88 Winthrop Road
Chester, Connecticut 06412
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,240
- Acres
- 33.97
- Year Built
- 1980
- Neighborhood
- Cedar Lake
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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.
Key Facts
- City/Town
- Chester
- Neighborhood
- Cedar Lake
- Property / Style
- Single Family · Contemporary
- Year Built
- 1980
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 2,240 sq ft
- Lot Size
- 33.97 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $8,198 / Annually
Market Snapshot
The Chester Market
Single Family · trailing 12 months
Active Listings
7
3 under contract
Median List Price
$499,000
7 active listings
Median Closed Price
$565,000
38 sales
Median Days on Market
21
7 active listings
Median $ / Sq Ft
$282
7 active listings
Sale-to-List Ratio
100.0%
38 sales
How this home compares
List Price
$499,000
vs $499,000 median
In line with median
Price / Sq Ft
$223
vs $282 median
20.9% below median
Days on Market
0 days
vs 21 days median
21 days fresher than median
Based on 7 active and 38 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of September 10, 2026.
Location
88 Winthrop Road, Chester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$2,592
- Property Taxes$683
- Insurance$166
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Chester
- Neighborhood
- Cedar Lake
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Contemporary
- Year Built
- 1980
- New Construction
- No/Resale
- Living Area
- 2,240 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Appliances
- None
- Basement
- Crawl Space
Exterior & Lot
- Lot Size
- 33.97 acres
- Zoning
- R-2
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vertical SidingWood
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- BalconyShed
- Lot Description
- SecludedTreed
Listing & Financials
- Property Taxes
- $8,198 / Annually
- Days on Market
- 0
- MLS #
- 24204497
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Timothy Sylvestre
RE/MAX Heritage
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/10/2026. This information 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 or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/10/2026 at 7:05 PM UTC.