41 Chesterton Rd, Wellesley, MA 02481
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Property image
OFF MARKET

41 Chesterton Rd
Wellesley, MA 02481

  • 5 Beds
  • 4.5 Baths
  • 5,516 sqft

$3,037,800

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $18,242/mo*
Refinance Your Home

$3,037,800

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $18,242/mo*
Refinance Your Home
5 Beds
4.5 Baths
5,516 sqft

Local Information

  • Map ViewExplore the area around 41 Chesterton Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2006
Living Area
5,516 sqft
Price/Sqft
$551
Parking
2 Car Garage

About this House

Right in the heart of one of Wellesley’s most beloved neighborhoods, this stunning 2006 Colonial features over 5500 sq ft of living space with impressive proportions and fabulous details. A testament to warm family living, this home has everything on your wish list including the extras current new builds miss: lovely foyer, elegant living room w/fireplace, large dining room, first floor home office, gorgeous white kitchen w/ ample eating area, big family room w/fireplace. The primary suite is gorgeous, featuring raised ceiling, 2 walk-in closets & double vanity bath with tub. 4 more generous bedrooms and laundry room on 2nd floor. Spacious unfinished third floor provides expansion potential. Great mudroom, 2 car garage w/custom storage and extra space. Fabulous lower level w/rec room, playroom & full bath. A gorgeous bluestone patio and level landscaped yard are ready for fun and games. Walk to Bates and Boulder Brook reservation from this picture perfect location!
41 Chesterton Rd, Wellesley, MA 02481 is a 5 bedroom, 5 bathroom, 5,516 sqft single-family home built in 2006. It last sold for $2,950,000 on Aug 1, 2024 (4% above the $2,850,000 asking price). It is currently off market. The Trulia Estimate is $3,037,800, with a rent estimate of $10,660/month.

Home Details for 41 Chesterton Rd

Interior Features

Interior Details
Basement: Full,Finished,Interior Entry,BulkheadNumber of Rooms: 13Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5516 Square Feet
Appliances & Utilities
Utilities: for Gas RangeAppliances: Gas Water HeaterLaundry: Second Floor
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Has a FireplaceNo Spa
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Insulated WindowsDoor: Insulated DoorsFlooring: Wood
Levels, Entrance, & Accessibility
Accessibility: NoFloors: Wood
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: PatioExterior: PatioFoundation: Concrete Perimeter
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Garage Door Opener,Workshop in Garage,Paved Drive,Off Street
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:180 R:089 S:, 264347

Price & Status

Price
List Price: $2,850,000
Status Change & Dates
Off Market Date: Mon May 20 2024

Active Status

MLS Status: Sold

Location

Direction & Address
City: WellesleyCommunity: Boulder Brook
School Information
Elementary School: BatesJr High / Middle School: WmsHigh School: Whs

Building

Building Area
Building Area: 5516 Square Feet

Community

Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Bike Path, Conservation Area, House of Worship, Private School, Public School, T-Station, UniversityNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 10280 sqft

Miscellaneous

BasementMls Number: 73239042

Additional Information

Public TransportationShoppingTennis Court(s)ParkWalk/Jog TrailsBike PathConservation AreaHouse of WorshipPrivate SchoolPublic SchoolT-StationUniversity
Last check for updates: about 11 hours ago
Listed by Christine Lawrence, (781) 820-1336
Rutledge Properties, (781) 235-4663
Bought with: Betsy Kessler, (617) 306-6884, Rutledge Properties, (781) 235-4663
Source: MLS PIN, MLS#73239042

Price History for 41 Chesterton Rd

DatePriceEventSource
05/21/2026$3,150,000ListingRemovedMLS PIN #73498584
05/05/2026$3,150,000PriceChange
MLS PIN #73498584
04/08/2026$3,295,000Listed For SaleMLS PIN #73498584
08/01/2024$2,950,000Sold
MLS PIN #73239042
05/16/2024$2,850,000Listed For SaleMLS PIN #73239042
12/15/2006$1,575,000Sold
N/A
03/06/2006$740,000Sold
N/A

Market trends in Wellesley

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.99M
$300KMoM
Sale-to-List Price
100.1%
1.4%MoM
Price per sq ft
$649
$56MoM
Available listings
112
1MoM
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Property Tax and Assessment

Year2025
Tax$24,836
Assessment$2,416,000
Home facts updated by county records

Comparable Sales for 41 Chesterton Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
53 Chesterton Rd, Wellesley, MA
0.06
Single-Family Home
$3,225,000
06/01/26
5
5.5
5,779
51 Boulder Brook Rd, Wellesley, MA
0.15
Single-Family Home
$3,270,000
12/09/25
5
4.5
4,947
19 Northgate Rd, Wellesley, MA
0.13
Single-Family Home
$3,000,000
04/21/26
5
5.5
4,886
15 Parker Rd, Wellesley, MA
0.24
Single-Family Home
$3,100,000
06/01/26
5
5
5,227
20 Parker Rd, Wellesley, MA
0.27
Single-Family Home
$2,825,000
04/14/26
6
3.5
4,393
19 Louis Dr, Wellesley, MA
0.05
Single-Family Home
$1,825,000
12/03/25
4
3.5
2,820
27 Garrison Rd, Wellesley, MA
0.41
Single-Family Home
$3,100,000
06/01/26
5
5.5
5,926
6 Boulder Brook Rd, Wellesley, MA
0.09
Single-Family Home
$1,925,000
04/15/26
4
3.5
2,813
23 Pilgrim Rd, Wellesley, MA
0.43
Single-Family Home
$2,628,000
05/12/26
4
3.5
4,102
25 Bryn Mawr Rd, Wellesley, MA
0.39
Single-Family Home
$2,325,000
08/18/25
5
3.5
4,072

Nearby homes

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Assigned Schools

These are the assigned schools for 41 Chesterton Rd.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Wellesley

At least 124 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 87 % Say parking is easy

  • 85 % Say people would walk alone at night

  • 84 % Say yards are well-kept

  • 80 % Say car is needed

  • 79 % Say there are sidewalks

  • 76 % Say kids play outside

  • 75 % Say there's holiday spirit

  • 74 % Say streets are well-lit

  • 73 % Say there's wildlife

  • 72 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 67 % Say it's walkable to restaurants

  • 66 % Say neighbors are friendly

  • 65 % Say there are community events

  • 63 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Mike Holiday
    "Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
    0
    Flag
  • Emilyperrottet
    "Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
    0
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  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
    Flag
  • Trulia User
    "Lots of trails and other dogs in the area, many pet stores in the area as well. Dogs are well behaved and friendly. "
    0
    Flag
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
    0
    Flag
  • Sdipietro369
    "I am a visitor to this area. The neighborhood seems very nice with Babson College right around the corner. Shops within a close distance. "
    3
    Flag
  • Katrina C.
    "You feel you're kids are safe here in town. Everyone is friendly and we're all neighbors. It's a lovely town with a community feeling. "
    2
    Flag
  • Jamie.solomon1
    "I lived in Weston for two years and it’s a delightful town, with gorgeous land and large houses. Usually at least an acre"
    1
    Flag
  • Cmt138
    "Great access to commuter rail from either Wellesley Square or Wellesley Hills. Easy 10-15 min walk. Better parking from Wellesley Square. Usually takes about 1/2 hour to Back Bay. Driving into Boston can take a little more time with traffic to cross town to Mass Pike."
    2
    Flag
  • Laura M.
    "There are lots of dogs in our neighborhood- people walk them all the time. Dogs are welcome at Morse’s pond in the off season. "
    1
    Flag
  • Bruce C.
    "Lots of other dog owners who walk their dogs all the time. Also plenty of space to run with dogs on a trail or away from streets. "
    1
    Flag
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
    0
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  • Srodousakis
    "Wellesley is a beautiful but very privileged neighborhood. It is very safe and people are friendly. Schools are great! There is a cute downtown and generally it’s a great place to raise kids. "
    0
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  • Molly R.
    "i love my neighborhood. everyone is so kind and welcoming. we often times have little gatherings or block parties. everyone knows each other and we are a very close community. "
    0
    Flag
  • Victoria V.
    "That I live on route 16 and nobody lets me out of my driveway in the morning and I have to leave for work an hour early just because of that."
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 41 Chesterton Rd

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Off Market Homes Near 41 Chesterton Rd

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The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.