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

11 Chestnut Dr
Windsor, CT 06095

  • 3 Beds
  • 2 Baths
  • 1,259 sqft (on 0.53 acres)

$338,500

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $2,413/mo*
Refinance Your Home

$338,500

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $2,413/mo*
Refinance Your Home
3 Beds
2 Baths
1,259 sqft
(on 0.53 acres)

Home Value

Trulia Estimate
$339K
Since last month
Increased$5K (+1.4%)
Since last year
Decreased$3K (-1%)
Since last sale
Increased$208K (+159.9%)
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 +94% in the last 10 years
MonthEstimated value
2026
August 2026$338K
July 2026$333K
June 2026$344K
May 2026$353K
April 2026$340K
March 2026$339K
February 2026$320K
January 2026$319K
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
0.14
Single-Family Home
$250,000
02/13/26
2
2
1,452
16 Landing Circle, Windsor, CT
0.15
Single-Family Home
$500,000
02/27/26
3
2.5
2,237
26 Hickory Drive, Windsor, CT
0.17
Single-Family Home
$365,000
01/29/26
3
2
1,943
740 Rainbow Road, Windsor, CT
0.18
Single-Family Home
$320,000
06/15/26
2
2
1,444
220 Castlewood, Windsor, CT
0.93
Single-Family Home
$370,500
01/07/26
3
1.5
1,484
351 Rainbow Road, Windsor, CT
0.79
Single-Family Home
$315,000
12/05/25
4
2
2,520
36 High Street, Windsor, CT
1.15
Single-Family Home
$425,000
10/31/25
3
2
1,294
1 Walter's Way, Windsor, CT
0.25
Single-Family Home
$553,000
08/19/26
4
3.5
3,552
158 Winterwood, Windsor, CT
1.02
Single-Family Home
$406,000
11/12/25
3
2.5
1,894
552 Stone Road, Windsor, CT
1.08
Single-Family Home
$300,000
01/16/26
3
1
1,128

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
710 Rainbow Road, Windsor, CT 06095
0.10
$439,600
3
2
1,846
Off Market
649 Rainbow Road, Windsor, CT 06095
0.11
$491,800
3
2.5
2,430
Off Market
9 Hickory Drive, Windsor, CT 06095
0.11
$387,300
3
2
1,304
Off Market
11 Landing Circle, Windsor, CT 06095
0.13
$483,000
3
2.5
1,978
Off Market
30 Chestnut Drive, Windsor, CT 06095
0.10
$320,800
3
1.5
1,204
Off Market
16 Landing Circle, Windsor, CT 06095
0.15
$500,000
3
2.5
2,237
Recently Sold
34 Chestnut Drive, Windsor, CT 06095
0.12
$384,900
3
2.5
1,784
Off Market
41 Chestnut Drive, Windsor, CT 06095
0.14
$250,000
2
2
1,452
Recently Sold
26 Hickory Drive, Windsor, CT 06095
0.17
$365,000
3
2
1,943
Recently Sold
0 Walnut and Larch Drive, Windsor, CT 06095
0.16
$265,000
-
-
-
For Sale
740 Rainbow Road, Windsor, CT 06095
0.18
$320,000
2
2
1,444
Recently Sold
26 Merriman Road, Windsor, CT 06095
0.23
$513,800
3
2.5
2,782
Off Market

Local Information

  • Map ViewExplore the area around 11 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
1946
Lot Size
0.53 acres
Living Area
1,259 sqft
Price/Sqft
$269

About this House

Three bedroom 2 full bath Cape Cod located in the Rainbow section of Windsor! This home has a spacious kitchen, formal dining room and living room with fireplace. There is a bedroom on the first floor for your easy living convenience. Hardwood floors are through out! This little gem is in need of your personal TLC. Its Sold "As IS", but has many pluses! Detached 2 car garage, New septic tank and D-Box installed 2013, new roof on the home 2012, and a newer 2nd floor bath. A new oil tank has been installed in the basement too. Make an appointment and see what this home has to offer. You will not be disappointed! Conveniently located to Bradley International Airport, Highways and more! Welcome to Windsor! This home is subject to probate approval. possibly a good property for a 203K loan!
11 Chestnut Dr, Windsor, CT 06095 is a 3 bedroom, 2 bathroom, 1,259 sqft single-family home built in 1946. It last sold for $130,000 on Jan 17, 2019. It is currently off market. The Trulia Estimate is $338,500, with a rent estimate of $2,611/month.

Home Details for 11 Chestnut Dr

Interior Features

Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 6
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1946
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.53 acres

Price and Tax history

DateEventPrice
Jan 17, 2019
Source: Smart MLS #170128000
Sold
$130,000
Dec 2, 2018
Source: Agent Provided
Pending
$139,900
Oct 24, 2018
Source: Agent Provided
PriceChange
$139,900
Price decreased by 7%
Sep 30, 2018
Source: Agent Provided
Listed For Sale
$150,000

Market trends in Windsor

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$343K
$7.33KMoM
Sale-to-List Price
102.7%
Price per sq ft
$211
$3MoM
Available listings
44
16MoM

Around this home

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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 11 Chestnut Dr

  • What is 11 Chestnut Dr estimated to be worth?
    Trulia's estimated value for 11 Chestnut Dr in Windsor, CT is $338,500.
  • What is the price history for 11 Chestnut Dr?
    11 Chestnut Dr in Windsor, CT last sold for $130,000 in January 2019.
  • 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 $343K. That is up $7.33K from the prior month.
  • How big is the lot at 11 Chestnut Dr?
    The lot at 11 Chestnut Dr in Windsor, CT is about 0.53 acres (23,087 sq ft).

Explore by feature - Pet Friendly

6 pet-friendly rentals in Windsor, CT

Explore by feature - Washer/dryer

9 rentals with a washer/dryer in Windsor, CT

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 11 Chestnut Dr

Skip to last item
Skip to first item

Homes for sale near 11 Chestnut Dr

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item