Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and terrace to a deepwater dock designed for serious boating enthusiasts, and onward to a beach-creating an immersive riverfront experience rarely found in the CT River Valley. Rooted in historic design and masterfully renovated in 2010, the residence reflects timeless New England architecture while incorporating modern livability. The result is a home that feels both enduring and refined. A standout feature for collector/hobbyists are six garage bays, offering exceptional space for auto enthusiasts, boating and recreational storage. Designed to accommodate a range of lifestyles, this offering is equally compelling as a luxury weekend retreat or a multi-generational compound, with space and setting that invite both privacy and gathering. Despite its seclusion, the estate remains connected to the vibrant charm of Chester Village. Adding to the setting's unique appeal, the seasonal Connecticut Valley Railroad introduces a nostalgic dimension, reflecting the rich area history. A rare offering where protected waterfront, architectural integrity and lifestyle converge. Welcome to East View.
For sale
$3,150,000
288 Middlesex Avenue, Chester, CT 06412
4beds
4,926sqft
Single Family Residence
Built in 1800
2.65 Acres Lot
$-- Zestimate®
$639/sqft
$-- HOA
What's special
Stunning turnkey waterfront compoundProtected viewsManicured groundsResidence and terraceRooted in historic designModern livabilityTimeless new england architecture
- 60 days |
- 898 |
- 49 |
Zillow last checked:
Listing updated:
Listed by:
Nancy Mesham Team,
Nancy Mesham (860)227-9071,
Coldwell Banker Realty 860-434-8600
Source: Smart MLS,MLS#: 24166793
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 6
- Full bathrooms: 4
- 1/2 bathrooms: 2
Rooms
- Room types: Gym, Steam/Sauna
Primary bedroom
- Features: Balcony/Deck, French Doors, Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 247 Square Feet
- Dimensions: 13 x 19
Bedroom
- Features: Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 192 Square Feet
- Dimensions: 12 x 16
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 132 Square Feet
- Dimensions: 11 x 12
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 154 Square Feet
- Dimensions: 11 x 14
Dining room
- Features: Hardwood Floor
- Level: Main
- Area: 289 Square Feet
- Dimensions: 17 x 17
Family room
- Features: Wet Bar, Fireplace, French Doors, Hardwood Floor
- Level: Main
- Area: 306 Square Feet
- Dimensions: 17 x 18
Kitchen
- Features: High Ceilings, Built-in Features, Granite Counters, French Doors, Kitchen Island, Hardwood Floor
- Level: Main
- Area: 432 Square Feet
- Dimensions: 18 x 24
Library
- Features: Bookcases
- Level: Main
- Area: 99 Square Feet
- Dimensions: 9 x 11
Living room
- Features: Gas Log Fireplace, French Doors, Hardwood Floor
- Level: Main
- Area: 465 Square Feet
- Dimensions: 15 x 31
Media room
- Features: Palladian Window(s), High Ceilings, Partial Bath, Hardwood Floor
- Level: Upper
- Area: 704 Square Feet
- Dimensions: 22 x 32
Office
- Features: Bookcases
- Level: Main
- Area: 132 Square Feet
- Dimensions: 11 x 12
Other
- Features: Half Bath, Steam/Sauna
- Level: Lower
- Area: 255 Square Feet
- Dimensions: 15 x 17
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Gas Range, Convection Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Cooler, Water Heater
- Laundry: Lower Level, Mud Room
Features
- Sound System, Sauna, Entrance Foyer, Smart Thermostat, Wired for Sound
- Doors: French Doors
- Windows: Thermopane Windows
- Basement: Full,Storage Space,Interior Entry,Partially Finished,Concrete
- Attic: Access Via Hatch
- Number of fireplaces: 2
Interior area
- Total structure area: 4,926
- Total interior livable area: 4,926 sqft
- Finished area above ground: 4,626
- Finished area below ground: 300
Video & virtual tour
Property
Parking
- Total spaces: 6
- Parking features: Attached, Detached, Garage Door Opener
- Attached garage spaces: 6
Features
- Patio & porch: Patio
- Exterior features: Balcony, Awning(s), Rain Gutters, Stone Wall, Underground Sprinkler
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, River Front, Dock or Mooring
Lot
- Size: 2.65 Acres
- Features: Landscaped
Details
- Parcel number: 941338
- Zoning: R-2
- Other equipment: Entertainment System
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Shake Siding, Cedar
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1800
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Underground Utilities, Cable Available
Green energy
- Energy efficient items: Windows
Community & HOA
Community
- Features: Library, Medical Facilities, Park, Public Rec Facilities, Shopping/Mall
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Chester
Financial & listing details
- Price per square foot: $639/sqft
- Tax assessed value: $913,010
- Annual tax amount: $24,724
- Date on market: 4/13/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 4/13/2026 | Listed for sale | $3,150,000$639/sqft |
Source:  Smart MLS #24166793 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $144 +10.8% | $5,320 |
| 2024 | $130 -13.3% | $5,320 +5.1% |
| 2023 | $150 +0.7% | $5,060 |
| 2022 | $149 | $5,060 |
| 2021 | $149 +2.8% | $5,060 |
| 2020 | $145 -0.7% | $5,060 |
| 2019 | $146 +0.7% | $5,060 -5.6% |
| 2018 | $145 +2.8% | $5,360 |
| 2017 | $141 +30.6% | $5,360 |
| 2016 | $108 | $5,360 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 06412
Nearby schools
GreatSchools rating
- 7/10Chester Elementary SchoolGrades: PK-6Distance: 2.1 mi
- 4/10John Winthrop Middle SchoolGrades: 7-8Distance: 4.7 mi
- 7/10Valley Regional High SchoolGrades: 9-12Distance: 4.3 mi
Schools provided by the listing agent
- Elementary: Chester
- Middle: Winthrop
- High: Valley
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- Middlesex County
- Chester
- 06412
- 288 Middlesex Avenue
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