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.
Active
$107,000
106 Old Military Road, Winn, ME 04495
3beds
1,044sqft
Est.:
Single Family Residence
Built in 1900
0.43 Acres Lot
$-- Zestimate®
$102/sqft
$-- HOA
What's special
Nearby garageLaundry roomDining roomBasement with extra-high ceilings
- 2 hours |
- 47 |
- 2 |
Zillow last checked:
Listing updated:
Listed by:
Acres Away, Inc.
Source: Maine Listings,MLS#: 1661600
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
Bedroom 1
- Level: First
Bedroom 2
- Level: Second
Bedroom 3
- Level: Second
Dining room
- Level: First
Kitchen
- Level: First
Living room
- Level: First
Office
- Level: First
Heating
- Direct Vent Heater, Forced Air, Wood Stove
Cooling
- None
Appliances
- Included: Gas Range, Refrigerator
Features
- Flooring: Carpet, Laminate, Wood
- Basement: Bulkhead,Interior Entry,Full,Sump Pump,Unfinished
- Number of fireplaces: 1
Interior area
- Total structure area: 1,044
- Total interior livable area: 1,044 sqft
- Finished area above ground: 1,044
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Paved, 1 - 4 Spaces
- Garage spaces: 2
Features
- Levels: Multi/Split
- Has view: Yes
- View description: Trees/Woods
Lot
- Size: 0.43 Acres
Details
- Zoning: See Town
Construction
Type & style
- Home type: SingleFamily
- Architectural style: New Englander
- Property subtype: Single Family Residence
Materials
- Wood Frame, Metal Clad, Shingle Siding, Wood Siding
- Foundation: Block
- Roof: Metal
Condition
- Year built: 1900
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: Private Sewer
- Water: Private, Well
Community & HOA
Location
- Region: Winn
Financial & listing details
- Price per square foot: $102/sqft
- Annual tax amount: $2,290
- Date on market: 5/11/2026
Estimated market value
Not available
Estimated sales range
Not available
$1,721/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/11/2026 | Listed for sale | $107,000+1.9%$102/sqft |
Source: | ||
| 3/9/2026 | Listing removed | $105,000$101/sqft |
Source: | ||
| 2/13/2026 | Listed for sale | $105,000-3.7%$101/sqft |
Source: | ||
| 2/2/2026 | Contingent | $109,000$104/sqft |
Source: | ||
| 9/16/2025 | Price change | $109,000-8.4%$104/sqft |
Source: | ||
| 9/9/2025 | Listed for sale | $119,000$114/sqft |
Source: | ||
Public tax history
Tax history is unavailable.
Climate risks
Neighborhood: 04495
Nearby schools
GreatSchools rating
- 5/10Lee/Winn SchoolGrades: PK-4Distance: 5.2 mi
- 5/10Mt Jefferson Jr High SchoolGrades: 5-8Distance: 8.9 mi
A local agent can set up tours, give advice and negotiate with sellers.
- Maine
- Penobscot County
- Winn
- 04495
- 106 Old Military Road





