Old Town

Private Compound- 723 Eaton Street and 329 Peacon Lane, Old Town.An extraordinary property in the heart of Old Town, this compound is a masterclass in island living. Spanning from 723 Eaton Street to 329 Peacon Lane, the property includes one brand new home plus three additional beautifully reimagined residences, all set behind lush, professionally designed tropical landscaping with gated entrances on both sides. Located just steps from the Historic Seaport and near Fausto's Grocery, this prime location lies within Key West's oldest and most storied neighborhood.At the center of the compound is a grand yet welcoming main residence--brand-new construction featuring three bedrooms, three and a half baths, soaring ceilings, tall doors and windows, and a seamless flow between indoor and outdoor spaces. French doors lead to a serene courtyard with a stunning pool and water feature, creating the perfect backdrop for elegant entertaining or peaceful retreat.Three additional residences offer versatility and privacy, including two one-bedroom, one-bath apartments, each with private outdoor space, plus a lovely two-bedroom, two and a half-bath, top floor, pied-a-terre. All have been fully renovated and include private laundry. The Peacon Lane apartment and the main home are currently operated as high-performing monthly vacation rentals, making this an attractive investment opportunity as well.Additional features include five off-street parking spaces, including two designated for golf carts, a commercial-grade fire suppression system throughout, and secure basement storage. Every inch of this property reflects care, craftsmanship, and a deep respect for Key West's architectural heritage--with none of the headaches of renovation left to do.Whether you're seeking a luxurious personal retreat, a flexible multi-residence compound, or a legacy investment in one of Key West's most desirable neighborhoods, this is truly a once-in-a-generation opportunity. $7,500,000 Active

723 Eaton Street KEY WEST, Florida

7 Beds 9 Baths 3,000 SqFt 0.19 Acres

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

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. $4,130,000 Active

3741 Eagle Avenue KEY WEST, Florida

3 Beds 4 Baths 2,744 SqFt 0.14 Acres

Located in the highly regarded Casa Marina neighborhood, this exceptional property offers a unique opportunity to own a piece of Key West history. Ernest Hemingway the iconic literary figure once called this house his Winter retreat during 1928 -1929, where he penned the timeless classic, 'A FAREWELL TO ARMS.'' This sprawling single story property spans an impressive 8100 square feet, occupying a prominent corner lot, with a reimagined interior floor-plan. Constructed with white-painted Savannah brick over a wood frame, this residence exudes classic charm with a modern twist. Tall ceilings and a welcoming fireplace create an inviting atmosphere. Sliding glass doors seamlessly connect the interior to the outdoor patio, allowing for a harmonious blend of indoor and outdoor living spaces. The outdoor space is a tropical paradise, complete with a heated pool and soothing water feature. The main house features 3 bedrooms, 2 bathrooms, and a laundry area. Two of the bedrooms share a bathroom, while the primary suite offers a generously sized bathroom with a bath tub, double sinks, and an indoor and an outdoor shower. Enjoy the airy ambiance of the open floor plan, with a spacious living room and dining area that together span over approximately 1200 square feet. The modern kitchen is well-appointed, with easy access to the pool area and the charming conch-style 1/1 guesthouse. The main house has a semi-circular driveway and can accommodate 3-4 cars. The guesthouse also includes its own entrance on Walton Street and an off-street parking space. $2,850,000 Active

1100 South Street KEY WEST, Florida

4 Beds 3 Baths 2,880 SqFt 0.19 Acres

Private Compound- 723 Eaton Street and 329 Peacon Lane, Old Town.An extraordinary property in the heart of Old Town, this compound is a masterclass in island living. Spanning from 723 Eaton Street to 329 Peacon Lane, the property includes one brand new home plus three additional beautifully reimagined residences, all set behind lush, professionally designed tropical landscaping with gated entrances on both sides. Located just steps from the Historic Seaport and near Fausto's Grocery, this prime location lies within Key West's oldest and most storied neighborhood.At the center of the compound is a grand yet welcoming main residence--brand-new construction featuring three bedrooms, three and a half baths, soaring ceilings, tall doors and windows, and a seamless flow between indoor and outdoor spaces. French doors lead to a serene courtyard with a stunning pool and water feature, creating the perfect backdrop for elegant entertaining or peaceful retreat.Three additional residences offer versatility and privacy, including two one-bedroom, one-bath apartments, each with private outdoor space, plus a lovely two-bedroom, two and a half-bath, top floor, pied-a-terre. All have been fully renovated and include private laundry. The Peacon Lane apartment and the main home are currently operated as high-performing monthly vacation rentals, making this an attractive investment opportunity as well.Additional features include five off-street parking spaces, including two designated for golf carts, a commercial-grade fire suppression system throughout, and secure basement storage. Every inch of this property reflects care, craftsmanship, and a deep respect for Key West's architectural heritage--with none of the headaches of renovation left to do.Whether you're seeking a luxurious personal retreat, a flexible multi-residence compound, or a legacy investment in one of Key West's most desirable neighborhoods, this is truly a once-in-a-generation opportunity. $7,500,000 Active

723 Eaton Street KEY WEST, Florida

7 Beds 9 Baths 3,000 SqFt 0.19 Acres

This Conch home has been opened up to provide a large living room with high ceilings and a great sense of space. It features original Dade Pine walls and custom built-in bookcases. The Dade County pine looks to be in beautiful condition. The entire upstairs is the primary bedroom plus a half bath and an enormous walk in closet, office and plenty of storage. The kitchen, dining room and full bath on the first floor open to the deep back yard. There is plenty of room for a pool and possibly another structure. This home is located in the X500 zone so no flood insurance required. With some TLC and upgrades this historic home offers an excellent upside. Great value. $1,050,000 Active

709 Frances Street KEY WEST, Florida

1 Beds 2 Baths 1,095 SqFt 0.07 Acres

This darling free standing cottage is part of a six unit condominium association. It feels more like a single family home as it is not attached to another property. Inside, the excellent floor plan provides lots of space to comfortably enjoy life in Key West. There is a light filled living / dining room, a well equipped kitchen, a full bath and a primary bedroom with tons of storage and a washer/dryer. The bright interior is fully furnished and creates a relaxed island atmosphere. A back door leads to a small patio where one can dine alfresco or just enjoy the breeze. The pool gets lots of sun and provides a nice place to spend the day. Just outside the compound all of Key West's sought after venues are within an easy walk. The harbour promenade is only a block away and one can easily stroll to Duval, shops, restaurants and entertainment. This charming cottage is in a perfect location for easy access to everything Key West has to offer. Being conveyed fully furnished and equipped, all one has to do is bring their suitcase and start enjoying life at 308 Margaret Street #2. $695,000 Contingent/Show

308 Margaret Street 2 KEY WEST, Florida

1 Beds 1 Baths 420 SqFt 0.02 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. $7,995,000 Active

525 Simonton Street KEY WEST, Florida

11 Beds 11 Baths 3,034 SqFt

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