Single Family Residence at 152 Old Chesterfield Road, Winchester
Single Family Residence at 152 Old Chesterfield Road, Winchester, photo 2 of 31
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31 photos

$425,000

Under contract
152 Old Chesterfield Road
Winchester, NH 03470
Listed by Edith Fifield · BHG Masiello Keene
Bedrooms
1
Bathrooms
N/A
Living area
N/A
Year built
2007

About this home

2007 EXPANDABLE CAPE! A lovely, lovely home to begin with, plus the entire 2nd floor open to expansion, already plumbed and wired with layout for 2BR's and full bath with full shed dormer. On 7.5 acres with privacy and views to distant hills, you will not want to leave this serene home. It is a sanctuary. Plenty of wildlife viewing in your front yard. Inside is a welcoming single level layout with 2 baths, open concept LR/DR/KIT area and a main bedroom with walk-in closet. Hickory cabinetry in the cooks kitchen with a Viking gas range anchoring the space is ready for all your cooking adventures. A walk-in pantry makes meal prep easy and has plenty of room for canned goods and your seldom used appliances. The full basement is high and dry with ample room for workshop, family room or storage. There really is nothing not to like about this home! Close to state park, snow mobile and walking trails.

Property details

MLS
Prime MLS
MLS #
5093714
Property type
Single Family Residence
Subdivision
N/A
Status
Under contract
Days on market
7
On market date
N/A
Stories
N/A
Total bathrooms
N/A
Garage spaces
N/A
Parking spaces
N/A
Lot size
7.53 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
2.06 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
4.84 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
4.84 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

Market position

How this listing compares to current activity in Winchester, from live MLS data.

On the market 7 days -- 158 fewer days than Winchester's current average of 165 days.
For reference, the median list price across 34 active listings in Winchester right now is $272,450.

Mortgage calculator

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

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Est. monthly payment
$2,709/mo
$85,000 down
$340,000 loan
Principal & interest$2,205
Property tax (est.)$354
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 06/19/26.