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

29 Chestnut Dr
Windsor, CT 06095

  • 3 Beds
  • 1 Bath
  • 1,144 sqft

$278,700

Trulia Estimate
as of Aug 20, 2026

$278,700

Trulia Estimate
as of Aug 20, 2026
  • 3 Beds
  • 1 Bath
  • 1,144 sqft

Home Highlights

Property Type
Single-Family Home
Living Area
1,144 sqft
Price/Sqft
$244

Local Information

  • Map ViewExplore the area around 29 Chestnut Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Private room with two windows and a closet, shared bathroom and kitchen. Located on a quiet neighborhood, less than minutes from the airport. Shared driveway for one car.

1 year lease, no smoking inside
29 Chestnut Dr, Windsor, CT 06095 is a 3 bedroom, 1 bathroom, 1,144 sqft single-family home. It last sold for $100,000 on Nov 14, 1996 (11,011% above the $900 asking price). It is currently off market. The Trulia Estimate is $278,700, with a rent estimate of $2,502/month.

Home Details for 29 Chestnut Dr

Interior Features

Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: Central AirHeating Fuel: Baseboard
Appliances & Utilities
MicrowaveRefrigerator
Levels, Entrance, & Accessibility
Floors: Hardwood, Tile
Room & Shared Space
Room is not furnished

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: nowUtilities Share: 1/3 monthly utility

Comparable Sales for 29 Chestnut Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
41 Chestnut Drive, Windsor, CT
0.06
Single-Family Home
$250,000
02/13/26
2
2
1,452 sqft
26 Hickory Drive, Windsor, CT
0.14
Single-Family Home
$365,000
01/29/26
3
2
1,943 sqft
740 Rainbow Road, Windsor, CT
0.25
Single-Family Home
$320,000
06/15/26
2
2
1,444 sqft
16 Landing Circle, Windsor, CT
0.23
Single-Family Home
$500,000
02/27/26
3
2.5
2,237 sqft
552 Stone Road, Windsor, CT
1.15
Single-Family Home
$300,000
01/16/26
3
1
1,128 sqft
1 Walter's Way, Windsor, CT
0.34
Single-Family Home
$553,000
08/19/26
4
3.5
3,552 sqft
351 Rainbow Road, Windsor, CT
0.80
Single-Family Home
$315,000
12/05/25
4
2
2,520 sqft
220 Castlewood, Windsor, CT
1.01
Single-Family Home
$370,500
01/07/26
3
1.5
1,484 sqft
36 High Street, Windsor, CT
1.15
Single-Family Home
$425,000
10/31/25
3
2
1,294 sqft
158 Winterwood, Windsor, CT
1.10
Single-Family Home
$406,000
11/12/25
3
2.5
1,894 sqft

Nearby homes

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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

Price and Tax history

DateEventPrice
Nov 14, 1996
Source: N/A
Sold
$100,000

Frequently asked questions about 29 Chestnut Dr

  • What is 29 Chestnut Dr estimated to be worth?
    Trulia's estimated value for 29 Chestnut Dr in Windsor, CT is $278,700.
  • What is the price history for 29 Chestnut Dr?
    29 Chestnut Dr in Windsor, CT last sold for $100,000 in November 1996.
  • 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.
  • Does 29 Chestnut Dr have air conditioning?
    Yes, 29 Chestnut Dr in Windsor, CT has air conditioning.

Homes for rent near 29 Chestnut Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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