288 Middlesex Avenue
Chester, CT 06412
$2,995,000
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, 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.
| Listing Id: | 24201816 |
|---|---|
| List Price: | $2,995,000 |
| Property Type: | Single Family |
| Status: | Active |
| Bank Owned Property: | No |
| Beds Total: | 4 |
| Baths Full: | 4 |
| Baths Half: | 2 |
| Living Area Sqft Per Public Record: | 4,626 |
| Property Tax: | $26,139 |
| Acres: | 2.65 |
| Style: | Colonial |
| Direct Waterfront Yn: | Yes |
| City: | Chester |
| County: | Middlesex |
| Postal Code: | 06412 |
| Year Built: | 1800 |
| Acres Source: | Public Records |
| Agent Owner Yn: | No |
| Appliances Included: | Gas Range, Convection Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Chiller |
| Assessed Value: | $913,010 |
| Attic Description: | Unfinished, Access Via Hatch |
| Attic Yn: | Yes |
| Basement Description: | Yes |
| Basement Description: | Full,Storage,Interior Access,Partially Finished,Concrete Floor,Full With Hatchway |
| Baths Total: | 6 |
| Color: | Grey |
| Comp Only Manual Yn: | No |
| Cooling System: | Central Air |
| Current Price: | $2,995,000.00 |
| Directions: | Middlesex Avenue east (river) side. Garage at the top of the drive belongs to this home as well as the attached 3-car, heated garage. Follow driveway to the end. |
| Display Fair Market Value Yn: | No |
| Elementary School: | Chester |
| Encumbrances Restrictions: | Easements, Right of Way |
| Energy Features: | Thermopane Windows |
| Exterior Features: | Balcony, Underground Utilities, Awnings, Gutters, Stone Wall, French Doors, Underground Sprinkler, Patio |
| Exterior Siding: | Shake, Cedar |
| Fireplaces Total: | 2 |
| Flood Zone Yn: | No |
| Foundation Type: | Concrete |
| Fuel Tank Location: | In Basement |
| Garage & Parking: | Attached Garage, Detached Garage |
| Garages Number: | 6 |
| Heat Fuel Type: | Oil |
| Heat Type: | Hot Air |
| High School: | Valley |
| Home Automation: | Built In Audio, Entertainment System, Security System, Thermostat(s), Wired For Audio |
| Home Owner's Assocation: | No |
| Home Warranty Offered Yn: | No |
| Hot Water Description: | Oil, 50 Gallon Tank |
| Interior Features: | Audio System, Auto Garage Door Opener, Cable - Available, Sauna, Security System |
| Laundry Room Info: | Lower Level |
| Listing Contract Date: | 2026-08-25 |
| Lot Description: | Professionally Landscaped, Water View |
| Middle Jr High School: | Winthrop |
| Mil Rate Total: | $27.78 |
| Status: | Active |
| Nearby Amenities: | Library, Medical Facilities, Park, Public Rec Facilities, Shopping/Mall |
| New Construction Type: | No/Resale |
| Occupied By: | Owner |
| Original List Price: | $2,995,000 |
| Parcel Number: | 941338 |
| Parking Total Spaces: | 6 |
| Possession Availability: | Negotiable |
| Potential Short Sale: | No |
| Preferred Phone: | (860) 227-9071 |
| Price: | $2,995,000 |
| Remarks Public Addendum: | Chester taxes $25, 363 and Haddam taxes $758 for a total of $26, 139 |
| Roof Information: | Asphalt Shingle |
| Rooms Additional: | Foyer, Gym, Mud Room, Steam/Sauna |
| Sewage System: | Septic |
| Sign Yn: | No |
| Sq Ft Est Heated Above Grade: | 4,626 |
| Sq Ft Est Heated Below Grade: | 300 |
| Sq Ft Total: | 4,926 |
| Swimming Pool Yn: | No |
| Tax Year: | July 2026-June 2027 |
| Total Rooms: | 9 |
| Under Agreement Yn: | No |
| Waterfront Description: | River, Beach, Dock or Mooring, View |
| Water Source: | Private Well |
| Year Built Source: | Public Records |
| Zoning: | R-2 |
Listing Courtesy of: Coldwell Banker Realty
Listing Agent: Nancy Mesham
(860) 227-9071
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Smart MLS Inc. data last updated on October 08, 2026 06:45 PM - ET
Property Last Updated: October 08, 2026 06:45 PM - ET