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.

Located in Key Wests Casa Marina District on a quiet one-way street and just 2 blocks from the beach, 1304 Elizabeth Street presents a unique opportunity for those looking to take on a full-scale renovation project. This property is ready for a complete transformation and is perfect for developers, investors, or anyone eager to restore a historic Key West gem.Nestled in the desirable X flood zone and one of the most sought-after neighborhoods, the current layout includes two buildings with three separate units, all awaiting your vision to bring them back to life. The versatile HRO zoning offers flexibility for various investment goals, whether it is a full-time residence or a vacation retreat. Additionally, the neighboring property is also available for purchase, offering the option of an even larger compound. Schedule a viewing today and explore the possibilities to bring new life to this historic property and reimagine its potential..

Income producing, Turn-Key, Fully Renovated Duplex in Mid-Town. This property offers flexibility for use as a vacation home, primary residence, or investment opportunity with a HIGH ROI. This duplex is a proven income generator, with detailed financial records available. The property features two mirrored units, each comprising two bedrooms and one bath (4 bedrooms and two baths in total). Renovated extensively in 2019-2021, upgrades include hurricane impact windows, new AC units, a newer roof with solar-powered attic fans, and updated plumbing with PVC replacing all cast iron drain lines, installed in 2021. This meticulously updated duplex offers both modern comfort and strategic investment potential The duplex is also eligible for use as an Airbnb, as both units hold Key Wests required 28-day rental licenses with historic inquiries of at most $11K/month for peak months.

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. Shared parking can accommodate a small car. There is mature landscaping in the front adding to the privacy for the property. Each unit has their own washer/dryer. 1312 Catherine is located near White Street, conveniently located to many of Key Wests points of interest. The property is freshly painted, well maintained and move in ready.

Income producing opportunity close to Duval Street, Truman Waterfront Park, Hemingway Home and the Southernmost Point! If you are looking for a single family home or multi-family that is like no other, youve found it in this charming and eclectic, restored, Conch home The restoration brought out the best blend of history, island flavor, comfort and useful design. Move right in. Everything is up to current code with new impact-rated windows and doors, new metal roof, and re-built foundations. The 2 bedroom, 2 bath main house with extra rooms has new, wood flooring, closets in every bedroom, lofts for extra sleeping or storage and a large, eat-in kitchen with lots of cabinetry. The main house has a welcoming and covered front porch plus 2 more porches off either end of the kitchen. The detached 1 bedroom, 1 bath cottage in the rear of the property is also beautifully renovated and furnished and has 2 porches. It is a legal rental allowing minimum 28-day rental periods. The third building is an historic structure that was once a beloved neighborhood variety store. It has also been restored and includes a half bath and studio/creative space with a beautiful cedar ceiling. Theres an outdoor shower attached to this building.Drive right in to your off-street parking spot that will double as a patio for a party. Youll find rain barrels at the downspouts of the new gutter system. Theres a mature mango tree, an egg fruit tree, a papaya plant, a hog plum tree and several banana palms. An herb garden is located outside of the kitchen next to the barbecue patio. The landscaping evokes a beach feeling with rock and seashells, a hammock and of course tropical plants making it ideal for beautiful, garden gatherings.

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.

This unique property is a rare multi unit in the heart of historic Old Town Key West. The charming front area has a wide porch nestled behind tropical foliage on a quiet street. An outside staircase on the left leads up to a cozy space on the second floor, with a treetop view of a mango tree. A walkway on the right leads to the secluded rear space, with three doors opening to a wrap-around deck facing a beautiful, tree shaded garden, with room for a pool. The garden space offers a peaceful retreat, perfect for relaxation and outdoor gatherings. This property is in an elegant, tranquil neighborhood, a fifteen-minute walk (or five-minute bike ride) from the lively, restaurants, galleries, shops and vibrant attractions centered around Duval street, and Mallory Squares world-famous Sunset Celebration. This exceptional multi unit is ideal for a large family or an investor seeking multiple units. The property has been rented as is for many years with month-long or longer leases. For the buyer, there is a great opportunity to multiply the value (and potential revenues) of the property with judicious renovations. Property located in the X flood zone.

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.

Classic Conch Cottage Legal Duplex Needing Complete Renovation.Excellent Opportunity to Create Your Own Dream Property in the Heart of Key West. The Cottage Sits Well on the Lot with Room for a Private Pool. Very Good Existing Interior Square Footage to Work With. The Property Abuts The Louisa Street Park, a Very Green Space. Lots of Mature and Specimen Palms Towering in the Rear of the Property with Blue Skies Beyond. MLK Community Pool & Community Center are Adjacent.

Tucked away in the heart of historic Old Town Key West near Solares Hill, this enchanting property is a rare treasure that perfectly captures the charm and allure of Island Living. The front unit, a delightful two-bedroom, one-bath haven, features an inviting porch that exudes timeless Key West charm and affords the perfect perch to unwind amidst the vibrant tropical surroundings. Beyond, a beautifully updated, sunny studio in the rear offers a private, stylish retreat--ideal for guests or as a flexible space for your needs. Newly installed custom Murphy Bed, Full kitchen, Walk-in shower, Laundry and Built-in Storage. The sun-drenched rear deck is the ultimate spot to savor morning coffee or sunset cocktails, offering a picture-perfect setting for relaxation and entertaining guests.Framed by lush, swaying palms and vibrant foliage, this property is a serene, private oasis with the added convenience of a coveted off-street parking space for a compact car. X Flood Zone.Located in one of Key Wests most desirable neighborhoods, this home is steps away from the lively culture, iconic architecture, and world-renowned Duval Street music, dining and art scene. Stroll, and bike to all of your Key West favorites. With the unique ability to offset expenses by renting part of the property while still enjoying your own piece of paradise, this is an irresistible opportunity to create your dream island escape. Whether its a home away from home or a smart investment, this property is an exceptional find you wont want to let slip away! Location, location, location!

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!

Quaint Historic Duplex Located within Walking Distance of White St. Gallery District, Historic Old Town and Key West Beaches. Configured as a 2/1 on Ground Floor with separate living room and Kitchen. One Off Street Parking spot and room for a pool. Covered Outdoor living and spans the length of the property with lots of tropical foliage, brick walkways and plenty of room for a pool.Additional unit is a second Floor One bedroom Studio and the perfect remodeled Pied A Terre for your Key West Getaway. With an updated Kitchen and Bath, the living space has been thoughtfully designed to take advantage of all the space. Bedroom is to the Rear and Living Space opens out to a shaded Porch amid the Treetops where one can enjoy the tropical Ocean breezes from just a few blocks away. Property is completely private and surrounded by a Fence and Mature Tropical Landscaping.

Now priced to sell with this $50,000 price improvement! 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. Lease information available upon request. Competitively priced for just $1,440,000.

LEGAL DUPLEXImagine living in a house where you can enjoy your privacy in your own home while also having an investment on the side. The second house is tenant-occupied and already producing income, making it a perfect blend of comfort and financial benefit.Located in one of Key Wests most popular family neighborhoods.Discover the epitome of luxury living in this pristine property, featuring a two-bedroom, two-bath main home and a legal one-bedroom, one-bath accessory unit perfect for extra rental income. The main house is separated from the second house by a fence for added privacy. Every corner of this home showcases high-end finishes and meticulous attention to detail. The kitchen contains granite countertops, and top of the line appliances. The master en suite boasts glass doors that open to a stunning yard, complete with an outdoor shower and plenty of space for your dream pool. The beautifully landscaped yard offers a serene setting for both relaxation and entertaining.This home offers off-street parking, a spacious garage, and plenty of storage space, making it perfect for storing all your tools, toys, and more. Each unit enjoys its own electric meter, gas (guest unit), laundry facilities, and privacy. This home is packed with upgrades, including Grohe fixtures, solar panels, an on-demand water heater, a five-zone irrigation system, updated plumbing, and central air conditioning. Its truly move-in ready and located in a great area thats easy to see!

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!

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!

Welcome to 1409 4th Street - an exceptional 4-bedroom, 3-bathroom compound that is a LEGAL DUPLEX. The main home spans 2004 square feet with 2 bedrooms and 2 bathrooms, offering expansive living areas and a spacious kitchen with potential to add a third bedroom. Adjacent is a separate 2-bedroom, 1-bathroom home that would make for an ideal guest house or income producing rental.The homes sit on a large 10,000 sq. foot corner lot in the desirable and very convenient midtown area. Outdoor entertaining opportunities are limitless in the large, low maintenance yard that features a pool area just steps from the kitchen. Tucked away there is a tranquil garden with an avocado tree that provides a perfect hidden retreat.Dont miss out on owning one of Key Wests most versatile properties!

Price Reduced, Owners motivated! This triplex is situated in a prime area of Old Town, just three blocks away from Duval Street. It presents an attractive investment opportunity with its three separate units, offering potential for rental income, extended family stays, or versatile usage. Constructed from concrete blocks in 1979, this propertys main unit is currently occupied by the owners, who benefit from consistent rental earnings from the other two units, frequented by repeat monthly guests. Unit A comprises two bedrooms and one bath, spanning 768 sq. ft., while Units B and C are one-bedroom, one-bath units with 528 and 564 sq. ft. each. Each unit features its own laundry facilities and a private outdoor patio area perfect for relaxation. Additional conveniences include on-site parking and storage. The propertys strategic location, mere minutes from Duval Street, restaurants, bars, beaches, historical landmarks and waterfront attractions, enhances its appeal as a multi-unit investment. Take the opportunity to explore this property today and envision its myriad possibilities!

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!

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.