42 Chestnut St, Wellesley, MA 02481
Property image
Property image
OFF MARKET

$3,255,700

Trulia Estimate
  • 5 Beds
  • 4.5 Baths
  • 5,112 sqft (on 0.32 acres)

42 Chestnut St, Wellesley, MA 02481

Est. Refi. Payment $19,909/mo*
Refinance Your Home
Currently Off Market - Sold Sep 14, 2020 for $2,345,325

Home Value

Trulia Estimate
$3.26M
Since last month
Decreased$81K (-2.4%)
Since last year
Increased$40K (+1.2%)
Since last sale
Increased$894K (+38.1%)
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 +77% in the last 10 years
MonthEstimated value
2026
September 2026$3.24M
August 2026$3.26M
July 2026$3.32M
June 2026$3.32M
May 2026$3.32M
April 2026$3.28M
March 2026$3.3M
February 2026$3.15M
January 2026$3.14M
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
40 Chestnut St, Wellesley, MA
0.02
Single-Family Home
$2,450,000
05/06/26
5
3.5
3,369
7 Garden Rd, Wellesley, MA
0.27
Single-Family Home
$2,059,981
09/25/25
5
3.5
4,643
3 Garden Rd, Wellesley, MA
0.24
Single-Family Home
$2,500,000
03/05/26
4
3.5
4,870
1 Clock Tower Dr, Wellesley, MA
0.45
Single-Family Home
$2,500,000
04/13/26
5
4.5
5,261
18 Rockland St, Wellesley Hills, MA
0.47
Single-Family Home
$3,150,000
09/10/26
5
4.5
5,105
33 Hundreds Cir, Wellesley, MA
0.27
Single-Family Home
$3,900,000
08/14/26
5
3.5
5,074
10 Lanark Rd, Wellesley, MA
0.09
Single-Family Home
$4,400,000
06/29/26
6
3.5
7,404
7 Cliff Rd, Wellesley, MA
0.29
Single-Family Home
$1,865,000
04/02/26
5
3.5
3,774
7 Bemis Rd, Wellesley, MA
0.53
Single-Family Home
$2,350,000
06/09/26
5
5.5
4,550
25 Shaw Rd, Wellesley, MA
0.52
Single-Family Home
$1,825,000
03/06/26
5
4.5
4,580

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
40 Chestnut St, Wellesley, MA 02481
0.02
$2,450,000
5
3.5
3,369
Recently Sold
21 Cushing Rd, Wellesley, MA 02481
0.14
$3,834,900
5
5
4,558
Off Market
14 Rockridge Rd, Wellesley, MA 02481
0.10
$4,494,000
6
5.5
5,030
Off Market
46 Garden Rd, Wellesley, MA 02481
0.11
$3,627,100
4
4.5
4,636
Off Market
8 Cypress Rd, Wellesley, MA 02481
0.15
$1,799,000
4
3.5
2,714
For Sale
10 Lanark Rd, Wellesley, MA 02481
0.09
$4,400,000
6
3.5
7,404
Recently Sold
12 Cypress Rd, Wellesley, MA 02481
0.16
$2,701,100
5
3.5
3,390
Off Market
15 Rockridge Rd, Wellesley, MA 02481
0.12
$3,346,500
4
3.5
4,100
Off Market
21 Rockridge Rd, Wellesley, MA 02481
0.13
$2,933,800
5
3.5
3,423
Off Market
37 Garden Rd, Wellesley, MA 02481
0.14
$3,141,700
6
4.5
4,297
Off Market
11 Cypress Rd, Wellesley, MA 02481
0.19
$3,326,200
6
5
4,665
Off Market
63 Garden Rd #C1, Wellesley, MA 02481
0.14
$1,917,000
2
2
1,643
Off Market

Local Information

  • Map ViewExplore the area around 42 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1993
0.32 acre lot
5,112 sqft
$637/sqft
Garage

About this House

Stunning Colonial in desirable Wellesley Farms neighborhood offers flexible and inviting floor plan with stylish finishes throughout. Bright open foyer leads to elegant fireplaced living room with French doors opening to much sought-after private home office featuring custom built-ins. Expansive sun filled dining room with bay window leads to gourmet chefs kitchen including center island,  stainless steel appliances, breakfast area and butler pantry. Fantastic family room with fireplace and access to private outdoor patio provides excellent entertaining options and indoor/outdoor living opportunity. Generous master suite includes spa-like bath and spacious walk in closet with built in organization features. Three additional bedrooms, bonus space, and laundry room complete the second floor. Beautiful professionally landscaped grounds surround two stone patios and wonderful screened in porch featuring gorgeous stone fireplace. Fantastic opportunity in an excellent location!
42 Chestnut St, Wellesley, MA 02481 is a 5 bedroom, 6 bathroom, 5,112 sqft single-family home built in 1993. It last sold for $2,345,325 on Sep 14, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,255,700.

Home Details for 42 Chestnut St

Interior Features

Heating & Cooling
Heating: Baseboard, Forced Air, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Concrete, Hardwood
Interior Details
Number of Rooms: 10Ceiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodPatioSprinkler System
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached

Property Information

Year Built
Year Built: 1993
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.32 acres

Price and Tax history

DateEventPrice
Sep 14, 2020
Source: N/A
Sold
$2,345,325
Jul 31, 2020
Source: Agent Provided
Pending
$2,450,000
Jul 18, 2020
Source: Agent Provided
Listed For Sale
$2,450,000
Apr 7, 2020
Source: N/A
Sold
$2,295,000
Jun 11, 2013
Source: N/A
Sold
$1,590,000

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

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
    Flag
  • 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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 42 Chestnut St

  • What is 42 Chestnut St estimated to be worth?
    Trulia's estimated value for 42 Chestnut St in Wellesley, MA is $3,255,700.
  • What is the price history for 42 Chestnut St?
    42 Chestnut St in Wellesley, MA last sold for $2,345,325 in September 2020.
  • 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 42 Chestnut St have air conditioning?
    Yes, 42 Chestnut St in Wellesley, MA has air conditioning.
  • Does 42 Chestnut St have laundry facilities?
    Yes, 42 Chestnut St in Wellesley, MA has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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