OFF MARKET

Off Market Jan 2025 for $5.1M

$5,443,794

•

11,041

sq ft

165 Cliff Rd, Wellesley, MA 02481

About this home

This captivating Tudor blends timeless elegance w/modern sophistication redesigned by the renowned architect, Patrick Ahern. It's situated on nearly an acre of lush, pristine grounds in the prestigious Cliff Estates. The magnificent Carriage House w/a vaulted ceiling studio & bath offers the perfect work from home setting. A residence w/impressive sunlit formal rooms, handsome library w/a fireplace & inviting sunroom. The gorgeous Chef's Kitchen w/adjacent butler's pantry flows seamlessly into the Family Room. Double French doors opens to stone patios & fenced in play yard for fun & entertaining. 2nd floor w/4 en suite bdrms, including a luxurious Primary suite w/a spa-like bath & 3 closets. 3rd fl is dedicated to the ideal guest suite w/2 bedrooms, sitting room & bath. The LL is a true haven for leisure, w/it's spacious playroom, wine cellar, exercise room & billiard room w/ French doors leading to a blue stone patio. A special home, long admired & the one you've been waiting for!

Single-familyProperty Type

1930Year Built

0.9 acresLot Size

$493Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Patricia Bradley • Rutledge Properties

Bought with Susan Bevilacqua • Douglas Elliman Real Estate - Wellesley

Redfin checked: 2 minutes ago

•Source:MLS PIN #73297001

Redfin Estimate

$5,443,794

$294K since sold in January 2025$136K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 122.7% higher than the average sale price ($2.44M) of 6 comparable homes.

SOLD AUG 4, 2026
$2,315,000
A
4 beds3 baths4,799 sq ft
99 Parker Rd, Wellesley, MA 02482
SOLD JUL 31, 2026
$1,645,999
B
5 beds3.5 baths3,651 sq ft
30 Oakridge Ave, Natick, MA 01760
SOLD APR 1, 2026
$5,425,000
C
5 beds6.5 baths9,995 sq ft
192 Pond Rd, Wellesley, MA 02482
SOLD JUN 4, 2026
$2,350,000
D
5 beds6.5 baths5,000 sq ft
6 Briar Ln, Natick, MA 01760
SOLD JUN 17, 2026
$1,450,000
E
5 beds3.5 baths3,571 sq ft
10 Liberty St, Natick, MA 01760
SOLD JUL 30, 2026
$1,480,000
F
4 beds3 baths2,818 sq ft
7 Whitney Cir, Natick, MA 01760

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Earn from this home

Sell

$1,172,000

Est. take-home

List your home with Redfin and save $27,219

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 SAT, 11:30AM TO 1:30PM
$5,450,000
5 beds7 baths7,632 sq ft
44 Whiting Rd, Wellesley, MA 02481
$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 165 Cliff Rd

Date

Event

Price

MLS PIN #73297001

Jan 15, 2025

Sold

$5,150,000

$466/sq ft

Oct 17, 2024

Price Changed

$5,400,000

$489/sq ft

Oct 1, 2024

Listed

$5,600,000

$507/sq ft

MLS PIN #72479607

Jan 28, 2020

Sold

$3,600,000

$326/sq ft

Dec 20, 2019

Pending

—

Dec 6, 2019

Contingent

—

Nov 27, 2019

Relisted

—

Nov 21, 2019

Contingent

—

Nov 3, 2019

Price Changed

$3,975,000

$360/sq ft

Aug 18, 2019

Price Changed

$4,150,000

$376/sq ft

Jul 23, 2019

Price Changed

$4,475,000

$405/sq ft

Jul 23, 2019

Price Changed

$4,250,000

$385/sq ft

Jun 23, 2019

Price Changed

$4,475,000

$405/sq ft

Apr 10, 2019

Listed

$4,850,000

$439/sq ft

+24

Prestigious Cliff Estates residence is generously sited on just under an acre of land. This chic and sophisticated home, completely renovated in 2015, offers exquisite and timeless architectural detail throughout. Stunning foyer leads to grand living room with gorgeous beamed ceiling and classic dining room with lovely butler's pantry. Stunning chef's kitchen with high end appliances, custom hood and oversized island opens to sun-filled eat-in area and magnificent family room overlooking manicured grounds. Second floor offers luxurious master suite with serene spa like bath, three well proportioned bedrooms and two beautifully renovated full baths. Special space on the third floor with quiet sitting room and two bedrooms is the perfect spot to get away. Lower level includes exercise space, handsome billiard room, elegant wine cellar and gracious playroom. Fabulous carriage house with art studio and full bath offers a private retreat. Nothing has been spared - a truly amazing property

MLS PIN #71471886

Mar 14, 2014

Sold

$3,100,000

$281/sq ft

Feb 6, 2014

Contingent

—

Sep 9, 2013

Price Changed

$3,595,000

$326/sq ft

Jan 14, 2013

Listed

$3,995,000

$362/sq ft

+17

Elegant brick Tudor beautifully set on nearly an acre of land in sought after Cliff Estates offers extraordinary architectural detail and generously proportioned rooms perfect for both entertaining and everyday living. Features include grand foyer, gorgeous gourmet kitchen, 6 bedrooms in main house and walk out lower level which includes billiard room with wet bar, wine cellar, and workout room. Separate 4 room/2 bedroom Carriage House perfect for Au Pair or guest. Sun-filled and meticulous.

MLS PIN #30260723

Jun 29, 1999

Sold

$1,850,000

$168/sq ft

Feb 22, 1999

Listing Removed

—

Sep 21, 1998

Listed

$1,975,000

$179/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$46,476 (+0.2%)

$1,324,000 + $2,735,000

$4,059,000

2022

$46,405 (+0.6%)

$1,186,000 + $2,787,000

$3,973,000

2021

$46,107 (+1.6%)

$1,137,000 + $2,787,000

$3,924,000

2020

$45,361 (−3.9%)

$1,137,000 + $2,787,000

$3,924,000

2019

$47,206 (+4.4%)

$1,137,000 + $2,943,000

$4,080,000

2018

$45,219 (−5.2%)

$887,000 + $2,897,000

$3,784,000

2017

$47,691 (+25.5%)

$887,000 + $3,158,000

$4,045,000

2015

$38,009 (−1.5%)

$872,000 + $2,416,000

$3,288,000

2014

$38,601 (−17.1%)

$773,000 + $2,572,000

$3,345,000

2013

$46,543 (+1.9%)

$725,000 + $3,253,000

$3,978,000

2012

$45,667 (−0.5%)

$725,000 + $3,253,000

$3,978,000

2011

$45,891 (+8.0%)

$677,000 + $3,338,000

$4,015,000

2010

$42,486 (+10.1%)

$725,000 + $3,329,000

$4,054,000

2009

$38,581

$988,000 + $3,086,000

$4,074,000

Tax history for 165 Cliff Rd

Year

Property tax

Land + Additions

Assessment*

2023

$46,476 (+0.2%)

$1,324,000 + $2,735,000

$4,059,000

2022

$46,405 (+0.6%)

$1,186,000 + $2,787,000

$3,973,000

2021

$46,107 (+1.6%)

$1,137,000 + $2,787,000

$3,924,000

2020

$45,361 (−3.9%)

$1,137,000 + $2,787,000

$3,924,000

2019

$47,206 (+4.4%)

$1,137,000 + $2,943,000

$4,080,000

2018

$45,219 (−5.2%)

$887,000 + $2,897,000

$3,784,000

2017

$47,691 (+25.5%)

$887,000 + $3,158,000

$4,045,000

2015

$38,009 (−1.5%)

$872,000 + $2,416,000

$3,288,000

2014

$38,601 (−17.1%)

$773,000 + $2,572,000

$3,345,000

2013

$46,543 (+1.9%)

$725,000 + $3,253,000

$3,978,000

2012

$45,667 (−0.5%)

$725,000 + $3,253,000

$3,978,000

2011

$45,891 (+8.0%)

$677,000 + $3,338,000

$4,015,000

2010

$42,486 (+10.1%)

$725,000 + $3,329,000

$4,054,000

2009

$38,581

$988,000 + $3,086,000

$4,074,000

*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

—

Stories

—

Lot width

—

Lot depth

—

Lot size

0.9 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Norfolk County

APN

260316

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 20, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 3
# of Covered Spaces: 3
Parking Spaces: 10
Parking Features: Detached, Garage Door Opener, Heated Garage, Oversized, Paved Drive, Off Street, Driveway, Paved

Interior

Master Bedroom Information
Area: 352
Length: 22
Width: 16
Level: Second
Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Walk-In Closet(s),Closet,Flooring - Hardwood

Bedroom #2 Information
Area: 156
Length: 12
Width: 13
Level: Second
Features: Bathroom - Full,Closet,Flooring - Hardwood

Bedroom #3 Information
Area: 234
Length: 13
Width: 18
Level: Second
Features: Bathroom - Full,Closet,Flooring - Hardwood

Bedroom #4 Information
Area: 182
Length: 14
Width: 13
Level: Second
Features: Bathroom - Full,Closet,Flooring - Hardwood

Bedroom #5 Information
Area: 96
Length: 8
Width: 12
Level: Third
Features: Closet

Bathroom Information
# of Bathrooms (Full): 5
# of Bathrooms (Half): 3
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half

Bathroom #2 Information
Level: Second
Features: Bathroom - Full

Bathroom #3 Information
Level: Third
Features: Bathroom - Full

Living Room Information
Area: 416
Length: 26
Width: 16
Level: First
Features: Beamed Ceilings,Flooring - Hardwood,Exterior Access,Recessed Lighting,Sunken,Wainscoting,Lighting - Overhead

Family Room Information
Area: 361
Length: 19
Width: 19
Level: First
Features: Beamed Ceilings,Closet/Cabinets - Custom Built,Flooring - Hardwood,Exterior Access,Open Floorplan,Recessed Lighting

Dining Room Information
Area: 280
Length: 14
Width: 20
Level: First
Features: Flooring - Hardwood,Recessed Lighting,Lighting - Overhead

Kitchen Information
Area: 361
Length: 19
Width: 19
Level: First
Features: Flooring - Hardwood,Dining Area,Pantry,Kitchen Island,Cabinets - Upgraded,Exterior Access,Open Floorplan,Recessed Lighting,Lighting - Pendant

Office Room Information
Area: 176
Length: 11
Width: 16
Level: Main
Features: Ceiling - Vaulted,Closet/Cabinets - Custom Built,French Doors,Archway

Basement Information
Basement: Finished, Walk-Out Access, Sump Pump, Radon Remediation System

Laundry Information
Laundry Features: Countertops - Stone/Granite/Solid, In Basement

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 4
Fireplace Features: Living Room, Master Bedroom

Interior Features
# of Rooms (Total): 19
Door Features: French Doors
Window Features: Screens
Flooring: Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
Interior Features: Vaulted Ceiling(s), Closet/Cabinets - Custom Built, Archway, Beamed Ceilings, Recessed Lighting, Countertops - Stone/Granite/Solid, Wet Bar, Lighting - Pendant, Lighting - Sconce, Home Office, Study, Sun Room, Game Room, Exercise Room, Play Room, Wet Bar, Wired for Sound

Exterior

Building Information
Building Area (Total): 11,041
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Approximate

Exterior Features
Fencing: Fenced
Roof: Slate
Patio And Porch Features: Patio
Exterior Features: Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard, Fruit Trees, Stone Wall

Property Information
Accessibility Features: No
PropertySubType: Single Family Residence
Security Features: Security System

Lot Information
Lot Size (Acres): 0.9
Lot Features: Cleared, Level
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $47,449
Tax Year: 2024

Utilities

Utility Information
Utilities: for Gas Range
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Radiant, Natural Gas, Fireplace
Cooling: Central Air

Location

Location Information
Directions: Washington St to Cliff Road
UnparsedAddress: 165 Cliff Rd, Wellesley MA 02481

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Conservation Area

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 0.9 acres
Style: Other
Year Built: —
Year Renovated: —
County: Norfolk County
APN: 260316

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 5

Listing Information
StandardStatus: Closed

Around this home

Schools

Sprague Elementary School

Public K-5 • Assigned • 1.2mi

9/10

Wellesley Middle School

Public 6-8 • Assigned • 1.1mi

8/10

Wellesley High School

Public 9-12 • Assigned • 1.3mi

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

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$5.17M – $6.26M

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Nearby similar homes

OPEN SAT, 11:30AM TO 1:30PM

$5,450,000

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44 Whiting Rd, Wellesley, MA 02481

3D WALKTHROUGH

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OPEN SUN, 2PM TO 3:30PM

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3D WALKTHROUGH

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New listings for sale in 02481

OPEN SUN, 12PM TO 2PM

$3,595,000

6 beds5 baths6,525 sq ft

151 Oakland St, Wellesley, MA 02481

OPEN SAT, 11:30AM TO 1:30PM

$5,450,000

5 beds7 baths7,632 sq ft

44 Whiting Rd, Wellesley, MA 02481

$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 ACCESSCOMPASS COMING SOON

$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 ACCESSCOMPASS COMING SOON

$7,495,000

6 beds8 baths7,900 sq ft

38 Woodcliff Rd, Wellesley, MA 02481

Home values near 165 Cliff Rd

Data from public records.

Address	Redfin Estimate
146 Cliff Road, Wellesley, MA 6 Beds \| 5 Baths \| 4820 Sq. Ft.	$3,376,165
171 Cliff Road, Wellesley, MA 5 Beds \| 7 Baths \| 6000 Sq. Ft.	$3,643,530

Address	Redfin Estimate
164 Cliff Road, Wellesley, MA 5 Beds \| 6 Baths \| 6050 Sq. Ft.	$4,557,439
161 Cliff Road, Wellesley, MA 5 Beds \| 3.5 Baths \| 3224 Sq. Ft.	$2,845,022

Address	Redfin Estimate
175 Cliff Road, Wellesley, MA 4 Beds \| 3.5 Baths \| 3844 Sq. Ft.	$2,893,316
155 Cliff Road, Wellesley, MA 5 Beds \| 4 Baths \| 4996 Sq. Ft.	$3,550,930

Property information provided by MLS PIN when last listed in 2024. 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 165 Cliff Rd

Tax history for 165 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 165 Cliff Rd

More real estate resources