27 Headlands Road, Winchester, NH
Single Family Residence
Listed by RE/MAX Town & Country · Vincent Dolan
Property Description
Buyers searching Winchester, New Hampshire will want a look at 27 Headlands Road — a single-family home asking $715,000. It features 2 bedrooms, 2 bathrooms and 973 square feet of living space. Homes like this trade on the fundamentals: space, privacy and a New Hampshire address that works year-round. Also on the sheet: 1992 construction and roughly $735 per square foot. Everything below — photos, details, schools and market data — updates live from the MLS.
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.
Location Highlights
27 Headlands Road is a single family residence in Winchester, New Hampshire, listed at $715,000. That works out to about $735 per square foot, for a home built in 1992. It has been on the market for 15 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 Winchester: Winchester School (Elementary). Always confirm zoning with the district office.
Property Details
Essentials & finishes
- Bedrooms:2
- Total Baths:2
- Full Baths:1
- SqFt:973
- Price / SqFt:$734.84
- Property Type:Single Family Residence
- Year Built:1992
- County:NH-Cheshire
- Town:Winchester, NH
- Status:Active
- Days on Market:463
Primary Features
Interior Features
Location Information
Financial Details
Additional
External Features
Property History
Annual taxes for this property
| Year | Assessed Tax |
|---|---|
| 2024 | $12,155 |
| 2023 | $11,851 |
| 2022 | $11,547 |
Estimated from list price; verify with the town assessor.
Market Data
Live snapshot computed from active listings in this town
- Active listings in Winchester21
- Average list price$648,483
- Price range$48,000 – $3,995,000
Mortgage Calculator
Estimate your monthly payment for this home
- Principal & Interest$3,615
- Property Tax$1,013
- Home Insurance$149
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 27 Headlands Road, Winchester, NH
Questions About This Listing
What is the MLS number for 27 Headlands Road?
The MLS number is #5045812 (PrimeMLS), listed on June 11, 2025.
What is the asking price of 27 Headlands Road?
27 Headlands Road in Winchester, NH is listed at $715,000.
That works out to about $735 per square foot.
What kind of property is 27 Headlands Road?
Single-family home in Winchester, New Hampshire, built in 1992.
How big is 27 Headlands Road?
The home has 2 bedrooms and 2 bathrooms.
It offers 973 square feet of living space.
Where is 27 Headlands Road located?
The property is in Winchester, New Hampshire (03470).
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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.
Considering this property as a short-term rental?