209 Cliff Rd, Wellesley, MA 02481
Property image
Property image
OFF MARKET

$11,571,400

Trulia Estimate
  • 7 Beds
  • 7.5 Baths
  • 9,842 sqft (on 3.02 acres)

209 Cliff Rd, Wellesley, MA 02481

Est. Refi. Payment $68,788/mo*
Refinance Your Home
Currently Off Market - Sold Aug 12, 2020 for $8,750,000

Home Value

Trulia Estimate
$11.6M
Since last month
Decreased$23K (-0.2%)
Since last year
Increased$424K (+3.8%)
Since last sale
Increased$3M (+32.2%)
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 +83% in the last 10 years
MonthEstimated value
2026
August 2026$11.57M
July 2026$11.59M
June 2026$11.62M
May 2026$11.57M
April 2026$11.39M
March 2026$11.15M
February 2026$10.91M
January 2026$11.02M
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
184 Cliff Rd, Wellesley, MA
0.17
Single-Family Home
$14,750,000
09/30/25
6
7
14,663
300 Glen Rd, Weston, MA
0.27
Single-Family Home
$4,950,000
07/29/26
5
6.5
9,200
14 Greylock Rd, Wellesley, MA
0.16
Single-Family Home
$6,100,000
07/22/26
6
7.5
10,197
100 Westcliff Rd, Weston, MA
0.29
Single-Family Home
$3,500,000
07/27/26
6
6.5
9,038
65 Woodcliff Rd, Wellesley, MA
0.25
Single-Family Home
$4,593,250
08/10/26
7
6.5
8,840
26 White Oak Rd, Wellesley, MA
0.11
Single-Family Home
$4,558,000
10/14/25
5
5
6,160
52 Valley Rd, Wellesley, MA
0.59
Single-Family Home
$9,275,000
07/07/26
7
8
11,124
48 Scotch Pine Rd, Wellesley, MA
0.33
Single-Family Home
$5,200,000
06/25/26
5
4.5
7,345
3 Ravine Rd, Wellesley, MA
0.36
Single-Family Home
$4,750,000
05/11/26
5
7
7,720
64 Albion Rd, Wellesley, MA
0.43
Single-Family Home
$5,500,000
07/24/26
5
5
6,203

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
200 Cliff Rd, Wellesley, MA 02481
0.09
$5,100,000
7
6
7,262
For Sale
11 Greylock Rd, Wellesley, MA 02481
0.12
$5,250,800
4
6
7,408
Off Market
26 White Oak Rd, Wellesley, MA 02481
0.11
$4,729,800
5
5
6,160
Off Market
14 Greylock Rd, Wellesley, MA 02481
0.16
$6,100,000
6
7.5
10,197
Recently Sold
73 Greylock Rd, Wellesley, MA 02481
0.19
$2,448,900
4
3
4,133
Off Market
184 Cliff Rd, Wellesley, MA 02481
0.17
$15,290,300
6
7
14,663
Off Market
45 White Oak Rd, Wellesley, MA 02481
0.20
$10,995,000
5
5.5
7,200
For Sale
25 Cliff Rd, Weston, MA 02493
0.28
-
7
6.5
6,830
Off Market
300 Glen Rd, Weston, MA 02493
0.27
$4,950,000
5
6.5
9,200
Recently Sold
56 White Oak Rd, Wellesley, MA 02481
0.25
$4,006,600
5
4.5
4,309
Off Market
45 Cliff Rd, Weston, MA 02493
0.29
$3,620,900
5
3.5
3,828
Off Market
100 Westcliff Rd, Weston, MA 02493
0.29
$3,500,000
6
6.5
9,038
Recently Sold

Local Information

  • Map ViewExplore the area around 209 Cliff Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1938
Lot Size
3.02 acres
Living Area
9,842 sqft
Price/Sqft
$1,176
Parking
Garage

About this House

Welcome to 209 Cliff Road. Once in a while a magical property comes on the market that wows at every turn. Tucked away and beautifully sited on acres of impressive professionally landscaped grounds created by the Olmsted Brothers in the 1930s, this spectacular home is set amidst rolling lawns and gardens. Features outside include a spa like swimming pool, tranquil reflecting pond with stone bridge, tennis court, and inside soaring ceilings and fine custom details from beginning to end! An estate like this in the desirable Wellesley Farms is truly a once in a lifetime opportunity. This exceptional property combined with the adjoining lot, 12 White Oak Road, provides endless possibilities. This spectacular Wellesley Farms opportunity also includes .93 acres of accessory land abutting this property in Weston. Impeccable craftsmanship and unparalleled quality are found throughout this magnificent and prestigious estate. Available for private tours only. PPE required at all showings.
209 Cliff Rd, Wellesley, MA 02481 is a 7 bedroom, 9 bathroom, 9,842 sqft single-family home built in 1938. It last sold for $8,750,000 on Aug 12, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $11,571,400, with a rent estimate of $6,787/month.

Home Details for 209 Cliff Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Carpet, Hardwood
Interior Details
Number of Rooms: 14
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa

Property Information

Year Built
Year Built: 1938Year Updated: 1999
Property Type / Style
Property Type: Single Family HomeArchitecture: Tudor

Exterior Features

Exterior Home Features
Exterior: BrickPatioSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 3.02 acres

Building

Pool
Sauna
Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Aug 12, 2020
Source: N/A
Sold
$8,750,000
Jun 20, 2020
Source: Agent Provided
Pending
$8,995,000
Jun 18, 2020
Source: Agent Provided
Listed For Sale
$8,995,000
Mar 26, 2011
Source: Agent Provided
ListingRemoved
$7,995,000
Jan 15, 2011
Source: Agent Provided
PriceChange
$7,995,000
Price decreased by 24%

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 209 Cliff Rd

  • What is 209 Cliff Rd estimated to be worth?
    Trulia's estimated value for 209 Cliff Rd in Wellesley, MA is $11,571,400.
  • What is the price history for 209 Cliff Rd?
    209 Cliff Rd in Wellesley, MA last sold for $8,750,000 in August 2020.
  • 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.
  • Does 209 Cliff Rd have air conditioning?
    Yes, 209 Cliff Rd in Wellesley, MA has air conditioning.
  • Does 209 Cliff Rd have a pool?
    Yes, 209 Cliff Rd in Wellesley, MA has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

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Off Market Homes Near 209 Cliff Rd

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