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

21 Chestnut St
Wellesley, MA 02481

  • 4 Beds
  • 2.5 Baths
  • 2,644 sqft (on 0.25 acres)

$2,066,300

Trulia Estimate
as of Jul 7, 2026

$2,066,300

Trulia Estimate
as of Jul 7, 2026
4 Beds
2.5 Baths
2,644 sqft
(on 0.25 acres)

Local Information

  • Map ViewExplore the area around 21 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Nestled in the heart of the Cliff Estates, a charming Victorian maintains the character of yesterday with the updates today's buyers are looking for.The front walk guides you to a lovely screened porch perfect for summer evenings. The foyer with turned stair case is flanked by a large dining room and double parlor. Pristine maple floors throughout the home are warm and welcoming. Always the heart of the home an updated chef's kitchen,granite counters,6 burner gas stove and adjacent family room. A mudroom entry way with slate floor rounds out the first floor.The second floor has three good size bedrooms and family bath in addition to a large master suite with private bath and dressing area which creates a quiet retreat. Exquisite gardens,lovingly tended, enhance the grounds,everywhere you turn specimen plantings and flowering shrubs. Enjoy dinner on the deck off the kitchen,relax in the serene setting. A quick stroll to Boston Train,Cafe Nero,Post Office,restaurants and walking trails.
21 Chestnut St, Wellesley, MA 02481 is a 4 bedroom, 3 bathroom, 2,644 sqft single-family home built in 1880. It last sold for $1,447,000 on Aug 28, 2020. It is currently off market. The Trulia Estimate is $2,066,300, with a rent estimate of $6,512/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 21 Chestnut St

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood, Slate
Interior Details
Number of Rooms: 8
Appliances & Utilities
DishwasherDryerWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Shingle Not Wood
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 1880Year Updated: 1983
Property Type / Style
Property Type: Single Family HomeArchitecture: Queen Anne / Victorian

Building

Levels, Entrance, & Accessibility
Disabled Access

Community

Units in Building: 1

Lot Information

Lot Area: 10890 sqft

Price History for 21 Chestnut St

DatePriceEventSource
08/28/2020$1,447,000Sold
N/A
07/18/2020$1,395,000PendingAgent Provided
07/15/2020$1,395,000Listed For SaleAgent Provided

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$15,091
Assessment$1,468,000
Home facts updated by county records

Comparable Sales for 21 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
54 Colburn Rd, Wellesley, MA
0.27
Single-Family Home
$1,655,000
01/30/26
4
2.5
2,204
500 Worcester St, Wellesley, MA
0.30
Single-Family Home
$1,340,000
08/28/25
4
2.5
3,257
92 Woodlawn Ave, Wellesley, MA
0.34
Single-Family Home
$1,953,000
06/03/26
4
2.5
2,627
40 Chestnut St, Wellesley, MA
0.10
Single-Family Home
$2,450,000
05/06/26
5
3.5
3,369
15 Clifton Rd, Wellesley, MA
0.44
Single-Family Home
$1,635,650
04/16/26
4
2.5
2,112
34 Seaward Rd, Wellesley, MA
0.47
Single-Family Home
$1,675,000
09/08/25
5
2.5
3,347
26 Kimlo Rd, Wellesley, MA
0.32
Single-Family Home
$1,065,800
12/02/25
3
2
1,505
4 Southwick Cir, Wellesley, MA
0.47
Single-Family Home
$1,690,000
11/20/25
3
1.5
2,014
3 Rockland St, Wellesley, MA
0.43
Single-Family Home
$1,155,000
08/01/25
3
2
2,304
3 Garden Rd, Wellesley, MA
0.13
Single-Family Home
$2,500,000
03/05/26
4
3.5
4,870

Nearby homes

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Assigned Schools

These are the assigned schools for 21 Chestnut St.
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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Explore by feature - Pet Friendly

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Homes for sale near 21 Chestnut St

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Off Market Homes Near 21 Chestnut St

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