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)

$722,600

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $4,888/mo*
Refinance Your Home

$722,600

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $4,888/mo*
Refinance Your Home
2 Beds
1.5 Baths
1,911 sqft
(on 0.75 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 63 Headlands Rd

DatePriceEventSource
10/29/2025$720,000ListingRemovedPrimeMLS #5042562
05/23/2025$720,000Listed For SalePrimeMLS #5042562
05/21/2025ListingRemovedN/A
04/14/2025$725,000Listed For SalePrimeMLS #5036167
08/09/2024$765,000ListingRemovedPrimeMLS #5008089
08/03/2024$765,000Listed For SalePrimeMLS #5008089
10/07/2022$647,000Sold
PrimeMLS #4911066
09/02/2022$699,000ContingentPrimeMLS #4911066
08/17/2022$699,000PriceChange
PrimeMLS #4911066
06/25/2022$750,000PriceChange
PrimeMLS #4911066
05/20/2022$799,999Listed For SalePrimeMLS #4911066
08/30/1996$150,000Sold
N/A
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Property Tax and Assessment

Year2024
Tax$7,503
Assessment$256,500
Home facts updated by county records

Comparable Sales for 63 Headlands Rd

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
335 Forest Lake Rd, Winchester, NH
0.28
Single-Family Home
$280,000
06/18/25
2
1
1,303
22 South Dr, Winchester, NH
0.28
Single-Family Home
$420,000
08/01/25
2
1
911
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
37 Town Beach Road, Winchester, NH
0.62
Single-Family Home
$365,000
08/19/25
2
1
817
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
128 Keene Road, Winchester, NH
1.02
Single-Family Home
$225,000
08/28/25
3
1.5
1,320

Nearby homes

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Assigned Schools

These are the assigned schools for 63 Headlands Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
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Homes for sale near 63 Headlands Rd

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Off Market Homes Near 63 Headlands Rd

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Homes for rent near 63 Headlands Rd

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63 Headlands Rd, Winchester, NH 03470 is a 2 bedroom, 2 bathroom, 1,911 sqft single-family home built in 1916. This property is not currently available for sale. 63 Headlands Rd was last sold on Oct 7, 2022 for $647,000. The current Trulia Estimate for 63 Headlands Rd is $722,600.