Date
Details
Price
Change
Source
5/08/2026
Listed
$799,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$799,900
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Property Description
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.
Full Property Details
Full Property Details for 88 Winthrop Rd
General
- Price: $799,900
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24179377
- Updated: 7/13/2026
- Added to Site: 66 day(s) ago
Interior
- Number of Rooms: 8
- Appliances: Oven/Range, Wall Oven, Refrigerator, Washer, Electric Dryer
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
- Primary Bedroom: Primary Bedroom, Main
- Bedroom 1: Bedroom, Upper
- Bedroom 2: Bedroom, Upper
Other Rooms
- Living Room: Living Room, Main
- Kitchen: Kitchen, Main
Exterior
- Exterior Features: Balcony, Shed
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Parking: Attached Garage
Location
- County: Middlesex
- Neighborhood: Cedar Lake
- Driving Directions: GPS
School Information
- Elementary School: Chester
- High School: Region 4
Community
- Community Name: Cedar Lake
Heating & Cooling
- Cooling Type: None
- Heating Type: Hot Air, Oil
- Heating Fuel: Oil
- Water Heater: Oil, Tank Size Unknown
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Contemporary, Farm House
- Construction Status: No/Resale
- Exterior Const.: Vertical Siding, Wood
- Basement Desc.: Crawl Space
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 2,240
- Above Ground: 2,240 Sq. Ft.
- Year Built: 1980
Lot Features
- Lot Size (Acres): 33.97
- Zoning: R-2
- Lot Description: Secluded, Some Wetlands, Treed, Level Lot
Water Features
- Water Front Desc.: View, Seasonal
Financial Considerations
- Assessment Amount: $302,750
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 941053
Listed by Re/Max Valley Shore, Peter Walsh
We Value Your Privacy
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We Value Your Privacy
Listing agent
— 88 Winthrop Rd —
Peter Walsh
Re/Max Valley Shore
Agent Contact: (860) 304-9288 Office Contact: (860) 388-1228
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 88 Winthrop Rd
School Districts:Chester School District, Regional High School District 04
| Name | Grades | Distance |
|---|---|---|
Chester Elementary School, Chester, CT 23 Ridge Road, Chester, CT 06412 | K-6 | 4.7 mi |
John Winthrop Middle School 1 Winthrop Road, Deep River, CT 06417 | 7-8 | 3 mi |
Valley Regional High School 256 Kelsey Hill Road, Deep River, CT 06417 | 9-12 | 3.4 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 88 Winthrop Rd
Tax History
Tax History for 88 Winthrop Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,198
11%
$302,750
—
2023
$7,402
7%
$302,750
30%
2023
$6,935
1%
$233,490
—
2022
$6,888
—
$233,490
—
2021
$6,888
3%
$233,490
—
2020
$6,682
-1%
$233,490
—
2019
$6,722
-5%
$233,490
-11%
2018
$7,096
3%
$261,760
—
2017
$6,900
3%
$261,760
—
2016
$6,693
1%
$261,760
—
2015
$6,628
2%
$261,760
—
2014
$6,497
3%
$261,760
-9%
2011
$6,326
—
$288,190
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 88 Winthrop Rd
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- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 3Total Baths
- 2,782Sq. Ft.
- Single Family
- Active
- Updated 9 days ago
- 3Beds
- 3Total Baths
- 1,476Sq. Ft.
- Single Family
- Active
- Updated 10 days ago
- 4Beds
- 3Total Baths
- 3,016Sq. Ft.
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- Single Family
- Active
- Updated 3 days ago
- 3Beds
- 2Total Baths
- 1,984Sq. Ft.
- Single Family
- Active
- Updated 6 days ago
- 4Beds
- 3Total Baths
- 3,012Sq. Ft.
Listed by Shelly Cumpstone (860) 434-8600
- Single Family
- Active
- Updated 5 days ago
- 3Beds
- 3Total Baths
- 1,726Sq. Ft.
Listed by Shelly Cumpstone (860) 434-8600
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- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 3Total Baths
- 2,782Sq. Ft.
- Mobile Home
- Active
- Updated 3 days ago
- 2Beds
- 2Total Baths
- 924Sq. Ft.
- Townhouse
- Active
- Updated 4 days ago
- 2Beds
- 3Total Baths
- 1,488Sq. Ft.
Listed by Mary McDonald (860) 227-3812
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- Single Family
- Closed
- 4Beds
- 3Total Baths
- 2,029Sq. Ft.
Listed by Peg Mitchel and Kyle Hinding
Sold by Preston Roth
Sold by Preston Roth
88 Winthrop Road, Chester, CT 06412 (MLS# 24179377) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 88 Winthrop Road is currently listed for $799,900 and was received on May 08, 2026. Want to learn more about 88 Winthrop Road? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.