apartment. The ground floor is currently being used as a laundromat, that has an office and two large storage areas.. 24 parking spaces are on this property.

  Bobby Coe RE/MAX Keys Connection (KW)

  1812 Flagler Ave, 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

  $1,699,000

  • 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 Dade County pine hardwood flooring and high

  Shad Knapp Beach Club Brokers (KW)

  626 Margaret St, Key West, FL 33040
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  /26

  $525,000

  • 1 Bed
  • 1 Bath
  • 365 Sq Ft

  904 Terry Ln Unit 4, Key West, FL 33040

  Ideal Island Retreat, this adorable, furnished 2nd floor condo has everything you need in order to fully enjoy Old Town KW living. A designated parking spot (golden asset!) on quiet Terry Lane, which is bordered by Whitehead, Thomas, Olivia Sts & Truman Ave, is steps away from famous Duval St, the Hemingway & Lighthouse, as well as iconic restaurants Blue Heaven & Moon Dog Cafe. The Community

  Andrea Weitz Island Life Realty Experts

  904 Terry Ln Unit 4, Key West, FL 33040
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  /72

  $2,294,700

  • 5 Beds
  • 3 Baths
  • 2,560 Sq Ft

  1626 Sirugo Ave, Key West, FL 33040

  This Key West resort-style home sounds like an absolute dream! It combines the perfect blend of luxury, functionality, and tropical charm. With almost 2,800 sq ft of living space, 5 bedrooms, and 3 baths, it's designed for both comfort and elegance. The fact that it's just steps from White Street Pier and the beach makes it an ideal location for those who love coastal living. Some standout

  Derek Epperly Keys Atlantic Realty

  1626 Sirugo Ave, Key West, FL 33040
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  /26

  $750,000

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

  1105 Watson St, Key West, FL 33040

  Located in Key West's Historic District, this two-story, 2-bedroom, 2-bathroom home sits on a manageable lot, offering a unique renovation opportunity. Large primary bedroom, bathroom and sitting area located upstairs. Second bedroom and bathroom on the main floor along with the living, dining and kitchen.Located in the X Flood zone, centrally located on the island, close to downtown and midtown.

  Francesca Santiago Keller Williams Realty Professionals (KW)

  1105 Watson St, Key West, FL 33040
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  /9

  $129,000

  • Land

  1801 N Roosevelt Blvd Unit Marlin 20, Key West, FL 33040

  Custom made 38' houseboat on 1964 Navy Launch. Beautiful water view.1 bedroom, possibly 2, 1 bath. Attached 10' x 10' patio, 2 porches. Slip fee of $ 775 per month includes 2 parking passes, 2 very clean laundry and bath facilities, free pump out, patrolled security. City requires 4% transfer plus 1st/last/security

  Randy Moss Coldwell Banker Schmitt RE Co

  1801 N Roosevelt Blvd Unit Marlin 20, Key West, FL 33040
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  /44

  $2,695,000

  • 4 Beds
  • 6 Baths
  • 3,118 Sq Ft

  1616 Atlantic Blvd Unit 15, Key West, FL 33040

  Welcome to Casa Caselles, where contemporary elegance and coastal serenity harmonize in this spacious breathtaking residence. Located in an exclusive gated enclave of just 19 town homes,this 4 bedroom, plus office, 5.5-bath masterpiece blends modern luxury with timeless charm and boasts an oceanfront pool to elevate your lifestyle.Spanning three levels of artfully designed space, this home

  Elizabeth Chamberlain Truman & Co. (KW)

  1616 Atlantic Blvd Unit 15, Key West, FL 33040
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  /56

  $2,995,000

  • 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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  /98

  $3,650,000 Open Sun 11AM - 1PM

  • 5 Beds
  • 5 Baths
  • 2,721 Sq Ft

  1114 Packer St, Key West, FL 33040

  Luxurious Old Town Key West Oasis with separate Guest House! Nestled in the heart of Key West's historic district, this impeccably remodeled property redefines island elegance. Situated in the coveted X Flood Zone, this home boasts an unparalleled location just steps from iconic Duval Street, world-class dining, vibrant galleries, and pristine beaches. Step inside to discover a light-filled

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  1114 Packer St, Key West, FL 33040
• 

  

  /46

  $2,999,999

  • 2 Beds
  • 4 Baths
  • 1,596 Sq Ft

  405 Petronia St, Key West, FL 33040

  Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2/2 residential, office plus a detached restaurant. Seller financing is available to immediately start your investment opportunity! Call now for your private showing.

  Bobby Coe RE/MAX Keys Connection (KW)

  405 Petronia 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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  /16

  $1,600,000

  • 8 Beds
  • 5 Baths
  • 1,830 Sq Ft

  928 Truman Ave Unit 101, Key West, FL 33040

  Old Town Multi-Use PropertyLocated on Truman Avenue, this distinctive property features five legal long-term rental apartments, making it ideal for steady income or employee housing.Unit 101, a CBS building, offers the potential for commercial conversion (buyer to verify), provided the residential units remain onsite, creating valuable flexibility.Highlights include:8 bedrooms and 5

  Allison Findlay Preferred Properties (KW)

  928 Truman Ave Unit 101, 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

  $1,690,000

  • 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
• 

  

  /44

  $649,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  2601 S Roosevelt Blvd Unit 608, Key West, FL 33040

  Top floor sunset views! Discover this exceptional Oceanview 1-bedroom, 1-bathroom condo that perfectly blends comfort, style, and convenience. From the moment you step inside, you'll be greeted by a spacious living room designed for relaxation and year-round comfort, thanks to mini-split AC units and hurricane-grade soundproof windows and doors. Upgraded through the 2018 Airport Noise Improvement

  Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

  2601 S Roosevelt Blvd Unit 608, Key West, FL 33040
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  /42

  $623,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  2601 S Roosevelt Blvd Unit 319C, Key West, FL 33040

  Elegant and Comfortable Key West Retreat ~Experience the charm and ease of island living in this beautifully renovated condominium at Key West by the Sea. Thoughtfully updated, this residence features quartz countertops, stainless steel Samsung appliances, and an insulated tile floor that enhances both comfort and style. A dedicated wine and beverage chiller adds a touch of luxury to the

  Wendy Moreira Keller Williams Key West Compass Realty

  2601 S Roosevelt Blvd Unit 319C, 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
• 

  

  /9

  $1,701,000

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

  1621 Josephine St, Key West, FL 33040

  Prime 2 duplexes, each a 2/1 up & 2/1 down for a total of 8 bedrooms, 4 baths. Each unit has a generous covered porch extending the living area to the outdoors. Behind and between the 2 buildings is vacant land, room for a pool or outdoor storage, etc. Off-street parking for 4 cars. There's a lovely specimen Buttonwood tree at the entry to the property. A good investment for owner occupancy and

  Jeffrey Dunaway Key West Realty, LLC (KW)

  1621 Josephine St, Key West, FL 33040
• 

  

  /20

  $5,319,000

  • 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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  /10

  $3,491,000

  • 16 Beds
  • 8 Baths
  • 6,000 Sq Ft

  1716 Bertha St, Key West, FL 33040

  EMPLOYEE HOUSING, DEVELOPERS, CONDO CONVERSION! 1714 Bertha St and 1716 Bertha St are two fourplexes with 16 bedrooms and 8 baths, 8 units of 2/1 each, comprising 6,000 sq ft of Floor Living Area on 8,755 sq ft of land, offered with the vacant lot adjacent to 1714 Bertha St, a bonus 5,765 sq ft lot comprising a total of 14,529 sq ft of land. Both buildings have new metal roofs as of 2024.

  Jeffrey Dunaway Key West Realty, LLC (KW)

  1716 Bertha St, Key West, FL 33040
• 

  

  /15

  $5,197,000

  • 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
• 

  

  /47

  $3,999,000

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

  919 Thomas St Unit A,1-3, Key West, FL 33040

  This is the entire four-unit Lighthouse View Condominium Association. It is currently four lucrative long-term rentals. 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 is secluded in the rear with its own private heated pool, hot tub and expansive garden with brick terrace. A free-standing two

  Mabry Binnicker Preferred Properties (KW)

  919 Thomas St Unit A,1-3, Key West, FL 33040
• 

  

  /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
• 

  

  /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
• 

  

  /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 well-maintained gem nestled in lush tropical surroundings in Old Town. 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, shopping, & entertainment, this home combines historic charm with unbeatable

  Madeleine Lowe Expert Realty LLC (HQ)

  1033 Catherine St, Key West, FL 33040

Showing Results 121 - 160, Page 4 of 6