Tour Inside 1868 Maine Capt. Jacob Winslow Townhouse With Original Jewel Light

Standing gracefully on Portland’s historic Deering Street, the Capt. Jacob Winslow Townhouse is a quintessential example of Maine’s 19th-century architectural heritage.

Built in 1868 by renowned Portland architect Francis H. Fassett—the city’s most celebrated post–Great Fire designer—the home reflects the confidence and craftsmanship of a booming maritime era.

Designed for Captain Jacob Winslow, a prominent sea merchant and civic leader, this Second Empire-style townhouse still shines today with remarkable preservation, period detailing, and an unmistakable sense of grandeur.

From the street, the house immediately captures attention with its signature mansard roof, a hallmark of the Second Empire aesthetic, and its balanced façade adorned with tall, arched windows.

The multicolored slate roof tiles and ornate bracketed cornices add richness and texture, while the entryway, framed by decorative moldings and an original jewel-like transom light, announces the home’s enduring elegance.

Step inside, and the sense of history deepens. The foyer opens to reveal a commanding central staircase, its carved banister polished by more than 150 years of use.

Every element—from the decorative plaster ceiling medallions to the intricate door casings—tells the story of Fassett’s precision and Portland’s postwar optimism.

The first floor retains the original double parlor, an exquisite space once used for formal gatherings and family events. Here, decorative wall paintings and built-in bookcases remain intact, lending the rooms a warm authenticity rarely found today.

The dining room, designed for large gatherings, still features the walk-in china closet that once stored fine imported wares brought back from Winslow’s voyages. Beyond it lies the kitchen, ready for restoration, where one can imagine the bustle of Victorian-era domestic life.

Over the decades, the first floor has also served various community roles, housing a dentist’s office, a therapist’s practice, and other small businesses—each adapting the space without erasing its historic identity. This flexibility continues to define the home’s appeal today.

The second floor contains a two-bedroom apartment, filled with natural light and flexible in layout. Its high ceilings, tall windows, and period woodwork create a serene and timeless atmosphere.

The third floor, newly renovated, includes a bright one-bedroom apartment complete with updated kitchen appliances, refinished cabinetry, and abundant storage.

Despite modern upgrades, the restoration work has been handled with care to maintain the building’s Victorian character.

Descending to the lower level, one finds perhaps the home’s most unexpected treasure—a billiard and game room with magnificent woodwork and a grand fireplace. It’s a space that speaks to a time when social leisure was as important as style, and it remains one of the most atmospheric parts of the property.

Outside, the townhouse enjoys ample parking, an unusual benefit for historic Portland, and a rare attached two-car garage, blending 19th-century architecture with modern convenience.

The property’s potential is as versatile as it is charming. It can serve as a single-family residence, a live-work space, or continue in its current multi-unit configuration—all while preserving the essence of a Victorian masterpiece.

Its location on Deering Street is equally compelling. Set within the Deering Street Historic District, the home is just steps from Portland’s Arts District, West End, Downtown, and the Old Port. Residents and visitors alike enjoy easy access to award-winning restaurants, galleries, and shops that define Portland’s cultural vibrancy.

The Capt. Jacob Winslow Townhouse stands as more than a relic of the past—it’s a living embodiment of Portland’s resilience and artistry. Designed by one of Maine’s greatest architects and shaped by a seafaring merchant’s legacy, this 1868 home bridges history and modern life with quiet dignity.

Whether admired for its craftsmanship, its adaptable interior, or its glowing jewel-like transom light, the Winslow residence remains a true treasure of Portland’s architectural heritage—a perfect blend of past elegance and present-day charm.