Claudia Dixon

88 Winthrop Road

Chester, CT
$ 499,000 Beds 3 Baths 2.5 Sq 2,240
Monthly Estimate* How much can I afford?

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.

Single Family

  • Price
  • $ 499,000
  • City
  • Chester
  • Bedrooms
  • 3
  • Full Bathrooms
  • 2
  • County
  • Middlesex
  • Half Bathrooms
  • 1
  • Area
  • Lot Size
  • 33.97 Acres
  • Zip
  • 06412
  • Sqr Footage
  • 2,240
  • Year Built
  • 1980
  • Taxes
  • $ 8410
  • Style
  • MLS#
  • 24204497
Listed By: Carlos Ortiz 860-908-7809 with RE/MAX Heritage. - (203) 646-2380
Data Source: Smart MLS

Features

General

Zoning R-2
Neighborhood Cedar Lake
County Middlesex
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Under Contract
Acres 33.97
Directions GPS Friendly
High School Per Board of Ed
City Chester
Elementary School Per Board of Ed
Sq Ft Total 2240
DOM 3
Year Built 1980
Style Contemporary
Year Built Source Public Records

Interior Features

Cooling System Window Unit
Total Rooms 8
Basement Description Crawl Space

Exterior Features

Water Source Private Well
Lot Description Secluded,Treed

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Per Board of Ed Elementary School
Middle School Unknown Middle School
High School Per Board of Ed High School

Price History

9/10/2026 Listed $499,000

Property vs Zip Code Average in 06412

Price
AVG $800K
$500K
Taxes
AVG $9,066
$8,410
Year Built
AVG 1935
1980

In The Neighborhood

Areas That We Cover

88 Winthrop Road Chester, CT is a Single Family Home for sale at $499000 with 2240 sqft and a lot size of 33.97 Acres Acre(s). 88 Winthrop Road Chester has 3 bedrooms, 2 baths and was built in 1980. The property's zip code is 06412 which is in Chester, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Claudia Dixon

Claudia Dixon

Sales Associate

860-881-7725

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