OFF MARKET

Off Market Aug 2016 for $2.2M

$3,252,567

Est. refi paymentEst. refi $1,637/mo

•

5,129

sq ft

21 Cypress Rd, Wellesley, MA 02481

About this home

Newly renovated and expanded in highly sought after Cliff Estates this sun filled and thoughtfully designed home has it all. Open floorplan includes chef's kitchen w/Thermador Professional appliances, marble countertops w/an oversized center island. Beautiful fireplaced family room. Breakfast room with custom built-in seating. Oversized dining room, walk in pantry and butler's pantry w/wine fridge and 2nd dishwasher are perfect for entertaining. Opulent and private master suite boasts sitting area, fireplace, spa like bath w/ separate sun filled makeup area separate his & hers closets. Add'l 4 bedrooms, 2 full baths & laundry room w/storage complete 2nd floor. Third floor is a finished open space perfect for au pair suite, gaming/homework area or second office. Lower level features a finished playroom & storage. Large, grassy just completed yard, professional landscaping, large patio w/outdoor speakers & natural gas for grill. Smart home technology, 5 zones heating/ac. Walk to train

Single-familyProperty Type

1914Year Built

0.43 acresLot Size

$634Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Katherine Canavan • Keller Williams Realty

Bought with Kathy Kelley • Berkshire Hathaway HomeServices Town and Country Real Estate

Redfin checked: 3 minutes ago

•Source:MLS PIN #72028704

Redfin Estimate

$3,252,567

$1.0M since sold in August 2016$55K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1.8% higher than the average sale price ($3.19M) of 6 comparable homes.

SOLD AUG 14, 2026
$3,900,000
A
5 beds3.5 baths5,074 sq ft
33 Hundreds Cir, Wellesley, MA 02481
SOLD JUL 7, 2026
$3,200,000
B
5 beds4.5 baths4,010 sq ft
101 Edmunds Rd, Wellesley, MA 02481
SOLD JUL 22, 2026
$4,400,000
C
5 beds4.5 baths4,628 sq ft
133 Abbott Rd, Wellesley, MA 02481
SOLD JUL 16, 2026
$2,690,000
D
4 beds3.5 baths4,761 sq ft
21 Elm St, Wellesley, MA 02481
SOLD JUN 26, 2026
$2,525,000
E
4 beds3.5 baths3,497 sq ft
35 Arnold Rd, Wellesley, MA 02481
SOLD MAY 6, 2026
$2,450,000
F
5 beds3.5 baths3,369 sq ft
40 Chestnut St, Wellesley, MA 02481

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$1,674,370

Est. take-home

List your home with Redfin and save $16,263

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$5,728/mo

Redfin rental estimate

List your home for rent

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
OPEN SAT, 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 21 Cypress Rd

Date

Event

Price

MLS PIN #72028704

Aug 31, 2016

Sold

$2,250,000

$439/sq ft

Jul 8, 2016

Pending

—

Jun 23, 2016

Listed

$2,195,000

$428/sq ft

MLS PIN #71301295

Dec 1, 2011

Sold

$830,000

$162/sq ft

Oct 24, 2011

Contingent

—

Oct 17, 2011

Listed

$895,000

$174/sq ft

+13

The location speaks for itself! Wonderful opportunity to restore, renovate or expand this unspoiled 1915 Arts & Crafts inspired Colonial set amongst lovely homes of higher supporting value in prestigious "Old Cliff Estates" neighborhood. Designed by prominent Harvard University Architect/Professor, William Luther Mowll, this lovingly maintained home offers high ceilings, two fireplaces and a three season porch overlooking lovely gardens. Second floor art studio was used as a 4th bedroom.

Public Records

Aug 31, 1995

Sold

$260,000

$51/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$25,808 (+5.9%)

$967,000 + $1,287,000

$2,254,000

2022

$24,376 (+1.1%)

$867,000 + $1,220,000

$2,087,000

2021

$24,099 (+1.6%)

$831,000 + $1,220,000

$2,051,000

2020

$23,710

$831,000 + $1,220,000

$2,051,000

2019

$23,730 (−8.7%)

$831,000 + $1,220,000

$2,051,000

2018

$25,979 (+18.0%)

$875,000 + $1,299,000

$2,174,000

2017

$22,024 (−1.3%)

$874,000 + $994,000

$1,868,000

2016

$22,311 (+21.5%)

$860,000 + $1,026,000

$1,886,000

2015

$18,357 (+2.8%)

$860,000 + $728,000

$1,588,000

2014

$17,864 (+37.2%)

$686,000 + $862,000

$1,548,000

2013

$13,022 (+27.7%)

$643,000 + $470,000

$1,113,000

2012

$10,194 (+1.7%)

$643,000 + $245,000

$888,000

2011

$10,024 (+1.1%)

$622,000 + $255,000

$877,000

2010

$9,914 (−0.4%)

$691,000 + $255,000

$946,000

2009

$9,953

$826,000 + $225,000

$1,051,000

Tax history for 21 Cypress Rd

Year

Property tax

Land + Additions

Assessment*

2023

$25,808 (+5.9%)

$967,000 + $1,287,000

$2,254,000

2022

$24,376 (+1.1%)

$867,000 + $1,220,000

$2,087,000

2021

$24,099 (+1.6%)

$831,000 + $1,220,000

$2,051,000

2020

$23,710

$831,000 + $1,220,000

$2,051,000

2019

$23,730 (−8.7%)

$831,000 + $1,220,000

$2,051,000

2018

$25,979 (+18.0%)

$875,000 + $1,299,000

$2,174,000

2017

$22,024 (−1.3%)

$874,000 + $994,000

$1,868,000

2016

$22,311 (+21.5%)

$860,000 + $1,026,000

$1,886,000

2015

$18,357 (+2.8%)

$860,000 + $728,000

$1,588,000

2014

$17,864 (+37.2%)

$686,000 + $862,000

$1,548,000

2013

$13,022 (+27.7%)

$643,000 + $470,000

$1,113,000

2012

$10,194 (+1.7%)

$643,000 + $245,000

$888,000

2011

$10,024 (+1.1%)

$622,000 + $255,000

$877,000

2010

$9,914 (−0.4%)

$691,000 + $255,000

$946,000

2009

$9,953

$826,000 + $225,000

$1,051,000

*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

0.43 Acres

Year renovated

2012

Sq. Ft.

5,129

Year built

1914

Style

Single Family Residential

County

Norfolk County

APN

260373

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: 3
AttachedGarageYN: Yes
Parking Features: Attached, Workshop in Garage, Insulated, Paved Drive, Off Street

Interior

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 2

Basement Information
Basement: Full, Partially Finished

Laundry Information
Laundry Features: Electric Dryer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 3

Interior Features
# of Rooms (Total): 10
Window Features: Insulated Windows
Flooring: Wood, Tile, Marble, Hardwood
Interior Features: Walk-Up Attic, Wired for Sound

Exterior

Building Information
Building Area (Total): 5,129
Foundation Details: Concrete Perimeter, Stone
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Renovated Since
Color: Gray

Exterior Features
Roof: Shingle
Patio And Porch Features: Patio, Covered
Exterior Features: Patio, Covered Patio/Deck, Rain Gutters, Professional Landscaping, Sprinkler System

Property Information
PropertySubType: Single Family Residence
Green Energy Efficient : Thermostat
Security Features: Security System

Lot Information
Lot Size (Acres): 0.43
Lot Features: Wooded, Level
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $22,311
Tax Year: 2016

Utilities

Utility Information
Utilities: for Gas Range, for Gas Oven, for Electric Dryer
Sewer: Public Sewer
Water Source: Public
Electric: 110 Volts, 200+ Amp Service

Heating & Cooling
Has Heating
Has Cooling
Heating: Natural Gas, Hydro Air
Cooling: Central Air

Location

Location Information
Directions: Washington Street to Cliff Road to Cypress Road
UnparsedAddress: 21 Cypress Rd, Wellesley MA 02481

Community Information
Senior CommunityYN: No
Community Features: Public Transportation

Public facts

Beds: 5
Baths: 4.0
Sq. Ft.: 5,129
Stories: 2.0
Lot Size: 0.43 acres
Style: Single Family Residential
Year Built: 1914
Year Renovated: 2012
County: Norfolk County
APN: 260373

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 • 1.1mi

9/10

Wellesley Middle School

Public 6-8 • Assigned • 0.9mi

8/10

Wellesley High School

Public 9-12 • Assigned • 1.0mi

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

$3.09M – $3.74M

Reach more buyers when you sell with Redfin. Save up to $32,526 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

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

$5,450,000

5 beds7 baths7,632 sq ft

44 Whiting Rd, Wellesley, MA 02481

$2,725,000

5 beds5.5 baths3,954 sq ft

45 Clearwater Rd, Newton, MA 02462

$4,995,000

6 beds5 baths7,738 sq ft

43 Monadnock Rd, Wellesley, MA 02481

OPEN SUN, 2PM TO 3:30PM

$2,449,000

4 beds3.5 baths4,201 sq ft

283 Walnut St, Wellesley, MA 02481

$5,395,000

Land— sq ft

475 Glen Rd, Weston, MA 02493

OPEN SUN, 2:15PM TO 3:30PM

$2,825,000

5 beds5.5 baths5,172 sq ft

265 Weston Rd, Wellesley, MA 02482

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

OPEN SAT, 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 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 21 Cypress Rd

Data from public records.

Address	Redfin Estimate
12 Cypress Rd, Wellesley, MA 5 Beds \| 3.5 Baths \| 3390 Sq. Ft.	$2,551,528
37 Cypress Rd, Wellesley, MA 6 Beds \| 7.5 Baths \| 7932 Sq. Ft.	$6,222,906

Address	Redfin Estimate
8 Cypress Rd, Wellesley, MA 5 Beds \| 2.5 Baths \| - Sq. Ft.	$1,813,876
25 Cypress Rd, Wellesley, MA 5 Beds \| 3.5 Baths \| 3532 Sq. Ft.	$2,314,592

Address	Redfin Estimate
43 Cypress Rd, Wellesley, MA 4 Beds \| 3 Baths \| 1934 Sq. Ft.	$4,104,759
17 Cypress Rd, Wellesley, MA 4 Beds \| 3.5 Baths \| 2599 Sq. Ft.	$2,430,768

Property information provided by MLS PIN when last listed in 2016. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

02030 homes for sale
02481 homes for sale
02492 homes for sale
02493 homes for sale
01760 homes for sale

Houses for rent in Wellesley	Agents near me	Quincy, MA homes for sale	Wellesley Housing Market
Houses for sale near me	Boston, MA homes for sale	Brookline, MA homes for sale
Land for sale near me	Newton, MA homes for sale	Arlington, MA homes for sale
Open Houses near me	Cambridge, MA homes for sale	Wellesley Property Records
Condos for sale near me	Lexington, MA homes for sale	MA New Listings

Cambridge homes for sale
Boston homes for sale
Newton homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 02481, MA

Sale history for 21 Cypress Rd

Tax history for 21 Cypress 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 21 Cypress Rd

More real estate resources