296 Windsor Avenue, Windsor, CT 06095
OFF MARKET

296 Windsor Avenue
Windsor, CT 06095

  • 9 Beds
  • 3 Baths
  • 3,060 sqft

$550,100

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $3,876/mo*
Refinance Your Home

$550,100

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $3,876/mo*
Refinance Your Home
9 Beds
3 Baths
3,060 sqft

Home Value

Trulia Estimate
$550K
Since last month
Increased$16K (+2.9%)
Since last year
Increased$16K (+3%)
Since last sale
Increased$103K (+22.9%)
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 +263% in the last 10 years
MonthEstimated value
2026
August 2026$553K
July 2026$538K
June 2026$554K
May 2026$548K
April 2026$530K
March 2026$539K
February 2026$524K
January 2026$528K
2025
2024
2023
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
0.15
Multi-Family Home
$285,000
09/22/25
4
2
1,926
26-28 Ashford Street, Hartford, CT
0.86
Multi-Family Home
$385,000
02/04/26
4
2
2,772
82 Ashford Street, Hartford, CT
0.91
Multi-Family Home
$380,000
12/30/25
6
3
2,113
27-29 Addison Street, Hartford, CT
0.98
Multi-Family Home
$285,000
03/31/26
7
3
2,743
58-60 Ashford Street, Hartford, CT
0.88
Multi-Family Home
$314,000
04/22/26
4
2
2,614
2657 Main Street, Hartford, CT
1.59
Multi-Family Home
$500,000
01/09/26
9
3
3,348
283 Martin Street, Hartford, CT
1.63
Multi-Family Home
$535,000
06/03/26
9
3
3,750
322 Deerfield Road, Windsor, CT
1.14
Multi-Family Home
$450,000
11/07/25
5
2
2,709

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
16 Wilson Avenue, Old Saybrook, CT 06475
0.07
$496,100
6
4
3,200
Off Market
28 Becker Circle, Windsor, CT 06095
0.09
$331,400
3
1
1,229
Off Market
25 Corey Street, Windsor, CT 06095
0.10
$378,700
3
1.5
1,146
Off Market
21 Charlevoix Place, Windsor, CT 06095
0.11
-
-
-
-
Off Market
111 Benjamin Court #111, Windsor, CT 06095
0.11
$474,800
4
3.5
2,704
Off Market
33 Wilson Avenue, Windsor, CT 06095
0.15
$301,900
4
2
1,926
Off Market
69 Becker Circle, Windsor, CT 06095
0.15
$383,600
4
2
1,373
Off Market
47 Wilson Avenue, Windsor, CT 06095
0.15
$315,000
3
2
1,415
Recently Sold
70 Becker Circle, Windsor, CT 06095
0.17
$365,000
3
2
1,229
Off Market
145 Becker Circle, Windsor, CT 06095
0.17
$340,300
3
1.5
1,358
Off Market
366 Windsor Avenue, Windsor, CT 06095
0.16
$503,300
Studio
4
3,162
Off Market

Local Information

  • Map ViewExplore the area around 296 Windsor Avenue.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1890
Living Area
3,060 sqft
Price/Sqft
$180
Parking
Garage

About this House

Rarely available fully occupied 3 family! All 3 gas heating systems are 10 years old. Roof is about 15 years old. Washer and dryer hook ups located in basement, which new owner can add coin operated washer and dryer for additional income. Three separate hot water tanks for all 3 units. All tenants are currently month-to-month with below market rents. Tenant paid utilities. Owner pays for water. Plenty of off-street parking available. Open-House: All 3 units will be accessible this Sunday July 21st from 12-4P.M. Don't miss this opportunity!
296 Windsor Avenue, Windsor, CT 06095 is a 9 bedroom, 3 bathroom, 3,060 sqft multi-family built in 1890. It last sold for the $450,000 asking price on Sep 6, 2024. More recently, it was listed as a rental in July 2020 with an asking price of $1,150 per month. That rental listing was removed on August 4, 2020. It is currently off market. The Trulia Estimate is $550,100, with a rent estimate of $1,777/month.
Last check for updates: about 5 hours ago
Listed by Greg Grochowski, (860) 371-4738
SalCal Real Estate Connections, (860) 893-0093
Bought with: Chrissy Baskerville, (860) 883-8907, The Property Shop CT, (860) 519-0634
Source: Smart MLS, MLS#24032579

Home Details for 296 Windsor Avenue

Interior Features

Interior Details
Basement: FullNumber of Rooms: 12
Beds & Baths
Number of Bedrooms: 9Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 3060 Square Feet
Appliances & Utilities
Appliances: Water HeaterLaundry: In Basement
Heating & Cooling
Heating: Forced Air,Steam,Natural GasNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
No Fireplace
View
Has a ViewView: City

Exterior Features

Exterior Home Features
Roof: OtherFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageNo Attached GarageParking Spaces: 6Parking: Detached,Paved
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3060 Square Feet

Property Information

Year Built
Year Built: 1890
Property Type / Style
Property Type: Residential IncomeProperty Subtype: Multi FamilyArchitecture: Units on different Floors
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 781659

Price & Status

Price
List Price: $450,000
Status Change & Dates
Off Market Date: Fri Jul 26 2024Possession Timing: Occupancy

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 3060 Square Feet

HOA

No HOA

Lot Information

Lot Area: 6534 sqft

Miscellaneous

BasementMls Number: 24032579Attic: NoneAbove Grade Unfinished Area: 3060

Price and Tax history

DateEventPrice
Sep 6, 2024
Source: Smart MLS #24032579
Sold
$450,000
Jul 28, 2024
Source: Smart MLS #24032579
Pending
$450,000
Jul 21, 2024
Source: Smart MLS #24032579
Listed For Sale
$450,000
Aug 4, 2020
Source: Agent Provided
ListingRemoved
$1,150
Jul 14, 2020
Source: Agent Provided
Listed For Rent
$1,150

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
    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

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 296 Windsor Avenue

  • What is 296 Windsor Avenue estimated to be worth?
    Trulia's estimated value for 296 Windsor Avenue is $550,100.
  • What is the price history for 296 Windsor Avenue?
    296 Windsor Avenue last sold for $450,000 in September 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 296 Windsor Avenue have laundry facilities?
    Yes, 296 Windsor Avenue has laundry facilities.

Explore by feature - Pet Friendly

6 pet-friendly rentals in Windsor, CT

Explore by feature - Washer/dryer

8 rentals with a washer/dryer in Windsor, CT

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