149 Upper Headlands Rd, Winchester, NH 03470
OFF MARKET

$790,300

Trulia Estimate
  • 3 Beds
  • 4 Baths
  • 3,960 sqft (on 2 acres)

149 Upper Headlands Rd, Winchester, NH 03470

Est. Refi. Payment $5,389/mo*
Refinance Your Home

Home Value

Trulia Estimate
$790K
Since last month
Decreased$7K (-0.8%)
Since last year
Decreased$9K (-1.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +88% in the last 10 years
MonthEstimated value
2026
August 2026$790K
August 2026$790K
July 2026$797K
June 2026$785K
May 2026$780K
April 2026$756K
March 2026$749K
February 2026$738K
January 2026$738K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
Bed
Bath
Sqft
73 Lake Shore Drive, Winchester, NH
0.22
Single-Family Home
$729,900
01/06/26
4
3
2,975
30 Melvin Bridge Road, Winchester, NH
0.57
Single-Family Home
$350,700
07/07/26
4
2
1,750
45 Forest Lake Circle, Winchester, NH
0.28
Single-Family Home
$355,000
03/20/26
4
2
1,500
49 Forest Lake Circle, Winchester, NH
0.30
Single-Family Home
$330,000
07/31/26
2
1
937
56 Melvin Bridge Road, Winchester, NH
0.69
Single-Family Home
$280,000
11/04/25
3
1
1,295
25 Headlands Road, Winchester, NH
0.36
Single-Family Home
$360,000
09/26/25
1
1
756
510 Old Westport Road, Winchester, NH
1.34
Single-Family Home
$537,500
11/18/25
3
1.5
1,930
26 Mechanic Street, Winchester, NH
1.24
Single-Family Home
$377,000
07/21/26
4
2.5
2,736
82 Howard Street, Winchester, NH
1.27
Single-Family Home
$290,000
07/13/26
3
2
1,100
50 Parker Street, Winchester, NH
1.64
Single-Family Home
$304,000
01/05/26
4
1.5
2,535

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
162 Upper Headlands Road, Winchester, NH 03470
0.08
-
-
-
-
Off Market
73 Lake Shore Drive, Winchester, NH 03470
0.22
$729,900
4
3
2,975
Recently Sold
20 Whitcomb Court, Winchester, NH 03470
0.24
$603,700
2
1
1,252
Off Market
370 Forest Lake Road, Winchester, NH 03470
0.25
$469,500
-
-
-
Off Market
37 Town Beach Road, Winchester, NH 03470
0.29
$368,600
2
1
817
Off Market
45 Forest Lake Circle, Winchester, NH 03470
0.28
$355,000
4
2
1,500
Recently Sold
71 Headlands Road, Winchester, NH 03470
0.32
$445,000
3
2
1,066
For Sale
43 Town Beach Road, Winchester, NH 03470
0.30
$265,800
3
1
1,149
Off Market
49 Forest Lake Circle, Winchester, NH 03470
0.30
$330,000
2
1
937
Recently Sold
372 Forest Lake Road, Winchester, NH 03470
0.31
$345,200
2
1
820
Off Market
366 Keene Road, Winchester, NH 03470
0.33
$391,000
3
2
1,654
Off Market
25 Headlands Road, Winchester, NH 03470
0.36
$363,700
1
1
756
Off Market

Local Information

  • Map ViewExplore the area around 149 Upper Headlands Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1993
2 acre lot
3,960 sqft
$200/sqft
Garage

About this House

750 sq ft great room with wrap around glass of lake and woods. Kitchen recently updated with granite counter tops. 2 large bedrooms overlook the lake with pvt bathrooms. 3 rd bedroom has view of woods and bog with private bathroom. Large office/playroom overlook lake as well. Sunken library area on main floor next to massive dining room with fireplace. Lowest level has boat/lawn furniture, etc garage area on lowest level of home
149 Upper Headlands Rd, Winchester, NH 03470 is a 3 bedroom, 4 bathroom, 3,960 sqft single-family home built in 1993. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $790,300, with a rent estimate of $3,781/month.

Home Details for 149 Upper Headlands Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Office, Recreation RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, Stove, Electric, Oil, Propane Butane, Wood PelletAir ConditioningCooling System: WallHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Carpet, Linoleum Vinyl
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherDeckExterior: VinylGardenLawnPatioPorch
Parking & Garage
GarageParking: Off Street, Garage

Property Information

Year Built
Year Built: 1993
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Lot Information

Lot Area: 2.00 acres

Mobile R/V

RV Parking
Rv Parking

Price and Tax history

DateEventPrice
Sep 15, 2014
Source: Agent Provided
ListingRemoved
$695,000
Jun 6, 2014
Source: Agent Provided
Listed For Sale
$695,000

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
15
1MoM

Around this home

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

LGBTQ Local Legal Protections

Frequently asked questions about 149 Upper Headlands Rd

  • What is 149 Upper Headlands Rd estimated to be worth?
    Trulia's estimated value for 149 Upper Headlands Rd in Winchester, NH is $790,300.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a buyer's 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 149 Upper Headlands Rd?
    The closest schools to 149 Upper Headlands Rd in Winchester, NH are Winchester School (Pre-K/Elementary/Middle, rated 3/10).
  • Does 149 Upper Headlands Rd have air conditioning?
    Yes, 149 Upper Headlands Rd in Winchester, NH has air conditioning.
  • Does 149 Upper Headlands Rd have laundry facilities?
    Yes, 149 Upper Headlands Rd in Winchester, NH has in-unit laundry.

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 149 Upper Headlands Rd

Skip to last item
Skip to first item

Homes for sale near 149 Upper Headlands Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item