Listed by BHG Masiello Keene · Jamie Smith · 603-352-5433
Single Family Residence · Winchester, NH
166 Keene Road, Winchester, NH
$419,900
$429,900 · changed Oct 20, 2026
Est. $2,123/mo · 20% down, 30-yr, 6.5% (Owl’s Nest Real Estate estimate, not MLS data)
- Beds
- 3
- Baths
- 2
- Sq Ft
- 1,808
- Built
- 1800
- MLS®
- #5092617
Property Description
Welcome to 166 Keene Road, a single-family home in Winchester, New Hampshire. The home offers 3 bedrooms, 2 bathrooms and 1,808 square feet of living space, listed at $419,900. Single-family ownership here means your own land, your own walls and room to make the property yours. The numbers worth knowing: a 4.3-acre lot, 1800 construction and roughly $232 per square foot. See the listing's full details below, and reach out for a private showing of 166 Keene Road.
Seller contribution of $10,000 towards interest rate buydown. 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.
Location Highlights
166 Keene Road is a single family residence in Winchester, New Hampshire, listed at $419,900. That works out to about $232 per square foot, for a home built in 1800. It has been on the market for 5 months.
At this latitude, Winchester averages roughly 8.3 hours of sun a day in June and 3.6 in December.
Zoned schools in the Keene Sch Dst SAU #29: Winchester School (Elementary), Winchester School (Middle), KeeneHighS (High). Always confirm zoning with the district office.
Source: zoned school names are PrimeMLS listing data; distances, sun exposure and school facts are Owl’s Nest Real Estate additions (school facts from the NCES, U.S. Department of Education) — not PrimeMLS data.
Property Details
Essentials & finishes
- Bedrooms
- 3
- Total Baths
- 2
- Full Baths
- 1
- SqFt
- 1,808
- Price / SqFt
- $232.25
- Property Type
- Single Family Residence
- Year Built
- 1800
- County
- NH-Cheshire
- Town
- Winchester, NH
- Status
- Active
- Days on Market
- 145
Primary Features
- County
- NH-Cheshire
- Property Type
- Residential
- Year Built
- 1800
- Zoning
- CENTRA
Interior Features
- Appliances
- Dishwasher, Dryer, Double Oven, Refrigerator, Oil Water Heater, On Demand Water Heater, Washer
- Basement
- Yes
- Basement Access Type
- Interior
- Basement Description
- Concrete Floor, Full, Interior Entry, Unfinished
- 1/4 Baths
- 0
- 3/4 Baths
- 0
- Cooling
- Mini Split
- Electric
- 200+ Amp Service, Circuit Breakers
- Flooring
- Hardwood, Tile
- Heating
- Boiler, Hot Water, Mini Split
- Interior Features
- Cathedral Ceiling(s), Ceiling Fan(s), Dining Area, Natural Light, Basement Laundry
- Rooms - Total
- 5
- SqFt-Approximate Finished Above Grade
- 1,808
- SqFt-Approximate Finished Below Grade
- 0
- SqFt Approximate Total Finished
- 1,808
- SqFt Approximate Total
- 2,712
Location Information
- School - District
- Keene Sch Dst SAU #29
- School - Elementary
- Winchester School
- School - High
- KeeneHighS
- School - Middle/Jr
- Winchester School
Financial Details
- Tax - Gross Amount
- $6,330
- Tax Year
- 2026
- Taxes TBD
- No
Additional
- Construction Status
- Existing
- Construction
- Clapboard, Wood Frame, Wood Siding
- Covenants
- No
- Easements
- Yes
- Flood Zone
- No
- Pre-Construction
- No
- Property Sub Type
- Single Family Residence
- Resort
- No
- Seasonal
- No
- Total Stories
- Two
- Surveyed
- No
- Timeshare/Fractional Ownership
- No
- Water Access Details
- Shared-Private
External Features
- Color
- Blue
- Driveway
- Gravel
- Exterior Features
- Barn, Deck, Porch
- Foundation
- Stone
- Garage
- No
- Lot Features
- Country Setting, Level, Sloped, Wooded
- Lot - Acres
- 4.3
- Lot - SqFt
- 187,308
- Road Frontage Type
- Public Maintained Road
- Road Frontage
- Yes
- Road Frontage Length
- 484
- Roof
- Asphalt Shingle
- Sewer
- Public
- Utilities
- Cable
- Water Source
- Public
- Water Body Type
- River
MLS®: PrimeMLS #5092617; Listed by BHG Masiello Keene · Jamie Smith · 603-352-5433
Property History
Estimated annual taxes for this property
- 2024
- $7,138
- 2023
- $6,960
- 2022
- $6,781
Source: Owl’s Nest Real Estate estimate from the list price at New Hampshire’s average effective tax rate — not PrimeMLS or town assessor data. Verify with the town assessor.
Market Data
Live snapshot computed by Owl’s Nest Real Estate from PrimeMLS IDX active listings in this town
- Active listings in Winchester
- 26
- Average list price
- $384,058
- Price range
- $20,000 – $699,000
Mortgage Calculator
Estimate your monthly payment for this home
Estimated Monthly Payment
$2,806/ mo
- Principal & Interest
- $2,123
- Property Tax
- $595
- Home Insurance
- $87
Source: Owl’s Nest Real Estate estimate, not PrimeMLS data. Estimates use typical New Hampshire costs — a 1.7% effective property-tax rate, insurance at 0.25% of home value/yr, and PMI below 20% down. Actual town tax rates vary; verify with your lender and the town assessor.
Around This Property
Schools, everyday places and nearby destinations near 166 Keene Road, Winchester, NH
Assigned Schools
- Elementary
- Winchester School
- Middle
- Winchester School
- High School
- KeeneHighS
- District
- Keene Sch Dst SAU #29
Source: Google Maps Platform (Places) and Owl’s Nest Real Estate — not PrimeMLS data.
Questions About This Listing
How much does 166 Keene Road cost?
166 Keene Road in Winchester, NH is listed for $419,900 on PrimeMLS.
That is about $232 per square foot of finished living space.
It came on the market on June 3, 2026.
How many bedrooms and bathrooms does 166 Keene Road have?
166 Keene Road in Winchester, NH has 3 bedrooms and 2 bathrooms (1 full and 1 half) in 1,808 square feet of finished living space.
What type of home is 166 Keene Road?
166 Keene Road in Winchester, NH is a single-family home built in 1800.
The MLS lists its style as New Englander, with two stories.
What town is 166 Keene Road in?
166 Keene Road is in Winchester, New Hampshire 03470, in Cheshire County.
What is the lot size of 166 Keene Road?
166 Keene Road in Winchester, NH sits on 4.3 acres, per the MLS.
The lot is described as country setting, level, sloped and wooded.
It has 484 feet of road frontage (public maintained road).
Zoning: CENTRA.
The MLS lists it as outside a flood zone.
The MLS notes easements; review them in the deed and title work.
What are the annual property taxes for 166 Keene Road?
Annual property taxes on 166 Keene Road in Winchester, NH are $6,330 for the 2026 tax year, per the MLS.
New Hampshire towns set their own tax rates and revalue periodically, so confirm the current bill with the Winchester assessing office.
What heating and cooling does 166 Keene Road have?
166 Keene Road in Winchester, NH is heated by boiler, hot water and mini split, per the MLS.
Cooling: mini split.
What are the water and sewer systems at 166 Keene Road?
166 Keene Road in Winchester, NH has public water and public sewer, per the MLS.
MLS details — water: public; sewer: public.
Electric: 200+ amp service and circuit breakers.
Other utilities: cable.
Does 166 Keene Road have a basement?
Yes. 166 Keene Road in Winchester, NH has a basement with interior access.
The MLS describes it as concrete floor, full, interior entry and unfinished.
What are the key features of 166 Keene Road?
Inside, the MLS lists these features at 166 Keene Road in Winchester, NH: cathedral ceiling(s), ceiling fan(s), dining area, natural light and basement laundry.
Outside: barn, deck and porch.
Flooring: hardwood and tile.
Listed appliances: dishwasher, dryer, double oven, refrigerator, oil water heater, on demand water heater and washer; confirm which ones convey in the purchase agreement.
What parking does 166 Keene Road have?
The MLS lists no garage at 166 Keene Road in Winchester, NH; parking is off a gravel driveway.
Is 166 Keene Road a waterfront property?
Yes. The MLS lists 166 Keene Road in Winchester, NH as a waterfront property on a river.
Water access: shared-private.
Confirm frontage, shoreland rules and any dock or beach rights during due diligence.
What school district is 166 Keene Road in?
The MLS places 166 Keene Road in Winchester, NH in the Keene Sch Dst SAU #29.
Listed schools: Winchester School (elementary), Winchester School (middle) and KeeneHighS (high).
School assignments can change; confirm with the district.
Is 166 Keene Road still for sale?
Yes. 166 Keene Road in Winchester, NH is listed as Active on PrimeMLS (MLS #5092617).
Status can change quickly; contact us to confirm availability before you visit.
Which brokerage has 166 Keene Road listed?
166 Keene Road in Winchester, NH is listed by Jamie Smith of BHG Masiello Keene (603-352-5433).
Owl's Nest Real Estate shows it through the PrimeMLS IDX feed; we are not the listing brokerage.
How does the price of 166 Keene Road compare with other Winchester listings?
At $419,900, 166 Keene Road in Winchester, NH is priced close to the $409,900 median asking price of the 14 single-family homes for sale in Winchester on PrimeMLS as of November 3, 2026 (this listing included).
That figure is Owl's Nest Real Estate's analysis of active listings, and asking prices are not sale prices — ask us for recent comparable sales before you make an offer.
How can I see 166 Keene Road in person?
To see 166 Keene Road in Winchester, NH, use Request a Showing on this page or call Owl's Nest Real Estate at 401-648-5308.
We can show any MLS-listed home and represent you as your buyer's agent; the listing brokerage represents the seller.
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NOTE: This representation is based in whole or in part on data generated by PrimeMLS, Inc., which assumes no responsibility for its accuracy. The data relating to real estate displayed on this site comes in part from the IDX Program of PrimeMLS.
This listing data is intended for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 11/03/26.