Studio to 4 Bedroom Homes for Sale in Old Town

• 

  

  

  /18

  $599,000

  • 2 Beds
  • 1 Bath
  • 612 Sq Ft

  1042 United St, Key West, FL 33040

  Discover your perfect Key West getaway at 1042 United Street -- a charming single-story cottage with two bedrooms, one bath, and all the island character you've been dreaming of. Relax on the inviting front porch with your morning coffee, then unwind on the private back patio after a day of sun and sea. Bright, open interiors and a seamless indoor-outdoor flow make this home ideal for easy

  Barbara Crespo Keller Williams Key West Compass Realty

  1042 United St, Key West, FL 33040
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /47

  $2,150,000

  • 3 Beds
  • 4 Baths
  • 1,522 Sq Ft

  816 Ashe St, Key West, FL 33040

  NEW PRICE!! This beautifully renovated conch home is a proud recipient of the 2024 Historic Florida Keys Foundation Preservation Award. Originally built in 1906, it has been meticulously restored from the ground up, essentially making it a brand-new property. The home features off-street parking, a heated/chilled pool, and comes fully furnished, offering a turnkey experience. Situated within

  Bascom Grooms Bascom Grooms Real Estate (KW)

  816 Ashe St, Key West, FL 33040
• 

  

  

  /28

  $850,000

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft

  817 Eaton St Unit 1, Key West, FL 33040

  MOTIVATED SELLERS' A must see this desirable beautiful bright condo located in the heart of historic Old Town area. This charming 1 bedroom 1 bath home offers high ceilings, with open spacious floor plan. The perfect spot within walking distance of great restaurants and a few blocks to the Historic Seaport and the famous Duval Street. OWNERS MAY HAVE A PET WITH ASSOCIATION APPROVAL.

  Letisia Powell Robert Slack LLC

  817 Eaton St Unit 1, Key West, FL 33040
• 

  

  

  /41

  $1,550,000

  • 2 Beds
  • 2 Baths
  • 1,207 Sq Ft

  800 Fleming St Unit B-3, Key West, FL 33040

  Perfectly situated just three blocks from Duval Street and two from the grocery store, this one-of-a-kind, fully furnished penthouse has been meticulously renovated to deliver unmatched luxury living in the heart of Old Town Key West. Offering rare off-street parking, this light-filled residence is perched among the treetops and features a private balcony with serene pool and garden views.Inside,

  Solaris Gregory Expert Realty LLC (HQ)

  800 Fleming St Unit B-3, Key West, FL 33040
• 

  

  

  /10

  $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
• 

  

  /49

  $2,599,000

  • 4 Beds
  • 4 Baths
  • 1,854 Sq Ft

  1320 Eliza St, Key West, FL 33040

  Welcome to the School House on Eliza!1320 Eliza Street is a stunning corner-lot property that exudes old-world charm and proudly served as a historic schoolhouse in Key West.This four (4) bedroom with two (2) full bathrooms with two (2) half bathrooms home sits on a tropically landscaped corner lot with great outdoor living and a perfect heated pool. A brand new roof was just installed.The main

  Bobby Coe RE/MAX Keys Connection (KW)

  1320 Eliza St, Key West, FL 33040
• 

  

  /47

  $2,549,000

  • 3 Beds
  • 3 Baths
  • 1,916 Sq Ft

  312 Margaret St, Key West, FL 33040

  Welcome to your perfect Island Escape! Nestled in the heart of old town, this beautiful home is one you're sure to fall in love with. Featuring two off-street parking spaces and a private pool, it blends luxury, comfort, and convenience, perfect for both vacation getaways and year-round living. Inside, you'll find three spacious bedrooms and three modern bathrooms, designed to provide everything

  Andy Birrell Berkshire Hathaway HomeServices Knight & Gardner Realty

  312 Margaret St, Key West, FL 33040
• 

  

  /40

  $2,850,000

  • 3 Beds
  • 3 Baths
  • 1,519 Sq Ft

  610 Griffin Ln, Key West, FL 33040

  Tucked away on a quiet lane in the heart of Old Town Key West, this rare compound blends timeless island charm with exceptional privacy--just steps from premier dining, shopping, and entertainment. Three distinct dwellings are arranged around a serene brick courtyard with a heated cocktail pool, creating an inviting retreat in one of the most sought-after neighborhoods in Key West.The main home

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  610 Griffin Ln, Key West, FL 33040
• 

  

  /35

  $1,175,000

  • 2 Beds
  • 1 Bath
  • 723 Sq Ft

  729 Windsor Ln, Key West, FL 33040

  Charming Historic Gem in the Heart of Old Town Key West!Welcome to 729 Windsor Lane--a rare opportunity to own a piece of Key West history nestled in one of the island's most desirable residential neighborhoods. Set on an expansive nearly 3,000 sq.ft. lot, this classic home offers a generous footprint that's almost unheard of in Old Town, along with the luxury of coveted off-street parking.Step

  Amber DeBevec LoKation Real Estate

  729 Windsor Ln, Key West, FL 33040
• 

  

  /6

  $1,900,000

  • 3 Beds
  • 1 Bath
  • 1,368 Sq Ft

  511 Tabby Way, Key West, FL 33040

  Unmatched Old Town Opportunity!Location, Location, Location! This is your chance to own one of the most coveted properties in Old Town Key West--a truly unique home and lot that must be seen to be fully appreciated. Tucked away and completely hidden from view, this remarkably private property is the only single-family home currently on the market with direct pedestrian access to Duval Street via

  Paige Bethel Island Home Realty Inc.

  511 Tabby Way, Key West, FL 33040
• 

  

  /7

  $999,999

  • 3 Beds
  • 2 Baths
  • 1,421 Sq Ft

  620 White St, Key West, FL 33040

  This legal duplex offers fantastic potential with two separate units. The front unit is a 2-bedroom, 1-bath home and a rear unit is a 1-bedroom, 1-bath unit. The property features an in-ground pool and is ideally laid out for investment or owner-occupancy with rental income. While some work has been done, the entire property is in need of finishing renovations-- perfect for a buyer ready to

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  620 White St, Key West, FL 33040
• 

  

  /6

  $1,050,000 Pre-Foreclosure

  • 1 Bed
  • 2 Baths
  • 1,095 Sq Ft

  709 Frances St, Key West, FL 33040

  This Conch home has been opened up to provide a large living room with high ceilings and a great sense of space. It features original Dade Pine walls and custom built-in bookcases. The Dade County pine looks to be in beautiful condition. The entire upstairs is the primary bedroom plus a half bath and an enormous walk in closet, office and plenty of storage. The kitchen, dining room and full bath

  Laura McChesney Preferred Properties (KW)

  709 Frances St, Key West, FL 33040
• 

  

  /34

  $1,995,000

  • 1 Bed
  • 3 Baths
  • 1,526 Sq Ft

  830 Caroline St, Key West, FL 33040

  Endless possibilities await with this mixed-use building perfectly positioned in the heart of Old Town's Historic Seaport neighborhood. This rare property blends residential and commercial flexibility in one of Key West's most sought-after locations.The second floor features a stylish studio apartment with two lofts, wood floors, a full bath, vaulted ceilings, peekaboo water views, and a private

  Solaris Gregory Expert Realty LLC (HQ)

  830 Caroline St, Key West, FL 33040
• 

  

  /24

  $1,345,000

  • 4 Beds
  • 2 Baths
  • 1,660 Sq Ft

  625 Whitehead St, Key West, FL 33040

  Prime Old Town Mixed-Use Property - Live, Work, or Invest! Ideally situated in Old Town Key West, this Historic Residential Office (HRO) zoned property offers a rare opportunity for both residential and commercial use. Previously, home to a successful spa, it's perfectly suited for continuing as a business or transforming into a private residence. Filled with character, the space features

  Kate Green Old Town Realty

  625 Whitehead St, Key West, FL 33040
• 

  

  /37

  $1,442,100

  • 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
• 

  

  /36

  $1,850,000

  • 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
• 

  

  /21

  $459,000

  • 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 property is just few a few blocks from vibrant Duval Street, known for entertainment and dining options and additionally, it's within walking distance to the dog park, beaches, wildlife

  The Spottswood Team Truman & Co. (KW)

  1124 Catherine St Unit 201, Key West, FL 33040
• 

  

  /23

  $865,000

  • 2 Beds
  • 2 Baths
  • 712 Sq Ft

  508 Louisa St Unit 3, Key West, FL 33040

  Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offers an incredible opportunity. Currently utilized as an income-producing vacation rental, this home presents the perfect blend of comfort and convenience.Nestled in the heart of Key West, this condo boasts proximity to renowned attractions, vibrant restaurants, and the

  Paul Brooks Compass Florida, LLC

  508 Louisa St Unit 3, Key West, FL 33040
• 

  

  /24

  $1,199,990

  • 3 Beds
  • 1 Bath
  • 1,231 Sq Ft

  705 Chapman Ln, Key West, FL 33040

  Charming Old Town gem with endless possibilitiesDiscover a rare opportunity in the heart of Old Town Key West! This property sits on an exceptionally large lot -- a true find in this historic neighborhood. With plenty of room to expand, you can create your own island oasis by adding a pool, enlarging the existing home, or even building a separate guest cottage.Just a short stroll to lively Duval

  Joanne Tarantino Berkshire Hathaway HomeServices Knight & Gardner Realty

  705 Chapman Ln, Key West, FL 33040
• 

  

  /43

  $2,800,000

  • 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
• 

  

  /15

  $1,299,000

  • 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
• 

  

  /40

  $2,849,000

  • 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 Vazquez Truman & Co. (KW)

  410 Louisa St, Key West, FL 33040
• 

  

  /29

  $3,295,000

  • 2 Beds
  • 3 Baths
  • 1,650 Sq Ft

  806 Southard St, Key West, FL 33040

  Welcome to your private oasis in the heart of Old Town Key West, where modern luxury meets historic charm. This beautifully renovated home perfectly blends timeless island architecture with sleek, contemporary comforts, offering an unparalleled living experience just steps from the Seaport and world-renowned Duval Street. Behind its classic facade, an airy, open floor plan awaits, thoughtfully

  Richard Patten Your Keys Real Estate, LLC

  806 Southard St, Key West, FL 33040
• 

  

  /45

  $5,495,000

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

  1006 Fleming St, Key West, FL 33040

  Exceptional Old Town compound with pool, gardens, and two 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 four-and-a-half baths.

  Terri Spottswood Truman & Co. (KW)

  1006 Fleming St, Key West, FL 33040
• 

  

  /9

  $799,900

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft

  1014 Truman Ave Unit 3, Key West, FL 33040

  1014 Truman Avenue - Modern Island Elegance in the Heart of Key WestWelcome to a Key West retreat where modern design meets the island's laid-back charm. This immaculate two-bedroom, two-bath condominium has been masterfully remodeled with designer finishes, offering a home that's as stylish as it is functional.Step inside to a sunlit, open-concept living space where clean lines and bamboo

  Dominic Paolillo Jr. Truman & Co. (KW)

  1014 Truman Ave Unit 3, Key West, FL 33040
• 

  

  /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
• 

  

  /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
• 

  

  /42

  $4,595,000

  • 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
• 

  

  /43

  $3,595,000

  • 4 Beds
  • 4 Baths
  • 1,968 Sq Ft

  510 Margaret St, Key West, FL 33040

  510 Margaret Street and 3 Scheppens Lane deliver an unparalleled island retreat. Ideally positioned on one of the most coveted streets in the heart of Old Town, this light-filled 4BD/4BA compound offers both comfort and privacy. The beautifully updated 3BD/3BA main residence features restored Dade County Pine walls, striking hardwood floors, Verde granite countertops, Thermador stainless

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  510 Margaret St, Key West, FL 33040
• 

  

  /55

  $3,999,000

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

  813 Thomas St, Key West, FL 33040

  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, this impeccably 4BD/3BA home masterfully fuses island-contemporary style with timeless sophistication. Located on a rare double lot in the coveted X flood zone, the 3/2 main house welcomes you with wrap-around porches, soaring ceilings,

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  813 Thomas St, Key West, FL 33040
• 

  

  /49

  $1,999,990

  • 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 fully renovated, 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
• 

  

  /29

  $2,299,000

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft

  1116 Elgin Ln, Key West, FL 33040

  This quintessential two story, 3/2 Key West home is situated in the Historic Seaport District on a quiet lane with coveted off street parking.....The original structure can be traced back to the 1850s and has many beautiful historic features such as Dade County Pine walls and flooring. The home has a wonderful open design with the kitchen overlooking the large, vaulted living/dining area. A wall

  Rob Severin Rob Severin Real Estate Co

  1116 Elgin Ln, Key West, FL 33040
• 

  

  /47

  $1,995,000

  • 3 Beds
  • 3 Baths
  • 2,205 Sq Ft

  421 United St, Key West, FL 33040

  This super cute historic Old Town Key West 2,205 sq. ft. Conch-style home is perfectly positioned just steps from famous Duval Street and one block from the ocean, South Beach, and the Southernmost Point. If you're seeking the best location in Key West--walkable, vibrant, and effortless--this property is unmatched. The sun-filled first floor showcases timeless Dade County pine, cherry floors, and

  Timothy Swanson The Agency Florida Keys

  421 United St, Key West, FL 33040
• 

  

  /84

  $2,975,000

  • 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
• 

  

  /21

  $1,625,000

  • 2 Beds
  • 3 Baths
  • 1,959 Sq Ft

  1011 Truman Ave, Key West, FL 33040

  1011 Truman Avenue is a stylish mixed-use property located in the heart of Old Town, Key West. The building includes three legal units with one covered off street parking space and sits in the desirable X-Flood Zone. The ground floor features a 795 sq. ft. professional office space with an industrial feel and a half bath, along with a 416 sq. ft. one-bedroom unit that includes a full bathroom and

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  1011 Truman Ave, Key West, FL 33040
• 

  

  /24

  $1,249,000

  • 3 Beds
  • 3 Baths
  • 2,080 Sq Ft

  611 Simonton St, Key West, FL 33040

  NEW PRICE! Fantastic Key West location in the heart of Old Town Key West. Close to famous Duval Street, Historic Seaport, fine dining, galleries and more. Spacious two story home with 2,080 sq ft of living space. Three bedrooms and three full baths. Fenced yard. Patio Space. French Doors. Lanai area. Off street parking for one small vehicle. Seller financing possible with minimum 30% down!

  Bascom Grooms Bascom Grooms Real Estate (KW)

  611 Simonton St, Key West, FL 33040
• 

  

  /44

  $2,949,000

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

  1223 Margaret St Unit 4, Key West, FL 33040

  Turnkey Old Town Key West Luxury - Pool, Guest Cottage & Parking Escape to paradise in this exquisite 2412sf 3 story home located in Old Town Key West not far from the Casa Marina area. A rare blend of historic charm and luxury, this fully furnished, turnkey property invites you to live the island dream or step into a ready-to-go monthly vacation rental opportunity. Inside, discover airy open

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  1223 Margaret St Unit 4, Key West, FL 33040
• 

  

  /43

  $2,499,000

  • 3 Beds
  • 2 Baths
  • 1,665 Sq Ft

  1119 Whitehead St, Key West, FL 33040

  This stunning Old Town residence offers the perfect blend of historic charm and modern elegance, just one block from Duval Street and three blocks from the world-famous Southernmost Point. This 3 bedroom, 2 bath home was fully renovated in 2018. and features a private gated courtyard, off-street parking, and high-end finishes throughout.Enjoy effortless indoor-outdoor living with a thoughtful

  Jenna Blackwell Berkshire Hathaway HomeServices Knight & Gardner Realty

  1119 Whitehead St, Key West, FL 33040
• 

  

  /40

  $2,880,000

  • 2 Beds
  • 3 Baths
  • 2,940 Sq Ft

  626 Grinnell St, Key West, FL 33040

  Tucked away in the coveted flood X zone of Old Town, the elegant William H. Malone House offers an exceptional blend of historic character and refined modern living. This expansive 2,940 square foot residence features exquisite architectural details, off-street parking for two, a heated pool and spa, whole home generator, and spacious covered porches--offering a tranquil private retreat mere

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  626 Grinnell St, Key West, FL 33040
• 

  

  /32

  $1,099,000

  • 2 Beds
  • 2 Baths
  • 896 Sq Ft

  808 Virginia St Unit 4, Key West, FL 33040

  Private Pool, Parking and Proximity to it all!This is your perfect townhome in the heart of Old Town. Lock and Go is the key for this quintessential Key West property! With Very Low Monthly Expenses!Two (2) Bedrooms, One (1) Full bathroom and a (.5) half bathroom but don't forget the outdoor shower, which makes it a Key West full bathroom, and with a private pool just outside for you to enjoy

  Bobby Coe RE/MAX Keys Connection (KW)

  808 Virginia St Unit 4, Key West, FL 33040

Showing Results 41 - 80, Page 2 of 3