Single Family Residence at 166 Keene Road, Winchester
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$479,900

166 Keene Road
Winchester, NH 03470
Listed by Jamie Smith · BHG Masiello Keene
Bedrooms
3
Bathrooms
1.5
Living area
N/A
Year built
1800

About this home

** OPEN HOUSE SATURDAY, JULY 25 FROM 10AM-12PM** 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.

Highlights

Waterfront

Property details

MLS
Prime MLS
MLS #
5092617
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
70
On market date
N/A
Stories
N/A
Total bathrooms
1.5
Garage spaces
N/A
Parking spaces
N/A
Lot size
4.3 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Winchester School
1.25 mi away · Grades -1-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
357
Student:teacher ratio
11.5:1
District
Winchester School District
Middle
Hinsdale Middle High School
5.91 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
127
Student:teacher ratio
9.8:1
District
Hinsdale School District
High
Hinsdale High School
5.91 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
140
Student:teacher ratio
8.2:1
District
Hinsdale School District

Walkability

Blended score for Winchester's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

14
Very car-dependent
out of 100
EPA National Walkability Index
3.8 / 20 -- Least walkable
Google Places amenity density
5 / 100
Restaurants & cafes0
Grocery stores0
Parks1
Schools0
Transit stops0
Pharmacies0

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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% / yr
$
/mo
Est. monthly payment
$3,040/mo
$95,980 down
$383,920 loan
Principal & interest$2,490
Property tax (est.)$400
Home insurance (est.)$150

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Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimeMLS. The information being provided is 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 07/24/26.