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.
Est. $3,061 per month, based on comparable rentals
Sale and tax history for 88 Winthrop Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24204497
Nov 6, 2026
Sold
$500,000
$223/sq ft
Sep 21, 2026
Pending
—
Sep 16, 2026
Relisted
—
Sep 16, 2026
Listing Removed
—
Sep 10, 2026
Listed
$499,000
$223/sq ft
Smart MLS #24201493
Sep 3, 2026
Listing Removed
—
Aug 24, 2026
Listed
$650,000
$290/sq ft
Smart MLS #24179377
Sep 3, 2026
Listing Removed
—
Aug 15, 2026
Price Changed
$650,000
$290/sq ft
May 8, 2026
Listed
$799,900
$357/sq ft
Smart MLS #24081148
Dec 2, 2025
Listing Removed
—
Apr 1, 2025
Listed
$985,000
$440/sq ft
Smart MLS #24081139
Nov 26, 2025
Listing Removed
—
Mar 30, 2025
Listed
$985,000
$440/sq ft
Smart MLS #99018434
Jul 22, 2013
Listing Removed
—
Mar 1, 2013
Listed
$650,000
$290/sq ft
Smart MLS #M9114411
Jun 1, 2011
Listing Removed
—
Jan 14, 2009
Listed
$949,000
$424/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$6,935 (+0.7%)
$77,040 + $156,450
$233,490
2022
$6,888
$77,040 + $156,450
$233,490
2021
$6,888 (+3.1%)
$77,040 + $156,450
$233,490
2020
$6,682 (−0.6%)
$77,040 + $156,450
$233,490
2019
$6,722 (−5.3%)
$77,040 + $156,450
$233,490
2018
$7,096 (+2.8%)
$85,290 + $176,470
$261,760
2017
$6,900 (+3.1%)
$85,290 + $176,470
$261,760
2016
$6,693 (+3.0%)
$85,290 + $176,470
$261,760
2014
$6,497 (+2.7%)
$85,290 + $176,470
$261,760
2011
$6,326
$106,910 + $181,280
$288,190
Public record
Beds
2
Baths
2.5
Stories
2
Lot width
—
Lot depth
—
Lot size
33.97 Acres
Year renovated
1997
Sq. Ft.
2,240
Year built
1980
Style
Single Family Residential
County
Middlesex County
APN
941053
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 13, 2023.
Property details
Parking
Garage Information
Garage & Parking: Attached Garage
Garages Number: 2
Interior
Interior Information
Total Rooms: 8
Cooling System: Window Unit
Bathroom Information
# of Baths (Full): 2
# of Baths (Half): 1
Bedroom Information
Beds Total: 3
Room Information
Basement Description: Crawl Space
Has Attic
Attic Description: Access Via Hatch
Exterior
Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Vertical Siding, Wood
Exterior Features: Balcony, Shed
Lot Information
Lot Description: Secluded, Treed
Building Information
Foundation Type: Concrete
Construction Description: Frame
Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2240
Financial
Assessments Information
Assessed Value: $302,750
Utilities
Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Oil, Domestic
Heat Type: Hot Air
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Location
School Information
High School: Per Board of Ed
Elementary School: Per Board of Ed
Location Information
State: Connecticut
Directions: GPS Friendly
County: Middlesex
Public facts
Beds: 2
Baths: 2.5
Sq. Ft.: 2,240
Stories: 2.0
Lot Size: 33.97 acres
Style: Single Family Residential
Year Built: 1980
Year Renovated: 1997
County: Middlesex County
APN: 941053
Home facts updated by county records on Jul 13, 2023
Other
Documents & Disclosures
Supplement Count Public: 3
Around this home
Schools
Chester Elementary School
Public PreK-6 • Assigned • 3.3mi
7/10
John Winthrop Middle School
Public 7-8 • Assigned • 3.1mi
6/10
Valley Regional High School
Public 9-12 • Assigned • 3.3mi
7/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
4/10 Heat Factor
7 days above 93° expected this year, 16 days in 30 years
6/10 Wind Factor
70% chance of strong winds in next 30 years
4/10 Air Factor
3 unhealthy days expected this year, 5 days in 30 years
Provided by First Street
Historical weather
Chester, CT • 06412
Average low and high temperatures (°F)
34
21
36
22
51
33
60
42
68
51
80
60
83
66
80
59
76
57
64
47
54
38
39
25
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
94/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 28% for direct sun exposure in Chester. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10.2 hrs
6.2 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$715,000 – $865,000
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