292 & 300 Main Road, Islesboro, ME 04848
Local realty services provided by:Better Homes and Gardens Real Estate The Masiello Group
292 & 300 Main Road,Islesboro, ME 04848
$850,000
- 5 Beds
- 4 Baths
- 4,962 sq. ft.
- Single family
- Active
Listed by: virginia hessinfo@catesre.com
Office: cates real estate
MLS#:1642620
Source:ME_MREIS
Price summary
- Price:$850,000
- Price per sq. ft.:$171.3
About this home
Discover a unique opportunity in Mid-Island Islesboro, where history and potential converge in two remarkable buildings on one property.
The Schoolhouse (300 Main Road): This was formerly the Pendleton School, Islesboro's main elementary school until the early 1950s. Currently operating as the Double Door Gallery during the summer, it features two large open rooms on the first floor with curved walls, bead board, wood paneling, and a half bath. The second floor offers a studio apartment with expansion potential, providing immediate income through gallery rentals and apartment leasing. This property is a piece of history with a bright future, ready for its next chapter as a vibrant art gallery, or unique retail space.
The Main House (292 Main Road): The Winfield Scott Pendleton House. 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. 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. 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. Both properties are prominently situated on Pendleton Point Road, offering a mid-island location close to the library, public park and playground, island market, and post office.
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Home facts
- Year built:1887
- Listing ID #:1642620
- Updated:November 10, 2025 at 05:32 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:4
- Full bathrooms:2
- Half bathrooms:2
- Living area:4,962 sq. ft.
Heating and cooling
- Heating:Baseboard
Structure and exterior
- Year built:1887
- Building area:4,962 sq. ft.
- Lot area:3.7 Acres
Utilities
- Water:Private, Well
- Sewer:Private Sewer, Septic Design Available
Finances and disclosures
- Price:$850,000
- Price per sq. ft.:$171.3
- Tax amount:$4,640 (2026)
MREIS Multiple Listing Service™ system
Listing data is derived in whole or in part from the Maine IDX & is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2023 Maine Real Estate Information System, Inc. All Rights ReservedNew listings near 292 & 300 Main Road
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