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$3,750,000
8 Beds ⋅ 8 Baths ⋅ 618438 MLS
Rare Multi-Family Investment Opportunity in Old Town Key West. This unique property is comprised of eight updated one-bedroom, one-bathroom units. 2 buildings situated on a 5,575 SqFt lot. It offers an exceptional opportunity for employers seeking staff housing, investors interested in a 1031 Exchange, or those considering a condo conversion. Please note that advanced notice is required to arrange showings, and not all units may be available for viewing as they are currently rented.

818 Elizabeth St, Key West
$3,100,000
3 Beds ⋅ 3 Baths ⋅ 617354 MLS
Welcome to 524 Southard Street, an extraordinary luxury offering in the heart of Old Town Key West that blends upscale finishes, commercial versatility, & superior sustainable construction just steps from Duval Street. This fully renovated mixed-use property features 2,262 sq. ft. of refined interior space designed with modern industrial style & historic Key West character. Inside, soaring 14' ceilings, expansive porcelain tile & luxury vinyl flooring, & thoughtfully curated lighting create an atmosphere of understated sophistication. The custom chef's kitchen is beautifully appointed with quartz countertops, premium appliances, a generous walk-in pantry, & sleek modern cabinetry. The flexible layout includes 3 bedrooms (1 used as a media room), 3 spa-inspired bathrooms, & a well-equipped laundry room. A separate office with its own off-street entry provides a true live/work advantage, delivering privacy & ease of access without entering the main residence. Outside, a private tropical oasis awaits with a heated and chilled pool, tranquil water feature, & lush landscaping, creating the perfect sanctuary for relaxation or entertaining. Zoned HCT (Historic Commercial Tourist), the property provides exceptional opportunities for luxury live/work use, rental investment, or commercial operation. It qualifies as a transient license receivership site & boasts a successful commercial history, adding value for those seeking income-producing potential in a prime location. Built with durability & efficiency in mind, the home includes impact-rated windows, doors, & skylights, a full fire sprinkler system, dual-zone cooling/heating, off-street parking for two, & a 25kW generator. Located in the desirable X-Flood zone and just moments from Key West's finest dining, galleries, and attractions, this property delivers an unmatched combination of luxury, quality, & opportunity in one of the island's most desirable neighborhoods.

524 Southard St, Key West
$5,500,000
6 Beds ⋅ 6 Baths ⋅ 618573 MLS
Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths of elegant living spaces, including a first-floor mother-in-law suite. Timeless design is found throughout with abundance of natural light and views of the lush, exotic landscape out every window. The great room features 12' ceilings, a curved wall of windows and French doors that lead to the serene, covered porch and outdoor dining space. The kitchen is a chef's dream equipped with new Viking appliances, ample counter space, and a view that overlooks the gorgeous, azure pool. The second level includes a spacious primary suite and two additional guest rooms, one of which has a balcony with treetop views and the island's best spot to view the spectacular 4th of July firework show. Two charming detached guest cottages tucked amongst the gardens offer secluded retreats each with full baths and one offering a living room and kitchenette. The outdoor oasis is defined by the oversized L-shaped pool and outdoor kitchen with built-in Viking grill; the perfect space for entertaining. This property is an exceptional, private sanctuary at an unbeatable location just one block from the crystal-clear Atlantic, tennis and pickleball courts, the esteemed Casa Marina Hotel and iconic White Street Pier. Don't miss the opportunity to call this remarkable estate your home! Seller is a licensed real estate broker and related to the listing agent. Seller is a licensed real estate broker and related to the listing agent.

906 Johnson 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
$2,999,999
2 Beds ⋅ 4 Baths ⋅ 616727 MLS
Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2/2 residential, office plus a detached restaurant. Seller financing is available to immediately start your investment opportunity! Call now for your private showing.

405 Petronia St, Key West
$5,950,000
6 Beds ⋅ 8 Baths ⋅ 617710 MLS
A gorgeous Old Town retreat offering exceptional space, privacy, and flexibility for family and guests. Ideally located within walking distance of the Historic Seaport, Fausto's grocery store, and Duval Street, this gated property features three distinct residences centered around a lush tropical courtyard and pool. The spacious rear residence offers 3 bedrooms and 3.5 baths with direct access to the pool, while the 2-bedroom, 2.5-bath residence above provides generous accommodations for visiting family and friends. Facing Eaton Street, the charming 1-bedroom, 1-bath historic cottage offers another private space for guests. Each residence is beautifully finished with luxury antiques, distinctive furnishings, and unique details that give every space its own character. With 3+ off-street parking spaces, multiple living areas, and an exceptional Old Town location, this is a rare Key West property designed for gathering family and friends while still giving everyone their own space.

723 Eaton St, Key West
$2,199,000
6 Beds ⋅ 5 Baths ⋅ 617882 MLS
This versatile 3-family property offers a rare blend of privacy & income potential. Designed as 3 distinct residences, each with a private entrance and it's own kitchen and w/d, the property is ideal for an owner-occupant seeking rental income or an investment for long term, vacation rentals or family compound. Main Level - Primary Residence: The spacious downstairs layout features a 2 bed, 2 bath, open-concept living area & updated kitchen w/ quartz countertops, wine cooler, & pantry overlooking the pool. The master suite has a built-in office, a custom walk-in closet system, & updated bath w/walk in shower. Main Level - Guest Suite is freshly painted w/private entrance, full kitchen, dedicated laundry, & full bathroom. Upper Level -3 beds & 2 baths, w/d, private entrance, French doors & balconies overlook the backyard foliage & pool. The 2nd remodeled bathroom services the 2 bedrooms, 1 of which is used as a media room. The open Living room/Kitchen has built-in wall shelves, The secluded backyard features a heated/chilled saltwater pool w/custom water feature by renowned master potter Jay Gogin. The grounds are secured by unique bamboo fencing and include a refreshing outdoor shower. Whole-house Generac generator and a large Rheem on-demand gas tankless water heater. Front of the house features an elevated patio overlooking the street. metal roof, accordion/panel storm shutters, & 2 driveways as well as 3 off-street parking . Need 24 hour notice to show!

1609 United St, Key West
$2,490,000
3 Beds ⋅ 8 Baths ⋅ 617030 MLS
**6%+ Cap Rate Opportunity ** Now offered at $2,490,000, this income producing Old Town property offers strong cash flow and immediate investor appeal. Located just steps from Duval Street, 402 Appelrouth Lane offers a rare investment opportunity in a premier X Flood Zone location. This mixed use property has income potential from residential and commercial units. With over 5000sqft of interior space this iconic structure showcases tall ceilings, historic architectural character and custom artistic details that give it Old Town Charm. Appelrouth Lane is known for strong foot traffic, established neighboring businesses and a desirable central location. just minutes from restaurants, galleries, shopping and Key West nightlife. Opportunities like this are exceptionally rare.

402 Appelrouth Ln, Key West
$4,300,000
4 Beds ⋅ 6 Baths ⋅ 617513 MLS
**31 photos have been virtually staged and enhanced to assist buyers in visualizing design and decor options for this home.** Casa Sapodilla introduces itself with the kind of presence that feels both storied and serene. Built in 1996 and set at 13' elevation on Solares Hill, the residence pays homage to the architectural romance of Old Town's most celebrated homes.. broad verandas, intricate trim work, and Brazilian Cherry hardwood floors that recall a bygone era of island craftsmanship. Inside, the home unfolds in layers of refinement. Sunlit rooms connect gracefully to the outdoors through French doors and deep porches. The main house's split-level design elevates the primary suite with its own private staircase, while two additional bedrooms ascend another, creating a sense of calm seclusion. A separate pool suite, complete with private entrance, extends the home's versatility. The kitchen is anchored by a suite of premier appliances.. including a new SubZero refrigerator and a refurbished Viking gas range, and framed by custom cabinetry and built-ins. Recent upgrades such as the 2025 metal roof, updated HVAC systems, and a 24 kW Generac whole-house generator reflect meticulous stewardship. Outside, the grounds rise to the level of a private resort. Tropical gardens wind around stone pathways, illuminated at night by soft landscape lighting. A heated saltwater lagoon-style pool, resurfaced in 2025, curves around natural rock formations, a spa, and three cascading waterfalls. Every vista offers a moment of stillness.. from the shaded verandas to the courtyard designed for open-air dining. A one-car air-conditioned garage, currently serving as an art studio, and a two-car driveway complete the thoughtful layout. Just blocks from Duval Street and the Key West Historic Seaport, Casa Sapodilla is both connected and deeply private.. a luxury retreat rooted in island elegance.. Inquire within for details on the low insurance costs available for this home

600 Elizabeth St, Key West
$2,859,000
3 Beds ⋅ 4 Baths ⋅ 616807 MLS
Built in 2008, this stunning 3-bedroom, 3.5-bath pool home perfectly blends the timeless character of classic Key West architecture with the comfort and convenience of modern construction. Ideally located just a short stroll from shops, restaurants, bars, and the world-famous Duval Street, this home offers the best of island living. Step inside to a bright, open-concept main living space with a wall of stackable impact glass doors that seamlessly connect the indoors with the private outdoor oasis. Just beyond the doors, you'll find a custom heated pool with tranquil water fountains, surrounded by lush tropical landscaping that offers both beauty and privacy, all complemented by a brand-new travertine pool deck that enhances the space with both elegance and durability. Each bedroom features its own en suite bath and walk-in closet, offering comfort and convenience for you and your guests. Storage is abundant throughout the home--a rare find in Key West. For added peace of mind, the property is outfitted with full impact-rated windows and doors. The modern kitchen is equipped with sleek stainless steel appliances, perfect for entertaining or everyday living. The home features two-zone central AC (one unit per floor), and the third-floor primary suite offers a loft-like retreat with both central air and a mini-split system for personalized comfort. Currently operating as a successful vacation rental, this property offers excellent income potential. The home can be sold turnkey with furnishings included, giving buyers the option to move right in or start generating rental income immediately.

814 Ashe St, Key West
$2,999,999
4 Baths ⋅ 616729 MLS
Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2/2 residential, office plus a detached restaurant. Seller financing is available to immediately start your investment opportunity! Call now for your private showing.

405 Petronia St, Key West
$2,649,000
4 Beds ⋅ 4 Baths ⋅ 610331 MLS
Introducing 3409 Eagle Avenue, a stunning new home, currently under construction in Key West, FL, designed for modern luxury and comfort. Current plans call for 4-bedrooms, 4-bathrooms but could be altered by a Buyer. Also, opportunity for buyer to customize high-end finishes to their personal taste. The entire lot was raised almost two feet and the home will be built above flood elevation, this energy-efficient ICF (Insulated Concrete Forms) home features a 1-car garage and a private pool, perfect for relaxation and entertaining. The spacious, open floor plan includes a gourmet kitchen and 3 primary suites, ensuring ample space and comfort for family and guests. Don't miss the chance to make this extraordinary home yours!

3409 Eagle Ave, Key West
$2,195,000
4 Beds ⋅ 4 Baths ⋅ 618256 MLS
This fully renovated canal front home at 1724 Bahama Drive offers modern waterfront living in a highly convenient location in Key West. The property features four bedrooms and four bathrooms and includes a separate mother in law unit, making it well suited for guests, extended family, or flexible use. The home has been completely updated with a new kitchen featuring quartz countertops, custom cabinetry, and stainless steel Thermador appliances. New tile flooring, updated lighting, and fully renovated bathrooms with clean modern finishes create a bright and comfortable interior throughout. The home also includes a new central air conditioning system and discreet security cameras that blend seamlessly into the design. A new roof adds peace of mind and makes this a true move in ready property. Outside, the home offers 56 feet of concrete seawall along a calm canal, providing excellent dockage potential and easy access for boating and paddleboarding. The outdoor space includes a bar and grilling area that is ideal for entertaining, along with a fully fenced yard finished with low maintenance turf for privacy and ease of care. The location is one of the home's strongest features. It is close to schools and the local high school and is within five minutes of grocery stores, restaurants, and beaches. Downtown Key West is approximately ten minutes away, offering quick access to Old Town, shopping, dining, and entertainment. This is a rare opportunity to own a fully renovated canal front home with flexible living space, boat ready frontage, and a central Key West location. One of the owners is a Licensed Florida Realtor.

1724 Bahama Dr, Key West
$4,450,000
4 Beds ⋅ 5 Baths ⋅ 616715 MLS
Experience the ideal blend of historic charm and modern luxury in this fully renovated and expanded Key West residence, where no detail has been overlooked. Set on a quiet, one-way street in Old Town, this 4-bedroom, 4.5-bath home offers 2,985 square feet of thoughtfully designed living space. Inside, soaring cathedral ceilings and rich Dade County pine walls create a warm, timeless aesthetic. Gorgeous hickory wood floors run throughout, complemented by two custom staircases and striking architectural features. The flexible layout includes a first-floor primary suite with a spa-style bath finished in marble and travertine, plus a second primary suite upstairs that also includes a private office—providing options for comfort, work, and privacy. All of the bathrooms are designed with a serene, spa-like feel, and every upstairs bath includes its own soaking tub for ultimate relaxation. The gourmet kitchen features Miele appliances along with a custom bar complete with a duel zone wine cooler and beverage center—ideal for effortless entertaining. Outdoors, an Ipe deck surrounds the heated and chilled saltwater pool with cascading waterfall features, all controlled by a smart automation system. At the top of the water wall, a decorative propane fire feature adds a dramatic focal point, while an outdoor shower completes your private tropical retreat. Additional features include two off-street parking spaces, impact-rated windows and doors throughout, metal shingle roof and dual-zone central A/C. With designer furnishings included and sold exactly as presented, this residence is ready to enjoy in the heart of Key West's most desirable locations.

1113 Stump Ln, Key West
$2,595,000
3 Beds ⋅ 3 Baths ⋅ 613986 MLS
Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

508 Grinnell St, Key West
$2,699,000
2 Baths ⋅ 617611 MLS
Real Estate offering only, business and liquor license not included. Prime corner location with great visibility on Truman Ave. HNC -1 Zoning allows many Commercial Uses including Transient Residential, Hotels, Multi Family Residential, Single Family Residential, Business & Professional Offices, Parking Lots, Medical Services, Food Trucks and more. Restaurants are a Conditional use. There are Two parcels of real estate, 1000 and 1006 Truman Ave. total of 104.75' on Truman Ave and 113' Deep. 2025 County Appraised Values of the two real estate parcels is over $2.7 Million! The existing corner CBS building is 2,396 sf. with indoor bar, men's and women's restrooms, office & storage, plus drive through liquor store. The existing drive through may be grandfathered for another potential use. The current Bar business may also be considered grandfathered. Several major repairs include new AC unit, new Bar, all new water lines and plumbing upgrades. New roof to the corner building in 2022. There is an additional 1,588 sf. of covered outdoor Bar with outdoor entertainment area. Same absentee owners since 1998 and first time listed for sale without the business or liquor license.

1000 Truman Ave, Key West
$2,395,000
3 Beds ⋅ 2 Baths ⋅ 618819 MLS
Introducing 319 Grinnell Street, a captivating residence in the heart of Key West's Historic Seaport, where charm and character abound. This beautifully framed Key West-style home reflects the rich tapestry of the area's history, showcasing classic architecture with inviting porches and intricate details that honor the past. Nestled among a collection of historic homes, 319 Grinnell Street offers a serene escape while remaining close to the vibrant pulse of the seaport. The Historic Seaport is a treasure trove of maritime heritage, featuring streets lined with art galleries, eclectic shops, and gourmet dining options. This lively district, once the center of the island's shipping trade, now celebrates Key West's legacy through its well-preserved structures and vibrant community life. Owning 319 Grinnell Street means immersing yourself in a lifestyle rich with culture and history. Enjoy leisurely strolls along the quaint streets, where the scent of jasmine and the sounds of laughter fill the air. This home is not just a residence; it's an invitation to embrace the unique spirit of Key West, making it a perfect sanctuary for those who value both tradition and modern living. Experience the allure of 319 Grinnell Street, where historic charm meets contemporary comfort in the heart of the enchanting Historic Seaport. Professional Vacation Rental Management is available for this property. Call for a showing today.

319 Grinnell St, Key West
$2,033,000
2 Beds ⋅ 1 Baths ⋅ 618183 MLS
Rare opportunity on desirable Aronovitz Lane in the heart of Key West! This unique offering includes two properties being sold together, creating exceptional flexibility for investors, builders, or lifestyle buyers. The package includes a vacant lot with the ability to rebuild its original two-unit footprint, a true rarity in Key West, presenting an exceptional chance to develop new construction in a prime setting. Paired with this is an existing 2-bedroom, 1-bath home, ideal for island living, income production, or incorporation into a larger architectural vision. Whether you're a builder seeking scarce development rights, an investor looking to maximize returns, or a buyer with a long-term Key West strategy, this is a once-in-a-market opportunity with limitless potential. Quietly tucked away yet steps from Key West's most celebrated dining, galleries, and waterfront experiences. This is Old Town Key West at its absolute best.

1 & 2 Aronovitz Ln, Key West
$3,375,000
2 Baths ⋅ 614149 MLS
Buy a Bar & Liquor Store in Key West! Dons' Place is the opportunity to purchase an Iconic and Landmark Indoor and Outdoor Bar & a Liquor Store with a Drive Through! This package is rarely available in Key West or anywhere in the Keys. Big bonus is that is includes a very valuable, full, unrestricted & transferrable 5-COP Liquor License that includes Tobacco & Retail Beverage with no food requirement! BEV 5400161. Monroe County Liquor Licenses are valued well over $1 Million and 2025 County Appraised Value of the two real estate parcels is over $2.7Million. Total Asset value alone is over $3.8 Million, not including business value. Two parcels of land total 11,836 sf. at corner of Truman & Grinnell Streets. The Indoor Bar and adjoining Liquor Store are in the main corner, CBS 2,396 sf. building along with men's and women's restrooms, office & storage. The building also operates maybe the only drive through, pick up window for Beer, Wine and Liquor left in the Keys! Several major repairs include new AC unit, new Bar, all new water lines and plumbing upgrades. New roof in 2022. There is an existing backup propane Generac Generator with automatic transfer not working. All Furniture, Fixtures and Equipment included. Outside is another 1,588 sf. covered outdoor Bar for entertaining, weddings, special events and parties. There is bar and table seating and a separate small office/storage building. The Bar and Liquor store are popular with both tourists and locals. The business is family managed with absentee owners and a few long time employees. Current Bar hours are 7am until 4am, 7 days per week. The Bar and Liquor Store are a money making operation with so many opportunities for growth for a new owner. Currently there is no food service on site, only pre-packaged snacks sold, but HNC -1 Zoning allows many commercial and residential uses & likely Food Trucks for added income. Same absentee owners since 1998 and first time listed for sale.

1000-1006 Truman Ave, Key West
$3,599,000
4 Beds ⋅ 5 Baths ⋅ 618829 MLS
1501 Georgia Street is a masterclass in design. Conceived by local architect Rob Delaune and set within lush, museum worthy grounds by renowned landscape architect Raymond Jungles, this striking 2,810sf residence sits on an expansive 8,800sf lot and captures the essence of tropical modernism. Clean lines. Soaring ceilings. Walls of glass. A seamless and intentional dialogue between indoors and out. This is true Mid Century Modern, authentically executed. A single story design with 4 bedrooms and 4.5 baths, wrapped in glass and stone, where skylights, pocket doors, and oversized windows flood the interiors with natural light. Every room frames the landscape, transforming the gardens into living artwork. Designed for both refined entertaining & comfortable family living, the home features stone floors throughout and a modern floor plan with garden views in every direction. Natural light fills the interiors, blurring the boundary between architecture and nature and creating a seamless indoor outdoor lifestyle that defines island living. At the heart of the home, a newly renovated showpiece kitchen elevates everyday life and gatherings alike, featuring dramatic Cambria quartz countertops with a waterfall island, warm wood cabinetry, pendant lighting, and stainless steel appliances. A full wall opens directly to the 55 foot heated and chilled saltwater pool and stone terrace, creating effortless flow for events large or intimate. The primary suite offers privacy and tranquil garden views, while all four bedrooms provide generous proportions and high ceilings. Oversized glass highlights the extraordinary tropical landscaping surrounding the home. The grounds showcase native and exotic flora from around the world, tropical atriums, a water garden with koi, multiple water features, an outdoor shower, and exceptional privacy inside & out. Properties of this caliber and architectural significance rarely become available, so don't wait, schedule your private showing today!

1501 Georgia St, Key West
$3,750,000
7 Beds ⋅ 8 Baths ⋅ 618468 MLS
Charming Single family home with multiple guest cottages in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

919-921 Thomas St, Key West
$3,750,000
7 Beds ⋅ 8 Baths ⋅ 617140 MLS
Charming Multifamily Compound in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional multifamily compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

919-921 Thomas St, Key West
$4,695,000
4 Beds ⋅ 5 Baths ⋅ 618470 MLS
Step into the enchanting world of Key West history at 709 Eaton Street, a meticulously preserved gem built circa 1847 in the iconic Seaport neighborhood. Historic charm and modern comfort, this home delivers 4 bedrooms, 4.5 baths, with 3 bedrooms, 3.5 baths conveniently located on the first level. The upstairs consists of the primary bedroom suite with an additional private study as well as a wonderful, covered porch. Discover the timeless elegance of its living room, dining room, and a fantastic den with an open kitchen floorplan complete with Viking appliances. Step outside to enjoy your covered patio, private pool, and inviting outdoor living areas surrounded by lush tropical foliage on the oversized 6,150 SF lot. Driveway for two cars with one covered parking space. Perfectly situated for exploring Key West's vibrant attractions, this home offers a rare opportunity to own a piece of island history while indulging in the ultimate Key West luxury lifestyle.

709 Eaton St, Key West
$2,500,000
1 Beds ⋅ 3 Baths ⋅ 615015 MLS
Completely remodeled from top to bottom, this turnkey restaurant in the heart of Old Town Key West offers a rare opportunity to own a fully updated and licensed 150-seat dining destination. Every inch of the property has been thoughtfully renovated, including brand-new electrical, plumbing, HVAC, flooring, lighting, and fixtures, creating a fresh, modern space that still captures the charm and character of historic Key West. The layout features expansive indoor-outdoor dining areas, a stylish full-service bar, and newly designed restrooms, all tailored for comfort, ambiance, and efficient flow. The commercial-grade kitchen is fully equipped with state-of-the-art appliances, ample prep space, and storage, making it ideal for high-volume service across a wide range of culinary concepts. Adding to its versatility, the property also includes a beautifully updated 1-bedroom, 1-bathroom apartment upstairs—perfect for on-site living, staff housing, or additional rental income.

532 Margaret St, Key West
$2,000,000
8 Beds ⋅ 4 Baths ⋅ 610098 MLS
Development Opportunity. (4) townhouse unit complex situated on a heavily landscaped 10,000 sq ft parcel. Comprised of (2) side by side duplexes legally subdivided as ( 4 ) individual, 750 sq ft licensed units, with (4) separate legal descriptions, parcel numbers, insurance policies, & utilities meters. At one time, there were four individual loans on each of the units as well. **** The only common area is the roof over each duplex, the shared wall between the units and walkways between, and on either side of each of the (2) duplexes. **** Each unit has its own laundry room addition directly off the kitchens with separate exterior screen doors - - (4) pairs of new washers & dryers. Current below market rents for each 2 bedroom, 1 bathroom unit runs between $2,225 to $2,900 with the lower rents soon to be increased. ***** Always operated as a successful rental property, the units were never sold off, which is definitely the Highest and Best use of the complex. Added value would be to install a lap pool/ patio area in the 100' wide back yard as a common use amenity. 2nd option - would be to provide a private pool area for each of the rear (2) units, giving each one half of the large rear yard, greatly increasing their sale value. Mature landscaping that has been well maintained surrounds the property and separates the units. Other valuable amenities are the over sized covered front porches with high open beamed ceilings offering additional square footage - and - valuable on site parking for 10 cars. The property has been continually well maintained - painted, new air conditioners, blinds & curtain rods on all windows. All roof screws were replaced & new ones added to code standards. ***** Under ''Documents Tab'', see the survey with legal descriptions for each unit, floor & site plan & aerial photo. (4) Windstorm, Flood, Fire & Liability policies in place. Call for additional information. Realtor owned.

2322-2324 Seidenberg Ave, Key West
$4,699,000
10 Beds ⋅ 10 Baths ⋅ 616601 MLS
Rare Multi-Family Investment Opportunity in Old Town Key West. This unique property is comprised of nine units, including eight updated one-bedroom, one-bathroom units and one two-bedroom, one-bathroom unit. 3 buildings situated on a 8,042 SqFt lot. It offers an exceptional opportunity for employers seeking staff housing, investors interested in a 1031 Exchange, or those considering a condo conversion. Please note that advanced notice is required to arrange showings, and not all units may be available for viewing as they are currently rented.

818 Elizabeth St, Key West