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
Schools near 02481
Explore the local neighborhood highlights and top-rated schools near 02481 in Wellesley, MA.
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 |
|---|---|---|---|---|
| 8 Liberty Street | 5 | 6 | May 20, 2026 | $1,998,000 |
| 7 Westwood Rd | 3 | 2 | Jun 02, 2026 | $699,900 |
| 84 Royalston Rd | 6 | 6 | Jun 09, 2026 | $3,874,000 |
| 79 Walnut Rd | 5 | 7 | Jun 28, 2026 | $6,495,000 |
| 23 Pilgrim Rd | 4 | 4 | May 13, 2026 | $2,745,000 |
| 99 Old Colony Road | 6 | 7 | May 16, 2026 | $5,294,500 |
| 48 Patton Road | 5 | 4 | Jun 03, 2026 | $2,295,000 |
| 138 Lowell Road | 5 | 6 | May 16, 2026 | $3,795,000 |
| 22 Cranmore Rd | 5 | 5 | Jun 24, 2026 | $3,495,000 |
| 53 Chesterton Road | 5 | 6 | Jun 03, 2026 | $3,295,000 |
Local Neighborhood Highlights for 02481
Discover key demographics, population statistics, and environmental insights for the Wellesley, MA area.
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" |
35/100
Car-Dependent
Walk Score ®
0/100
Minimal Transit
Transit 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
0.43 mi
Distance
0.49 mi
Distance
0.54 mi
Distance
0.54 mi
Distance
0.31 mi
Distance
0.4 mi
Distance
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
Nearby Properties
-
$1,160,000 Active4 bds • 2 ba • 1,400 sqft
2 Marigold Ave, Wellesley, MA 02482
Top condition 4 bed room, single family, 1.5 bath on the corner of a cul-de- sac. Great location with easy access to Routes 9, 16 & 30. Updated kitchen and baths. Insulated windows Finished basement with large laundry/storage room.Listing by: -
$1,088,000 Active Under Contract3 bds • 2 ba • 1,521 sqft
6 Oakland Circle, Wellesley, MA 02481
Nestled on a quiet side street in Wellesley, this charming residence offers the perfect blend of timeless elegance, comfort, and convenience. A great opportunity to enjoy one of Greater Boston's most desirable communities at an attractive price point...Listing by: -
$1,035,000 Active3 bds • 2 ba • 1,656 sqft
678 Boston Post Road, Weston, MA 02493
Welcome home to 678 Boston Post Road... A sun-splashed, historic village colonial that seamlessly blends its charm with a sought after suburban community with many urban amenities. The open floor plan invites you in with a living room and adjoining d...Listing by: -
$1,050,000 Active3 bds • 2 ba • 1,607 sqft
1360 Great Plain Ave, Needham, MA 02492
Tastefully renovated 3-bedroom, 2-bath single-family home offers the perfect blend of comfort, privacy & accessibility. Set back off the street & overlooking a serene pond, the property delivers picturesque water views & a peaceful setting rarely fou...Listing by: -
$1,250,000 Active3 bds • 2 ba • 1,538 sqft
178 Webster St, Needham, MA 02494
First time available on the open market! Nestled in the highly desirable Needham Heights, this cherished 3-bedroom, 2-bath ranch has been lovingly maintained by the same family for over 70 years! The updated kitchen flows seamlessly into the open-con...Listing by: -
$1,189,000 Active3 bds • 3 ba • 1,610 sqft
267 River Street 267, Newton, MA 02465
Owner Financing is available at 5% for 2 years. Exceptional new construction first floor unit in West Newton with 3 bedrooms, 2.5 baths of refined living space. Designed with a modern aesthetic and built with impressive attention to detail, this home...Listing by: -
$950,000 Active3 bds • 3 ba • 1,625 sqft
81 Brook Rd 81, Weston, MA 02493
Rare opportunity in Weston’s sought-after Brook Road neighborhood! This charming three-story home offers 3 bedrooms, 2.5 baths, and updated living space that blends timeless character with modern convenience. Features include a welcoming front porch,...Listing by: -
$950,000 Active3 bds • 3 ba • 1,625 sqft
81 Brook Rd, Weston, MA 02493
Rare opportunity in Weston’s sought-after Brook Road neighborhood! This charming three-story home offers 3 bedrooms, 2.5 baths, and updated living space that blends timeless character with modern convenience. Features include a welcoming front porch,...Listing by: -
$1,150,000 Active3 bds • 2 ba • 1,570 sqft
47 Cherry St, Newton, MA 02465
OPEN HOUSE Sunday 7/12/26: 12:00pm-2:00pm. Welcome to 47 Cherry Street. Updated & move in ready, this 3 Bedroom 1 1/2 bath brick exterior home with a 1 Car Garage is located in West Newton. First floor features a living room with fireplace, den, dini...Listing by: -
$1,050,000 Active3 bds • 2 ba • 1,596 sqft
22 Harrington St 2, Newton, MA 02460
Stunning, sun filled 3 bedroom home on 2 levels. Gorgeous eat-in kitchen, a private office overlooks the enormous fenced in yard, off street parking tandem parking for 3 vehicles, and 5 mini split ac/heat in each bedroom, kitchen and livingroom, all...Listing by: -
$979,000 Active2 bds • 2 ba • 1,350 sqft
321 Hammond Pond Pkwy 103, Brookline, MA 02467
1,350 SF single-level condo in a 2012 low-rise building (27 units total) in Chestnut Hill, Brookline. Features an open-concept living/dining footprint with hardwood floors, new recessed lighting, and private balcony. Gourmet kitchen features granite...Listing by: -
$945,000 Active2 bds • 2 ba • 1,440 sqft
13-15 Gay Street, Westwood, MA 02090
Rare opportunity to own a two family duplex style home in Westwood center. Ideal for owner occupant or investor. Potential to expand or condo conversion pending town approvals. One unit currently rented and the other side is now vacant. The yard is s...Listing by: -
$1,180,000 Active Under Contract3 bds • 4 ba • 1,650 sqft
48 Beacon Park, Watertown, MA 02472
Beautifully renovated and thoughtfully updated, this Watertown single-family home is tucked away on a quiet, tree-lined street just moments from vibrant Watertown Square. From the moment you enter, the home welcomes you with timeless character and wa...Listing by: -
$1,250,000 Active2 bds • 3 ba • 1,600 sqft
456 Belmont Street #10, Watertown, MA 02472
Payson Estate. Top-floor 2 bedroom, 2.5 bathroom condominium with panoramic Boston skyline views in Elevator-Building. Professionally-designed and gut-renovated, this corner unit merges Tudor Architecture with a modern minimalist interior. Brigh...Listing by: -
$999,000 Active3 bds • 2 ba • 1,240 sqft
1896 Beacon St 3, Brookline, MA 02445
New price! Offering both classic charm and detail with a modern touch, this spacious 3 bedroom 2 bathroom home has everything on your wish list. The living room features classic built-ins, bowed windows and a cozy fireplace. Directly off of the livi...Listing by: -
$1,250,000 Active3 bds • 3 ba • 1,494 sqft
27 Shepard St 4, Boston, MA 02135
Newly constructed and thoughtfully designed, this 3-bed, 3-bath residence at 27 Shepard Street offers the space and finishes growing families rarely find in the city. The open-concept living, dining, and kitchen area features professional-grade appli...Listing by: -
$1,220,000 Active3 bds • 2 ba • 1,264 sqft
1650 Commonwealth Ave 505, Boston, MA 02135
Brighton's premier 2018-built luxury condo building on iconic Commonwealth Avenue. This rare 3 bedroom 2 bath unit has full tandem 2 car covered parking. Amazing treetop view from private balcony. The gourmet kitchen has high end Wolf gas stove and...Listing by: -
$1,199,000 Active2 bds • 2 ba • 1,226 sqft
1 Nevins Hill Way 509, Boston, MA 02135
Set within Nevins Hill, one of Brighton’s newest boutique condominium communities, this beautifully maintained 2-bedroom, 2-bath residence with a den/office offers a spacious, functional layout with ample storage throughout. Both bedrooms feature Bos...Listing by: -
$1,259,000 Active3 bds • 2 ba • 1,622 sqft
6 Shaw Rd, Belmont, MA 02478
A rare opportunity to own this quintessential ranch in Belmont's highly sought-after Burbank neighborhood. Situated on a nearly 10,000 sq ft level lot, the expansive backyard offers exceptional space for entertaining, outdoor dining, gardening, recre...Listing by: -
$1,249,000 Active2 bds • 2 ba • 1,246 sqft
1515 Commonwealth Ave 311, Boston, MA 02135
NEW CONSTRUCTION! 2BED+DEN WITH 2 GARAGE SPACES READY FOR OCCUPANCY! Live the life of luxury on higher ground! Introducing 1515 Comm Ave, the top tier luxury condo community in the heart of vibrant Brighton. Designed & built to foster Feng Shui, our...Listing by:
Similar Priced Comparison
-
$1,160,000 Active4 bds • 2 ba • 1400 sqft
2 Marigold Ave
- Home smaller by 40 sqft
- Lot smaller by 8,068 sqft
- Newer by 32 years
Listing by: -
$875,000 Active4 bds • 3 ba • 2050 sqft
58 Upland Road
- Home larger by 610 sqft
- Lot larger by 2,932 sqft
- Older by 69 years
Listing by: -
New$849,900 Active2 bds • 1 ba • 884 sqft
7 Upland Terrace
- Home smaller by 556 sqft
- Lot larger by 1,943 sqft
- Newer by 46 years
Listing by: -
$827,000 Active4 bds • 3 ba • 2354 sqft
6 Hovey Ave
- Home larger by 914 sqft
- Lot smaller by 7,218 sqft
- Newer by 9 years
Listing by: -
$999,900 Active2 bds • 2 ba • 1057 sqft
16 Stearns 302
- Home smaller by 383 sqft
- Lot smaller by 13,068 sqft
- Newer by 74 years
Listing by: -
$1,239,000 Active Under Contract3 bds • 3 ba • 3129 sqft
642 Worcester St
- Home larger by 1,689 sqft
- Lot smaller by 1,868 sqft
- Older by 97 years
Listing by: -
$899,000 Active4 bds • 2 ba • 1866 sqft
62 Bacon Street
- Home larger by 426 sqft
- Lot smaller by 3,067 sqft
- Older by 1 years
Listing by: -
$1,195,000 Active2 bds • 3 ba • 1909 sqft
286 Linden Street 286
- Home larger by 469 sqft
- Lot smaller by 13,068 sqft
- Newer by 35 years
Listing by: -
$1,249,900 Active5 bds • 4 ba • 2864 sqft
48 Bradford Rd
- Home larger by 1,424 sqft
- Lot larger by 2,069 sqft
- Newer by 2 years
Listing by: -
New$1,198,000 Active3 bds • 2 ba • 1813 sqft
296 Linden St.
- Home larger by 373 sqft
- Lot smaller by 6,578 sqft
- Older by 41 years
Listing by: -
$1,195,000 Active4 bds • 3 ba • 3065 sqft
6 Brewster Rd
- Home larger by 1,625 sqft
- Lot larger by 28,343 sqft
- Newer by 12 years
Listing by: -
$1,075,000 Active1 bds • 2 ba • 1205 sqft
63 Garden Rd C5
- Home smaller by 235 sqft
- Lot smaller by 13,068 sqft
- Newer by 35 years
Listing by: -
$860,000 Active4 bds • 3 ba • 1975 sqft
17 Retrop Rd
- Home larger by 535 sqft
- Lot larger by 1,259 sqft
- Older by 1 years
Listing by: -
$999,000 Active3 bds • 2 ba • 1858 sqft
76 South Ave 201
- Home larger by 418 sqft
- Lot smaller by 13,068 sqft
- Newer by 69 years
Listing by: -
$879,000 Active4 bds • 4 ba • 2640 sqft
254 N Main Street
- Home larger by 1,200 sqft
- Lot smaller by 8,067 sqft
- Older by 51 years
Listing by: -
$1,150,000 Active4 bds • 3 ba • 2446 sqft
52 Washington Street
- Home larger by 1,006 sqft
- Lot smaller by 6,138 sqft
- Older by 51 years
Listing by: -
$1,150,000 Active4 bds • 3 ba • 2446 sqft
52 Washington Street
- Home larger by 1,006 sqft
- Lot smaller by 6,138 sqft
- Older by 51 years
Listing by: -
$949,000 Active4 bds • 4 ba • 2117 sqft
3 Wilson St 3
- Home larger by 677 sqft
- Lot smaller by 13,068 sqft
- Newer by 74 years
Listing by: -
$1,088,000 Active Under Contract3 bds • 2 ba • 1521 sqft
6 Oakland Circle
- Home larger by 81 sqft
- Lot smaller by 3,058 sqft
- Older by 61 years
Listing by: -
$1,194,000 Active5 bds • 2 ba • 3300 sqft
136 Commonwealth Rd
- Home larger by 1,860 sqft
- Lot larger by 8,712 sqft
- Older by 102 years
Listing by:
Nearby Locations
Communities
- Fells Homes For Sale
- Overbrook Homes For Sale
- Wellesley Hills Homes For Sale
- Cochituate Homes For Sale
- Needham Heights Homes For Sale
- Auburndale Homes For Sale
- Cochituate Homes For Sale
- Waban Homes For Sale
- Birds Hill Homes For Sale
- West Newton Homes For Sale
- Four Corners Homes For Sale
- Saxonville Homes For Sale
- Newtonville Homes For Sale
- Newton Centre Homes For Sale
- Oak Hill Homes For Sale
- Dexter Homes For Sale
- Bowen - Thompsonville Homes For Sale
- Watertown West End Homes For Sale
- West End Homes For Sale
- Downtown Homes For Sale
Nearby Zips
- 02482 Homes For Sale
- 02481 Homes For Sale
- 01760 Homes For Sale
- 02493 Homes For Sale
- 02492 Homes For Sale
- 02030 Homes For Sale
- 02494 Homes For Sale
- 02468 Homes For Sale
- 01778 Homes For Sale
- 02465 Homes For Sale
- 02453 Homes For Sale
- 02461 Homes For Sale
- 01770 Homes For Sale
- 02460 Homes For Sale
- 02451 Homes For Sale
- 02459 Homes For Sale
- 02052 Homes For Sale
- 02090 Homes For Sale
- 02452 Homes For Sale
- 02458 Homes For Sale
Nearby Cities
- Wellesley, MA Homes for Sale
- Natick, MA Homes for Sale
- Weston, MA Homes for Sale
- Needham, MA Homes for Sale
- Cochituate, MA Homes for Sale
- Dover, MA Homes for Sale
- Needham Heights, MA Homes for Sale
- Wayland, MA Homes for Sale
- Newton, MA Homes for Sale
- Sherborn, MA Homes for Sale
- Waltham, MA Homes for Sale
- Medfield, MA Homes for Sale
- Westwood, MA Homes for Sale
- Lincoln, MA Homes for Sale
- Dedham, MA Homes for Sale
- Framingham, MA Homes for Sale
- Watertown Town, MA Homes for Sale
- Millis, MA Homes for Sale
- East Holliston, MA Homes for Sale
- Sudbury, MA Homes for Sale
Similar Searches
- Wellesley Land for Sale
- Wellesley New Homes for Sale
- Wellesley Single Story Homes for Sale
- Wellesley Homes with Pools for Sale
- Wellesley Cheap Homes for Sale
- Wellesley Luxury Homes for Sale
- Wellesley Condos for Sale
- Wellesley Town Homes for Sale
- Wellesley Commercial for Sale
- Wellesley Open Houses for Sale
- Wellesley Two Car Garage Homes for Sale
- Wellesley Large Lots for Sale
- National Listings
- National Home Values
- Properties in MA
- Home Values in MA
- Other properties in Norfolk, MA
- Other properties in 02481, MA
- Home Values in Wellesley, MA
Frequently Asked Questions for 20 Chesterton Rd
Source: Realty.com
20 Chesterton Rd, Wellesley, MA 02481 in Wellesley, MA 02481 is a single family listed at $1,100,000. Highlights include 3 bedrooms, 2 bathrooms, 1,440 sq. ft., built in 1951, 0.30 acre lot, $764 per sq. ft.. Realty.com has 31 photos, sales history, school insights, and mortgage tools for this listing.
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 2026-07-11 02:14:54. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.