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

$441,000

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 1,459 sqft (on 1.29 acres)

101 Middlesex Ave, Chester, CT 06412

Chester Center
Est. Refi. Payment $3,061/mo*
Refinance Your Home

Home Value

Trulia Estimate
$441K
Since last month
Decreased$3K (-0.6%)
Since last year
Increased$2K (+0.4%)
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 +67% in the last 10 years
MonthEstimated value
2026
August 2026$441K
August 2026$441K
July 2026$444K
June 2026$454K
May 2026$453K
April 2026$432K
March 2026$431K
February 2026$406K
January 2026$420K
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
131 Middlesex Avenue, Chester, CT
0.27
Single-Family Home
$530,000
02/26/26
3
2.5
1,664
79 Middlesex Avenue, Chester, CT
0.15
Single-Family Home
$410,000
04/30/26
2
1
1,470
14 Ferry Road, Chester, CT
0.57
Single-Family Home
$420,000
09/24/25
4
1.5
2,025
1 Ferry Road, Chester, CT
0.40
Single-Family Home
$635,000
04/30/26
3
3
2,752
16 Hickory Hill Drive, Chester, CT
0.57
Single-Family Home
$755,000
11/19/25
3
2.5
1,896
22 Goose Hill Road, Chester, CT
0.51
Single-Family Home
$500,000
09/02/26
3
2
1,714
1 Ferry Rd, Chester, CT
0.41
Single-Family Home
$635,000
05/01/26
4
3
2,242
7 Hickory Hill Drive, Chester, CT
0.53
Single-Family Home
$549,000
03/24/26
3
2.5
2,202
36 Kings Highway, Chester, CT
0.62
Single-Family Home
$469,900
12/18/25
4
2
1,516
9 Hickory Hill Drive, Chester, CT
0.52
Single-Family Home
$750,000
02/20/26
3
2.5
2,888

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
109A Middlesex Avenue, Chester, CT 06412
0.07
-
-
-
-
Off Market
108 Middlesex Avenue, Chester, CT 06412
0.12
$735,200
4
4.5
4,056
Off Market
96 Middlesex Avenue, Chester, CT 06412
0.10
$1,406,800
4
3.5
3,153
Off Market
79 Middlesex Avenue, Chester, CT 06412
0.15
$410,000
2
1
1,470
Recently Sold
34 Story Hill Road, Chester, CT 06412
0.22
$346,500
2
1
1,081
Off Market
131 Middlesex Avenue, Chester, CT 06412
0.27
$530,000
3
2.5
1,664
Recently Sold
132 Middlesex Avenue, Chester, CT 06412
0.27
$328,700
2
1
1,001
Off Market
7 Old Depot Road, Chester, CT 06412
0.24
$975,000
4
2.5
3,149
Recently Sold
135 Middlesex Avenue, Chester, CT 06412
0.28
$499,000
3
2
1,188
For Sale
41 Railroad Avenue, Chester, CT 06412
0.29
$458,000
2
1
1,771
Off Market
8 School Lane, Chester, CT 06412
0.26
$538,400
3
2
1,512
Off Market
90 Water Street, Chester, CT 06412
0.32
$269,900
1
1
1,034
For Sale

Local Information

  • Map ViewExplore the area around 101 Middlesex Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1949
1.29 acre lot
1,459 sqft
$302/sqft
Garage

About this House

Waterfront on Chester Creek, which has access for putting in kayak or canoe. This lovely home is often admired with a lovely presence on the main road in the quaint CT River Town of Chester. Walk to town and enjoy the eclectic retail and restaurant scene. 2 bedrooms and bath (tub on main floor, 2 bedrooms and bath (stall shower upstairs. lots of Closets, storage and built ins. Hardwood floors. This is a classic cape built to last. Dutch door, Screened porch, workshop in basement, granite front stoop, classic one car garage with workshop. Built by owner for his family and has been in family ever since.
101 Middlesex Ave, Chester, CT 06412 is a 4 bedroom, 2 bathroom, 1,459 sqft single-family home in Chester Center, built in 1949. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $441,000, with a rent estimate of $3,283/month.

Home Details for 101 Middlesex Ave

Interior Features

Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 7
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
FireplaceHot Tub or Spa
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodPatio
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1949Year Updated: 1949
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 1.29 acres

Price and Tax history

DateEventPrice
Mar 7, 2018
Source: Agent Provided
ListingRemoved
$259,000
Feb 14, 2018
Source: Agent Provided
PriceChange
$259,000
Price decreased by 2%
Jan 18, 2018
Source: Agent Provided
PriceChange
$264,000
Price decreased by 2%
Nov 27, 2017
Source: Agent Provided
Listed For Sale
$269,000

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 101 Middlesex Ave

  • What is 101 Middlesex Ave estimated to be worth?
    Trulia's estimated value for 101 Middlesex Ave in Chester, CT is $441,000.
  • 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 101 Middlesex Ave?
    The closest schools to 101 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 101 Middlesex Ave?
    The lot at 101 Middlesex Ave in Chester, CT is about 1.3 acres.
  • Does 101 Middlesex Ave have a garage?
    Yes, 101 Middlesex Ave in Chester, CT has a garage.

Apartments for Rent

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Off Market Homes Near 101 Middlesex Ave

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Homes for sale near 101 Middlesex Ave

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