39 Headlands Rd

Winchester, NH 03470

$698,000
Price
3
Beds
1,364 Sq. Ft.
$512 / Sq. Ft.
1,364
Sq. Ft.
$512
per Sq. Ft.
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Description

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...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!
  1. Listed by Nancy Panza • BHG Masiello Keene

Property Details for 39 Headlands Road

Water Body Type
Lake
Water View
Yes
Waterfront Property
Yes
Zoning
Lake
LISTING UPDATED: 05/07/2026 08:23 PM

Property Details for 39 Headlands Road

StatusActive
MLS #5087379
Days on Market41
Taxes$11,479 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1910
Lot Size0.36 AC / 15,681 SF
CountyCheshire County
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Location

Listing Courtesy of BHG Masiello Keene
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Building Information for 39 Headlands Road

Stories1Year Built1910Building Size-Lot Size0.36 AC / 15,681 SF

Payment Calculator

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$4,435 per month

30 year fixed, 6.36% Interest

Principal and Interest

$3,478

Property Taxes

$957

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 39 Headlands Road

Summary
Location and General Information
  • City: Winchester
  • County: NH-Cheshire
  • Directions: Use GPS
  • Latitude: 42.787683074144617
  • Longitude: -72.362776932540896
  • Road Frontage: Yes
  • Seasonal: No
  • State: NH
  • Street Designation: Road
  • Map: 33
  • Zip Code: 03470
Taxes and HOA Information
  • Condo Fees: No
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: No
  • Driveway: Crushed Stone
Property
Lot Information
  • Block: 0
  • Lot: 12
  • Lot Features: Country Setting, Lake Frontage, Lake View, Landscaped, Mountain View, Sloping, View, Waterfront, Wooded
  • Lot Size Acres: 0.36
  • Road Frontage Length: 104.0
  • Water Frontage Length: 76.0
  • Water Body Name: Forest Lake
  • Waterfront Property Rights: Exclusively Owned
  • Total Finished Area: 1364.0
  • Above Grade Finished Area: 1364.0
  • Above Grade Finished Area Source: Public Records
  • Above Grade Unfinished Area: 0.0
  • Below Grade Finished Area: 0.0
  • Below Grade Unfinished Area: 800.0
  • BelowGradeUnfinishedAreaSource: Public Records
  • Lot Size Square Feet: 15682.0
  • Total Area: 2164.0
Property and Assessments
  • Current Use: No
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Resort: No
  • Surveyed: Unknown
  • Water Body Restrictions: Unknown
  • Year Built: 1910
  • School District: Winchester
  • High School: Keene High School
  • Middle/Jr School: Winchester School
  • Elementary School: Winchester School
Utilities
  • Electric Company: Eversource
  • Electric: 200+ Amp Service, Circuit Breaker(s)
  • Sewer: 1000 Gallon, Concrete, Holding Tank, Leach Field, Private
  • Water Source: Public
  • Utilities: Cable at Site
  • Internet: Fiber Optic Internt Avail
Interior and Exterior Features
Exterior Features
  • Color: Brown
  • Construction Materials: Wood Frame, Vertical Siding, Wood Exterior, Wood Siding
  • Roof: Metal
Interior Features
  • Appliances: Microwave, Gas Range, Refrigerator, Electric Water Heater, Owned Water Heater, Tank Water Heater
  • Basement: Yes
  • Basement Access Type: Walkout
  • Basement Description: Crawl Space, Dirt, Gravel, Partial, Walkout
  • Flooring: Carpet, Hardwood, Tile
  • Heating: Propane, Wood, Electric, Forced Air
  • Cooling: Central AC, Mini Split
  • Total Stories: 1.75
  • Rooms Total: 7
  • Bathrooms Full: 1
  • Bathrooms Half: 0
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 1
  • Bedrooms Total: 3
  • Bathrooms Total: 2

Property History for 39 Headlands Road

DateEvent & SourcePriceAppreciation
May 6, 2026

Listed (Active)

New England Real Estate Network #5087379

$698,000—
Dec 9, 2024

Expired

New England Real Estate Network #5003972

—
Oct 4, 2024

Withdrawn

New England Real Estate Network #5003972

—
DateEvent & SourcePrice
05/06/2026

Listed (Active)

New England Real Estate Network #5087379

$698,000
12/09/2024

Expired

New England Real Estate Network #5003972

—
10/04/2024

Withdrawn

New England Real Estate Network #5003972

—

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 39 Headlands Road

Taxable ValueLand$129,000Additions$167,400Total$296,400
Tax Record2024$8,670 ($722 / month)
Home Facts
Beds3Baths2Total Finished SqFt1,485 SqFtAbove Grade Finished SqFt1,485 SqFtStories2Lot Size15,682 SqFtStyleSingle Family ResidenceYear Built1910ZoningLAKEFOCountyCHESHIREAPNWNCH M:00033 B:000012 L:000000

Schools near 39 Headlands Road

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Winchester School
Public - PK to 8
Keene High School
Public - 9 to 12
Rating
School
Distance
Winchester School
PublicPK to 8

Keene High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 39 Headlands Road, Winchester, NH 03470

39 Headlands Road is a single family home for sale in Winchester, NH 03470. This property was listed for sale on May 6, 2026 by BHG Masiello Keene, it's currently listed at $698,000. It has been on the market for a total of 41 days and was last sold on November 4, 2022. This listing's school districts are Winchester School District, Keene School District. Nearby schools include Winchester School and Keene High School. 39 Headlands Road is a 3-bed, 2-bath, 1,364 sqft single family home built in 1910.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing 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 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 06/16/2026 07:47 PM