166 Keene Road, Winchester, NH 03470
Property image
Property image
FOR SALE
4.3 ACRES
Listed by Jamie Smith, BHG Masiello Keene, (603) 352-5433

$449,900

Original price: $479,900
  • 3 Beds
  • 1.5 Baths
  • 1,808 sqft (on 4.30 acres)

166 Keene Road, Winchester, NH 03470

Est. Mortgage $3,100/mo*
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Home Highlights

Single-Family Home
Built in 1800
4.3 acre lot
$249/sqft

Local Information

  • Map ViewExplore the area around 166 Keene Road.
  • Schools1 Preschool School1 Elementary School1 Middle School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Welcome to 166 Keene Road in Winchester, a charming 3-bedroom, 1.5-bath New Englander that combines classic character with thoughtful modern updates. This inviting home offers comfortable living spaces, abundant natural light, and a warm atmosphere that immediately feels like home. Recent improvements include an updated roof, solar panels for enhanced energy efficiency, a spacious back deck ideal for entertaining and outdoor enjoyment, fresh paint throughout the interior, updated light fixtures, and a new dishwasher, allowing the next owner to move in with confidence. The functional floor plan provides flexibility for everyday living, whether you're gathering with family, working from home, or hosting friends. Outside, enjoy the benefits of outdoor living from the rear deck or wrap around front porch, perfect for summer barbecues, morning coffee, or simply relaxing while taking in the surroundings. The solar system helps reduce energy costs while adding long-term value and sustainability. 465' of frontage on Ashuelot River. Conveniently located with easy access to local amenities, schools, shopping, dining, and recreational opportunities, this property offers the perfect balance of small-town New Hampshire living and modern convenience. Easy commute to Keene, Mass, Brattleboro and Interstate 91.

Home Details for 166 Keene Road

Active Status

MLS Status: Active

Interior Features

Interior Details
Basement: Concrete Floor,Full,Unfinished,Interior Access,Interior EntryNumber of Rooms: 5
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1808 Square Feet
Appliances & Utilities
Utilities: CableAppliances: Dishwasher, Dryer, Double Oven, Refrigerator, Washer, Oil Water Heater, Instant Hot WaterDishwasherDryerLaundry: In BasementRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,Mini Split,BoilerHas CoolingAir Conditioning: Mini SplitHas HeatingHeating Fuel: Hot Water
Gas & Electric
Electric: 200+ Amp Service, Circuit Breakers
Windows, Doors, Floors & Walls
Flooring: Hardwood, Tile
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Hardwood, Tile
View
No View

Exterior Features

Exterior Home Features
Roof: Asphalt ShinglePatio / Porch: PorchOther Structures: Barn(s)Exterior: DeckFoundation: Stone
Parking & Garage
No GarageParking: Gravel
Frontage
WaterfrontResponsible for Road Maintenance: Public Maintained RoadOn Waterfront
Water & Sewer
Sewer: Public SewerWater Body: Ashuelot River
Farm & Range
Frontage Length: Water frontage: 465, Road frontage: 484
Finished Area
Finished Area (above surface): 1808 Square Feet

Days on Market

Days on Market: 99

Property Information

Year Built
Year Built: 1800
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: New Englander
Building
Construction Materials: Wood Frame, Clapboard Exterior, Wood SidingNot a New Construction

Price & Status

Price
List Price: $449,900Price Per Sqft: $249

Location

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

Agent Information

Listing Agent
Listing ID: 5092617

Building

Building Area
Building Area: 2712 Square Feet

Lot Information

Lot Area: 4.3 Acres

Miscellaneous

BasementMls Number: 5092617Above Grade Unfinished Area: 1808Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 904Below 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 July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
15
1MoM

Home Value

Trulia Estimate
$443K
Since last month
Decreased$21K (-4.5%)
Since last year
Increased$115K (+34.9%)
Since last sale
Increased$258K (+139.3%)
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 +187% in the last 10 years
MonthEstimated value
2026
September 2026$443K
August 2026$461K
July 2026$464K
June 2026$488K
May 2026$337K
April 2026$332K
March 2026$323K
February 2026$308K
January 2026$304K
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
82 Howard Street, Winchester, NH
0.40
Single-Family Home
$290,000
07/13/26
3
2
1,100
12 Miner Court, Winchester, NH
0.57
Single-Family Home
$259,000
12/30/25
3
1
1,416
56 Ashuelot Street, Winchester, NH
0.98
Single-Family Home
$143,000
12/31/25
3
2
3,390
96 Old Spofford Road, Winchester, NH
0.75
Single-Family Home
$321,000
10/31/25
2
1
960
26 Mechanic Street, Winchester, NH
0.54
Single-Family Home
$377,000
07/21/26
4
2.5
2,736
10 Swan Street, Winchester, NH
1.11
Single-Family Home
$305,000
03/31/26
3
1
1,689
50 Parker Street, Winchester, NH
1.03
Single-Family Home
$304,000
01/05/26
4
1.5
2,535
71 Parker Street, Winchester, NH
1.12
Single-Family Home
$277,000
03/20/26
3
1
1,372
62 Parker Street, Winchester, NH
1.07
Single-Family Home
$430,000
07/29/26
4
1.5
2,252
56 Melvin Bridge Road, Winchester, NH
1.23
Single-Family Home
$280,000
11/04/25
3
1
1,295

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
161 Keene Road, Winchester, NH 03470
0.04
$263,200
3
2
1,662
Off Market
36 Wedgewood Drive, Winchester, NH 03470
0.14
$277,100
3
1
1,328
Off Market
128 Keene Road, Winchester, NH 03470
0.19
$227,100
3
1.5
1,320
Off Market
111 Howard Street, Winchester, NH 03470
0.30
$316,700
3
1
1,602
Off Market
97 Howard Street, Winchester, NH 03470
0.32
$383,900
4
2
1,484
Off Market
76 Mechanic Street, Winchester, NH 03470
0.32
$240,900
4
1
1,918
Off Market
99 Keene Road, Winchester, NH 03470
0.33
-
4
3
1,881
Off Market
102 Keene Road, Winchester, NH 03470
0.33
$220,800
3
1.5
3,603
Off Market
57 Old Westport Road, Winchester, NH 03470
0.38
$337,700
3
2
1,719
Off Market
82 Howard Street, Winchester, NH 03470
0.40
$290,000
3
2
1,100
Recently Sold
38 Mechanic Street, Winchester, NH 03470
0.49
$206,600
3
1
1,602
Off Market

Price and Tax history

DateEventPrice
Aug 31, 2026
Source: PrimeMLS #5092617
PriceChange
$449,900
Price decreased by 6%
Jul 19, 2026
Source: PrimeMLS #5092617
PriceChange
$479,900
Price decreased by 4%
Jun 3, 2026
Source: PrimeMLS #5092617
Listed For Sale
$499,900
Apr 28, 2020
Source: N/A
Sold
$185,000
May 1, 2011
Source: Agent Provided
ListingRemoved
$55,000

LGBTQ Local Legal Protections

Jamie Smith, 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 2026-09-10 14:13:46 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 166 Keene Road

  • What is the estimated monthly payment for 166 Keene Road?
    Based on a $449,900 list price with 20% down at today's rates, the estimated monthly payment for 166 Keene Road in Winchester, NH is approximately $3,199 (about $2,419 principal & interest, $705 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 166 Keene Road?
    The closest schools to 166 Keene Road in Winchester, NH are Winchester School (Pre-K/Elementary/Middle, rated 3/10).
  • What is 166 Keene Road estimated to be worth?
    Trulia's estimated value for 166 Keene Road in Winchester, NH is $442,700.
  • Does 166 Keene Road have air conditioning?
    Yes, 166 Keene Road in Winchester, NH has air conditioning.
  • Does 166 Keene Road have laundry facilities?
    Yes, 166 Keene Road in Winchester, NH has in-unit laundry.
166 Keene Road, Winchester, NH 03470 is a 3 bedroom, 2 bathroom, 1,808 sqft single-family home built in 1800. This property is currently available for sale and was listed by PrimeMLS on Jun 3, 2026. The MLS # for this home is MLS# 5092617.