Sold
Last Sold Price
4 beds3,200 sqft
153 Chapel Rd, Winchester, CT 06098
Single FamilyProperty Type
1.04 acresLot Size
1785Year Built
$141/sq ftPrice per sq ft
2 carsParking Spaces

Description

Authentic early american home in rare, pristine condition. Warm by the fireplaces of this trophy home with gorgeous kitchen, master, formal,informal rooms. Meticulous restoration. Red barn, gardens, views. One of a kind setting. C/air,propane gener,more.Authentic early american home in rare, pristine condition. Warm by the fireplaces of this trophy home with gorgeous kitchen, master, formal,informal rooms. Meticulous restoration. Red barn, gardens, views. One of a kind setting. C/air,propane gener,more.
  • Listed by: Dan Tolman 860.738.1900 • New England Real Estate Compan
Listing closed: 04/15/2009 12:00 AM • Source: SMARTMLS, MLS#: L129165

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Recent comparable sales

Median sold price

$433,000

Avg days on market

58

Sale-to-list ratio

92.2%

Winchester, CT

9 comparable properties found

$440,000 | 440 Platt Hill Road, Winchester, CT 06098
1

$440,000

Sold 02/06/26

4
Bedrooms
3,416
Square Feet
9.6
Acres
$475,000 | 5 Stadler Heights, Winchester, CT 06098
2

$475,000

Sold 07/10/26

4
Bedrooms
3,556
Square Feet
3.19
Acres
$480,000 | 5515 Van Meter Road, Winchester, KY 40391
1/58
3

$480,000

Sold 02/09/26

4
Bedrooms
2,940
Square Feet
5
Acres
$428,000 | 17 Hampton Avenue, Winchester, KY 40391
1/47
4

$428,000

Sold 09/04/25

4
Bedrooms
3,181
Square Feet
0.34
Acres
$487,500 | 1317 Caroline Street, Winchester, VA 22601
1/65
5

$487,500

Sold 07/29/26

4
Bedrooms
2,837
Square Feet
0.41
Acres
$433,000 | 118 S Road, Winchester, CT 06098
6

$433,000

Sold 05/29/26

4
Bedrooms
2,240
Square Feet
2.76
Acres
$425,000 | 50 Lakeview Road, Winchester, CT 06098
7

$425,000

Sold 08/13/25

4
Bedrooms
2,086
Square Feet
0.63
Acres
$420,000 | 354 Platt Hill Road, Winchester, CT 06098
8

$420,000

Sold 11/22/24

4
Bedrooms
2,486
Square Feet
1.5
Acres
$375,000 | 117 S Road, Winchester, CT 06098
9

$375,000

Sold 02/05/26

3
Bedrooms
2,747
Square Feet
3.37
Acres

Location

Listing Courtesy of New England Real Estate Compan, Dan Tolman
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$3,018 per month

30 year fixed, 7.03% Interest

Principal and Interest

$2,402

Property Taxes

$615

HOA Dues

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Property Information for 153 Chapel Road

Property Details
  • Taxes: $7,382 / year
  • MLS Type: Residential
  • Basement Description: Full, Unfinished
  • Direct Waterfront: No
  • Garages Number: 2
  • Style: Colonial
  • Garage Parking Info: Barn
  • Swimming Pool: No
Building Information
  • Year Built: 1785
  • Lot Size: 1.04 AC / 45,302 SF
Summary
Property and Location
  • Association Amenities: Private Rec Facilities
  • Directions: Route 263 to winchester center. Or newfield road to winchester center. Sign posted.
  • Elementary School: Batchell
  • High School: Gilbert
  • Intermediate School: Pearson
  • Latitude: 41.901993
  • Longitude: -73.12537
  • Neighborhood Amenities: Private Rec Facilities, Private School(s)
  • State: Connecticut
HOA and Fees
  • Property Tax: $7,382
Interior and Exterior Features
Exterior Features
  • Exterior Features: Barn, Garden Area, Stone Wall
Interior Features
  • Appliances Included: Dishwasher, Oven/Range, Refrigerator
  • Attic Description: Storage Space, Walk-up
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Cable - Available, Security System
  • Laundry Room Location: First Floor
  • Room Count: 9
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Length: 13.0
  • Room Type: Bedroom
  • Room Width: 12.0
Room 2
  • Room Entry Order: 1
  • Room Length: 13.0
  • Room Type: Bedroom
  • Room Width: 12.0
Room 3
  • Room Entry Order: 12
  • Room Type: Other
Room 4
  • Room Entry Order: 12
  • Room Type: Other
Room 5
  • Room Entry Order: 2
  • Room Length: 14.0
  • Room Type: Bedroom
  • Room Width: 8.0
Room 6
  • Room Entry Order: 2
  • Room Length: 14.0
  • Room Type: Bedroom
  • Room Width: 8.0
Room 7
  • Room Entry Order: 3
  • Room Length: 17.0
  • Room Type: Bedroom
  • Room Width: 29.0
Room 8
  • Room Entry Order: 3
  • Room Length: 17.0
  • Room Type: Bedroom
  • Room Width: 29.0
Room 9
  • Room Entry Order: 4
  • Room Features: Formal
  • Room Length: 15.0
  • Room Type: Dining Room
  • Room Width: 12.0
Room 10
  • Room Entry Order: 4
  • Room Features: Formal
  • Room Length: 15.0
  • Room Type: Dining Room
  • Room Width: 12.0
Room 11
  • Room Entry Order: 5
  • Room Features: Book Shelves,Fireplace
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 14.0
Room 12
  • Room Entry Order: 5
  • Room Features: Book Shelves,Fireplace
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 14.0
Room 13
  • Room Entry Order: 6
  • Room Features: Country,Pantry
  • Room Length: 18.0
  • Room Type: Kitchen
  • Room Width: 13.0
Room 14
  • Room Entry Order: 6
  • Room Features: Country,Pantry
  • Room Length: 18.0
  • Room Type: Kitchen
  • Room Width: 13.0
Room 15
  • Room Entry Order: 7
  • Room Features: Fireplace,Formal
  • Room Length: 15.0
  • Room Type: Living Room
  • Room Width: 22.0
Room 16
  • Room Entry Order: 7
  • Room Features: Fireplace,Formal
  • Room Length: 15.0
  • Room Type: Living Room
  • Room Width: 22.0
Room 17
  • Room Entry Order: 8
  • Room Length: 24.0
  • Room Type: Primary Bedroom
  • Room Width: 13.0
Room 18
  • Room Entry Order: 8
  • Room Length: 24.0
  • Room Type: Primary Bedroom
  • Room Width: 13.0
Property
Property and Assessments
  • Color: Beige
  • Driveway Type: Asphalt
  • Exterior Siding: Clapboard
  • Fuel Tank Location: Above Ground
  • Sq Ft Source: Owner
  • Year Built: 1785
Lot Information
  • Lot Description: Professionally Landscaped
  • Parcel Number: 925368
  • Sq Ft Total: 3200.0
Utilities
  • Energy Features: Generator
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil
  • Sewage System: Septic
  • Water Source: Private Well

Property History for 153 Chapel Road

DateEvent & SourcePriceAppreciation
Apr 15, 2009

Closed (Public Record)

Public Record #267859976

$447,000

-3.6% / yr

Aug 17, 2007

Closed (Public Record)

Public Record #226240654

$475,000

+2.3% / yr

Oct 2, 2002

Closed (Public Record)

Public Record #106454039

$425,000

+74.2% / yr

DateEvent & SourcePrice
04/15/2009

Closed (Public Record)

Public Record #267859976

$447,000

-3.6% / yr

08/17/2007

Closed (Public Record)

Public Record #226240654

$475,000

+2.3% / yr

10/02/2002

Closed (Public Record)

Public Record #106454039

$425,000

+74.2% / yr

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

Public Records for 153 Chapel Road

Taxable ValueLand$51,520Additions$418,950Total$470,470
Tax Record2025$13,724 ($1,144 / month)
Home Facts
Beds3Baths2Total Finished SqFt2,629 SqFtAbove Grade Finished SqFt2,629 SqFtUnfinished Basement SqFt836 SqFtStories2Lot Size45,302 SqFtStyleSingle Family ResidenceYear Built1785Year Renovated1785ZoningRU-3CountyNORTHWEST HILLSAPNWSTR M:036 B:154 L:041

Schools near 153 Chapel Road

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Public - 2 to 6
Public - 1 to 4
Public - PK to 2
Rating
School
Distance
Pearson Middle School
Public2 to 6

Able School
Public1 to 4

Mary P. Hinsdale School
PublicPK to 2

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.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 153 Chapel Road, Winchester, CT 06098
$450,000
4
3,200
45,302
–
–
–
–
–
$60,000
–
–
–
235,224
–
–
–
744
2,178
–
3
2.5
2,552
43,560
–
–
–
2,707
10,890

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 New England Real Estate Compan, Dan Tolman

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.