$3,375,000

288 Middlesex Ave Chester, CT 06412

Estimated payment $20,041/month

Total Views 310
4 Beds
6 Baths
4,926 Sq Ft
$685 Price per Sq Ft

Highlights

  • Sauna
  • Sub-Zero Refrigerator
  • 2.65 Acre Lot
  • Valley Regional High School Rated A-
  • Waterfront
  • Colonial Architecture

About This Home

East View is a long-admired Connecticut Riverfront property, a rare offering that perfectly marries historic provenance with elevated modern living. The circa 1800 home was masterfully renovated and expanded in 2010 with an architect's eye and a reverence for its storied past. Meticulous attention to detail is found in the extensive millwork, custom built-ins and hand-hewn beams lending warmth and character throughout. Expansive windows frame water views from nearly every room - north to the Haddam bridge and south across Lord's Island. The kitchen is the heart of this home with a grand center island, top end appliances and custom cabinetry. The adjacent living and dining rooms allow for effortless entertaining. There is a handsome family room with wet bar, a library and office. Sunrise over the river greets you in the private primary bedroom, a sanctuary with a balcony. Three additional bedrooms are sited on the north end of the home with two full baths. You will find a home theatre/media room and a gym with sauna-spaces designed to restore mind and body. Outdoors, the grounds slope gently from the bluestone patio to 285' of water frontage where a six-pile, two-slip dock awaits. Completely re-engineered and rebuilt with a 16-ton lift and an additional floating dock, this is a captain's dream. At low tide, stone steps reveal a sandy beach, perfect for a dip or kayaking. For vehicles, find a heated, 3-bay garage attached and an additional 3 bay garage with storage

Listing Agent

Nancy Mesham

Coldwell Banker Realty License #RES.0760007 Listed on: 09/08/2025

Coldwell Banker Realty

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $24,724

Year Built

  • Built in 1800

Lot Details

  • 2.65 Acre Lot
  • Waterfront
  • Stone Wall
  • Sprinkler System
  • Property is zoned R-2

Home Design

  • Colonial Architecture
  • Concrete Foundation
  • Frame Construction
  • Asphalt Shingled Roof
  • Cedar Siding
  • Shake Siding

Interior Spaces

  • Entertainment System
  • Built In Speakers
  • Sound System
  • 2 Fireplaces
  • Thermal Windows
  • Awning
  • French Doors
  • Mud Room
  • Entrance Foyer
  • Sauna
  • Concrete Flooring

Kitchen

  • Gas Range
  • Range Hood
  • Microwave
  • Sub-Zero Refrigerator
  • Dishwasher
  • Wine Cooler

Bedrooms and Bathrooms

  • 4 Bedrooms

Laundry

  • Laundry on lower level
  • Dryer
  • Washer

Attic

  • Unfinished Attic
  • Attic or Crawl Hatchway Insulated

Partially Finished Basement

  • Basement Fills Entire Space Under The House
  • Interior Basement Entry
  • Basement Storage

Home Security

  • Home Security System
  • Smart Thermostat

Parking

  • 6 Car Garage
  • Automatic Garage Door Opener

Outdoor Features

  • Balcony
  • Patio
  • Rain Gutters

Location

  • Property is near shops

Schools

  • Chester Elementary School
  • Winthrop Middle School
  • Valley High School

Utilities

  • Zoned Heating and Cooling System
  • Heating System Uses Oil
  • Underground Utilities
  • Private Company Owned Well
  • Oil Water Heater
  • Fuel Tank Located in Basement
  • Cable TV Available

Listing and Financial Details

  • Assessor Parcel Number 941338

Home Details

Home Type

Single Family

Est. Annual Taxes

$24,724

Year Built

Built in 1800

Lot Details

0

Listing Details

  • Neighborhood: N/A
  • Property Type: Single Family For Sale
  • Style: Colonial
  • Sq Ft Est Heated Above Grade: 4626
  • Sq Ft Est Heated Below Grade: 300
  • Total Sq Ft: 4926
  • Year Built: 1800
  • New Construction: No/Resale
  • Nearby Amenities: Library, Medical Facilities, Park, Public Rec Facilities, Shopping/Mall
  • Remarks Public Addendum: perfect for the enthusiast. Set on 2.65 acres this property offers elegance, privacy and a front-row seat to the natural beauty of the Connecticut River just over one mile to Chester Village and a bit more than two hours from New York.
  • Direct Waterfront: Yes
  • Encumbrances Restrictions: Easements, Right of Way
  • Home Warranty Offered: No
  • Directions: Middlesex Avenue water side. Follow driveway to the end.
  • Living Area Sq Ft Per Public Record: 4626
  • Street Type: Avenue
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 4
  • Total Bathrooms: 6
  • Full Bathrooms: 4
  • Half Bathrooms: 2
  • Fireplaces: 2
  • Attic Description: Unfinished, Access Via Hatch
  • Basement Description: Full, Storage, Interior Access, Partially Finished, Concrete Floor, Full With Hatchway
  • Interior Amenities: 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
  • Additional Rooms: Foyer, Gym, Mud Room, Steam/Sauna
  • Laundry Room Info: Lower Level
  • Attic: Yes
  • Home Automation: Built In Audio, Entertainment System, Security System, Thermostat(s), Wired For Audio
  • Street Number Modifier: 288

Exterior Features

  • Exterior Features: Balcony, Underground Utilities, Awnings, Gutters, Stone Wall, French Doors, Underground Sprinkler, Patio
  • Exterior Siding: Shake, Cedar
  • Foundation Type: Concrete
  • Roof Information: Asphalt Shingle
  • Waterfront Description: River Dock or Mooring View
  • Swimming Pool: No
  • Construction Description: Frame

Garage/Parking

  • Garages Number: 6
  • Garage And Parking: Attached Garage, Detached Garage

Utilities

  • Cooling System: Central Air
  • Heat Type: Hot Air, Zoned
  • Heat Fuel Type: Oil
  • Fuel Tank Location: In Basement
  • Hot Water Description: Oil, 50 Gallon Tank
  • Water Source: Private Well
  • Sewer: Septic

Schools

  • Elementary School: Chester
  • Middle School: Winthrop
  • High School: Valley

Green Features

  • Energy Features: Thermopane Windows

Lot Info

  • Acres: 2.65
  • Lot Description: Professionally Landscaped Water View
  • Flood Zone: No
  • Zoning: R-2
  • Parcel #: 941338

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 24724
  • Total Assessed Value: 913010
  • Mil Rate Total: 27.08

MLS Schools

  • Elementary School: Chester
  • Middle Jr High School: Winthrop
  • High School: Valley

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $24,724 $913,010 $410,760 $502,250
2024 $22,323 $913,010 $410,760 $502,250
2023 $21,400 $720,530 $392,510 $328,020
2022 $21,256 $720,530 $392,510 $328,020
2021 $21,256 $720,530 $392,510 $328,020
2020 $1 $720,530 $392,510 $328,020
2019 $20,744 $720,530 $392,510 $328,020
2018 $20,360 $751,010 $436,450 $314,560
2017 $19,797 $751,010 $436,450 $314,560
2016 $15,140 $751,010 $436,450 $314,560
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
09/11/2025 09/11/25 For Sale $3,375,000 -- $685 / Sq Ft
Source: SmartMLS

Purchase History

Date Type Sale Price Title Company
Warranty Deed $925,000 --
Warranty Deed $925,000 --
Executors Deed $267,900 --
Executors Deed $267,900 --
Source: Public Records

Source: SmartMLS

MLS Number: 24124960

SmartMLS

APN: CHES-000004-000000-000015