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About the Listing 2766 - 020750
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.
Listing Highlights for 292300 292 & 300 Main Rd
Status
Active
Days on Site
5
Property Type
Residential
MLS ®
1642620
Year Built
1887
Total Square Footage
4,962
Lot/Acreage
3.7
County
Waldo
Interior Details
- Bedrooms: 5
- Bathrooms: 2 Full / 2 Half
- Appliances: Washer, Refrigerator, Microwave, Electric Range
- Air Cond:
- Heating: Baseboard
- Fireplaces: 1
- Floor:
- Above Ground Sq Ft: 4962
- Below Ground Sq Ft: 0
- Basement: Crawl Space,Partial,Bulkhead,Unfinished
- Other: 1st Floor Bedroom,Bathtub
- Water: Well,Private
Exterior Details
- Lot Description: Open,Level,Near Town
- Garage Capacity: N/A
- Zoning: Residential
- Roof:
- Others:
- Sewer: Septic Tank,Private Sewer,Septic Design Available
- Parking Features: 1 - 4 Spaces,5 - 10 Spaces,Gravel
Financial Details
- Tax Amount: $4,640
- Taxes w/Assessments: N/A
- Tax/Property ID: N/A
- Tax Year: 2026
Payment Calculator
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Listing Location
Questions About..
292300 292 & 300 Main Rd Islesboro, ME 04848
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