Set on 33.97 private acres in beautiful Chester, CT, this inviting home offers space, privacy, and scenic views. The main level features a primary bedroom with a full bath, while upstairs you'll find 3 additional bedrooms with 2 full baths. The bright, open living room features soaring ceiling and a second floor balcony overlooking the main living space, creating an airy feel. Large south facing windows bring in abundant natural light and capture lovely views of the lightly wooded landscape. The home's attractive vertical wood siding adds character, while the expansive acreage provides a peaceful setting just minutes from the charm, shops and restaurants of Chester village.
For sale
$799,900
88 Winthrop Road, Chester, CT 06412
3beds
2,240sqft
:
Get pre-qualified$5,631/mo
Single Family Residence
Built in 1980
33.97 Acres Lot
$-- Zestimate®
$357/sqft
$-- HOA
What's special
Soaring ceilingAbundant natural lightLarge south facing windowsAttractive vertical wood siding
- 10 days |
- 575 |
- 31 |
Zillow last checked:
Listing updated:
Listed by:
Peter Walsh (860)304-9288,
Re/Max Valley Shore 860-388-1228
Source: Smart MLS,MLS#: 24179377
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Level: Main
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Kitchen
- Level: Main
Living room
- Level: Main
Heating
- Forced Air, Oil
Cooling
- None
Appliances
- Included: Oven/Range, Oven, Refrigerator, Washer, Dryer, Water Heater
Features
- Basement: Crawl Space
- Attic: Crawl Space,Access Via Hatch
- Has fireplace: No
Interior area
- Total structure area: 2,240
- Total interior livable area: 2,240 sqft
- Finished area above ground: 2,240
Property
Parking
- Total spaces: 2
- Parking features: Attached
- Attached garage spaces: 2
Features
- Exterior features: Balcony
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Seasonal
Lot
- Size: 33.97 Acres
- Features: Secluded, Wetlands, Wooded, Level
Details
- Additional structures: Shed(s)
- Parcel number: 941053
- Zoning: R-2
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary,Farm House
- Property subtype: Single Family Residence
Materials
- Vertical Siding, Wood Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1980
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & HOA
Community
- Subdivision: Cedar Lake
HOA
- Has HOA: No
Location
- Region: Chester
Financial & listing details
- Price per square foot: $357/sqft
- Tax assessed value: $302,750
- Annual tax amount: $8,198
- Date on market: 7/13/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 7/13/2026 | Listed for sale | $799,900-18.8%$357/sqft |
Source:  Smart MLS #24179377 Report a problem | ||
| 12/2/2025 | Listing removed | $985,000$440/sqft |
Source: Smart MLS #24081148 Report a problem | ||
| 4/1/2025 | Listed for sale | $985,000+15.9%$440/sqft |
Source: Smart MLS #24081148 Report a problem | ||
| 3/24/2021 | Listing removed | -- |
Source: Owner Report a problem | ||
| 11/11/2018 | Listing removed | $850,000$379/sqft |
Source: Owner Report a problem | ||
| 8/13/2018 | Listed for sale | $850,000+30.8%$379/sqft |
Source: Owner Report a problem | ||
| 7/23/2013 | Listing removed | $650,000$290/sqft |
Source: CENTURY 21 Scala Group #99018434 Report a problem | ||
| 3/2/2013 | Listed for sale | $650,000-31.5%$290/sqft |
Source: CENTURY 21 Access America #99018434 Report a problem | ||
| 5/25/2011 | Listing removed | $949,000$424/sqft |
Source: THIMBLE ISLAND REALTY LLC #M9114411 Report a problem | ||
| 2/26/2011 | Listed for sale | $949,000$424/sqft |
Source: THIMBLE ISLAND REALTY LLC #M9114411 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,198 +10.8% | $302,750 |
| 2024 | $7,402 +6.7% | $302,750 +29.7% |
| 2023 | $6,935 +0.7% | $233,490 |
| 2022 | $6,888 | $233,490 |
| 2021 | $6,888 +3.1% | $233,490 |
| 2020 | $6,682 -0.6% | $233,490 |
| 2019 | $6,722 -5.3% | $233,490 -10.8% |
| 2018 | $7,096 +2.8% | $261,760 |
| 2017 | $6,900 +4.1% | $261,760 |
| 2015 | $6,628 +2% | $261,760 |
| 2014 | $6,497 +2.7% | $261,760 -9.2% |
| 2013 | $6,326 -2.3% | $288,190 |
| 2012 | $6,476 +1.6% | $288,190 |
| 2011 | $6,372 | $288,190 |
| 2010 | $6,372 +4.7% | $288,190 |
| 2009 | $6,084 +16.5% | $288,190 +23.4% |
| 2006 | $5,223 +38.5% | $233,500 +53.8% |
| 2001 | $3,770 -17.4% | $151,850 -35.6% |
| 1995 | $4,566 | $235,970 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 06412
Nearby schools
GreatSchools rating
- 7/10Chester Elementary SchoolGrades: PK-6Distance: 3.3 mi
- 4/10John Winthrop Middle SchoolGrades: 7-8Distance: 3.1 mi
- 7/10Valley Regional High SchoolGrades: 9-12Distance: 3.3 mi
Schools provided by the listing agent
- Elementary: Chester
- High: Region 4
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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