OFF MARKET

28 Middlesex Ave
Chester, CT 06412

Chester Center

3 Beds
3 Baths
1,582 sqft (on 0.45 acres)

$453,300

Trulia Estimate

as of Jul 6, 2026

Est. Refi. Payment $3,078/mo*

Refinance Your Home

$453,300

Trulia Estimate

as of Jul 6, 2026

Est. Refi. Payment $3,078/mo*

Refinance Your Home

3 Beds

3 Baths

1,582 sqft

(on 0.45 acres)

Local Information

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Schools1 Preschool School1 Elementary School1 Middle School1 High School
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Description

This single-family home is located at 28 Middlesex Ave, Chester, CT. 28 Middlesex Ave is in the Chester Center neighborhood in Chester, CT and in ZIP code 06412. This property has 3 bedrooms, 3 bathrooms and approximately 1,582 sqft of floor space. This property has a lot size of 0.45 acres and was built in 1900.

28 Middlesex Ave, Chester, CT 06412 is a 3 bedroom, 3 bathroom, 1,582 sqft single-family home in Chester Center, built in 1900. It last sold for $265,000 on Jan 12, 2021. It is currently off market. The Trulia Estimate is $453,300, with a rent estimate of $2,936/month.

Home Highlights

Parking

No Info

Outdoor

Patio, Deck

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 28 Middlesex Ave

Interior Features
Heating & Cooling Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility Stories: 2
Interior Details Number of Rooms: 7
Security Security System

Property Information
Year Built Year Built: 1900Year Updated: 1987
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial

Exterior Features
Exterior Home Features DeckExterior: OtherPatio

Lot Information
Lot Area: 0.45 acres

Price History for 28 Middlesex Ave

Date	Price	Event	Source
01/12/2021	$265,000	Sold	N/A
Recording Date 01/12/2021 Contract Date 01/07/2021 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Chester

Last updated May 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

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Property Tax and Assessment

Year	2025
Tax	$4,529
Assessment	$167,230

Home facts updated by county records

Comparable Sales for 28 Middlesex Ave

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
137 Main Street, Chester, CT	0.26	Single-Family Home	$610,000	08/01/25	3	1.5	1,570
23 Hickory Hill Dr, Chester, CT	0.23	Single-Family Home	$446,000	10/23/25	3	3	1,876
16 Hickory Hill Drive, Chester, CT	0.28	Single-Family Home	$755,000	11/19/25	3	2.5	1,896
5 Mitchell Lane, Deep River, CT	0.30	Single-Family Home	$366,000	12/29/25	2	1.5	1,081
35 Maple Street, Chester, CT	0.46	Single-Family Home	$780,000	01/15/26	3	2	1,772
54 Maple St, Chester, CT	0.56	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
9 Hickory Hill Drive, Chester, CT	0.33	Single-Family Home	$750,000	02/20/26	3	2.5	2,888
131 Middlesex Avenue, Chester, CT	0.75	Single-Family Home	$530,000	02/26/26	3	2.5	1,664
79 Middlesex Avenue, Chester, CT	0.38	Single-Family Home	$410,000	04/30/26	2	1	1,470

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $502,200
4 bd
1.5 ba
1,496 sqft
26 Middlesex Avenue,
Chester, CT 06412
Re/Max Valley Shore
OFF MARKET
Est. $436,900
2 bd
1.5 ba
1,362 sqft
30 Middlesex Avenue,
Chester, CT 06412
William Raveis Real Estate
OFF MARKET
Est. $582,600
3 bd
2 ba
1,963 sqft
16 Middlesex Avenue,
Chester, CT 06412
KW Legacy Partners
OFF MARKET
Est. $478,300
2 bd
1.5 ba
2,008 sqft
9 Gilbert Hill Road,
Chester, CT 06412
Coldwell Banker Realty
OFF MARKET
Est. $1,065,400
4 bd
3 ba
3,054 sqft
15 Gilbert Hill Road,
Chester, CT 06412
Berkshire Hathaway NE Prop.
OFF MARKET
Est. $1,208,600
4 bd
4.5 ba
3,351 sqft
25 Gilbert Hill Road,
Chester, CT 06412
William Pitt Sotheby's Int'l
OFF MARKET
Est. $776,400
3 bd
2 ba
2,188 sqft
142 Main Street,
Chester, CT 06412
Berkshire Hathaway NE Prop.
OFF MARKET
Est. $866,300
3 bd
3 ba
2,646 sqft
19 Hickory Hill Drive,
Chester, CT 06412
Select Realty Associates, LLC
OFF MARKET
Est. $647,200
3 bd
1.5 ba
1,570 sqft
137 Main Street,
Chester, CT 06412
William Pitt Sotheby's Int'l
SOLD
NOV 19, 2025
$755,000
3 bd
2.5 ba
1,896 sqft
16 Hickory Hill Drive,
Chester, CT 06412
William Raveis Real Estate
OFF MARKET
18 Hickory Hill Drive,
Chester, CT 06412
Houlihan Lawrence WD
OFF MARKET
Est. $665,700
3 bd
2.5 ba
1,838 sqft
22 Hickory Hill Drive,
Chester, CT 06412
Property Works New England

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Additional Cost

Assigned Schools

These are the assigned schools for 28 Middlesex 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.

Neighborhood Overview

Chester Center

5 Homes For You
Buy: $300k - $2.1m

See Local Highlights

Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

Apartments for Rent

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Contact for price
1-2 bd
1-2 ba
3 S Wig Hill Rd #f320a52c6,
Chester, CT 06412
Contact for price
1-2 bd
1-2 ba
132 Main St #f320a52c6,
Chester, CT 06412
Contact for price
1-2 bd
1-2 ba
10 Prospect St #f320a52c6,
Deep River, CT 06417
APPLY INSTANTLY
$8,000/mo
Total price
3 bd
3.5 ba
150 Ferry Rd #THE,
Old Lyme, CT 06371
APPLY INSTANTLY
$1,500/mo
Total price
1 bd
1 ba
Address Not Disclosed,
Deep River, CT 06417
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Chester
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Homes for sale near 28 Middlesex Ave

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1.47 ACRES
$650,000
4 bd
3 ba
2,560 sqft
38 Main Street,
Deep River, CT 06417
RE/MAX on the Bay
NEW - 10 HRS AGO
0.68 ACRES
$499,000
3 bd
2 ba
1,188 sqft
135 Middlesex Avenue,
Chester, CT 06412
Re/Max Valley Shore
0.52 ACRES
$399,900
2 bd
1 ba
1,817 sqft
79 River Street,
Deep River, CT 06417
Compass Connecticut, LLC
0.27 ACRES
$324,900
3 bd
1 ba
1,217 sqft
92 Water Street,
Chester, CT 06412
SSG Real Estate LLC
0.28 ACRES
$299,900
1 bd
1 ba
1,034 sqft
90 Water Street,
Chester, CT 06412
SSG Real Estate LLC
0.45 ACRES
$1,199,999
9 bd
9 ba
4,982 sqft
209 Main Street,
Deep River, CT 06417
William Pitt Sotheby's Int'l
3.2 ACRES
$2,200,000
4 bd
3.5 ba
3,957 sqft
47 East Kings Highway,
Chester, CT 06412
Chiarito Real Estate LLC
OPEN SUN, 12-2PM
4.4 ACRES
$779,000
3 bd
2.5 ba
2,433 sqft
257 West Elm Street,
Deep River, CT 06417
William Raveis Real Estate
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Off Market Homes Near 28 Middlesex Ave

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SOLD
JUN 29, 2026
$430,000
2 bd
1 ba
1,200 sqft
12 Jones Lane,
Deep River, CT 06417
William Raveis Real Estate
SOLD
JUN 25, 2026
$600,000
3 bd
2.5 ba
1,350 sqft
85 River Road #L4,
Essex, CT 06426
William Raveis Real Estate
SOLD
JUN 23, 2026
$350,000
41 Bushy Hill Road,
Ivoryton, CT 06442
Berkshire Hathaway NE Prop.
SOLD
JUN 23, 2026
$580,000
3 bd
2.5 ba
2,646 sqft
4 Acorn Drive,
East Haddam, CT 06423
RE/MAX on the Bay
SOLD
JUN 22, 2026
$540,000
3 bd
1.5 ba
1,392 sqft
177 Union Street,
Deep River, CT 06417
William Pitt Sotheby's Int'l
SOLD
JUN 18, 2026
$395,000
2 bd
2.5 ba
1,384 sqft
65 Main Street #24,
Essex, CT 06426
Re/Max Valley Shore
SOLD
JUN 15, 2026
$563,500
4 bd
1.5 ba
1,241 sqft
64 River Lane,
Deep River, CT 06417
Coldwell Banker Realty
SOLD
JUN 12, 2026
$470,000
3 bd
1.5 ba
1,092 sqft
19 Castle View Drive,
Chester, CT 06412
Great Estates, CT
SOLD
JUN 11, 2026
$618,000
2 bd
2 ba
1,128 sqft
81 Main Street,
Chester, CT 06412
William Pitt Sotheby's Int'l
SOLD
JUN 11, 2026
$560,000
3 bd
2.5 ba
1,739 sqft
3 Ferry Road,
Lyme, CT 06371
Coldwell Banker Realty
See more homes for sale in
Chester
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28 Middlesex Ave
Chester, CT 06412

$453,300

$453,300

Local Information