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

34 Chesterton Rd
Wellesley, MA 02481

  • 5 Beds
  • 4.5 Baths
  • 4,781 sqft (on 0.29 acres)

$3,366,700

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $19,696/mo*
Refinance Your Home

$3,366,700

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $19,696/mo*
Refinance Your Home
5 Beds
4.5 Baths
4,781 sqft
(on 0.29 acres)

Local Information

  • Map ViewExplore the area around 34 Chesterton Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Stunning custom-built designer home completed in 2023. This gorgeous 5+ bed, 4.5 bath is truly one of a kind. Set on a quiet family-friendly street in the Bates district, 34 Chesterton showcases timeless architectural details, beautiful millwork and top of the line finishes throughout. The first floor offers a welcoming open concept floorpan with beautiful rear-facing sun room and gourmet kitchen outfitted w/ brass fixtures, custom cabinetry, Wolf/Sub-zero appliances and honed quartzite counters. Spacious corner library/home office, powder room + mudroom with walk-in pantry complete this floor. Upstairs offers 3 equally large guest bedrooms, 2 playfully designed bathrooms, 1 full-size laundry room and stunning primary suite with walk-in closet + marble bath. Fully finished lower level offers 5th bed + full bath as well as large second entertaining area and playroom. Additional features include private blue stone patio, 2 car garage and fully fenced yard with secure gated driveway.
34 Chesterton Rd, Wellesley, MA 02481 is a 5 bedroom, 5 bathroom, 4,781 sqft single-family home built in 2023. It last sold for $3,025,000 on May 1, 2024 (12% below the $3,425,000 asking price). More recently, it was listed as a rental in May 2014 with an asking price of $3,150 per month. That rental listing was removed on May 10, 2014. It is currently off market. The Trulia Estimate is $3,366,700, with a rent estimate of $5,243/month.

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
178 days ago

Home Details for 34 Chesterton Rd

Interior Features

Interior Details
Basement: Full,FinishedNumber of Rooms: 8Types of Rooms: Master Bathroom
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4781 Square Feet
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a FireplaceNo Spa
Windows, Doors, Floors & Walls
Flooring: Marble, Hardwood
Levels, Entrance, & Accessibility
Floors: Marble, Hardwood

Exterior Features

Exterior Home Features
Patio / Porch: Porch, PatioFencing: Fenced/Enclosed, FencedExterior: Porch, Patio, Fenced YardFoundation: Concrete Perimeter
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Attached,Garage Door Opener,Paved Drive
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 2023
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Not Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:180 R:145 S:, 264346

Price & Status

Price
List Price: $3,425,000
Status Change & Dates
Off Market Date: Wed Mar 13 2024

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: Wellesley
School Information
Elementary School: Bates

Building

Building Area
Building Area: 4781 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.29 acres

Offer

Contingencies: Pending P&S

Miscellaneous

BasementMls Number: 73207063
Last check for updates: about 12 hours ago
Listed by Samantha Hollister Johnson, (339) 225-0425
Compass, (617) 206-3333
Bought with: Molly Campbell Palmer, (508) 269-0002, Gibson Sotheby's International Realty, (781) 237-8181
Source: MLS PIN, MLS#73207063

Price History for 34 Chesterton Rd

DatePriceEventSource
05/01/2024$3,025,000Sold
MLS PIN #73207063
03/12/2024$3,425,000ContingentMLS PIN #73207063
02/29/2024$3,425,000PriceChange
MLS PIN #73207063
05/10/2014$3,150ListingRemovedAgent Provided
05/10/2014$3,150PendingAgent Provided
05/01/2014$3,150Listed For RentAgent Provided
09/20/1995$358,000Sold
N/A

Market trends in Wellesley

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
111
3MoM
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Property Tax and Assessment

Year2025
Tax$28,332
Assessment$2,756,000
Home facts updated by county records

Comparable Sales for 34 Chesterton Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
19 Northgate Rd, Wellesley, MA
0.11
Single-Family Home
$3,000,000
04/21/26
5
5.5
4,886
53 Chesterton Rd, Wellesley, MA
0.10
Single-Family Home
$3,225,000
06/01/26
5
5.5
5,779
51 Boulder Brook Rd, Wellesley, MA
0.19
Single-Family Home
$3,270,000
12/09/25
5
4.5
4,947
15 Parker Rd, Wellesley, MA
0.22
Single-Family Home
$3,100,000
06/01/26
5
5
5,227
20 Parker Rd, Wellesley, MA
0.25
Single-Family Home
$2,825,000
04/14/26
6
3.5
4,393
19 Louis Dr, Wellesley, MA
0.04
Single-Family Home
$1,825,000
12/03/25
4
3.5
2,820
6 Boulder Brook Rd, Wellesley, MA
0.08
Single-Family Home
$1,925,000
04/15/26
4
3.5
2,813
27 Garrison Rd, Wellesley, MA
0.40
Single-Family Home
$3,100,000
06/01/26
5
5.5
5,926
428 Weston Rd, Wellesley, MA
0.17
Single-Family Home
$1,497,200
12/09/25
5
3.5
2,558
23 Pilgrim Rd, Wellesley, MA
0.45
Single-Family Home
$2,628,000
05/12/26
4
3.5
4,102

Nearby homes

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Assigned Schools

These are the assigned schools for 34 Chesterton Rd.
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
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  • 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
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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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Apartments for Rent

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Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

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Homes for sale near 34 Chesterton Rd

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Off Market Homes Near 34 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.