Listed by HKS Associates, Inc. · Anna Schierioth · 603-352-6030
Single Family Residence · Winchester, NH
71 Headlands Road, Winchester, NH
$445,000
$495,000 · changed Jul 13, 2026
Est. $2,250/mo · 20% down, 30-yr, 6.5% (Owl’s Nest Real Estate estimate, not MLS data)
- Beds
- 3
- Baths
- 2
- Sq Ft
- 1,066
- Built
- 1928
- MLS®
- #5096976
Property Description
From its address at 71 Headlands Road, this single-family home puts you in Winchester, New Hampshire. On offer: 3 bedrooms, 2 bathrooms and 1,066 square feet of living space, at a list price of $445,000. The format is the classic one — a standalone home with no association between you and your plans for it. Beyond the basics, the listing carries a 0.39-acre lot, 1928 construction and roughly $417 per square foot. Browse the gallery and specs below; if it fits, we can have you through the door quickly.
This year-round lakefront retreat offers 100 feet of shoreline on Forest Lake and combines comfort, character, and stunning water views. Relax on the enclosed porch or one of several decks while enjoying the peaceful lakeside setting. The open-concept living and dining area features a pellet stove and abundant windows that capture beautiful lake views throughout the seasons. Outdoor living takes center stage, whether you're enjoying your morning coffee on the porch, entertaining on the decks, or spending the day on the water. A separate mobile home that has not been used for some time and could potentially serve as a guest cottage or private accommodation for family and visitors. It includes a living room, kitchen with pantry, bedroom, bathroom, attached shed, its own septic system, and a wood stove ready for hookup. Whether you're seeking a year-round residence, vacation getaway, or a property with space for extended family and guests, this unique waterfront offering provides the perfect blend of tranquility, recreation, and lakeside living.
Location Highlights
71 Headlands Road is a single family residence in Winchester, New Hampshire, listed at $445,000. That works out to about $417 per square foot, for a home built in 1928. It has been on the market for 4 months.
At this latitude, Winchester averages roughly 8.3 hours of sun a day in June and 3.6 in December.
Zoned schools: 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
- 2
- SqFt
- 1,066
- Price / SqFt
- $417.45
- Property Type
- Single Family Residence
- Year Built
- 1928
- County
- NH-Cheshire
- Town
- Winchester, NH
- Status
- Active
- Days on Market
- 116
Primary Features
- County
- NH-Cheshire
- Property Type
- Residential
- Year Built
- 1928
- Zoning
- LAKEFO
Interior Features
- Appliances
- Dryer, Electric Water Heater, Washer
- Basement
- No
- 1/4 Baths
- 0
- 3/4 Baths
- 0
- Cooling
- Wall Unit(s)
- Electric
- Circuit Breakers
- Flooring
- Carpet
- Heating
- Electric, Pellet Stove
- Interior Features
- 1 Fireplace, Natural Light
- Rooms - Total
- 7
- SqFt-Approximate Finished Above Grade
- 1,066
- SqFt-Approximate Finished Below Grade
- 0
- SqFt Approximate Total Finished
- 1,066
- SqFt Approximate Total
- 1,174
Location Information
- School - District
- Winchester School District
- School - Elementary
- Winchester School
- School - High
- KeeneHighS
- School - Middle/Jr
- Winchester School
Financial Details
- Cable Company
- Xfinity
- Tax - Gross Amount
- $7,482
- Tax Year
- 2025
- Taxes TBD
- No
Additional
- Construction Status
- Existing
- Construction
- Asbestos, Wood Frame, Shingle Siding
- Covenants
- Unknown
- Flood Zone
- Unknown
- Pre-Construction
- No
- Property Sub Type
- Single Family Residence
- Seasonal
- No
- Total Stories
- One
- Surveyed
- Unknown
- Timeshare/Fractional Ownership
- No
- Water Access Details
- Directly Adjoining
External Features
- Color
- Yellow
- Driveway
- Gravel
- Exterior Features
- Deck, Guest House, Natural Shade, Outbuilding, Enclosed Porch, Shed
- Foundation
- Concrete
- Garage
- No
- Lot Features
- Sloped, Wooded
- Lot - Acres
- 0.39
- Lot - SqFt
- 16,988
- Parking
- Permit Required
- Road Frontage Type
- Private Road
- Road Frontage
- Yes
- Road Frontage Length
- 88
- Roof
- Shingle
- Sewer
- Private
- Utilities
- Cable
- Water Source
- Public
- Water Body Type
- Lake
MLS®: PrimeMLS #5096976; Listed by HKS Associates, Inc. · Anna Schierioth · 603-352-6030
Property History
Estimated annual taxes for this property
- 2024
- $7,565
- 2023
- $7,376
- 2022
- $7,187
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
$2,973/ mo
- Principal & Interest
- $2,250
- Property Tax
- $630
- Home Insurance
- $93
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 71 Headlands Road, Winchester, NH
Assigned Schools
- Elementary
- Winchester School
- Middle
- Winchester School
- High School
- KeeneHighS
- District
- Winchester School District
Source: Google Maps Platform (Places) and Owl’s Nest Real Estate — not PrimeMLS data.
Questions About This Listing
How much does 71 Headlands Road cost?
71 Headlands Road in Winchester, NH is listed for $445,000 on PrimeMLS.
That is about $417 per square foot of finished living space.
It came on the market on June 26, 2026.
How many bedrooms and bathrooms does 71 Headlands Road have?
71 Headlands Road in Winchester, NH has 3 bedrooms and 2 bathrooms in 1,066 square feet of finished living space.
What is the lot size of 71 Headlands Road?
71 Headlands Road in Winchester, NH sits on 0.39 acres, per the MLS.
The lot is described as sloped and wooded.
It has 88 feet of road frontage (private road).
Zoning: LAKEFO.
What are the annual property taxes for 71 Headlands Road?
Annual property taxes on 71 Headlands Road in Winchester, NH are $7,482 for the 2025 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 71 Headlands Road have?
71 Headlands Road in Winchester, NH is heated by electric and pellet stove, per the MLS.
Cooling: wall unit(s).
What are the water and sewer systems at 71 Headlands Road?
71 Headlands Road in Winchester, NH has public water and a private septic system, per the MLS.
MLS details — water: public; sewer: private.
Electric: circuit breakers.
Other utilities: cable; cable provider Xfinity.
Plan a water test and septic inspection during your inspection period.
Does 71 Headlands Road have a basement?
No. The MLS lists no basement at 71 Headlands Road in Winchester, NH.
What are the key features of 71 Headlands Road?
Inside, the MLS lists these features at 71 Headlands Road in Winchester, NH: 1 fireplace and natural light.
Outside: deck, guest house, natural shade, outbuilding, enclosed porch and shed.
Flooring: carpet.
Listed appliances: dryer, electric water heater and washer; confirm which ones convey in the purchase agreement.
What parking does 71 Headlands Road have?
The MLS lists no garage at 71 Headlands Road in Winchester, NH; parking is off a gravel driveway.
Parking details: permit required.
Is 71 Headlands Road a waterfront property?
Yes. The MLS lists 71 Headlands Road in Winchester, NH as a waterfront property on a lake.
Water access: directly adjoining.
Confirm frontage, shoreland rules and any dock or beach rights during due diligence.
What school district is 71 Headlands Road in?
The MLS places 71 Headlands Road in Winchester, NH in the Winchester School District.
Listed schools: Winchester School (elementary), Winchester School (middle) and KeeneHighS (high).
School assignments can change; confirm with the district.
Is 71 Headlands Road still for sale?
Yes. 71 Headlands Road in Winchester, NH is listed as Active on PrimeMLS (MLS #5096976).
Status can change quickly; contact us to confirm availability before you visit.
Which brokerage has 71 Headlands Road listed?
71 Headlands Road in Winchester, NH is listed by Anna Schierioth of HKS Associates, Inc. (603-352-6030).
Owl's Nest Real Estate shows it through the PrimeMLS IDX feed; we are not the listing brokerage.
What type of home is 71 Headlands Road?
71 Headlands Road in Winchester, NH is a single-family home built in 1928.
The MLS lists its style as Bungalow, with one story.
What town is 71 Headlands Road in?
71 Headlands Road is in Winchester, New Hampshire 03470, in Cheshire County.
How does the price of 71 Headlands Road compare with other Winchester listings?
At $445,000, 71 Headlands Road in Winchester, NH is priced above 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 71 Headlands Road in person?
To see 71 Headlands 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.