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88 Winthrop Road, Chester, CT 06412

Single Family For Sale

$499,000
$223/sqft
88 Winthrop Road, Chester, CT
Active
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3
Bedrooms
3
Bathrooms
2,240
Sq Ft
33.97
Acres
1980
Year Built

About This Home

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.

Listed by Carlos Ortiz (860) 908-7809 with RE/MAX Heritage (203) 646-2380

Listing Snapshot

Price $499,000 Days on Our Site 5 days
Property Tax $8,198/yr Style Contemporary
Year Built 1980 Total Sq Ft 2,240
Lot Size 33.97 acres HOA Fees N/A
Bedrooms 3 Full Bathrooms 2
Total Rooms 8 Half Baths 1

Key Features

Appliances
  • None
Outdoor
  • Balcony
  • Shed

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 2
Garage Type Attached Garage

Systems & Utilities

Heat Hot Air
Fuel Oil
Cooling Window Unit
Hot Water Oil, Domestic
Water Private Well
Sewer Septic

Schools

Elem Per Board of Ed
High Per Board of Ed

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $683/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Sep 10, 2026 Listed $499,000

Frequently Asked Questions

How much does 88 Winthrop Road in Chester, CT cost?
This property is listed at $499,000, which works out to $223 per square foot.
How many bedrooms does 88 Winthrop Road have?
This home has 3 bedrooms and 3 bathrooms.
What is the square footage of 88 Winthrop Road?
The home is 2,240 square feet, situated on 33.97 acres.
When was 88 Winthrop Road in Chester built?
This property was built in 1980.
Is 88 Winthrop Road, Chester, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 88 Winthrop Road, Chester in?
This home is served by the Chester public school system, with Per Board of Ed as the elementary school and Per Board of Ed as the high school.
How do I schedule a tour of 88 Winthrop Road, Chester, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Carlos Ortiz · (860) 908-7809

RE/MAX Heritage · (203) 646-2380

MLS# 24204497 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Sep 16, 2026 12:33 AM UTC