39 Chestnut St, Windsor, NY 13865
Property image
Property image
OFF MARKET

39 Chestnut St
Windsor, NY 13865

  • 2 Beds
  • 1 Bath
  • 1,162 sqft

$136,200

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $1,051/mo*

$136,200

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $1,051/mo*
2 Beds
1 Bath
1,162 sqft

Home Value

Trulia Estimate
$136K
Since last month
Increased$2K (+1.5%)
Since last year
Increased$16K (+13.5%)
Since last sale
Increased$65K (+92.4%)
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 +154% in the last 10 years
MonthEstimated value
2026
August 2026$135K
July 2026$133K
June 2026$134K
May 2026$132K
April 2026$130K
March 2026$128K
February 2026$125K
January 2026$121K
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
0.02
Single-Family Home
$87,538
12/10/25
2
1
1,075
0.76
Single-Family Home
$160,000
09/15/25
3
1
1,252
0.54
Single-Family Home
$174,900
12/02/25
4
2
1,640
0.12
Single-Family Home
$180,000
06/12/26
4
2
2,226
0.56
Single-Family Home
$50,000
09/29/25
5
2
2,269
0.76
Single-Family Home
$165,000
12/11/25
4
1.5
1,513
0.55
Single-Family Home
$185,000
12/15/25
4
1.5
2,776
0.82
Single-Family Home
$194,000
10/27/25
5
2
1,600
0.81
Single-Family Home
$25,000
10/03/25
3
2
2,040
1.39
Single-Family Home
$186,170
09/25/25
3
1
1,200

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
0.05
$290,000
4
2
1,500
For Sale
0.12
$180,000
4
2
2,226
Recently Sold
0.37
$95,000
3
2
1,456
Recently Sold
0.40
$338,500
4
3
2,844
Recently Sold
0.44
$199,000
3
1
3,320
For Sale
0.47
$135,400
3
2.5
1,970
Off Market
0.44
$649,000
-
-
-
For Sale
0.53
$190,000
5
2.5
1,696
For Sale
0.54
$139,600
3
1
1,423
Off Market
0.54
$245,500
4
1.5
2,040
For Sale
0.56
-
5
2
2,269
Off Market
0.54
$174,900
4
2
1,640
Recently Sold

Local Information

  • Map ViewExplore the area around 39 Chestnut St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1955
Living Area
1,162 sqft
Price/Sqft
$117
Parking
Garage

About this House

Beautifully maintained 2-3 bedroom Cape Cod.
39 Chestnut St, Windsor, NY 13865 is a 2 bedroom, 1 bathroom, 1,162 sqft single-family home built in 1955. It last sold for $70,000 on Oct 28, 2008. It is currently off market. The Trulia Estimate is $136,200, with a rent estimate of $1,554/month.

Home Details for 39 Chestnut St

Interior Features

Levels, Entrance, & Accessibility
Stories: 1.5
Interior Details
Number of Rooms: 5

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Exterior Features

Exterior Home Features
Exterior: Other
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price and Tax history

DateEventPrice
Apr 8, 2009
Source: Agent Provided
ListingRemoved
$71,900
Oct 28, 2008
Source: N/A
Sold
$70,000
Aug 31, 2008
Source: Agent Provided
Listed For Sale
$71,900
May 6, 1996
Source: N/A
Sold
$43,000
May 4, 1995
Source: N/A
Sold
$38,250

Market trends in Windsor

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
18
2
MoM

What Locals Say about Windsor

At least 10 Trulia users voted on each feature.
  • 94 % Say yards are well-kept

  • 93 % Say there's holiday spirit

  • 92 % Say parking is easy

  • 92 % Say kids play outside

  • 88 % Say it's dog friendly

  • 82 % Say car is needed

  • 82 % Say people would walk alone at night

  • 75 % Say there are community events

  • 74 % Say neighbors are friendly

  • 69 % Say it's walkable to grocery stores

  • 67 % Say it's quiet

  • 64 % Say they plan to stay for at least 5 years

  • 60 % Say there's wildlife

  • 56 % Say there are sidewalks

  • 47 % Say streets are well-lit

  • 21 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • NormBoGraham
    "I like this area, but it's lacking any real community feel. The schools are excellent. The area is very very "wet", but not swampy thus, if you build, be sure to include excellent drainage. Difficult to keep a basement dry, even on the hill. One house made the mistake of using a sump pump, thus, when tenants turned off the power, and heat, and left the home briefly....it distroyed the home, by freezing in the basement). Look at the willow trees....they are there because it's wet in the area. Windsor building rules are such, that I generally do things without a permit, because they get a bit excessive in their demands...(example: They require a special circuit breaker which is 5 times more expensive when the circuit goes to a bedroom). ie: replacing an old fuse box with circuit breakers makes things safer, but Windsor wants you to alter things unnecessarily. Windsor is a combination of expensive homes, and also dumps. "

LGBTQ Local Legal Protections

Frequently asked questions about 39 Chestnut St

  • What is 39 Chestnut St estimated to be worth?
    Trulia's estimated value for 39 Chestnut St in Windsor, NY is $136,200.
  • What is the price history for 39 Chestnut St?
    39 Chestnut St in Windsor, NY last sold for $70,000 in October 2008.
  • Is Windsor a buyer's or seller's market?
    Windsor is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Windsor?
    Residents describe Windsor, NY as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Windsor, NY.
  • How big is the lot at 39 Chestnut St?
    The lot at 39 Chestnut St in Windsor, NY is about 0.23 acres (10,018 sq ft).
  • Does 39 Chestnut St have a garage?
    Yes, 39 Chestnut St in Windsor, NY has a garage.

Apartments for Rent

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Off Market Homes Near 39 Chestnut St

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Homes for sale near 39 Chestnut St

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