Discover Historic Elegance at 419 Simonton Street, Key West

Nestled in the heart of Old Town Key West lies a one-of-a-kind opportunity to own a meticulously restored home that embodies the spirit of timeless island elegance. Located at 419 Simonton Street, Unit A, this remarkable property stretches the boundaries of historic preservation and modern luxury. Built before 1889 and fully reimagined for contemporary living, this residence speaks to those who appreciate architectural heritage thoughtfully updated for today’s comfort.

A Seamless Blend of Old and New

The home was once a mixed-use building, home to a flower shop on the lower floor and an upstairs living area. Fast forward to 2026, and the structure has undergone a complete transformation, reimagined from the ground up while preserving its Old Town character. Every system, surface, and finish is brand new, reflecting quality craftsmanship with timeless design sensibilities. Architect-led planning and elegant construction preserve the home’s historic appeal while optimizing functionality for modern lifestyles.

The interiors are curated by Ben Teague Design, known for blending classic luxury with contemporary warmth. From the choice of materials to the flow of the living space, every inch of the home has been considered with purpose. You’ll find chic yet understated finishes, layered palettes, and furnishings that marry comfort and style beautifully—offered fully furnished for a move-in-ready experience.

Flowing Indoor and Outdoor Living

The main residence consists of two bedrooms and two-and-a-half bathrooms. The primary suite is located upstairs and opens onto a classically styled Key West porch. This private space evokes the leisurely pace of island life, perfect for savoring your morning coffee or evening breeze. A second porch downstairs creates a sense of extended living, integrating the indoors with the outdoors seamlessly.

The home’s landscaping, curated by professional designers, enhances curb appeal and elevates the sense of arrival. Timeless proportions and thoughtful detailing abound, representing a rare convergence of beauty and simplicity in a home that feels both historic and forward-looking.

To learn more about this exceptional property, View Property Listing.

Architectural Details That Define Quality

The essence of Old Town Key West is captured through its architectural elements, and 419 Simonton Street doesn’t disappoint. Crown moldings, natural wood flooring, and traditional sash windows call back to the home’s rich past, while smart-home upgrades and energy-efficient systems ensure long-term peace of mind. Stylized lighting fixtures, cabinet hardware, and custom window treatments work together to complement the architecture without overshadowing it.

Set on a lot with one of the highest elevations in Old Town, the home is located in the sought-after X-500 flood zone. Privacy and security are further bolstered by a thoughtfully structured HOA that enforces high standards while preserving the charm and integrity of each residence.

YouTube Virtual Tour

Take a closer look with this guided YouTube walkthrough: 419 Simonton Street Virtual Tour

A Rare Find in the Heart of Key West

The home includes an attached residential unit positioned at the rear of the main house, as well as a detached unit ideally situated for optimal privacy. This trio of dwellings creates a unique dynamic within the HOA, balancing shared stewardship with individual solitude. It is a thoughtful community structure that amplifies the value of ownership and supports long-term property care.

Located on one of Key West’s most iconic streets, 419 Simonton Street is more than a place to live—it’s a piece of paradise ready to be called home. View Property Listing for more images and property details.

Meet the Listing Agent: Jackson Kaufelt of Truman and Company

Representing this iconic property is Jackson Kaufelt, a trusted name in the Key West luxury real estate market. Jackson is a valued associate of Truman and Company, one of the region’s most prestigious brokerages with a legacy of excellence in coastal Florida real estate. With a deep understanding of architectural history, design-forward living, and a comprehensive grasp of market trends, Jackson offers a tailored client experience grounded in professionalism and trust.

Truman and Company has earned its reputation through unwavering integrity, exceptional client service, and an unmatched record of property success stories. Together, Jackson and the firm stand ready to guide buyers through the acquisition of one of Old Town’s most remarkable offerings.

Explore the Best of Key West Living

The allure of Old Town Key West extends far beyond its pretty porches and historic streetscapes. The neighborhood is known for its walkability, vibrant culture, and laid-back lifestyle. Within walking distance of your front door, you’ll find an array of world-class restaurants, romantic cafés, artistic boutiques, and charming galleries. Popular eateries like Blue Heaven, Santiago’s Bodega, and The Cafe are local favorites beloved by residents and tourists alike.

Families will appreciate proximity to top-rated schools such as Horace O’Bryant School and Montessori Children’s School. The Key West Library and custom community programs offer a wealth of educational and recreational opportunities for residents of all ages. Key West High School—known for its robust extracurricular programs—rounds out the region’s educational offerings.

For those seeking entertainment, local attractions include Mallory Square’s sunset celebrations, the Ernest Hemingway Home & Museum, and the Southernmost Point Buoy. Accessible beaches, marinas, and yoga studios are just blocks away, creating a quality of life that feels idyllic yet connected.

Summary and Invitation

Rarely does a home so beautifully unite cultural significance, architectural integrity, and modern livability as 419 Simonton Street. With its layered history, luxurious upgrades, and unparalleled location, this property reflects the very best of what Old Town Key West has to offer.

If you’re in search of a home that respects the past while celebrating the future, look no further. Contact Jackson Kaufelt today and experience first-hand the charm and detail that make this residence truly special. For more information or to schedule a private tour, View Property Listing.