This charming duplex is an excellent value. Located near White Street, the beaches and pier, it's an easy walk to everything. Each spacious unit has its own entrance and private outdoor space. Downstairs is a one bedroom, one bath with living, kitchen, dining open concept. Ample closets, full size washer/dryer and high ceilings are an added bonus. There is a bricked off street parking space. The

Laura McChesney Preferred Properties (KW)

Live & Work in the Heart of Old Town Key West!An exceptional opportunity to own both a commercial space and a residential condo in one of Key West's most vibrant and high-visibility locations. Located directly on bustling Truman Avenue across from the historic Harvey Government Center, this concrete-constructed commercial condo features large storefront windows, flexible interior space, and four

Ellen Gvili Ocean Sotheby's International Realty

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)

NEW LISTING!!! First time on the market since the mid 70s! Prime Old Town Location mixed-use property. Endless possibilities with this corner location in the heart of the historic district and just two blocks from the Seaport. Commercial space with full bath and occupied by successful gallery tenant. Three Residential apartments with 1BED/1BATH each. Corner of Fleming and Margaret St near

Bascom Grooms Bascom Grooms Real Estate (KW)

Zen Villa represents a rare opportunity in the heart of Old Town, Key West, comprised of three homes on a spacious 5,891 SF lot. The main residence at 400 Aronovitz Lane is a luxurious 3-bedroom, 4-bathroom contemporary island estate and an active vacation rental, while 621 and 623 Whitehead Street offer two charming 1-bedroom, 1-bathroom cottages, currently rented long-term.The main home

Damian Vantriglia Berkshire Hathaway HomeServices Knight & Gardner Realty

Triplex with Stunning Rent Roll ($187,200/year)- This income-producing triplex features three well-maintained units, each offering 3 bedrooms and 2 bathrooms. The front unit, originally larger than the rear units and spans one level--ideal for tenants seeking single-story living. The rear units are two-story layouts, with bedrooms and baths upstairs and kitchen/living areas on the main level.

Kayley Arn Coldwell Banker Realty - Aventura

Duplex with Solid Rent Roll ($91,800/year) - This income-producing duplex features 2 well-maintained units, each offering 3 bedrooms and 1 bathrooms. Units are rented for $3,850 and $3,800 per month on long-term leases ($91,800/year). Perfectly positioned near the coast and only a short ride from the energy of downtown.

Kayley Arn Coldwell Banker Realty - Aventura

Situated in the heart of Old Town Key West, this exceptional multi-family property offers four well-maintained 2-bedroom, 1-bathroom apartments--perfectly positioned for strong, consistent rental income. Just a short stroll to Duval Street, renowned restaurants, the Truman Waterfront, and local attractions, this property is ideally located for long-term or monthly rentals.Each unit features a

Richard Haskins Buy The Keys

Unique opportunity for a creative buyer to own this 3 residential unit property. Would be a great for business owner looking for employee housing. Update all 3 homes for a family compound. Currently setup as roommate style living with a gross income of $15,000. a month. Don't miss this great location in Bahama Village steps from the Truman Waterfront, Ft. Zach beach, restaurants, galleries, shops

Wendy Zintsmaster Truman & Co. (KW)

Excellent income producing rental property and/or employee housing with multiple units. All apartments are currently rented at below market rents. With its downtown location, low flood risk, and turn-key income, this property is perfectly positioned for savvy investors. Three 1bed 1bath units, One 2 bed 1 bath separate cottage. One studio. Please note that advanced notice is required to arrange

Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

Old Town 'Diamond in the Rough' across from Bay View Park with the highly coveted Off-Street parking. City of Key West recognizes this property as a duplex with two ROGO's. Two story main house along with detached cottage. County Property appraiser says main house is 1900+sq ft, with cottage of 300+ sq ft. Does have off-street parking and possibly room for a pool. Lots of potential. Major

Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

Don't miss this rare opportunity to own a legal duplex on a spacious 10,000 SqFt corner lot! The main residence, solid CBS construction, offers 2 bedrooms, 2 bathrooms, and a generous 2,004 SqFt of living space. The open-concept layout features a large living room, a well-appointed kitchen with an adjoining dining area, and plenty of natural light. There's also a garage, laundry room, and

Keys Team Bryant and Kat Expert Realty LLC (HQ)

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

Fabulous Find on the Atlantic Side of Key West!Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing

Irina Pytlik Keys Top Realty LLC

If you are looking for location and a historic home, this triplex is tucked away on one of Old Town Key West's most peaceful lanes. This charming Conch home won the distinguished Historic Florida Keys Preservation Star in 1988 and has been in the same family for over 40 years--a true testament to its warmth, character, and enduring appeal.The main house features generously sized rooms, high

Ellen Gvili Ocean Sotheby's International Realty

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

This historic 4 unit property was at one time a single family home and could be converted back to same. Currently configured as 3 apartments in the main building, you'll find treasured Dade County Pine and hardwood floors throughout. In the downstairs apartment comprising the entire first floor there is Hansen & Bringle cabinetry, central A/C and it's own washer/dryer. Upstairs are 2 studio

Suzanne Washburn Coldwell Banker Schmitt Real Estate Co. (KW)

Nestled on one of the most coveted blocks in Key West, this exceptional property in the Historic District is brimming with character and untapped potential. Currently configured as four distinct apartments - (A) 2BR/1BA, (B) 2BR/2BA, (C) Studio/1BA, and (D) 1BR/1BA - totaling 2,671 sq. ft., each unit features its own private outdoor space, a well-appointed kitchen, ample storage, and high

Team Kaufelt Truman & Co. (KW)

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

Investment opportunity! This Duplex features a 3 bedroom and 1 bath main home with carport, separate addresses (Front & Rear) & utilities. The 1 bed/1 bath concrete block structure is 553 square feet, built in 1958 with its own driveway and side yard. There is a small shed for extra storage. The combined (under market) rentals are just over $4,500/month with leases in effect through June 2026 for

Andrea Weitz Island Life Realty Experts

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

The Behmke Group Keller Williams Key West Compass Realty

Prime Mixed-Use Investment Opportunity in Key West!Built in 2021 to current building codes, this exceptional four-unit commercial and residential compound is a rare find in the heart of Key West. A perfect 1031 Exchange candidate, this versatile property includes two licensed townhouse residences and two licensed commercial units, offering excellent income potential and flexibility.The commercial

Team Spottswood/Vazquez Truman & Co. (KW)

Invest in Key West with this legal Duplex! 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 residence, this property is ready for you. Live in

Ellen Gvili Ocean Sotheby's International Realty

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)

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

This home offers a unique opportunity for flexible living or investment! Currently configured as a single-family residence, it has been approved by the City of Key West to be reverted back to a Multi-family, allowing for up to 4 units. Easily convert the home back to two studios with bath, 1 bedroom 1 bath and a 2 bedroom 1 bath. Welcome to 1409 Truman Avenue, a stunning Key West Eyebrow home

Michael Sorah Truman & Co. (KW)

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)

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)

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)

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)

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)

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)

This charming four-bedroom, three-bathroom duplex is a rare find, nestled on a generous 7,500 sq. ft. lot that provides plenty of room for relaxation, gardening, or entertaining. Surrounded by lush foliage, the property offers a serene sense of privacy and seclusion, making it a perfect retreat. Centrally located, you'll enjoy easy access to shopping, dining, and the beach, with Old Town Key West

Justyn Ewald Expert Realty LLC (HQ)

This home has not been sold in over 100 years! The property sits on the corner of world famous Millionaire Row and one of the last not to be renovated. Do not buy someone else's overpriced flip. Bring your imagination, contractor and bring this home back to its original beauty. The lot is almost 5000 SF and runs from Fleming St. to Stickeny Lane, where there is ample off-street parking. The 1890

Derek Epperly Keys Atlantic Realty

Yes - not too good to be true or a misprint! Priced to sell for just $990,000 with this $400,000 price reduction. Rare 2 unit property in Old Town! Enjoy Key West living on one of our most picturesque Old Town lanes. Located in the heart of the historic district and near the seaport, everything you want in Key West is right out your door. Built in the early 1900s, over the years the home was

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

INVESTOR ALERT! Great opportunity to own a 3 unit building centrally located in Key West with off Street parking and plenty of room for a pool. The downstairs front unit is a 2BD/1BA, has an open floor plan with lots of windows allowing for plenty of natural light and a cute front porch. The upstairs unit is a 1BD/1BA and the rear third unit is another 2BD/1BA. The multi unit building sits on a

Team Spottswood/Vazquez Truman & Co. (KW)

Step into Key West history with this remarkable property, available for the first time in generations! Located just a block from world-famous Duval Street and across from the Federal Courthouse, this property at 314 Simonton Street offers a unique blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, this three-level building is steeped in

Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

At the best location in the heart of old town you will find this great duplex on Julia street in between Duval street and Whitehead street, 86 FOOTSTEPS TO DUVAL STREET. The back is a two bedroom two bathroom with a nice back yard. And in the front is a recently renovated one bedroom with two bathrooms with high ceilings and a great loft. It has an outdoor shower. A new A/C was installed 01/24.

Annica Pedersen Key West Luxury Real Estate Inc (KW)

BIG TIME INVESTMENT OPPORTUNITY in the heart of the Historic District of Key West. Originally built as a former church, this 4 unit active rental property offers 3,383 square feet of living space, featuring 8 bedrooms and 4 bathrooms, and currently generates $10,908.50 in monthly rental income. (See below for a breakdown of beds and baths per unit) With versatile possibilities, it has the

Team Kaufelt Truman & Co. (KW)