OFF MARKET

Off Market Sep 2018 for $5M

$7,868,637

•

16,463

sq ft

99 Westcliff Rd, Weston, MA 02493

About this home

AUCTION: Bidding Open, Bidding Ends July 17 | Previously $4.95M, Without Reserve | Open Daily 1–4PM & by Appointment. Venture up the winding, uphill drive to get a glimpse of your grand 1920s English Tudor mansion. Occupying a place on the National Historic Register, Henderson House is rich with period design and exquisite detailing. Tailor-made for the gala of your dreams, this estate offers a large kitchen and prep space, coatroom, ballroom, banquet room, and a private guest floor. Feel like American royalty as you welcome guests to your hilltop mansion overlooking this beautiful slice of New England.

Single-familyProperty Type

1928Year Built

5.62 acresLot Size

$478Est. Price/Sq.Ft.

30 spacesParking

Listed by Debi Benoit • Benoit Mizner Simon & Co. - Wellesley - Central St

Bought with Alex Burke • Trove Properties

Redfin checked: 3 minutes ago

•Source:MLS PIN #71631176

Redfin Estimate

$7,868,637

$2.9M since sold in September 2018$591K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 57.9% 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 27, 2026
$3,500,000
B
6 beds6.5 baths9,038 sq ft
100 Westcliff Rd, Weston, MA 02493
SOLD AUG 10, 2026
$4,593,250
C
7 beds6.5 baths8,840 sq ft
65 Woodcliff Rd, Wellesley, MA 02481
SOLD JUL 29, 2026
$4,950,000
D
5 beds6.5 baths9,200 sq ft
300 Glen Rd, Weston, MA 02493
SOLD JUL 24, 2026
$5,500,000
E
5 beds5 baths6,203 sq ft
64 Albion Rd, Wellesley, MA 02481
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

$4,131,667

Est. take-home

List your home with Redfin and save $39,343

Rent

$4,951/mo

Redfin rental estimate

List your home for rent

Market trends in 02493, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.1%

1.1% MoM

Median sale price

$2.5M

$207K MoM

Avg. days on market

44d

16 days MoM

Recently sold homes

4 MoM

New listings for sale

OPEN SUN, 3PM TO 5PM
$2,075,000
4 beds2.5 baths3,340 sq ft
4 Cherry Brook Rd, Weston, MA 02493
OPEN SAT, 11:30AM TO 1:30PM
$4,288,000
4 beds3.5 baths6,442 sq ft
80 Doublet Hill Rd, Weston, MA 02493
NEW 25 HRS AGO
$2,495,000
4 beds4.5 baths5,446 sq ft
703 Boston Post Rd, Weston, MA 02493
OPEN SUN, 1PM TO 2:30PM
$3,695,000
4 beds5.5 baths5,126 sq ft
55 Oakdale Ave, Weston, MA 02493
$3,850,000
5 beds5.5 baths6,700 sq ft
21 Bemis St, Weston, MA 02493
OPEN SAT, 2:30PM TO 4PM
$1,250,000
3 beds2.5 baths2,460 sq ft
287 Glen Rd, Weston, MA 02493
$6,680,000
5 beds7.5 baths7,766 sq ft
25 Holly Cir, Weston, MA 02493
$6,695,000
6 beds7 baths9,500 sq ft
250 Country Dr, Weston, MA 02493
OPEN SAT, 12PM TO 1:30PM
$1,795,000
3 beds3 baths3,252 sq ft
120 Church St, Weston, MA 02493
$10,850,000
7 beds8.5 baths13,555 sq ft
15 Claridge Dr, Weston, MA 02493
See all

Provided by Redfin

Sale history for 99 Westcliff Rd

Year

Property tax

Land + Additions

Assessment*

2026

$68,386 (+0.8%)

$1,901,600 + $4,383,900

$6,285,500

2025

$67,853 (+3.2%)

$1,729,000 + $4,383,900

$6,112,900

2024

$65,761 (+4.3%)

$1,729,000 + $4,184,800

$5,913,800

2023

$63,056 (+4.3%)

$1,729,000 + $3,596,700

$5,325,700

2022

$60,462 (−2.1%)

$1,607,400 + $3,112,500

$4,719,900

2021

$61,729 (+1.2%)

$1,786,200 + $2,969,500

$4,755,700

2020

$61,016 (−22.2%)

$1,786,200 + $2,969,500

$4,755,700

2019

$78,437 (+0.6%)

$1,786,200 + $4,443,900

$6,230,100

2018

$77,939 (+0.9%)

$1,786,200 + $4,443,900

$6,230,100

2017

$77,253 (+2.0%)

$1,786,200 + $4,443,900

$6,230,100

2016

$75,758 (+1.0%)

$1,786,200 + $4,443,900

$6,230,100

2015

$74,999 (−6.8%)

$1,731,000 + $4,376,400

$6,107,400

2014

$80,466 (+3.3%)

$1,808,600 + $4,512,400

$6,321,000

2013

$77,904 (+3.5%)

$1,770,200 + $4,512,400

$6,282,600

2012

$75,302 (+10.7%)

$1,808,600 + $4,409,600

$6,218,200

2011

$68,007 (+2.1%)

$1,848,800 + $4,122,000

$5,970,800

2010

$66,616 (+0.7%)

$1,879,400 + $4,122,000

$6,001,400

2009

$66,135

$1,879,400 + $4,122,000

$6,001,400

Tax history for 99 Westcliff Rd

Year

Property tax

Land + Additions

Assessment*

2026

$68,386 (+0.8%)

$1,901,600 + $4,383,900

$6,285,500

2025

$67,853 (+3.2%)

$1,729,000 + $4,383,900

$6,112,900

2024

$65,761 (+4.3%)

$1,729,000 + $4,184,800

$5,913,800

2023

$63,056 (+4.3%)

$1,729,000 + $3,596,700

$5,325,700

2022

$60,462 (−2.1%)

$1,607,400 + $3,112,500

$4,719,900

2021

$61,729 (+1.2%)

$1,786,200 + $2,969,500

$4,755,700

2020

$61,016 (−22.2%)

$1,786,200 + $2,969,500

$4,755,700

2019

$78,437 (+0.6%)

$1,786,200 + $4,443,900

$6,230,100

2018

$77,939 (+0.9%)

$1,786,200 + $4,443,900

$6,230,100

2017

$77,253 (+2.0%)

$1,786,200 + $4,443,900

$6,230,100

2016

$75,758 (+1.0%)

$1,786,200 + $4,443,900

$6,230,100

2015

$74,999 (−6.8%)

$1,731,000 + $4,376,400

$6,107,400

2014

$80,466 (+3.3%)

$1,808,600 + $4,512,400

$6,321,000

2013

$77,904 (+3.5%)

$1,770,200 + $4,512,400

$6,282,600

2012

$75,302 (+10.7%)

$1,808,600 + $4,409,600

$6,218,200

2011

$68,007 (+2.1%)

$1,848,800 + $4,122,000

$5,970,800

2010

$66,616 (+0.7%)

$1,879,400 + $4,122,000

$6,001,400

2009

$66,135

$1,879,400 + $4,122,000

$6,001,400

*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

8.5

Stories

Lot width

—

Lot depth

—

Lot size

4.06 Acres

Year renovated

—

Sq. Ft.

14,587

Year built

1928

Style

Single Family Residential

County

Middlesex County

APN

1859659S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 10, 2026.

Property details

Parking

Parking Information
Has Open Parking
Parking Spaces: 30
Parking Features: Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Area: 484
Length: 22
Width: 22
Level: Second
Features: Bathroom - Full,Walk-In Closet(s),Flooring - Wall to Wall Carpet

Bedroom #2 Information
Area: 468
Length: 18
Width: 26
Level: Second
Features: Bathroom - Half,Closet,Flooring - Hardwood

Bedroom #3 Information
Area: 247
Length: 19
Width: 13
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #4 Information
Area: 255
Length: 17
Width: 15
Level: Second
Features: Bathroom - Full,Closet,Flooring - Hardwood

Bedroom #5 Information
Area: 380
Length: 19
Width: 20
Level: Second
Features: Closet,Flooring - Wall to Wall Carpet

Bathroom Information
# of Bathrooms (Full): 5
# of Bathrooms (Half): 4
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile

Bathroom #2 Information
Level: First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile

Bathroom #3 Information
Level: First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile,Handicap Accessible

Living Room Information
Area: 968
Length: 22
Width: 44
Level: Main,First
Features: Flooring - Hardwood

Family Room Information
Area: 961
Length: 31
Width: 31
Level: Main,First
Features: Flooring - Wall to Wall Carpet,Window(s) - Picture

Dining Room Information
Area: 540
Length: 18
Width: 30
Level: Main,First
Features: Flooring - Hardwood,Window(s) - Picture

Kitchen Information
Area: 280
Length: 14
Width: 20
Level: Main,First
Features: Pantry,Storage

Basement Information
Basement: Partially Finished

Laundry Information
Laundry Features: Flooring - Stone/Ceramic Tile, Washer Hookup, Second Floor

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 8
Fireplace Features: Dining Room, Living Room, Master Bedroom

Interior Features
# of Rooms (Total): 25
Door Features: French Doors
Flooring: Tile, Carpet, Hardwood, Flooring - Hardwood
Interior Features: Open Floorplan, Closet, Bathroom - Full, Entrance Foyer, Study, Sitting Room, Bedroom

Exterior

Building Information
Building Area (Total): 16,463
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Actual
Color: Beige

Exterior Features
Roof: Slate, Rubber
Patio And Porch Features: Patio
Exterior Features: Patio, Professional Landscaping, Decorative Lighting, Stone Wall

Property Information
PropertySubType: Single Family Residence
Security Features: Security System

Lot Information
Lot Size (Acres): 5.62
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: $77,938.55
Tax Year: 2018

Utilities

Utility Information
Utilities: for Gas Range, Washer Hookup
Sewer: Private Sewer
Water Source: Public

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

Location

Location Information
Directions: Cliff Road to Scotch Pine to Westcliff
UnparsedAddress: 99 Westcliff Road, Weston MA 02493

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

Public facts

Beds: 9
Baths: 8.5
Sq. Ft.: 14,587
Stories: 3.0
Lot Size: 4.06 acres
Style: Single Family Residential
Year Built: 1928
Year Renovated: —
County: Middlesex County
APN: 1859659S

Home facts updated by county records on Aug 10, 2026

Other

Miscellaneous Information
Heat Zones: 9

Listing Information
Exclusions: Please See Listing Broker
StandardStatus: Closed

Around this home

Schools

Field Elementary School

Public 4-5 • Assigned • 2.6mi

8/10

Weston Middle School

Public 6-8 • Assigned • 1.1mi

9/10

Weston High School

Public 9-12 • Assigned • 1.1mi

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

4/10 Heat Factor

7 days above 97° expected this year, 14 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

Weston, MA • 02493

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

$7.48M – $9.05M

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New listings for sale in 02493

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Home values near 99 Westcliff Rd

Data from public records.

Address	Redfin Estimate
77 Westcliff Road, Weston, MA 5 Beds \| 7 Baths \| 7399 Sq. Ft.	$4,793,658
100 Westcliff Road, Weston, MA 6 Beds \| 6.5 Baths \| 9038 Sq. Ft.	$4,619,236

Address	Redfin Estimate
70 Westcliff Road, Weston, MA 6 Beds \| 4.5 Baths \| 5560 Sq. Ft.	$4,205,705
104 Westcliff Road, Weston, MA 5 Beds \| 5.5 Baths \| 4832 Sq. Ft.	$4,222,699

Address	Redfin Estimate
80 Westcliff Road, Weston, MA 5 Beds \| 4.5 Baths \| 4474 Sq. Ft.	$3,379,222
70 Westcliff Road, Weston, MA 6 Beds \| 4.5 Baths \| 4995 Sq. Ft.	$3,647,837

Property information provided by MLS PIN when last listed in 2014. This data may not match . Learn more.

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