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

4 Headlands Rd
Winchester, NH 03470

2 Beds
1 Bath
1,302 sqft (on 0.31 acres)

$213,000

Trulia Estimate

as of Jul 6, 2026

Est. Refi. Payment $1,468/mo*

Refinance Your Home

$213,000

Trulia Estimate

as of Jul 6, 2026

Est. Refi. Payment $1,468/mo*

Refinance Your Home

2 Beds

1 Bath

1,302 sqft

(on 0.31 acres)

Local Information

Map ViewExplore the area around 4 Headlands Rd.
Schools1 Preschool School1 Elementary School1 Middle School
Shop & Eat

-- mins to

Commute Destination

Description

Still Standing! Aged A frame with large attached garage on wooded lot. One floor living with exception of second bedroom. Property has interior water damage as well as exterior rot and failing roof. Needs attention throughout. Utilities will not be turned on for inspections. Sold As Is and subject to Seller addendums.

4 Headlands Rd, Winchester, NH 03470 is a 2 bedroom, 1 bathroom, 1,302 sqft single-family home built in 1975. It last sold for $24,500 on Mar 28, 2014. It is currently off market. The Trulia Estimate is $213,000, with a rent estimate of $2,146/month.

Home Highlights

Parking

No Info

Outdoor

No Info

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 4 Headlands Rd

Interior Features
Heating & Cooling Heating: Forced Air, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 2
Interior Details Number of Rooms: 5

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Wood

Property Information
Year Built Year Built: 1975
Property Type / Style Property Type: Single Family HomeArchitecture: Other

Lot Information
Lot Area: 0.31 acres

Price History for 4 Headlands Rd

Date	Price	Event	Source
03/28/2014	$24,500	Sold	N/A
Recording Date 03/28/2014 County Transfer Tax N/A Total Transfer Tax N/A
02/28/2014	$34,900	Listed For Sale	Agent Provided

01/24/2014	$44,900	ListingRemoved	Agent Provided

12/11/2013	$44,900	PriceChange	Agent Provided
Price Change $10,000 (-18%)
11/09/2013	$54,900	Listed For Sale	Agent Provided

09/23/2013	$56,400	Sold	N/A
Recording Date 09/23/2013 County Transfer Tax N/A Total Transfer Tax $33
12/14/2012	$75,000	PriceChange	Agent Provided
Price Change $20,000 (-21%)
08/31/2012	$95,000	PriceChange	Agent Provided
Price Change $20,000 (-17%)
08/01/2012	$115,000	Listed For Sale	Agent Provided

Market trends in Winchester

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Skip to last item

Results are loading

Skip to first item

Property Tax and Assessment

Year	2024
Tax	$3,551
Assessment	$121,400

Home facts updated by county records

Comparable Sales for 4 Headlands Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
22 South Dr, Winchester, NH	0.16	Single-Family Home	$420,000	08/01/25	2	1	911
25 Headlands Road, Winchester, NH	0.11	Single-Family Home	$360,000	09/26/25	1	1	756
45 Forest Lake Circle, Winchester, NH	0.26	Single-Family Home	$355,000	03/20/26	4	2	1,500
37 Town Beach Road, Winchester, NH	0.56	Single-Family Home	$365,000	08/19/25	2	1	817
56 Melvin Bridge Road, Winchester, NH	0.98	Single-Family Home	$280,000	11/04/25	3	1	1,295
73 Lake Shore Drive, Winchester, NH	0.31	Single-Family Home	$729,900	01/06/26	4	3	2,975
68 Michigan Street, Winchester, NH	1.29	Single-Family Home	$308,000	08/28/25	3	1	1,176
82 Howard Street, Winchester, NH	1.48	Single-Family Home	$140,000	03/02/26	3	2	1,100
515 Forest Lake Road, Winchester, NH	0.68	Single-Family Home	$205,000	09/04/25	3	1.5	2,240
128 Keene Road, Winchester, NH	1.24	Single-Family Home	$225,000	08/28/25	3	1.5	1,320

Nearby homes

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

Skip to last item

OFF MARKET
Est. $342,800
2 bd
1 ba
820 sqft
372 Forest Lake 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
OFF MARKET
Est. $449,100
370 Forest Lake Road,
Winchester, NH 03470
PrimeMLS, Closed
OFF MARKET
Est. $421,500
3 bd
2 ba
1,755 sqft
306 Forest Lake Road,
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
FOR SALE
0.36 ACRES
$698,000
3 bd
2 ba
1,364 sqft
39 Headlands Road,
Winchester, NH 03470
PrimeMLS, Active
SOLD
JAN 23, 2026
$100,000
7 Lake Shore Drive,
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
SOLD
MAR 20, 2026
$355,000
4 bd
2 ba
1,500 sqft
45 Forest Lake Circle,
Winchester, NH 03470
PrimeMLS, Closed
FOR SALE
2.75 ACRES
$135,000
20 Lake Shore Drive,
Winchester, NH 03470
PrimeMLS, Active
OFF MARKET
Forest Lake Road,
Winchester, NH 03470
PrimeMLS, Closed

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 4 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 4 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
Flag
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
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.
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
Flag