71 Headlands Road, Winchester, NH 03470
Property image
Property image
FOR SALE
0.39 ACRES
Listed by Anna Schierioth, HKS Associates, Inc., (603) 352-6030

$445,000

Original price: $495,000
  • 3 Beds
  • 2 Baths
  • 1,066 sqft (on 0.39 acres)

71 Headlands Road, Winchester, NH 03470

Est. Mortgage $3,067/mo*
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Home Highlights

Single-Family Home
Built in 1928
0.39 acre lot
$417/sqft

Local Information

  • Map ViewExplore the area around 71 Headlands Road.
  • Schools1 Preschool School1 Elementary School1 Middle School
  • Shop & Eat
-- mins to
Commute Destination

About this House

This year-round lakefront retreat offers 100 feet of shoreline on Forest Lake and combines comfort, character, and stunning water views. Relax on the enclosed porch or one of several decks while enjoying the peaceful lakeside setting. The open-concept living and dining area features a pellet stove and abundant windows that capture beautiful lake views throughout the seasons. Outdoor living takes center stage, whether you're enjoying your morning coffee on the porch, entertaining on the decks, or spending the day on the water. A separate mobile home that has not been used for some time and could potentially serve as a guest cottage or private accommodation for family and visitors. It includes a living room, kitchen with pantry, bedroom, bathroom, attached shed, its own septic system, and a wood stove ready for hookup. Whether you're seeking a year-round residence, vacation getaway, or a property with space for extended family and guests, this unique waterfront offering provides the perfect blend of tranquility, recreation, and lakeside living.

Home Details for 71 Headlands Road

Active Status

MLS Status: Active

Interior Features

Interior Details
Number of Rooms: 7
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1066 Square Feet
Appliances & Utilities
Utilities: CableAppliances: Dryer, Washer, Electric Water HeaterDryerWasher
Heating & Cooling
Heating: Pellet Stove,ElectricHas CoolingAir Conditioning: Wall Unit(s)Has HeatingHeating Fuel: Pellet Stove
Fireplace & Spa
Number of Fireplaces: 1Fireplace: 1 FireplaceHas a Fireplace
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Flooring: Carpet
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Enclosed PorchOther Structures: Guest House, OutbuildingExterior: Deck, Natural Shade, ShedFoundation: Concrete
Parking & Garage
No CarportNo GarageParking: Gravel,Permit Required
Frontage
WaterfrontRoad Frontage: Private RoadOn Waterfront
Water & Sewer
Sewer: Private SewerWater Body: Forest Lake
Farm & Range
Frontage Length: Water frontage: 100, Road frontage: 88
Finished Area
Finished Area (above surface): 1066 Square Feet

Days on Market

Days on Market: 77

Property Information

Year Built
Year Built: 1928
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Bungalow
Building
Construction Materials: Wood Frame, Asbestos Exterior, Shingle SidingNot a New Construction

Price & Status

Price
List Price: $445,000Price Per Sqft: $417

Location

Direction & Address
City: Winchester
School Information
Elementary School: Winchester SchoolElementary School District: Winchester School DistrictJr High / Middle School: Winchester SchoolJr High / Middle School District: Winchester School DistrictHigh School: Keene High SchoolHigh School District: Winchester School District

Agent Information

Listing Agent
Listing ID: 5096976

Building

Building Area
Building Area: 1174 Square Feet

Lot Information

Lot Area: 0.39 acres

Miscellaneous

Mls Number: 5096976Water ViewWater View: WaterAbove Grade Unfinished Area: 1066Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

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

Market trends in Winchester

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

Home Value

Trulia Estimate
$437K
Since last month
Increased$5K (+1.2%)
Since last year
Decreased$70K (-13.8%)
Since last sale
Increased$214K (+96.1%)
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 +156% in the last 10 years
MonthEstimated value
2026
September 2026$437K
August 2026$429K
July 2026$432K
June 2026$507K
2021
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
45 Forest Lake Circle, Winchester, NH
0.41
Single-Family Home
$355,000
03/20/26
4
2
1,500
49 Forest Lake Circle, Winchester, NH
0.43
Single-Family Home
$330,000
07/31/26
2
1
937
25 Headlands Road, Winchester, NH
0.14
Single-Family Home
$360,000
09/26/25
1
1
756
73 Lake Shore Drive, Winchester, NH
0.13
Single-Family Home
$729,900
01/06/26
4
3
2,975
82 Howard Street, Winchester, NH
1.24
Single-Family Home
$290,000
07/13/26
3
2
1,100
56 Melvin Bridge Road, Winchester, NH
1.01
Single-Family Home
$280,000
11/04/25
3
1
1,295
30 Melvin Bridge Road, Winchester, NH
0.88
Single-Family Home
$350,700
07/07/26
4
2
1,750
220 Richmond Road, Winchester, NH
1.55
Single-Family Home
$265,000
10/10/25
2
1.5
1,220
19 Toofs Drive, Winchester, NH
1.58
Single-Family Home
$295,000
02/27/26
3
2
1,344
12 Miner Court, Winchester, NH
1.43
Single-Family Home
$259,000
12/30/25
3
1
1,416

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
0.13
$729,900
4
3
2,975
Recently Sold
27 Headlands Road, Winchester, NH 03470
0.14
$715,000
2
1.5
1,351
For Sale
25 Headlands Road, Winchester, NH 03470
0.14
$363,700
1
1
756
Off Market
7 Lake Shore Drive, Winchester, NH 03470
0.15
$100,000
-
-
-
Recently Sold
306 Forest Lake Road, Winchester, NH 03470
0.19
$420,500
3
2
1,755
Off Market
370 Forest Lake Road, Winchester, NH 03470
0.21
$469,500
-
-
-
Off Market
372 Forest Lake Road, Winchester, NH 03470
0.25
$345,200
2
1
820
Off Market
20 Whitcomb Court, Winchester, NH 03470
0.30
$603,700
2
1
1,252
Off Market
162 Upper Headlands Road, Winchester, NH 03470
0.37
-
-
-
-
Off Market
45 Forest Lake Circle, Winchester, NH 03470
0.41
$355,000
4
2
1,500
Recently Sold
49 Forest Lake Circle, Winchester, NH 03470
0.43
$330,000
2
1
937
Recently Sold

Price and Tax history

DateEventPrice
Jul 14, 2026
Source: PrimeMLS #5096976
PriceChange
$445,000
Price decreased by 10%
Jun 26, 2026
Source: PrimeMLS #5096976
Listed For Sale
$495,000
Jul 31, 2003
Source: N/A
Sold
$223,000
Oct 5, 2001
Source: N/A
Sold
$190,000

LGBTQ Local Legal Protections

Anna Schierioth, HKS Associates, Inc., (603) 352-6030
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 2026-09-12 00:34:02 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.

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Frequently asked questions about 71 Headlands Road

  • What is the estimated monthly payment for 71 Headlands Road?
    Based on a $445,000 list price with 20% down at today's rates, the estimated monthly payment for 71 Headlands Road in Winchester, NH is approximately $3,176 (about $2,404 principal & interest, $697 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • 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 homes for sale in Winchester, NH.
  • What are the closest schools to 71 Headlands Road?
    The closest schools to 71 Headlands Road in Winchester, NH are Winchester School (Pre-K/Elementary/Middle, rated 3/10).
  • What is 71 Headlands Road estimated to be worth?
    Trulia's estimated value for 71 Headlands Road in Winchester, NH is $437,200.
  • Does 71 Headlands Road have air conditioning?
    Yes, 71 Headlands Road in Winchester, NH has air conditioning.
  • Does 71 Headlands Road have laundry facilities?
    Yes, 71 Headlands Road in Winchester, NH has in-unit laundry.
71 Headlands Road, Winchester, NH 03470 is a 3 bedroom, 2 bathroom, 1,066 sqft single-family home built in 1928. This property is currently available for sale and was listed by PrimeMLS on Jun 26, 2026. The MLS # for this home is MLS# 5096976.