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

$271,200

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 792 sqft (on 0.26 acres)

65 Middlesex Ave, Chester, CT 06412

Chester Center
Est. Refi. Payment $1,959/mo*
Refinance Your Home
Currently Off Market - Sold Apr 26, 2023 for $175,000

Home Value

Trulia Estimate
$271K
Since last month
Decreased$7K (-2.4%)
Since last year
Increased$10K (+3.9%)
Since last sale
Increased$97K (+55.3%)
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 +94% in the last 10 years
MonthEstimated value
2026
September 2026$272K
August 2026$270K
July 2026$278K
June 2026$284K
May 2026$282K
April 2026$271K
March 2026$269K
February 2026$256K
January 2026$261K
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
92 Water Street, Chester, CT
0.60
Single-Family Home
$177,500
06/03/26
3
1
1,217
21 East Liberty Street, Chester, CT
0.42
Single-Family Home
$252,500
11/17/25
2
1
1,012
79 Middlesex Avenue, Chester, CT
0.12
Single-Family Home
$410,000
04/30/26
2
1
1,470
90 Water Street, Chester, CT
0.59
Single-Family Home
$177,500
06/03/26
1
1
1,034
5 Mitchell Lane, Deep River, CT
0.54
Single-Family Home
$366,000
12/29/25
2
1.5
1,081
61 Maple St, Chester, CT
0.54
Single-Family Home
$140,000
07/13/26
2
1
672
81 Main Street, Chester, CT
0.34
Single-Family Home
$618,000
06/11/26
2
2
1,128
54 Maple St, Chester, CT
0.60
Single-Family Home
$325,000
11/26/25
3
2
1,260
8 Phelps Lane, Deep River, CT
0.99
Single-Family Home
$331,500
07/21/26
2
1
912
8 Prospect Hill, Deep River, CT
0.98
Single-Family Home
$345,000
07/24/26
2
1
912

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
7 Old Depot Road, Chester, CT 06412
0.10
$975,000
4
2.5
3,149
Recently Sold
79 Middlesex Avenue, Chester, CT 06412
0.12
$410,000
2
1
1,470
Recently Sold
137 Main Street, Chester, CT 06412
0.09
$656,200
3
1.5
1,570
Off Market
142 Main Street, Chester, CT 06412
0.10
$729,000
3
2
2,188
Off Market
8 School Lane, Chester, CT 06412
0.13
$538,400
3
2
1,512
Off Market
9 School Lane, Chester, CT 06412
0.17
$519,800
3
1.5
1,388
Off Market
96 Middlesex Avenue, Chester, CT 06412
0.24
$1,406,800
4
3.5
3,153
Off Market
30 Middlesex Avenue, Chester, CT 06412
0.24
$420,900
2
1.5
1,362
Off Market
97 Main Street, Chester, CT 06412
0.25
$644,100
4
1.5
1,544
Off Market
19 Hickory Hill Drive, Chester, CT 06412
0.27
$838,300
3
3
2,646
Off Market
109A Middlesex Avenue, Chester, CT 06412
0.31
-
-
-
-
Off Market
26 Middlesex Avenue, Chester, CT 06412
0.29
$481,400
4
1.5
1,496
Off Market

Local Information

  • Map ViewExplore the area around 65 Middlesex Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1905
0.26 acre lot
792 sqft
$342/sqft

About this House

CLASSIC CAPE WITH ITS ORIGINAL CHARM. OPEN FRONT PORCH LEADING INTO A CHARMING ENTRY. ORIGINAL TRIM, HARDWOOD FLOORING. ENCLOSED REAR PORCH OVERLOOKING CARINI PARK. FULL WALKOUT BASEMENT WITH HIGH CEILINGS. SHORT DISTANCE TO DOWNTOWN AND MAJOR ROADS.
65 Middlesex Ave, Chester, CT 06412 is a 2 bedroom, 1 bathroom, 792 sqft single-family home in Chester Center, built in 1905. It last sold for $175,000 on Apr 26, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $271,200, with a rent estimate of $2,309/month.

Home Details for 65 Middlesex Ave

Interior Features

Heating & Cooling
Heating: Baseboard, OilHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 5
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood

Property Information

Year Built
Year Built: 1905Year Updated: 1978
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price and Tax history

DateEventPrice
Apr 26, 2023
Source: N/A
Sold
$175,000
Oct 25, 2019
Source: Smart MLS #170225615
Sold
$95,000
Aug 13, 2019
Source: Agent Provided
PriceChange
$109,900
Price increased by 8%
Jul 20, 2019
Source: Agent Provided
PriceChange
$101,650
Price decreased by 0%
Jul 19, 2019
Source: Agent Provided
PriceChange
$101,678
Price increased by 0%

Market trends in Chester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
9
3MoM

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 65 Middlesex Ave

  • What is 65 Middlesex Ave estimated to be worth?
    Trulia's estimated value for 65 Middlesex Ave in Chester, CT is $271,200.
  • What is the price history for 65 Middlesex Ave?
    65 Middlesex Ave in Chester, CT last sold for $175,000 in April 2023.
  • 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 65 Middlesex Ave?
    The closest schools to 65 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 65 Middlesex Ave?
    The lot at 65 Middlesex Ave in Chester, CT is about 0.26 acres (11,325 sq ft).

Apartments for Rent

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Off Market Homes Near 65 Middlesex Ave

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Homes for sale near 65 Middlesex Ave

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