41 Chestnut Drive, Windsor, CT 06095
SOLD
FEB 13, 2026

41 Chestnut Drive
Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,452 sqft (on 0.55 acres)

$250,000

Last Sold: Feb 13, 2026
9% below list $275K
$172/sqft
Est. Refi. Payment $1,805/mo*
Refinance Your Home

$250,000

Last Sold: Feb 13, 2026
9% below list $275K
$172/sqft
Est. Refi. Payment $1,805/mo*
Refinance Your Home
2 Beds
2 Baths
1,452 sqft
(on 0.55 acres)

Home Value

Trulia Estimate
$263K
Since last month
$100 (0%)
Since last year
Decreased$124K (-32.1%)
Since last sale
Increased$13K (+5.1%)
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 +46% in the last 10 years
MonthEstimated value
2026
August 2026$263K
July 2026$263K
June 2026$264K
May 2026$261K
April 2026$260K
March 2026$252K
February 2026$251K
January 2026$271K
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
26 Hickory Drive, Windsor, CT
0.14
Single-Family Home
$365,000
01/29/26
3
2
1,943
740 Rainbow Road, Windsor, CT
0.30
Single-Family Home
$320,000
06/15/26
2
2
1,444
16 Landing Circle, Windsor, CT
0.29
Single-Family Home
$500,000
02/27/26
3
2.5
2,237
351 Rainbow Road, Windsor, CT
0.80
Single-Family Home
$315,000
12/05/25
4
2
2,520
220 Castlewood, Windsor, CT
1.07
Single-Family Home
$370,500
01/07/26
3
1.5
1,484
36 High Street, Windsor, CT
1.14
Single-Family Home
$425,000
10/31/25
3
2
1,294
1 Walter's Way, Windsor, CT
0.39
Single-Family Home
$553,000
08/19/26
4
3.5
3,552
158 Winterwood, Windsor, CT
1.15
Single-Family Home
$406,000
11/12/25
3
2.5
1,894
39 Loren Circle, Windsor, CT
1.31
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
34 Chestnut Drive, Windsor, CT 06095
0.05
$384,900
3
2.5
1,784
Off Market
30 Chestnut Drive, Windsor, CT 06095
0.06
$320,800
3
1.5
1,204
Off Market
10 Spruce Road, Windsor, CT 06095
0.10
$326,600
2
1
1,006
Off Market
26 Hickory Drive, Windsor, CT 06095
0.14
$365,000
3
2
1,943
Recently Sold
9 Hickory Drive, Windsor, CT 06095
0.17
$387,300
3
2
1,304
Off Market
0 Walnut and Larch Drive, Windsor, CT 06095
0.20
$265,000
-
-
-
For Sale
649 Rainbow Road, Windsor, CT 06095
0.22
$491,800
3
2.5
2,430
Off Market
710 Rainbow Road, Windsor, CT 06095
0.23
$439,600
3
2
1,846
Off Market
11 Landing Circle, Windsor, CT 06095
0.26
$483,000
3
2.5
1,978
Off Market
100 Wyndemere Lane #100, Windsor, CT 06095
0.28
$426,800
3
3
1,967
Off Market
16 Landing Circle, Windsor, CT 06095
0.29
$500,000
3
2.5
2,237
Recently Sold

Local Information

  • Map ViewExplore the area around 41 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
0.55 acres
Living Area
1,452 sqft
Price/Sqft
$172/sqft
Parking
2 Car Garage

About this House

Welcome to 41 Chestnut Drive, a charming and well-maintained Cape Cod style home nestled in a quiet Windsor neighborhood, perfect for those seeking comfort, convenience, and classic New England character. This bright and inviting residence has 2 spacious bedrooms with an extra room for either a den or an office, 2 full baths with one being totally renovated, with a flexible floor plan that blends functionality and warmth. A spacious kitchen with ample cabinetry flows easily into the dining area, making meal preparation and gatherings seamless. Hardwood floors add timeless appeal, while thoughtful updates ensure modern comfort. Upstairs bedrooms provide privacy and flexibility for family, guests, or a home office. The home sits on a generous, level 0.55-acre lot with a beautifully landscaped yard-ideal for outdoor activities, gardening, or relaxing on warm afternoons. A private driveway and garage offer plenty of parking and storage. Located just minutes from Windsor Center, schools, shopping, dining, and major highways, this property combines suburban tranquility with easy access to Hartford, Bradley International Airport, and all that the Connecticut River Valley has to offer. Whether you are a first-time owner, downsizing, or simply seeking a welcoming place , 41 Chestnut Drive is a wonderful opportunity to make your next move in Windsor.
41 Chestnut Drive, Windsor, CT 06095 is a 2 bedroom, 2 bathroom, 1,452 sqft single-family home built in 1955. It last sold for $250,000 on Feb 13, 2026 (9% below the $274,925 asking price). It is currently off market. The Trulia Estimate is $262,900, with a rent estimate of $2,412/month.
Last check for updates: about 2 hours ago
Listed by Jayson G. Kemp, (860) 573-0277
Five Stars Realty, (860) 560-1500
Maria Pirulli, (860) 306-0010
Five Stars Realty, (860) 560-1500
Bought with: Elvis Methoxha, (860) 302-8187, Country Manor Realty, (860) 589-2100
Source: Smart MLS, MLS#24142259

Home Details for 41 Chestnut Drive

Interior Features

Interior Details
Basement: Full,Partially FinishedNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom, Dining Room, Living Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1452 Square Feet
Appliances & Utilities
Appliances: Electric Range, Refrigerator, Dishwasher, Washer, Dryer, Electric Water Heater, Water HeaterDishwasherDryerLaundry: Lower Level,Mud RoomRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace

Exterior Features

Exterior Home Features
Roof: Asphalt GableFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Attached,Paved,Driveway,Private
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 1452 Square Feet

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: BrickNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 770616

Price & Status

Price
List Price: $274,925Price Per Sqft: $172/sqft
Status Change & Dates
Off Market Date: Sun Jan 04 2026Possession Timing: Negotiable

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: 1452 Square Feet

Community

Community Features: Shopping/Mall, Near Public Transport

HOA

No HOA

Lot Information

Lot Area: 0.55 acres

Miscellaneous

BasementMls Number: 24142259Attic: Pull Down StairsAttribution Contact: (860) 573-0277Above Grade Unfinished Area: 1452

Additional Information

Shopping/MallNear Public Transport

Price and Tax history

DateEventPrice
Feb 13, 2026
Source: Smart MLS #24142259
Sold
$250,000
Jan 4, 2026
Source: Smart MLS #24142259
Pending
$274,925
Dec 30, 2025
Source: Smart MLS #24142259
PriceChange
$274,925
Price decreased by 8%
Dec 23, 2025
Source: Smart MLS #24142259
Pending
$299,925
Dec 15, 2025
Source: Smart MLS #24142259
PriceChange
$299,925
Price decreased by 5%

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
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  • 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
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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
    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
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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
    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

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 41 Chestnut Drive

  • What is 41 Chestnut Drive estimated to be worth?
    Trulia's estimated value for 41 Chestnut Drive in Windsor, CT is $262,900.
  • What is the price history for 41 Chestnut Drive?
    41 Chestnut Drive in Windsor, CT last sold for $250,000 in February 2026.
  • 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 41 Chestnut Drive have air conditioning?
    Yes, 41 Chestnut Drive in Windsor, CT has air conditioning.
  • Does 41 Chestnut Drive have laundry facilities?
    Yes, 41 Chestnut Drive in Windsor, CT has in-unit laundry.

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