Old Town

103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. A dramatic staircase leads to a second floor walkway which is open to the main level. On one end is the primary bedroom with a large en suite. At the other end is an en suite guest bedroom. The custom features throughout are evidence of the ingenuity used in the design of this impressive home. A third bedroom and full bath on the main floor features doors that open to a separate private patio. The kitchen features custom wood cabinets and granite countertops and is open to the dining area. Extra tall windows and french doors flood the home with sunlight. Entertaining indoors or out is easy in this spacious home. A wet bar features custom built ins plus an icemaker and refrigerator. Fronted by a white picket fence, the home sits back from the street and is adorned by tropical foliage. This unique structure with thick brick walls and impressivly tall windows offers passers by a glimpse of the historic origins of the Truman Annex. Its location in the heart of old town Key West provides easy walkability to the waterfront promenade, Ft. Taylor beach, cultural venues, shops and restaurants. The property is set on two lots with a large swimming pool and spa between the covered open air loggia and parking. There's a poolside outdoor shower and lots of space for entertaining on a grand or intimate scale. This estate home is one of a kind was restored to the highest standards. One must see this home to appreciate the incredible design and attention to detail that went into this historic treasure. $6,850,000 Active

103 Front Street KEY WEST, Florida

3 Beds 3 Baths 4,200 SqFt 0.2 Acres

This unique three residence property is ideally located just steps from the Historic Seaport and Fausto's grocery store in the heart of Old Town. A newly constructed building offers a spacious 3-bedroom, 3.5-bath main residence overlooking the pool, with a generous 2-bedroom, 2.5-bath apartment above. At the front of the property, a charming 1-bedroom, 1-bath home features a large garden with deep porch facing Eaton Street and the lively atmosphere of Old Town. All three residences showcase beautifully curated interiors with a blend of luxury antiques and distinctive fixtures. The property is anchored by a tropical courtyard pool, gated entry, and three off-street parking spaces, creating the perfect private compound for an owner seeking space for guests or exceptional income potential. $5,950,000 Active

723 Eaton Street KEY WEST, Florida

6 Beds 8 Baths 4,094 SqFt 0.19 Acres

924 Flagler is an iconic home in the sought after Casa Marina area. Totally renovated and upgraded, this home has received multiple design and restoration awards. The incredible property has over 12,300 square feet of expansive grounds including meandering walkways, an outbuilding, a two car garage. It features lush tropical landscaping and spralling open spaces. The interior of this concrete home features 14 ft. ceilings on the first floor and 12' on the second floor. A sunroom entry is lined with Palladian doors and opens to a patio and the living room. An office, powder room, large dining room and the chef's kitchen complete the first floor. The second floor features the primary bedroom and a sitting room converted from a fourth bedroom plus two more guest bedrooms and a bath. A spacious second floor sun porch offers beautiful views and more space to relax. The list of improvements, upgrades and amenities is extensive and include hurricane rated roofs over the home and the garage, custom mahogany wood windows and doors, copper gutters and downspouts to a 7,000 gallon cistern used for irrigation, custom Hanson & Bringle millwork and cabinetry, Cat 5 & 6 wiring, McIntosh audio system throughout the house, a whole house generator, updated electric and plumbing, an electronic gated driveway. This one of a kind home is a Key West treasure in an excellent location. $4,595,000 Active

924 Flagler Avenue KEY WEST, Florida

4 Beds 3 Baths 2,064 SqFt 0.28 Acres

Experience refined island living in this BRAND NEW residence perfectly situated on a generous 10,800 square foot lot and elevated at an impressive 10.5 feet. This 3 bedroom, 3.5 bath home is a testament to modern coastal luxury, where timeless design meets effortless functionality.Constructed entirely of concrete, the open concept layout is framed by soaring cathedral ceilings and expansive impact-glass doors that bathe the interiors in natural light and invite the outdoors in. Premium finishes and high end appliances enhance every detail, creating a sophisticated yet comfortable living environment.The home features two primary suites -- one upstairs and one downstairs -- each with private outdoor access for seamless indoor-outdoor living. A separate, fully equipped guest cottage offers privacy and tranquility, complete with wide sliding doors that capture lush garden views.Designed by renowned landscape architect Craig Reynolds, the tropical grounds are a private oasis. Multiple covered patios surround the heated and chilled pool with sun shelf seating, while a striking coral rock outdoor shower adds a touch of island luxury.Additional features include a 481 square foot garage for parking and storage, a whole house Generac generator, standing seam metal roof, and all impact rated windows and doors, ensuring peace of mind and durability.Every element of this turnkey property has been curated with precision and care, resulting in a one-of-a-kind retreat that embodies the essence of elegant coastal living in Key West. $3,950,000 Active

3741 Eagle Avenue KEY WEST, Florida

3 Beds 4 Baths 2,744 SqFt 0.14 Acres

This unique three residence property is ideally located just steps from the Historic Seaport and Fausto's grocery store in the heart of Old Town. A newly constructed building offers a spacious 3-bedroom, 3.5-bath main residence overlooking the pool, with a generous 2-bedroom, 2.5-bath apartment above. At the front of the property, a charming 1-bedroom, 1-bath home features a large garden with deep porch facing Eaton Street and the lively atmosphere of Old Town. All three residences showcase beautifully curated interiors with a blend of luxury antiques and distinctive fixtures. The property is anchored by a tropical courtyard pool, gated entry, and three off-street parking spaces, creating the perfect private compound for an owner seeking space for guests or exceptional income potential. $5,950,000 Active

723 Eaton Street KEY WEST, Florida

6 Beds 8 Baths 4,094 SqFt 0.19 Acres

Located in the heart of the Seaport Historic District, on two lots, this charming Conch home features a 2-bedroom main residence and a separate 1-bedroom guest cottage. The property offers exceptional outdoor living, highlighted by a large L-shaped, recently resurfaced heated pool and spa, surrounded by brick and wood decking. Inside, painted Dade County Pine accent walls add authentic character, while the marble-appointed bathrooms elevate the home's appeal. The spacious primary suite offers flexibility, with the option to be located either upstairs or in the downstairs bedroom. The kitchen and living area feature bar-top seating and a cozy cove dining space, flanked by French doors that open to the lush, tropical outdoor setting. The owners have completed extensive due diligence, including updated plumbing, electrical systems, and water heaters. The property offers off-street bricked parking. $2,000,000 Active

1110 Elgin Lane KEY WEST, Florida

3 Beds 3 Baths 1,256 SqFt 0.09 Acres

Located in the heart of Old Town, 616 Eaton Street tells a story that spans more than a century. Built in 1911 and thoughtfully brought into the present day, with additions & renovations, this property reflects the enduring character of Key West while offering the comforts and conveniences of modern living. This 5BD, 5 full BA, and 2 half BA estate spans over 4,000sf and sits on an expansive 12,478sf lot. Set back from the street, it offers a level of privacy that is rare for such a central location. The main residence is designed for both everyday living & entertaining and has been furnished with new furniture & finishings adding a refined & move in ready touch. The fabulous kitchen, outfitted with top of the line finishes, opens through huge sliding glass windows to an outdoor bar & entertaining pavilion creating a seamless indoor & outdoor experience. Upstairs, the primary suite offers a quiet escape with its own office, laundry, and a generous covered porch. Throughout the home, reclaimed hardwood floors from the Biltmore, tall ceilings, and natural light highlight the balance between historic charm & modern upgrades.The outdoor space serves as the heart of the property, anchored by a heated & chilled saltwater pool with a tranquil water feature. Two detached guest houses provide a total of 3BD & 3BA, complemented by an additional cottage that can function as a 4th bedroom & bath or a private entertaining retreat. The versatility of this home is truly exceptional, ideal for hosting guests, extended stays, or creating secluded personal spaces. Additional features include a 1,500sf climate controlled attic for storage, off-street parking for up to 7 vehicles, a carport, and a golf cart garage. Positioned in the desirable X flood zone and just 2 blocks from Duval St. and the Historic Seaport, this property represents a rare opportunity to own a significant piece of Key West history, thoughtfully updated for modern living. $7,495,000 Active

616 Eaton Street KEY WEST, Florida

5 Beds 7 Baths 4,000 SqFt 0.29 Acres

A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House--one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom villa--each with its own private pool.Zoned with two transient licenses and off-street parking for 4+ vehicles, this exceptional property offers unmatched flexibility for luxury rentals or private use.The grand mansion was reimagined in July 2022 by a local designer, featuring fresh paint, stylish new furnishings, and 12-foot soaring ceilings. The main level includes two guest rooms with baths, formal living and dining rooms, a parlor, and a well-appointed kitchen that opens to the pool deck and outdoor dining area.Upstairs, four en suite bedrooms include two primary suites with private balconies--one overlooking Simonton Street, the other with views of the pool. A spacious third-floor suite, accessed via an interior or exterior staircase, offers a private living room, wet bar, and yet another balcony retreat.The villa, renovated to the studs in 2014, offers a clean, contemporary design with 4 bedrooms, 4 baths, full kitchen, living area, private pool, and outdoor bar--perfect for entertaining.Whether you choose to rent the estate in its entirety or as two separate homes, The Watson House is a rare asset in Key West's luxury rental market--highly sought-after and consistently booked well in advance. $7,490,000 Active

525 Simonton Street KEY WEST, Florida

11 Beds 11 Baths 3,034 SqFt

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