66 Oak St, Wellesley, MA 02482
Property image
Property image
OFF MARKET

$2,303,100

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 3,195 sqft (on 0.32 acres)

66 Oak St, Wellesley, MA 02482

Est. Refi. Payment $13,727/mo*
Refinance Your Home
Currently Off Market - Sold Oct 12, 2021 for $2,035,000

Home Value

Trulia Estimate
$2.3M
Since last month
Decreased$55K (-2.3%)
Since last year
Decreased$23K (-1%)
Since last sale
Increased$264K (+13%)
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 +55% in the last 10 years
MonthEstimated value
2026
August 2026$2.3M
July 2026$2.35M
June 2026$2.36M
May 2026$2.39M
April 2026$2.37M
March 2026$2.35M
February 2026$2.28M
January 2026$2.25M
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 Ivy Rd, Wellesley, MA
0.21
Single-Family Home
$2,100,000
07/02/26
4
3
3,476
16 Oak St, Wellesley, MA
0.19
Single-Family Home
$2,480,000
07/06/26
5
4
4,200
70 Curve St, Wellesley, MA
0.33
Single-Family Home
$2,400,000
07/30/26
5
3.5
3,860
42 Calvin Rd, Wellesley, MA
0.36
Single-Family Home
$1,930,000
12/05/25
5
4
2,962
53 Audubon Rd, Wellesley, MA
0.48
Single-Family Home
$2,325,000
08/05/26
4
3.5
3,406
40 Pinewood Rd, Wellesley, MA
0.35
Single-Family Home
$1,800,000
04/09/26
4
2.5
2,334
14 Sunset Rd, Wellesley, MA
0.28
Single-Family Home
$1,530,000
10/24/25
3
2.5
2,652
21 Howe St, Wellesley, MA
0.36
Single-Family Home
$1,630,000
06/12/26
4
3
2,527
2 Summit Rd, Wellesley, MA
0.32
Single-Family Home
$2,560,000
10/14/25
4
4.5
3,693
81 Audubon Rd, Wellesley, MA
0.43
Single-Family Home
$2,300,000
04/07/26
5
3.5
3,985

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
63 Oak St #B, Wellesley, MA 02482
0.04
$1,600,000
3
3.5
2,377
Recently Sold
63 Oak St #A, Wellesley, MA 02482
0.04
$1,600,000
3
3.5
2,377
Recently Sold
58 Oak St #58, Wellesley, MA 02482
0.04
-
3
2.5
1,800
Off Market
74 Oak St, Wellesley, MA 02482
0.04
$2,606,300
5
4.5
6,085
Off Market
65 Pleasant St, Wellesley, MA 02482
0.05
$3,094,000
5
4.5
5,041
Off Market
62 Pleasant St, Wellesley, MA 02482
0.08
$1,384,800
2
2
1,260
Off Market
68 Pleasant St, Wellesley, MA 02482
0.08
$3,603,100
5
5.5
4,484
Off Market
26 Pleasant St #B, Wellesley, MA 02482
0.13
$1,019,999
2
2
1,739
For Sale
34 Pleasant St #3, Wellesley, MA 02482
0.13
$1,160,700
2
2.5
1,988
Off Market
31-31 Oak St #B, Wellesley, MA 02482
0.15
-
3
2
1,790
Off Market
34 Pleasant St #5, Wellesley, MA 02482
0.13
$1,400,000
3
3.5
2,100
Recently Sold
26-26B Pleasant St, Wellesley, MA 02482
0.14
-
2
2
1,837
Off Market

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
2006
Lot Size
0.32 acres
Living Area
3,195 sqft
Price/Sqft
$721

About this House

This single-family home is located at 66 Oak St, Wellesley, MA. 66 Oak St is in Wellesley, MA and in ZIP code 02482. This property has 4 bedrooms, 4 bathrooms and approximately 3,195 sqft of floor space. This property has a lot size of 0.32 acres and was built in 2006.
66 Oak St, Wellesley, MA 02482 is a 4 bedroom, 4 bathroom, 3,195 sqft single-family home built in 2006. It last sold for $2,035,000 on Oct 12, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,303,100, with a rent estimate of $7,942/month.

Home Details for 66 Oak St

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: 2006
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: 0.32 acres

Price and Tax history

DateEventPrice
Oct 12, 2021
Source: MLS PIN #72890850
Sold
$2,035,000
Sep 11, 2021
Source: MLS PIN #72890850
Pending
$1,875,000
Sep 8, 2021
Source: MLS PIN #72890850
Listed For Sale
$1,875,000
Mar 13, 2007
Source: N/A
Sold
$1,299,000
Jan 10, 1994
Source: N/A
Sold
$48,750

Market trends in Wellesley

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.15M
$161KMoM
Sale-to-List Price
100.6%
0.4%MoM
Price per sq ft
$666
$18MoM
Available listings
87
25MoM

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

Frequently asked questions about 66 Oak St

  • What is 66 Oak St estimated to be worth?
    Trulia's estimated value for 66 Oak St in Wellesley, MA is $2,303,100.
  • What is the price history for 66 Oak St?
    66 Oak St in Wellesley, MA last sold for $2,035,000 in October 2021.
  • 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.
  • How big is the lot at 66 Oak St?
    The lot at 66 Oak St in Wellesley, MA is about 0.32 acres (13,858 sq ft).

Explore by feature - Pet Friendly

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