166 Upper Headlands Rd, Winchester, NH 03470
OFF MARKET

166 Upper Headlands Rd
Winchester, NH 03470

  • Studio
  • 0.5 Baths
  • 461 sqft

$225,800

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $1,566/mo*
Refinance Your Home

$225,800

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $1,566/mo*
Refinance Your Home
Studio
0.5 Baths
461 sqft

Local Information

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

Description

Seasonal Waterfront Cottage on Forest Lake.. 82' of water frontage.. nice and gradual walk in with sand.. Open concept cottage with 1/4 bath (toilet only) and nice screened porch to enjoy which overlooks the water. There is a wonderful new dock and a floating dock. Holding tank needs replacement. Enjoy Lake life.. and make some memories. Quick close possible!
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
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 166 Upper Headlands Rd

Interior Features

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

Exterior Features

Exterior Home Features
Roof: MetalExterior: Wood

Property Information

Year Built
Year Built: 1935
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Lot Information

Lot Area: 7405 sqft

Price History for 166 Upper Headlands Rd

DatePriceEventSource
09/02/2022$150,000Sold
PrimeMLS #4924332
08/15/2022$159,900PendingRE/MAX International #4924332
08/06/2022$159,900Listed For SalePrimeMLS #4924332
08/26/2010$65,000Sold
N/A
06/19/2010$125,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax$2,902
Assessment$99,200
Home facts updated by county records

Comparable Sales for 166 Upper Headlands Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
37 Town Beach Road, Winchester, NH
0.22
Single-Family Home
$365,000
08/19/25
2
1
817
25 Headlands Road, Winchester, NH
0.41
Single-Family Home
$360,000
09/26/25
1
1
756
22 South Dr, Winchester, NH
0.23
Single-Family Home
$420,000
08/01/25
2
1
911
45 Forest Lake Circle, Winchester, NH
0.26
Single-Family Home
$355,000
03/20/26
4
2
1,500
335 Forest Lake Rd, Winchester, NH
0.52
Single-Family Home
$280,000
06/18/25
2
1
1,303
56 Melvin Bridge Road, Winchester, NH
0.63
Single-Family Home
$280,000
11/04/25
3
1
1,295
515 Forest Lake Road, Winchester, NH
0.40
Single-Family Home
$205,000
09/04/25
3
1.5
2,240
128 Keene Road, Winchester, NH
1.09
Single-Family Home
$225,000
08/28/25
3
1.5
1,320
73 Lake Shore Drive, Winchester, NH
0.28
Single-Family Home
$729,900
01/06/26
4
3
2,975
82 Howard Street, Winchester, NH
1.32
Single-Family Home
$140,000
03/02/26
3
2
1,100

Nearby homes

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Assigned Schools

These are the assigned schools for 166 Upper 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
    Flag

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Apartments for Rent

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Homes for sale near 166 Upper Headlands Rd

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Off Market Homes Near 166 Upper Headlands Rd

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Homes for rent near 166 Upper Headlands Rd

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166 Upper Headlands Rd, Winchester, NH 03470 is a studio, 1 bathroom, 461 sqft single-family home built in 1935. This property is not currently available for sale. 166 Upper Headlands Rd was last sold on Sep 2, 2022 for $150,000. The current Trulia Estimate for 166 Upper Headlands Rd is $225,800.