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135 Middlesex Avenue

Chester, Connecticut 06412

ACTIVE$499,000
Beds
3
Baths
2
SqFt
1,188
Acres
0.68
Year Built
1920
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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Waterfront

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!

Key Facts

City/Town
Chester
Neighborhood
N/A
Property / Style
Single Family · Cape Cod
Year Built
1920
Days on Market
22 days
Beds
3
Baths
2 full
Living Area
1,188 sq ft
Lot Size
0.68 acres
Property Taxes
$5,291 / Annually

Market Snapshot

The Chester Market

Single Family · trailing 12 months

Median Days on Market

33

9 active listings

Median $ / Sq Ft

$269

9 active listings

Sale-to-List Ratio

100.0%

36 sales

How this home compares

List Price

$499,000

vs $499,000 median

In line with median

Price / Sq Ft

$420

vs $269 median

56.1% above median

Days on Market

22 days

vs 33 days median

11 days fresher than median

Based on 9 active and 36 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of July 28, 2026.

Location

135 Middlesex Avenue, Chester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,151

per month

  • Principal & Interest$2,544
  • Property Taxes$441
  • Insurance$166
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Chester
Neighborhood
N/A
County
Middlesex

Residence

Property Type
Single Family
Style
Cape Cod
Year Built
1920
New Construction
No/Resale
Living Area
1,188 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Bottle Gas
Cooling
Central Air
Laundry
Lower Level
Appliances
Electric RangeRefrigeratorDishwasherWasherDryer
Basement
FullFull With Walk-Out

Exterior & Lot

Lot Size
0.68 acres
Zoning
R-5
Waterfront
Direct waterfront
Waterfront Details
PondView
Water Source
Public Water Connected
Sewer
Septic
Flood Zone
Yes
Construction
Vinyl SidingStucco
Color
Gray
Roof
Asphalt Shingle
Foundation
ConcreteStone
Exterior Features
DeckGutters
Lot Description
Sloping Lot

Listing & Financials

Property Taxes
$5,291 / Annually
Days on Market
22
MLS #
24189125
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Lisa Genovali

(860) 510-3293

Re/Max Valley Shore

(860) 388-1228

Co-Listed By

Edward Kelley

Re/Max Valley Shore

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/28/2026 at 4:20 AM UTC.