Active Under Contract
Single family home for sale at 88 Winthrop Rd, Chester, CT 06412 | MLS# 24204497 | Listing updated on 2026-09-21
Photo 1 of Single family home for sale at 88 Winthrop Rd, Chester, CT 06412 | MLS# 24204497 | Listing updated on 2026-09-21
Photo 2 of Single family home for sale at 88 Winthrop Rd, Chester, CT 06412 | MLS# 24204497 | Listing updated on 2026-09-21
Photo 3 of Single family home for sale at 88 Winthrop Rd, Chester, CT 06412 | MLS# 24204497 | Listing updated on 2026-09-21
Photo 4 of Single family home for sale at 88 Winthrop Rd, Chester, CT 06412 | MLS# 24204497 | Listing updated on 2026-09-21
20+
Beds Icon

Street View

$499,000

Monthly Est:$2,484

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,240sqft

88 Winthrop Rd, Chester, CT 06412

$2,484/moEst:

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  • Single Family Residence

  • Built in 1980

  • $-- HOA

  • 33.97 acres lot

  • $223/sq.ft

Description

Set on nearly 34 acres and directly abutting state forest, this unique contemporary home offers privacy, space, and endless potential. The open-concept interior features soaring cathedral ceilings and exposed beams, creating a dramatic and inviting living space. The home offers 3 bedrooms, 2.5 bathrooms, and an oversized 2-car attached garage. A separate approximately 800-square-foot barn/shop provides additional workspace, storage, or hobby potential and includes a dedicated garage bay. This home is an excellent opportunity for a buyer looking to restore and customize the property to their vision. With substantial acreage, direct access to nature, and versatile outbuildings, this property presents a rare opportunity to create a private estate, homestead, or retreat.

  • Houzeo last checked: 6 minutes ago
  • Listing updated: September 21, 2026 at 8:24 pm
  • Listing Provided by: Carlos Ortiz | RE/MAX Heritage
  • Source: SMART MLS-CT | MLS#: 24204497 SMART MLS-CT

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Middlesex County

  • City

    Chester

  • Neighborhood

    --

  • Year Built

    1980

  • HOA Fees

    -

  • Finished Area

    2,240 sqft

  • Lot Size

    33.97 acres lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24204497

  • MLS Status

    Under Contract

  • Days on Market

    36

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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: 3

    Bathrooms: 3

Interior

  • Exterior Features

    Balcony, Shed

  • Cooling

    Window Unit

  • Heating

    Oil

  • Sewer

    Septic

  • Appliances

    None

Construction

  • Year Built

    Year Built: 1980

  • Home type

    Single Family Residence

  • Architectural Style

    Contemporary

  • Foundation Details

    Concrete

  • Roof

    Asphalt Shingle

Utilities & Energy

  • Parking Features

    Attached Garage

  • Basement

    Crawl Space

  • Water Source

    Private Well

Other Features

  • Lot Features

    Secluded, Treed

  • Subdivision Name

    Cedar Lake

Price History

DateEventPrice

09/21/2026

Source: mls_logoSMART MLS-CT #24204497

Contingent (Active Under Contract)

$499,000

$0/sqft

09/16/2026

Source: mls_logoSMART MLS-CT #24204497

Listed for Sale

$499,000 -23.23%

$0/sqft

09/03/2026

Source: mls_logoSMART MLS-CT #24201493

Listing Removed

$650,000

$0/sqft

08/24/2026

Source: mls_logoSMART MLS-CT #24201493

Listed for Sale

$650,000

$0/sqft

08/15/2026

Source: mls_logoSMART MLS-CT #24179377

Price Decreased

$650,000 -18.74%

$0/sqft

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Based on information provided to and compiled by the SMART MLS, Inc. through Oct 17, 2026, 07:45AM. 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