63 Headlands Rd, Winchester, NH 03470
OFF MARKET

63 Headlands Rd
Winchester, NH 03470

  • 2 Beds
  • 1.5 Baths
  • 1,911 sqft (on 0.75 acres)

$727,100

Trulia Estimate
as of Aug 23, 2026

$727,100

Trulia Estimate
as of Aug 23, 2026
2 Beds
1.5 Baths
1,911 sqft
(on 0.75 acres)

Home Value

Trulia Estimate
$727K
Since last month
Increased$6K (+0.8%)
Since last year
Increased$55K (+8.1%)
Since last sale
Increased$80K (+12.4%)
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 +171% in the last 10 years
MonthEstimated value
2026
August 2026$727K
July 2026$721K
June 2026$720K
May 2026$721K
March 2026$719K
February 2026$721K
January 2026$721K
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
73 Lake Shore Drive, Winchester, NH
0.15
Single-Family Home
$729,900
01/06/26
4
3
2,975
25 Headlands Road, Winchester, NH
0.13
Single-Family Home
$360,000
09/26/25
1
1
756
45 Forest Lake Circle, Winchester, NH
0.42
Single-Family Home
$355,000
03/20/26
4
2
1,500
49 Forest Lake Circle, Winchester, NH
0.44
Single-Family Home
$330,000
07/31/26
2
1
937
30 Melvin Bridge Road, Winchester, NH
0.91
Single-Family Home
$350,700
07/07/26
4
2
1,750
56 Melvin Bridge Road, Winchester, NH
1.03
Single-Family Home
$280,000
11/04/25
3
1
1,295
515 Forest Lake Road, Winchester, NH
0.78
Single-Family Home
$205,000
09/04/25
3
1.5
2,240
68 Michigan Street, Winchester, NH
1.05
Single-Family Home
$308,000
08/28/25
3
1
1,176
62 Parker Street, Winchester, NH
1.45
Single-Family Home
$430,000
07/29/26
4
1.5
2,252
128 Keene Road, Winchester, NH
1.02
Single-Family Home
$225,000
08/28/25
3
1.5
1,320

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
71 Headlands Road, Winchester, NH 03470
0.03
$445,000
3
2
1,066
For Sale
39 Headlands Road, Winchester, NH 03470
0.09
$698,000
3
2
1,364
For Sale
73 Lake Shore Drive, Winchester, NH 03470
0.15
$729,900
4
3
2,975
Recently Sold
20 Lake Shore Drive, Winchester, NH 03470
0.11
$135,000
-
-
-
For Sale
27 Headlands Road, Winchester, NH 03470
0.13
$715,000
2
1.5
1,351
For Sale
25 Headlands Road, Winchester, NH 03470
0.13
$363,300
1
1
756
Off Market
7 Lake Shore Drive, Winchester, NH 03470
0.13
$100,000
-
-
-
Recently Sold
306 Forest Lake Road, Winchester, NH 03470
0.17
$420,800
3
2
1,755
Off Market
370 Forest Lake Road, Winchester, NH 03470
0.22
$458,400
-
-
-
Off Market
372 Forest Lake Road, Winchester, NH 03470
0.25
$345,100
2
1
820
Off Market
20 Whitcomb Court, Winchester, NH 03470
0.31
$600,200
2
1
1,252
Off Market
12 Rabbit Hollow Road, Winchester, NH 03470
0.31
$289,900
3
1
1,118
For Sale

Local Information

  • Map ViewExplore the area around 63 Headlands Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1916
Lot Size
0.75 acres
Living Area
1,911 sqft
Price/Sqft
$380
Parking
Garage

About this House

Beautiful property set amongst a pine forest with sweeping views of Forest lake, this tudor style chalet is loaded with charm and modern comforts. It has two bedroom and 1 1/2 baths, with a large loft area above for more sleeping and living space. New Bathroom renovations 2024, New Roof 2023, New exterior paint 2024, New cement slab in two car garage 2023, Large Fireplace, Washer/dryer. Home is located near the end of a dead end road, so feels very private and exclusive. This purchase includes three parcels totaling 2.03 acres in total, with the possibility for further development. There are trails that encircle the property through the forest and onto a peninsula, to your own private beachfront! Forest Lake, with its newly rebuilt dam in 2025, is perfect for swimming, kayaking, canoing or pontooning. The NH scenery is idyllic, with bright summer sunsets and million dollar views of fall foliage in the autumn. The front of the home is newly landscaped in 2024 to include a new stream stone retaining wall and granite pathway and steps. If you are looking to live in an historic, 100+ year old home with modern conveniences, this is for you! It has functioned as a successful short term rental for the past two years. Take 'free vacations' and rent when you're not there! Convenient to Keene, NH, where you fill find all of the predicable big box stores and restaurants, as well as cute shops and boutiques along the main street.
63 Headlands Rd, Winchester, NH 03470 is a 2 bedroom, 2 bathroom, 1,911 sqft single-family home built in 1916. It last sold for $647,000 on Oct 7, 2022. It is currently off market. The Trulia Estimate is $727,100, with a rent estimate of $2,532/month.

Home Details for 63 Headlands Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1916
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Lot Information

Lot Area: 0.75 acres

Price and Tax history

DateEventPrice
Oct 29, 2025
Source: PrimeMLS #5042562
ListingRemoved
$720,000
May 23, 2025
Source: PrimeMLS #5042562
Listed For Sale
$720,000
May 21, 2025
Source: N/A
ListingRemoved
Apr 14, 2025
Source: PrimeMLS #5036167
Listed For Sale
$725,000
Aug 9, 2024
Source: PrimeMLS #5008089
ListingRemoved
$765,000

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 63 Headlands Rd

  • What is 63 Headlands Rd estimated to be worth?
    Trulia's estimated value for 63 Headlands Rd in Winchester, NH is $727,100.
  • What is the price history for 63 Headlands Rd?
    63 Headlands Rd in Winchester, NH last sold for $647,000 in October 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 63 Headlands Rd?
    The lot at 63 Headlands Rd in Winchester, NH is about 0.75 acres (32,670 sq ft).
  • Does 63 Headlands Rd have a garage?
    Yes, 63 Headlands Rd in Winchester, NH has a garage.

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 63 Headlands Rd

Skip to last item
Skip to first item

Homes for sale near 63 Headlands Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item