23 Chestnut St, Wellesley, MA 02481
OFF MARKET

$3,385,900

Trulia Estimate
as of Sep 7, 2026
  • 5 Beds
  • 3.5 Baths
  • 4,068 sqft

23 Chestnut St, Wellesley, MA 02481

Home Highlights

Single-Family Home
4,068 sqft
$832/sqft

Local Information

  • Map ViewExplore the area around 23 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Fabulous 5 bedroom home in Wellesley Farms showcasing oak floors, high ceilings and a beautiful kitchen with quartz counters, stainless steel appliances, and breakfast nook with window seating. Flexible first floor living space boasts expansive fireplaced living room and dining room with butler's pantry for extra storage. Spectacular 2nd floor primary suite with spa-like marble bathroom, large walk-in closet plus additional bedroom & full bathroom. The sun-filled 3rd floor offers an office space, plus 2 bonus bedrooms and a full bathroom, perfect for guests or family members. The home also includes a private patio with lush level gardens and a covered porch, ideal for entertaining or relaxing outdoors. 2 car garage. Conveniently located close to train station, shopping, restaurants, and all major routes to Boston, this home offers both luxury and convenience. This home comes ideally furnished but landlord will consider unfurnished. Ideal dates 8/15/25-6/30/26 will consider to 8/14/26.

-References required
-Listing brokerage fee: 1 month
-Last month required
-50/50 Cooperating compensation
23 Chestnut St, Wellesley, MA 02481 is a 5 bedroom, 4 bathroom, 4,068 sqft single-family home. It last sold for $2,710,000 on Jun 13, 2022 (19,257% above the $14,000 asking price). More recently, it was listed as a rental in May 2025 with an asking price of $14,000 per month. That rental listing was removed on June 9, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,385,900, with a rent estimate of $7,942/month.

Home Details for 23 Chestnut St

Interior Features

Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: Central AirHeating Fuel: Baseboard
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood, Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Detached, On Site

Comparable Sales for 23 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
40 Chestnut St, Wellesley, MA
0.09
Single-Family Home
$2,450,000
05/06/26
5
3.5
3,369 sqft
7 Garden Rd, Wellesley, MA
0.16
Single-Family Home
$2,059,981
09/25/25
5
3.5
4,643 sqft
3 Garden Rd, Wellesley, MA
0.14
Single-Family Home
$2,500,000
03/05/26
4
3.5
4,870 sqft
7 Cliff Rd, Wellesley, MA
0.18
Single-Family Home
$1,865,000
04/02/26
5
3.5
3,774 sqft
44 Bradford Rd, Wellesley, MA
0.24
Single-Family Home
$3,100,000
06/02/26
5
5.5
4,785 sqft
26 Edmunds Rd, Wellesley, MA
0.40
Single-Family Home
$3,115,000
01/09/26
4
3.5
4,294 sqft
1 Clock Tower Dr, Wellesley, MA
0.35
Single-Family Home
$2,500,000
04/13/26
5
4.5
5,261 sqft
33 Hundreds Cir, Wellesley, MA
0.37
Single-Family Home
$3,900,000
08/14/26
5
3.5
5,074 sqft
101 Edmunds Rd, Wellesley, MA
0.45
Single-Family Home
$3,200,000
07/07/26
5
4.5
4,010 sqft
10 Lanark Rd, Wellesley, MA
0.18
Single-Family Home
$4,400,000
06/29/26
6
3.5
7,404 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Rental Market Trends in Wellesley

Last updated Sep 2026
Trulia Rent Estimate$7,942/mo
Average rent
$5.2K
$1.03KMoM
Available listings
29
View rental market trends in Wellesley, MA

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

Price and Tax history

DateEventPrice
Jun 9, 2025
Source: Zillow Rentals
ListingRemoved
$14,000
May 19, 2025
Source: Zillow Rentals
Listed For Rent
$14,000
Jun 13, 2022
Source: MLS PIN #72971202
Sold
$2,710,000
Apr 25, 2022
Source: MLS PIN #72971202
Listed For Sale
$2,675,000
Oct 15, 2020
Source: Agent Provided
ListingRemoved
$2,995,000

Frequently asked questions about 23 Chestnut St

  • What is 23 Chestnut St estimated to be worth?
    Trulia's estimated value for 23 Chestnut St in Wellesley, MA is $3,385,900.
  • What is the price history for 23 Chestnut St?
    23 Chestnut St in Wellesley, MA last sold for $2,710,000 in June 2022.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Wellesley?
    The median sale price in Wellesley is $2.15M. That is up $161K from the prior month.
  • Does 23 Chestnut St have air conditioning?
    Yes, 23 Chestnut St in Wellesley, MA has air conditioning.
  • Does 23 Chestnut St have laundry facilities?
    Yes, 23 Chestnut St in Wellesley, MA has in-unit laundry.

Homes for rent near 23 Chestnut St

Skip to last item
Skip to first item

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
Skip to last item
  • Results are loading
Skip to first item