377 Windsor Ave, Windsor, CT 06095
OFF MARKET

377 Windsor Ave
Windsor, CT 06095

  • 4 Beds
  • 2 Baths
  • 2,618 sqft

$418,000

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $2,967/mo*
Refinance Your Home

$418,000

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $2,967/mo*
Refinance Your Home
4 Beds
2 Baths
2,618 sqft

Home Value

Trulia Estimate
$418K
Since last month
Increased$3K (+0.7%)
Since last year
Increased$7K (+1.6%)
Since last sale
Increased$129K (+44.4%)
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 +127% in the last 10 years
MonthEstimated value
2026
August 2026$419K
July 2026$416K
June 2026$425K
May 2026$423K
April 2026$410K
March 2026$413K
February 2026$396K
January 2026$396K
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
0.33
Multi-Family Home
$285,000
09/22/25
4
2
1,926
43 Barber St, Windsor, CT
0.09
Multi-Family Home
$166,667
09/29/25
3
3
2,434
58-60 Ashford Street, Hartford, CT
1.06
Multi-Family Home
$314,000
04/22/26
4
2
2,614
26-28 Ashford Street, Hartford, CT
1.04
Multi-Family Home
$385,000
02/04/26
4
2
2,772
63-65 Ashford St, Hartford, CT
1.09
Multi-Family Home
$410,000
04/14/26
4
2
3,053
27-29 Addison Street, Hartford, CT
1.16
Multi-Family Home
$285,000
03/31/26
7
3
2,743
322 Deerfield Road, Windsor, CT
0.96
Multi-Family Home
$450,000
11/07/25
5
2
2,709
82 Ashford Street, Hartford, CT
1.08
Multi-Family Home
$380,000
12/30/25
6
3
2,113
30 Harding Avenue, Bloomfield, CT
1.86
Multi-Family Home
$430,000
01/15/26
6
2
2,304
35 Baltic Street, Hartford, CT
1.93
Multi-Family Home
$340,000
03/11/26
4
2
1,664

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
15 Barber Street, Windsor, CT 06095
0.03
$252,400
3
1
1,722
Off Market
24 Barber Street, Windsor, CT 06095
0.06
$287,900
2
1
909
Off Market
38 Faneuil Street, Windsor, CT 06095
0.09
$294,400
2
1
960
Off Market
19 Allen Street, Windsor, CT 06095
0.10
$482,700
5
3
2,512
Off Market
366 Windsor Avenue, Windsor, CT 06095
0.05
$503,300
Studio
4
3,162
Off Market
17 Allen Drive, Broad Brook, CT 06016
0.10
$412,800
3
2.5
2,125
Off Market
111 Benjamin Court #111, Windsor, CT 06095
0.08
$474,800
4
3.5
2,704
Off Market
121 East Barber Street, Windsor, CT 06095
0.10
$260,000
2
1.5
924
Recently Sold
44 Allen Street, Windsor, CT 06095
0.15
$298,800
3
2
1,190
Off Market
25 Corey Street, Windsor, CT 06095
0.13
$378,700
3
1.5
1,146
Off Market
16 Wilson Avenue, Old Saybrook, CT 06475
0.12
$496,100
6
4
3,200
Off Market
32 Skitchewaug Street, Windsor, CT 06095
0.12
$336,400
3
2
1,152
Off Market

Local Information

  • Map ViewExplore the area around 377 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
1926
Living Area
2,618 sqft
Price/Sqft
$160

About this House

Live in one side and rent the other. Home ownership for the cost of rent. Have your tenant pay down the mortgage and build equity!

Looking for investment property? Rent both sides and sit back and let your property pay for itself as it raises in value!

Opportunity to own a hot piece of property in a great location, Wilson area of Windsor. It is in close proximity to all essential amenities. Tenants have 3 minute access to the highway, gas stations, grocery stores in both directions. A quick 9 minute drive brings you to the busy Copaco Shopping Center with fast food restaurants, pharmacies, and banks. Tenants have a 14 minute drive to Bradley International Airport.

One unit is currently leased and current on rent, at $1,200 per month. One unit is vacant, ideal for move in or rental. Empty unit will need cleaning and appliances and it’s already for move in!!

Bad credit is APPROVED! Your credit score does not define YOU! Build your credit while building equity!

Financing Terms:

30 Year Fixed Mortgage

Purchase Price: 229,999
Down Payment: 10% - 12%

Monthly Payments: $2,376

For more information contact me!
377 Windsor Ave, Windsor, CT 06095 is a 4 bedroom, 2 bathroom, 2,618 sqft multi-family built in 1926. It last sold for $290,000 on Feb 14, 2022. It is currently off market. The Trulia Estimate is $418,000, with a rent estimate of $1,924/month.

Home Details for 377 Windsor Ave

Interior Features

Heating & Cooling
Heating: Gas, OilHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Vinyl

Property Information

Year Built
Year Built: 1926
Property Type / Style
Property Type: Multi FamilyArchitecture: Other

Community

Units in Building: 2

Lot Information

Lot Area: 7840 sqft

Price and Tax history

DateEventPrice
Feb 14, 2022
Source: N/A
Sold
$290,000
May 28, 2021
Source: N/A
Sold
$222,000
Jan 16, 2021
Source: N/A
Listed For Sale
$229,000
Aug 19, 2020
Source: Agent Provided
ListingRemoved
$230,000
Aug 4, 2020
Source: Agent Provided
Pending
$230,000

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
    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
    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 377 Windsor Ave

  • What is 377 Windsor Ave estimated to be worth?
    Trulia's estimated value for 377 Windsor Ave is $418,000.
  • What is the price history for 377 Windsor Ave?
    377 Windsor Ave last sold for $290,000 in February 2022.
  • 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.

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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Off Market Homes Near 377 Windsor Ave

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