For Sale
Single family home for sale at 288 Middlesex Ave, Chester, CT 06412 | MLS# 24201816 | Listing updated on 2026-09-28
Photo 1 of Single family home for sale at 288 Middlesex Ave, Chester, CT 06412 | MLS# 24201816 | Listing updated on 2026-09-28
Photo 2 of Single family home for sale at 288 Middlesex Ave, Chester, CT 06412 | MLS# 24201816 | Listing updated on 2026-09-28
Photo 3 of Single family home for sale at 288 Middlesex Ave, Chester, CT 06412 | MLS# 24201816 | Listing updated on 2026-09-28
Photo 4 of Single family home for sale at 288 Middlesex Ave, Chester, CT 06412 | MLS# 24201816 | Listing updated on 2026-09-28
34+
Beds Icon

Street View

$2,995,000

Monthly Est:$14,907

  • Beds Icon4 Beds
  • Beds Icon
    6 Baths
  • Beds Icon4,926sqft

288 Middlesex Ave, Chester, CT 06412

$14,907/moEst:

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  • Single Family Residence

  • Built in 1800

  • $-- HOA

  • 2.65 acres lot

  • $608/sq.ft

Description

Set along a coveted and historic stretch of the Connecticut River, East View is a rare waterfront compound where extraordinary frontage, architectural integrity and Connecticut River Valley charm converge. Just over one mile from the village, this turnkey 2.65-acre estate offers 285 feet of direct river frontage, protected views and deep-water access. The river is the focal point framed by manicured grounds and a broad terrace leading gently to the water. A six-pile, deep water dock with two slips and a 16-ton lift is designed for serious boaters, while paddling is enjoyed from the floating dock and a small beach. Rooted in historic design and masterfully renovated in 2010, the residence blends timeless New England architecture with modern livability. Equally suited to weekends on the water, extended family gatherings, or multi-generational living, the property offers flexible spaces designed to entertain and live comfortably. Find a total of six garage bays for auto collections, boats, or a workshop. Minutes away discover Chester Village restaurants and artisans. Just across the river, the Goodspeed Opera House adds celebrated cultural dimension, and the neighboring seasonal Connecticut Valley Railroad evokes the region's rich history. The quiet elegance of East View offers a rare opportunity to experience the Connecticut River at its most extraordinary-where boating, history, culture, village life, and natural beauty converge.

  • Houzeo last checked: 11 hours ago
  • Listing updated: September 28, 2026 at 9:37 pm
  • Listing Provided by: Nancy Mesham | Coldwell Banker Realty
  • Source: SMART MLS-CT | MLS#: 24201816 SMART MLS-CT

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Middlesex County

  • City

    Chester

  • Neighborhood

    --

  • Year Built

    1800

  • HOA Fees

    -

  • Finished Area

    4,926 sqft

  • Lot Size

    2.65 acres lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24201816

  • MLS Status

    Active

  • Days on Market

    44

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 6

Interior

  • Appliances

    Gas Range, Convection Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Chiller

  • Cooling

    Central Air

  • Heating

    Oil

  • Sewer

    Septic

  • Exterior Features

    Balcony, Underground Utilities, Awnings, Gutters, Stone Wall, French Doors, Underground Sprinkler, Patio

  • Interior Features

    Audio System, Auto Garage Door Opener, Cable Available, Sauna, Security System

Construction

  • Year Built

    Year Built: 1800

  • Home type

    Single Family Residence

  • Roof

    Asphalt Shingle

  • Foundation Details

    Concrete

  • Architectural Style

    Colonial

Utilities & Energy

  • Water Source

    Private Well

  • Laundry Features

    Lower Level

  • Parking Features

    Attached Garage, Detached Garage

  • Basement

    Full, Storage, Interior Access, Partially Finished, Concrete Floor, Full With Hatchway

Other Features

  • Lot Features

    Professionally Landscaped, Water View

  • Subdivision Name

    N/a

Price History

DateEventPrice

08/26/2026

Source: mls_logoSMART MLS-CT #24201816

Listed for Sale

$2,995,000 -4.92%

$608/sqft

08/23/2026

Source: mls_logoSMART MLS-CT #24166793

Listing Removed

$3,150,000

$639/sqft

04/13/2026

Source: mls_logoSMART MLS-CT #24166793

Listed for Sale

$3,150,000 -6.67%

$639/sqft

12/27/2025

Source: mls_logoSMART MLS-CT #24124960

Listing Removed

$3,375,000

$685/sqft

12/27/2025

Source: mls_logoSMART MLS-CT #24124960

Off Market

$3,375,000 +264.86%

$685/sqft

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Getting Around 288 Middlesex Ave

Bike Score®

Bike Score

Somewhat Bikeable

1/100

Walk Score®

Walk Score

Car-Dependent

8/100

Data provided by Redfin

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Oct 09, 2026, 02:30PM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group