CONTINGENT

Contingent

$475,000

Est. $3,258/mo —

•

1,188

sq ft

135 Middlesex Ave, Chester, CT 06412

About this home

NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want to walk away from; there's also sliders to the deck and a full bath. On the second floor there are three spacious bedrooms along with a second full bath. The whole house underwent full renovations between 2012-2013 including new kitchen, baths, gleaming oak flooring, foam insulation, new HVAC, new electrical; the updates continued along with a new roof in 2017, and just recently new carpeting on second floor, new stove and microwave plus a new dryer. Bring your creativity to finish the lower walk-out level with its charming brick architecture along with newer radiant-heated, poured concrete floors and french doors -- this could be an amazing walkout steps to the water! This house would be a perfect vacation rental.... Rent a few weeks/Stay a few weeks!

Single-familyProperty Type

1920Year Built

0.68 acresLot Size

$400Price/Sq.Ft.

Listed by Lisa Genovali • Re/Max Valley Shore

Listed by Edward Kelley • Re/Max Valley Shore

Contact: Agent Attribution Contact: (860) 510-3293 | Office Attribution Contact: (860) 388-1228

Source:Smart MLS #24189125

Payment calculator

$3,258 per month

Principal and interest$2,592

Property taxes

$511

HOA dues

Home insurance

$154

Utilities

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Affordability tools

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN SAT, 10AM TO 12PM
$563,000
3 beds2.5 baths1,998 sq ft
255 Rock Landing Rd, East Hampton, CT 06438
2.39 acre lot • Built 1780 • Listed 8 days
OPEN SAT, 11AM TO 2PM
$585,000
2 beds2.5 baths1,390 sq ft
182 Green Hill Rd, Madison, CT 06443
0.46 acre lot • 2 garage spots • Built 1951
OPEN SAT, 12PM TO 2PM
$549,900
4 beds2.5 baths1,982 sq ft
245 Chestnut Hill Rd, Killingworth, CT 06419
2 acre lot • 2 garage spots • Built 1982
OPEN SAT, 12PM TO 2PM
$549,900
3 beds2 baths2,280 sq ft
89 Brush Hill Rd, Lyme, CT 06371
1.1 acre lot • 2 garage spots • Built 1972
OPEN SAT, 12PM TO 2PM
$500,000
3 beds2.5 baths1,440 sq ft
173 Chestnut Hill Rd, Killingworth, CT 06419
3.8 acre lot • 2 garage spots • Built 1957
OPEN SAT, 2PM TO 4PM
$849,000
3 beds2.5 baths2,200 sq ft
151 - 153 East Main St #31, Clinton, CT 06413
$500 HOA • Garage • Built 2026
OPEN SAT, 2PM TO 4PM
$619,900
2 beds1 bath1,654 sq ft
15 Baxter Rd, Clinton, CT 06413
0.25 acre lot • 3 parking spots • Built 1965
OPEN SUN, 2AM TO 4PM
$895,000
3 beds2 baths3,032 sq ft
24 Indian Dr, Clinton, CT 06413
0.27 acre lot • 2 garage spots • Built 1968
OPEN SUN, 11AM TO 1PM
$435,000
3 beds2 baths1,320 sq ft
102 Long Hill Rd, Clinton, CT 06413
0.63 acre lot • Garage • Built 1955
OPEN SUN, 12PM TO 2PM
$740,000
3 beds3 baths2,355 sq ft
1340 Old Clinton Rd #10, Westbrook, CT 06498
Garage • Built 2000 • Listed 10 days

Around this home

Schools

K - 12
Preschool & daycare

Chester Elementary School

Public PreK-6 • Assigned • 1.1mi

7/10

John Winthrop Middle School

Public 7-8 • Assigned • 3.3mi

6/10

Valley Regional High School

Public 9-12 • Assigned • 2.8mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

135 Middlesex Ave · $475,000

DAYS ON MARKET

The average home goes pending in 44 days.

SALE-TO-LIST

Most homes are selling 1% above list price.

LIST PRICE

Median sale price in this area is $485,415. (2% higher than this home)

PRICE DROP

19% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Full basement with walk-out
Attic with crawl space and pull-down stairs
Seven total rooms

Bedrooms
Three bedrooms

Bathrooms
Two full bathrooms

Kitchen
Electric range, refrigerator, dishwasher

Laundry & utility
Washer and dryer
Laundry room on the lower level

Heating & cooling
Central air
Hot-air heating with bottle gas

Sale and tax history for 135 Middlesex Ave

Sale History
Tax History

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Year

Property tax

Land + Additions

Assessment*

2023

$4,168 (+0.7%)

$76,000 + $64,320

$140,320

2022

$4,139

$76,000 + $64,320

$140,320

2021

$4,139 (+3.1%)

$76,000 + $64,320

$140,320

2020

$4,016 (−0.6%)

$76,000 + $64,320

$140,320

2019

$4,040 (−1.4%)

$76,000 + $64,320

$140,320

2018

$4,096 (+2.9%)

$79,850 + $71,230

$151,080

2017

$3,982 (+3.1%)

$79,850 + $71,230

$151,080

2016

$3,863 (+3.0%)

$79,850 + $71,230

$151,080

2014

$3,750 (−0.4%)

$79,850 + $71,230

$151,080

2011

$3,766

$90,030 + $81,520

$171,550

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.68 Acres

Year renovated

1987

Finished Sq. Ft.

1,097

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,097

Year built

1920

Style

Single Family Residential

County

Middlesex County

APN

940942

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Climate risks

10/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 96° expected this year, 16 days in 30 years

6/10 Wind Factor

77% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Chester, CT • 06412

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

95/ 100

Exceptional sunlight

Sunscore

This home ranks in the top 23% for direct sun exposure in Chester. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.2 hrs

5.8 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 135 Middlesex Ave

$463,782

$11K under list price of $475K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $234K to $530K.

SOLD FEB 26, 2026
$530,000 Last sold price
3 beds2.5 baths1,664 sq ft
131 Middlesex Ave, Chester, CT 06412
$81/sq ft
10 years newer
SOLD MAR 3, 2026
$495,000 Last sold price
3 beds2.5 baths2,018 sq ft
21 River Ln, Deep River, CT 06417
$155/sq ft
46 years newer
SOLD AUG 25, 2026
$452,000 Last sold price
3 beds1.5 baths1,198 sq ft
1 Kirtland Ave, Chester, CT 06412
$23/sq ft
smaller lot
48 years newer
SOLD OCT 27, 2026
$315,000 Last sold price
3 beds1 bath1,104 sq ft
49 Essex St, Deep River, CT 06417
$115/sq ft
smaller lot
SOLD APR 30, 2026
$410,000 Last sold price
2 beds1 bath1,470 sq ft
79 Middlesex Ave, Chester, CT 06412
$121/sq ft
larger lot
32 years newer
SOLD JUL 23, 2026
$233,600 Last sold price
2 beds2 baths1,344 sq ft
3 KIRTLAND Ave, Chester, CT 06412
$226/sq ft
smaller lot
105 years newer

Rental earnings

Est. $2,337 per month, based on comparable rentals

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(203) 433-6390

Nearby similar homes

$2,995,000

4 beds5 baths4,926 sq ft

288 Middlesex Ave, Chester, CT 06412

Deep water access • Manicured grounds • Broad terrace

$199,500

1 bed1 bath480 sq ft

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Outdoor shower • Electric outlet • Path to the lake

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Remodeled retreat • Spacious living room • Impressive garage

3D WALKTHROUGH

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Extra parking • Paved parking • Great room

$699,900

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Granite countertops • Hardwood floors • 1.61 acre lot

$499,000

4 beds2 baths2,100 sq ft

4 Gates Way, Haddam, CT 06438

Hand-hewn beams • Brick chimney • Cast-iron radiators

Details provided by Smart MLS and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Affordability tools

Open houses

Nearby open houses (10)

Around this home

Schools

Lifestyle

Market insights

Property details

Sale and tax history for 135 Middlesex Ave

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 135 Middlesex Ave

This home may not be allowing tours right now

Nearby similar homes

More real estate resources