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$99,000
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Property Description
Located in the quiet town of Winn, this well-maintained 3-bedroom, 1.5-bath home at 106 Old Military Road offers a comfortable layout and access to some of the area's best outdoor recreation. Set near the scenic Penobscot River, this location provides convenient opportunities for boating, fishing, canoeing, and kayaking, while also being close to ATV and snowmobile trail systems. Inside, the home features a functional and inviting floor plan. The first floor includes a kitchen, dining room, laundry room, a bedroom, and a full bath, offering the ease of single-level living if desired. The open-concept kitchen and living room area creates a welcoming space for gathering and everyday living. Upstairs, you'll find two additional bedrooms connected by a half bath, providing a practical setup for family or guests. The property sits on a nicely laid-out 0.43-acre lot with a pleasant mix of open space, ideal for enjoying the outdoors without extensive upkeep. A nearby garage offers excellent potential as a workshop, storage space, or hobby area, with plenty of room to suit a variety of needs. The home also features a basement with extra-high ceilings, adding even more usable space for storage or future possibilities. Numerous upgrades have been completed over the past few years, helping to enhance both comfort and efficiency. Whether you're looking for a primary residence or a place to enjoy Maine's four-season recreation--including hunting, fishing, trail riding, and more--this property is ready to fit a variety of lifestyles.
Full Property Details
Full Property Details for 106 Old Military Rd
General
- Price: $99,000
- Taxes: $2,290 (2025)
- Status: Active
- Type: Single Family
- Source: MREIS
- MLS ID: 1661600
- Updated: 6/4/2026
- Added to Site: 49 day(s) ago
Interior
- Number of Rooms: 7
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Gas Range, Refrigerator
- Furnishings: Unfurnished
- Flooring: Carpet, Laminate, Wood
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 1
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
Parking
- Garage: Yes
- Garage Spaces: 2
- Parking Features: Paved, 1 - 4 Spaces
Location
- County: Penobscot
Community
- Pets Allowed: Yes
Heating & Cooling
- Cooling Type: None
- Heating Type: Gas Bottled, Oil, Propane, Wood, Direct Vent Heater, Forced Air, Wood Stove
Utilities
- Sewer: Private Sewer
- Water: Private, Well
- Well: Yes
Structural Information
- Architectural Style: New Englander
- Construction: Wood Frame, Metal Clad, Shingle Siding, Wood Siding
- Basement: Yes
- Basement Desc.: Bulkhead, Interior Entry, Full, Sump Pump, Unfinished
- Roof: Metal
- Square Feet: 1,044
- Sq. Ft. Source: Measured
- Finished Total: 1,044 Sq. Ft.
- Finished Above Grnd: 1,044 Sq. Ft.
- Year Built: 1900
Lot Features
- Property View: Trees/Woods
- Lot Size (Acres): 0.43
- Lot Size (Sq. Ft.): 18,730.8
- Zoning: See Town
- Lot Description: Level, Open Lot
Financial Considerations
- Tax Amount: $2,290.34
- Tax Year: 2025
Disclosures and Reports
- Lot Number: 3
Listed by Acres Away, Inc. (207) 794-2700
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Schools
Schools serving 106 Old Military Rd
School District:School Administrative District 30
| Name | Grades | Distance |
|---|---|---|
Mt Jefferson Jr High School 61 Winn Road, Lee, ME 04455 | 5-8 | 8.9 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 106 Old Military Rd
Date
Details
Price
Change
Source
5/13/2026
Price Reduced
$99,000
-7.48%
MLS
5/11/2026
Listed
$107,000
24.42%
MLS
9/14/2022
Sold
$86,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 106 Old Military Rd
Year
Property Taxes
Change
Tax Assessment
Change
2023
$1,892
3%
$99,580
—
2022
$1,836
—
$99,250
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 106 Old Military Rd
106 Old Military Road, Winn, ME 04495 (MLS# 1661600) is a Single Family property with 3 bedrooms, 1 full bathroom and 1 partial bathroom. 106 Old Military Road is currently listed for $99,000 and was received on May 11, 2026. Want to learn more about 106 Old Military Road? Do you have questions about finding other Single Family real estate for sale in Winn? You can browse all Winn real estate or contact a Coldwell Banker agent to request more information.

