106 Old Military Rd

Winn, ME 04495

$99,000
Price
3
Beds
1,044 Sq. Ft.
$95 / Sq. Ft.
1,044
Sq. Ft.
$95
per Sq. Ft.
Get preapproved with Rocket Mortgage1

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.
  1. Listed by Alan Staples • Acres Away, Inc.
    P: (239)-398-0261 C: (239)-398-0261 astaples239@gmail.com
  2. Listed by Cole Staples • Acres Away, Inc.
    P: (207)-290-0725 C: (207)-290-0725 staples2ski@gmail.com

Property Details for 106 Old Military Road

Architectural Style
New Englander
Furnished
Unfurnished
View
Trees/Woods
Has Waterfront
No
Waterfront Features
Lake/Fresh Water, Nearby, River/Brook/Stream
Zoning
See Town
LISTING UPDATED: 05/15/2026 03:27 PM

Property Details for 106 Old Military Road

StatusActive
MLS #1661600
Days on Market45
Taxes$2,290 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1900
Lot Size0.43 AC / 18,730 SF
CountyPenobscot County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Acres Away, Inc.
Add your commute

Building Information for 106 Old Military Road

Stories-Year Built1900Building Size-Lot Size0.43 AC / 18,730 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$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.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 106 Old Military Road

Summary
Location and General Information
  • Page: 93
  • Latitude: 45.448852
  • Longitude: -$68.42
Taxes and HOA
  • Association: No
  • Parcel Number: WINN-000006-000000-000003
  • Tax Lot: 3
  • Tax Book Number: 16620
  • Tax Map Number: 6
  • Tax Year: 2025
  • Tax Annual Amount: $2,290.34
Parking
  • Has Attached Garage: No
  • Garage Spaces: 2.0
  • Has Garage: Yes
Property
Lot Information
  • Lot Features: Level, Open Lot
  • Lot Size Acres: 0.43
  • Lot Size Area: 0.43
  • Lot Size Source: Public Records
  • Lot Size Square Feet: 18730.8
  • Lot Size Units: Acres
  • Roads: Paved, Public
  • Road Surface Type: Paved
  • Site: Level, Open
Property and Assessments
  • Above Grade Finished Area: 1044.0
  • Building Area Source: Measured
  • Building Area Total: 1044.0
  • Property Sub Type: Single Family Residence
  • Restrictions: No Restrictions
  • Year Built: 1900
Building Features
  • Levels: Multi-Level
  • Foundation Details: Block
Financial Information
  • List Price/SqFt: $94.83
Utilities
  • Electric: Circuit Breakers
  • Gas: Bottled
  • Recreational Water: Lake/Fresh Water, Nearby, River/Brook/Stream
  • Sewer: Private Sewer
  • Water Source: Private, Well
Interior and Exterior Features
Exterior Features
  • Roof: Metal
Interior Features
  • Appliances: Gas Range, Refrigerator
  • Bathrooms Full: 1
  • Bathrooms Half: 1
  • Bathrooms Total Decimal: 1.5
  • Bathrooms Total Integer: 2
  • Bedrooms Total: 3
  • # Full Baths Level 1: 1
  • # Half Baths Level 2: 1
  • Rooms Total: 7
  • Basement: Bulkhead, Interior Entry, Full, Sump Pump, Unfinished
  • Has Fireplace: Yes
  • Has Cooling: No
  • Has Heating: Yes
  • Flooring: Carpet, Laminate, Wood
Room Information
Bedroom 1
  • Bedroom 1: Bedroom 1
  • Bedroom 1 Level: First
Bedroom 2
  • Bedroom 2: Bedroom 2
  • Bedroom 2 Level: Second
Bedroom 3
  • Bedroom 3: Bedroom 3
  • Bedroom 3 Level: Second
Dining Room
  • Dining Room: Dining Room
  • Dining Room Level: First
Kitchen
  • Kitchen: Kitchen
  • Kitchen Level: First
Living Room
  • Living Room: Living Room
  • Living Room Level: First
Office Room
  • Office: Office
  • Office Level: First
Rental
Rent Information
  • Land Lease: No
  • Pets Allowed: No Restrictions

Property History for 106 Old Military Road

DateEvent & SourcePriceAppreciation
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—
DateEvent & SourcePrice
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

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
Lee/Winn School
Public - PK to 4
Mt Jefferson Jr High School
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.

Similar Homes

Explore Nearby Homes

More information about 106 Old Military Road, Winn, ME 04495

106 Old Military Road is a single family home for sale in Winn, ME 04495. This property was listed for sale on May 11, 2026 by Acres Away, Inc., it's currently listed at $99,000. This listing's school district is Regional School Unit 30 Msad 30. Nearby schools include Lee/Winn School and Mt Jefferson Jr High School. 106 Old Military Road is a 3-bed, 2-bath, 1,044 sqft single family home built in 1900.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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.