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...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.
- Listed by Alan Staples • Acres Away, Inc.
- Listed by Cole Staples • Acres Away, Inc.
Property Details for 106 Old Military Road
Waterfront
No
Waterfront FeaturesRiver/Brook/Stream, Nearby, Lake/Fresh Water
ArchitecturalStyleNew Englander
Garage Spaces2.00
GarageYes
ZoningSee Town
ViewTrees/Woods
LISTING UPDATED: 05/13/2026 07:38 AM
Property Details for 106 Old Military Road
| Status | Active |
|---|---|
| MLS # | 1661600 |
| Days on Market | 25 |
| Taxes | $2,290 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Single Family |
| MLS Type | Residential / Single Family Residence |
| Year Built | 1900 |
| Lot Size | 0.43 AC / 18,730 SF |
| County | Penobscot County |
Location
Listing Courtesy of Acres Away, Inc.
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Building Information for 106 Old Military Road
Stories-Year Built1900Building Size-Lot Size0.43 AC / 18,730 SF
Payment Calculator
$684 per month
30 year fixed, 6.36% Interest
Principal and Interest
$493
Property Taxes
$191
HOA Dues
$0
The Payment Calculator is for illustrative purposes only.
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1Property Information for 106 Old Military Road
Summary
Location and General Information
- Road Surface Type: Paved
- Zip Code: 5435
- Town: Winn
- State/Province: ME
- Zip Code: 04495
- County: Penobscot
- Geo Latitude: 45.448852
- Geo Longitude: -68.422985
- Tax Lot: 3
- Site:Level: Yes
- Site:Open: Yes
- Location:Rural: Yes
- Recreational Water:Lake/Fresh Water: Yes
- Recreational Water:Nearby: Yes
- Recreational Water:River/Brook/Stream: Yes
- Construction: Wood Frame
- Road Frontage: false
- Water View2: No
- Tree Growth YN2: false
Parking
- Parking Features: Paved, Detached, 1 - 4 Spaces
- Attached Garage: No
- Parking: 1 - 4 Spaces
Taxes and HOA Information
- Tax Book Number: 16620
- Tax Map Number: 6
- Tax Year: 2025
- Parcel Number: WINN-000006-000000-000003
- Location Information:Association Y/N: No
- Tax Annual Amount: $2,290.34
- Restrictions:No Restrictions: Yes
Property
Green Features
- HERS Certified: No
Heating and Cooling
- Water Heater:Gas: Yes
- Heat Fuel: Gas Bottled, Oil, Propane, Wood2
- Heat System: Direct Vent Heater, Forced Air, Wood Stove
Lot Information
- SqFt Finished Below Grade: 0.0
- SqFt Finished Above Grade: 1044.0
- Lot Size Acres: 0.43
- Source of Acreage: Public Records
- Building Area Total: 1044.0
- Lot Size Area: 0.43
- Lot Size Units: Acres
- Lot Size Square Feet: 18730.8
- Bedrooms Total: 3
- Bathrooms Full: 1
- Bathrooms Half: 1
- Street Number: 106
- Property Information:Surveyed: No
- Property Information:Seasonal: No
- Property Information:Short Sale Continue to Show: No
- Property Information:Deed/Conveyance Type Offered: Warranty
- Property Information:Deed: All
- Property Information:Bank Owned REO: No
- Property Information:2 Detached Houses on 1 Lot: No
- Property Information:# Rooms: 7.00
- Property Information:Total Half Baths: 1.00
- 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: .00
- Property Information:# Full Baths Level 2: .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:Paved: Yes
- Driveway: Paved2
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: Measured
- Year Built: 1900
Utilities
- Electric: Circuit Breakers
- Sewer: Private Sewer, Septic Tank
- Water Source: Private, Well
- Appliances Included:Gas Range: Yes
- Appliances Included:Refrigerator: Yes
- Gas:Bottled: Yes
- Water Heater: Gas
- Appliances: Refrigerator, Gas Range
Interior and Exterior Features
Exterior Features
- Construction Materials: Wood Frame, Metal Clad, Shingle Siding, Wood Siding
- # Fireplaces: 1
- Fireplace: Yes
- Vehicle Storage:2 Car: Yes
- Vehicle Storage:Detached: Yes
- Roof: Metal
- Vehicle Storage: 2 Car, Detached
- Basement Entry: Bulkhead2, Interior
Interior Features
- Basement: Bulkhead, Full, Sump Pump, Unfinished
- Flooring: Carpet, Laminate, Wood
- Interior Features: 1st Floor Bedroom
- Cooling: None
- Heating: Gas Bottled, Oil, Propane, Wood, Direct Vent Heater, Forced Air, Wood Stove
- Foundation Details: Block
- Laundry Features: Laundry - 1st Floor, Main Level
- Room Total: 7
- Bathrooms Total (Integer): 2
- Bathrooms Total (Decimal): 1.50
- Bathrooms Total (Notational): 1.10
- Cooling YN: No
- Heating YN: Yes
- Levels: Multi-Level
- Furnished: Unfurnished
- Amenities: 1st Floor Bedroom, Laundry - 1st Floor
Room Information
Room 1
- Room Type: Living Room
- Room Level: First
Room 2
- Room Type: Dining Room
- Room Level: First
Room 3
- Room Type: Kitchen
- Room Level: First
Room 4
- Room Type: Bedroom 1
- Room Level: First
Room 5
- Room Type: Bedroom 2
- Room Level: Second
Room 6
- Room Type: Bedroom 3
- Room Level: Second
Room 7
- Room Type: Office
- Room Level: First
Property History for 106 Old Military Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| May 13, 2026 | Price Change Maine Listings #1661600 | $99,000 | — |
| May 11, 2026 | Listed (Active) Maine Listings #1661600 | $107,000 | — |
| Mar 8, 2026 | Expired Maine Listings #1637003 | $105,000 | — |
| Feb 2, 2026 | Active Under Contract Maine Listings #1637003 | — | |
| Sep 16, 2025 | Price Change Maine Listings #1637003 | $109,000 | — |
| Sep 8, 2025 | Listed (Active) Maine Listings #1637003 | $119,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 05/13/2026 | Price Change Maine Listings #1661600 | $99,000 |
| 05/11/2026 | Listed (Active) Maine Listings #1661600 | $107,000 |
| 03/08/2026 | Expired Maine Listings #1637003 | $105,000 |
| 02/02/2026 | Active Under Contract Maine Listings #1637003 | — |
| 09/16/2025 | Price Change Maine Listings #1637003 | $109,000 |
| 09/08/2025 | Listed (Active) Maine Listings #1637003 | $119,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 106 Old Military Road
Taxable ValueLand$16,750Additions$82,830Total$99,580
Tax Record2023$1,892 ($158 / month)
Home Facts
Beds0Lot Size18,731 SqFtStyleSingle Family ResidenceCountyPENOBSCOTAPNWINN M:06 L:03
Schools near 106 Old Military Road
This home is within Regional School Unit 30 Msad 30.
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 4 | |||
| Public - | 5 to 8 |
Rating | School | Distance |
|---|---|---|
Lee/Winn School PublicPK to 4 | ||
Mt Jefferson Jr High School Public5 to 8 |
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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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.
Listing Courtesy of Acres Away, Inc.
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. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.
