288 Middlesex Turnpike

Chester, CT 06412

$3,150,000
Price
4
Beds
4,926 Sq. Ft.
$639 / Sq. Ft.
4,926
Sq. Ft.
$639
per Sq. Ft.
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Open: 4/25 11:00AM - 02:00PM
Open: 4/25 11:00AM - 02:00PM
Appoaching East View from the Connecticut River
A stunning renovation melding historic charm and modern amenities and capturing views from nearly every room.
2 slips, floating dock. Lift accomodates 16 ton vessel. Deep water dock.
Aerial view looking south toward Middlesex Yacht Club and Essex
Kitchen
Formal dining room open to the kitchen and living room
The living room. French doors lead to the terrace.
Wet bar adjacent the family room
And more views.
The family room
Main level office
Full bath in this space creates tremendous guest space if needed.
Media room.
The primary bedroom features two large walk in closets and a stunning bath with walk in shower and wonderful claw foot tub.
Upper level bedroom
Another upper level bedroom
The third bedroom on the second level.
The lower level gym has a sauna and half bath.
From the terrace
Dock has water and power
Extra 3-bay garage with storge loft
Looking north to the bridge. Watch for seaplanes!
A stunning compound
Incomparable views to Lord's Island, north to the East Haddam bridge and south to Deep River

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...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.
  1. Listed by Nancy Mesham • Coldwell Banker Realty
    P: (860)-227-9071 C: (860)-227-9071 nancy.mesham@cbmoves.com

Property Details for 288 Middlesex Turnpike

Basement Description
Full, Storage, Interior Access, Partially Finished, Concrete Floor, Full With Hatchway
Direct Waterfront
Yes
Garages Number
6
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Attached Garage, Detached Garage
Swimming Pool
No

Open Houses

Saturday, Apr 25th11:00 AM - 2:00 PM
PublicView contact
LISTING UPDATED: 04/23/2026 01:40 PM

Property Details for 288 Middlesex Turnpike

StatusActive
MLS #24166793
Days on Market12
Taxes$24,724 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1800
Lot Size2.65 AC / 115,434 SF
CountyMiddlesex County
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Location

Listing Courtesy of Coldwell Banker Realty, Nancy Mesham
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Building Information for 288 Middlesex Turnpike

Stories-Year Built1800Building Size-Lot Size2.65 AC / 115,434 SF

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$17,922 per month

30 year fixed, 6.46% Interest

Principal and Interest

$15,862

Property Taxes

$2,060

HOA Dues

$0

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Property Information for 288 Middlesex Turnpike

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Middlesex Avenue water side. Follow driveway to the end.
  • Elementary School: Chester
  • Flood Zone: No
  • High School: Valley
  • Latitude: 41.433018
  • Longitude: -72.45407
  • Middle Jr High School: Winthrop
  • Neighborhood Amenities: Library, Medical Facilities, Park, Public Rec Facilities, Shopping/Mall
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $24,724
Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, Underground Utilities, Awnings, Gutters, Stone Wall, French Doors, Underground Sprinkler, Patio
  • Waterfront Description: River, Dock or Mooring, View
Interior Features
  • Appliances Included: Gas Range, Convection Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Chiller
  • Attic Description: Unfinished, Access Via Hatch
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Home Automation: Built In Audio, Entertainment System, Security System, Thermostat(s), Wired For Audio
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Sauna, Security System
  • Laundry Room Info: Lower Level
  • Rooms Additional: Foyer, Gym, Mud Room, Steam/Sauna
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Built-In Hutch,Granite Counters,French Doors,Island,Hardwood Floor
  • Room Length: 24.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 18.0
Room 2
  • Room Entry Order: 10
  • Room Features: Hardwood Floor
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.0
Room 3
  • Room Entry Order: 11
  • Room Features: Hardwood Floor
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.0
Room 4
  • Room Entry Order: 12
  • Room Features: Half Bath,Steam/Sauna
  • Room Length: 17.0
  • Room Level: Lower
  • Room Type: Other
  • Room Width: 15.0
Room 5
  • Listing Key: 4F5C0AC570F346E8E063E201100AFBA0
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 17.0
Room 6
  • Room Entry Order: 3
  • Room Features: Gas Log Fireplace,French Doors,Hardwood Floor
  • Room Length: 31.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 15.0
Room 7
  • Room Entry Order: 4
  • Room Features: Book Shelves
  • Room Length: 11.0
  • Room Level: Main
  • Room Type: Library
  • Room Width: 9.0
Room 8
  • Room Entry Order: 5
  • Room Features: Book Shelves
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 11.0
Room 9
  • Listing Key: 4F5C0AC570F346E8E063E201100AFBA0
  • Room Entry Order: 6
  • Room Features: Wet Bar,Fireplace,French Doors,Hardwood Floor
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 17.0
Room 10
  • Room Entry Order: 7
  • Room Features: Palladian Window(s),9 ft+ Ceilings,Partial Bath,Hardwood Floor
  • Room Length: 32.0
  • Room Level: Upper
  • Room Type: Media Room
  • Room Width: 22.0
Room 11
  • Room Entry Order: 8
  • Room Features: Balcony/Deck,French Doors,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 19.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 13.0
Room 12
  • Room Entry Order: 9
  • Room Features: Walk-In Closet,Hardwood Floor
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Property
Property and Assessments
  • Color: Grey
  • Construction Description: Frame
  • Exterior Siding: Shake, Cedar
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1800
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Est Heated Below Grade: 300
  • Living Area SQFT Per Public Records: 4626
Lot Information
  • Lot Description: Professionally Landscaped, Water View
  • Parcel Number: 941338
  • Sq Ft Est Heated Above Grade: 4626.0
  • Sq Ft Total: 4926.0
  • Zoning: R-2
Utilities
  • Energy Features: Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, 50 Gallon Tank
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 288 Middlesex Turnpike

DateEvent & SourcePriceAppreciation
Jun 19, 2009

Closed (Public Record)

Public Record #272167222

$925,000

+10.8% / yr

Jun 4, 1997

Closed (Public Record)

Public Record #91991427

$267,900—
DateEvent & SourcePrice
06/19/2009

Closed (Public Record)

Public Record #272167222

$925,000

+10.8% / yr

06/04/1997

Closed (Public Record)

Public Record #91991427

$267,900

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 288 Middlesex Turnpike

Taxable ValueLand$410,760Additions$502,250Total$913,010
Tax Record2024$24,724 ($2,060 / month)
Home Facts
Beds4Baths5Total Finished SqFt4,626 SqFtAbove Grade Finished SqFt4,626 SqFtUnfinished Basement SqFt738 SqFtStories2Lot Size16,117 SqFtStyleSingle Family ResidenceYear Built1985Year Renovated1990ZoningR-2CountyMIDDLESEXAPNCSTR M:4 B:15Fireplace TypeHas Fireplace

Schools near 288 Middlesex Turnpike

This home is within Regional School District 04.
Rating
School
Type
Grades
Distance
Chester Elementary School
Public - PK to 6
John Winthrop Middle School
Public - 7 to 8
Valley Regional High School
Public - 9 to 12
Franklin Academy
Private - 8 to 12
Rating
School
Distance
Chester Elementary School
PublicPK to 6

John Winthrop Middle School
Public7 to 8

Valley Regional High School
Public9 to 12

Franklin Academy
Private8 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 288 Middlesex Turnpike, Chester, CT 06412

288 Middlesex Turnpike is a single family home for sale in Chester, CT 06412. This property was listed for sale on April 12, 2026 by Coldwell Banker Realty, it's currently listed at $3,150,000. It has been on the market for a total of 12 days and was last sold on June 19, 2009. This listing's school districts are Regional School District 04, Chester School District. Nearby schools include Chester Elementary School, John Winthrop Middle School and Valley Regional High School. 288 Middlesex Turnpike is a 4-bed, 6-bath, 4,926 sqft single family home built in 1800.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Coldwell Banker Realty, Nancy Mesham

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.