4 Windward Ave, Middletown, CT 06457
OFF MARKET

4 Windward Ave
Middletown, CT 06457

  • 5 Beds
  • 3 Baths
  • 1,960 sqft

$331,000

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $2,257/mo*
Refinance Your Home

$331,000

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $2,257/mo*
Refinance Your Home
5 Beds
3 Baths
1,960 sqft

Local Information

  • Map ViewExplore the area around 4 Windward Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This multi-family home is located at 4 Windward Ave, Middletown, CT. 4 Windward Ave is in Middletown, CT and in ZIP code 06457. This property has 5 bedrooms, 3 bathrooms and approximately 1,960 sqft of floor space. This property has a lot size of 3484 sqft and was built in 1900.
4 Windward Ave, Middletown, CT 06457 is a 5 bedroom, 3 bathroom, 1,960 sqft multi-family built in 1900. It last sold for $125,000 on Feb 16, 2021. It is currently off market. The Trulia Estimate is $331,000, with a rent estimate of $2,138/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 4 Windward Ave

Interior Features

Interior Details
BasementNumber of Rooms: 10
Heating & Cooling
Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 1900Year Updated: 1980
Property Type / Style
Property Type: Multi Family

Community

Units in Building: 2

Lot Information

Lot Area: 3484 sqft

Price History for 4 Windward Ave

DatePriceEventSource
02/16/2021$125,000Sold
N/A
11/18/2004$132,000Sold
Smart MLS #G359114

Market trends in Middletown

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$282K
$833MoM
Sale-to-List Price
102.3%
1.5%MoM
Price per sq ft
$235
$19MoM
Available listings
84
19MoM
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Property Tax and Assessment

Year2025
Tax$5,529
Assessment$142,140
Home facts updated by county records

Comparable Sales for 4 Windward Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
486 High St, Middletown, CT
0.09
Multi-Family Home
$141,500
10/20/25
5
2
1,800
62 Grand Street, Middletown, CT
0.08
Multi-Family Home
$400,000
10/07/25
4
3
2,016
50 Liberty Street, Middletown, CT
0.10
Multi-Family Home
$335,000
07/14/25
5
2
2,112
207 Pearl Street, Middletown, CT
0.06
Multi-Family Home
$330,000
05/22/26
6
2
1,818
162 Liberty Street, Middletown, CT
0.15
Multi-Family Home
$225,000
06/26/26
4
2
2,186
18 Glover Pl, Middletown, CT
0.13
Multi-Family Home
$249,126
02/27/26
6
2
2,356
31 Erin St, Middletown, CT
0.22
Multi-Family Home
$155,000
08/29/25
4
2
2,070
233 Pearl Street, Middletown, CT
0.11
Multi-Family Home
$295,000
07/17/25
5
2
3,004
410 High Street, Middletown, CT
0.09
Multi-Family Home
$350,000
12/05/25
4
2
1,924
132 Grand Street, Middletown, CT
0.10
Multi-Family Home
$455,000
03/27/26
6
3
3,226

Nearby homes

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Assigned Schools

These are the assigned schools for 4 Windward Ave.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Middletown

At least 386 Trulia users voted on each feature.

  • 84 % Say it's dog friendly

  • 82 % Say car is needed

  • 74 % Say parking is easy

  • 73 % Say there's holiday spirit

  • 71 % Say there are sidewalks

  • 62 % Say yards are well-kept

  • 62 % Say people would walk alone at night

  • 61 % Say streets are well-lit

  • 61 % Say kids play outside

  • 55 % Say it's quiet

  • 52 % Say it's walkable to restaurants

  • 49 % Say there's wildlife

  • 48 % Say neighbors are friendly

  • 42 % Say they plan to stay for at least 5 years

  • 38 % Say it's walkable to grocery stores

  • 23 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Travis Thomas
    "The people are very very nice. I am very comfortable here . Not afraid to leave the front door open or the slider to the deck"
    1
    Flag
  • James.sargeant30
    "My friend lives there she loves it very much good place to live with family everyone works and goes to school"
    0
    Flag
  • Julia Taylor
    "very easy to get to and from work when living in middletown! I work in Cheshire. Just hop onto 691 and in 15 min you’re there. "
    0
    Flag
  • Calm Teacher
    "Good schools for the most part and safe neighborhoods. Students don’t have to wear uniforms. The town has a lot of nice parks. "
    0
    Flag
  • Life Withsymph
    "You get to see the dogs being walked and you can pet them and talk to the owners build bonds , you will be able to see all different types of dogs and mixes "
    0
    Flag
  • Phyloren
    "Watch your children it is not safe. The schools have fights every day. The learning atmosphere is is awful. "
    0
    Flag
  • Kelly Capone
    "I haven’t lived here long and I’m not exactly sure what community events make my neighborhood special. "
    2
    Flag
  • Dlc.marie0816
    "I moved out here in June and I definitely love it.. feels like a nice place for my family, specially my kids"
    0
    Flag
  • Trulia User
    "There are dog parks everywhere, and plenty of places to walk uour dog. Even if you are in an apartment "
    3
    Flag
  • Michael W. W.
    "Wadsworth mansion has many trails. They have several public events in the summer time. There are two other state parks very close that are easily accessible by foot or car. Main Street has many restaurants that offer dine-in, carry out and delivery."
    12
    Flag
  • Joseph V.
    "Middletown is a town that has enjoyable events such as the weekly farmers market the the fall festival and during Christmas time they put up the huge Christmas trees "
    3
    Flag
  • Marquis W. G.
    "My neighborhood is surrounded by semi luxury condos and townhouses full of hard working families. Very family oriented and very peaceful. I love it here!"
    3
    Flag
  • Ishmaila L.
    "Dog owners will like the space made to them to run around and exercise. There are also doggy bags available to help pick up dog waste."
    2
    Flag
  • Marquis W. G.
    "I just moved here recently and I love the community and neighbors. The property is very clean and the neighborhood feels very family oriented "
    0
    Flag
  • Francheska M.
    "Neighbors are very friendly with a really good community sense. Conveniently close to stores and park. "
    0
    Flag
  • Shelby W.
    "The commute downtown on public transportation has changed and not as Easy. Driving downtown is 5-7 minutes. Walking is a half hour. "
    0
    Flag
  • ISA M.
    "School system is awesome in Middletown Ct. You can walk around at night time and still feel safe! I like it that much!"
    0
    Flag
  • Sekernan
    "I drive about 7 or 8 miles to work. Traffic depends on day and time of day. Never too bad. Takes 11-15 minutes to get there. I am able to walk to some stores and laundromats in the area, sidewalks make this safe"
    0
    Flag
  • Richard D.
    "The is a walking/biking trail and a dog park. Nice clean areas safe for walking and locations for waste disposal."
    0
    Flag
  • Christina Y.
    "The schools are awesome for elementary and high school and college.The food here in the restaurants are good too."
    2
    Flag
  • Chelsea C.
    "it’s good but I drive there’s never much traffic which is good and easy to get to work and drive kids to school"
    1
    Flag
  • Michelle E. B.
    "my neighborhood has access to transportation, stores, schools, hospital and is close to downtown. "
    1
    Flag
  • Marisa
    "commute is pretty good, surrounded by plenty of stores and easy access to many restaurants and everything one could need"
    0
    Flag
  • Trevor N.
    "We live near wadsworth mansion so they often have public concerts, vendors, ect. Snow school is right down the road as well. "
    1
    Flag
  • Marisa
    "i think it’s a great place to own a dog .. i have a chocolate lab myself and their are tons of sidewalks and a bike trail as well. everyone’s pretty friendly & clean up after their dogs as well"
    0
    Flag
  • Frankie T.
    "Lots of pups here in Middletown and even some dog-friendly restaurant patios! Our dog loves the walkable North End."
    1
    Flag
  • Molinaronijhana
    "We have bike shows, Christmas carriage rides and a huge tree for Christmas, trick or treating on main st and a wonderful YMCA "
    1
    Flag
  • Shellycato19
    "A lot of dogs living in the area. Not a lot of places to really run, but nice places to take a long and peaceful walk. Unfortunately a lot of owners don’t clean up after their dogs, but it’s starting g to get a little better. Overall a decent place to have pups. "
    1
    Flag
  • Shewarrens
    "It’s a beautiful place to live , It’s a very nice place to grow your kids there’s of restaurant and park and transportation if you don’t drive"
    2
    Flag
  • Asweetrdrm
    "It's a good place to live, low crime rate. Neighbors are friendly. Plenty of kids and close to schools"
    1
    Flag
  • Kurt.r.wentzell
    "There’s not a lot of traffic on my street. A lot of the neighbors have dogs and you always see people walking their dogs on leashes. There’s also a park just down the street."
    1
    Flag
  • Qcockrell
    "more activities for the kids to keep them busy and there need to be more job opportunities for the ones that are looking for a job"
    1
    Flag
  • Lisa C.
    "the neighborhood is a private road with only 1 way in/out. everyone knows everyone. no crime all neighbors have lived here since 1950s and passed houses down through generations. the elementary school is in walking distance safe neighborhood where children could play in the road and not have to worry about traffic"
    2
    Flag
  • Wolver1068.jb
    "We have a great town to raise children in and is rated one of top towns in the United States for raising children. Lots of his Tory in town and the surrounding areas. Great place to have a family vacation!"
    0
    Flag
  • Alnoor R.
    "Decent schools,safe, plenty of kid friendly space. Property taxes are high in CT. Job marked is tepid at best"
    0
    Flag
  • Jagalpure.prafull
    "Nice city and nebourhood. Good parks nearby. very well connected to major highways. Boston and New York are nearest best cities to explore. "
    0
    Flag
  • Brian
    "great central location in CT, close to downtown and highways. quiet neighborhood, but properties very close together"
    0
    Flag
  • Kathy
    "Best restaurant and nightlife scene in the area. outstanding, unique restaurants and small businesses. Plenty of daytime family events on Main street like car shows, bike shows, Christmas tree lighting. Vibrant, diverse community in a college town with a lot of great history that is still celebrated."
    0
    Flag
  • Mhasbro13
    "I’ve lived in this community for 4 years. I love the amenities offered to us. My neighbors are very friendly. Most everyone will say hello when they see you, even if they don’t know you. Great place to liven."
    0
    Flag
  • Leonardo V.
    "It is a very safe place to live..also shopping is close. The neighbors are friendly and very courteous.."
    0
    Flag

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Homes for sale near 4 Windward Ave

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Off Market Homes Near 4 Windward Ave

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