164 Upper Headlands Rd, Winchester, NH 03470
OFF MARKET

$302,000

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 658 sqft

164 Upper Headlands Rd, Winchester, NH 03470

Est. Refi. Payment $2,105/mo*
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Home Value

Trulia Estimate
$302K
Since last month
Decreased$3K (-0.9%)
Since last year
Increased$4K (+1.4%)
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 +114% in the last 10 years
MonthEstimated value
2026
August 2026$302K
August 2026$300K
July 2026$305K
June 2026$307K
May 2026$295K
April 2026$281K
March 2026$274K
February 2026$261K
January 2026$262K
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
49 Forest Lake Circle, Winchester, NH
0.29
Single-Family Home
$330,000
07/31/26
2
1
937
45 Forest Lake Circle, Winchester, NH
0.27
Single-Family Home
$355,000
03/20/26
4
2
1,500
25 Headlands Road, Winchester, NH
0.42
Single-Family Home
$360,000
09/26/25
1
1
756
73 Lake Shore Drive, Winchester, NH
0.29
Single-Family Home
$729,900
01/06/26
4
3
2,975
56 Melvin Bridge Road, Winchester, NH
0.63
Single-Family Home
$280,000
11/04/25
3
1
1,295
30 Melvin Bridge Road, Winchester, NH
0.50
Single-Family Home
$350,700
07/07/26
4
2
1,750
82 Howard Street, Winchester, NH
1.31
Single-Family Home
$290,000
07/13/26
3
2
1,100
96 Old Spofford Road, Winchester, NH
1.14
Single-Family Home
$321,000
10/31/25
2
1
960
26 Mechanic Street, Winchester, NH
1.29
Single-Family Home
$377,000
07/21/26
4
2.5
2,736
220 Richmond Road, Winchester, NH
1.91
Single-Family Home
$265,000
10/10/25
2
1.5
1,220

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
162 Upper Headlands Road, Winchester, NH 03470
0.09
-
-
-
-
Off Market
37 Town Beach Road, Winchester, NH 03470
0.22
$368,600
2
1
817
Off Market
43 Town Beach Road, Winchester, NH 03470
0.23
$265,800
3
1
1,149
Off Market
20 Whitcomb Court, Winchester, NH 03470
0.26
$603,700
2
1
1,252
Off Market
73 Lake Shore Drive, Winchester, NH 03470
0.29
$729,900
4
3
2,975
Recently Sold
45 Forest Lake Circle, Winchester, NH 03470
0.27
$355,000
4
2
1,500
Recently Sold
370 Forest Lake Road, Winchester, NH 03470
0.30
$469,500
-
-
-
Off Market
49 Forest Lake Circle, Winchester, NH 03470
0.29
$330,000
2
1
937
Recently Sold
366 Keene Road, Winchester, NH 03470
0.31
$479,900
3
2
2,016
For Sale
372 Forest Lake Road, Winchester, NH 03470
0.35
$345,200
2
1
820
Off Market
71 Headlands Road, Winchester, NH 03470
0.38
$445,000
3
2
1,066
For Sale
Forest Lake Road, Winchester, NH 03470
0.37
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 164 Upper Headlands Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1940
658 sqft
$459/sqft

About this House

This single-family home is located at 164 Upper Headlands Rd, Winchester, NH. 164 Upper Headlands Rd is in Winchester, NH and in ZIP code 03470. This property has 2 bedrooms, 2 bathrooms and approximately 658 sqft of floor space. This property has a lot size of 10018 sqft and was built in 1940.
164 Upper Headlands Rd, Winchester, NH 03470 is a 2 bedroom, 2 bathroom, 658 sqft single-family home built in 1940. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $302,000, with a rent estimate of $2,143/month.

Home Details for 164 Upper Headlands Rd

Interior Features

Heating & Cooling
Heating: Forced Air, CoalHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: OtherExterior: Wood

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Lot Information

Lot Area: 10018 sqft

Price and Tax history

YearProperty taxTax assessment
2024
$4,118
$140,800
Home facts updated by county records

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 164 Upper Headlands Rd

  • What is 164 Upper Headlands Rd estimated to be worth?
    Trulia's estimated value for 164 Upper Headlands Rd in Winchester, NH is $302,000.
  • 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.
  • What are the closest schools to 164 Upper Headlands Rd?
    The closest schools to 164 Upper Headlands Rd in Winchester, NH are Winchester School (Pre-K/Elementary/Middle, rated 3/10).
  • How big is the lot at 164 Upper Headlands Rd?
    The lot at 164 Upper Headlands Rd in Winchester, NH is about 0.23 acres (10,018 sq ft).

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