34 Chestnut Drive, Windsor, CT 06095
OFF MARKET

34 Chestnut Drive
Windsor, CT 06095

  • 3 Beds
  • 2.5 Baths
  • 1,784 sqft (on 0.52 acres)

$382,900

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $2,724/mo*
Refinance Your Home

$382,900

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $2,724/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,784 sqft
(on 0.52 acres)

Home Value

Trulia Estimate
$383K
Since last month
Increased$3K (+0.9%)
Since last year
Increased$33K (+9.4%)
Since last sale
Increased$64K (+20.1%)
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 +117% in the last 10 years
MonthEstimated value
2026
August 2026$385K
July 2026$382K
June 2026$388K
May 2026$392K
April 2026$379K
March 2026$380K
February 2026$364K
January 2026$363K
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
0.25
Single-Family Home
$500,000
02/27/26
3
2.5
2,237
740 Rainbow Road, Windsor, CT
0.29
Single-Family Home
$320,000
06/15/26
2
2
1,444
351 Rainbow Road, Windsor, CT
0.76
Single-Family Home
$315,000
12/05/25
4
2
2,520
220 Castlewood, Windsor, CT
1.04
Single-Family Home
$370,500
01/07/26
3
1.5
1,484
158 Winterwood, Windsor, CT
1.13
Single-Family Home
$406,000
11/12/25
3
2.5
1,894
19 Rainbow Creek, Windsor, CT
1.13
Single-Family Home
$456,000
02/03/26
3
2.5
1,904
36 High Street, Windsor, CT
1.11
Single-Family Home
$425,000
10/31/25
3
2
1,294
39 Loren Circle, Windsor, CT
1.30
Single-Family Home
$339,000
07/31/26
4
2
2,402

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
41 Chestnut Drive, Windsor, CT 06095
0.05
$250,000
2
2
1,452
Recently Sold
30 Chestnut Drive, Windsor, CT 06095
0.02
$320,800
3
1.5
1,204
Off Market
10 Spruce Road, Windsor, CT 06095
0.11
$324,500
2
1
1,006
Off Market
26 Hickory Drive, Windsor, CT 06095
0.10
$365,000
3
2
1,943
Recently Sold
9 Hickory Drive, Windsor, CT 06095
0.12
$387,300
3
2
1,304
Off Market
0 Walnut and Larch Drive, Windsor, CT 06095
0.22
$265,000
-
-
-
For Sale
649 Rainbow Road, Windsor, CT 06095
0.18
$488,900
3
2.5
2,430
Off Market
710 Rainbow Road, Windsor, CT 06095
0.21
$436,700
3
2
1,846
Off Market
11 Landing Circle, Windsor, CT 06095
0.22
$480,600
3
2.5
1,978
Off Market
100 Wyndemere Lane #100, Windsor, CT 06095
0.24
$424,300
3
3
1,967
Off Market
16 Landing Circle, Windsor, CT 06095
0.25
$500,000
3
2.5
2,237
Recently Sold

Local Information

  • Map ViewExplore the area around 34 Chestnut Drive.
  • 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
1,784 sqft
Price/Sqft
$215
Parking
Open Parking

About this House

HIGHEST AND BEST DEADLINE...MARCH 17TH 8PM....Welcome home! Neighborhood is wonderful and great for walking and when not in your neighborhood enjoy your backyard that has the right amount of shade and privacy...not to0 big and not too small. Enjoy parking in your carport when rain and snow are coming down..Enter your home through your breezeway that is accessible from the back and front yard. Kitchen is off breezeway which makes for bringing in food a breeze. Kitchen is bright with a window box in front of sink that is great for any of your herbs or any plant you desire. Living room is full of even more light with the very large windows and ceiling lights. Additionally on first floor is full bath, bedroom and dining room. Remaining two bedrooms are located on 2nd floor. Both bedrooms have great closets and one is currently being used as playroom. Half bath remodel was just completed. Basement is fully finished with many builtins, hardwood flooring and full bathroom. House has a generator that is fueled by propane tanks. Seller leaves behind all furniture in basement, generator, two propane tanks owned by seller and much more. fence in backyard can be removed easily and seller willing to remove if buyer requests.
34 Chestnut Drive, Windsor, CT 06095 is a 3 bedroom, 3 bathroom, 1,784 sqft single-family home built in 1955. It last sold for $320,500 on May 1, 2024 (11% above the $290,000 asking price). It is currently off market. The Trulia Estimate is $382,900, with a rent estimate of $2,983/month.
Last check for updates: about 5 hours ago
Listed by Nikki Serafino, (413) 427-0387
RE/MAX Connections, (413) 596-8500
Bought with: Isabela Rosario, (860) 736-4027, Premier Properties of CT, (860) 756-0980
Source: Smart MLS, MLS#24003295

Home Details for 34 Chestnut Drive

Interior Features

Interior Details
Basement: Full,FinishedNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom, Dining Room, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1784 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Dryer, Electric Water Heater, Water HeaterDishwasherDisposalDryerLaundry: Lower LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,OilHas CoolingAir Conditioning: Wall Unit(s),Window Unit(s)Has HeatingHeating Fuel: Hot Water
Fireplace & Spa
No Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: Rain GuttersFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 6Parking: None,Paved,Driveway
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 1384 Square FeetFinished Area (below surface): 400 Square Feet

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 770635

Price & Status

Price
List Price: $290,000
Status Change & Dates
Off Market Date: Tue Mar 19 2024Possession Timing: Immediate

Active Status

MLS Status: Closed

Location

Direction & Address
City: Windsor
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Building

Building Area
Building Area: 1784 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.52 acres

Miscellaneous

BasementMls Number: 24003295Attic: NoneAbove Grade Unfinished Area: 1384

Price and Tax history

DateEventPrice
May 1, 2024
Source: Smart MLS #24003295
Sold
$320,500
Apr 8, 2024
Source: Smart MLS #24003295
Pending
$290,000
Mar 16, 2024
Source: Smart MLS #24003295
Listed For Sale
$290,000
Oct 4, 2022
Source: Smart MLS #170503339
Sold
$275,000
Sep 13, 2022
Source: Berkshire Hathaway HomeServices New England Properties #170503339
Contingent
$239,000

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
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  • 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 "
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  • Amy C.
    "Windsor is a town with strong resources and traditions. It has reasonable housing prices and lots of diversity. "
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  • Carol J. M.
    "We have coffee 9am - 11am once a month and other social events. Dog friendly. Neighbors are very friendly."
    0
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  • 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
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  • 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
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  • Lisanickersondouglas
    "Great schools / diverse community. Easy highway access. Lots of parks and trails for walking. Many annual events for kids and families. "
    0
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  • Amani R.
    "We have a yearly block party at each of the local parks. They are usually well attended and snacks are provided. "
    0
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  • 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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LGBTQ Local Legal Protections

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Frequently asked questions about 34 Chestnut Drive

  • What is 34 Chestnut Drive estimated to be worth?
    Trulia's estimated value for 34 Chestnut Drive in Windsor, CT is $382,900.
  • What is the price history for 34 Chestnut Drive?
    34 Chestnut Drive in Windsor, CT last sold for $320,500 in May 2024.
  • 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 34 Chestnut Drive have air conditioning?
    Yes, 34 Chestnut Drive in Windsor, CT has air conditioning.
  • Does 34 Chestnut Drive have laundry facilities?
    Yes, 34 Chestnut Drive in Windsor, CT has in-unit laundry.

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