29 Middlesex Ave, Chester, CT 06412
OFF MARKET

$451,100

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,416 sqft (on 0.59 acres)

29 Middlesex Ave, Chester, CT 06412

Chester Center
Est. Refi. Payment $3,130/mo*
Refinance Your Home

Home Value

Trulia Estimate
$451K
Since last month
Decreased$25K (-5.2%)
Since last year
Increased$10K (+2.2%)
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 +99% in the last 10 years
MonthEstimated value
2026
August 2026$454K
August 2026$451K
July 2026$479K
June 2026$495K
May 2026$486K
April 2026$454K
March 2026$449K
February 2026$424K
January 2026$437K
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
35 Maple Street, Chester, CT
0.41
Single-Family Home
$780,000
01/15/26
3
2
1,772
72 Winter Avenue, Deep River, CT
0.33
Single-Family Home
$320,000
08/26/26
3
3
1,836
16 Hickory Hill Drive, Chester, CT
0.22
Single-Family Home
$755,000
11/19/25
3
2.5
1,896
23 Hickory Hill Dr, Chester, CT
0.18
Single-Family Home
$446,000
10/23/25
3
3
1,876
54 Maple St, Chester, CT
0.51
Single-Family Home
$325,000
11/26/25
3
2
1,260
5 Mitchell Lane, Deep River, CT
0.34
Single-Family Home
$366,000
12/29/25
2
1.5
1,081
79 Middlesex Avenue, Chester, CT
0.37
Single-Family Home
$410,000
04/30/26
2
1
1,470
9 Hickory Hill Drive, Chester, CT
0.28
Single-Family Home
$750,000
02/20/26
3
2.5
2,888
7 Hickory Hill Drive, Chester, CT
0.30
Single-Family Home
$549,000
03/24/26
3
2.5
2,202
25 Spring Street, Chester, CT
0.59
Single-Family Home
$860,000
09/17/25
3
2.5
2,344

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
30 Middlesex Avenue, Chester, CT 06412
0.04
$420,900
2
1.5
1,362
Off Market
9 Gilbert Hill Road, Chester, CT 06412
0.08
$465,100
2
1.5
2,008
Off Market
26 Middlesex Avenue, Chester, CT 06412
0.07
$481,400
4
1.5
1,496
Off Market
15 Gilbert Hill Road, Chester, CT 06412
0.10
$1,083,500
4
3
3,054
Off Market
16 Middlesex Avenue, Chester, CT 06412
0.15
$561,600
3
2
1,963
Off Market
25 Gilbert Hill Road, Chester, CT 06412
0.20
$1,229,100
4
4.5
3,351
Off Market
19 Hickory Hill Drive, Chester, CT 06412
0.20
$838,300
3
3
2,646
Off Market
142 Main Street, Chester, CT 06412
0.19
$729,000
3
2
2,188
Off Market
16 Hickory Hill Drive, Chester, CT 06412
0.22
$755,000
3
2.5
1,896
Recently Sold
18 Hickory Hill Drive, Chester, CT 06412
0.23
-
-
-
-
Off Market
137 Main Street, Chester, CT 06412
0.24
$656,200
3
1.5
1,570
Off Market
22 Hickory Hill Drive, Chester, CT 06412
0.25
$631,300
3
2.5
1,838
Off Market

Local Information

  • Map ViewExplore the area around 29 Middlesex Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1860
0.59 acre lot
1,416 sqft
$319/sqft
Garage

About this House

This single-family home is located at 29 Middlesex Ave, Chester, CT. 29 Middlesex Ave is in the Chester Center neighborhood in Chester, CT and in ZIP code 06412. This property has 3 bedrooms, 2 bathrooms and approximately 1,416 sqft of floor space. This property has a lot size of 0.59 acres and was built in 1860.
29 Middlesex Ave, Chester, CT 06412 is a 3 bedroom, 2 bathroom, 1,416 sqft single-family home in Chester Center, built in 1860. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $451,100, with a rent estimate of $3,120/month.

Home Details for 29 Middlesex Ave

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1860Year Updated: 1986
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 0.59 acres

Price and Tax history

YearProperty taxTax assessment
2025
$5,893
$217,630
Home facts updated by county records

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 29 Middlesex Ave

  • What is 29 Middlesex Ave estimated to be worth?
    Trulia's estimated value for 29 Middlesex Ave in Chester, CT is $451,100.
  • 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 29 Middlesex Ave?
    The closest schools to 29 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 29 Middlesex Ave?
    The lot at 29 Middlesex Ave in Chester, CT is about 0.59 acres (25,700 sq ft).
  • Does 29 Middlesex Ave have a garage?
    Yes, 29 Middlesex Ave in Chester, CT has a garage.

Apartments for Rent

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Off Market Homes Near 29 Middlesex Ave

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Homes for sale near 29 Middlesex Ave

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