Regency Key
Regency Real Estate
The Key To Your New Home
← Back to Search
MLS 24204497 For Sale Updated September 18, 2026
88 Winthrop Road

Chester, Connecticut 06412

$499,000
On market 7 days
88 Winthrop Road
1 / 24

About This Property

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.

Property Details

Interior

Heat
Hot Air — Oil
Cooling
Window Unit
Basement
Crawl Space

Exterior & Lot

Roof
Asphalt Shingle
Construction
Construction
Exterior Features
Balcony Shed
Lot Description
Secluded Treed
Garage & Parking
Attached Garage

Utilities & Systems

Water Source
Private Well
Sewer
Septic

Community & Schools

Elementary
Per Board of Ed
High
Per Board of Ed
Neighborhood
Cedar Lake

88 Winthrop Road

Chester , Connecticut 06412

$499,000

On market 7 days

Beds
3
Baths
3
SqFt
2,240
Type
Single Family
County Middlesex
Garage 2
Rooms -
Lot Size 33.97 Acres
Property Tax $8,198
Assessed Value $302,750
Year Built 1980
Style Contemporary
Zoning R-2

Payment Estimate

30-year fixed. Includes taxes; estimates only.

Estimated Monthly Payment
Open the full mortgage calculator →

Property Map

Map location is based on the property address.

Listing information is deemed reliable but not guaranteed and is sourced from the local MLS feed. Brokerage shown: 14300.

Menu