About 288 Middlesex Avenue
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.
Features of 288 Middlesex Avenue
| MLS® # | 24201816 |
|---|---|
| Price | $2,995,000 |
| Bedrooms | 4 |
| Bathrooms | 4/2 |
| Full Baths | 4 |
| Half Baths | 2 |
| Square Footage | 4,926 |
| Acres | 0.37 |
| Type | Single Family For Sale |
| Style | Colonial |
| Status | Active |
Community Information
| Address | 288 Middlesex Avenue |
|---|---|
| Area | N/A |
| City | Chester |
| County | Middlesex |
| State | Connecticut |
| Zip Code | 06412 |
Amenities
| Features | Thermopane Windows |
|---|---|
| Parking | Attached Garage, Detached Garage |
| Garage Spaces | 6 |
| Is Waterfront | Yes |
| Waterfront | River, Beach, Dock or Mooring, View |
| Has Pool | No |
Interior
| Interior Features | Audio System, Auto Garage Door Opener, Cable - Available, Sauna, Security System |
|---|---|
| Appliances | Gas Range, Convection Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Chiller |
| Heating | Hot Air, Oil |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 2 |
Exterior
| Exterior | Shake, Cedar |
|---|---|
| Exterior Features | Balcony, Underground Utilities, Awnings, Gutters, Stone Wall, French Doors, Underground Sprinkler, Patio |
| Lot Description | Professionally Landscaped, Water View |
| Roof | Asphalt Shingle |
| Foundation | Concrete |
School Information
| Elementary | Chester |
|---|---|
| Middle | Winthrop |
| High | Valley |
Additional Information
| Date Listed | August 26th, 2026 |
|---|---|
| Days on Market | 13 |
| Zoning | R-2 |
| RE / Bank Owned | No |
Listing Details
| Office | Coldwell Banker Realty |
|---|
