253 Windsor Ave, Windsor, CT 06095
OFF MARKET

253 Windsor Ave
Windsor, CT 06095

  • Studio
  • 2,295 sqft

$456,300

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $3,232/mo*
Refinance Your Home

$456,300

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $3,232/mo*
Refinance Your Home
Studio
2,295 sqft

Home Value

Trulia Estimate
$456K
Since last month
Increased$10K (+2.2%)
Since last year
Increased$17K (+3.8%)
Since last sale
Increased$216K (+90.9%)
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 +135% in the last 10 years
MonthEstimated value
2026
August 2026$455K
July 2026$445K
June 2026$457K
May 2026$447K
April 2026$430K
March 2026$430K
February 2026$418K
January 2026$426K
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
33 Wilson Avenue, Windsor, CT
0.10
Multi-Family Home
$285,000
09/22/25
4
2
1,926
43 Barber St, Windsor, CT
0.30
Multi-Family Home
$166,667
09/29/25
3
3
2,434
58-60 Ashford Street, Hartford, CT
0.77
Multi-Family Home
$314,000
04/22/26
4
2
2,614
26-28 Ashford Street, Hartford, CT
0.75
Multi-Family Home
$385,000
02/04/26
4
2
2,772
27-29 Addison Street, Hartford, CT
0.87
Multi-Family Home
$285,000
03/31/26
7
3
2,743
82 Ashford Street, Hartford, CT
0.79
Multi-Family Home
$380,000
12/30/25
6
3
2,113
63-65 Ashford St, Hartford, CT
0.80
Multi-Family Home
$410,000
04/14/26
4
2
3,053
322 Deerfield Road, Windsor, CT
1.25
Multi-Family Home
$450,000
11/07/25
5
2
2,709
218 Martin Street, Hartford, CT
1.62
Multi-Family Home
$328,000
03/13/26
6
2
2,111
2657 Main Street, Hartford, CT
1.48
Multi-Family Home
$500,000
01/09/26
9
3
3,348

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
28 Becker Circle, Windsor, CT 06095
0.09
$331,400
3
1
1,229
Off Market
21 Charlevoix Place, Windsor, CT 06095
0.09
-
-
-
-
Off Market
296 Windsor Avenue, Windsor, CT 06095
0.12
$550,100
9
3
3,060
Off Market
33 Wilson Avenue, Windsor, CT 06095
0.10
$301,900
4
2
1,926
Off Market
145 Becker Circle, Windsor, CT 06095
0.13
$340,300
3
1.5
1,358
Off Market
53 Bina Avenue, Windsor, CT 06095
0.12
$342,400
3
1
1,156
Off Market
69 Becker Circle, Windsor, CT 06095
0.15
$383,600
4
2
1,373
Off Market
47 Wilson Avenue, Windsor, CT 06095
0.13
$315,000
3
2
1,415
Recently Sold
48 Olga Avenue, Windsor, CT 06095
0.12
$390,800
4
3
1,936
Off Market
25 Corey Street, Windsor, CT 06095
0.18
$378,700
3
1.5
1,146
Off Market
70 Becker Circle, Windsor, CT 06095
0.18
$365,000
3
2
1,229
Off Market
16 Wilson Avenue, Old Saybrook, CT 06475
0.19
$496,100
6
4
3,200
Off Market

Local Information

  • Map ViewExplore the area around 253 Windsor Ave.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1840
Living Area
2,295 sqft
Price/Sqft
$199

About this House

A SHOWING IS A SALE! Don't miss out on this rare find! This meticulously maintained and recently renovated 2-family house is one in a million! Let your tenants pay the mortgage when you rent one unit and occupy the other! The first floor 2-bedroom apartment has been completed renovated and includes a gorgeous kitchen with granite countertops and stainless steel appliances, hardwood floors throughout, high ceilings, large windows with lots of natural light, remodeled bathroom with a glass enclosed bathtub and updated fixtures, ample storage space, a deck, and an attached garage!! The apartment also has an over-sized mudroom and an office. The second floor has 2 huge bedrooms with lots of closet space, a gorgeous remodeled bathroom with updated fixtures, huge living room and kitchen, large windows, and a finished attic to allow for additional living space.
253 Windsor Ave, Windsor, CT 06095 is a studio, 2,295 sqft multi-family built in 1840. It last sold for $238,140 on Sep 22, 2006. More recently, it was listed as a rental in February 2012 with an asking price of $1,200 per month. That rental listing was removed on April 14, 2012. It is currently off market. The Trulia Estimate is $456,300, with a rent estimate of $1,888/month.

Home Details for 253 Windsor Ave

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
Parking Spaces: 5

Property Information

Year Built
Year Built: 1840
Property Type / Style
Property Type: Multi FamilyArchitecture: Other

Community

Units in Building: 2

Lot Information

Lot Area: 8276 sqft

Price and Tax history

DateEventPrice
Aug 2, 2017
Source: Agent Provided
ListingRemoved
$269,899
Jun 8, 2017
Source: Agent Provided
Pending
$269,899
Jun 2, 2017
Source: Agent Provided
Listed For Sale
$269,899
Apr 14, 2012
Source: Agent Provided
ListingRemoved
$1,200
Feb 4, 2012
Source: Agent Provided
Listed For Rent
$1,200

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 253 Windsor Ave

  • What is 253 Windsor Ave estimated to be worth?
    Trulia's estimated value for 253 Windsor Ave is $456,300.
  • What is the price history for 253 Windsor Ave?
    253 Windsor Ave last sold for $238,140 in September 2006.
  • 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 253 Windsor Ave have parking?
    Yes, 253 Windsor Ave has on-site parking.

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

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