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Total Listings 26
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$2,999,999
Key West
Gwynn Subdivision   - MM: 1.00
3 Bed, 3 Baths, 6,268 SqFt Days Listed: 519
-19.98% ($749,001) 23 Price Changes : Last Change 8 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

A rare investment opportunity to own a residential mixed-use property located in the heart of Old Town Key West PLUS adjacent vacant lot. Property consists of 2 residential units upstairs (2BD/1BA + 1BD/1BA) & 4 commercial units downstairs, each with a 1/2 bath. All commercial tenants have long term leases in place. Renovated from 2016-2019 building features all hurricane rated impact doors & windows & is located in the X Flood Zone. White Street is the fastest growing corridor in Key West, acting as a border of Old Town & New Town Key West. Within a a short bike ride or walking distance to many of Key Wests popular restaurants, beaches, museums, hotels & B&Bs. This investment opportunity is not to be missed! Lots of possibilities - Live in one of the residential units and collect rent on the other 5 units, open your own business in one of the commercial units or rent out all 6 units! *Owner is a licensed Florida Realtor.

$3,199,000
Key West
Prog Land Imp Co Diag   - MM: 2.00
9 Bed, 9 Baths, 4,037 SqFt Days Listed: 114
-5.21% ($176,000) 1 Price Change : Last Change 24 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Ocean - Dockage: None

PRICED TO SELL. Discover Key West Quirk and versatility with this one-of-a-kind mid-century mansion/multi-family/cozy compound, i.e., whatever you decide to make of it. Whether you desire a primary residence with plenty of space for your guests, owner-tenant shared space, rental income, or a redevelopment opportunity with room to expand, the options are endless.Having previously received an award from Old Island Restoration of Key West, this home exhibits time period specific charm. The current owner has embraced the history of the house which was once home to a local artist and continued the appreciation of the propertys retro artistic flare. Upon entering your vibe will be transported back in time and every detail will tell a nostalgic story.The property comprises 3 units situated on an impressive nearly 12,000 square foot lot only 3 blocks from the beach. Each unit includes a separate entrance and private gated yard lined with tropical foliage. Additionally, there is a central courtyard that may be used as a common space. The main house consists of 4 bedrooms and 3.5 baths with a combo entertainment area that overlooks a massive green space and private luxurious heated pool. This allows the ultimate indoor-outdoor feel, and it is the ideal entertainment space for the bash of your choice. The lavish primary suite presents a grand garden view. The second unit offers 3 bedrooms, 2 baths and a tranquil outdoor shower. Exposed beams and skylights cast a pleasant hue on the living space.Lastly, the third unit encompasses 2 bedrooms and 2 baths with similar aesthetics and an expansive outdoor patio.With tons of storage space, youll have room for all your belongings and more. Enjoy the convenience of off-street parking and security of this concrete block home armored with impact windows and doors.Dont miss this rare chance to own a multi-functional piece of Key West history! Schedule a showing today to explore the limitless possibili

$3,750,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 3,665 SqFt Days Listed: 153
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

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.

$4,975,000
Key West
Benj Alburys Subdivisiond   - MM: 2.00
6 Bed, 6 Baths, 3,788 SqFt Days Listed: 155
Multi-Units - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

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!

$6,900,000
Key West
Old Town Unlisted   - MM: 1.00
8 Bed, 8 Baths, 5,343 SqFt Days Listed: 13
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

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.

$15,700,000
Key West
Webb Realty Co Subdivision   - MM: 1.00
57 Bed, 57 Baths, 25,393 SqFt Days Listed: 348
-5.56% ($925,000) 1 Price Change : Last Change 2 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

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.

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 11-26-2024.
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