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

What is the price history for 162 Upper Headlands Road?

162 Upper Headlands Road in Winchester, NH last sold for $250,000 in January 2024.

Is Winchester a buyer's or seller's market?

Winchester is currently a balanced 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 162 Upper Headlands Road?

The closest schools to 162 Upper Headlands Road in Winchester, NH are Winchester School (Pre-K/Elementary/Middle, rated 3/10).

OFF MARKET

Listed by Laurie Mack, RE/MAX Town & Country, (603) 357-4100 . Bought with Monadnock Realty Group LLC

$250,000

Last sold price

162 Upper Headlands Road, Winchester, NH 03470

Currently Off Market - Sold Jan 4, 2024 for $250,000

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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	Bath	Sqft
7 Lake Shore Drive, Winchester, NH	0.51	Lot/Land	$100,000	01/23/26	-	-
0 Old Hinsdale Road, Winchester, NH	1.65	Lot/Land	$148,950	07/31/26	-	-
Map 6 Lot 15-3 Off Opportunity Drive #15-3, Winchester, NH	1.69	Lot/Land	$110,000	09/18/25	-	-
0 Attleboro Mountain Road #23 & 26, Winchester, NH	1.65	Lot/Land	$30,000	05/15/26	-	-
69 Plumb Pak Drive, Winchester, NH	2.01	Lot/Land	$75,000	07/23/26	-	-
54 Fullam Pond Road, Winchester, NH	2.14	Lot/Land	$55,000	07/29/26	-	-
Map3 Lot9 Scotland Road, Winchester, NH	3.02	Lot/Land	$110,000	07/22/26	-	-
L:64 & 65 Old Turnpike Road, Winchester, NH	3.11	Lot/Land	$129,000	09/01/26	-	-
Map3 Lot9-1 Scotland Road, Winchester, NH	3.28	Lot/Land	$98,000	01/02/26	-	-
M409 L66-1 Old Turnpike Road, Winchester, NH	3.37	Lot/Land	$110,000	03/17/26	-	-

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
73 Lake Shore Drive, Winchester, NH 03470	0.25	$729,900	4	3	2,975	Recently Sold
37 Town Beach Road, Winchester, NH 03470	0.28	$368,600	2	1	817	Off Market
20 Whitcomb Court, Winchester, NH 03470	0.32	$603,700	2	1	1,252	Off Market
370 Forest Lake Road, Winchester, NH 03470	0.33	$469,500	-	-	-	Off Market
43 Town Beach Road, Winchester, NH 03470	0.30	$265,800	3	1	1,149	Off Market
71 Headlands Road, Winchester, NH 03470	0.37	$445,000	3	2	1,066	For Sale
45 Forest Lake Circle, Winchester, NH 03470	0.35	$355,000	4	2	1,500	Recently Sold
366 Keene Road, Winchester, NH 03470	0.34	$479,900	3	2	2,016	For Sale
49 Forest Lake Circle, Winchester, NH 03470	0.37	$330,000	2	1	937	Recently Sold
372 Forest Lake Road, Winchester, NH 03470	0.39	$345,200	2	1	820	Off Market
25 Headlands Road, Winchester, NH 03470	0.43	$363,700	1	1	756	Off Market

Local Information

Map ViewExplore the area around 162 Upper Headlands Road.
Schools1 Preschool School1 Elementary School1 Middle School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Lot/Land

12 acre lot

About this House

Beautiful 12 acre lot with lovely water views and Gardner Mountain in the distance. There are many trails throughout this parcel, very peaceful spot to build your dream lake house. Don't miss this one!!

162 Upper Headlands Road, Winchester, NH 03470 is a lot/land. It last sold for the $250,000 asking price on Jan 4, 2024. This property is not currently displayed as for sale or rent on Trulia.

Home Details for 162 Upper Headlands Road

Active Status
MLS Status: Closed

Interior Features
Appliances & Utilities Utilities: None, Sewer Not Available, No Internet
Gas & Electric Electric: At Street
View Has a ViewView: Water, Lake, Mountain(s)

Exterior Features
Frontage Waterfront: Lake Access, Lake Front, WaterfrontRoad Frontage: Other, Dead End, Private RoadRoad Surface Type: Dirt, Gravel
Water & Sewer Water Body: Forest Lake
Farm & Range Frontage Length: Road frontage: 377

Property Information
Property Type / Style Property Type: LandProperty Subtype: Unimproved Land

Price & Status
Price List Price: $250,000

Location
Direction & Address City: Winchester
School Information Elementary School: Winchester SchoolElementary School District: Keene Sch Dst SAU #29Jr High / Middle School: Keene Middle SchoolJr High / Middle School District: Keene Sch Dst SAU #29High School: Keene High SchoolHigh School District: Keene Sch Dst SAU #29

Lot Information
Lot Area: 12 Acres

Miscellaneous
Mls Number: 4980140Water ViewWater View: Water, Lake

Price and Tax history

Date	Event	Price
Jan 4, 2024 Source: PrimeMLS #4980140	Sold	$250,000
Dec 16, 2023 Source: PrimeMLS #4980140	Contingent	$250,000
Dec 13, 2023 Source: PrimeMLS #4980140	Listed For Sale	$250,000

Year	Property tax	Tax assessment
2024	$4,733	$161,821

Additional Cost

Market trends in Winchester

Last updated August 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

Around this home

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

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
7y ago
"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
Resident
7y ago
"Boring. Druggies, condemned, abandon, no activity, lots of kid parks, school, noises, fast cars, no laws, rude people"
0
Flag
Jeannette D.
14y 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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LGBTQ Local Legal Protections

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2026-09-14 00:28:20 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.

Frequently asked questions about 162 Upper Headlands Road

What is the price history for 162 Upper Headlands Road?
162 Upper Headlands Road in Winchester, NH last sold for $250,000 in January 2024.
Is Winchester a buyer's or seller's market?
Winchester is currently a balanced 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 162 Upper Headlands Road?
The closest schools to 162 Upper Headlands Road in Winchester, NH are Winchester School (Pre-K/Elementary/Middle, rated 3/10).