Welcome to one of Wellesleys most coveted neighborhoods! This meticulously maintained central entrance colonial is within walking distance to Bates School, Boulder Brook Reservation and Fells Market. Sunny floor through updated kitchen/ dining space w window seat. The bright large fireplaced living room sits adjacent to the sunroom overlooking a outdoor patio and large level fenced in yard. The master bedroom offers his and her closets. Two additional bedrooms and a shared bath complete the upper level. This home offers plenty of room for storage in the easily accessible walk up attic. The partially finished lower level could be used as home office, playroom or exercise room. Expansion possibilities. Move right in!
- MLS# 72738800
- Date Listed10/07/2020
- Bedrooms 3
- Bathrooms 1 Full baths, 1 Half baths
- Lot Size 0.3 acres (13,068 sq. ft)
- Sewer Public Sewer
- Property Type Single Family
- County Norfolk
- Year Built 1951
- Water Public
- Square Feet 1,440 sq. ft
- Price Per Sq. Ft $763.89
Interior Features
- Appliances Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
- Cooling None
- Heating Baseboard
Exterior / Lot Features
- Roof Shingle
- Lot Size Acres 0.30
- Lot Size SQFT 13,068.00
- Lot Features Wooded
Directions
Take Weston Road to Boulder Brook Rd, left on Chesterton and destination is 200ft on the left
Financial Considerations
- Tax Amount $10,323
- Terms Cash, Conventional, FHA, VA Loan
Nearby Schools
Source: School Digger
Preschool At Wellesley Schools
Public • PK - PK • Serves this home
4.88 mi
Distance
Public • 6 - 8 • Serves this home
2.34 mi
Distance
Public • 9 - 12 • Serves this home
2.97 mi
Distance
Public • PK - 3
4.79 mi
Distance
Preschool At Wellesley Schools
Public • PK - PK • Serves this home
4.88 mi
Distance
Public • PK - 3
5.02 mi
Distance
Public • PK - PK
5.69 mi
Distance
Public • PK - 5
5.92 mi
Distance
Blocks Pre School @ Juniper Hill
Public • PK - PK
7 mi
Distance
William F. Stanley Elementary School
Public • PK - 5
7.45 mi
Distance
Public • PK - 5
7.54 mi
Distance
Public • PK - 5
9.64 mi
Distance
Public • 6 - 8 • Serves this home
2.34 mi
Distance
Public • 6 - 8
2.67 mi
Distance
Public • 5 - 8
3.56 mi
Distance
Public • 6 - 8
3.67 mi
Distance
Public • 4 - 5
4.79 mi
Distance
Christa Mcauliffe Charter School
Public • 6 - 8
5.52 mi
Distance
Public • 5 - 8
6 mi
Distance
Public • 6 - 8
6.46 mi
Distance
Public • 6 - 6
7.11 mi
Distance
Public • 7 - 8
7.19 mi
Distance
Public • 9 - 12
2.67 mi
Distance
Public • 9 - 12 • Serves this home
2.97 mi
Distance
Public • 9 - 12
4.71 mi
Distance
Public • 9 - 12
4.81 mi
Distance
Public • 9 - 12
6.28 mi
Distance
Public • 9 - 12
6.77 mi
Distance
Private • 06 - 12
0.64 mi
Distance
Private • 08 - 12
1.4 mi
Distance
Brandon School & Residental Treatment
Private • 02 - 12
1.91 mi
Distance
Private • 05 - 12
3.04 mi
Distance
Walnut Hill School For The Arts
Private • 09 - 12
3.48 mi
Distance
Private • UG - UG
4.76 mi
Distance
Private • KG - UG
5.68 mi
Distance
Private • 03 - 12
6.23 mi
Distance
Private • 08 - 11
7.22 mi
Distance
Private • UG - UG
7.32 mi
Distance
Sales & Tax History
Source: Public Records
| Street Address | Beds | Baths | Sold Date | List Price | Valuation Date | Valuation Price |
|---|---|---|---|---|---|---|
| 313 North Main Street | Listing | 2 | 2 | Dec 18, 2025 | $525,000 | Feb 23, 2024 | $448,038 |
| 58 Norwich Road | Listing | 4 | 4 | Jan 16, 2026 | $2,249,000 | Mar 21, 2024 | $2,012,445 |
| 26 Winter Street | Listing | 4 | 3 | Dec 22, 2025 | $1,088,000 | Feb 23, 2024 | $1,027,081 |
| 36 Oakridge Rd | 6 | 7 | Dec 06, 2025 | $4,999,000 | Feb 05, 2026 | - |
| 5 Oakridge Ave. | 5 | 4 | Jan 31, 2026 | $1,849,999 | Feb 05, 2026 | - |
| 48 Shady Hill Road | 4 | 5 | Dec 10, 2025 | $1,595,000 | Feb 05, 2026 | - |
| 45 Mayo Rd | 3 | 2 | Jan 11, 2026 | $1,300,000 | Feb 05, 2026 | - |
| 19 Harwood Road | 5 | 4 | Dec 13, 2025 | $1,948,000 | Feb 05, 2026 | - |
| 1 Winter St. | 4 | 5 | Jan 31, 2026 | $1,535,000 | Feb 05, 2026 | - |
| 4 Richard Rd | 3 | 2 | Dec 31, 2025 | $785,000 | Feb 05, 2026 | - |
Population & Environment
Source: Sperling's Best Places
| Zip | City | County | National | |
|---|---|---|---|---|
| Population | N/A | 14,421 | 725,326 | 335,858,263 |
| Population Density | N/A | 2,879 | 1,831 | 95 |
| People per Household | N/A | 2.8 | 2.5 | 2.6 |
| Median Age | N/A | 33.9 | 43 | 39.1 |
| Median Income | N/A | $182,173 | $108,049 | $66,222 |
| Average Income | N/A | $96,489 | $57,162 | $35,475 |
| Cost of Living Index | 146 | 139 | 117 | 100 |
| Zip | City | County | National | |
|---|---|---|---|---|
| January Avg. High Temp | N/A°F | 17.29°F | 18.1°F | 22.6°F |
| July Avg. High Temp | N/A°F | 83.13°F | 81.2°F | 86.2°F |
| Annual Precipitation | N/A" | 45.45" | 51.22" | 38" |
36/100
Car-Dependent
Walk Score ®
46/100
Bikable
Bike Score ®
Overview
Most errands require a car. It is possible to get on a bus. Minimal bike infrastructure.Walkability averages in the surrounding area
The average walkability score in the surrounding area is Walk Score: 21/100, Transit Score: 0/100, Bike Score: 27/100.
Property Change History
Points of Interest near 20 Chesterton Rd, Wellesley, MA 02481
0.29 mi
Distance
0.29 mi
Distance
0.41 mi
Distance
0.42 mi
Distance
Ferrelli Field, Weston, MA, USA
Recreation • Entertainment
0.43 mi
Distance
0.49 mi
Distance
0.54 mi
Distance
0.54 mi
Distance
0.31 mi
Distance
0.4 mi
Distance
Ferrelli Field, Weston, MA, USA
Recreation • Entertainment
0.43 mi
Distance
0.3 mi
Distance
0.48 mi
Distance
0.54 mi
Distance
0.2 mi
Distance
0.31 mi
Distance
0.33 mi
Distance
0.34 mi
Distance
0.38 mi
Distance
0.41 mi
Distance
0.46 mi
Distance
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Frequently Asked Questions for 20 Chesterton Rd
Source: Realty.com
20 Chesterton Rd, Wellesley, MA 02481 is a Single Family 1,440 sq. ft. home listed for sale. Realty.com has 31 photos available of this 3 bed, 2 bath house, listed at $1,100,000. View sales and tax history, use our mortgage calculator and more on Realty.com
Realty.com has 31 photos of 20 Chesterton Rd.
Our records indicate that 20 Chesterton Rd was built in 1951.
The full address for this home is 20 Chesterton Rd, Wellesley, MA 02481.
20 Chesterton Rd has been listed on Realty.com since Wed October 07, 2020
Most errands require a car. It is possible to get on a bus. Minimal bike infrastructure.
The average walkability score in the surrounding area is Walk Score: 21/100, Transit Score: 0/100, Bike Score: 27/100.
There are 3 schools assigned to this home. Check out the schools near 20 Chesterton Rd. Preschool At Wellesley Schools (Grades: PK - PK), Wellesley Middle School (Grades: 6 - 8), Wellesley Senior High School (Grades: 9 - 12)
Listing provided courtesy of:
Peabody Properties, Inc.
(tel: 781-794-1000)
Listing agent:
Karen Muse
(#BB815215)
This content last refreshed on 2026-02-05 11:56:02. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Export listing data of 20 Chesterton Rd, Wellesley, MA 02481 : MLS# 72738800