Single Family Residence at 27 Headlands Road, Winchester
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$715,000

27 Headlands Road
Winchester, NH 03470
Listed by Vincent Dolan · RE/MAX Town & Country
Bedrooms
2
Bathrooms
1.5
Living area
N/A
Year built
1992

About this home

Stunning Waterfront! Like new Cape style post and beam beauty with direct waterfront on Forest Lake. Gorgeous views from every window. Modern Kitchen with stainless appliances and center island. Cozy Living Room with gas Fireplace. The downstairs living area contains a Family Room, Kitchen, Bedroom and Bathroom. This is a perfect year-round retreat or possible short term rental. Also being offered as part of a portfolio of short-term rental properties.

Highlights

Waterfront

Property details

MLS
Prime MLS
MLS #
5045812
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
428
On market date
N/A
Stories
N/A
Total bathrooms
1.5
Garage spaces
N/A
Parking spaces
N/A
Lot size
0.16 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
1.62 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
6.96 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
6.96 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). EPA National Walkability Index only -- nearby-amenity data not cached yet for this area.

24
Car-dependent
out of 100
EPA National Walkability Index
4.8 / 20 -- Least walkable

Mortgage calculator

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Est. monthly payment
$4,456/mo
$143,000 down
$572,000 loan
Principal & interest$3,710
Property tax (est.)$596
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 07/27/26.