Old Town Homes for Sale

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  /37

  $1,392,100

  • 2 Beds
  • 1 Bath
  • 759 Sq Ft

  1020 Fleming St, Key West, FL 33040

  Welcome to 1020 Fleming Street, an adorable Conch Cottage situated on the corner of prestigious Fleming Street and Nassau Lane. Built in 1918, this two (2) bedroom and one (1) bath charming and historic home is the perfect retreat in Old Town, Key West. Once a famous Old Town Grocery Store.Step inside your white picket fence and into one of two brick-paved courtyards, complete with a fire pit

  Bobby Coe RE/MAX Keys Connection (KW)

  1020 Fleming St, Key West, FL 33040
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  /36

  $1,799,000

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft

  1011 Simonton St Unit 1, Key West, FL 33040

  Excellent opportunity whether looking for a private residence or an investment. This home will not disappoint. Artfully renovated very spacious three story . Plenty of outside area including private courtyard with a heated pool. Walk out the front door and just steps away from Duval st. and everything Key West has to offer. This is maintenance free living while it gives the feeling of a private

  Marc Ulanowski Equestrian Sotheby's International Realty

  1011 Simonton St Unit 1, Key West, FL 33040
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  /21

  $399,000

  • 1 Bed
  • 1 Bath
  • 454 Sq Ft

  1124 Catherine St Unit 201, Key West, FL 33040

  Charming 1-bedroom, 1-bathroom condo offering 454 square feet of living space. The condo boasts an open floor plan with hurricanes rated windows, one assigned parking spot and also located in the X Flood Zone. The monthly condo fee for this unit is $238.96 and includes windstorm and liability insurance. The property is just few a few blocks from vibrant Duval Street, known for entertainment and

  The Spottswood Team Truman & Co. (KW)

  1124 Catherine St Unit 201, Key West, FL 33040
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  /21

  $998,000

  • 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
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  /38

  $5,850,000

  • 6 Beds
  • 8 Baths
  • 3,010 Sq Ft

  421-423 Simonton St, Key West, FL 33040

  Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  421-423 Simonton St, Key West, FL 33040
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  /13

  $1,899,000

  • 7 Beds
  • 6 Baths
  • 2,790 Sq Ft

  909 Grinnell St, Key West, FL 33040

  Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! That's less than $272K per unit! Recent changes to IRS tax code (such as accelerated depreciation) can benefit RE Investors - ask your tax expert. Prime location, just 1/2 block from cemetery and 1/2 block off Truman Ave. Currently configured as 6 units (but City recognizes

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  909 Grinnell St, Key West, FL 33040
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  /11

  $549,000

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  1318 Duncan St Unit 3, Key West, FL 33040

  Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart

  Rob Severin Rob Severin Real Estate Co

  1318 Duncan St Unit 3, Key West, FL 33040
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  /24

  $849,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 1 Bath
  • 1,342 Sq Ft

  1425 Eliza St, Key West, FL 33040

  3 bedroom single-family home offering the opportunity to add a second bathroom within the existing roofline. Relax on the covered front porch and enjoy the Key West lifestyle. The private backyard provides space for a pool or outdoor entertaining. A great chance to renovate and make this home your own. Being sold As-Is.

  Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

  1425 Eliza St, Key West, FL 33040
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  /38

  $1,225,000

  • 2 Beds
  • 3 Baths
  • 1,240 Sq Ft

  1075 Duval St Unit R10, Key West, FL 33040

  Tucked away in the heart of Old-Town Key West!Welcome to 1075 R10 Duval Street offers the perfect blend of privacy, island charm, and effortless living. This thoughtfully designed 2-bedroom, 2.5-bathroom residence features 1,240 square feet of living space and is ideally positioned in a quiet, off-the-street setting while remaining just moments from shopping, dining, beaches, Boating and all that

  Bobby Coe RE/MAX Keys Connection (KW)

  1075 Duval St Unit R10, Key West, FL 33040
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  /47

  $2,538,000

  • 10 Beds
  • 6 Baths
  • 3,876 Sq Ft

  912 Pohalski St, Key West, FL 33040

  Unlock the potential of this exceptional multifamily complex nestled in the heart of Old Town Key West. With a total of six units offering a diverse mix of layouts, including three 1-bedroom/1-bathroom units, two 2-bedroom/1-bathroom units, and one 3-bedroom/1-bathroom unit, this property presents an unparalleled investment opportunity in one of the most coveted destinations in the Florida Keys.

  Richard Haskins Buy The Keys

  912 Pohalski St, Key West, FL 33040
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  /43

  $2,595,000

  • 3 Beds
  • 3 Baths
  • 2,049 Sq Ft

  508 Grinnell St, Key West, FL 33040

  Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

  Marc Ulanowski Equestrian Sotheby's International Realty

  508 Grinnell St, Key West, FL 33040
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  /15

  $1,199,000

  • 3 Beds
  • 1 Bath
  • 943 Sq Ft

  719 Elizabeth St, Key West, FL 33040

  Location, Location, Location! Old Town in X-Flood Zone on Solaris Hill with Off Street Parking! Quintessential conch cottage has a cozy front porch & has been in the same family for decades. All wood structure shows a glimpse of wood boards behind the existing interior paneling. This is believed to be the much-desired Dade County Pine. Roof and main electrical panel replaced (w/ permits) in 2014.

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  719 Elizabeth St, Key West, FL 33040
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  /40

  $2,699,000

  • 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

  The Spottswood Team Truman & Co. (KW)

  410 Louisa St, Key West, FL 33040
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  /27

  $1,249,000

  • 3 Beds
  • 2 Baths
  • 1,395 Sq Ft

  1209 Pearl St, Key West, FL 33040

  Charming historic duplex ideally located within walking distance to the White Street Gallery District, Old Town, and Key West beaches. The ground-floor unit features a 2BD/1BA layout with a separate living room and updated kitchen, off-street parking, and good size yard with room to add a pool. A covered outdoor living area spans the length of the property and is surrounded by tropical

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  1209 Pearl St, Key West, FL 33040
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  /35

  $1,550,000

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft

  1119 Simonton St Unit A1, A2, C1, Key West, FL 33040

  Charming Old Town Duplex located in the heart of old town. Ideally located on Simonton Street this charming duplex places you just steps from Duval Street, along with world-class dining, boutique shopping, beaches, and neighborhood parks.This versatile property is the perfect Key West residence, second home, or income-producing investment. Live in one side and rent the other, or maximize its

  Paige Bethel Island Home Realty Inc.

  1119 Simonton St Unit A1, A2, C1, Key West, FL 33040
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  /61

  $1,950,000 Open Sun 11AM - 1PM

  • 5 Beds
  • 3 Baths
  • 2,146 Sq Ft

  530 White St, Key West, FL 33040

  Wonderful large home with a 7400 square foot yard!. Currently configured as 3 units, this property can be lived in as is or renovated for maximum potential. Located on the corner of White street and Stump lane, this property has beautiful grounds, room for a large pool, a workshop, decking, and off street parking. The First level features 2 units, each one has 2 bedrooms and 1 bath. Each unit is

  Elaine Coyle Keller Williams Key West Compass Realty

  530 White St, Key West, FL 33040
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  /33

  $800,000 Open Sun 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 648 Sq Ft

  906 Truman Ave Unit 2, Key West, FL 33040

  Old Town First floor 2 Bedroom, 2 Bath condo, pool side!. Great Old Town location, close to Restaurants, '' Walk on White' , Grocery store, and a short walk or bicycle ride to Duval street. This wonderful 2 bedroom, 2 bath condo is one of 4 units and is located steps from the shared pool. Unique to this condo is an outside covered area with a Grill, wet-bar, and seating, exclusively for use with

  Elaine Coyle Keller Williams Key West Compass Realty

  906 Truman Ave Unit 2, Key West, FL 33040
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  /60

  $7,490,000

  • 11 Beds
  • 11 Baths
  • 3,034 Sq Ft

  525 Simonton St, Key West, FL 33040

  A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House--one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom

  Paige Bethel Island Home Realty Inc.

  525 Simonton St, Key West, FL 33040
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  /48

  $4,898,000

  • 4 Beds
  • 5 Baths
  • 3,336 Sq Ft

  1006 Fleming St, Key West, FL 33040

  MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully appointed structures. Behind a privacy wall & gate, the estate includes a grand main residence and two guest houses (both with kitchenettes), offering a total of four bedrooms and

  Terri Spottswood Truman & Co. (KW)

  1006 Fleming St, Key West, FL 33040
• 

  

  /22

  $878,000

  • 2 Beds
  • 1 Bath
  • 568 Sq Ft

  1218 Packer St Unit Rear, Key West, FL 33040

  Nestled in an X flood zone in Old Town , this lovely conch cottage has been well cared for, meticulously maintained and lightly used as a seasonal getaway. The two-bedroom, one-bath residence is fully furnished and move-in ready, offering a perfect blend of charm, comfort, and thoughtful design. Behind the private gate, the home immediately feels welcoming and serene, creating a true island

  Robert Donahue Key West Luxury Real Estate Inc (KW)

  1218 Packer St Unit Rear, Key West, FL 33040
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  /30

  $820,000 Open Sun 1PM - 3PM

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft

  817 Eaton St Unit 1, Key West, FL 33040

  Old Town Condo Near Duval:Bright 1-bedroom, 1-bath condo located in the heart of Historic Old Town Key West. Featuring high ceilings and an open floor plan, this residence is filled with natural light. Just steps from Duval Street, dining, shopping, and entertainment. Ideal as a vacation rental, investment property, or personal island retreat.OWNERS MAY HAVE A PET WITH ASSOCIATION APPROVAL.

  Letisia Powell Robert Slack LLC

  817 Eaton St Unit 1, Key West, FL 33040
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  /37

  $4,750,000

  • 4 Beds
  • 5 Baths
  • 2,716 Sq Ft

  709 Eaton St, Key West, FL 33040

  Step into the enchanting world of Key West history at 709 Eaton Street, a meticulously preserved gem built circa 1847 in the iconic Seaport neighborhood. Historic charm and modern comfort, this home delivers 4 bedrooms, 4.5 baths, with 3 bedrooms, 3.5 baths conveniently located on the first level. The upstairs consists of the primary bedroom suite with an additional private study as well as a

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  709 Eaton St, Key West, FL 33040
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  /18

  $750,000

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

  1119 Simonton St Unit A1, Key West, FL 33040

  Ideally located on Simonton Street in the heart of Old Town, this charming half-duplex is just steps from Duval Street and close to dining, shopping, beaches, and neighborhood parks.Perfect as a full-time island residence, second home, or investment property, this home offers the quintessential Key West lifestyle in one of the island's most desirable locations.The property features a welcoming

  Paige Bethel Island Home Realty Inc.

  1119 Simonton St Unit A1, Key West, FL 33040
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  /31

  $1,299,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  414 Virginia St, Key West, FL 33040

  Lovely 3 bedroom 2 bath home in the midst of Old Town just off Duval St. Central AC with nice room sizes and great lot size. Flood Zone Z500. Ready to sell As-Is. Seller motivated but firm on price.

  Bernard Isler Isler Realty & Investments LLC

  414 Virginia St, Key West, FL 33040
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  /59

  $4,990,000

  • 4 Beds
  • 4 Baths
  • 2,441 Sq Ft

  720D Simonton St, Key West, FL 33040

  KEY WEST'S UNLIKELY SANCTUARY | DUAL TRANSIENT LICENSES While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE

  The Spottswood Team Truman & Co. (KW)

  720D Simonton St, Key West, FL 33040
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  /58

  $1,800,000

  • 4 Beds
  • 3 Baths
  • 1,943 Sq Ft

  408 William St, Key West, FL 33040

  Blending timeless character and modern comfort this home is nestled on one of Old Town's most coveted streets. Come discover this captivating home steeped in rich history. The kitchen has been thoughtfully redesigned with granite counters, new stainless-steel appliances & now has an open layout that enhances both function and flow. The Richard Roberts home, originally transported from Green

  Terri Spottswood Truman & Co. (KW)

  408 William St, Key West, FL 33040
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  /36

  $799,000

  • 1 Bed
  • 2 Baths
  • 650 Sq Ft

  616 Caroline St Unit 6, Key West, FL 33040

  Situated along one of Old Town's most storied corridors, residence #6 at 616 Caroline Street offers a refined Keys lifestyle just steps from the Historic Seaport, Duval Street dining, galleries, and marinas. Tucked within a boutique setting, this private upstairs home balances character and comfort with a bright, welcoming living area and an efficient layout that makes everyday living--and easy

  Jimmy Lane Island Life Realty Experts

  616 Caroline St Unit 6, Key West, FL 33040
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  /42

  $4,450,000

  • 4 Beds
  • 5 Baths
  • 2,985 Sq Ft

  1113 Stump Ln, Key West, FL 33040

  Experience the ideal blend of historic charm and modern luxury in this fully renovated and expanded Key West residence, where no detail has been overlooked. Set on a quiet, one-way street in Old Town, this 4-bedroom, 4.5-bath home offers 2,985 square feet of thoughtfully designed living space. Inside, soaring cathedral ceilings and rich Dade County pine walls create a warm, timeless aesthetic.

  Terri Spottswood Truman & Co. (KW)

  1113 Stump Ln, Key West, FL 33040
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  /55

  $3,899,000 Open Sun 12PM - 3PM

  • 4 Beds
  • 3 Baths
  • 2,271 Sq Ft

  813 Thomas St, Key West, FL 33040

  NOW offered fully furnished! Located on a rare double lot in the coveted X flood zone, discover an extraordinary opportunity to own a luxurious sanctuary in the heart of Old Town Key West. Built in 2002 and a complete renovation in 2025, the furnished 3BD/2BA main home masterfully fuses island-contemporary style with timeless sophistication. Additional features include wrap-around porches,

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  813 Thomas St, Key West, FL 33040
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  /58

  $1,700,000

  • 4 Beds
  • 2 Baths
  • 2,016 Sq Ft

  1022 Fleming St, Key West, FL 33040

  Invest in Key West with this Duplex which can be also easily used as a single family home! Step into a piece of Key West history with this move in ready, light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this property offers easy living and generates income. Whether you're looking for a smart investment, a vacation getaway, or a new primary

  Ellen Gvili Ocean Sotheby's International Realty

  1022 Fleming St, Key West, FL 33040
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  /84

  $2,845,000

  • 4 Beds
  • 3 Baths
  • 1,800 Sq Ft

  529 Simonton St, Key West, FL 33040

  X Flood Zone 13ft above sea-level! Gorgeous CONCH home in the ultimate Old Town location - only one block from Duval, in a neighborhood lined with historic homes! Live in the heart of Old Town where charming architecture, iconic streetscapes, and Key West's finest restaurants and shops are right outside your door. This beautifully restored 1889 Conch home has been completely renovated in 2022 to

  Lisa Swanson The Agency Florida Keys

  529 Simonton St, Key West, FL 33040
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  /43

  $2,695,000 Open Sun 11:10AM - 2PM

  • 3 Beds
  • 3 Baths
  • 1,902 Sq Ft

  525 Louisa St, Key West, FL 33040

  An architecturally stunning renovation & upgrade of this classic Old Town Key West property is sure to meet all your needs. A welcoming front porch awaits as you depart from your rare 2 off-street parking spaces in Old Town, or alternatively, you may choose to arrive by bicycle & take advantage of the separate entrance with dedicated bike storage. A complete irrigation system with landscape

  Mike Caron Keller Williams Key West Compass Realty

  525 Louisa St, Key West, FL 33040
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  /45

  $2,849,000

  • 4 Beds
  • 5 Baths
  • 2,412 Sq Ft

  1223 Margaret St Unit 4, Key West, FL 33040

  SOLD AS YOU SEE IT! GORGEOUS Old Town Key West Luxury EXCELLENT VACATION RENTAL! Large 3 Story Home with Pool, Guest Cottage & Off Street Parking! Sleeps 10 people! Escape to paradise in this exquisite 2412sf 3 story home located in Old Town Key West close to the Casa Marina area. A rare blend of historic charm and luxury, this fully furnished, turnkey property invites you to live the island

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  1223 Margaret St Unit 4, Key West, FL 33040
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  /36

  $1,231,000

  • 3 Beds
  • 2.5 Baths
  • 1,017 Sq Ft

  609 Margaret St, Key West, FL 33040

  Charming remodeled 1929 Old Town Key West home on iconic Margaret Street, offering privacy, new impact windows & doors, flooring and timeless island feel. Set back from the street, this three-bedroom, two-bath residence feels like a peaceful retreat while remaining close to Duval Street and the historic seaport. The outdoor living space features a beautiful pool and spa area surrounded by a

  Sean Farrer Coldwell Banker Schmitt RE Co

  609 Margaret St, Key West, FL 33040
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  /36

  $1,350,000

  • 3 Beds
  • 3 Baths
  • 1,748 Sq Ft

  4 Aronovitz Ln, Key West, FL 33040

  Experience an authentic island lifestyle at this classic conch cottage nestled in the heart of Old Town. Located on a quiet lane, just steps to Duval Street and The Green Parrot, this updated home provides a unbeatable location for walking to all of the best spots in Key West. Designed in the iconic ''conch cottage'' style, the interior features Dade County Pine walls, vaulted ceilings, and

  Rodney Culiver Last Key Realty, Inc (KW)

  4 Aronovitz Ln, Key West, FL 33040
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  /38

  $765,000

  • 1 Bed
  • 1 Bath
  • 721 Sq Ft

  828 White St Unit 2, Key West, FL 33040

  Tucked into the heart of Old Town Key West's White Street Gallery District, this renovated 1-bedroom, 1-bath condo offers a rare blend of character, flexibility, and proven rental performance. With a strong history of seasonal and monthly rentals, it presents an appealing opportunity for both personal use and investment.One of the most unique features is the private first-floor entry, opening

  Michelle Blades Realty Executives Florida Keys Old Town

  828 White St Unit 2, Key West, FL 33040
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  /71

  $6,750,000

  • 5 Beds
  • 5 Baths
  • 3,663 Sq Ft

  411 Louisa St, Key West, FL 33040

  Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top dining and entertainment.This stunning five-bedroom, four-and-a-half-bath residence offers 3,663 sq. ft. of living space on an 8,227 sq. ft.oversized lot, providing rare space and privacy in one of the island's most desirable

  Bobby Coe RE/MAX Keys Connection (KW)

  411 Louisa St, Key West, FL 33040
• 

  

  /39

  $2,675,000 Open Sun 12PM - 3PM

  • 3 Beds
  • 4 Baths
  • 1,962 Sq Ft

  1017 Angela St, Key West, FL 33040

  The perfect embodiment of Key West located on a quiet lane in Old Town just a stroll from Duval Street and Historic Seaport. This cozy newly renovated, 3-bedroom, 3.5-bathroom home is the ultimate blend of calm island style inside and out. From the moment you arrive, 1017 Angela Street welcomes you with bold colors and playful design. The front porch offers an idyllic spot to start or end your

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1017 Angela St, Key West, FL 33040
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  /78

  $6,895,000

  • 6 Beds
  • 7 Baths
  • 3,425 Sq Ft

  317 Whitehead St, Key West, FL 33040

  Discover unparalleled luxury in the heart of Old Town, Key West. Comprised of a main house and guest cottage, this newly built ''Smart'' property infuses casual island elegance with modern sophistication. With a total of 6 bedrooms and 6.5 bathrooms, this home is an award winning architect-designed, custom-built luxurious property, complete with off-street parking, impact windows and doors, and

  Bobby Coe RE/MAX Keys Connection (KW)

  317 Whitehead St, Key West, FL 33040
• 

  

  /18

  $1,150,000

  • 3 Beds
  • 3 Baths
  • 1,152 Sq Ft

  844 Olivia St, Key West, FL 33040

  Charming Old Town Key West home blending historic island style with comfortable modern living. This well-maintained three-bedroom, two-bath residence features beautiful hardwood floors, abundant natural light, and inviting living spaces that create a relaxed Key West atmosphere. The functional layout works well for full-time living, a second home, or an income-producing investment property, with

  Rebecca Cobo Berkshire Hathaway HomeServices Knight & Gardner Realty

  844 Olivia St, Key West, FL 33040

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