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288 Middlesex Avenue

Chester, Connecticut 06412

ACTIVE - NEW$2,995,000
Beds
4
Baths
4 | 2
SqFt
4,926
Acres
0.37
Year Built
1800
Matt Caiola

Matt Caiola

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WaterfrontDock / Mooring6-Car Garage2 FireplacesVirtual Tour

About This Home

Set along a coveted and historic stretch of the Connecticut River, East View is a rare waterfront compound where extraordinary frontage, architectural integrity and Connecticut River Valley charm converge. Just over one mile from the village, this turnkey 2.65-acre estate offers 285 feet of direct river frontage, protected views and deep-water access. The river is the focal point framed by manicured grounds and a broad terrace leading gently to the water. A six-pile dock deep water dock with two slips and a 16-ton lift is designed for serious boaters, while paddling is enjoyed from the floating dock and a small beach. Rooted in historic design and masterfully renovated in 2010, the residence blends timeless New England architecture with modern livability. Equally suited to weekends on the water, extended family gatherings, or multi-generational living, the property offers flexible spaces designed to entertain and live comfortably. Find a total of six garage bays for auto collections, boats, or a workshop. Minutes away discover Chester Village restaurants and artisans. Just across the river, the Goodspeed Opera House adds celebrated cultural dimension, and the neighboring seasonal Connecticut Valley Railroad evokes the region's rich history. The quiet elegance of East View offers a rare opportunity to experience the Connecticut River at its most extraordinary-where boating, history, culture, village life, and natural beauty converge.

Key Facts

City/Town
Chester
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1800
Days on Market
0 days
Beds
4
Baths
4 full · 2 half
Living Area
4,926 sq ft
Lot Size
0.37 acres
Garage / Parking
6 garage
Property Taxes
$26,139 / Annually

Market Snapshot

The Chester Market

Single Family · trailing 12 months

Median Days on Market

51

7 active listings

Median $ / Sq Ft

$290

7 active listings

Sale-to-List Ratio

100.0%

36 sales

How this home compares

List Price

$3.00M

vs $650,000 median

4.6× the median

Price / Sq Ft

$608

vs $290 median

2.1× the median

Days on Market

0 days

vs 51 days median

51 days fresher than median

Based on 7 active and 36 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of August 26, 2026.

Location

288 Middlesex Avenue, Chester, Connecticut

Property + 11 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$18,557

per month

  • Principal & Interest$15,381
  • Property Taxes$2,178
  • Insurance$998
  • 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
Colonial
Year Built
1800
New Construction
No/Resale
Living Area
4,926 sq ft
Below Grade
300 sq ft

Schools

Elementary
Chester
High
Valley

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
2
Laundry
Lower Level
Appliances
Gas RangeConvection OvenMicrowaveRange HoodSubzeroDishwasherWasherDryerWine Chiller
Basement
FullStorageInterior AccessPartially FinishedConcrete FloorFull With Hatchway
Interior Features
Audio SystemAuto Garage Door OpenerCable - AvailableSaunaSecurity System
Additional Rooms
FoyerGymMud RoomSteam/Sauna

Exterior & Lot

Lot Size
0.37 acres
Zoning
R-2
Garage / Parking
6 garage spacesAttached GarageDetached Garage
Waterfront
Direct waterfront
Waterfront Details
RiverBeachDock or MooringView
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
ShakeCedar
Color
Grey
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
BalconyUnderground UtilitiesAwningsGuttersStone WallFrench DoorsUnderground SprinklerPatio
Lot Description
Professionally LandscapedWater View

Listing & Financials

Property Taxes
$26,139 / Annually
Days on Market
0
MLS #
24201816
MLS Status
Active

Similar Properties

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Listed By

Nancy Mesham

(860) 227-9071

Coldwell Banker Realty

(860) 434-8600

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

The IDX display contains information sourced from SmartMLS, Inc. as of 8/26/2026. 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 8/26/2026 at 5:20 PM UTC.