292 Main Road

Waldo County ME 04848

2409 sq. ft.

87120 sq. ft.

Single-Family

Last sold for $425,000

Virginia Hess, last sold this property on 03 June 2026 after 637 days on market.

Overview

Winfield Scott Pendleton House: A Historic Islesboro Gem. Step back in time and discover the rich history of this stately 1887 Federal-style home, once owned by Winfield Scott Pendleton, a prominent ship captain and influential figure in Islesboro. Built shortly after Pendleton acquired the property in 1876 from his parents, the house served as a summer retreat for the Pendleton family until 1959. This grand home with its distinctive cupola and expansive wrap-around porch is perfect for enjoying the summer breeze and watching island life unfold. French doors off the porch invite you into this elegant old home and once inside the architectural details speak to a bygone era of detailed craftsmanship. Discover an elegant staircase, bespoke built-in closets, a breakfront in the dining room, six-over-six windows, a stained-glass window, and a bespoke carved wooden mantle. Original interior trim throughout the house, along with a claw-foot tub and natural stone vanity, evoke a sense of timeless charm. While the kitchen has been thoughtfully modernized, the home retains its historical integrity. This 5-bedroom residence is prominently situated, offering a mid-island location close to the library, public park and playground, island market, and post office. Beyond the main house, you'll find recently built post and beam two-story outbuildings, offering versatile space for a workshop, storage, or other possibilities. This stately 1887 home is now seeking its next steward—someone who will appreciate its beautiful history, embrace its unique character, and continue to care for and enjoy this magnificent piece of Islesboro heritage.

Features

5 bedrooms

2 bathrooms

2409 sq. ft. floor area

87120 sq. ft. lot size

Single-Family

Estimated Value

We need at least 3 similar 5 bedroom single-family properties sold in Waldo County over the last 12 months.

Property history for 292 Main Road

2026

Sold

$425,000

03 Jun 2026 by Virginia Hess, of Vernon A. Martin, Inc.

Happy sellers in Waldo County

We have insufficient information to provide an overview of customer satisfaction for Waldo County. Viewing the agent profiles, reviews and sales for Waldo County can provide insights for this location.