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$3,300,000
3 Beds ⋅ 2 Baths ⋅ 621273 MLS
Old Town charm in the heart of Key West! This two-story Conch-style residence offers an exceptional opportunity to enjoy island living in the highly desirable Old Town Historic District. A two-car driveway provides convenient off-street parking, while a welcoming front porch leads into an inviting interior with wood floors throughout the first level. The well-appointed kitchen features a gas range, stainless steel appliances, and easy access to the outdoor entertaining areas. A comfortable sitting room provides the perfect space to relax after a day enjoying Key West. The entire second floor is dedicated to a spacious primary suite featuring a large walk-in closet, mini-split A/C, private bath with shower, and a sunbathing area. An additional flexible space is ideal for a home office, reading area, or extra living space. Outdoor living is a highlight, with a covered patio featuring exterior lighting and ceiling fans, plus a jacuzzi and outdoor shower for year-round enjoyment. Additional conveniences include a dedicated laundry room with full-size washer and dryer, utility sink, workspace, attic storage, and a detached storage shed. Storm-ready features include a metal roof and exterior hurricane shutters, while interior plantation shutters add classic Key West character. Ideally located just a short bike ride from Duval Street, Mallory Square, St. Mary's, restaurants, galleries, shops, entertainment, and the waterfront. A wonderful opportunity to own a distinctive Old Town residence combining historic charm, valuable off-street parking, inviting outdoor spaces, and an exceptional Key West location.

728 Poor House Ln, Key West
$575,000
2 Beds ⋅ 1 Baths ⋅ 620957 MLS
Charming Key West living in a fantastic central location! This inviting end-unit condo offers an easy, low-maintenance opportunity to own a piece of the island, whether you're looking for a full-time residence, Key West getaway, or investment property. The bright interior features tile floors, granite countertops, central A/C and a functional kitchen, while the fenced outdoor space adds a rare touch of private outdoor living. Surrounded by tropical landscaping and just a short bike ride from Old Town, beaches, restaurants, shopping and everything Key West has to offer. A great opportunity to enjoy the Key West lifestyle or add an island property to your investment portfolio.

1332 Seminary St Unit 103, Key West
$450,000
2 Beds ⋅ 2 Baths ⋅ 620647 MLS
2 BEDROOMS 2 BATHROOMS WITH BALCONY, GATED COMMUNITY, HUGE POOL, TENNIS COURT ,PLENTY OF PARKING AND WALKING DISTANCE OF SHOPPING, GROCERIES, RESTAURANTS AND MOVIE THEATRE.

3312 N Northside Dr Unit 607, Key West
$1,139,000
3 Beds ⋅ 2 Baths ⋅ 620641 MLS
Tucked into the leafy heart of Midtown, just a quick bike ride from Smathers Beach, Higgs Beach and the energy of downtown, 1708 South St. offers something increasingly rare in Key West: a property with nothing to do but move in and enjoy. With its classic stone facade, this 1952 residence captures the distinctive architectural style that defined post-war Key West, delivering 1,445 sq. ft. of low-maintenance living, ideal for the second-home buyer who wants the Key West lifestyle without the upkeep of a larger historic home. Tile floors run throughout, complementing a solid wood kitchen that retains its excellent-condition granite countertops. A versatile Florida room to the rear opens through French doors to the back garden, equally suited as a formal dining room, a home office, or a playroom. Beyond, the backyard is a blank canvas, ready to become a stunning tropical Key West oasis complete with an outdoor entertaining area. The detached guest cottage, with its own private entrance, adds a third bedroom to the property and is currently leased to a long-term tenant (Lease expires Sept 30th 2026) at a meaningful monthly rent, offering established income with true separation of space, a compelling proposition for the second-homeowner who wants their property earning for them even when they're not there to enjoy it. A covered carport for two vehicles and abundant storage round out the property's everyday practicality. Offered at a clear value against comparable Midtown properties, this is an entry point into island living that is as flexible as it is rare. Welcome to Key West Living at its finest.

1708 South Street, Key West
$3,500,000
5 Beds ⋅ 5 Baths ⋅ 620434 MLS
First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

416 Fleming St, Key West
$895,000
4 Beds ⋅ 2 Baths ⋅ 620315 MLS
This large home on an extra large 6300 sf corner lot is an excellent opportunity for a renovation project. The main home is just under 1600 sf and consists of 4 bedrooms and 2 bathrooms and there is also a good sized detached structure of almost 200 sf that could be turned in to, among other ideas, an extra bedroom, artist's studio or pool cabana. The home had the roof replaced in 2014 and has storm shutters. There are terrazzo floors. The extra large lot has sour orange, Spanish lime and banana trees, off street parking and plenty of room for a pool.

3746 Paula Ave, Key West
$4,550
1 Baths ⋅ 620194 MLS
Prime retail leasing opportunity in the heart of Old Town Key West, just one block from Duval Street. This 805 SF storefront on Simonton Street benefits from exceptional visibility and strong year-round foot traffic from both locals and visitors. Surrounded by restaurants, boutiques, galleries, and lodging accommodations, the space is ideally positioned for a variety of retail, gallery, office, or service-oriented uses. Rare opportunity to secure a presence in one of Key West's most sought-after commercial locations. Base rent only; NNN expenses not included.

601 Fleming St Unit B, Key West
$5,300
619760 MLS
326sf in Strip Center on Front Street across from Mallory Square, located on the busiest corner in Key West. Outstanding foot traffic from tourists, cruise ship passengers, sunset celebrations and locals. Join Haagen Dazs, Seabags & Green House. In addition to monthly base rent quoted are triple net charges and sales tax.

431 Front St Unit #5, Key West
$850,000
2 Baths ⋅ 619620 MLS
FOR SALE: Mellow Ventures LLC - Premier Eco-Tour & Luxury Houseboat Rental Company in the Florida Keys Step into one of the most unique lifestyle and income-producing businesses in the Florida Keys. Mellow Ventures LLC is a turnkey, multi-stream eco-tour and hospitality operation with a proven track record, established brand presence, and rare waterfront assets perfectly positioned for continued growth. Operating out of Key West, this boutique adventure company has built a reputation for intimate, sustainable experiences on the water—guided eco tours, private charters, island excursions, and custom adventures designed to showcase the natural beauty of the Lower Keys. In addition to its successful charter business, the sale includes two custom-built luxury houseboats, currently operating as high-demand short-term rentals. These floating suites offer a one-of-a-kind Airbnb experience that consistently generates strong occupancy and premium nightly rates. Each vessel blends modern comfort with an immersive waterfront setting, providing an unforgettable stay for guests seeking something truly special. Highlights Include: -Well-established eco-tour & charter business with brand recognition in Key West -24' Twin Vee -Two fully custom houseboats designed for nightly rentals -Strong Airbnb track record with exceptional occupancy -Multiple revenue streams: eco tours, private charters, overnight rentals -Turnkey operation with booking systems, media assets, furnishings & equipment -Excellent online reviews and repeat clientele -Ideal opportunity for owner-operator or investor seeking passive/managed income -Rare waterfront lifestyle business in a world-renowned destination This is a unique chance to acquire a thriving, experiential Keys business blending adventure tourism with boutique hospitality—a lifestyle investment that generates real returns.

Rat, Key West
$999,000
6 Beds ⋅ 2 Baths ⋅ 619618 MLS
Duplex with Solid Income - $91,800/Year This income-producing duplex offers two spacious units, each featuring 3 bedrooms and 1 bathroom--an ideal setup for steady, long-term rental demand. Currently leased at $3,850 and $3,800 per month, the property delivers a strong annual income of $91,800. Situated on a 4,400 sq. ft. lot in a desirable location near the coast, this property is just a short ride from the energy of downtown, making it highly attractive to tenants who want both convenience and lifestyle. Each unit is separately configured, providing flexibility for investors or owner-occupants. The rear unit benefits from off-street parking--a valuable feature in this market. Built with durable Indian Block construction, the property offers long-term structural integrity with room for future value-add opportunities.

1916 Seidenberg Ave, Key West
$150,000
2 Baths ⋅ 619435 MLS
Turnkey boat charter and Airbnb business in Key West featuring a 42' Maxum cabin cruiser set up for short-term rental use, plus a 17' Angler (2023 Suzuki 140HP) and 22' Hurricane (Yamaha 150HP) for charter operations. Includes transferable wet slips, an active Airbnb Superhost listing with strong reviews, and all necessary permits, staff, and infrastructure for a seamless transition. Proven income-producing opportunity in a supply-constrained market.

1 Boat Rental Business, Key West
$90,000
619380 MLS
S.T.S. Food Truck (Sliders, Tacos & Sammies) is ready to roll and start serving. This is a 2014 Dodge Ram 2500 ProMaster food van with only 50,000 miles. This is a true turnkey-style setup for operators who want a clean, capable build-out and the flexibility only a van can offer--drive in, serve, and roll out with ease for private events, weddings, catering, and high-traffic venues. Included equipment: A/C, Awning, (2) propane tanks, generator, refrigerator, prep station coolers, stovetop, flat-grill, BBQ smoker, food warmer, steam table, exhaust hood & fan, worktable, hot water heater, hand-wash sink, triple sink, fresh & gray water tanks, fire extinguishers, and a professional fire suppression system. Everything is up to code. Operating history includes major success at farmers markets from Key West to Sugarloaf to Big Pine, plus concerts and special catering events. Sale includes food van and all tangible equipment only. Licenses and permits are non-transferable; however, are easily obtained and at a reasonable cost. No outstanding debts. Seller is exiting due to time constraints. Equipment may be removed if you want a custom reconfiguration.

Duval St Unit Food Truck, Key West
$55,000
619358 MLS
Well-established, profitable landscape maintenance business available in Key West with immediate returns. The business provides routine landscape maintenance to 14 loyal accounts in prestigious Key West neighborhoods. Potential for growth with installations as well as continued return with ongoing maintenance. Service provided can easily be completed with a 2-man crew in 32-34 hours each week. Sale includes all essentials needed for continued success: Stihl battery powered maintenance equipment and additional lawn maintenance tools. Detailed financial information available with a signed Confidentiality Agreement. BUSINESS ONLY. No Real Estate.

1 Landscape Maintenance Co, Key West
$1,249,000
619200 MLS
425 Bahama Street presents an exceptional opportunity to own a revenue-generating parking lot in iconic Key West, Florida. This income-producing property offers existing cash flow and represents a rare investment in a high-demand location where parking remains a valuable and limited commodity. Whether held as a steady income asset or positioned for future upside, this property offers investors a unique combination of immediate revenue and long-term potential in one of the most sought-after markets in the Florida Keys. Buyer to verify all details, including income, zoning, and allowable uses.

425 Bahama St, Key West
$75,000
1 Baths ⋅ 619166 MLS
The Blue Cat & Red Dog Too! For over 30 years the Blue Cat has served the Key West fur community. Boasting loyal customers worldwide, the Blue Cat features must have Key West themed items for our furry kids: catnip cigars, catnip sushi, bathrobes, raincoats, doggles, Hawaiian shirts, motorcycle jackets and doggie t-shirts, etc. Also available is a variety of Key West themed doggie toys and treats such as lobsters, shrimps, sharks, beachballs, flip flops, squeaky beer bottles and soda cans. For humans there are shirts and nightshirts, purses, kitchen items and household goods all with a purrfect attitude. The Blue Cat is located in the historic Old Town section of Key West just off Mallory Square. It is easily accessible to foot traffic, cruise ship passengers and the sunset festivities. The Shops at Mallory Square are airconditioned and have public restrooms. The lease is affordable and renewable as the rent includes CAM charges such as restrooms and air conditioning, and all common area maintenance. Offering price includes inventory, all fixtures, shelving, cabinets, displays and cash register. Business has over 30 established vendor accounts and well thought out inventory items. This is a fun business for a fun person!

291 S Front St Unit 104, Key West
$1,300,000
7 Beds ⋅ 5 Baths ⋅ 618731 MLS
Builder/Contractors Dream ! Rare 4 unit new development opportunity, 7,000 square ft lot available in Midtown Key West.

2016 Roosevelt Dr, Key West
$6,850,000
3 Beds ⋅ 3 Baths ⋅ 617136 MLS
103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. This home is perfect for entertaining on a large scale or enjoying a quiet evening. A dramatic staircase leads to a second floor walkway which is open to the main level. The floor plan provides privacy for each bedroom with the primary suite at one end of the hallway and a guest bedroom suite at the other end. Another guest bedroom and bath are on the first floor creating an option for a first floor primary bedroom. Custom features throughout are evidence of the artistic ingenuity used in the design of this impressive home. The kitchen features custom wood cabinets and granite countertops and is open to the dining area. Tall windows and french doors flood the home with sunlight. This home is perfect for indoor/outdoor entertaining. A wet bar features custom built ins plus an icemaker and refrigerator. Fronted by a white picket fence, the home sits back from the street and is adorned by tropical foliage. This unique structure with thick brick walls and impressivly tall windows offers passers by a glimpse of the historic origins of the Truman Annex. Its location in the heart of old town Key West provides easy walkability to the waterfront promenade, Ft. Taylor beach, cultural venues, shops and restaurants. The property comprises two lots with a large swimming pool and spa plus an outdoor shower between the covered and open air loggia and parking. There's plenty of space for entertaining outdoors under the palm trees. This estate home is one of a kind was restored to the highest standards. One must see this home to appreciate the incredible design and attention to detail that went into this historic treasure.

103 Front St, Key West
$5,600,000
3 Baths ⋅ 617330 MLS
Prime Commercial Property in Iconic Key West - High Visibility & Versatility! This property offers a rare opportunity to own a substantial commercial footprint in one of Florida's most iconic destinations. Whether you're expanding a brand, launching a new concept, or investing in Key West's vibrant market, 3424 N Roosevelt Blvd is a strategic asset with flexible potential. Location Highlights include: • Strategic Location - Located on Key West's main commercial corridor • Proximity - 7 minutes (2.5 miles) to Key West International Airport • Exceptional Visibility - High traffic exposure from both locals and tourists • Surrounded by Amenities -Including hotels, restaurants, banks, shops, fitness centers, and grocery stores. Property Details • Building Square Footage: 3,420 sq ft • Building w/ Tiki: 7,491 sq ft • Lot Square Footage: 36,002 sq ft • Frontage: 155 feet Current Use • Vehicle - Rentals Currently operates as a successful vehicle rental business. • Service Department - Features a care center with six service bays. Business Opportunity sold separately, inquire with agent.

3424 N Roosevelt Blvd, Key West
$25,000
617315 MLS
A rare opportunity to purchase one a transferable City of Key West Vendor's License. These licenses are limited in availability and allow the holder to engage in vendor operations as permitted under City of Key West regulations. Vendor licenses are not often available, making this an excellent opportunity for qualified buyers seeking to establish or expand a business within the city.

1 Vendors License, Key West
$150,000
616922 MLS
Mundy the Pirate is a unique seafood source in the Florida Keys, 45 years in business. Mundy the Pirate Mobile Restaurant does local seafood delivery in Key West and Stock Island. Whole Conch, Jumbo Scallops, Hog Fish, Grouper, Mahi Grunts, Lobster, Stone Crab, Deep Water American Red Shrimp, Key West Pink Shrimp, Rock Shrimp, Conch Ceviche, Fish Ceviche, Pink Shrimp Ceviche, Smoked Fish, Smoke Fish Dip and more.. Mundy the Pirate Seafood also ships seafood! The mobile establishment features a menu filled with fresh seafood, including local catches, and offers a variety of dishes that reflect the flavors of the Florida Keys. Additionally, the mobility allows easy access to many special events, enhancing the lively ambiance typical of Keys outdoor dining. The pirate theme adds a fun, whimsical touch to the dining experience, making it popular among both tourists and locals. This thriving Business is being offered with all the licenses, 2018 truck, enclosed trailer with flat grill, deep fryers, fish boxes, equipment. Owner will consider training new owner and introduction to local seafood vendors. This rare turnkey operation in paradise can be yours.

1 Mundy The Pirate Seafood Way Unit No Real Estate, Key West