Key West FL Historical Real Estate, Homes for Sale

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

$1,995,000

3 Baths ⋅ 616452 MLS

Introducing a prime investment opportunity at 718-720 Caroline Street, Key West, FL now offered at a 6.7% cap rate. This historic property boasts a 3,424 SF building with three commercial units, offering versatile retail or street retail spaces for savvy investors. Built in 1918 this meticulously-maintained property captures the essence of Key West's rich architectural heritage. With a current 100% occupancy rate, it presents a lucrative prospect for investors seeking a flourishing market with a strong tenant base. Don't miss the chance to own a piece of Key West's history and secure a profitable venture in this sought-after commercial district. Businesses not for sale, please do no disturb the businesses.

718 720 Caroline St, Key West

$1,499,000

3 Beds ⋅ 3 Baths ⋅ 617589 MLS

POOL & POOL HOUSE COMPLETED! Opportunity awaits to create your perfect midtown home. This property consists of a partially updated main home totaling 1233 sq ft with 2bd/2ba and a bonus room. A newly constructed elevated 256 sq ft guesthouse with a kitchenette and bathroom. Professional landscaping, pavers and low maintenance artificial grass lead to the brand new heated pool. Irrigation and landscape lighting installed. Main house needs some renovations throughout but has been partially updated and is perfectly livable. Must see!!

1505 Johnson St, Key West

$1,265,000

3 Beds ⋅ 3 Baths ⋅ 616195 MLS

Welcome to 1718 United Street, a beautifully renovated home in the heart of Key West offering modern comfort with timeless island charm. This spacious residence features 3 bedrooms and 2.5 bathrooms, including a stunning spa-style master bath with double sinks and dual shower heads for the ultimate retreat. The bright and open layout showcases elegant marble countertops, thoughtfully designed finishes, and inviting living spaces perfect for both relaxing and entertaining. Step outside to enjoy the side porch facing the driveway, an ideal spot for morning coffee or evening gatherings. A standing seam metal roof adds both style and durability, giving peace of mind for years to come. To enhance the island lifestyle even further, the seller has drawings available to the buyer for a pool and tiki hut, offering the opportunity to create your own backyard oasis. Ideally located just a short bike ride to the vibrant energy of downtown Key West and world-famous Duval Street, this property combines convenience, comfort, and style—move-in ready and waiting to be enjoyed as your new island home.

1718 United St, Key West

$1,089,000

4 Beds ⋅ 2 Baths ⋅ 616139 MLS

Welcome to 2809 Flagler Ave, a beautifully updated residence that seamlessly blends classic charm with modern convenience. Originally built in 1953, this home has been enhanced with a thoughtfully designed two stories new addition in 2002 increasing both its space and functionality. The interior of the home is adorned with stunning 3/4 inch red oak flooring, providing a durable and elegant finish throughout. One of the standout features is the spacious office, perfect for remote work or study, which can also double as an additional bedroom if needed and a designated laundry room. Every room/bedroom is equipped with individual closet, ensuring ample storage space for all your belongings. Adjacent to the carport, you'll find a large pantry/storage area, making it easy to unload groceries and store items conveniently. The yard also includes a separate storage shed, ideal for gardening tools, bicycles, or other outdoor equipment. Located in the heart of Key West, this charming and well-appointed house offers the perfect blend of comfort, convenience, and style. Don't miss the opportunity to make this delightful home your own. For more information or to schedule a viewing, contact us today! Thank you

2809 Flagler Ave, Key West

$849,000

5 Beds ⋅ 2 Baths ⋅ 618514 MLS

EXCELLENT OPPORTUNITY! EXCELLENT LOCATION! This duplex offers several terrific options for the buyer -- from building a brand new home in a prime location to a top to bottom renovation project. In either case, you could choose to make it your own, or make it an income producing investment by living in one side and renting out the other or even renovating it to sell. Additionally, this property would be perfect for staff housing. Plenty of options in a great location make this one to see.

1432 Eliza 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

$2,895,000

3 Beds ⋅ 4 Baths ⋅ 612545 MLS

Welcome to 3615 Eagle Avenue, a stunning, spacious, custom built residence surrounded by it's own private botanical garden. The oversized double door entryway indicates what awaits you on the inside. Large sweeping rooms with high cathedral ceilings, gorgeous tile floors, double doors opening to the garden from every room, all designed with one-level living and an emphasis on engaging one eye to the stunning nature that surrounds you. The chef in your family will dance with delight in the spacious kitchen built for creating and entertaining with new Sub Zero refrigerator, gas stove, two dishwashers, wine cooler, and ice machine. Each room has been upgraded with impact windows and doors with views of the luscious tropical delights that await you outside from every angle. Currently configured as a three bedroom with an additional spacious office that would easily convert to a fourth bedroom. Master suite privately located in front of the house with a newly renovated master bath that exudes luxury and style. The 12,000 sq. ft. lot encompasses a large thrilling botanical garden full of life with an emphasis on native plants and palms attracting all the local birds and butterflies. A covered pavilion overlooking the 33' pool and spa with a sand walkway that meanders through the tropical plants. A double car garage with built in storage with additional off-street covered parking for three more vehicles to store all the family toys. House is equipped with a generator, lots of storage, separate utility entryway, exterior lighting and irrigation. Book your showing today to see this extraordinary home as you won't be disappointed.

3615 Eagle Ave, Key West

$1,354,000

3 Beds ⋅ 3 Baths ⋅ 618714 MLS

This Residential Duplex can be purchased alone or with adjacent property located at 1610 Laird. Street. Owner financing possible. Long term rentals are in place with great payment history and income. Leases must convey at closing. Front unit consists of two bedrooms and one bathroom, living room, dining area, covered patio, full size kitchen along with off street parking and washer. The second unit is located in the backyard and is a townhouse with one bedroom, one full kitchen and additional living space upstairs. Must have 24 hours to show.

1612 Laird St, Key West

$1,500

2 Baths ⋅ 617942 MLS

Offices on Eaton Street located in downtown Key West. If you are looking for a small private office join the friendly business environment at Key West Theater catering to local small business owners. Office 215 is a corner office with a large open space and close, approximately 320sq.ft. Wifi, electric and water included.

524 Eaton St Unit 215, Key West

$1,195,000

3 Beds ⋅ 2 Baths ⋅ 616629 MLS

Nestled down a private and picturesque lane, this charming conch-style cottage offers the perfect blend of island charm and comfort. Featuring 3 bedrooms and 2 full baths, the home is thoughtfully designed for relaxed living and effortless entertaining. Step into a beautifully landscaped backyard with a newly built pergola—ideal for dining and unwinding in the spa beneath the stars. Though compact, the outdoor space is practical and inviting, perfect for intimate gatherings or quiet evenings. Inside, you'll find rare Dade County pine, vaulted ceilings, and a private patio that captures the essence of Key West living. The home comes fully furnished, making it move-in ready or a turnkey rental.

711 Galveston Ln, Key West

$798,000

2 Beds ⋅ 1 Baths ⋅ 608965 MLS

Tare Down You can build your dream house to your specifications just 4 houses to the beach. Close to the White Street pier. Walk to pickle ball and tennis courts. Higgs beach is just 3 minutes away. Ride your bikes to Duval Street only 1.3 mile away. This large corner lot is perfectly located. Even the birds know when to fly South.

1521 Rose 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

$1,875,000

4 Beds ⋅ 2 Baths ⋅ 618211 MLS

This rare Key West treasure hasn't changed hands in over a century, and it sits on the most coveted block in Old Town. A true time capsule waiting to be revived, it's the last of its kind not yet renovated--so you won't be buying someone else's overpriced remodel. Bring your imagination and restore this home to its original, sun-soaked beauty. There's not another lot like it in Old Town. The nearly 5,000-square-foot lot stretches from Fleming Street to Stickeny Lane, offering ample off-street parking and a golden opportunity to expand your tropical living dreams. Nestled in the heart of Old Town, 1115 is just blocks from the historic Seaport and a stone's throw from the city's famous restaurants and nightlife. Early 1900s Sanborn maps even hint at an additional house on the property that may be rebuilt with city permissions (buyers to verify). The home still contains generous pockets of its original Dade County pine, along with historic windows and double balconies that invite sea breezes and sunset cocktails. Currently a legal duplex, each side offers 2 bedrooms and 1 bath. You can keep the duplex as-is, or transform it into a stunning single-family residence in the most sought-after neighborhood in all of Key West.

1115 Fleming 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

$998,000

1 Beds ⋅ 1 Baths ⋅ 618122 MLS

Step into a piece of Old Town Key West history. Built in 1928, this storybook Old Town cottage captures everything to love about Key West including its timeless character and that easy island rhythm you can feel the moment you arrive. Light, bright, and beautifully furnished, it's move-in ready, the perfect turn-key retreat for anyone dreaming of a second home or an easy vacation rental in the heart of Key West. Inside, you'll find soaring wood-vaulted ceilings and warm floors features that hint to island's past. The airy loft adds extra space and character, while the private back deck invites unforgettable evenings dining under the stars. Out front, the iconic porch is made for slow evenings, and people-watching ... the classic Key West pastime. Just two blocks from Duval Street, this location is unbeatable, it's close enough to walk to the best restaurants, galleries, and shops, yet tucked away for peace and privacy. Even better, it's in the coveted X-Zone, so no flood insurance is required, and yes, it has its own, coveted off-street parking spot This isn't just a home, it's a private oasis. It's YOUR Key West story waiting to be written.

817 Terry Ln, Key West

$925,000

4 Beds ⋅ 3 Baths ⋅ 618352 MLS

Well-maintained duplex offering flexible living and strong income potential in a desirable Key West location. The property features a charming 3-bedroom, 2-bath main home plus a separate 1-bedroom, 1-bath studio cottage—ideal for extended family, guests, or rental income. Both units are thoughtfully laid out with comfortable living spaces and plenty of natural light. Currently fully leased and income-producing, this is an excellent opportunity for investors or owner-occupants looking to offset expenses while enjoying island living.

2004 Patterson Ave, Key West

$1,284,000

3 Beds ⋅ 2 Baths ⋅ 617886 MLS

Located in the heart of Key West, 1712 Laird Street offers a rare blend of central convenience and residential tranquility. Positioned within a short stroll of Smathers Beach, Higgs Beach Park, the Key West Nature Preserve, White Street Pier, and the island's beloved Garden Club and dog park, this home places the best of the island lifestyle quite literally at your doorstep. Duval Street and the Old Town Historic District lie just 1.5 miles away, while Mallory Square and the waterfront—famed for their sunsets, dining, and culture—are approximately 2 miles from the property, allowing effortless access without sacrificing peace and privacy . Designed by an architect with a discerning eye for light and space, the residence showcases a modern open-concept floor plan enhanced by expansive glass elements that invite the outdoors in. Cathedral ceilings soaring from 12 to 15 feet throughout every room create a sense of volume and airiness seldom found in Key West homes, delivering a bright, refined interior that feels both contemporary and timeless . Set on a 5,000-square-foot parcel, the grounds are thoughtfully landscaped with low-maintenance native flora, including seven mature palm trees, a striking gumbo limbo, and established orchids. The result is a private tropical sanctuary—lush, authentic, and effortlessly elegant—perfectly suited for island living without pretense . Large back yard offers plenty of space to add a pool!

1712 Laird St, Key West

$1,175,000

2 Beds ⋅ 2 Baths ⋅ 618511 MLS

This show-stopping luxury condo delivers a rare blend of historic charm with a fully renovated interior that was just completed a few years ago. The first level features an open living and dining plan with 10' ceilings, an abundance of natural light, restored Dade County Pine accent walls, plantation shutters, modern lighting, and tile flooring throughout. The kitchen was built to impress and features a large quartz island, Cafe Collection appliances, a gas range, designer tile backsplash, and a separate coffee and cocktail bar. Practical touches include an entry way storage closet, built-in closet systems, and a full-size GE washer and dryer tucked neatly under the stairs. The upstairs primary suite feels like a private retreat.. it features a sitting area with double French doors that open to the balcony perch where you'll enjoy views of beautiful sunsets through the treetops. The en suite bath is finished with gorgeous Onyx Style slab tile, a double vanity, designer fixtures and a glass shower with statement detailing. This luxury condo is offered fully furnished and turnkey, with local Key West history woven throughout. 30-day rentals are allowed with restrictions, it's in the X Flood Zone, and from here it's always an easy stroll to Fort Zach Beach, Truman Waterfront Park, and the Duval Street corridor for fine dining, shopping, and live entertainment, capturing the ease and energy of Key West living..

927 Thomas St Unit #2, Key West

$1,175,000

2 Beds ⋅ 2 Baths ⋅ 618827 MLS

An UNBEATABLE LOCATION1 This light-filled, Old Town condo just one block to Duval Street! This home shines with 23 windows on two levels and relaxes with its easy, breezy, tropical vibe, landscaped grounds and pool. Turn-key, renovated and furnished, this condo resides in the historic Campbell Building on Fleming Street, one of Old Town's most coveted. Enjoy a gorgeous interior with pine floors throughout, new ac mini splits in every room, plentiful storage and a spacious, modern kitchen. The hefty project of converting all 23 windows to impact glass has been done for you, ensuring superior wind protection, an extremely quiet inside space and low energy costs. This unit exudes charm and easy living and feels like a true home all with immediate access to the best of Key West. In a moment you can be dining at your favorite restaurant, watching the sunset at Mallory, listening to live music or hitting Fausto's market for those last minute grocery items. And you will love the balcony where you can take in the hustle and bustle of passer-byers from above, laze away the morning while sipping on your Cuban Coffee, enjoy cocktails under the stars or watch the Fantasy Fest Local's Parade from the best seat in the house! Unit 4 has been fully renovated and needs nothing but you! A custom designed kitchen with ample storage, stainless steel appliances, quartz counters and a white Kohler, porcelain farmer's sink overlooking Fleming below make cooking and entertaining a breeze and a joy. Only 9 units reside in the Campbell Building, all nestled on a beautifully landscaped compound with a large pool. This is a great place to live and will also make for a lucrative vacation rental. Enjoy living on Millionaire's Row with access to all that makes Key West the best place to live the island lifestyle.

617 Fleming St Unit APT 4, Key West

$1,100,000

1 Beds ⋅ 2 Baths ⋅ 617909 MLS

Charming Old Town Retreat in X Flood Zone! Step into island living with this beautifully renovated 1-bedroom, 1.5-bath home, plus sleeping loft and cabana, in the heart of Old Town Key West. Thoughtfully updated with quartz countertops, custom wood cabinetry, and top-of-the-line stainless steel appliances, this home seamlessly blends modern comfort with historic charm. A cozy sleeping loft offers extra space for guests or lounging, while a separate structure on the property can serve as a studio, guest room, or private cabana. Nestled on a generously sized lot in the desirable X flood zone, this home also conveys with a 1/10 interest in a private parking lot behind the residence—a rare Key West perk! Don't miss your chance to own a versatile and stylish island escape in one of Key West's most sought-after neighborhoods.

738 Olivia St, Key West

$2,255,000

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

$1,200,000

3 Beds ⋅ 1 Baths ⋅ 617022 MLS

Transient receiver site - Truly a diamond in the rough. Great location, behind the Hemingway House between Duval and Whitehead Street. Lot backs up to Whalton Lane (off Duval) with room for parking and a pool. Bring your contractor and a transient license to the property and she will truly shine like the Hope Diamond with happiness and prosperity. Buyers should do their own due diligence to determine transient license receivership requirements prior to making an offer. Probate is required.

418 Olivia St, Key West

$1,196,000

3 Beds ⋅ 1 Baths ⋅ 614442 MLS

Location, Location, Location! Old Town in X-Flood Zone on Solaris Hill with Off Street Parking! Quintessential conch cottage has a cozy front porch & has been in the same family for decades. All wood structure shows a glimpse of wood boards behind the existing interior paneling. This is believed to be the much-desired Dade County Pine. Roof and main electrical panel replaced (w/ permits) in 2014. House is currently configured as seven rooms in total (3 bed, 1 bath, den, dining & kitchen). Front yard provides the highly coveted Off-Street-Parking & the back yard is 31 Ft X 26 Ft (total 806 sq ft). House is a renovation project. This is an estate sale & there will be NO repair and NO clean up by the sellers. However, there will be NO waiting on Probate & NO court approvals needed. Make 719 Elizabeth St your Old Town Island Oasis!

719 Elizabeth 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

$3,599,000

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

$1,354,000

3 Beds ⋅ 2 Baths ⋅ 618728 MLS

This property can also be purchased along with the adjacent property 1612 Laird. Owner financing possible. Three bedrooms with room for expansion along with a guest room. Kitchen with stainless steel appliances and dedicated area for dining table and Florida room that leads to the out door seating areas. Plenty of off street parking with expansive covered area for all your treasures. Several out door seating areas with additional covered areas for entertainment and outside shower. Twenty- four hours needed to show.

1610 Laird 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

$2,950,000

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

$799,000

3 Beds ⋅ 2 Baths ⋅ 618386 MLS

Enjoy relaxed island living in this spacious 3-bedroom, 2-bath condo located in the gated community of Key West by the Sea, directly across from Smathers Beach. This bright and comfortable residence offers an open living and dining area, a private balcony with tropical surroundings, and a thoughtful layout ideal for everyday living or hosting guests. Residents enjoy resort-style amenities including two swimming pools, tennis courts, a clubhouse, and beautifully landscaped grounds. Conveniently located near beaches, shopping, dining, and all the attractions of Old Town Key West, this condo is perfect as a primary residence, second home, or island getaway.

2601 S Roosevelt Blvd Unit 304C, Key West

$999,999

3 Beds ⋅ 3 Baths ⋅ 618760 MLS

Income producing Duplex in Old Town Key West! The Owner prefer to hold the financed note for a new owner. Fully renovated offering strong income potential and turnkey condition. Recent upgrades include a new roof, siding, impact windows, updated kitchens and baths, and new flooring in the rear unit. The downstairs features two lockout units--rear unit with large private backyard, and front unit with private front porch. Upstairs treetop unit is currently tenant-occupied. Centrally located directly across from Bayview Park, this property offers consistent rental demand and separate electric. X Flood zone with plenty of room for a pool in the backyard.

1018 Georgia St, Key West

$820,000

1 Beds ⋅ 1 Baths ⋅ 618001 MLS

Old Town Condo Near Duval: Bright 1-bedroom, 1-bath condo located in the heart of Historic Old Town Key West. Featuring high ceilings and an open floor plan, this residence is filled with natural light. Just steps from Duval Street, dining, shopping, and entertainment. Ideal as a vacation rental, investment property, or personal island retreat.OWNERS MAY HAVE A PET WITH ASSOCIATION APPROVAL.

817 Eaton St Unit 1, Key West

$1,950,000

3 Baths ⋅ 617342 MLS

Key West Jeep Adventures - Turnkey Tourism Business in Paradise Business Overview: Key West Jeep Adventures is a thriving, turn-key adventure rental company located in the heart of Florida's most iconic island destination. Specializing in premium Jeep Wrangler rentals, this business offers tourists the ultimate way to explore the Florida Keys in style and comfort. With a strong brand presence, high customer satisfaction, and a fleet of well-maintained, island-ready vehicles, this is a rare opportunity to own a profitable lifestyle business in paradise. Highlights: • Diverse Fleet: A mix of 2-door and 4-door Jeep Wranglers, many with convertible tops and custom island-themed wraps. • Prime Location: Centrally located in Key West with high visibility and easy access for tourists arriving by plane, cruise, or car. • Established Brand: Strong online presence, 5-star reviews, and a loyal customer base. • Proven Profitability: Consistent year-over-year revenue growth with scalable operations. • Turnkey Operation: Includes all vehicles, booking systems, website, marketing assets, and trained staff. • Partnership Ready: Relationships with local hotels, resorts, and travel agencies already in place. Growth Potential: Opportunities abound to expand services into guided tours, mapped excursions, or additional rental offerings such as scooters, e-bikes, or paddleboards. With Key West's year-round tourism and growing demand for experiential travel, the sky's the limit. Ideal Buyer: Perfect for an entrepreneur seeking a lifestyle business, an investor looking for a high-margin tourism asset, or a strategic buyer in the travel or adventure rental space. PRICE: $1,950,000 BUSINESS OP, INVENTORY: $2,700,000 SOLD SEPERATLY

3424 N Roosevelt Blvd, Key West

$699,000

1 Beds ⋅ 1 Baths ⋅ 618077 MLS

Picture perfect condo located in 1 of 2 historic buildings totaling 8 units with a generous sized shared pool and lounging area. This setup is ideal for 1-2 people looking for a low maintenance island address in a quiet neighborhood walkable to all that Old Town, the Historic Seaport and Duval Street has to offer. This unit welcomes you with 10ft ceilings and Dade County pine walls and floors throughout. Enjoy the charming and peaceful screened in patio that brings the outdoor in just off of the living room. This one bedroom floor plan also enjoys a generous size ensuite bathroom and full size washer and dryer. The petite and efficient kitchen is all you need to complete your island home. If your looking for a slice of the island life to call your own this condo allows you to come and go with the ease of a well run condo association the handles all of the worries on your behalf!

1203 Newton St Unit 1, Key West

$20,350,000

611311 MLS

Located at 521 United Street, the Southernmost Inn was originally built in the 1800s as a Francisco Marrero cigar factory. With much of the old cigar factory features restored, the award-winning transformation allowed the old Key West designs to live on throughout a modern-day establishment. The Southernmost Inn offers 38 newly renovated rooms featuring modern interiors with a classic neo-colonial design. All guestrooms feature en-suite bathrooms, flat screen TVs, and colonial wooden blinds. The Boutique also boasts a gorgeous outdoor common area with lush gardens, two pools, one jacuzzi, a bar (currently closed), and a relaxing dining area.

521 United St, 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

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