75 Middlesex Ave, Chester, CT 06412
Property image
Property image
OFF MARKET

$521,500

Trulia Estimate
  • 3 Beds
  • 1.5 Baths
  • 1,632 sqft (on 0.66 acres)

75 Middlesex Ave, Chester, CT 06412

Chester Center
Est. Refi. Payment $3,588/mo*
Refinance Your Home
Currently Off Market - Sold Aug 19, 2021 for $360,137

Home Value

Trulia Estimate
$522K
Since last month
Decreased$7K (-1.3%)
Since last year
Increased$21K (+4.2%)
Since last sale
Increased$163K (+45.3%)
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 +93% in the last 10 years
MonthEstimated value
2026
August 2026$523K
August 2026$522K
July 2026$530K
June 2026$545K
May 2026$538K
April 2026$522K
March 2026$518K
February 2026$494K
January 2026$494K
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
79 Middlesex Avenue, Chester, CT
0.04
Single-Family Home
$410,000
04/30/26
2
1
1,470
131 Middlesex Avenue, Chester, CT
0.45
Single-Family Home
$530,000
02/26/26
3
2.5
1,664
21 East Liberty Street, Chester, CT
0.35
Single-Family Home
$252,500
11/17/25
2
1
1,012
72 Winter Avenue, Deep River, CT
0.57
Single-Family Home
$320,000
08/26/26
3
3
1,836
35 Maple Street, Chester, CT
0.45
Single-Family Home
$780,000
01/15/26
3
2
1,772
54 Maple St, Chester, CT
0.64
Single-Family Home
$325,000
11/26/25
3
2
1,260
7 Hickory Hill Drive, Chester, CT
0.36
Single-Family Home
$549,000
03/24/26
3
2.5
2,202
23 Hickory Hill Dr, Chester, CT
0.44
Single-Family Home
$446,000
10/23/25
3
3
1,876
16 Hickory Hill Drive, Chester, CT
0.39
Single-Family Home
$755,000
11/19/25
3
2.5
1,896
15 Kirtland Terrace, Chester, CT
0.59
Single-Family Home
$187,000
09/04/25
3
1.5
1,170

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
79 Middlesex Avenue, Chester, CT 06412
0.04
$410,000
2
1
1,470
Recently Sold
8 School Lane, Chester, CT 06412
0.10
$538,400
3
2
1,512
Off Market
7 Old Depot Road, Chester, CT 06412
0.12
$975,000
4
2.5
3,149
Recently Sold
9 School Lane, Chester, CT 06412
0.14
$519,800
3
1.5
1,388
Off Market
137 Main Street, Chester, CT 06412
0.14
$656,200
3
1.5
1,570
Off Market
142 Main Street, Chester, CT 06412
0.17
$729,000
3
2
2,188
Off Market
96 Middlesex Avenue, Chester, CT 06412
0.18
$1,406,800
4
3.5
3,153
Off Market
109A Middlesex Avenue, Chester, CT 06412
0.24
-
-
-
-
Off Market
97 Main Street, Chester, CT 06412
0.25
$644,100
4
1.5
1,544
Off Market
108 Middlesex Avenue, Chester, CT 06412
0.27
$735,200
4
4.5
4,056
Off Market
83 Main Street, Essex, CT 06426
0.28
$723,200
6
2
3,000
Off Market
24 East Liberty Street, Chester, CT 06412
0.30
$489,600
4
2
1,926
Off Market

Local Information

  • Map ViewExplore the area around 75 Middlesex Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2001
Lot Size
0.66 acres
Living Area
1,632 sqft
Price/Sqft
$320

About this House

Take a short walk to Chester Village from this handsomely kept 3-4 bedroom home. The large eat-in Granite Kitchen boasts a large center island and stainless steel appliances. From the kitchen youll step out onto the deck and 12' x 40' stone patio overlooking the backyard. Enjoy beautiful sunsets throughout the year from the deck and patio. The flexible floor plan with a room off the kitchen allows for a Dining Room, first floor Bedroom or Office. Cozy Living Room with fireplace that uses gas or wood. The second floor has a Master Bedroom with walk-in closet and access to a common bathroom. 2 additional Bedrooms are situated beside the second floor laundry. The full basement is ready for your finishing if you need a little more room. Central air conditioning. Central vac. 12' x 20' outbuilding with electricity. Multiple parking spots. The spacious lawn leads you to the rear of North Quarter Park and its newly created Disc Golf course. Its an easy, safe walk to the playground and on to downtown Chester, a family friendly town where all are welcome. Browse the art galleries, quaint shops and dine on tasty food.
75 Middlesex Ave, Chester, CT 06412 is a 3 bedroom, 2 bathroom, 1,632 sqft single-family home in Chester Center, built in 2001. It last sold for $360,137 on Aug 19, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $521,500, with a rent estimate of $3,346/month.

Home Details for 75 Middlesex Ave

Interior Features

Interior Details
BasementNumber of Rooms: 6Types of Rooms: Walk In Closet, Dining Room
Heating & Cooling
Heating: Forced AirAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Other
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: OtherPatio

Property Information

Year Built
Year Built: 2001Year Updated: 2013
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 0.66 acres

Price and Tax history

DateEventPrice
Aug 19, 2021
Source: Smart MLS #170396365
Sold
$360,137
May 21, 2021
Source: RE/MAX International #170396365
Pending
$349,900
May 21, 2021
Source: RE/MAX International
ListingRemoved
May 20, 2021
Source: RE/MAX International #170396365
Pending
$349,900
May 14, 2021
Source: RE/MAX International #170396365
Listed For Sale
$349,900

Market trends in Chester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
12
4MoM

Around this home

Neighborhood Overview

Chester Center
See Local Highlights
Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

Frequently asked questions about 75 Middlesex Ave

  • What is 75 Middlesex Ave estimated to be worth?
    Trulia's estimated value for 75 Middlesex Ave in Chester, CT is $521,500.
  • What is the price history for 75 Middlesex Ave?
    75 Middlesex Ave in Chester, CT last sold for $360,137 in August 2021.
  • Is Chester a buyer's or seller's market?
    Chester is currently a seller's market, based on recent for-sale activity.
  • What are the closest schools to 75 Middlesex Ave?
    The closest schools to 75 Middlesex Ave in Chester, CT are Chester Elementary School (Pre-K, rated 7/10), John Winthrop Middle School (rated 4/10), Valley Regional High School (rated 7/10).
  • How big is the lot at 75 Middlesex Ave?
    The lot at 75 Middlesex Ave in Chester, CT is about 0.66 acres (28,750 sq ft).

Apartments for Rent

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