Welcome to 166 Keene Road in Winchester, a charming 3-bedroom, 1.5-bath New Englander that combines classic character with thoughtful modern updates. This inviting home offers comfortable living spaces, abundant natural light, and a warm atmosphere that immediately feels like home. Recent improvements include an updated roof, solar panels for enhanced energy efficiency, a spacious back deck ideal for entertaining and outdoor enjoyment, fresh paint throughout the interior, updated light fixtures, and a new dishwasher, allowing the next owner to move in with confidence. The functional floor plan provides flexibility for everyday living, whether you're gathering with family, working from home, or hosting friends. Outside, enjoy the benefits of outdoor living from the rear deck or wrap around front porch, perfect for summer barbecues, morning coffee, or simply relaxing while taking in the surroundings. The solar system helps reduce energy costs while adding long-term value and sustainability. 465' of frontage on Ashuelot River. Conveniently located with easy access to local amenities, schools, shopping, dining, and recreational opportunities, this property offers the perfect balance of small-town New Hampshire living and modern convenience. Easy commute to Keene, Mass, Brattleboro and Interstate 91.
Active
Listed by: BHG Masiello Keene • Jamie Smith
Price cut: $30K (8/31)
$449,900
166 Keene Road, Winchester, NH 03470
3beds
1,808sqft
Single Family Residence
Built in 1800
4.3 Acres Lot
$-- Zestimate®
$249/sqft
$-- HOA
What's special
New dishwasherUpdated roofAbundant natural lightComfortable living spacesUpdated light fixturesWarm atmosphere
- 101 days
- 1,820
- 130
Zillow last checked:
Listing updated:
Listed by:
Jamie Smith,
BHG Masiello Keene 603-352-5433
Source: PrimeMLS,MLS#: 5092617
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
Heating
- Hot Water, Mini Split, Boiler
Cooling
- Mini Split
Appliances
- Included: Dishwasher, Dryer, Double Oven, Refrigerator, Washer, Oil Water Heater, Instant Hot Water
- Laundry: In Basement
Features
- Cathedral Ceiling(s), Ceiling Fan(s), Dining Area, Natural Light
- Flooring: Hardwood, Tile
- Basement: Concrete Floor,Full,Unfinished,Interior Access,Interior Entry
Interior area
- Total structure area: 2,712
- Total interior livable area: 1,808 sqft
- Finished area above ground: 1,808
- Finished area below ground: 0
Property
Parking
- Parking features: Gravel
Features
- Levels: Two
- Stories: 2
- Patio & porch: Porch
- Exterior features: Deck
- On waterfront: Yes
- Body of water: Ashuelot River
- Frontage length: Water frontage: 465,Road frontage: 484
Lot
- Size: 4.3 Acres
- Features: Country Setting, Level, Sloped, Wooded
Details
- Additional structures: Barn(s)
- Parcel number: WNCHM00030B000018L000000
- Zoning description: CENTRA
Construction
Type & style
- Home type: SingleFamily
- Architectural style: New Englander
- Property subtype: Single Family Residence
Materials
- Wood Frame, Clapboard Exterior, Wood Siding
- Foundation: Stone
- Roof: Asphalt Shingle
Condition
- New construction: No
- Year built: 1800
Utilities & green energy
- Electric: 200+ Amp Service, Circuit Breakers
- Sewer: Public Sewer
- Utilities for property: Cable
Community & HOA
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $249/sqft
- Tax assessed value: $187,200
- Annual tax amount: $6,330
- Date on market: 6/3/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 8/31/2026 | Price change | $449,900-6.3%$249/sqft |
Source:  PrimeMLS #5092617 Report a problem | ||
| 7/19/2026 | Price change | $479,900-4%$265/sqft |
Source: PrimeMLS #5092617 Report a problem | ||
| 6/3/2026 | Listed for sale | $499,900+170.2%$276/sqft |
Source: PrimeMLS #5092617 Report a problem | ||
| 4/28/2020 | Sold | $185,000+236.4%$102/sqft |
Source: Public Record Report a problem | ||
| 5/1/2011 | Listing removed | $55,000$30/sqft |
Source: Galloway Real Estate LLC #4054501 Report a problem | ||
| 4/29/2011 | Listed for sale | $55,000$30/sqft |
Source: Galloway Real Estate LLC #4054501 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $5,476 +0% | $187,200 +8.3% |
| 2023 | $5,474 +10.4% | $172,800 |
| 2022 | $4,959 -0.2% | $172,800 |
| 2021 | $4,971 | $172,800 |
| 2020 | $4,971 -7.3% | $172,800 +14.9% |
| 2019 | $5,360 +2.6% | $150,400 |
| 2018 | $5,223 +7.7% | $150,400 -5.3% |
| 2016 | $4,848 -2.3% | $158,800 -2.1% |
| 2015 | $4,960 -8.8% | $162,200 -8.8% |
| 2014 | $5,437 -0.5% | $177,800 |
| 2013 | $5,464 +10.1% | $177,800 |
| 2012 | $4,964 -7% | $177,800 |
| 2011 | $5,339 +3.2% | $177,800 -7.4% |
| 2009 | $5,175 -4.7% | $192,100 |
| 2008 | $5,431 +15% | $192,100 +11.4% |
| 2007 | $4,724 | $172,400 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 03470
Nearby schools
Schools provided by the listing agent
- Elementary: Winchester School
- Middle: Winchester School
- High: Keene High School
- District: Keene Sch Dst SAU #29
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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