101 Overbrook Dr, Wellesley, MA 02482
Property image
Property image
OFF MARKET

$1,611,700

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 2,468 sqft (on 0.28 acres)

101 Overbrook Dr, Wellesley, MA 02482

Est. Refi. Payment $10,066/mo*
Refinance Your Home
Currently Off Market - Sold Jul 29, 2016 for $910,000

Home Value

Trulia Estimate
$1.61M
Since last month
Increased$29K (+1.8%)
Since last year
Increased$75K (+4.9%)
Since last sale
Increased$704K (+77.3%)
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 +79% in the last 10 years
MonthEstimated value
2026
October 2026$1.61M
September 2026$1.58M
August 2026$1.58M
July 2026$1.6M
June 2026$1.64M
May 2026$1.66M
April 2026$1.61M
March 2026$1.62M
February 2026$1.55M
January 2026$1.52M
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
30 Colby Rd, Wellesley, MA
0.10
Single-Family Home
$1,600,000
12/11/25
4
2.5
2,520
107 Overbrook Dr, Wellesley, MA
0.05
Single-Family Home
$1,400,000
08/03/26
3
2.5
2,274
3 Sunnyside Ave, Wellesley, MA
0.14
Single-Family Home
$1,120,000
03/06/26
3
2.5
2,388
7 Oakdale Ave, Wellesley, MA
0.19
Single-Family Home
$1,820,000
05/29/26
4
2.5
2,807
11 Ingleside Rd, Natick, MA
0.16
Single-Family Home
$850,000
07/02/26
3
1.5
1,770
16 Sunnyside Ave, Wellesley, MA
0.18
Single-Family Home
$1,180,000
08/11/26
3
1.5
1,743
7 Whitney Cir, Natick, MA
0.29
Single-Family Home
$1,480,000
07/30/26
4
3
2,818
1 Sunnyside Ave, Wellesley, MA
0.16
Single-Family Home
$1,865,000
03/27/26
4
4.5
3,119
115 Parker Rd, Wellesley, MA
0.26
Single-Family Home
$1,320,000
11/21/25
4
1.5
1,694
50 Parker Rd, Wellesley, MA
0.39
Single-Family Home
$1,600,000
11/14/25
4
2.5
2,147

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
95 Overbrook Dr, Wellesley, MA 02482
0.02
$1,085,300
3
1
1,200
Off Market
50 High Ledge Ave, Wellesley, MA 02482
0.02
-
-
-
-
Off Market
117 Woodside Ave, Wellesley, MA 02482
0.03
$1,415,300
3
2
1,504
Off Market
105 Overbrook Dr, Wellesley, MA 02482
0.03
$1,548,000
4
2.5
2,176
Off Market
98 Overbrook Dr, Wellesley, MA 02482
0.03
$1,729,400
4
3
2,664
Off Market
106 Overbrook Dr, Wellesley, MA 02482
0.03
$1,632,400
4
2.5
2,016
Off Market
104 Overbrook Dr, Wellesley, MA 02482
0.03
$2,023,700
4
5
2,932
Off Market
115 Woodside Ave, Wellesley, MA 02482
0.04
$1,855,100
4
3.5
2,960
Off Market
89 Overbrook Dr, Wellesley, MA 02482
0.04
$1,304,200
3
2
1,654
Off Market
116 Woodside Ave, Wellesley, MA 02482
0.04
$1,835,800
4
4
3,100
Off Market
94 Overbrook Dr, Wellesley, MA 02482
0.04
-
-
-
-
Off Market
69 Edgemoor Ave, Wellesley, MA 02482
0.04
$2,476,800
5
5.5
4,806
Off Market
112 Overbrook Dr, Wellesley, MA 02482
0.04
$1,047,200
3
3
1,060
Off Market
63 Edgemoor Ave, Wellesley, MA 02482
0.05
$1,541,600
3
2.5
1,900
Off Market
73 Edgemoor Ave, Wellesley, MA 02482
0.05
$2,088,400
4
3.5
3,572
Off Market
55 High Ledge Ave, Wellesley, MA 02482
0.05
$2,167,600
4
3.5
4,090
Off Market
107 Overbrook Dr, Wellesley, MA 02482
0.05
$1,400,000
3
2.5
2,274
Recently Sold
56 High Ledge Ave, Wellesley, MA 02482
0.05
$1,654,500
3
2.5
2,400
Off Market
112 Woodside Ave, Wellesley, MA 02482
0.06
$1,970,200
4
2.5
2,856
Off Market
90 Overbrook Dr, Wellesley, MA 02482
0.06
$2,284,400
5
4.5
4,169
Off Market

Local Information

  • Map ViewExplore the area around 101 Overbrook Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1910
0.28 acre lot
2,468 sqft
$653/sqft
Garage

About this House

WELLESLEY HOUSE BEAUTIFUL -- TURN KEY! Ideal corner lot location for this newly renovated open floor-plan cape featuring gleaming hardwood floors, new granite kitchen with stainless appliances, wet bar and built-in wine refrigerator as well as 3 baths, electrical and plumbing upgrades, updated high efficiency heating and water system as well as newly paved driveway. French doors open to a sunroom overflowing with natural light. Enjoy summer evening dinners on the patio inside the fenced in yard and peaceful nights in this spacious master suite with newly built master bath adorned with Carrera marble, oversized closets, and vaulted ceilings. Offers reviewed June 5, 2016.
101 Overbrook Dr, Wellesley, MA 02482 is a 5 bedroom, 4 bathroom, 2,468 sqft single-family home built in 1910. It last sold for $910,000 on Jul 29, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,611,700, with a rent estimate of $5,980/month.

Home Details for 101 Overbrook Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 9Types of Rooms: Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Sun RoomWet Bar
Heating & Cooling
Heating: Baseboard, GasAir ConditioningHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: VinylLawnPatio
Parking & Garage
GarageParking Space: 1Parking: Garage Attached, Off Street, On Street

Property Information

Year Built
Year Built: 1910Year Updated: 2012
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

Price and Tax history

DateEventPrice
Jul 29, 2016
Source: N/A
Sold
$910,000
Nov 18, 2011
Source: N/A
Sold
$448,000
Aug 1, 2011
Source: Agent Provided
PriceChange
$499,000
Price decreased by 9%
Jun 25, 2011
Source: Agent Provided
PriceChange
$549,900
Price decreased by 8%
Apr 27, 2011
Source: Agent Provided
Listed For Sale
$599,900

Market trends in Wellesley

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
92
21MoM
Sourced by Trulia Market Trends

Around this home

What Locals Say about Wellesley

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 79% say there are sidewalks
  • 75% say there's holiday spirit
  • 66% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
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 101 Overbrook Dr

  • What is 101 Overbrook Dr estimated to be worth?
    Trulia's estimated value for 101 Overbrook Dr in Wellesley, MA is $1,611,700.
  • What is the price history for 101 Overbrook Dr?
    101 Overbrook Dr in Wellesley, MA last sold for $910,000 in July 2016.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Wellesley?
    Residents describe Wellesley, MA as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Wellesley, MA.
  • Does 101 Overbrook Dr have laundry facilities?
    Yes, 101 Overbrook Dr in Wellesley, MA has in-unit laundry.
  • How big is the lot at 101 Overbrook Dr?
    The lot at 101 Overbrook Dr in Wellesley, MA is about 0.28 acres (12,006 sq ft).

Explore by feature - Pet Friendly

14 pet-friendly rentals in Wellesley, MA

Explore by feature - Garage

6 rentals with a garage in Wellesley, MA

Explore by feature - Air Conditioning

18 rentals with air conditioning in Wellesley, MA

Explore by feature - Washer/dryer

23 rentals with a washer/dryer in Wellesley, MA

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 101 Overbrook Dr

Skip to last item
Skip to first item

Homes for sale near 101 Overbrook Dr

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item