288 Middlesex Avenue
Chester, Connecticut 06412
- Beds
- 4
- Baths
- 4 | 2
- SqFt
- 4,926
- Acres
- 0.37
- Year Built
- 1800
- Property Type
- Single Family

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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
Active Listings
7
4 under contract
Median List Price
$650,000
7 active listings
Median Closed Price
$565,000
36 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per 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
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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.