53 Chesterton Rd

5,779 Sq. Ft.
$558 / Sq. Ft.
5,779
Sq. Ft.
$558
per Sq. Ft.

Description

Located in one of Wellesley's most admired neighborhoods, this exceptional home offers four full floors of beautifully designed living space. The layout provides flexibility for family, guests, and everyday comfort. The fabulous custom kitchen features Dodd Woodworking cabinets, high end appliances, oversized island, dining area & opens to family room with built-ins & gas fireplace. The exquisite primary offers spas like bath with soaking tub, radiant floors & custom walk-in closet. Three additional...Located in one of Wellesley's most admired neighborhoods, this exceptional home offers four full floors of beautifully designed living space. The layout provides flexibility for family, guests, and everyday comfort. The fabulous custom kitchen features Dodd Woodworking cabinets, high end appliances, oversized island, dining area & opens to family room with built-ins & gas fireplace. The exquisite primary offers spas like bath with soaking tub, radiant floors & custom walk-in closet. Three additional bedrooms & two baths complete the second floor. Amazing third floor with bedroom/bonus room, office & full bath is perfect for today's needs. The finished lower level expands the living area, ideal for recreation with mudroom, gym, media space & bathroom, while maintaining the home’s polished feel. Each level flows seamlessly, offering both open gathering areas and quiet retreats. Set in a coveted setting known for its charm & community, close to Boulder Brook reservation & Bates school.

Listing Agent

  1. Lara O'Rourke

    Lara O'Rourke

    Listing Agent

    Coldwell Banker Realty - Wellesley

    P: (781)-237-9090

Property Details for 53 Chesterton Road

Town
Wellesley
Area
MA-Wellesley
Architectural Style
Colonial
Style
Colonial
Garage Spaces
2
Open Parking Spaces
4.00
Parking Spaces Total
6
LISTING CLOSED: 06/01/2026 12:00 AM

Property Details for 53 Chesterton Road

StatusSold
MLS #73482542
Days on Market5
Taxes$23,350 / year
HOA Fees-
Property TypeSingle Family
MLS TypeSingle Family / Detached
Year Built2008
CountyNorfolk County

Location

Sold By Columbus and Over Group, LLC, Jonathan Russell

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Building Information for 53 Chesterton Road

Stories-Year Built2008Building Size-Lot Size0.24 AC / 10,462 SF

Payment Calculator

$18,016 per month

30 year fixed, 6.36% Interest

Principal and Interest

$16,071

Property Taxes

$1,946

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 53 Chesterton Road

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Shopping, Tennis Court, Park, Walk/Jog Trails, Bike Path, Conservation Area, Public School
  • Current Financing: Withheld
  • Living Area: 5779.0
  • Color: Beige
  • SqFt with Basement: Yes
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Water View: No
  • Year Built Details: Actual
  • Year Built Source: Public Records
Location/School
  • Grade School: Bates
  • High School: Whs
  • Middle School: Wms
  • Neighborhood: Bates
Features
Interior Features
  • Appliances: Range, Dishwasher, Refrigerator
  • Basement Features: Full, Partially Finished, Sump Pump
  • Num of Baths: 6.0
  • Num of Full Baths: 5
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 5.50
  • Bathrooms Total Integer: 6
  • DoorFeatures: Insulated Doors
  • FireplaceFeatures: Living Room, Master Bedroom
  • FireplaceYN: Yes
  • Fireplaces: 3
  • Flooring: Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet, Flooring - Hardwood
  • Interior Features: Closet, Wet bar, Play Room, Bonus Room, Office
  • Interior Features: Security System
  • Laundry Features: Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile, Second Floor, Washer Hookup
  • Primary Bath: Yes
  • SpaYN: No
  • Window Features: Skylight, Insulated Windows
Exterior Features
  • Construction: Frame
  • Exterior Features: Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Fenced Yard
  • Exterior Features: Fenced Yard, Professional Landscaping, Sprinkler System, Patio
  • Fencing: Fenced/Enclosed, Fenced
  • Lot Description: Level
  • Patio And Porch Features: Patio
  • Roof Material: Shingle
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 2.00
  • Garage: Yes
  • Garage Parking: Attached, Garage Door Opener, Heated, Paved Drive, Off-Street, Paved Driveway
  • Open Parking: Yes
  • Parking Features: Attached, Garage Door Opener, Heated, Paved Drive, Off-Street, Paved Driveway
  • Parking Features: Heated, Off-Street, Paved Driveway
Utilities
  • Cooling: Central Air
  • Cooling: Yes
  • Heating: Forced Air, Natural Gas
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Gas Range, Washer Hookup
  • Water: Public
Room Information
Primary Bedroom
  • Room Primary Bedroom Area: 252.0
  • Room Primary Bedroom Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Walk-In Closet(s),Closet,Flooring - Hardwood,Recessed Lighting,Half Vaulted Ceiling(s)
  • Room Primary Bedroom Length: 18.0
  • Primary Bedroom Level: Second Floor
  • Room Primary Bedroom Width: 14.0
Bedroom 2
  • Bedroom2 Area: 234.0
  • Bedroom2 Features: Bathroom - Full,Closet,Flooring - Hardwood,Flooring - Stone/Ceramic Tile
  • Bedroom2 Length: 13.0
  • Bedroom2 Level: Second
  • Bedroom2 Width: 18.0
Bedroom 3
  • Bedroom3 Area: 256.0
  • Bedroom3 Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Closet,Flooring - Hardwood
  • Bedroom3 Length: 16.0
  • Bedroom3 Level: Second
  • Bedroom3 Width: 16.0
Bedroom 4
  • Bedroom4 Area: 240.0
  • Bedroom4 Features: Closet,Flooring - Hardwood
  • Bedroom4 Length: 16.0
  • Bedroom4 Level: Second
  • Bedroom4 Width: 15.0
Bedroom 5
  • Bedroom5 Area: 644.0
  • Bedroom5 Features: Closet,Flooring - Wall to Wall Carpet
  • Bedroom5 Length: 23.0
  • Bedroom5 Level: Third
  • Bedroom5 Width: 28.0
Bathroom 1
  • Bathroom1 Features: Bathroom - Half,Flooring - Stone/Ceramic Tile
  • Bathroom1 Level: First
Bathroom 2
  • Bathroom2 Features: Bathroom - Full,Bathroom - With Shower Stall,Flooring - Stone/Ceramic Tile
  • Bathroom2 Level: Basement
Bathroom 3
  • Bathroom3 Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile
  • Bathroom3 Level: Third
Dining Room
  • Dining Room Area: 247.0
  • Dining Room Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Chair Rail,Wainscoting,Crown Molding
  • Dining Room Length: 13.0
  • Dining Room Level: Main,First
  • Dining Room Width: 19.0
Family Room
  • Family Room Area: 324.0
  • Family Room Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Open Floorplan,Recessed Lighting
  • Family Room Length: 18.0
  • Family Room Level: Main,First
  • Family Room Width: 18.0
Kitchen
  • Kitchen Area: 210.0
  • Kitchen Features: Flooring - Hardwood,Dining Area,Kitchen Island,Exterior Access,Open Floorplan,Recessed Lighting,Second Dishwasher
  • Kitchen Length: 15.0
  • Kitchen Level: Main,First
  • Kitchen Width: 14.0
Living Room
  • Room Living Room Area: 208.0
  • Room Living Room Features: Flooring - Hardwood,Window(s) - Picture,Crown Molding
  • Room Living Room Length: 13.0
  • Room Living Room Level: Main,First
  • Room Living Room Width: 16.0
Other Room 1
  • Room Office Area: 126.0
  • Room Office Features: Skylight,Flooring - Hardwood
  • Room Office Length: 7.0
  • Room Office Level: Third
  • Room Office Width: 18.0
Property Information
Property Info
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Frontage Type: Public
  • Road Responsibility: Public Maintained Road
  • Road Surface Type: Paved
Tax Information
  • Tax ID: M:179 R:053 S:,264243
  • Assessments: $2,296,000
  • Book: 25796
  • Tax Year: 2026
  • Zoning: SR10
Building / Association Information
Living Characteristics
  • Beds Total: 5
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Cooling Zones: 3
  • Heat Zones: 4
Complex & Association Information
  • Association Security: Security System
  • Adult Community: No

Property History for 53 Chesterton Road

DateEvent & SourcePriceAppreciation
Jun 1, 2026

Sold

MLS PIN #73482542

$3,225,000
Mar 9, 2026

Under Agreement

MLS PIN #73482542

Mar 9, 2026

Contingent

MLS PIN #73482542

DateEvent & SourcePrice
06/01/2026

Sold

MLS PIN #73482542

$3,225,000
03/09/2026

Under Agreement

MLS PIN #73482542

03/09/2026

Contingent

MLS PIN #73482542

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

Public Records for 53 Chesterton Road

Taxable ValueLand$1,043,000Additions$1,201,000Total$2,244,000
Tax Record2025$23,068 ($1,922 / month)
Home Facts
Beds5Baths5.5Total Finished SqFt4,368 SqFtAbove Grade Finished SqFt4,368 SqFtStories2Lot Size10,462 SqFtStyleSingle Family ResidenceYear Built2008ZoningSR10CountyNORFOLKAPNWELL M:179 R:053 S:Fireplace TypeHas Fireplace

Schools near 53 Chesterton Road

This home is within Wellesley School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Private - 6 to 12
Rating
School
Distance
Katharine Lee Bates Elementary School
PublicK to 5

Wellesley Middle School
Public6 to 8

Wellesley High School
Public9 to 12

The Rivers School
Private6 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.

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The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.