Single Family for Sale: 39 Headlands Road, Winchester, NH 03470

3 beds
1 full, 1 three quarter baths
1,364 sqft
$698,000
$698,000
39 Headlands Road, Winchester, NH 03470
3 beds
1 full, 1 three quarter baths
1,364 sqft
$698,000
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Price:
$698,000

Type Single Family
Style Historic Vintage, Modified, Cape
Beds 3
Baths 1 full, 1 three quarter baths
Square Feet 1,364 sqft
Lot Size 0.36 acres
Year Built 1910
Taxes Paid $11,479

City Winchester
County Cheshire
School District Winchester

MLS 5087379
Status Active
DOM 41 days
Step across the threshold and into a piece of history. A 1910 waterfront hidden treasure. Timeless architectural details and unparalleled views of Forest Lake make this home a rare blend of old world elegance and modern comfort amidst perennial gardens, stone sculptures and lush greenery A timeless stone fireplace with charming nooks & crannies in the spacious living room echoes the style of simpler times while offering an updated kitchen, two first floor bedrooms and a newer sun-filled master suite with barn-door entrance and lake views ... you'll feel apart from the busy world at this lakeside retreat. There is extended living space outdoors on a spacious and private wooden deck featuring a screened room overlooking the lake as well as a hot/cold outdoor shower! The stairway to your private dock has several landings. A small barn with loft offers plenty of storage or workshop space. There's also a garden shed for more storage. A perfect property for discerning buyers seeking a piece of history combined with unparalleled waterfront view and timeless elegance. Don't miss this opportunity!

Lot & Building Features

Appliances Tank Water Heater, Owned Water Heater, Electric Water Heater, Gas Range, Microwave, Refrigerator
Features Interior Wood Stove Insert, Wood Fireplace, Natural Woodwork, Laundry Hook-ups, Ceiling Fan, Primary BR w/ BA, 1st Floor Laundry
Utilities Cable at Site
Construction Vertical Siding, Wood Exterior, Wood Siding, Wood Frame
Cooling Mini Split, Central AC
Heating Wood, Electric, Forced Air, Propane
Parking Description Carport, Covered, Driveway
Sewer Holding Tank, Concrete, 1000 Gallon, Leach Field, Private
Tax Year 2025
Taxes Paid $11,479
Water Public
Basement Description Gravel, Dirt, Partial, Crawl Space, Walkout
Foundation Pier/Column, Block, Stone
Lot Description Lake Frontage, Lake View, Waterfront, View, Sloping, Mountain View, Wooded, Landscaped, Country Setting
Roof Metal
Features Exterior Private Dock, Screened Porch, Barn, Outbuilding, Natural Shade, Covered Porch, Garden Space, Deck
Total Rooms 7
Garage No
Full Baths 1
3/4 Baths 1
Half Baths 0

Community and Schools

Elementary School Winchester School
Junior High School Winchester School
Senior High School Keene High School

Price History of 39 Headlands Road, Winchester, NH

Date Name Price Difference
05/06/2026 Listing Price $698,000 N/A
*Information provided by REWS for your reference only. The accuracy of this information cannot be verified and is not guaranteed.

Map of 39 Headlands Road, Winchester, NH

Location Map Street View
Photo of The Patey Team
Direct: 603-548-6392
Office
PO Box 316
Raymond, NH 03077
603-548-6392
Listed by BHG Masiello Keene, Nancy Panza 603-352-5433
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1.6445558739255%
6.75%
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39 Headlands Road (MLS #5087379) is a historic vintage, modified, cape single family home located in Winchester, NH. This single family home is 1,364 sqft and on a lot of 15,682 sqft (or 0.36 acres) with 3 bedrooms, 2 baths and is 116 years old. This property was listed on 05/06/2026 and has been priced for sale at $698,000.

Nearby zip codes are 03222, 03441 2631, 03441 and 03446. This property neighbors other cities such as Richmond and Swanzey.

PrimeMLS

Listing Last updated . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. Walk Score map and data provided by Walk Score. Google map provided by Google. Bing map provided by Microsoft Corporation.

All information provided is deemed reliable but is not guaranteed and should be independently verified.

Listing information courtesy of: BHG Masiello Keene

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display 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 06/16/2026