This charming three-unit property at 808 Fleming Street represents an exceptional investment in one of Key Wests most desirable neighborhoods. Located in the historic Old Town district, this versatile building offers multiple revenue streams and tremendous potential for savvy investors.This property is ideal for investors or multi-family living. With separate electric and water meters for each unit, management is effortless and efficient.Property Features:Downstairs Unit: A spacious 984 sq. ft. living area, perfect for an owners residence or premium rental unit. Its open layout offers flexibility and comfort.Upstairs Units: Two additional units occupy 1,019 sq. ft. of living space, providing privacy, comfort, and excellent rental potential.Outdoor Living:Island living comes alive with this propertys inviting front porch and expansive front balcony, perfect for enjoying the tropical breezes. The private backyard includes a 22 x 18 wooden deck and an additional 22 x 23-yard area, offering endless possibilities for entertaining, relaxation, or further enhancements. An unused 11 x 6 cistern adds a touch of Key West history and utility to this unique property.Prime Location:Centrally located, this property provides easy access to Key Wests vibrant dining, shopping, and world-famous nightlife. Tenants and residents will enjoy the best of island life, with the perfect balance of convenience and tranquility in a sought-after neighborhood.Endless Potential:This multi-unit property offers endless possibilities--generate strong rental income, create a multi-generational living arrangement, or craft your dream Key West retreat. With its combination of private utilities, multiple spaces, and outdoor amenities, this property is ready to fulfill your vision.Call today

HUGE PRICE ADJUSTMENT - Now $2m. This is not a property to be missed! Prestigious Johnson Street LEGAL TRIPLEX, just four blocks from beach and the White Street Pier. Live your best lifein this wonderful neighborhood. Peaceful and quiet, it is only 3/4 mile to downtown Duval action. This property sits on an enormous corner (double) lot, walled in for privacy, it encompasses over 8600 square feet. Off-street parking for 5+ vehicles (no permit required), mature trees, lush grass and flowering shrubs abound. Two entry gates AND electronic gate for inside vehicle parking.This is a MONEY MAKER with a huge 1 bedroom home downstairs(space to create an additional bedroom), multiple living areas, Chefs kitchen with gas range, granite counters, SS appliances, breakfast bar, undercabinet lighting, soft close drawers. Enjoy views of the pool from every room. TWO 1-bedroom/1-bath apartments upstairs, approx 550-600 SF each. All units have been renovated and windows are impact rated. Each unit is separated for privacy and has their own access stairs and balcony plus grassy outside areas to enjoy. The crowning jewel of this property is the 16 x 32 foot heated, saltwater pool and spa with waterfalls. It is glorious and one of the largest Ive seen in town. An expansive side yard sits next to the pool offering plenty of room for outside play, pets and gatherings, perhaps even a pool house, outdoor kitchen & living! Come see for yourself why this home is so spectacular. It doesnt need a thing except you! Rent out all three units or rent out two and keep one for yourself! All of these units can be rented long term or by the month. We can close by year end if your client needs the tax benefit this year!

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 elses 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 Sanborn maps show an additional house on the property, that may be able to be rebuilt with permission from the city (buyers to verify). The home has plenty of the original Dade County pine waiting for restoration. Also featuring historic windows and double balconies. Currently the home is a legal duplex, each a 2 bedroom, 1 bath apartment. Buyers could retain the duplex or transform it into a stunning single family residence in the most sought after neighborhood in all of Key West.

Triplex in the X-zone with 6 bedrooms and 4 bathrooms total. Main house, 800 Elizabeth St., boasts 4 bedrooms and 3 baths; 624 Petronia St. is a duplex with two 1/1 units, each rented at $2,300 per mo. All units come with washer/dryer, and full kitchens. The main house is a two story with downstairs/upstairs balconies facing Elizabeth, with high ceilings, and a master bedroom that opens onto the upstairs balcony . A perfect location just two blocks from Duval Street, all units have been remodeled and updated. Priced at appraisal price from 2023, appraisal can be found in Documents.

Triplex investment property! Prime location only 1 block from the historic Key West seaport and 2 blocks from Duval St. The downstairs offers 2 units which include a 1/1 with kitchenette and a 1/1 with full kitchen. Enjoy the front porch facing Caroline St. or spend a lazy afternoon lounging by the dip pool in the backyard. Ascend the gorgeous wooden staircase to the upstairs unit which includes the 2nd and 3rd floors and has many features reminiscent of an old ship accented by beautifully detailed wood trim. This 2/3 unit includes hardwood floors, stained glass details, a loft/office, a front porch for relaxing, a small back porch overlooking the pool, and a unique widows walk where you can enjoy a bit of privacy in the treetops. The kitchen includes a built-in water filtration system, the master bedroom is a generous size, and youll find storage galore throughout the home with built-ins, nooks, and crannies. This historic home has high ceilings throughout, and the windows (except skylights) are hurricane rated. The owners currently live in the upstairs unit and use the first-floor units as monthly vacation rentals. Any of the units could be used as long-term rentals, or the property could potentially be converted into an up/down duplex or returned to its original configuration as a single-family home. Enjoy the close proximity to all the amenities this great location offers in Old Town. This historic gem is awaiting your vision.

Two Parcels Included!!! Welcome to 1320 6th Street, a fantastic investment opportunity in a prime midtown Key West location. This property features three private units, each offering great rental income potential. Your chance to make money and have a home in paradise.Enjoy the large inviting pool and well-maintained grounds, all just minutes from downtown Key West. Whether youre looking for a lucrative rental property or a versatile family compound, this unique property is a perfect choice. Dont miss your chance to own this gem in the heart of Key West! Prime Corner Lot enjoy the benefits of a corner lot with enhanced privacy and curb appeal.The property has ample parking and features a three-vehicle covered carport, along with additional off-street parking that can accommodate your boat or RV.The layout and landscaping provide a sense of seclusion, ensuring a comfortable living experience for tenants.This multi-family property is a rare find, combining practicality, privacy, and profitability. Dont miss out on this outstanding investment opportunity!

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.

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. Dont miss your chance to seize this investment gem in the heart of Old Town Key West. Schedule a viewing today and make your mark on the vibrant landscape of Key West real estate!

400 Aronovitz Lane is a contemporary island estate that redefines luxury and sophistication right in the heart of Old Town, Key West. Step through the grand entryway into a lounge that greets you with soaring 18 cathedral ceilings, a chic wet bar, elegant granite countertops, and top-notch amenities like a beverage cooler and ice maker. The open-concept living and dining areas are designed for seamless indoor-outdoor living, flowing effortlessly to multiple outdoor spaces. Imagine uninterrupted sight lines through expansive sliding glass doors, revealing a tropical poolside patio. This outdoor oasis features a Craig Reynolds-designed heated pool with a water feature, lush landscaping, ambient lighting, and a refreshing outdoor shower. The first-floor primary bedroom is a haven of relaxation, featuring a stunning en suite bathroom with luxurious marble finishes and an enclosed steam shower. The Chefs Kitchen boasts a large granite island, custom lighting, ample cabinetry, and high-end Sub-Zero and Thermador appliances. Upstairs, the second primary bedroom offers an en suite bathroom, wide plank hardwood floors, and sliding glass doors that open to a covered porch and outdoor shower. A cozy guest bedroom includes a beautiful bathroom with a soaking tub and access to a covered patio. Two additional downstairs guest suites, located just off the kitchen, each feature a sitting room, kitchen, washer/dryer, finished loft space, and a charming porch surrounded by lush landscaping for added privacy. This property is zoned for live-work (Historic Residential Office) and includes an ADA-compliant entrance. Located on a 5,891SF lot in the X-Flood Zone, and just a short walk or bike ride to the world-famous Duval Street, the islands finest restaurants and shopping, Truman Waterfront Park, and Fort Zachary Taylor Beach. 3+ off-street parking spaces! Dont miss out--schedule your private viewing today.

Ahoy, dreamers and visionaries! Step into the pages of Key West history with this captivating waterfront property, whispering tales of Old Town charm from its perch on the edge of paradise.Built before 1912, and lovingly held by the same family for over a century, this sprawling 15,609 square foot lot, zoned General Commercial, awaits your masterpiece. Picture a bustling restaurant serving up fresh seafood and island vibes, a charming boutique hotel nestled amidst tropical gardens, or a tranquil marina where sailboats sway in the gentle breeze. The possibilities are as endless as the ocean views.This unique property boasts a legal five-unit multi-family configuration, including a historic main house and a separate cottage. The main house features four units with a total of 5 bedrooms and 4 bathrooms, perfect for accommodating guests or creating a vibrant community. Meanwhile, the charming cottage, with its 2 bedrooms and 1 bathroom, offers a private oasis for rest and relaxation.Nestled beside Garrison Bight, a stones throw from Bayview Park and Tennis Courts, and just a bike ride away from some of the islands most stunning beaches and attractions, this location is a true Key West treasure.Now, for the fine print: the property is currently tenant-occupied, so please allow 48 hours notice for viewings (and you might not be able to see all units in one go). Savvy investors should verify restoration and development rights to unlock the full potential of this historic gem.Ready to set sail on a new adventure? This once-in-a-lifetime Key West investment is calling your name. Dont miss out on the chance to turn your dreams into reality!

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 heritage. Even the legendary Ernest Hemingway chose it as his base, staying here for a month while awaiting delivery of his car in 1928. Currently set up and legally recognized as 8 units, an atrium, garage, and a pool, this property provides an unmatched opportunity for someone who loves trophy properties. Whether you envision a grand single-family estate or multi-unit living combined with commercial space on the lower level, the possibilities are endless.Dont miss the chance to own a piece of Key Wests past while shaping its future with this truly one-of-a-kind property.

EMPLOYEE HOUSING! INVESTORS! DEVELOPERS! CONDO CONVERSION! 1005 Flagler Ave. boasts a courtyard, garage, storage unit and coin operated laundry building. This prime property is being offered with 7 other properties and 3 vacant lots as a single package, including (first # below after address is # of bedrooms/# of bathrooms):1009 Flagler Ave. 4/4-- 1621 Josephine St. 8/4-- 1719/21 Josephine St. 8/4--1723/25 Josephine St. 8/4-- 1819 Atlantic Blvd. 8/4--1714 Bertha St. 8/4--1716 Bertha St. 8/4-- 1821 Atlantic Blvd. vacant lot--1823 Atlantic Blvd. vacant lot--Bertha St. vacant lot adjacent to 1714 Bertha St. ALL FOR A TOTAL OF 32 UNITS--57 bedrooms, and 33 bathrooms, totaling 25,393 sq ft of Floor Living Area. With 65,482 TOTAL LAND SQ FOOTAGE, including the 3 vacant lots.Buyer to verify building rights for vacant lots.Property Data Cards from the Monroe County Property Appraiser are uploaded to Documents.