Login

288 Middlesex Avenue, Chester, CT 06412

Chester
Local realty services provided by:CENTURY 21 Classic Homes
288 Middlesex Avenue,Chester, CT 06412
$3,150,000
  • 4 Beds
  • 6 Baths
  • 4,926 sq. ft.
  • Single family
  • Active
Listed by: nancy mesham(860) 227-9071
Office: coldwell banker realty(860) 434-8600
MLS#:24166793
Source:CT

Price summary

  • Price:$3,150,000
  • Price per sq. ft.:$639.46

About this home

CENTURY 21 Fine Homes & Estates
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...

Contact an agent

contact an agent

Yes, I would like more information. Please use and/or share my information with an independent agent affiliated with the CENTURY 21®  brand to contact me about my real estate needs. By clicking Send message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an independent agent affiliated with the CENTURY 21®  brand is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE® , Coldwell Banker® , Corcoran® , ERA® , Sotheby's International Realty® ). I acknowledge that I have read and agree to theTerms of useandPrivacy notice

Home facts

  • Year built:1800
  • Listing ID #:24166793
  • Added:1 day(s) ago
  • Updated:April 15, 2026 at 11:33 AM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:6
  • Full bathrooms:4
  • Half bathrooms:2
  • Rooms Total:9
  • Kitchen Description:Convection Oven, Dishwasher, Gas Range, Microwave, Range Hood, Subzero, Wine Chiller
  • Basement Description:Concrete Floor, Full Basement, Full With Hatchway, Interior Access, Partially Finished, Storage
  • Living area:4,926 sq. ft.

Heating and cooling

  • Cooling:Central Air
  • Heating:Hot Air
  • Central air:Yes

Structure and exterior

  • Roof:Asphalt Shingle
  • Year built:1800
  • Building area:4,926 sq. ft.
  • Lot area:2.65 Acres
  • Lot Features:Professionally Landscaped, Water View
  • Architectural Style:Colonial
  • Construction Materials:Cedar, Shake
  • Exterior Features:Awnings, Balcony, French Doors, Gutters, Patio, Stone Wall, Underground Sprinkler, Underground Utilities

Schools

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

Utilities

  • Water:Private Well

Finances and disclosures

  • Price:$3,150,000
  • Price per sq. ft.:$639.46
  • Tax amount:$24,724 (July 2025-June 2026)

Features and amenities

  • Appliances:Convection Oven, Dishwasher, Dryer, Gas Range, Microwave, Range Hood, Subzero, Washer, Wine Chiller
  • Amenities:Audio System, Auto Garage Door Opener, Cable - Available, Library, Park, Public Rec Facilities, Sauna, Security System, Shopping/Mall

Parking

  • Parking description:Attached Garage, Detached Garage
  • Garage:Yes
The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

New listings near 288 Middlesex Avenue