39 Headlands Rd, Winchester, NH 03470
Property image
Property image
OFF MARKET

$670,400

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 1,154 sqft (on 0.30 acres)

39 Headlands Rd, Winchester, NH 03470

Est. Refi. Payment $4,582/mo*
Refinance Your Home
Currently Off Market - Sold Nov 4, 2022 for $650,000

Home Value

Trulia Estimate
$670K
Since last month
Decreased$8K (-1.1%)
Since last year
Decreased$107K (-13.7%)
Since last sale
Increased$20K (+3.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +120% in the last 10 years
MonthEstimated value
2026
September 2026$670K
August 2026$678K
July 2026$678K
June 2026$677K
May 2026$687K
April 2026$724K
March 2026$720K
February 2026$708K
January 2026$694K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
25 Headlands Road, Winchester, NH
0.07
Single-Family Home
$360,000
09/26/25
1
1
756
49 Forest Lake Circle, Winchester, NH
0.42
Single-Family Home
$330,000
07/31/26
2
1
937
45 Forest Lake Circle, Winchester, NH
0.41
Single-Family Home
$355,000
03/20/26
4
2
1,500
73 Lake Shore Drive, Winchester, NH
0.23
Single-Family Home
$729,900
01/06/26
4
3
2,975
56 Melvin Bridge Road, Winchester, NH
1.07
Single-Family Home
$280,000
11/04/25
3
1
1,295
82 Howard Street, Winchester, NH
1.33
Single-Family Home
$290,000
07/13/26
3
2
1,100
20 Bilo Avenue, Winchester, NH
1.51
Single-Family Home
$295,000
03/13/26
3
1
1,145
30 Melvin Bridge Road, Winchester, NH
0.95
Single-Family Home
$350,700
07/07/26
4
2
1,750
12 Miner Court, Winchester, NH
1.52
Single-Family Home
$259,000
12/30/25
3
1
1,416
10 Swan Street, Winchester, NH
1.48
Single-Family Home
$305,000
03/31/26
3
1
1,689

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
27 Headlands Road, Winchester, NH 03470
0.06
$715,000
2
1.5
1,351
For Sale
25 Headlands Road, Winchester, NH 03470
0.07
$363,700
1
1
756
Off Market
7 Lake Shore Drive, Winchester, NH 03470
0.06
$100,000
-
-
-
Recently Sold
306 Forest Lake Road, Winchester, NH 03470
0.08
$420,500
3
2
1,755
Off Market
71 Headlands Road, Winchester, NH 03470
0.11
$445,000
3
2
1,066
For Sale
20 Lake Shore Drive, Winchester, NH 03470
0.11
$135,000
-
-
-
For Sale
370 Forest Lake Road, Winchester, NH 03470
0.21
$469,500
-
-
-
Off Market
372 Forest Lake Road, Winchester, NH 03470
0.22
$345,200
2
1
820
Off Market
73 Lake Shore Drive, Winchester, NH 03470
0.23
$729,900
4
3
2,975
Recently Sold
20 Whitcomb Court, Winchester, NH 03470
0.30
$603,700
2
1
1,252
Off Market
45 Forest Lake Circle, Winchester, NH 03470
0.41
$355,000
4
2
1,500
Recently Sold
49 Forest Lake Circle, Winchester, NH 03470
0.42
$330,000
2
1
937
Recently Sold

Local Information

  • Map ViewExplore the area around 39 Headlands Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1910
0.3 acre lot
1,154 sqft
$581/sqft

About this House

This single-family home is located at 39 Headlands Rd, Winchester, NH. 39 Headlands Rd is in Winchester, NH and in ZIP code 03470. This property has 3 bedrooms, 1 bathroom and approximately 1,154 sqft of floor space. This property has a lot size of 0.30 acres and was built in 1910.
39 Headlands Rd, Winchester, NH 03470 is a 3 bedroom, 1 bathroom, 1,154 sqft single-family home built in 1910. It last sold for $650,000 on Nov 4, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $670,400, with a rent estimate of $2,849/month.

Home Details for 39 Headlands Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air

Exterior Features

Exterior Home Features
Roof: MetalExterior: Wood

Property Information

Year Built
Year Built: 1910
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.30 acres

Price and Tax history

DateEventPrice
Sep 8, 2026
Source: PrimeMLS #5087379
ListingRemoved
$698,000
May 6, 2026
Source: PrimeMLS #5087379
Listed For Sale
$698,000
Aug 29, 2024
Source: PrimeMLS #5003972
ListingRemoved
$750,000
Jul 24, 2024
Source: PrimeMLS #5003972
PriceChange
$750,000
Price decreased by 6%
Jul 8, 2024
Source: PrimeMLS #5003972
Listed For Sale
$795,000

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
15
1MoM

Around this home

What Locals Say about Winchester

At least 16 Trulia users voted on each feature.

  • 91 % Say parking is easy

  • 88 % Say car is needed

  • 80 % Say yards are well-kept

  • 76 % Say there's holiday spirit

  • 73 % Say there's wildlife

  • 68 % Say people would walk alone at night

  • 60 % Say it's dog friendly

  • 56 % Say it's quiet

  • 53 % Say kids play outside

  • 48 % Say neighbors are friendly

  • 43 % Say they plan to stay for at least 5 years

  • 35 % Say it's walkable to grocery stores

  • 31 % Say streets are well-lit

  • 30 % Say there are community events

  • 23 % Say it's walkable to restaurants

  • 17 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Flynnstrucking
    "there is Plenty of open space to walk your dog without having to worry about picking up after it. you can have your own private trails right out your back door"
    0
    Flag
  • Angelica M.
    "Dope heads. Idk it’s not the best or worst place to live. It’s far away from society and school sucks"
    0
    Flag
  • unknown
    "Boring. Druggies, condemned, abandon, no activity, lots of kid parks, school, noises, fast cars, no laws, rude people"
    0
    Flag
  • Jeannette D.
    "Compared to other outlying Cheshire County towns, Winchester, NH gets the highest mark for in-town amenities. Winchester, NH has its own locally owned grocery store, hardware store, pharmacy, clinic, bank and more! Additionally, the natural amenities are outstanding and include, Forest Lake, Ashuelot River, 14,000 acre Pisgah State Park, Rails to Trails. In Winchester, NH, you get the best of both worlds - rural living with close by amenities. AND you can get there from here! 15 minutes to I91 in Berndarston, MA, 20 minutes to Keene, NH, Greenfield, MA or Brattleboro, VT."
    8
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 39 Headlands Rd

  • What is 39 Headlands Rd estimated to be worth?
    Trulia's estimated value for 39 Headlands Rd in Winchester, NH is $670,400.
  • What is the price history for 39 Headlands Rd?
    39 Headlands Rd in Winchester, NH last sold for $650,000 in November 2022.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Winchester?
    Residents describe Winchester, NH as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Winchester, NH.
  • How big is the lot at 39 Headlands Rd?
    The lot at 39 Headlands Rd in Winchester, NH is about 0.30 acres (13,068 sq ft).

Apartments for Rent

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Off Market Homes Near 39 Headlands Rd

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