Sold
Last Sold Price
4 beds2,264 sqft$169/sqft
86 Winthrop Rd, Chester, CT 06412
Single FamilyProperty Type
2.58 acresLot Size
1999Year Built
$169/sq ftPrice per sq ft
2 carsParking Spaces

Description

Meticulous inside & out. Professionally landscaped&privately set on 2.5+ Ac. Country kitchen,fp,hardwood flrs & crown moldings. Screened gazebo w/electric,perfect for dining & entertaining. Rec room & workshop. Walk up attic & unfin. Bonus room for expansion.Meticulous inside & out. Professionally landscaped&privately set on 2.5+ Ac. Country kitchen,fp,hardwood flrs & crown moldings. Screened gazebo w/electric,perfect for dining & entertaining. Rec room & workshop. Walk up attic & unfin. Bonus room for expansion.
Listing closed: 07/31/2009 12:00 AM • Source: SMARTMLS, MLS#: M9115685

Recent comparable sales

Median sold price

$425,000

Avg days on market

35

Sale-to-list ratio

100.6%

Chester, CT

9 comparable properties found

$450,000 | 2 Sypher Road, Chester, CT 06412
1

$450,000

Sold 01/24/25

4
Bedrooms
2,278
Square Feet
2
Acres
2

$440,000

Sold 07/24/26

4
Bedrooms
2
Bathrooms
1,683
Square Feet
5.4
Acres
a view of a house with a yard and large tree
1/35
3

$360,000

Sold 06/24/25

4
Bedrooms
2,109
Square Feet
1.32
Acres
a front view of a house with garden
1/22
4

$360,500

Sold 10/31/25

4
Bedrooms
2,059
Square Feet
0.38
Acres
$425,000 | 3037 Warfield Estates Terrace, Chester, VA 23831
1/2
5

$425,000

Sold 06/23/26

4
Bedrooms
2,028
Square Feet
0.39
Acres
$429,950 | 6784 Arbor Mdws Drive, Chester, VA 23831
1/35
6

$429,950

Sold 10/03/25

4
Bedrooms
2,408
Square Feet
0.27
Acres
a kitchen with stainless steel appliances granite countertop a refrigerator and a sink
1/21
7

$420,000

Sold 02/24/26

4
Bedrooms
1,965
Square Feet
0.34
Acres
$1,017,000 | 95 Cedar Swamp Road, Chester, CT 06412
8

$1,017,000

Sold 10/20/25

4
Bedrooms
4,341
Square Feet
2.95
Acres
a front view of a house with a yard
1/22
9

$420,000

Sold 09/22/25

4
Bedrooms
1,937
Square Feet
Unavailable
Acres

Location

Listing Courtesy of Century 21 Heritage Company, Hope Matthies-Rayner
Add your commute

Payment Calculator

$2,568 per month

30 year fixed, 6.71% Interest

Principal and Interest

$1,979

Property Taxes

$589

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 86 Winthrop Road

Property Details
  • Taxes: $7,065 / year
  • MLS Type: Residential
  • Basement Description: Full With Hatchway, Partially Finished
  • Garages Number: 2
  • Style: Colonial
  • Garage Parking Info: Attached Garage
  • Swimming Pool: No
Building Information
  • Year Built: 1999
  • Lot Size: 2.58 AC / 112,384 SF
Summary
Property and Location
  • Directions: Rt 9, exit 6, west on rt 148. Left on rt 145 (winthrop rd). #86 Set back on right. (No sign)
  • Elementary School: Chester
  • High School: Valley
  • Latitude: 41.378822
  • Longitude: -72.50933
  • State: Connecticut
HOA and Fees
  • Property Tax: $7,065
Interior and Exterior Features
Exterior Features
  • Exterior Features: Garden Area, Gazebo, Storage Building
Interior Features
  • Appliances Included: Dishwasher, Disposal, Oven/Range, Refrigerator, Range Hood
  • Attic Description: Walk-up
  • Heat Type: Baseboard
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Cable - Available, Auto Garage Door Opener
  • Laundry Room Location: First Floor
  • Rooms Additional: Workshop
  • Room Count: 7
  • Rooms Total: 7
Room 1
  • Room Entry Order: 1
  • Room Length: 13.0
  • Room Type: Bedroom
  • Room Width: 11.0
Room 2
  • Room Entry Order: 1
  • Room Length: 13.0
  • Room Type: Bedroom
  • Room Width: 11.0
Room 3
  • Room Entry Order: 2
  • Room Length: 13.0
  • Room Type: Bedroom
  • Room Width: 13.0
Room 4
  • Room Entry Order: 2
  • Room Length: 13.0
  • Room Type: Bedroom
  • Room Width: 13.0
Room 5
  • Room Entry Order: 3
  • Room Length: 11.0
  • Room Type: Bedroom
  • Room Width: 11.0
Room 6
  • Room Entry Order: 3
  • Room Length: 11.0
  • Room Type: Bedroom
  • Room Width: 11.0
Room 7
  • Room Entry Order: 4
  • Room Features: Formal
  • Room Length: 14.0
  • Room Type: Dining Room
  • Room Width: 13.0
Room 8
  • Room Entry Order: 4
  • Room Features: Formal
  • Room Length: 14.0
  • Room Type: Dining Room
  • Room Width: 13.0
Room 9
  • Listing Key: DD555B96083D87C8E0531401100A4EB2
  • Room Entry Order: 6
  • Room Features: Country
  • Room Length: 29.0
  • Room Type: Kitchen
  • Room Width: 13.0
Room 10
  • Room Entry Order: 6
  • Room Features: Country
  • Room Length: 29.0
  • Room Type: Kitchen
  • Room Width: 13.0
Room 11
  • Room Entry Order: 7
  • Room Features: Fireplace
  • Room Length: 16.0
  • Room Type: Living Room
  • Room Width: 13.0
Room 12
  • Room Entry Order: 7
  • Room Features: Fireplace
  • Room Length: 16.0
  • Room Type: Living Room
  • Room Width: 13.0
Room 13
  • Room Entry Order: 8
  • Room Features: Ceiling Fan,Walk-In Closet,Whirlpool Tub
  • Room Length: 17.0
  • Room Type: Primary Bedroom
  • Room Width: 14.0
Room 14
  • Room Entry Order: 8
  • Room Features: Ceiling Fan,Walk-In Closet,Whirlpool Tub
  • Room Length: 17.0
  • Room Type: Primary Bedroom
  • Room Width: 14.0
Property
Property and Assessments
  • Color: Grey
  • Driveway Type: Gravel
  • Exterior Siding: Vinyl Siding
  • Fuel Tank Location: Above Ground
  • Sq Ft Source: Public Records
  • Year Built: 1999
  • Bank Owned Property: No
Lot Information
  • Lot Description: Lightly Wooded, Secluded, Professionally Landscaped
  • Parcel Number: 941054
  • Sq Ft Total: 2264.0
Utilities
  • Energy Features: Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well

Property History for 86 Winthrop Road

DateEvent & SourcePriceAppreciation
Jul 31, 2009

Closed (Public Record)

Public Record #273922535

$383,000

+3.5% / yr

Sep 28, 1999

Closed (Public Record)

Public Record #91990716

$273,500
DateEvent & SourcePrice
07/31/2009

Closed (Public Record)

Public Record #273922535

$383,000

+3.5% / yr

09/28/1999

Closed (Public Record)

Public Record #91990716

$273,500

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 86 Winthrop Road

Taxable ValueLand$62,930Additions$297,990Total$360,920
Tax Record2025$9,774 ($814 / month)
Home Facts
Beds4Baths2.5Total Finished SqFt2,494 SqFtAbove Grade Finished SqFt2,494 SqFtUnfinished Basement SqFt920 SqFtStories2Lot Size112,385 SqFtStyleSingle Family ResidenceYear Built1999Year Renovated2007ZoningR-2CountyLOWER CONNECTICUT RIVERAPNCSTR M:17 B:115

Schools near 86 Winthrop Road

This home is within Regional School District 04.
Rating
School
Type
Grades
Distance
Public - PK to 6
Public - 7 to 8
Public - 9 to 12
Rating
School
Distance
Chester Elementary School
PublicPK to 6

John Winthrop Middle School
Public7 to 8

Valley Regional High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

New listings in 06412

$439,900 | 43 Goose Hill Road, Chester, CT 06412
1/39
Coming Soon

$439,900

3
Bedrooms
1,742
Square Feet
1.9
Acres
$1,900,000 | 47 East Kings Highway, Chester, CT 06412
1/40
Virtual Tour

$1,900,000

4
Bedrooms
3,957
Square Feet
3.2
Acres
$499,000 | 88 Winthrop Road, Chester, CT 06412
1/24

$499,000

3
Bedrooms
2,240
Square Feet
33.97
Acres
$824,900 | 275 West Main Street, Chester, CT 06412
1/39

$824,900

4
Bedrooms
2,706
Square Feet
2
Acres
$465,000 | 6 Castle View Drive, Chester, CT 06412
1/32

$465,000

3
Bedrooms
2,031
Square Feet
0.43
Acres
$1,350,000 | 19 Denlar Drive, Chester, CT 06412
1/40
Listed By Coldwell Banker Realty

$1,350,000

2
Bedrooms
5,886
Square Feet
0.66
Acres
$764,900 | 13 High Field Lane, Chester, CT 06412
1/40
Coming SoonOpen: 9/19 11:00AM - 02:00PM

$764,900

4
Bedrooms
2,662
Square Feet
2.24
Acres
front view of a house with a yard
1/39
Under Contract - Continue To Show

$599,900

2
Bedrooms
2,000
Square Feet
$499,900 | 55 Wig Hill Road, Chester, CT 06412
1/38

$499,900

3
Bedrooms
1,774
Square Feet
1.43
Acres

Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 86 Winthrop Road, Chester, CT 06412
$383,000
4
2,264
112,384
$275,000
3
1,456
101,494
4
3.5
2,583
224,334
4
2
2,791
261,360
$267,500
4
3
3,734
199,940
4
2
1,737
1,279,793

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Century 21 Heritage Company, Hope Matthies-Rayner

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.