OFF MARKET

Off Market Aug 2020 for $8.7M

$9,896,183

Est. refi paymentEst. refi $28,642/mo

•

9,842

sq ft

209 Cliff Rd, Wellesley, MA 02481

About this home

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.

Single-familyProperty Type

1938Year Built

3.02 acresLot Size

$1,006Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Debi Benoit • Gibson Sotheby's International Realty

Bought with Debi Benoit • Gibson Sotheby's International Realty

Redfin checked: 3 minutes ago

•Source:MLS PIN #72676691

Redfin Estimate

$9,896,183

$1.1M since sold in August 2020$280K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 98.6% higher than the average sale price ($4.98M) of 6 comparable homes.

SOLD JUL 22, 2026
$6,100,000
A
6 beds7.5 baths10,197 sq ft
14 Greylock Rd, Wellesley, MA 02481
SOLD JUL 24, 2026
$5,500,000
B
5 beds5 baths6,203 sq ft
64 Albion Rd, Wellesley, MA 02481
SOLD JUL 27, 2026
$3,500,000
C
6 beds6.5 baths9,038 sq ft
100 Westcliff Rd, Weston, MA 02493
SOLD AUG 10, 2026
$4,593,250
D
7 beds6.5 baths8,840 sq ft
65 Woodcliff Rd, Wellesley, MA 02481
SOLD JUL 29, 2026
$4,950,000
E
5 beds6.5 baths9,200 sq ft
300 Glen Rd, Weston, MA 02493
SOLD JUN 15, 2026
$5,250,000
F
5 beds7 baths7,285 sq ft
22 Valley Rd, Wellesley, MA 02481

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Earn from this home

Sell

$3,238,728

Est. take-home

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Est. cash available

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Rent

$5,789/mo

Redfin rental estimate

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Market trends in 02481, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.8%

+0.1% MoM

Median sale price

$2.4M

$26K MoM

Avg. days on market

15d

0 days MoM

Recently sold homes

25 MoM

New listings for sale

OPEN SUN, 12PM TO 2PM
$3,595,000
6 beds5 baths6,525 sq ft
151 Oakland St, Wellesley, MA 02481
OPEN TODAY, 11:30AM TO 1:30PM
$5,450,000
5 beds7 baths7,632 sq ft
44 Whiting Rd, Wellesley, MA 02481
OPEN TODAY, 12PM TO 1:30PM
$4,695,000
6 beds4.5 baths7,013 sq ft
32 Arlington Rd, Wellesley, MA 02481
3D WALKTHROUGH
$1,395,000
4 beds2.5 baths1,800 sq ft
560 Worcester St, Wellesley, MA 02481
EARLY ACCESS
$2,049,000
3 beds3 baths4,366 sq ft
53 Sheridan Rd, Wellesley, MA 02481
$1,950,000
3 beds1.5 baths1,595 sq ft
53 Elmwood Rd, Wellesley, MA 02481
EARLY ACCESS
$7,495,000
6 beds8 baths7,900 sq ft
38 Woodcliff Rd, Wellesley, MA 02481
See all

Provided by Redfin

Sale history for 209 Cliff Rd

Date

Event

Price

MLS PIN #72676691

Aug 12, 2020

Sold

$8,750,000

$889/sq ft

Jun 20, 2020

Contingent

—

Jun 17, 2020

Listed

$8,995,000

$914/sq ft

MLS PIN #71200223

Apr 7, 2011

Sold

$6,800,000

$691/sq ft

Mar 24, 2011

Contingent

—

Mar 15, 2011

Listed

$7,995,000

$812/sq ft

Magnif, one-of-a-kind Cliff Estate/Farms Estate property.Incredible 3 acres of prof manicured grnds & specimen plntings w Swim Pool, Tennis Ct,& Tranq.Reflecting Pond. Renov.17 rm Estate. Eleg 2-story Foyer & Marble hallwys, 30ft LR w/Bay Window, Banquet DR w/arched corner cabs,Huge Gourmet Kit & Brkfst Rm adjac to light-filled FR, Gent's Bar, Ofc & frpld Lib. 5 large en-suite BRs, 3rd Fl. Suite. w LR, Kitchnette & 2 add. BRs. Incls sep. building lot. Rare opport. for discriminating buyer.

MLS PIN #70242813

Mar 24, 2006

Sold

$7,200,000

$732/sq ft

Aug 20, 2005

Listing Removed

—

Aug 16, 2005

Listed

$7,495,000

$762/sq ft

Surrounded by 3 acres of manicured grounds, tranquil pond, tennis court&pool, this 1938 brick Tudor located in the heart of the Cliff Estates was completely restored,rebuilt&expanded between 1989&2000.The residence has over 9,000 sqft of living space with a 2 story grand entry foyer,30 foot step down living room with carved oak walls, new kitchen and family room wing and expansive master suite.Showings to begin Friday 8/19/05

MLS PIN #50395634

Jul 31, 1998

Sold

$3,100,000

$315/sq ft

May 7, 1998

Listing Removed

—

Apr 14, 1998

Listed

$3,500,000

$356/sq ft

Public Records

Jun 1, 1992

Sold

$307,950

$31/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$78,742 (−6.5%)

$2,209,000 + $4,668,000

$6,877,000

2022

$84,213 (+0.5%)

$1,979,000 + $5,231,000

$7,210,000

2021

$83,754 (+21.7%)

$1,897,000 + $5,231,000

$7,128,000

2020

$68,805

$1,581,000 + $4,371,000

$5,952,000

2019

$68,865 (−2.0%)

$1,581,000 + $4,371,000

$5,952,000

2018

$70,266 (+1.3%)

$1,610,000 + $4,270,000

$5,880,000

2017

$69,337 (−13.5%)

$1,611,000 + $4,270,000

$5,881,000

2015

$80,169 (+4.0%)

$1,583,000 + $5,352,000

$6,935,000

2014

$77,122 (−10.7%)

$1,404,000 + $5,279,000

$6,683,000

2013

$86,405 (+1.9%)

$1,317,000 + $6,068,000

$7,385,000

2012

$84,780 (+4.0%)

$1,317,000 + $6,068,000

$7,385,000

2011

$81,484 (+14.1%)

$1,229,000 + $5,900,000

$7,129,000

2010

$71,390 (+10.5%)

$1,317,000 + $5,495,000

$6,812,000

2009

$64,633

$1,794,000 + $5,031,000

$6,825,000

Tax history for 209 Cliff Rd

Year

Property tax

Land + Additions

Assessment*

2023

$78,742 (−6.5%)

$2,209,000 + $4,668,000

$6,877,000

2022

$84,213 (+0.5%)

$1,979,000 + $5,231,000

$7,210,000

2021

$83,754 (+21.7%)

$1,897,000 + $5,231,000

$7,128,000

2020

$68,805

$1,581,000 + $4,371,000

$5,952,000

2019

$68,865 (−2.0%)

$1,581,000 + $4,371,000

$5,952,000

2018

$70,266 (+1.3%)

$1,610,000 + $4,270,000

$5,880,000

2017

$69,337 (−13.5%)

$1,611,000 + $4,270,000

$5,881,000

2015

$80,169 (+4.0%)

$1,583,000 + $5,352,000

$6,935,000

2014

$77,122 (−10.7%)

$1,404,000 + $5,279,000

$6,683,000

2013

$86,405 (+1.9%)

$1,317,000 + $6,068,000

$7,385,000

2012

$84,780 (+4.0%)

$1,317,000 + $6,068,000

$7,385,000

2011

$81,484 (+14.1%)

$1,229,000 + $5,900,000

$7,129,000

2010

$71,390 (+10.5%)

$1,317,000 + $5,495,000

$6,812,000

2009

$64,633

$1,794,000 + $5,031,000

$6,825,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

7.5

Stories

Lot width

—

Lot depth

—

Lot size

1.56 Acres

Year renovated

1999

Sq. Ft.

9,842

Year built

1938

Style

Single Family Residential

County

Middlesex County

APN

260944

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 31, 2025.

Property details

Parking

Parking Information
Has Garage
# of Garage Spaces: 3
# of Covered Spaces: 3
Parking Spaces: 10
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Storage, Off Street

Interior

Master Bedroom Information
Area: 529
Length: 23
Width: 23
Level: Second
Features: Bathroom - Full,Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Hardwood,Flooring - Marble,Double Vanity,Dressing Room,Recessed Lighting,Steam / Sauna,Crown Molding,Decorative Molding,Pocket Door,Tray Ceiling(s)

Bedroom #2 Information
Area: 240
Length: 16
Width: 15
Level: Second
Features: Bathroom - Full,Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Stone/Ceramic Tile,Flooring - Wall to Wall Carpet,Recessed Lighting,Crown Molding

Bedroom #3 Information
Area: 252
Length: 18
Width: 14
Level: Second
Features: Bathroom - Full,Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Stone/Ceramic Tile,Flooring - Wall to Wall Carpet,Recessed Lighting,Crown Molding

Bedroom #4 Information
Area: 304
Length: 16
Width: 19
Level: Second
Features: Bathroom - Full,Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Stone/Ceramic Tile,Flooring - Wall to Wall Carpet,Window(s) - Bay/Bow/Box,Recessed Lighting,Crown Molding

Bedroom #5 Information
Area: 350
Length: 14
Width: 25
Level: Second
Features: Bathroom - Full,Skylight,Walk-In Closet(s),Cedar Closet(s),Flooring - Stone/Ceramic Tile,Flooring - Wall to Wall Carpet,Recessed Lighting,Crown Molding

Bathroom Information
# of Bathrooms (Full): 6
# of Bathrooms (Half): 3
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half,Recessed Lighting,Crown Molding

Bathroom #2 Information
Level: First
Features: Bathroom - Half,Pocket Door

Bathroom #3 Information
Level: Basement
Features: Bathroom - Half,Recessed Lighting

Living Room Information
Area: 510
Length: 30
Width: 17
Level: Main,First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Recessed Lighting,Lighting - Overhead,Crown Molding,Decorative Molding

Family Room Information
Area: 552
Length: 23
Width: 24
Level: Main,First
Features: Coffered Ceiling(s),French Doors,Exterior Access,Recessed Lighting,Crown Molding

Dining Room Information
Area: 336
Length: 16
Width: 21
Level: Main,First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Recessed Lighting,Crown Molding,Decorative Molding

Kitchen Information
Area: 432
Length: 18
Width: 24
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Window(s) - Bay/Bow/Box,Dining Area,Countertops - Stone/Granite/Solid,Kitchen Island,Cabinets - Upgraded,Exterior Access,Recessed Lighting,Stainless Steel Appliances,Crown Molding,Tray Ceiling(s)

Office Room Information
Area: 112
Length: 8
Width: 14
Level: First
Features: Closet/Cabinets - Custom Built,Recessed Lighting,Crown Molding

Basement Information
Basement: Full, Partially Finished

Laundry Information
Laundry Features: Closet/Cabinets - Custom Built, Flooring - Hardwood, Crown Molding, First Floor, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 5
Fireplace Features: Family Room, Living Room, Bedroom

Interior Features
# of Rooms (Total): 16
Door Features: French Doors
Flooring: Tile, Carpet, Marble, Hardwood, Flooring - Hardwood, Flooring - Wall to Wall Carpet
Interior Features: Recessed Lighting, Crown Molding, Wet Bar, Cabinets - Upgraded, Closet/Cabinets - Custom Built, Cedar Closet(s), Closet, Library, Home Office, Exercise Room, Bedroom, Sauna/Steam/Hot Tub, Wet Bar, Wired for Sound

Exterior

Building Information
Building Area (Total): 9,842
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Actual

Exterior Features
Fencing: Fenced
Patio And Porch Features: Patio
Exterior Features: Patio, Pool - Inground, Pool - Inground Heated, Tennis Court(s), Rain Gutters, Hot Tub/Spa, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Garden

Pool Information
Has Private Pool
Has Spa
Pool Features: In Ground, Pool - Inground Heated
Spa Features: Private

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 3.02
Lot Features: Corner Lot
ViewYN: Has View
View: Scenic View(s)
Road Surface Type: Paved
Road Frontage Type: Public
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $82,840
Tax Year: 2020

Utilities

Utility Information
Utilities: for Gas Range, Washer Hookup, Icemaker Connection, Generator Connection
Sewer: Public Sewer
Water Source: Public
Electric: Generator, Generator Connection

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Natural Gas, Fireplace(s)
Cooling: Central Air

Location

Location Information
Directions: Cliff Road to White Oak (Entrance is located on White Oak Road)
UnparsedAddress: 209 Cliff Rd, Wellesley MA 02481

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Walk/Jog Trails, Conservation Area, Private School, Public School, University

Public facts

Beds: 7
Baths: 7.5
Sq. Ft.: 9,842
Stories: 3.0
Lot Size: 1.56 acres
Style: Single Family Residential
Year Built: 1938
Year Renovated: 1999
County: Middlesex County
APN: 260944

Home facts updated by county records on Jul 31, 2025

Other

Miscellaneous Information
Heat Zones: 7

Listing Information
Exclusions: Please See Listing Broker.
StandardStatus: Closed

Around this home

Schools

Sprague Elementary School

Public K-5 • Assigned • 1.3mi

9/10

Wellesley Middle School

Public 6-8 • Assigned • 1.3mi

8/10

Wellesley High School

Public 9-12 • Assigned • 1.6mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 97° expected this year, 15 days in 30 years

6/10 Wind Factor

54% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Wellesley, MA • 02481

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$9.40M – $11.38M

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EARLY ACCESSCOMPASS COMING SOON

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EARLY ACCESSCOMPASS COMING SOON

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Home values near 209 Cliff Rd

Data from public records.

Address	Redfin Estimate
88 Cliff Rd, Weston, MA 5 Beds \| 4 Baths \| 5930 Sq. Ft.	$4,366,515
199 Cliff Rd, Wellesley, MA 4 Beds \| 3.5 Baths \| 3044 Sq. Ft.	$2,375,389

Address	Redfin Estimate
100 Cliff Rd, Weston, MA 5 Beds \| 3.5 Baths \| 3122 Sq. Ft.	$2,219,319
195 Cliff Rd, Wellesley, MA 5 Beds \| 4 Baths \| 4097 Sq. Ft.	$3,233,459

Address	Redfin Estimate
205 Cliff Rd, Wellesley, MA 5 Beds \| 5 Baths \| 5300 Sq. Ft.	$4,379,134
194 Cliff Rd, Wellesley, MA 5 Beds \| 3.5 Baths \| 3409 Sq. Ft.	$4,081,577

Property information provided by MLS PIN when last listed in 2020. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 02481, MA

Sale history for 209 Cliff Rd

Tax history for 209 Cliff Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02481

Home values near 209 Cliff Rd

More real estate resources