135 Middlesex Avenue
Chester, Connecticut 06412
- Beds
- 3
- Baths
- 2
- SqFt
- 1,188
- Acres
- 0.68
- Year Built
- 1920
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
9
4 under contract
Median List Price
$499,000
9 active listings
Median Closed Price
$610,000
36 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.