Google satellite image for 33 Winston Rd, Holliston, MA 01746

Off market jan 1990 for $510K

$1,774,539

Est. refi paymentEst. refi $3,297/mo

•

4 ba

•

6,376

sq ft

33 Winston Rd, Holliston, MA 01746

About this home

33 Winston Rd is a 6,376 square foot house on a 2.7 acre lot with 4 bedrooms and 4 bathrooms. - it last sold on January 19, 1990 for $510,000. Based on Redfin's Holliston data, we estimate the home's value is $1,774,539.

Single-familyProperty Type

1988Year Built

2.7 acresLot Size

$278Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,774,539

$1.3M since sold in January 1990$13K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 18.3% higher than the average sale price ($1.50M) of 6 comparable homes.

SOLD AUG 14, 2026
$1,292,500
A
4 beds3.5 baths4,198 sq ft
45 Johnson Dr, Holliston, MA 01746
SOLD SEP 18, 2026
$1,350,000
B
4 beds2.5 baths4,382 sq ft
14 Hidden Brick Rd, Hopkinton, MA 01748
SOLD SEP 9, 2026
$1,147,500
C
4 beds3 baths3,648 sq ft
10 Winston Rd, Holliston, MA 01746
SOLD SEP 10, 2026
$1,200,000
D
4 beds4 baths3,982 sq ft
10 N Mill St, Hopkinton, MA 01748
SOLD AUG 7, 2026
$1,712,500
E
4 beds4.5 baths5,487 sq ft
7 S Barn Rd, Hopkinton, MA 01748
SOLD JUN 25, 2026
$2,300,000
F
4 beds5 baths6,472 sq ft
7 Pendulum Pass, Hopkinton, MA 01748

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Earn from this home

Sell

$1,685,593

Est. take-home

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Est. cash available

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Rent

$4,329/mo

Redfin rental estimate

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Market trends in 01746, MA

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

100.8%

1.1% MoM

Median sale price

$785K

$40K MoM

Avg. days on market

21d

1 days MoM

Recently sold homes

5 MoM

New listings for sale

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LISTED BY REDFIN
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741 Winter St, Holliston, MA 01746
OPEN SAT, 12PM TO 2PM
$899,000
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See all

Provided by Redfin

Sale history for 33 Winston Rd

Tax history for 33 Winston Rd

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

Property details

Interior

Basement Information
Basement Type: Full

Bathroom Information
# of Full Baths: 3
# of 1/2 Baths: 2

Heating & Cooling
Heating Type: Forced Hot Water

Fireplace Information
# of Fireplaces: 3
Has Fireplace

Room Information
# of Rooms: 15

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Colonial
Construction Type: Concrete
Exterior Wall: Aluminum/Vinyl
Roof Shape Type: Gable

Pool Information
Has Pool

Property Information
Living Sq. Ft: 6,376
Gross Sq. Ft: 7,539
Ground Floor Sq. Ft: 2,563
# of Units: 1
# of Stories: 2

Parking & Garage Information
Parking Type: Attached Garage
Garage / Carport Type: Attached

Lot Information
# of Buildings: 1
Land Sq. Ft: 117,612
Municipality Name: HOLLISTON
Acres: 2.7
Zoning Code: CL8
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 4
Baths: 4.0
Sq. Ft.: 6,376
Stories: 2.0
Lot Size: 2.7 acres
Style: Single Family Residential
Year Built: 1988
Year Renovated: 1998
County: Middlesex County
APN: 1612153S

Home facts updated by county records on Sep 11, 2026

Around this home

Schools

Placentino Elementary School

Public PreK-2 • Assigned • 3.0mi

Robert H. Adams Middle School

Public 6-8 • Assigned • 2.9mi

8/10

Holliston High School

Public 9-12 • Assigned • 2.0mi

9/10

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, 15 days in 30 years

6/10 Wind Factor

50% 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

Holliston, MA • 01746

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

$1.69M – $2.04M

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Nearby similar homes

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Expansive backyard • Screened porch • Updated kitchen

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3D WALKTHROUGH

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New listings for sale in 01746

OPEN SUN, 1PM TO 3PM

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Updated kitchen • Open floor plan • Huge walk in closets

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Expansive backyard • Screened porch • Updated kitchen

LISTED BY REDFIN3D WALKTHROUGH

$729,900

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Two skylights • Gas fireplace • Hardwood floors

$1,499,900

4 beds3.5 baths4,226 sq ft

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Built in cabinetry • Gas fireplace • 0.93 acre lot

$650,000

3 beds2 baths2,009 sq ft

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2.73 acre lot • Large flat yard • Versatile floor plan

OPEN SAT, 12PM TO 2PM

$899,000

5 beds3 baths2,908 sq ft

1419 Washington St, Holliston, MA 01746

Private deck • Dishwasher • Large driveway

$1,025,000

4 beds2.5 baths3,203 sq ft

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Farmer's porch • Quartz countertops • Center island

OPEN SAT, 11AM TO 12:30PM3D WALKTHROUGH

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3 beds2.5 baths2,724 sq ft

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Open concept • Great room • Skylights

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In law setup • Paver patio • Pool house

Home values near 33 Winston Rd

Data from public records.

Address	Redfin Estimate
10 Winston Rd, Holliston, MA 4 Beds \| 3 Baths \| 3648 Sq. Ft.	$1,207,080
30 Winston Rd, Holliston, MA 4 Beds \| 3 Baths \| 3148 Sq. Ft.	$1,055,469

Address	Redfin Estimate
25 Winston Rd, Holliston, MA 4 Beds \| 2.5 Baths \| 4139 Sq. Ft.	$1,328,357
11 Winston Rd, Holliston, MA 5 Beds \| 2.5 Baths \| 2376 Sq. Ft.	$997,101

Address	Redfin Estimate
22 Winston Rd, Holliston, MA 4 Beds \| 4 Baths \| 4914 Sq. Ft.	$1,387,235
25 Winston Rd, Holliston, MA 4 Beds \| 2.5 Baths \| 4139 Sq. Ft.	$1,356,169

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