Florida Keys Commercial Real Estate for Sale in the Florida Keys

DEVELOPERS DREAM! 4 parcels on the water with 11 ROGOs, 240 of water frontage, 10,000 sq. ft. of bay bottom. The properties are located on both sides of Hilton Haven Road. Amazing opportunity, call for appointment, please do not disturb tenants. Listing agent must accompany parties.

Once-in-a-Lifetime Opportunity: Own the Iconic Alabama Jacks in Key Largo!Step into the legacy of one of the most celebrated waterfront establishments in the USA. This legendary bar and restaurant, continually rated among the Best Bars & Restaurants in South Florida, Florida, and the nation, is ready for its next chapter. Located on Card Sound Road at the foot of the Card Sound Bridge, Alabama Jacks has been a beloved destination since the 1950s, renowned for its authentic charm, lively atmosphere, and world-famous conch fritters.Key Features:Rich History: Established in 1947 and operated by the current owner since 1981, this landmark has maintained its iconic status and rustic charm, drawing locals, tourists, and celebrities alike.Turnkey Package: Sale includes the business name, domain names, Facebook page, a thriving retail t-shirt business, proprietary recipes, and all furniture, fixtures, and equipment (FF&E).Prime Waterfront Property: Two parcels totaling 41,602 square feet (.95 acres) with over 360 linear feet of boat docks, direct boating access, and a private boat ramp (currently unused, offering potential for new revenue streams).Buildings & Infrastructure: Includes 2,297 sq. ft. of finished space, 4,729 sq. ft. of canopy space, and an apartment for onsite living or staff use. Also features a desalination system and a backup water truck with a tank.Long-Term Lease: New & Secure, 20-year lease with the U.S. Government renewed in 2021 through 2041.Unparalleled LegacyAlabama Jacks is a true piece of Americana, beloved by generations and celebrated in publications and TV appearances by icons like Emeril Lagasse, Conde Nast, and Kathie Lee Gifford. Whether youre continuing its proud traditions or exploring new opportunities, this business is primed for success. Opportunity to Franchise the name and brand. Dont miss this chance to own a slice of Florida Keys history and elevate an already thriving landmark to its next level.

A rare and unique income producing Hotel in Marathon. Tropical Cottages is a boutique & profitable Mom and Pop Motel. Total of 11 valuable Transient Licenses, 13 Rooms plus office with kitchen & check in room. 9 buildings on the property, 8 adorable free standing cottages with new Victorian shingle roofs & the main building with 3 rooms in good condition. Each room has been tastefully and tropically renovated inside and out. Each room is unique & comes fully furnished. Most of the units have small kitchenettes including sink with microwave and refrigerator. All units have refrigerator & microwave. Additionally, there is a large Tiki Hut & Bar along with Food Truck with seating area. The Food Truck and Tiki Bar are leased for $6,000 per mos on a short term agreement. The Motel is managed by Owners . The hotel runs on auto-pilot. Online check-in available with a good housekeeping staff as back up. Most of the business is from repeat customers, plus online booking sites are all utilized.On site is a full laundry room with Commercial grade washers/dryers and storage rooms throughout. All housekeeping is done on site. Small, friendly & efficient staff has been there long term and willing to stay on with new owners. There are a total of 6 lots encompassing over 1/2 acre of land, total .56 Ac or 24,384 sf. Ample off street parking for guests. Zoning is GC and land use is recognized as Hotel/Motel. Bonus of Deeded waterfront access at the end of 61st St. which has a boat ramp and staging area for all types of watercrafts and sports. Same family ownership since 2010. Tropical Cottages was started back in the mid 1950s as a Fish camp and is one of the few remaining Mom & Pop Motels throughout the Florida Keys. Motel generates substantial Net income year after year to current owners. Sellers may consider Seller Financing to a qualified buyer and must have 40%-50% or more down payment. Terms to be negotiated.

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.

The Artist House is a well known established, successful guest house in the heart of old town Key West. It features 7 spacious transient guest room suites, a full kitchen, a beautiful reception room, a laundry, office and storage space. It has a special 5 COP historic hotel liquor license that creates an added value. Over the years, The Artist House has been featured in countless magazines, newspapers, television and media outlets as a favorite Key West destination and an important Key West landmark. The beautiful Queen Ann structure, with its trademark lavender shutters and towering turret is perfectly located between Simonton and Duval Street. Guests are often found relaxing on the charming front porch or having breakfast in the garden by the pool among the orchids or under the shade of the palm trees. Each of the seven spacious suites offer extra sitting areas to relax and enjoy the comforts of the inn. Within steps of Duval Street, the location is perfect for walking and biking. In addition to the vibrant guest house business, The Artist House well known for its rich history, the distinctive architecture, the picture-perfect curb appeal, the art of Eugene Otto and the legendary Robert the Doll. Whatever one loves most about The Artist House, eveyone agrees its a special place and beloved by tourists and locals alike. This is an opportunity to own this excellent business and an iconic Key West property.

7.7% Cap Rate at asking price! Prime income producing commercial property in the Heart of Islamorada! 100% tenant occupied with long term, TRUE NNN leases. 264 feet of frontage on Overseas Highway & 277 feet on the Old Hwy. Property offers 3 separate buildings. Building 1- Hardware store - retail use. Building 2- Boat Sales and service office with (2) 1 Bed / 1 Bathroom apartments on second floor. Building 3- Storage shed and workshop Total Gross Building Area: 9,124 Total Renovation and addition made in 2021, 2023. This property features ample parking with extensive open air boat storage.

Prime Trophy Investment Property in the heart of Duval St. The Coach Retail Building on the 500 block of Duval St. is a once in a lifetime opportunity! Property has been in the same family ownership since the 1940s. Tapestry aka Coach is a very strong, long term NNN retail tenant. Coach is preparing for a major and expensive upgrade and renovation to their store this summer 2025, all at their expense. Coach retail store occupies the entire ground floor with 51 of Duval St. frontage and a total of approx. 3,937 sf. Coach has been a great tenant in the building since 1998 and have a long term, NNN lease that was recently extended through January 31, 2033 with additional 3 year Option to extend until 2036.Upstairs are 6 professional offices and is completely rented. 2nd floor is 3,937 sf. with 6 individual offices. Upstairs tenants are on gross leases & each has own electric meter. Also a storage room & individual Men & Womans bathrooms. Combined all tenants provide consistent income with minimal owner management.Valuable large parking lot in rear is 518 Bahama St. Room for 10 + cars plus dumpster and loading area. Both lots total 9,068 sf. 2 story concrete Building is in excellent condition and well maintained.Extensive list of Building repairs and recent renovations available includ. new impact resistant doors and windows & awning replaced on entire first floor storefront, rebuilt rear stairwell, recoat roof, and stormwater disposal well in lot plus many others. Property sits in the 500 Block of Duval St. and sits on high ground in an X flood zone. Thousands of tourists and locals walk by & drive by daily. Neighboring business include Margaritaville, Banana Republic, Kilwins Fudge, Jack Flats, Gap, CVS & Walgreens, San Carlos Institute and more. Perfect investment for a1031 Exchange and/ or long term investor.

Seller is calling for offers...Attention Developers!!!....Direct oceanfront development opportunity located in the Economic Opportunity Zone in the Middle Keys. 1.67 acres with concrete seawall in place for (5) 30 dock spaces and (5) 30-40 T-Docks are in permitting. Development agreement in place with the City of Marathon for (10) single family villas with (10) building entitlements in hand to start building today. Villas are concrete construction, four bedroom, there and a half bathrooms, 2,643 sf under air, impact windows/doors, metal roofs, open porches, roof top deck, elevator, private pools and assigned docks. This property features a protected boat basin with six lots and four oceanfront point lots with direct open ocean views and access. This rare, oceanfront parcel would make a fabulous private multi-family compound or build (10) vacation rental income producing villas and take advantage of the tax benefits from the EOZ.

Once in a lifetime investment in the heart of Islamorada. This exceptional property offers a wide range of potential uses as it includes two Village Center parcels stretching from Highway to Bay, currently featuring a spacious 3,995 sqft restaurant and bar with a coveted 5COP liquor license - no food quota.Village Center zoning allows for multiple use opportunities including, but not limited to, single family estate, multi family compound, luxury townhomes, vacation rentals, restaurants, marinas, wedding venue, general store with package sales, and much more.The property spans 30,415 sqft. Includes a Bayfront boat basin, providing dockage for up to 7 vessels and there is adequate depth for an additional 100 dock to be constructed.The Village of Islamorada officially recognizes three waterfront market-rate dwelling units . The three waterfront Transferable Development Rights (TDRs) can be utilized onsite, transferred to another location, or sold to a receiver site. The Village Center Zoning would allow up to 8 market-rate dwelling units to be developed on site for a new luxury townhome community, with the transfer in of additional TDRs.Whether youre looking to rehab a local iconic business, start a new business, redevelop the entire site, or create a spectacular residential estate, this unicorn property is perfectly located. ***Buyer to verify ALL information.***

Prime Redevelopment Opportunity in the Heart of IslamoradaA rare investment in paradise! This one-of-a-kind property, made up of three parcels located at 82925, 82929, and 82935 Overseas Hwy, presents a developers dream in the heart of Islamorada. Offering a blank canvas, this unique site is poised for transformation, pending approval from the Village of Islamorada.Currently featuring a mix of mobile homes, multiple apartments, and a commercial building, the property is zoned Village Center, allowing for a broad range of redevelopment possibilities. Potential lies in creating a unique enclave complete with bungalows, amenities, and lush landscaping creating an aspirational residential community.At the gateway to Islamorada, this prime location offers an unparalleled welcome to all Islamorada has to offer including world-class fishing, dining, diving, and shopping. Pending Village approval, the property boasts 12 market rate dwelling units and 3,456 sq ft of non-res floor area. Investors may explore on-site redevelopment or transfer of building rights.Find a win through thoughtful investment in the charmed Islamorada real estate market.

Waterfront Trophy Investment Property & Marina located in the heart of Tavernier. Highly visible location with 250 ft. on Old Rd and Rt 1. Total of 4 parcels (Parcel ID #s-00436050, 00436680, 00436090, 004366700) with ample parking. The Landmark Restaurant waterfront building is 9,600 sq. ft. Over 713 ft. of seawall/dockage, and has approx. 22 deep water slips with direct access to the ocean. Includes 1,114 sqft single family 2 story CBS waterfront home. (103 Harbor Dr.)

Excellent development opportunities on this large Mixed Use commercial waterfront parcel with 200 feet of direct US Highway 1 frontage. 2.1 +/- upland acres and 1.47 acres of owned bay bottom in Bonefish Harbor with at least 5 controlling depth and access to the Atlantic Ocean. Property had over 550 feet of dockage directly to navigable channel. The propertys current use is a hotel/marina but the hotel business and accompanying Transient Rights (hotel unit rights) do not convey. Commercial square footage shall remain vested upon the property though. Seller has Development Plan for 33,400 Steel Building as a Boathouse with potential for 200 dry boat racks. Total number of dry racks could increase as City of Marathon building height ordinance has changed (increased) since plans were drawn. Dock plans allow for multiple configurations, including 30 wet slips with boat launch zone. Significant Seller Financing may be available to qualified purchasers with attractive terms and loan structures. Mixed Use is a commercial land use designation which allows for multiple development possibilities. Large commercial parcels with both US 1 and water frontage are not common and provide a considerable number of opportunities.

Exclusive opportunity to own one of the largest TRANSIENTLY licensed properties in Old Town Key West. 11 Br, 11Ba, 2 pools, 2 transient licenses, and off street parking for 4+ vehicles. The Watson House is Located centrally on Key Wests most iconic street and only 1 block off Duval street. The Grand Estate is comprised of a 7 Bedroom Mansion and a 4 bedroom Villa. Each home offering a private pool.The mansion was refitted by a local designer in July 2022, including fresh paint and new furniture. Upon entering the mansion you will be greeted with 12 foot soaring ceilings, 2 first floor guest rooms with bath, parlor, living room, dining room and kitchen. The kitchen opens up to a private pool with decking and lounge chairs. A large family style outdoor table is provided for dining al fresco. Heading back inside you will take the Victorian staircase to the second floor. On the second floor you will find 4 bedrooms with en suite baths. The front primary suite offers a private balcony overlooking Simonton Street. A secondary balcony is provided for the rear primary suite overlooking the pool. Take the spiral staircase to the third floor and you will discover a large third floor private suite. Bright and airy the suite provides a living room, wet bar and balcony overlooking the pool. All three floors can also be accessed by exterior and interior staircases. Going back into the parking area, you will take a side entrance to the villa. The villa was renovated to the studs in 2014 with modern and sleek finishes. The villa offers 4 bedrooms and 4 baths, full kitchen, living room, private pool and outdoor bar. The 2 transient licenses give versatility for the property to be rented as an 11 bedroom and 11 bath estate or rented separately as a 7br main house and 4br villa. There are few large estates in Key West, which gives way to its popularity and advance bookings.

500 K price reduction! A rare opportunity to own a private island with 50 acres and only minutes from Key West. So many possibilities. Build your own Equestrian Estate on over 5 acres of upland, The Southernmost stables with up to 12 horses. This property would be an excellent place to host large events like concerts, weddings, farm to table / wine tastings, or possibly therapeutic programs or retreats on a beautiful beach area. Easy to get to, as the island has access to the mainland via a 1/2 mile land bridge. The property is also located next to one of the largest mega yacht marinas and close to two upscale hotels. The owners used to run a small farm, bee keeping, music events, and kids summer camps on the island. One of the few places with untouched nature left in the Florida Keys. There are hives and bee boxes throughout the island - bees producing delicious mangrove honey. The property has 50 acres of mangrove forest, beach berms, hammocks, upland and trails .I think having land and not ruining it is the most beautiful art that anybody could ever want to own. - Andy Warhol

Beautiful adjoining oceanfront gated estates available individually or together. Each parcel has a single family residence with vacation rental income potential and are zoned Suburban Commercial for development opportunities..*UPDATE: There are 50 TDRs (TREs) available, preliminarily reviewed by Monroe County and transferable to these parcels for higher development potential! This unique wooded acreage has a deep basin and channel for ocean access, with dolphin piling boat slips and boat ramp. Single Family Residences with ROGO exemptions for remodel/rebuild possibilities. Highest approval rate via Monroe County is for MIXED-USE COMMERCIAL development. (The 6.1 acre parcel may be sold together with contiguous 3.2 acre parcel@95325 Overseas Hwy, AK#1592986,RE#00483360 000000 13 62 38 PT TR 5&6 SOUTHCLIFF ESTS PB2-45 & PT GOV LOT 1 & ADJ BAY for grand total of 9.36 acres, includes 1137 sf 1970 2/1 cbs home, metal roof.) *Includes data for both parcels and for taxes. This is a duplicate listing. Broker part owner/family owned.

Very Profitable Marina & Unique Resort in Islamorada, FL. 2024 NET Income reported over $1 Million/yr.!! Offered at over 10% Cap rate at Asking Price.Manager on site handles responsibilities with oversight from the absentee owner. Rare 1+ Acre Oceanside Lot with many uses possible. Deep water protected harbor with 18 large boat slips that can accommodate 50+ ft. yachts. Approach depth approximately 6 ft.+ at high tide with a clearly marked channel. Successful Boat Rental Business with 17 boats included in the sale. Lucrative Vacation Rental Business with (10) Aqua Lodges and 1 houseboat also included. Features include water, new 30 Amp and 50 Amp electric at each slip, fuel dock, concrete building with office, ship store, workshop, and garage/storage. 2 outdoor showers, 2 bath houses with indoor showers, stalls, and dressing area. New waste/pump-out station and fuel station. An additional separate concrete building used for storage on the North side of the property. Private marina, must call for an appointment and sign an NDA/CA for more information.

Located in picturesque Old Town of Key West, just steps from lively Duval Street, Douglas House is a captivating guest house ensemble. Spanning across five interconnected lots, with dual street access from both Amelia and Virginia Streets, this property is a remarkable collection of 15 licensed transient accommodations and a historic 5-COP liquor license + a parking lot. Douglas House, a cherished Inn, stands out for its perfect balance of accessibility and affordability, coupled with its recent renovations, ensuring it remains in pristine condition. At its heart lies a beautifully designed pool and bar area, enveloped by lush, tropical greenery, offering a tranquil oasis amidst the vibrancy of Key West. The guest house presents a variety of lodging options, from cozy queen rooms to expansive suites equipped with bars and kitchens, all featuring a modern decor. Many of these suites offer the added luxury of private porches or balconies, overlooking the garden and pool. Guests are treated to an array of amenities including a refreshing swimming pool, a charming bar area, off-street parking, and relaxing garden spaces with winding brick paths. Complimentary Wi-Fi and tea & coffee service add to the comfort of the stay. Moreover, the Douglas House is within a short stroll of Key Wests renowned attractions such as the Ernest Hemingway House, Southernmost Point Monument, and Sunset Pier at Mallory Square, not to mention the array of galleries, eateries, bars, and shops nearby. INCLUDED in the offering is a valuable parking lot at corner of Amelia St at 1108 Whitehead St., for added income.

Casa Manana Shores, located in the heart of Marathon, is a developers dream or a private owners potential paradise. This secured gulf front estate offers 3.86 acres of land and is surrounded by an eight foot concrete wall with three gated entrances. The property boasts approximately 540 linear feet of Highway frontage and 695 linear feet of water frontage. It offers 218 feet of concrete dockage, including a cut-in protected boat slip. There is even room for a helicopter landing pad. This unique property is zoned mixed-use commercial and comes with one commercial transferable building right. It is currently a private residence with a separate garage and workshop. The 10,852 square foot mansion is solid concrete construction with concrete pilings and copper pipes. It has ten bedrooms, six and a half bathrooms, and a sauna, game room and great room. Repairs are needed, and the interior needs substantial updating. An attached partially screened enclosure holds an impressive 12 ft deep swimming pool that measures 25 x 50 ft. The garage/workshop is a separate structure with two rooms with mini split air conditioning. The existing structures could be demolished for those with a vision, leaving you with a 3.86 acre blank canvas in the center of town. Its versatile designation offers multiple possibilities for residential and/or commercial use. Over the years it has previously housed a motel with a marina, a 19-unit trailer park, and a restaurant. This property lends itself to a variety of development or rehabilitation possibilites to create the vision of your dreams!

Heron House Court presents a unique chance to own a boutique guesthouse in the heart of Old Town Key West. This historic gem has been well maintained through the years & offers 15 deluxe rooms (14 licensed transient rentals).The relaxed atmosphere, with its private porches and multiple decked lounging areas throughout creates a wonderful ambiance.Steeped in history, Heron House Court circa 1900, was originally built to house the workers of Flaglers famous overseas Railway & is listed on the national register of historic places.Perfectly situated just a short stroll from Duval Streets world-class dining, shopping, and nightlife, as well as the Historic Seaport boardwalk, this island retreat attracts a steady stream of visitors year-round. The island-style setting, lush tropical gardens, expansive covered porches, and serene heated pool, create an unforgettable Key West experience.Sold fully furnished and turnkey, this well-established business includes all equipment, booking software, and a proven rental history, ensuring a smooth ownership transition. Heron House Court is a rare and wonderful opportunity to own in one of the most sought-after locations in Key West with unlimited potential.

The Paradise Inn, with its subtle luxury and Bahamian charm, is situated in the center ofOld Town Key West only a short walk or bicycle ride from the shops at Mallory Square, Duval Street, The Ernest Hemingway Home, and The Key West Butterfly Conservatory. The Hotel features an upscale amenity base including spacious gardens filled with exotic flora, a fountain-fed pool, jacuzzi, complimentary breakfast, daily wine & cheese happy hour, and 24-hour coffee. Ownership also owns a two-story building next to Paradise, on 817 Simonton Street, where there is a fully renovated 2BR/1BA apartment, with private balcony, and washer and dryer on the second floor. On the first floor thereis a commercial space that is currently leased out as a SPA. There are also six parking spaces at this Property.