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

$3,037,800

Trulia Estimate
  • 5 Beds
  • 4.5 Baths
  • 5,516 sqft

41 Chesterton Rd, Wellesley, MA 02481

Est. Refi. Payment $18,891/mo*
Refinance Your Home
Currently Off Market - Sold Aug 1, 2024 for $2,950,000

Home Value

Trulia Estimate
$3.04M
Since last month
Decreased$4K (-0.1%)
Since last year
Decreased$56K (-1.8%)
Since last sale
Increased$79K (+2.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +63% in the last 10 years
MonthEstimated value
2026
September 2026$3.03M
August 2026$3.03M
July 2026$3.04M
June 2026$3.1M
May 2026$3.05M
April 2026$3.22M
March 2026$3.07M
February 2026$3.04M
January 2026$3.06M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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
449 Weston Rd, Wellesley, MA
0.10
Single-Family Home
$2,699,000
08/28/26
5
5.5
4,000
15 Parker Rd, Wellesley, MA
0.24
Single-Family Home
$3,100,000
06/01/26
5
5
5,227
23 Northgate Rd, Wellesley, MA
0.13
Single-Family Home
$2,635,000
08/31/26
5
2.5
3,413
20 Parker Rd, Wellesley, MA
0.27
Single-Family Home
$2,825,000
04/14/26
6
3.5
4,393
28 Parker Rd, Wellesley, MA
0.30
Single-Family Home
$3,265,000
09/15/26
6
5.5
5,080
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

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1 Richland Rd, Wellesley, MA 02481
0.05
$2,536,400
4
2.5
4,152
Off Market
34 Chesterton Rd, Wellesley, MA 02481
0.04
$3,412,600
5
4.5
4,781
Off Market
6 Boulder Brook Rd, Wellesley, MA 02481
0.09
$1,925,000
4
3.5
2,813
Recently Sold
19 Louis Dr, Wellesley, MA 02481
0.05
$1,825,000
4
3.5
2,820
Recently Sold
449 Weston Rd, Wellesley, MA 02482
0.10
$2,699,000
5
5.5
4,000
Recently Sold
447 Weston Rd, Wellesley, MA 02482
0.10
$1,808,100
4
3
2,076
Off Market
27 Boulder Brook Rd, Wellesley, MA 02481
0.09
$2,400,600
4
2.5
3,636
Off Market
53 Chesterton Rd, Wellesley, MA 02481
0.06
$3,225,000
5
5.5
5,779
Recently Sold
8 Beverly Rd, Wellesley, MA 02481
0.13
$3,024,400
4
4.5
5,704
Off Market
60 Chesterton Rd, Wellesley, MA 02481
0.09
$2,617,900
5
4
3,611
Off Market
460 Weston Rd, Wellesley, MA 02482
0.16
$3,172,700
5
5.5
5,904
Off Market

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

Single-Family Home
Built in 2006
5,516 sqft
$551/sqft
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). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,037,800.
Last check for updates: about 24 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

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

Price and Tax history

DateEventPrice
May 21, 2026
Source: MLS PIN #73498584
ListingRemoved
$3,150,000
May 5, 2026
Source: MLS PIN #73498584
PriceChange
$3,150,000
Price decreased by 4%
Apr 8, 2026
Source: MLS PIN #73498584
Listed For Sale
$3,295,000
Aug 1, 2024
Source: MLS PIN #73239042
Sold
$2,950,000
May 16, 2024
Source: MLS PIN #73239042
Listed For Sale
$2,850,000

Market trends in Wellesley

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.18M
$33.75KMoM
Sale-to-List Price
100.7%
0.1%MoM
Price per sq ft
$685
$19MoM
Available listings
71
16MoM

Around this home

View nearby schools on GreatSchools
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
    Flag
  • 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
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  • 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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LGBTQ Local Legal Protections

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.

Frequently asked questions about 41 Chesterton Rd

  • What is 41 Chesterton Rd estimated to be worth?
    Trulia's estimated value for 41 Chesterton Rd in Wellesley, MA is $3,037,800.
  • What is the price history for 41 Chesterton Rd?
    41 Chesterton Rd in Wellesley, MA last sold for $2,950,000 in August 2024.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Wellesley?
    The median sale price in Wellesley is $2.18M. That is up $33.75K from the prior month.
  • Does 41 Chesterton Rd have air conditioning?
    Yes, 41 Chesterton Rd in Wellesley, MA has air conditioning.
  • Does 41 Chesterton Rd have laundry facilities?
    Yes, 41 Chesterton Rd in Wellesley, MA has laundry facilities.

Explore by feature - Pet Friendly

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