Date
Details
Price
Change
Source
9/10/2026
Listed
$499,000
—
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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Property Description
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.
Full Property Details
Full Property Details for 88 Winthrop Rd
General
- Price: $499,000
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24204497
- Updated: 9/10/2026
- Added to Site: 1 day(s) ago
Interior
- Number of Rooms: 8
- Appliances: None
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
- Primary Bedroom: Primary Bedroom, Upper
- Bedroom 1: Bedroom, Upper
- Bedroom 2: Bedroom, Upper
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 Friendly
School Information
- Elementary School: Per Board of Ed
- High School: Per Board of Ed
Community
- Community Name: Cedar Lake
Heating & Cooling
- Cooling Type: Window Unit
- Heating Type: Hot Air, Oil
- Heating Fuel: Oil
- Water Heater: Oil, Domestic
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Contemporary
- 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, Treed
Financial Considerations
- Assessment Amount: $302,750
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 941053
Listed by RE/MAX Heritage, Carlos Ortiz and RE/MAX Heritage, Timothy Sylvestre
We Value Your Privacy
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We Value Your Privacy
Listing agents
— 88 Winthrop Rd —
Carlos Ortiz
RE/MAX Heritage
Timothy Sylvestre
RE/MAX Heritage
Agent Contact: (860) 908-7809 Office Contact: (203) 646-2380
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 11 days ago
- 3Beds
- 2Total Baths
- 1,774Sq. Ft.
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 2Total Baths
- 1,288Sq. Ft.
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- Mobile Home
- Active
- Updated 11 hours ago
- 2Beds
- 1Total Bath
- 672Sq. Ft.
Listed by Shelly Cumpstone (860) 434-8600
- Single Family
- Active
- Updated 21 hours ago
- 4Beds
- 3Total Baths
- 1,928Sq. Ft.
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- Single Family
- Active
- Updated 1 day ago
- 5Beds
- 4Total Baths
- 2,518Sq. Ft.
- Single Family
- Active
- Updated 1 day ago
- 4Beds
- 3Total Baths
- 2,780Sq. Ft.
Listed by Shelly Cumpstone (860) 434-8600
- Single Family
- Active
- Updated 4 days ago
- 3Beds
- 3Total Baths
- 2,208Sq. Ft.
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- Single Family
- Closed
- 3Beds
- 2Total Baths
- 1,650Sq. Ft.
Listed by William Pitt Sotheby's Int'l
Sold by Gina Lavery
Sold by Gina Lavery
- Single Family
- Closed
- 3Beds
- 2Total Baths
- 1,842Sq. Ft.
Listed by Shelly Cumpstone
Sold by William Raveis Real Estate
Sold by William Raveis Real Estate
88 Winthrop Road, Chester, CT 06412 (MLS# 24204497) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 88 Winthrop Road is currently listed for $499,000 and was received on September 10, 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.