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

38 Chestnut St
Wellesley, MA 02481

  • 5 Beds
  • 4.5 Baths
  • 5,479 sqft (on 0.49 acres)

$4,512,300

Trulia Estimate
as of Jul 29, 2026
Est. Refi. Payment $26,917/mo*
Refinance Your Home

$4,512,300

Trulia Estimate
as of Jul 29, 2026
Est. Refi. Payment $26,917/mo*
Refinance Your Home
5 Beds
4.5 Baths
5,479 sqft
(on 0.49 acres)

Local Information

  • Map ViewExplore the area around 38 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1904
Lot Size
0.49 acres
Living Area
5,479 sqft
Price/Sqft
$824

About this House

Located in prestigious Wellesley Farms, this lovely 12 room colonial has been expertly renovated to bring you the best of old and new. Perfectly proportioned with three full floors of living space, this 5 bedroom, 4 1/2 bath home has retained all the charm and detail of the turn-of-the-century while offering everything you've come to expect for today's living. A gorgeous new kitchen boasts top-of-the-line appliances and opens to a sun-filled family room featuring an exquisite original fireplace and access to a handsome bluestone patio. The largest mudroom in town, a fabulous game room and private study are just some of the characteristics of this unique property. Rich in detail, this is a home of merit and distinction.
38 Chestnut St, Wellesley, MA 02481 is a 5 bedroom, 5 bathroom, 5,479 sqft single-family home built in 1904. It last sold for $3,500,000 on Nov 18, 2021. It is currently off market. The Trulia Estimate is $4,512,300, with a rent estimate of $7,969/month.

Home Details for 38 Chestnut St

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 10Types of Rooms: Recreation Room
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1904Year Updated: 2016
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Wood

Community

Units in Building: 1

Lot Information

Lot Area: 0.49 acres

Price History for 38 Chestnut St

DatePriceEventSource
11/18/2021$3,500,000Sold
MLS PIN #72894059
07/18/2016$2,980,000Sold
N/A
04/04/2016$2,995,000PriceChange
Agent Provided
03/01/2016$3,195,000Listed For SaleAgent Provided
11/03/2014$1,200,000Sold
N/A
02/28/2014$1,300,000PendingAgent Provided
02/28/2014$1,300,000Listed For SaleAgent Provided
09/11/2013$1,300,000ListingRemovedAgent Provided
06/27/2013$1,300,000Listed For SaleAgent Provided
02/19/2013$1,150,000ListingRemovedAgent Provided
01/11/2013$1,150,000PriceChange
Agent Provided
10/07/2012$1,200,000Listed For SaleAgent Provided
12/17/2009$1,599,000ListingRemovedAgent Provided
11/04/2009$1,599,000PriceChange
Agent Provided
10/19/2009$1,649,000PriceChange
Agent Provided
09/19/2009$1,699,000Listed For SaleAgent Provided
06/29/2005$1,660,000Sold
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$37,265
Assessment$3,625,000
Home facts updated by county records

Comparable Sales for 38 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
10 Lanark Rd, Wellesley, MA
0.12
Single-Family Home
$4,400,000
06/29/26
6
3.5
7,404
40 Chestnut St, Wellesley, MA
0.01
Single-Family Home
$2,450,000
05/06/26
5
3.5
3,369
3 Garden Rd, Wellesley, MA
0.21
Single-Family Home
$2,500,000
03/05/26
4
3.5
4,870
7 Garden Rd, Wellesley, MA
0.24
Single-Family Home
$2,059,981
09/25/25
5
3.5
4,643
101 Edmunds Rd, Wellesley, MA
0.39
Single-Family Home
$3,200,000
07/07/26
5
4.5
4,010
1 Clock Tower Dr, Wellesley, MA
0.43
Single-Family Home
$2,500,000
04/13/26
5
4.5
5,261
44 Bradford Rd, Wellesley, MA
0.23
Single-Family Home
$3,100,000
06/02/26
5
5.5
4,785
36 Old Farm Rd, Wellesley, MA
0.48
Single-Family Home
$3,475,000
07/31/25
5
5.5
5,359
26 Edmunds Rd, Wellesley, MA
0.40
Single-Family Home
$3,115,000
01/09/26
4
3.5
4,294
7 Cliff Rd, Wellesley, MA
0.26
Single-Family Home
$1,865,000
04/02/26
5
3.5
3,774

Nearby homes

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Assigned Schools

These are the assigned schools for 38 Chestnut St.
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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
    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
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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 38 Chestnut St

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Off Market Homes Near 38 Chestnut St

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