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

FOR SALE

0.36 ACRES

Listed by Nancy S Panza, BHG Masiello Keene, (603) 352-5433

39 Headlands Road
Winchester, NH 03470

3 Beds
2 Baths
1,364 sqft (on 0.36 acres)

$698,000

3 Beds

2 Baths

1,364 sqft

(on 0.36 acres)

Home Highlights

Parking

Open Parking

Outdoor

Porch

Climate Control

Heating & Cooling

Price/Sqft

$512

Listed

77 days ago

Local Information

Map ViewExplore the area around 39 Headlands Road.
Schools1 Preschool School1 Elementary School1 Middle School
Shop & Eat

-- mins to

Commute Destination

Last check for updates: about 2 hours ago

Listing courtesy of Nancy S Panza

BHG Masiello Keene, (603) 352-5433

Source: PrimeMLS, MLS#5087379

Also Listed on PrimeMLS.

Description

Step across the threshold and into a piece of history. A 1910 waterfront hidden treasure. Timeless architectural details and unparalleled views of Forest Lake make this home a rare blend of old world elegance and modern comfort amidst perennial gardens, stone sculptures and lush greenery A timeless stone fireplace with charming nooks & crannies in the spacious living room echoes the style of simpler times while offering an updated kitchen, two first floor bedrooms and a newer sun-filled master suite with barn-door entrance and lake views ... you'll feel apart from the busy world at this lakeside retreat. There is extended living space outdoors on a spacious and private wooden deck featuring a screened room overlooking the lake as well as a hot/cold outdoor shower! The stairway to your private dock has several landings. A small barn with loft offers plenty of storage or workshop space. There's also a garden shed for more storage. A perfect property for discerning buyers seeking a piece of history combined with unparalleled waterfront view and timeless elegance. Don't miss this opportunity!

Home Details for 39 Headlands Road

Active Status
MLS Status: Active

Interior Features
Interior Details Basement: Crawl Space,Dirt,Gravel,Partial,Walkout,Walk-Out AccessNumber of Rooms: 7
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (three quarters): 1
Dimensions and Layout Living Area: 1364 Square Feet
Appliances & Utilities Utilities: Cable at Site, Fiber Optic Internt AvailAppliances: Microwave, Gas Range, Refrigerator, Electric Water Heater, Owned Water Heater, Tank Water HeaterLaundry: Laundry Hook-ups,1st Floor LaundryMicrowaveRefrigerator
Heating & Cooling Heating: Propane,Wood,Electric,Forced AirHas CoolingAir Conditioning: Central Air,Mini SplitHas HeatingHeating Fuel: Propane
Fireplace & Spa Fireplace: Wood Burning, Wood Stove InsertHas a Fireplace
Gas & Electric Electric: 200+ Amp Service, Circuit Breakers
Windows, Doors, Floors & Walls Flooring: Carpet, Hardwood, Tile
Levels, Entrance, & Accessibility Stories: 1.75Levels: 1.75Accessibility: 1st Floor Bedroom, 1st Floor Full Bathroom, 1st Floor Low-Pile Carpet, 1st Floor LaundryFloors: Carpet, Hardwood, Tile
View Has a ViewView: Water, Lake, Mountain(s)
Security Security: Battery Smoke Detector

Exterior Features
Exterior Home Features Roof: MetalPatio / Porch: Covered Porch, Screened PorchOther Structures: Barn(s), OutbuildingExterior: Deck, Garden, Natural Shade, Private DockFoundation: Block, Pier/Column, StoneGarden
Parking & Garage Has a CarportNo GarageHas Open ParkingParking: Crushed Stone,Driveway,Covered,Carport
Frontage WaterfrontWaterfront: Lake Front, WaterfrontRoad Frontage: Dead End, PublicOn Waterfront
Water & Sewer Sewer: 1000 Gallon, Concrete, Holding Tank, Leach Field, Private SewerWater Body: Forest Lake
Farm & Range Frontage Length: Water frontage: 76, Road frontage: 104
Finished Area Finished Area (above surface): 1364 Square Feet

Days on Market
Days on Market: 77

Property Information
Year Built Year Built: 1910
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: ModifiedArchitecture: Cape,Historic Vintage
Building Construction Materials: Wood Frame, Vertical Siding, Wood Exterior, Wood SidingNot a New Construction

Price & Status
Price List Price: $698,000Price Per Sqft: $512
Status Change & Dates Possession Timing: Close Of Escrow

Location
Direction & Address City: Winchester
School Information Elementary School: Winchester SchoolElementary School District: WinchesterJr High / Middle School: Winchester SchoolJr High / Middle School District: WinchesterHigh School: Keene High SchoolHigh School District: Winchester

Agent Information
Listing Agent Listing ID: 5087379

Building
Building Area Building Area: 2164 Square Feet

Lot Information
Lot Area: 0.36 acres

Miscellaneous
BasementMls Number: 5087379Water ViewWater View: Water, LakeAbove Grade Unfinished Area: 1364Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 800Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Market trends in Winchester

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

3MoM

Price History for 39 Headlands Road

Date	Price	Event	Source
05/06/2026	$698,000	Listed For Sale	PrimeMLS #5087379

08/29/2024	$750,000	ListingRemoved	PrimeMLS #5003972

07/24/2024	$750,000	PriceChange	PrimeMLS #5003972
Price Change $45,000 (-6%)
07/08/2024	$795,000	Listed For Sale	PrimeMLS #5003972

11/04/2022	$650,000	Sold	PrimeMLS #4925678
Recording Date 11/04/2022 County Transfer Tax N/A Total Transfer Tax N/A
08/24/2022	$695,000	Contingent	PrimeMLS #4925678

08/16/2022	$695,000	Listed For Sale	PrimeMLS #4925678

07/31/2015	$292,533	Sold	N/A
Recording Date 07/31/2015 County Transfer Tax N/A Total Transfer Tax $62
06/10/2015	$299,900	Listed For Sale	Agent Provided

11/11/2011	$294,500	ListingRemoved	Agent Provided

07/16/2011	$294,500	Listed For Sale	Agent Provided

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Property Tax and Assessment

Year	2024
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Assessment	$296,400

Home facts updated by county records

Comparable Sales for 39 Headlands Road

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
45 Forest Lake Circle, Winchester, NH	0.42	Single-Family Home	$355,000	03/20/26	4	2	1,500
73 Lake Shore Drive, Winchester, NH	0.24	Single-Family Home	$729,900	01/06/26	4	3	2,975
25 Headlands Road, Winchester, NH	0.08	Single-Family Home	$360,000	09/26/25	1	1	756
37 Town Beach Road, Winchester, NH	0.66	Single-Family Home	$365,000	08/19/25	2	1	817
68 Michigan Street, Winchester, NH	1.12	Single-Family Home	$308,000	08/28/25	3	1	1,176
128 Keene Road, Winchester, NH	1.10	Single-Family Home	$225,000	08/28/25	3	1.5	1,320
30 Melvin Bridge Road, Winchester, NH	0.95	Single-Family Home	$350,700	07/07/26	4	2	1,750
82 Howard Street, Winchester, NH	1.33	Single-Family Home	$285,000	07/13/26	3	2	1,100
56 Melvin Bridge Road, Winchester, NH	1.08	Single-Family Home	$280,000	11/04/25	3	1	1,295

Nearby homes

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

Skip to last item

FOR SALE
$720,000
2 bd
1.5 ba
1,351 sqft
27 Headlands Road,
Winchester, NH 03470
PrimeMLS, Active
SOLD
SEP 26, 2025
$360,000
1 bd
1 ba
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25 Headlands Road,
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PrimeMLS, Closed
SOLD
JAN 23, 2026
$100,000
7 Lake Shore Drive,
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OFF MARKET
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306 Forest Lake Road,
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FOR SALE
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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 39 Headlands Road.

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 39 Headlands Road.

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.
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
Flag

LGBTQ Local Legal Protections

Nancy S Panza, BHG Masiello Keene, (603) 352-5433

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 2026-07-22 14:03:44 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.

39 Headlands Road, Winchester, NH 03470 is a 3 bedroom, 2 bathroom, 1,364 sqft single-family home built in 1910. This property is currently available for sale and was listed by PrimeMLS on May 6, 2026. The MLS # for this home is MLS# 5087379.

39 Headlands Road
Winchester, NH 03470

$698,000