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

What is the price history for 100 Main Street?

100 Main Street in Winchester, NH last sold for $202,500 in December 2025.

Is Winchester a buyer's or seller's market?

Winchester is currently a balanced 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 100 Main Street?

The closest schools to 100 Main Street in Winchester, NH are Winchester School (Pre-K/Elementary/Middle, rated 3/10).

Does 100 Main Street have air conditioning?

Yes, 100 Main Street in Winchester, NH has air conditioning.

SOLD

DEC 23, 2025

Listed by Vincent Dolan, RE/MAX Town & Country, (603) 357-4100 . Bought with The Neighborhood Realty Group

$202,500

Last sold price

Studio
2 Baths
1,516 sqft

100 Main Street, Winchester, NH 03470

Refinance Your Home

Currently Off Market - Sold Dec 23, 2025 for $202,500 (6% below list price)

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
12 Mechanic Street, Winchester, NH	0.32	Multi-Family Home	$240,000	06/12/26	4	1	1,772
15 High Street, Winchester, NH	0.18	Multi-Family Home	$550,000	08/06/26	10	8	4,519
406 Back Ashuelot Road, Ashuelot, NH	1.96	Multi-Family Home	$535,000	07/27/26	7	5	5,321
14 Stearns Court, Hinsdale, NH	5.08	Multi-Family Home	$470,000	04/03/26	27	4	3,060
719 Mount Hermon Station Rd, Northfield, MA	5.17	Multi-Family Home	$358,000	04/21/26	4	2	2,292
523 Chesterfield Road, Hinsdale, NH	6.10	Multi-Family Home	$250,000	09/08/26	4	2	1,456
28 Christian Hill Road, Swanzey, NH	7.48	Multi-Family Home	$310,000	08/25/26	5	2	1,870

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
94 Main Street, Winchester, NH 03470	0.02	-	4	2	3,240	Off Market
23 Ashuelot Street, Winchester, NH 03470	0.07	-	4	4	2,484	Off Market
27 Ashuelot Street, Winchester, NH 03470	0.07	-	6	2	3,300	Off Market
30 Ashuelot Street, Winchester, NH 03470	0.09	$178,900	3	1	1,622	Off Market
11 Ashuelot Street, Winchester, NH 03470	0.06	-	Studio	3	4,226	Off Market
26 Elm Street, Winchester, NH 03470	0.11	$269,900	4	1	1,864	Off Market
6 Cedar Lane, Winchester, NH 03470	0.15	$115,000	3	2	927	Recently Sold
21 Richmond Road, Winchester, NH 03470	0.15	-	3	2	2,624	Off Market
56 Ashuelot Street, Winchester, NH 03470	0.20	$143,000	3	2	3,390	Recently Sold
3 Dogwood Hill Road, Winchester, NH 03470	0.19	$74,000	3	1	924	Off Market
2 Lilac Lane, Winchester, NH 03470	0.19	$78,600	2	2	1,008	Off Market

Local Information

Map ViewExplore the area around 100 Main Street.
Schools1 Preschool School1 Elementary School1 Middle School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Multi-Family

Built in 1850

1,516 sqft

$134/sqft

About this House

What's unique:Laundry hookupsModern kitchens

RENOVATED In Town 2 Family. Located directly on Main Street this duplex is super convenient. Turn key. Move in and have tenant income or list as Airbnb property. Modern Kitchens and Bathrooms, Laundry hookups in North Unit and Combination Washer/Dryer appliance in South Unit.

100 Main Street, Winchester, NH 03470 is a studio, 1,516 sqft multi-family built in 1850. It last sold for $202,500 on Dec 23, 2025 (6% below the $215,000 asking price). More recently, it was listed as a rental in March 2012 with an asking price of $750 per month. That rental listing was removed on April 20, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $2,371/month.

Home Details for 100 Main Street

Interior Features
Interior Details Basement: Unfinished,Interior Entry
Beds & Baths Number of Bathrooms (full): 2
Dimensions and Layout Living Area: 1516 Square Feet
Appliances & Utilities Utilities: Cable AvailableAppliances: Electric Water Heater
Heating & Cooling Heating: Electric,Wall UnitsHas CoolingAir Conditioning: IndividualHas HeatingHeating Fuel: Electric
Gas & Electric Electric: Circuit Breakers
Windows, Doors, Floors & Walls Flooring: Combination, Hardwood, Vinyl
Levels, Entrance, & Accessibility Number of Stories: 2Levels: TwoFloors: Combination, Hardwood, Vinyl
View No View

Exterior Features
Exterior Home Features Roof: MembraneFoundation: Concrete, Stone
Parking & Garage No Garage
Frontage Waterfront: River FrontRoad Frontage: PublicRoad Surface Type: Paved
Water & Sewer Sewer: Public Sewer
Farm & Range Frontage Length: Road frontage: 27
Finished Area Finished Area (above surface): 1516 Square Feet

Property Information
Year Built Year Built: 1850
Property Type / Style Property Type: Residential IncomeProperty Subtype: Multi FamilyStructure Type: DuplexArchitecture: Duplex
Building Construction Materials: Wood FrameNot a New Construction

Price & Status
Price List Price: $215,000Price Per Sqft: $134/sqft

Active Status
MLS Status: Closed

Location
Direction & Address City: Winchester

Building
Building Area Building Area: 2092 Square Feet

Lot Information
Lot Area: 2614 sqft

Miscellaneous
BasementMls Number: 5062487Above Grade Unfinished Area: 1516Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 576Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Price and Tax history

Date	Event	Price
Dec 23, 2025 Source: PrimeMLS #5062487	Sold	$202,500
Sep 22, 2025 Source: PrimeMLS #5062487	Listed For Sale	$215,000
Apr 20, 2025 Source: Zillow Rentals	ListingRemoved	$1,500
Apr 8, 2025 Source: Zillow Rentals	PriceChange	$1,500 Price decreased by 98%
May 9, 2016 Source: N/A	Sold	$65,000
Jul 2, 2014 Source: Agent Provided	ListingRemoved	$69,900
Apr 22, 2014 Source: Agent Provided	Listed For Sale	$69,900
Mar 17, 2014 Source: N/A	Sold	$48,000
Dec 15, 2013 Source: Agent Provided	PriceChange	$69,900 Price decreased by 4%
Dec 6, 2013 Source: Agent Provided	Listed For Sale	$72,500
Oct 27, 2012 Source: Agent Provided	ListingRemoved	$79,000
Aug 10, 2012 Source: Agent Provided	PriceChange	$79,000 Price decreased by 7%
May 19, 2012 Source: Agent Provided	Listed For Sale	$85,000
Mar 15, 2012 Source: Agent Provided	Listed For Rent	$750
May 13, 2009 Source: N/A	Sold	$45,000
May 3, 2005 Source: N/A	Sold	$98,500

Year	Property tax	Tax assessment
2024	$2,147	$73,400

Additional Cost

Market trends in Winchester

Last updated August 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

Around this home

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

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
6y 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
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Angelica M.
Resident
7y 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

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 2026-09-23 10:55:15 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.

Frequently asked questions about 100 Main Street

What is the price history for 100 Main Street?
100 Main Street in Winchester, NH last sold for $202,500 in December 2025.
Is Winchester a buyer's or seller's market?
Winchester is currently a balanced 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 100 Main Street?
The closest schools to 100 Main Street in Winchester, NH are Winchester School (Pre-K/Elementary/Middle, rated 3/10).
Does 100 Main Street have air conditioning?
Yes, 100 Main Street in Winchester, NH has air conditioning.