Old Town

Private Compound on Eaton and Peacon Lane | Old Town Key WestAn extraordinary property in the heart of Old Town, this rare compound is a masterclass in island living. Spanning from Eaton Street to Peacon Lane, the property includes four beautifully reimagined residences 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

Property is being sold with MLS #614841This 3 bedroom 3 bathroom home is located on Riviera canal in Key West. It sits on a 10,000+sqft lot, has a newer pool, outdoor kitchen, 24,000lb boat lift, and outdoor shower. There is plenty of parking, air-conditioned storage and large patio for outdoor entertainment. With its original cuban tile and vaulted ceilings if offers a charming old Key West vibe. **You have the opportunity to own over 20,000sqft of canal frontage in Key West with the purchase of both homes located at 3608 & 3612 Sunrise Drive.Make this a large family compound or reconfigure to one large estate. The possibilities are endless.** $5,800,000 Active

3608 Sunrise Drive KEY WEST, Florida

3 Beds 3 Baths 1,455 SqFt

Property is being sold with MLS #614840This waterfront home on a canal in Key West is ready for your creative touch! With 3 bedrooms, 2 bathrooms, a large 9794 sqft lot and there is plenty of room for the boating enthusiasts. It has a large in ground pool and outdoor fire pit area. **You have the opportunity to own over 20,000sqft of canal frontage in Key West with the purchase or both homes. Make this a large family compound or reconfigure to one large estate. The possibilities are endless.** $5,800,000 Active

3612 Sunrise Drive KEY WEST, Florida

3 Beds 2 Baths 1,641 SqFt

3608 Sunrise Drive & 3612 Sunrise Drive are located next door to each on Riviera canal in Key West. You have the opportunity to own over 20,000sqft of canal frontage in Key West with the purchase or both homes. Make this a large family compound or reconfigure to one large estate. The possibilities are endless.See MLS#s 614840 & 614841 for more photos and property details. $5,800,000 Active

3608 -3612 Sunrise Drive KEY WEST, Florida

6 Beds 5 Baths 3,086 SqFt

Private Compound on Eaton and Peacon Lane | Old Town Key WestAn extraordinary property in the heart of Old Town, this rare compound is a masterclass in island living. Spanning from Eaton Street to Peacon Lane, the property includes four beautifully reimagined residences 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

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

Nestled in the heart of Key West's historic district, 616 Eaton Street is a testament to quality, timeless beauty, and refined living. This single-family residence was constructed in 1911 and painstakingly renovated and reimagined over the last few years culminating in 2024 with the spectacular like new home. Most hidden from the Street, it exudes classic Key West architecture blended with modern elegant designs. With 5 bedrooms, 5 full baths & 2 half baths, the home spans 4,000sf on a large 12,478sf lot. The 2-story primary home contains the living room, dining room, kitchen, 2 office spaces/dens, one of which could be a bedroom if desired, 2 half baths on the living level & a spectacular 2nd floor primary suite with office/ laundry & an enormous outside covered deck for private lounging. Thoughtful renovations include a stunning glass wall that opens between the outdoor dining pavilion & the top of the line kitchen w/ functional pass-through windows from the kitchen to the pool area. Reclaimed hardwood floors & tall ceilings ensure a perfect balance of historical character & contemporary functionality. The substantial living area, accented by natural light, offers a warm & inviting atmosphere & the gorgeous central pool w/ a water feature creates a stunning outdoor oasis & is perfect for entertaining. Surrounding the pool & outdoor dining pavilion are 2 phenomenal guest houses, housing a total of 4BD/4BA plus a full 1,512sf attic w/ staircase that is built for storage. Lots of off-street parking is offered along w/ a carport & small garage. Everything is new, from the hard wood floors & bathrooms to the salt generated heated pool & generator. This property is a rare offering that combines historical significance, luxurious living & an unbeatable location in one of Key West's most coveted neighborhoods. Located in the X flood zone just 2 blocks from both Duval St. & the Historic Seaport, it is walkable to all the wonderful restaurants, galleries & shops. $7,495,000 Active

616 Eaton Street KEY WEST, Florida

5 Beds 7 Baths 4,000 SqFt 0.44 Acres

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