292-300 Main Rd
$850,000
Price
5
Beds
4
Baths
4,962 Sq. Ft.
$171 / Sq. Ft.
4,962
Sq. Ft.
$171
per Sq. Ft.
Description
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...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, offering a mid-island location close to the library, public park and playground, island market, and post office.
- Listed by Virginia Hess • Cates Real Estate • info@catesre.com
Property Details for 292-300 Main Road
Waterfront
No
ArchitecturalStyleFederal, New Englander
Garage Spaces.00
GarageNo
ZoningResidential
ViewScenic, Trees/Woods
LISTING UPDATED: 12/02/2025 09:30 AM
Property Details for 292-300 Main Road
| Status | Active |
|---|---|
| MLS # | 1642620 |
| Days on Market | 52 |
| Taxes | $4,640 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Compass Type | Single Family |
| MLS Type | Residential / Single Family Residence |
| Year Built | 1887 |
| Lot Size | 3.70 AC / 161,172 SF |
| County | Waldo County |
Location
Listing Courtesy of Cates Real Estate
Add your commute
Building Information for 292-300 Main Road
Stories-Year Built1887Building Size-Lot Size3.70 AC / 161,172 SF
Payment Calculator
$4,587 per month
30 year fixed, 6.28% Interest
Principal and Interest
$4,200
Property Taxes
$387
HOA Dues
$0
The Payment Calculator is for illustrative purposes only.
Property Information for 292-300 Main Road
Summary
Location and General Information
- Road Surface Type: Paved
- Water Body Name: East Penobscot Bay
- Zip Code: 4509
- Directions: GPS directions are correct.
- Town: Islesboro
- State/Province: ME
- Zip Code: 04848
- County: Waldo
- Geo Latitude: 44.302326
- Geo Longitude: -68.902335
- Tax Lot: 11
- Site:Level: Yes
- Site:Open: Yes
- Location:Near Town: Yes
- Recreational Water:Nearby: Yes
Parking
- Parking Features: 1 - 4 Spaces, 5 - 10 Spaces, Gravel
- Attached Garage: No
Taxes and HOA Information
- Tax Book Number: 2575
- Tax Map Number: 19
- Tax Year: 2026
- Parcel Number: ISBR-000019-000000-000011
- Location Information:Association Y/N: No
- Tax Annual Amount: $4,640.00
Property
Heating and Cooling
- Water Heater:Electric: Yes
Lot Information
- SqFt Finished Below Grade: 0.0
- SqFt Finished Above Grade: 4962.0
- Lot Size Acres: 3.7
- Source of Acreage: Public Records
- Building Area Total: 4962.0
- Lot Size Area: 3.7
- Lot Size Units: Acres
- Lot Size Square Feet: 161172.0
- Bedrooms Total: 5
- Bathrooms Full: 2
- Bathrooms Half: 2
- Street Number: 292300
- Property Information:Surveyed: Yes
- Property Information:Seasonal: Yes
- Property Information:Deed: All
- Property Information:2 Detached Houses on 1 Lot: Yes
- Property Information:# Rooms: 12.00
- Property Information:Total Half Baths: 2.00
- Property Information:Color: White
- Property Information:# Full Baths Basement: .00
- Property Information:# Half Baths Basement: .00
- Property Information:# Full Baths Level 1: 1.00
- Property Information:# Half Baths Level 1: 1.00
- Property Information:# Full Baths Level 2: 1.00
- Property Information:# Half Baths Level 2: 1.00
- Property Information:# Full Baths Level 3: .00
- Property Information:# Half Baths Level 3: .00
- Property Information:# Full Baths Upper: .00
- Property Information:# Half Baths Upper: .00
Parking
- Driveway:Gravel: Yes
Property and Assessments
- Sign on Property: Yes
- Leased Land: No
- Property Type: Residential,Single Family Residence
- Property Type Label: Residential
- Property Sub-Type: Single Family Residence
- Building Area Source: Seller
- Year Built: 1887
Utilities
- Electric: True
- Sewer: Septic Tank, Private Sewer, Septic Design Available
- Water Source: Well, Private
- Appliances Included:Electric Range: Yes
- Appliances Included:Microwave: Yes
- Appliances Included:Refrigerator: Yes
- Appliances Included:Washer: Yes
- Gas:Bottled: Yes
Interior and Exterior Features
Exterior Features
- Construction Materials: Clapboard, Wood Frame
- # Fireplaces: 1
- Fireplace: Yes
- Vehicle Storage:No Vehicle Storage: Yes
- Other Structures: Outbuilding, Shed(s)
- Patio and Porch Features:Porch: Yes
Interior Features
- Basement: Crawl Space, Partial, Bulkhead, Unfinished
- Flooring: Wood, Laminate, Carpet
- Interior Features: 1st Floor Bedroom, Bathtub
- Cooling: None
- Heating: Baseboard
- Foundation Details: Stone, Granite
- Laundry Features: Laundry - 1st Floor, Main Level
- Room Total: 12
- Bathrooms Total (Integer): 4
- Bathrooms Total (Decimal): 3.00
- Bathrooms Total (Notational): 2.20
- Cooling YN: No
- Heating YN: Yes
- Kitchen Countertop:Formica: Yes
- Kitchen Countertop:Granite: Yes
Room Information
Room 1
- Room Type: Kitchen
- Room Level: First
Room 2
- Room Type: Dining Room
- Room Level: First
Room 3
- Room Type: Den
- Room Level: First
Room 4
- Room Type: Living Room
- Room Level: First
Room 5
- Room Type: Bedroom 1
- Room Level: Second
Room 6
- Room Type: Bedroom 2
- Room Level: Second
Room 7
- Room Type: Bedroom 3
- Room Level: Second
Room 8
- Room Type: Bedroom 4
- Room Level: Second
Room 9
- Room Type: Bedroom 5
- Room Level: Second
Room 10
- Room Type: Other Room
- Room Level: First
Room 11
- Room Type: Other Room 2
- Room Level: First
Room 12
- Room Type: In-law Floorplan
- Room Level: Second
Property History for 292-300 Main Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Oct 31, 2025 | Listed (Active) Maine Listings #1642620 | $850,000 | — |
| Aug 20, 2025 | Expired Maine Listings #1602042 | $850,000 | — |
| Aug 20, 2025 | Expired Maine Listings #1601765 | $850,000 | — |
| Aug 20, 2024 | Listed (Active) Maine Listings #1602042 | $850,000 | — |
| Aug 20, 2024 | Listed (Active) Maine Listings #1601765 | $850,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 10/31/2025 | Listed (Active) Maine Listings #1642620 | $850,000 |
| 08/20/2025 | Expired Maine Listings #1602042 | $850,000 |
| 08/20/2025 | Expired Maine Listings #1601765 | $850,000 |
| 08/20/2024 | Listed (Active) Maine Listings #1602042 | $850,000 |
| 08/20/2024 | Listed (Active) Maine Listings #1601765 | $850,000 |
For completeness, Compass often displays two records for one sale: the MLS record and the public record.
Schools near 292-300 Main Road
This home is within Islesboro Public Schools.
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | K to 12 |
Rating | School | Distance |
|---|---|---|
Islesboro Central School PublicK to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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Listing Courtesy of Cates Real Estate
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. © 2022 Maine Real Estate Information System, Inc. All Rights Reserved.
