8 Oakcliff Rd, Wellesley, MA 02481
Property image
Property image
OFF MARKET

$2,720,700

Trulia Estimate
  • 5 Beds
  • 4 Baths
  • 2,505 sqft (on 0.58 acres)

8 Oakcliff Rd, Wellesley, MA 02481

Est. Refi. Payment $16,203/mo*
Refinance Your Home
Currently Off Market - Sold Jun 27, 2003 for $1,200,000

Home Value

Trulia Estimate
$2.72M
Since last month
Decreased$36K (-1.3%)
Since last year
Increased$200K (+8%)
Since last sale
Increased$1M (+123.7%)
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 +61% in the last 10 years
MonthEstimated value
2026
August 2026$2.68M
July 2026$2.72M
June 2026$2.75M
May 2026$2.75M
April 2026$2.64M
March 2026$2.65M
February 2026$2.51M
January 2026$2.53M
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
33 Hundreds Cir, Wellesley, MA
0.30
Single-Family Home
$3,900,000
08/14/26
5
3.5
5,074
70 Old Farm Rd, Wellesley, MA
0.21
Single-Family Home
$2,842,000
10/15/25
2
2
3,736
101 Edmunds Rd, Wellesley, MA
0.45
Single-Family Home
$3,200,000
07/07/26
5
4.5
4,010
26 White Oak Rd, Wellesley, MA
0.13
Single-Family Home
$4,558,000
10/14/25
5
5
6,160
69 Royalston Rd, Wellesley, MA
0.56
Single-Family Home
$3,100,000
07/10/26
5
3.5
3,805
8 Old Town Rd, Wellesley, MA
0.72
Single-Family Home
$1,975,000
01/06/26
5
4
2,614
40 Chestnut St, Wellesley, MA
0.56
Single-Family Home
$2,450,000
05/06/26
5
3.5
3,369
54 Colburn Rd, Wellesley, MA
0.68
Single-Family Home
$1,655,000
01/30/26
4
2.5
2,204
3 Ravine Rd, Wellesley, MA
0.21
Single-Family Home
$4,750,000
05/11/26
5
7
7,720
56 Ledgeways, Wellesley, MA
0.17
Single-Family Home
$4,400,000
12/01/25
6
8
7,000

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
45 White Oak Rd, Wellesley, MA 02481
0.09
$10,995,000
5
5.5
7,200
For Sale
184 Cliff Rd, Wellesley, MA 02481
0.07
-
6
7
14,663
Off Market
26 White Oak Rd, Wellesley, MA 02481
0.13
-
5
5
6,160
Off Market
200 Cliff Rd, Wellesley, MA 02481
0.11
$5,100,000
7
6
7,262
For Sale
56 White Oak Rd, Wellesley, MA 02481
0.12
$4,028,200
5
4.5
4,309
Off Market
165 Cliff Rd, Wellesley, MA 02481
0.10
-
6
6.5
11,041
Off Market
56 Ledgeways, Wellesley, MA 02481
0.17
$4,400,000
6
8
7,000
Recently Sold
55 Old Farm Rd, Wellesley, MA 02481
0.20
$6,530,800
6
9
8,211
Off Market
65 Woodcliff Rd, Wellesley, MA 02481
0.19
$4,593,250
7
6.5
8,840
Recently Sold
70 Old Farm Rd, Wellesley, MA 02481
0.21
-
2
2
3,736
Off Market
3 Ravine Rd, Wellesley, MA 02481
0.21
$4,750,000
5
7
7,720
Recently Sold
11 Greylock Rd, Wellesley, MA 02481
0.24
$5,250,800
4
6
7,408
Off Market

Local Information

  • Map ViewExplore the area around 8 Oakcliff Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1965
Lot Size
0.58 acres
Living Area
2,505 sqft
Price/Sqft
$1,086

About this House

Immaculate, executive quality five bedroom home nestled in top notch Cliff Estates/ Wellesley Farms neighborhood. Great kitchen with new stainless appliances and five burner stove. Generous room sizes. Finished lower level with play room and game room. Enjoy summer nights on the beautiful screen porch overlooking the huge, private fenced yard. This classic home is sited among some of Wellesley's largest and priciest properties. Oversized, level and landscaped grounds offer loads of space to expand or showcase your ultimate dream home. Popular Sprague Elementary School.
8 Oakcliff Rd, Wellesley, MA 02481 is a 5 bedroom, 4 bathroom, 2,505 sqft single-family home built in 1965. It last sold for $1,200,000 on Jun 27, 2003. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,720,700, with a rent estimate of $7,571/month.

Home Details for 8 Oakcliff Rd

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 10
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Exterior Features

Exterior Home Features
Exterior: Wood

Community

Units in Building: 1

Lot Information

Lot Area: 0.58 acres

Price and Tax history

DateEventPrice
Jul 16, 2014
Source: Agent Provided
ListingRemoved
$1,995,000
Jun 24, 2014
Source: Agent Provided
Listed For Sale
$1,995,000
Jun 27, 2003
Source: N/A
Sold
$1,200,000

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 8 Oakcliff Rd

  • What is 8 Oakcliff Rd estimated to be worth?
    Trulia's estimated value for 8 Oakcliff Rd in Wellesley, MA is $2,720,700.
  • What is the price history for 8 Oakcliff Rd?
    8 Oakcliff Rd in Wellesley, MA last sold for $1,200,000 in June 2003.
  • 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 8 Oakcliff Rd?
    The lot at 8 Oakcliff Rd in Wellesley, MA is about 0.58 acres (25,264 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 8 Oakcliff Rd

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