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

38 Chestnut Dr
Windsor, CT 06095

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

$360,600

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $2,572/mo*
Refinance Your Home

$360,600

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $2,572/mo*
Refinance Your Home
3 Beds
2 Baths
1,540 sqft
(on 0.52 acres)

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

Property Type
Single-Family Home
Year Built
1955
Lot Size
0.52 acres
Living Area
1,540 sqft
Price/Sqft
$234

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. It is currently off market. The Trulia Estimate is $360,600, with a rent estimate of $2,709/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 History for 38 Chestnut Dr

DatePriceEventSource
06/29/2020$227,000Sold
Smart MLS #170290755
05/10/2020$229,000PendingAgent Provided
04/29/2020$229,000Listed For SaleAgent Provided
11/03/2017$189,000Sold
Smart MLS #G10222844
08/07/2017$189,000PriceChange
Agent Provided
06/26/2017$199,000Listed For SaleAgent Provided
08/18/2013$209,900ListingRemovedAgent Provided
07/24/2013$209,900PriceChange
Agent Provided
06/27/2013$211,900PriceChange
Agent Provided
06/02/2013$217,900PriceChange
N/A
02/15/2013$229,900Listed For SaleN/A
10/28/2004$187,000Sold
N/A

Market trends in Windsor

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$336K
$27.63KMoM
Sale-to-List Price
—
Price per sq ft
$214
$3MoM
Available listings
60
3MoM
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Property Tax and Assessment

Year2025
Tax$5,692
Assessment$200,060
Home facts updated by county records

Comparable Sales for 38 Chestnut Dr

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
19 Rainbow Creek, Windsor, CT
1.12
Single-Family Home
$456,000
02/03/26
3
2.5
1,904
39 Loren Circle, Windsor, CT
1.32
Single-Family Home
$339,000
07/31/26
4
2
2,402

Nearby homes

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Assigned Schools

These are the assigned schools for 38 Chestnut Dr.
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 Windsor

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
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Apartments for Rent

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Explore by feature - Air Conditioning

Explore by feature - Washer/dryer

8 rentals with a washer/dryer in Windsor, CT

Homes for sale near 38 Chestnut Dr

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Off Market Homes Near 38 Chestnut Dr

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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 $360,600.
  • 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 $336K. That is down $27.63K 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).