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$698,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1 Partial Bath
  • 1,364 Sq. Ft.
  • 0.36 Acres
  • Updated 2 days ago
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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!

Full Property Details for 39 Headlands Rd

General

  • Price: $698,000
  • Taxes: $11,479 (2025)
  • Status: Active
  • Type: Single Family
  • Source: PrimeMLS
  • MLS ID: 5087379
  • Updated: 5/6/2026
  • Added to Site: 2 day(s) ago

Interior

  • Number of Rooms: 7
  • Interior Features: Ceiling Fan, Wood Fireplace, Laundry Hookups, Primary BR w/ BA, Natural Woodwork, Wood Stove Insert, 1st Floor Laundry
  • Fireplace: Yes
  • Appliances: Microwave, Gas Range, Refrigerator, Electric Water Heater, Owned Water Heater, Tank Water Heater
  • Flooring: Carpet, Hardwood, Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 1
  • 3/4 Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Equipment: Battery Smoke Detector

Exterior

  • Exterior Features: Barn, Deck, Garden Space, Natural Shade, Outbuilding, Covered Porch, Screened Porch, Private Dock
  • Color: Brown

Parking

  • Parking: Driveway, Covered, Carport

Location

  • County: Cheshire
  • Driving Directions: Use GPS

School Information

  • School District: Winchester
  • Elementary School: Winchester School
  • Middle School: Winchester School
  • High School: Keene High School

Heating & Cooling

  • Cooling Type: Central AC, Mini Split
  • Heating Type: Propane, Wood, Electric, Forced Air

Utilities

  • Sewer: 1000 Gallon, Concrete, Holding Tank, Leach Field, Private

Structural Information

  • Construction Status: Existing
  • Basement Entrance: Walkout
  • Basement Desc.: Crawlspace, Dirt, Gravel, Partial, Walkout
  • Roof: Metal
  • Stories/Levels: 1.75
  • Square Feet: 1,364
  • Finished Total: 1,364 Sq. Ft.
  • Finished Above Grnd: 1,364 Sq. Ft.
  • Year Built: 1910

Lot Features

  • Lot Size (Acres): 0.36
  • Lot Size (Sq. Ft.): 15,682
  • Frontage: Yes Road Frontage
  • Frontage Feet: 104
  • Driveway/Sidewalk: Crushed Stone
  • Zoning: Lake

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Type: Lake
  • Water Front Name: Forest Lake
  • Water Front Owned: 1

Financial Considerations

  • Price Per Sq. Ft.: $511.73
  • Tax Amount: $11,479
  • Tax Year: 2025

Disclosures and Reports

  • Documents Avail.: Deed, PERC Test, Property Disclosure, Tax Map
  • Lot Number: 12

Listed by BHG Masiello Keene, Nancy S Panza

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Listed by BHG Masiello Keene, Nancy S Panza

Listing agent

— 39 Headlands Rd —

  • Nancy S Panza

    BHG Masiello Keene

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 39 Headlands Rd

School District:Winchester School District, Winchester, NH
NameGradesDistance
Winchester School
85 Parker Street, Winchester, NH 03470
PK-81.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 39 Headlands Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/06/2026
Listed
$698,000
138.61%
MLS
7/31/2015
Sold
$292,533
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 39 Headlands Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$8,670
-8%
$296,400
—
2023
$9,390
10%
$296,400
—
2022
$8,507
-10%
$296,400
—
2021
$9,423
11%
$296,400
—
2020
$8,527
-12%
$296,400
8%
2019
$9,744
4%
$273,400
1%
2018
$9,374
60%
$269,900
40%
2016
$5,871
—
$192,300
—
2015
$5,881
-5%
$192,300
-5%
2014
$6,220
-2%
$203,400
-1%
2013
$6,330
—
$206,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 39 Headlands Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by BHG Masiello Keene, Nancy S Panza

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39 Headlands Road, Winchester, NH 03470 (MLS# 5087379) is a Single Family property with 3 bedrooms, 1 full bathroom and 1 partial bathroom. 39 Headlands Road is currently listed for $698,000 and was received on May 06, 2026. Want to learn more about 39 Headlands Road? Do you have questions about finding other Single Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

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