855.375.4001
Listing Courtesy of: info@catesre.com - Virginia Hess - Cates Real Estate 207-701-5600
$499,000 affordable loan icon

292 Main Road Islesboro, ME 04848

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Single Family Residence
5 Beds
2 Baths
... Bed/Bath
2,409 Sq. Ft.

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Last updated on 12/16/2025 12:21 AM
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. Continue reading
MLS#
1642544
Property Type
Single Family
Bedrooms
5
Bathrooms
1 Full/1 Half
Year Built
1887
Square Feet
2,409 sq. ft
Lot Size
2

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Walk Score measures the walkability of any address, Transit Score measures access to public transit on a scale of 1-100.

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Listing Courtesy of: info@catesre.com - Virginia Hess - Cates Real Estate 207-701-5600
Andrea D. Conner, License DB922721, Xome Inc., License AC90602770, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2025 Maine Real Estate Information System, Inc. All Rights Reserved.
This content last refreshed on 12/16/2025 12:21 AM. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Information is deemed reliable but is not guaranteed.
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