Date
Details
Price
Change
Source
4/12/2026
Listed
$3,150,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
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.
Full Property Details
Full Property Details for 288 Middlesex Ave
General
- Price: $3,150,000
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24166793
- Updated: 4/13/2026
- Added to Site: 2 day(s) ago
Interior
- Number of Rooms: 9
- Rooms/Areas: Foyer, Gym, Mud Room, Steam/Sauna
- Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Sauna, Security System
- Fireplace: Yes
- Number of Fireplaces: 2
- Appliances: Gas Range, Convection Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Chiller
Rooms
Bathrooms
- Total Bathrooms: 6
- Full Bathrooms: 4
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 4
- Primary Bedroom: Primary Bedroom - Balcony/Deck, French Doors, Full Bath, Walk-In Closet, Hardwood Floor, 19 x 13, Upper
- Bedroom 1: Bedroom - Hardwood Floor, 12 x 11, Upper
- Bedroom 2: Bedroom - Hardwood Floor, 14 x 11, Upper
- Bedroom 3: Bedroom - Walk-In Closet, Hardwood Floor, 16 x 12, Upper
Other Rooms
- Living Room: Living Room - Gas Log Fireplace, French Doors, Hardwood Floor, 31 x 15, Main
- Family Room: Family Room - Wet Bar, Fireplace, French Doors, Hardwood Floor, 18 x 17, Main
- Kitchen: Kitchen - 9 ft+ Ceilings, Built-In Hutch, Granite Counters, French Doors, Island, Hardwood Floor, 24 x 18, Main
- Dining Room: Dining Room - Hardwood Floor, 17 x 17, Main
- Office: Office - Book Shelves, 12 x 11, Main
- Library: Library - Book Shelves, 11 x 9, Main
- Theater/Media: Media Room - Palladian Window(s), 9 ft+ Ceilings, Partial Bath, Hardwood Floor, 32 x 22, Upper
- Laundry: Lower Level
- Other Room 1: Other - Half Bath, Steam/Sauna, 17 x 15, Lower
Exterior
- Exterior Features: Balcony, Underground Utilities, Awnings, Gutters, Stone Wall, French Doors, Underground Sprinkler, Patio
- Color: Grey
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 6
- Parking: Attached Garage, Detached Garage
Location
- County: Middlesex
- Driving Directions: Middlesex Avenue water side. Follow driveway to the end.
School Information
- Elementary School: Chester
- Middle School: Winthrop
- High School: Valley
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Air, Oil
- Heating Fuel: Oil
- Water Heater: Oil, 50 Gallon Tank
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Colonial
- Construction Status: No/Resale
- Exterior Const.: Shake, Cedar
- Basement Desc.: Full, Storage, Interior Access, Partially Finished, Concrete Floor, Full With Hatchway
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 4,926
- Above Ground: 4,626 Sq. Ft.
- Below Ground: 300 Sq. Ft.
- Year Built: 1800
Lot Features
- Lot Size (Acres): 2.65
- Zoning: R-2
- Lot Description: Professionally Landscaped, Water View
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Desc.: River, Dock or Mooring, View
Green Features
- Energy Features: Thermopane Windows
Financial Considerations
- Assessment Amount: $913,010
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 941338
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.
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Price & Sales History for 288 Middlesex Ave
Tax History
Tax History for 288 Middlesex Ave
Year
Property Taxes
Change
Tax Assessment
Change
2025
$24,724
11%
$913,010
—
2023
$22,323
4%
$913,010
27%
2023
$21,400
1%
$720,530
—
2022
$21,256
—
$720,530
—
2021
$21,256
3%
$720,530
—
2020
$20,622
-1%
$720,530
—
2019
$20,744
2%
$720,530
-4%
2018
$20,360
3%
$751,010
—
2017
$19,797
3%
$751,010
—
2016
$19,203
1%
$751,010
—
2015
$19,016
2%
$751,010
—
2014
$18,640
-9%
$751,010
-20%
2011
$20,504
—
$934,110
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 288 Middlesex Ave
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288 Middlesex Avenue, Chester, CT 06412 (MLS# 24166793) is a Single Family property with 4 bedrooms, 4 full bathrooms and 2 partial bathrooms. 288 Middlesex Avenue is currently listed for $3,150,000 and was received on April 12, 2026. This property is listed by Nancy Mesham from our Old Lyme/Old Saybrook/Essex Office.Want to learn more about 288 Middlesex Avenue? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.