237 Dudley Town Rd, Windsor, CT 06095
Property image
Property image
OFF MARKET

$442,800

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,094 sqft (on 0.70 acres)

237 Dudley Town Rd, Windsor, CT 06095

Est. Refi. Payment $3,153/mo*
Refinance Your Home

Home Value

Trulia Estimate
$443K
Since last month
Decreased$2K (-0.3%)
Since last year
Increased$4K (+0.8%)
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 +98% in the last 10 years
MonthEstimated value
2026
August 2026$442K
July 2026$443K
June 2026$451K
May 2026$455K
April 2026$443K
March 2026$438K
February 2026$419K
January 2026$424K
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
21 Long Hill Road, Windsor, CT
0.11
Single-Family Home
$440,000
11/21/25
3
2.5
2,264
45 Long Hill Road, Windsor, CT
0.17
Single-Family Home
$425,000
09/08/25
4
2.5
2,040
97 Brookview Road, Windsor, CT
0.44
Single-Family Home
$425,000
05/29/26
3
3
1,990
123 Dudley Town Rd, Windsor, CT
0.23
Single-Family Home
$180,000
05/26/26
4
2
1,630
170 Dudley Town Road, Windsor, CT
0.14
Single-Family Home
$382,000
10/30/25
4
2
1,645
29 Quail Hollow Drive, Windsor, CT
0.47
Single-Family Home
$445,900
01/09/26
3
2
1,850
1111 Matianuck Avenue, Windsor, CT
0.42
Single-Family Home
$280,000
09/16/25
3
1.5
1,142
708 Park Avenue, Windsor, CT
0.54
Single-Family Home
$410,000
06/30/26
3
2
1,736
41 Hale Drive, Windsor, CT
0.61
Single-Family Home
$368,500
12/15/25
3
1.5
1,558
72 Brookview Road, Windsor, CT
0.53
Single-Family Home
$435,000
10/10/25
4
3
2,660

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
278 Dudley Town Road, Windsor, CT 06095
0.12
$422,500
3
1.5
2,623
Off Market
21 Long Hill Road, Windsor, CT 06095
0.11
$440,000
3
2.5
2,264
Recently Sold
45 Long Hill Road, Windsor, CT 06095
0.17
$445,400
4
2.5
2,040
Off Market
170 Dudley Town Road, Windsor, CT 06095
0.14
$397,700
4
2
1,645
Off Market
32 Andrew Lane, Windsor, CT 06095
0.21
$424,200
3
2.5
1,293
Off Market
20 Whitney Circle, Windsor, CT 06095
0.16
$462,400
3
2.5
2,492
Off Market
139 Dudley Town Road, Windsor, CT 06095
0.21
$377,900
4
1.5
1,434
Off Market
27 Devin Way, Windsor, CT 06095
0.22
$549,600
4
3
1,772
Off Market
93 Long Hill Road, Windsor, CT 06095
0.33
$464,600
3
3
1,999
Off Market
106 Long Hill Road, Windsor, CT 06095
0.38
$490,100
4
2.5
1,840
Off Market
22 Jubrey Drive, Windsor, CT 06095
0.39
$766,000
4
4.5
5,108
Recently Sold
35 Jubrey Drive, Windsor, CT 06095
0.42
$714,000
4
3.5
3,191
Off Market

Local Information

  • Map ViewExplore the area around 237 Dudley Town Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1986
Lot Size
0.7 acres
Living Area
2,094 sqft
Price/Sqft
$211
Parking
Garage

About this House

New Competitive PriceWell Built Raised Ranch is situated on a beautifully gardened and private lot Spacious Kitchen overlooking backyard as well Formal dining room with sliders to deck is perfect for a picnic and entertaining. Master Bedroom offers full bath also with a view of private yard. Lower level 24x21 family room is very spacious with a brick fireplace and walk-out...half bath and laundry room. This could be an ideal in-law and/or is ideal for entertaining. Enjoy a cool drink on the backyard 14' Screened Pavilion10' surrounded by gardens and privacy Enjoy the central air during the hot summer days and the cozy fireplace on cold winter's eve. Amenities include generator hook-up, alarm system and central air conditioning. Front and side yard has an inground sprinkler system. Newer "Boardwalk" Deck. New gutters and roof in 2012. Vinyl-clad overhead garage doors with garage door openers. Though close to shopping and highway access this home makes you feel like you are enjoying a piece of the country life
237 Dudley Town Rd, Windsor, CT 06095 is a 3 bedroom, 3 bathroom, 2,094 sqft single-family home built in 1986. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $442,800, with a rent estimate of $2,973/month.

Home Details for 237 Dudley Town Rd

Interior Features

Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
AtticNumber of Rooms: 6
Appliances & Utilities
DishwasherDisposalRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1986Year Updated: 1986
Property Type / Style
Property Type: Single Family HomeArchitecture: ranch

Community

Units in Building: 1

Lot Information

Lot Area: 0.70 acres

Price and Tax history

DateEventPrice
Oct 22, 2018
Source: Agent Provided
ListingRemoved
$249,900
Sep 12, 2018
Source: Agent Provided
PriceChange
$249,900
Price decreased by 1%
Aug 21, 2018
Source: Agent Provided
PriceChange
$252,900
Price decreased by 3%
Jul 21, 2018
Source: Agent Provided
Listed For Sale
$259,900

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 237 Dudley Town Rd

  • What is 237 Dudley Town Rd estimated to be worth?
    Trulia's estimated value for 237 Dudley Town Rd in Windsor, CT is $442,800.
  • 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.
  • What do residents say about Windsor?
    Residents describe Windsor, CT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Windsor, CT.
  • Does 237 Dudley Town Rd have air conditioning?
    Yes, 237 Dudley Town Rd in Windsor, CT has air conditioning.
  • How big is the lot at 237 Dudley Town Rd?
    The lot at 237 Dudley Town Rd in Windsor, CT is about 0.70 acres (30,492 sq ft).

Explore by feature - Pet Friendly

6 pet-friendly rentals in Windsor, CT

Explore by feature - Air Conditioning

6 rentals with air conditioning 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 237 Dudley Town Rd

Skip to last item
Skip to first item

Homes for sale near 237 Dudley Town Rd

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