Is parking easy in Winchester, NH?

As of early 2026, 91% of users say parking is easy

Is a car needed in Winchester, NH?

As of early 2026, 88% of users say car is needed

Are yards well-kept in Winchester, NH?

As of early 2026, 80% of users say yards are well-kept

Does Winchester, NH show holiday spirit?

As of early 2026, 76% of users say there's holiday spirit

Is there wildlife in Winchester, NH?

As of early 2026, 73% of users say there's wildlife

Would people walk alone at night in Winchester, NH?

As of early 2026, 68% of users say people would walk alone at night

Is Winchester, NH dog-friendly?

As of early 2026, 60% of users say it's dog friendly

Is Winchester, NH quiet?

As of early 2026, 56% of users say it's quiet

Do kids play outside in Winchester, NH?

As of early 2026, 53% of users say kids play outside

Are neighbors friendly in Winchester, NH?

As of early 2026, 48% of users say neighbors are friendly

Do residents of Winchester, NH plan to stay at least 5 years?

As of early 2026, 43% of users say they plan to stay for at least 5 years

Is Winchester, NH walkable to grocery stores?

As of early 2026, 35% of users say it's walkable to grocery stores

Are the streets well-lit in Winchester, NH?

As of early 2026, 31% of users say streets are well-lit

Are there community events in Winchester, NH?

As of early 2026, 30% of users say there are community events

Is Winchester, NH walkable to restaurants?

As of early 2026, 23% of users say it's walkable to restaurants

Does Winchester, NH have sidewalks?

As of early 2026, 17% of users say there are sidewalks

OFF MARKET

158 Upper Headlands Rd
Winchester, NH 03470

Studio

Studio

Local Information

Map ViewExplore the area around 158 Upper Headlands Rd.
Schools1 Preschool School1 Elementary School1 Middle School
Shop & Eat

-- mins to

Commute Destination

Description

158 Upper Headlands Rd is in Winchester, NH and in ZIP code 03470.

158 Upper Headlands Rd, Winchester, NH 03470 is a studio property. It is currently off market. The Trulia Estimate rent is $1,495/month.

Market trends in Winchester

Last updated May 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

2MoM

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Comparable Sales for 158 Upper Headlands Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
73 Lake Shore Drive, Winchester, NH	0.21	Single-Family Home	$729,900	01/06/26	4	3	2,975
22 South Dr, Winchester, NH	0.25	Single-Family Home	$420,000	08/01/25	2	1	911
37 Town Beach Road, Winchester, NH	0.31	Single-Family Home	$365,000	08/19/25	2	1	817
45 Forest Lake Circle, Winchester, NH	0.32	Single-Family Home	$355,000	03/20/26	4	2	1,500
25 Headlands Road, Winchester, NH	0.38	Single-Family Home	$360,000	09/26/25	1	1	756
515 Forest Lake Road, Winchester, NH	0.48	Single-Family Home	$205,000	09/04/25	3	1.5	2,240
56 Melvin Bridge Road, Winchester, NH	0.70	Single-Family Home	$280,000	11/04/25	3	1	1,295
128 Keene Road, Winchester, NH	1.00	Single-Family Home	$225,000	08/28/25	3	1.5	1,320
102 Keene Road, Winchester, NH	1.10	Single-Family Home	$218,500	08/01/25	3	1.5	3,603
96 Old Spofford Road, Winchester, NH	1.13	Single-Family Home	$321,000	10/31/25	2	1	960

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
162 Upper Headlands Road,
Winchester, NH 03470
PrimeMLS, Closed
SOLD
JAN 6, 2026
$729,900
4 bd
3 ba
2,975 sqft
73 Lake Shore Drive,
Winchester, NH 03470
PrimeMLS, Closed
OFF MARKET
Est. $570,900
2 bd
1 ba
1,252 sqft
20 Whitcomb Court,
Winchester, NH 03470
PrimeMLS, Closed
OFF MARKET
Est. $449,100
370 Forest Lake Road,
Winchester, NH 03470
PrimeMLS, Closed
OFF MARKET
Est. $364,900
2 bd
1 ba
817 sqft
37 Town Beach Road,
Winchester, NH 03470
PrimeMLS, Closed
SOLD
MAR 20, 2026
$355,000
4 bd
2 ba
1,500 sqft
45 Forest Lake Circle,
Winchester, NH 03470
PrimeMLS, Closed
FOR SALE
0.39 ACRES
$495,000
3 bd
2 ba
1,066 sqft
71 Headlands Road,
Winchester, NH 03470
PrimeMLS, Active
OFF MARKET
Est. $281,400
3 bd
1 ba
1,149 sqft
43 Town Beach Road,
Winchester, NH 03470
PrimeMLS, Closed
OFF MARKET
Est. $342,800
2 bd
1 ba
820 sqft
372 Forest Lake Road,
Winchester, NH 03470
PrimeMLS, Closed
OFF MARKET
Est. $400,300
3 bd
2 ba
1,654 sqft
366 Keene Road,
Winchester, NH 03470
PrimeMLS, Closed
SOLD
SEP 26, 2025
$360,000
1 bd
1 ba
756 sqft
25 Headlands Road,
Winchester, NH 03470
PrimeMLS, Closed
FOR SALE
$720,000
2 bd
1.5 ba
1,351 sqft
27 Headlands Road,
Winchester, NH 03470
PrimeMLS, Active

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Additional Cost

Assigned Schools

These are the assigned schools for 158 Upper Headlands Rd.

Winchester School
PK-8
Public
322 Students
Winchester School District
3/10
GreatSchools Rating
Parent Rating Average
hate this school . Can't wait to get out .
Student Review
1y ago
2 Reviews
Check out schools near 158 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
Resident
5y ago
"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
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Angelica M.
Resident
6y ago
"Dope heads. Idk it’s not the best or worst place to live. It’s far away from society and school sucks"
0
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unknown
Resident
7y ago
"Boring. Druggies, condemned, abandon, no activity, lots of kid parks, school, noises, fast cars, no laws, rude people"
0
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Jeannette D.
13y ago
"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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