66 Overbrook Dr, Wellesley, MA 02482
OFF MARKET

$1,934,600

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 2,362 sqft

66 Overbrook Dr, Wellesley, MA 02482

Est. Refi. Payment $12,287/mo*
Refinance Your Home
Currently Off Market - Sold Jan 18, 2018 for $1,220,888

Home Value

Trulia Estimate
$1.94M
Since last month
Decreased$10K (-0.5%)
Since last year
Increased$73K (+3.9%)
Since last sale
Increased$720K (+59%)
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 +241% in the last 10 years
MonthEstimated value
2026
October 2026$1.94M
September 2026$1.95M
August 2026$1.92M
July 2026$1.96M
June 2026$1.97M
May 2026$1.99M
April 2026$1.95M
March 2026$1.97M
February 2026$1.9M
January 2026$1.86M
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
107 Overbrook Dr, Wellesley, MA
0.20
Single-Family Home
$1,400,000
08/03/26
3
2.5
2,274
10 Whittier Rd, Natick, MA
0.31
Single-Family Home
$1,480,000
03/02/26
5
3.5
4,050
30 Colby Rd, Wellesley, MA
0.25
Single-Family Home
$1,600,000
12/11/25
4
2.5
2,520
115 Parker Rd, Wellesley, MA
0.17
Single-Family Home
$1,320,000
11/21/25
4
1.5
1,694
17 Fenmere Ave, Wellesley, MA
0.45
Single-Family Home
$1,480,000
06/23/26
3
3.5
2,400
17 Upland Rd, Natick, MA
0.07
Single-Family Home
$1,825,000
09/09/26
4
3.5
3,136
7 Oakdale Ave, Wellesley, MA
0.32
Single-Family Home
$1,820,000
05/29/26
4
2.5
2,807
26 Buena Vista Rd, Wellesley, MA
0.54
Single-Family Home
$1,370,000
06/02/26
4
2.5
2,160
3 Pineridge Rd, Natick, MA
0.51
Single-Family Home
$1,349,000
12/23/25
4
4
2,612
3 Sunnyside Ave, Wellesley, MA
0.29
Single-Family Home
$1,120,000
03/06/26
3
2.5
2,388

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
62 Overbrook Dr, Wellesley, MA 02482
0.01
$1,780,800
4
4
3,100
Off Market
37 Edgemoor Ave, Wellesley, MA 02482
0.02
$1,856,400
4
3.5
3,006
Off Market
68 Overbrook Dr, Wellesley, MA 02482
0.02
$1,409,400
3
3
2,416
Off Market
61 Overbrook Dr, Wellesley, MA 02482
0.02
$1,204,600
4
2
1,365
Off Market
35 Edgemoor Ave, Wellesley, MA 02482
0.02
$920,600
Studio
-
-
Off Market
40 Edgemoor Ave, Wellesley, MA 02482
0.03
-
-
-
-
Off Market
67 Overbrook Dr, Wellesley, MA 02482
0.03
$2,301,000
5
4.5
4,270
Off Market
33 Edgemoor Ave, Wellesley, MA 02482
0.03
$1,634,200
5
3.5
2,754
Off Market
38 Edgemoor Ave, Wellesley, MA 02482
0.03
$2,037,700
4
3.5
3,568
Off Market
36 Edgemoor Ave, Wellesley, MA 02482
0.04
$1,910,100
4
4
3,224
Off Market
4 High Ledge Ave, Wellesley, MA 02482
0.04
$1,648,600
3
1.5
2,096
Off Market
54 Overbrook Dr, Wellesley, MA 02482
0.04
$1,150,100
3
3
1,567
Off Market
18 High Ledge Ave, Wellesley, MA 02482
0.04
$1,629,400
3
2
1,781
Off Market
74 Overbrook Dr, Wellesley, MA 02482
0.04
$1,286,800
3
2
1,380
Off Market
32 Edgemoor Ave, Wellesley, MA 02482
0.04
$875,800
2
2
1,007
Off Market
56 Edgemoor Ave, Wellesley, MA 02482
0.04
$1,958,400
7
4.5
4,048
Off Market
10 Hillcroft Rd, Wellesley, MA 02482
0.05
$1,718,700
4
3
3,027
Off Market
51 Overbrook Dr, Wellesley, MA 02482
0.05
$2,194,600
4
3.5
3,699
Off Market
15 Upland Rd, Natick, MA 01760
0.05
$1,279,200
4
3
2,720
Off Market
27 Edgemoor Ave, Wellesley, MA 02482
0.05
$2,482,500
7
7
5,648
Off Market

Local Information

  • Map ViewExplore the area around 66 Overbrook Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2017
2,362 sqft
$819/sqft

About this House

NEW CONSTRUCTION! Come explore Wellesley's best value. Featuring 4 generous bedrooms and 3.5 baths with a perfect floor plan for today's active lifestyle. This beautiful home offers a chef's kitchen (Wolf & Subzero) and design features galore. The custom mudroom, master suite with a vaulted ceiling and luxurious master closet are just few of the special features of this ENERGY STAR home. During construction that special buyer is still able to customize. Come meet with the "Expert Construction Design Team" to make this home your own and pick your tile, countertops, lighting, paint colors, plumbing fixtures, and more. The design team will assist you in a streamlined selection process and walk you through all your choices OR simply let them create the perfect home with all their experience and expertise. Come enjoy the best Wellesley has to offer: Schools, Commute, Shopping and MUCH MORE....
66 Overbrook Dr, Wellesley, MA 02482 is a 4 bedroom, 4 bathroom, 2,362 sqft single-family home built in 2017. It last sold for $1,220,888 on Jan 18, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,934,600, with a rent estimate of $6,138/month.

Home Details for 66 Overbrook Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 2017
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Other

Community

Units in Building: 1

Lot Information

Lot Area: 6534 sqft

Price and Tax history

DateEventPrice
Jan 18, 2018
Source: N/A
Sold
$1,220,888
Apr 20, 2017
Source: N/A
Sold
$400,000

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 66 Overbrook Dr

  • What is 66 Overbrook Dr estimated to be worth?
    Trulia's estimated value for 66 Overbrook Dr in Wellesley, MA is $1,934,600.
  • What is the price history for 66 Overbrook Dr?
    66 Overbrook Dr in Wellesley, MA last sold for $1,220,888 in January 2018.
  • 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.
  • How big is the lot at 66 Overbrook Dr?
    The lot at 66 Overbrook Dr in Wellesley, MA is about 0.15 acres (6,534 sq ft).

Explore by feature - Pet Friendly

15 pet-friendly rentals in Wellesley, MA

Explore by feature - Garage

10 rentals with a garage in Wellesley, MA

Explore by feature - Air Conditioning

22 rentals with air conditioning in Wellesley, MA

Explore by feature - Washer/dryer

26 rentals with a washer/dryer in Wellesley, MA

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 66 Overbrook Dr

Skip to last item
Skip to first item

Homes for sale near 66 Overbrook Dr

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