8 Oakcliff Rd, Wellesley, MA 02481
OFF MARKET

8 Oakcliff Rd
Wellesley, MA 02481

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

$2,724,600

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $16,011/mo*
Refinance Your Home

$2,724,600

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $16,011/mo*
Refinance Your Home
5 Beds
4 Baths
2,505 sqft
(on 0.58 acres)

Local Information

Map showing home location
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Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 8 Oakcliff Rd

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
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 History for 8 Oakcliff Rd

DatePriceEventSource
07/16/2014$1,995,000ListingRemovedAgent Provided
06/24/2014$1,995,000Listed For SaleAgent Provided
06/27/2003$1,200,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$21,084
Assessment$2,051,000
Home facts updated by county records

Comparable Sales for 8 Oakcliff Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
288 Glen Rd, Weston, MA
0.35
Single-Family Home
$1,200,000
08/27/25
5
3.5
2,864
73 Greylock Rd, Wellesley, MA
0.31
Single-Family Home
$2,380,000
08/05/25
4
3
4,133
81 Garden Rd, Wellesley, MA
0.58
Single-Family Home
$1,875,000
06/19/25
5
3
3,217
70 Old Farm Rd, Wellesley, MA
0.21
Single-Family Home
$2,842,000
10/15/25
2
2
3,736
36 Old Farm Rd, Wellesley, MA
0.30
Single-Family Home
$3,475,000
07/31/25
5
5.5
5,359
12 Cypress Rd, Wellesley, MA
0.47
Single-Family Home
$2,610,000
06/02/25
5
3.5
3,390
26 White Oak Rd, Wellesley, MA
0.13
Single-Family Home
$4,558,000
10/14/25
5
5
6,160
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
110 Hampshire Rd, Wellesley, MA
0.67
Single-Family Home
$2,875,000
05/28/25
5
3.5
3,829

Nearby homes

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Assigned Schools

These are the assigned schools for 8 Oakcliff Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Wellesley

At least 123 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

  • 76 % 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

  • 62 % 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
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8 Oakcliff Rd, Wellesley, MA 02481 is a 5 bedroom, 4 bathroom, 2,505 sqft single-family home built in 1965. This property is not currently available for sale. 8 Oakcliff Rd was last sold on Jun 27, 2003 for $1,200,000. The current Trulia Estimate for 8 Oakcliff Rd is $2,724,600.