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$895,000
Key West
Island City Subdivision   - MM: 2.00
4 Bed, 4 Baths, 2,236 SqFt Days Listed: 16
Duplex - Contingent - Waterfront No
Side of Island: Median - Dockage: None

Old Town Duplex across from Bay View Park. Two story main house along with detached cottage. Lots of potential. Major renovation project. Foundation issues, evidence of termites, plus leaking roof. Does have off street parking. Being sold as is with no repair and no clean up by seller. Needs cash buyer. Proof of funds required before showing. Please do not disturb the occupants.

$899,000
Key West
Old Town Unlisted   - MM: 1.00
2 Bed, 2 Baths, 936 SqFt Days Listed: 215
-30.79% ($400,000) 2 Price Changes : Last Change 64 Days Ago
Duplex - Contingent - Waterfront No
Side of Island: Ocean - Dockage: None

This charming Old Town property offers the perfect blend of historic character and future potential just steps from world-famous Duval Street. Rich with the classic charm of Old Key West, this property is a blank canvas waiting for your personal touch. The permitted main home features two spacious bedrooms, a bonus den that can easily function as an additional bedroom or office, a full bathroom, and living and kitchen areas. A private courtyard leads to a non-conforming 2nd building which includes a kitchenette, living area, two additional bedrooms and 2 bathrooms which possibly could be converted to legal living quarters which would have to be applied for through the City of Key West and which additional fees would have to be paid. A covered carport provides shaded parking for one vehicle, with additional street parking available. Located just a short walk from iconic Duval Street, the Ernest Hemingway House, the historic Key West Lighthouse, Truman Waterfront Park, and the tranquil shores of Fort Zachary Taylor State Park, this Old Town retreat offers an unparalleled Key West lifestyle nestled in a prime location. Just a short stroll to world-renowned dining, vibrant nightlife, picturesque parks and the historic seaport with endless dining, entertainment, and cultural attractions nearby, this property is the perfect blend of convenience and charm.

$980,000
Key West
Moffats Subdivision   - MM: 2.00
2 Bed, 2 Baths, 1,095 SqFt Days Listed: 176
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

This charming duplex has much to offer. A great location, two very nice one bedroom, one bath units, each with their own entry and outdoor space and its in move in condition. The first floor features a primary bedroom with Dade Pine walls and a large closet. The kitchen/living/dining area opens to the private exterior deck. Upstairs the 1/1 has high ceilings and natural light. It has a porch in the front and back and gated entry at the staircase. Bricked off street parking can accommodate a small car plus gated area for bikes and storage. There is mature landscaping in the front adding to the privacy for the property both upstairs and down. Each unit has their own washer/dryer. 1312 Catherine is located near White Street, conveniently located to shopping and nearby Bayview park. The property is freshly painted, well maintained and move in ready. Super investment value at $490,000 per unit or live in one and rent the other for added income.

$990,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 1,296 SqFt Days Listed: 191
-33.56% ($500,000) 3 Price Changes : Last Change 3 Days Ago
Duplex - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

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 converted into a legal 2-unit property with separate water & electric accounts. The configuration is upstairs (large 1 BR & 1 BA with a sleeping loft) and downstairs (2 BR & 1.5 BA) units, with an exterior staircase. Both units have a front & rear porch, balcony, or deck. For your parking convenience, an off-street spot is in front of the property.Prime location, opportunity & value!

$1,069,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
4 Bed, 4 Baths, 1,785 SqFt Days Listed: 106
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

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 both houses. Renovate or rebuild! Please allow 24 hours notice for scheduled showings.

$1,149,000
Key West
Island City Subdivision   - MM: 2.00
3 Bed, 3 Baths, 1,740 SqFt Days Listed: 113
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

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 second-floor has 1 bedroom, 1 bath, hardwood floors and a large rear porch. The location of this current 2-unit property offers an excellent investment potential or possible single family home conversion. Located just off White Street.

$1,150,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 1,421 SqFt Days Listed: 34
-4.09% ($49,000) 1 Price Change : Last Change 2 Days Ago
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

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 customize and maximize value.

$1,154,900
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
6 Bed, 6 Baths, 1,694 SqFt Days Listed: 65
-3.36% ($40,100) 2 Price Changes : Last Change 2 Days Ago
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

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.

$1,199,000
Key West
Benj Alburys Subdivisiond   - MM: 2.00
4 Bed, 4 Baths, 1,504 SqFt Days Listed: 179
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

Unleash your vision and step into endless possibilities with this two-story duplex, a blank canvas located in the prestigious Meadows neighborhood of Key West. Packed with potential, this diamond in the rough is perfect for investors, developers, or dreamers looking to craft their masterpiece in one of Key Wests most desirable areas. The property is a blank slate for your imagination to design and transform. Envision two luxurious 2-bedroom, 2-bathroom residences, each tailored to your exact specifications. Whether your goal is a chic modern retreat, a classic Key West-style hideaway, or a profitable income property, the layout offers endless flexibility to bring your ideas to life. Nestled on a tranquil street in the highly sought-after Meadows, this property offers a peaceful escape while keeping you mere moments from Key Wests iconic attractions, vibrant nightlife, and renowned dining. Stroll down tree-lined streets, enjoy nearby waterfront views, and embrace the neighborhoods charming character--all while being close to the energy of Duval Street and the historic district. With renovation already started, this is your opportunity to take the reins and shape two high-end residences or craft the ultimate single-family sanctuary. Whether youre dreaming of a personal paradise, planning for vacation or long-term rentals, or developing a profitable multi-unit property, the potential for return on investment here is unparalleled. With its unbeatable location, untapped potential, and blank canvas, this property is ready to shine under your vision. Dont let this rare opportunity slip away.

$1,249,000
Key West
Sunshine Subdivision Plat 3   - MM: 3.00
4 Bed, 4 Baths, 1,740 SqFt Days Listed: 186
-3.85% ($50,000) 1 Price Change : Last Change 85 Days Ago
Duplex - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

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, youll enjoy easy access to shopping, dining, and the beach, with Old Town Key West just a short walk or bike ride away. This prime location truly offers the best of both worlds--convenience and tranquility.Currently, this property is a fantastic income-producing opportunity, generating a total of $8,500 per month in long-term rental income. The potential is limitless: live in one side and rent out the other for additional income, or rent out both sides to maximize your return on investment. Dont miss out on this incredible opportunity! Call today to schedule a showing and explore the possibilities this duplex has to offer!

$1,300,000
Key West
Pearlman Heights   - MM: 4.00
5 Bed, 5 Baths, 2,016 SqFt Days Listed: 83
Multi-Units - Contingent - Waterfront No
Side of Island: Median - Dockage: None

Welcome to 1006 16th Terrace, a charming two-story residence nestled in the New Town area of Key West, Florida. This well-maintained home boasts 5 bedrooms and 3 bathrooms offering a floorplan that will accommodate multiple situations. The exterior of the home is a testament to meticulous landscaping, creating a serene and inviting atmosphere. A large, detached storage unit provides additional space for a multitude of uses. The residence features a two central air conditioning systems, ensuring optimal comfort throughout the year. The home has been recently painted, adding to its fresh and well-kept appearance. The original ground level home was built in 1965; however, the second story addition was built in 1993. The home is equipped with storm rated windows and doors for your added protection Whether you are looking for a family home or a multi-family arrangement, this property at 1006 16th Terrace combines comfort, functionality and the charm of Key West living. Call today for your private showing.A Matterport virtual tour has just been added...Take a look

$1,345,000
Key West
Land Buyers Assn   - MM: 3.00
3 Bed, 3 Baths, 1,344 SqFt Days Listed: 101
-3.58% ($50,000) 1 Price Change : Last Change 2 Days Ago
Duplex - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Legal Duplex in Prime Key West Location! This thoughtfully updated CBS duplex offers a unique opportunity for multi-family living, employee housing, or generating rental income. Unit A features 2 bedrooms, 1 bath and a private entrance leading to a lushly landscaped yard with an outdoor shower, a clawfoot tub, irrigation and a mature mango tree. Each bedroom has an option for a private entrance. Unit B is a true 1 bedroom, 1 bath with a separate entrance and a private yard, perfect for guests or tenants. Each unit is separately metered features tile flooring throughout, impact windows & doors, private washer/ dryer and full kitchen. Whether you choose to live in one unit while renting the other to offset expenses or maximize income by leasing both, this duplex is a versatile investment and move in ready. Dont miss this rare opportunity to own a well-maintained property just steps away from White Street Pier, The Casa Marina, and Higgs Beach.Owner is a licensed real estate agent.

$1,399,000
Key West
Benj Alburys Subdivisiond   - MM: 2.00
3 Bed, 3 Baths, 1,932 SqFt Days Listed: 153
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

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 that combines historical charm with modern amenities. The spacious layout and design make it easy to transition back to a mult-family configuration of a duplex, triplex or 4 units.. Each potential unit could offer comfortable living spaces, with the square footage allowing for a range of layouts to suit tenants needs.Based on comparable rentals in the area and the square footage of this property, each unit could command an estimated monthly rent of $3k to 6k monthly, each unit (seasonal variables) providing a lucrative investment opportunity. With the strong rental demand in Key West, this property is perfectly positioned to maximize its potential.Whether youre looking to generate income, create a multi-generational living space, or invest in the vibrant Key West market, this property is a rare find. Contact us for more details and to schedule a showing!

$1,425,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,464 SqFt Days Listed: 224
-1.72% ($25,000) 1 Price Change : Last Change 88 Days Ago
Duplex - Active - Waterfront No
Side of Island: Ocean - Dockage: None

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. When you are sitting on your front porch its hard to believe that you are in between the two busiest streets as Julia street is a really quiet and cute street! Dont miss out on this great opportunity!

$1,449,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
4 Bed, 4 Baths, 2,664 SqFt Days Listed: 18
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

Dont 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. Theres also a garage, laundry room, and potential to easily add a third bedroom.The separate 2-bedroom, 1-bath cottage spans 660 SqFt--perfect for rental income, extended family, or a private guest house.Outside, the expansive yard offers endless possibilities. With plenty of space for a custom patio, outdoor kitchen, or fire pit, its the ideal setup for entertaining, weekend gatherings, or simply enjoying the outdoors. Plenty of parking for multiple vehicles, a boat, or a trailer--perfect for those who need both space and versatility.Whether youre an investor or looking for a multi-generational living solution, this property is packed with potential and ready to make your vision a reality!

$1,499,000
Key West
Investment Co Subdivision   - MM: 1.00
3 Bed, 3 Baths, 1,148 SqFt Days Listed: 119
-11.77% ($200,000) 2 Price Changes : Last Change 53 Days Ago
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

Behind the quintessential white picket fence you will find this delightful historic cottage currently set up as a duplex with off street parking and pool. Lots of opportunity with the ability to generate income and have your own slice of Paradise to enjoy, or marry the spaces and convert to a single family dream home. Each unit enjoys privacy from the other including separate outdoor living spaces. The front unit greets you with the charming and spacious front porch. Through the front door you will enter into an open living room and kitchen with fabulous ceiling heights, charming architectural details and 1bd/1ba plus a loft for storage. Enter the backyard oasis down a brick lined sidewalk that opens up to a sprawling deck surrounding a refreshing and sunny swimming pool. The rear unit enjoys 2bd/1ba with open kitchen/living space that leads to a covered porch overlooking the backyard retreat!

$1,500,000
Key West
Moffats Subdivision   - MM: 2.00
4 Bed, 4 Baths, 2,019 SqFt Days Listed: 125
-31.79% ($699,000) 2 Price Changes : Last Change 32 Days Ago
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

Are you ready to build??? after talking with City Planning the new owner will be able to possibly renovate the main house and build a second new house Buyer to verify...Make your offer today.Welcome to 1327 Duncan Street, this property offers a 3 bedroom 1 bath single-family home plus a separate 1 bedroom 1 bath cottage with fenced in yard, laundry area, central air condition. The main house has 12 ft ceilings, laundry room, living room, dining room, storage room with pull down attic access. There is also a large storage building in the backyard. The large lot offers many possibilities for the new owners. The two units have separate electric and water meters and sewer accounts . ..Make your offer today.

$1,599,900
Key West
Moffats Subdivision   - MM: 2.00
5 Bed, 5 Baths, 2,007 SqFt Days Listed: 198
-42.76% ($1,195,100) 3 Price Changes : Last Change 2 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

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 nearly 4,000sf corner lot, consists of 2 structures and has just over 2,000sf of total living space. Located only a few blocks to Duval Street, the beaches, wonderful restaurants and many more of Key West attractions! Tenant occupied, minimum 24 Hour notice to show.

$1,600,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 2,671 SqFt Days Listed: 69
-11.11% ($200,000) 1 Price Change : Last Change 45 Days Ago
Multi-Units - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

TRIPLEX in Old Town Key West on large corner lot. Close to famous Duval Street. This historic Circa 1901 property offers almost 2700 sf ft of living space. Currently configured as three apartments but would make a grand conversion to a single-family home. Main floor offers two apartments, and the upper level has a spacious apartment with access to finished 3rd story attic space. Ideal location in the heart of Old Town near dining, shopping, and the Seaport. Unit 1: 1/1 could easily be used as a 2/1 1st floor apartment. Unit 2: 1/1 1st floor apartmentUnit 3: 2nd and 3rd floor 1/1 plus finished attic space which could be used as additional bedroom/ office space. (4 electric meters & 1 water meter) Off Street Parking! Basement Storage. Endless potential and prime location.

$1,600,000
Key West
Gg Watson Subdivision   - MM: 1.00
8 Bed, 8 Baths, 1,830 SqFt Days Listed: 158
-11.11% ($200,000) 3 Price Changes : Last Change 2 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

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 bathrooms$11,650 monthly rental incomeLocated in an X flood zoneThis property presents a unique opportunity to combine income-generating apartments with potential commercial space, all in a prime Old Town location. A investment opportunity in the heart of Key West.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 06-14-2025.
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