38 Chestnut Dr, Windsor, CT 06095
Property image
Property image
OFF MARKET

$355,200

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,540 sqft (on 0.52 acres)

38 Chestnut Dr, Windsor, CT 06095

Est. Refi. Payment $2,681/mo*
Refinance Your Home
Currently Off Market - Sold Jun 29, 2020 for $227,000

Home Value

Trulia Estimate
$355K
Since last month
Decreased$7K (-1.9%)
Since last year
Increased$5K (+1.5%)
Since last sale
Increased$128K (+56.5%)
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 +91% in the last 10 years
MonthEstimated value
2026
October 2026$355K
September 2026$361K
August 2026$362K
July 2026$360K
June 2026$366K
May 2026$367K
April 2026$355K
March 2026$352K
February 2026$336K
January 2026$339K
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
41 Chestnut Drive, Windsor, CT
0.05
Single-Family Home
$250,000
02/13/26
2
2
1,452
26 Hickory Drive, Windsor, CT
0.10
Single-Family Home
$365,000
01/29/26
3
2
1,943
16 Landing Circle, Windsor, CT
0.27
Single-Family Home
$500,000
02/27/26
3
2.5
2,237
740 Rainbow Road, Windsor, CT
0.31
Single-Family Home
$320,000
06/15/26
2
2
1,444
351 Rainbow Road, Windsor, CT
0.75
Single-Family Home
$315,000
12/05/25
4
2
2,520
220 Castlewood, Windsor, CT
1.06
Single-Family Home
$370,500
01/07/26
3
1.5
1,484
36 High Street, Windsor, CT
1.10
Single-Family Home
$425,000
10/31/25
3
2
1,294
158 Winterwood, Windsor, CT
1.15
Single-Family Home
$406,000
11/12/25
3
2.5
1,894
1 Walter's Way, Windsor, CT
0.38
Single-Family Home
$553,000
08/18/26
4
3.5
3,552
19 Rainbow Creek, Windsor, CT
1.12
Single-Family Home
$456,000
02/03/26
3
2.5
1,904

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
42 Chestnut Dr, Windsor, CT 06095
0.02
$350,600
2
2
1,455
Off Market
34 Chestnut Drive, Windsor, CT 06095
0.02
$374,300
3
2.5
1,784
Off Market
30 Chestnut Drive, Windsor, CT 06095
0.04
$314,000
3
1.5
1,204
Off Market
46 Chestnut Dr, Windsor, CT 06095
0.04
$298,300
2
2
1,186
Off Market
35 Hickory Dr, Windsor, CT 06095
0.04
$284,400
3
2
1,259
Off Market
31 Hickory Dr, Windsor, CT 06095
0.05
$326,500
3
2
1,306
Off Market
39 Hickory Dr, Windsor, CT 06095
0.05
$323,200
3
2
1,454
Off Market
41 Chestnut Drive, Windsor, CT 06095
0.05
$250,000
2
2
1,452
Recently Sold
37 Chestnut Dr, Windsor, CT 06095
0.06
$291,000
2
3
1,277
Off Market
43 Hickory Dr, Windsor, CT 06095
0.06
$340,900
3
1.5
1,152
Off Market
26 Chestnut Dr, Windsor, CT 06095
0.06
$278,800
2
1
800
Off Market
27 Hickory Dr, Windsor, CT 06095
0.06
$323,100
3
1
1,377
Off Market
33 Chestnut Dr, Windsor, CT 06095
0.06
$367,000
3
3
1,340
Off Market
52 Chestnut Dr, Windsor, CT 06095
0.06
$392,800
3
2
1,468
Off Market
45 Chestnut Dr, Windsor, CT 06095
0.07
$334,900
3
2
1,125
Off Market
29 Chestnut Dr, Windsor, CT 06095
0.07
$284,400
3
1
1,144
Off Market
21 Hickory Dr, Windsor, CT 06095
0.07
$286,400
3
1
1,172
Off Market
22 Chestnut Dr, Windsor, CT 06095
0.08
$289,200
3
1
1,225
Off Market
56 Chestnut Dr, Windsor, CT 06095
0.08
$305,000
3
1
1,265
Off Market
30 Cedar Rd, Windsor, CT 06095
0.09
$281,700
3
2
1,162
Off Market

Local Information

  • Map ViewExplore the area around 38 Chestnut Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1955
0.52 acre lot
1,540 sqft
$231/sqft

About this House

Come and make this very well maintained Cape your New Home! Located in beautiful Windsor, on a half acre, with nearby parks, lake, river, and more. The first floor features a sun room with vaulted ceiling, kitchen, bedroom, full bathroom and formal dining room and living room. On the second floor you will find your master bedroom along with two additional bedrooms for office or guest room and an another full bathroom. Additional two room in the basement along with the laundry room and brand new furnace . Listen to the symphony of the breeze dancing through your backyard or watch the incredible bird life from your deck. Don't miss this great opportunity with a very enchanting house filled with nice surprises to discover.
38 Chestnut Dr, Windsor, CT 06095 is a 3 bedroom, 2 bathroom, 1,540 sqft single-family home built in 1955. It last sold for $227,000 on Jun 29, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $355,200, with a rent estimate of $2,774/month.

Home Details for 38 Chestnut Dr

Interior Features

Heating & Cooling
Heating: Baseboard, Electric, OilAir ConditioningHeating Fuel: Baseboard
Interior Details
Number of Rooms: 8Ceiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Vinyl, Cement ConcretePatioPorch

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.52 acres

Price and Tax history

DateEventPrice
Jun 29, 2020
Source: Smart MLS #170290755
Sold
$227,000
May 10, 2020
Source: Agent Provided
Pending
$229,000
Apr 29, 2020
Source: Agent Provided
Listed For Sale
$229,000
Nov 3, 2017
Source: Smart MLS #G10222844
Sold
$189,000
Aug 7, 2017
Source: Agent Provided
PriceChange
$189,000
Price decreased by 5%

Market trends in Windsor

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$398K
$38.17KMoM
Sale-to-List Price
—
Price per sq ft
$214
$2MoM
Available listings
64
9MoM

Around this home

What Locals Say about Windsor

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 70% say there's holiday spirit
  • 67% say there are sidewalks
  • 55% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
At least 159 Trulia users voted on each feature.

  • 89 % Say car is needed

  • 88 % Say parking is easy

  • 87 % Say it's dog friendly

  • 78 % Say streets are well-lit

  • 77 % Say yards are well-kept

  • 74 % Say people would walk alone at night

  • 70 % Say there's holiday spirit

  • 69 % Say there's wildlife

  • 69 % Say it's quiet

  • 67 % Say there are sidewalks

  • 65 % Say kids play outside

  • 55 % Say neighbors are friendly

  • 53 % Say they plan to stay for at least 5 years

  • 46 % Say it's walkable to restaurants

  • 46 % Say it's walkable to grocery stores

  • 34 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Keyonna
    "Quiet and everyone keeps to themselves. Only a little noisy during the summer time due to motorcycles."
    0
    Flag
  • Zonoui Smith Jr.
    "I see dogs walked all the time. Some people don’t pick up after them. Also some people let their dogs walk to far into residence yards to use the bathroom "
    0
    Flag
  • Fenn.nathaniel
    "I've lived in this neighbourhood for about 15 years in love that is close to everything and far away from the hustles and bustles of the city."
    10
    Flag
  • Sherianne10315
    "Windsor has a small town feel. People help each other and come together when others are in need. Local farms and shop owners are friendly."
    0
    Flag
  • Kimberlydbigelow
    "I have lived in Windsor for 5 years. It has been the perfect location! I work in downtown Hartford and I take the bus into the city from a commuter lot in my town. It’s a relaxing 15min ride into and out of Hartford and as close as I am to the capital, Windsor is cute with lots of farms and the small, quaint town feel I was looking for. I’m loving it!"
    1
    Flag
  • Unspecified
    "Lots of town activities! Stuff on the green, local businesses, small town feel! Diverse community and polite town members"
    1
    Flag
  • Unspecified
    "There are Town green events all the time! Numerous walking trails filled with people. Strong sense of community. Working with locals is the norm in terms of hiring services."
    0
    Flag
  • Ashley W.
    "Los of people outside walking and a very quiet area very close to the highway. Good sense of community very safe and friendly neighborhood. Can walk to gas or food and close to the center of town and a lot of schools too!"
    0
    Flag
  • G.girardin
    "It’s a friendly and diversified neighborhood. Great walking neighborhood even at night. We’ve lived in Windsor for 35 years and feel very safe here. This is our third neighborhood . We’ve never had any issues. "
    0
    Flag
  • Sarah L.
    "Poquonock school is a wonderful community all the parks are very safe and the parks & rec programs are great"
    0
    Flag
  • Sam B.
    "Great place to stay and bring up a family great school system whatever they are ranked now you have Amazon JCP and others job market is good Parks swimming pools library good shop name it and you have it"
    0
    Flag
  • Sam B.
    "Great place to live grow work Bus and Uber available Mixed crowd Friendly people Great schools Parks pools Best library "
    0
    Flag
  • Sam B.
    "Great place to raise a family schools transport parks people are all great Town have a lot of activity like Shad Derby"
    0
    Flag
  • Shyra E.
    "My neighborhood is amazing it has good transit access and wonderful restaurants and parks hope this helps"
    0
    Flag
  • Carol J. M.
    "I live in this area for 1 year in a 55 and over community and love it! Lots of traffic on 91 and 291 that I do not like."
    1
    Flag
  • Nbjackson
    "Usually on the town green, farmers market, summer outdoor concerts, parades, Halloween event, holiday events, craft fairs"
    0
    Flag
  • Bonny E.
    "Yes dogs are always being walked in this area. They are great here. Kids always playing too. Neighbors helping neighbors. People look out for each other"
    0
    Flag
  • Jeffery I.
    "There are many events and good parks in town. however, you need the spend time finding them. unless you have lived hear for a long time or are active in town it can be hard to find stuff to do."
    0
    Flag
  • Me
    "my neighborhood is awesome, quiet, clean, with sidewalks, and walking trails. The HOA takes care of all the grounds maintenance and all snow removal"
    1
    Flag
  • Angie R.
    "recreation Dept has great programs parks are well maintained school system is getting back on track great family friendly town"
    0
    Flag
  • Me
    "Windsor is a small town. Although there are some rough areas but overall its quiet and safe. Schools are subpart.and taxes are high"
    1
    Flag
  • Wendy S.
    "during the summer they have concerts on the green down town. nice place tp live. quite contry living"
    0
    Flag
  • Me
    "I have lived here for 12 and I am very happy. the neighborhood is quiet and safe the streets are clean and well light"
    0
    Flag
  • ReginaJ
    "Live in the harvest Lane neighborhood for the last 9 years. One of the best places to live in the state. A very sort after neighborhood to live. Took us a while to get a house, because no one moves from it. Unless they are retiring and moving to Florida. The trails that are connected off the street that leads to Northwest Park and the reservoir for hiking are incredible. The family atmosphere is that of an extended family. The kids, the parents even the pets all know each other. We can’t ask for more from such a tranquil place we live in with so much harmony and love. #HarvestLane4Life "
    0
    Flag
  • Amy C.
    "Windsor is a town with strong resources and traditions. It has reasonable housing prices and lots of diversity. "
    0
    Flag
  • Carol J. M.
    "We have coffee 9am - 11am once a month and other social events. Dog friendly. Neighbors are very friendly."
    0
    Flag
  • Shanyelle.hamilton
    "Public transportation is easily accessible and downtown Hartford is 15 minutes from Wilson and 30 minutes from the town center by bus or car."
    0
    Flag
  • Shanyelle.hamilton
    "There are plenty of family friendly events in Windsor or the surrounding area. Every Halloween we have Nightmare on Broad Street for kids of all ages to have safe fun."
    0
    Flag
  • Lisanickersondouglas
    "Great schools / diverse community. Easy highway access. Lots of parks and trails for walking. Many annual events for kids and families. "
    0
    Flag
  • Amani R.
    "We have a yearly block party at each of the local parks. They are usually well attended and snacks are provided. "
    0
    Flag
  • Gchekas
    "Short commute, less than five minutes to work. Lot of industry on Day Hill Road, plenty of work for manufacturing industry. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 38 Chestnut Dr

  • What is 38 Chestnut Dr estimated to be worth?
    Trulia's estimated value for 38 Chestnut Dr in Windsor, CT is $355,200.
  • What is the price history for 38 Chestnut Dr?
    38 Chestnut Dr in Windsor, CT last sold for $227,000 in June 2020.
  • Is Windsor a buyer's or seller's market?
    Windsor is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Windsor?
    The median sale price in Windsor is $398K. That is up $38.17K from the prior month.
  • Does 38 Chestnut Dr have laundry facilities?
    Yes, 38 Chestnut Dr in Windsor, CT has in-unit laundry.
  • How big is the lot at 38 Chestnut Dr?
    The lot at 38 Chestnut Dr in Windsor, CT is about 0.52 acres (22,651 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 38 Chestnut Dr

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