Last Sold Price
4 beds6,376 sqft$179/sqft
33 Winston Rd, Holliston, MA 01746

Description

Every once in a while, an exquisite and unique property becomes available. This lush 2.7 acre property includes 2 separate 3 car garages, custom built annex off the master suite with a balcony overlooking the pool. This stunningly built home offers an exceptional combination of high-quality details and charming features that will capture you right away. Three levels of luxury living, including a large kitchen with a screened in porch all viewing the inground pool, 2 beautiful office's, one with a...Every once in a while, an exquisite and unique property becomes available. This lush 2.7 acre property includes 2 separate 3 car garages, custom built annex off the master suite with a balcony overlooking the pool. This stunningly built home offers an exceptional combination of high-quality details and charming features that will capture you right away. Three levels of luxury living, including a large kitchen with a screened in porch all viewing the inground pool, 2 beautiful office's, one with a warming fireplace and the other with built-ins and a wet bar. Very spacious bedrooms each with large closets and all hardwood floors. This private oasis is perfect for the car enthusiasts, home business owners or simply those that relish both privacy & beauty. offered as an estate sale. This could be that diamond in the rough at the end of a cul-de-sac you have been looking for!
LISTING CLOSED: 11/23/2021 12:00 AM

  1. Listed by The Results Team • RE/MAX Executive Realty
  2. Listed by Robert Black • RE/MAX Executive Realty

Property Details for 33 Winston Road

Status
MLS #
72882731
Days on Market
49
Taxes
$25,565 / year
HOA Fees
-
Property Type
MLS Type
Single Family / Detached
Year Built
1988
Town
Holliston
Area
MA-Holliston
Architectural Style
Colonial, Contemporary
Style
Colonial, Contemporary
Garage Spaces
6
Open Parking Spaces
4.00
Parking Spaces Total
4

Recent comparable sales

Median sold price

$1,260,000

Avg days on market

29

Sale-to-list ratio

100.4%

Holliston, MA

9 comparable properties found

$1,350,000 | 457 Hanlon Road, Holliston, MA 01746
1/43
1

$1,350,000

Sold 06/26/26

4
Bedrooms
5,860
Square Feet
1.00
Acres
a front view of a house with garden
1/41
2

$1,215,000

Sold 04/14/25

4
Bedrooms
4,914
Square Feet
1.27
Acres
a view of a house with yard and trees in the background
1/43
3

$1,300,000

Sold 08/28/25

4
Bedrooms
5,356
Square Feet
0.89
Acres
$1,292,500 | 45 Johnson Drive, Holliston, MA 01746
1/40
4

$1,292,500

Sold 08/14/26

4
Bedrooms
4,198
Square Feet
2.85
Acres
a front view of a house with a yard
1/37
5

$1,260,000

Sold 10/21/24

5
Bedrooms
5,134
Square Feet
1.4
Acres
a front view of a house with a garden
1/2
6

$1,690,000

Sold 05/28/26

5
Bedrooms
6,498
Square Feet
1.2
Acres
$999,999 | 79 Marshall Street, Holliston, MA 01746
1/43
7

$999,999

Sold 07/01/26

4
Bedrooms
3,752
Square Feet
2.07
Acres
a aerial view of a house next to a big yard and large trees
1/43
8

$1,049,900

Sold 09/05/25

4
Bedrooms
2,578
Square Feet
0.92
Acres
$940,000 | 62 Ridge Road, Holliston, MA 01746
1/30
9

$940,000

Sold 02/21/25

4
Bedrooms
2,607
Square Feet
0.42
Acres

Location

Listing Courtesy of RE/MAX Executive Realty, The Results Team; RE/MAX Executive Realty, Robert Black

Sold By Cali Realty Group, Inc., Joseph Cali

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Building Information for 33 Winston Road

Stories-Year Built1988Building Size-Lot Size2.70 AC / 117,656 SF

Payment Calculator

$7,925 per month

30 year fixed, 6.55% Interest

Principal and Interest

$5,794

Property Taxes

$2,130

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 33 Winston Road

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Shopping, Park, Walk/Jog Trails, Golf Course, Bike Path, Public School
  • Current Financing: Conv. Fixed
  • Living Area: 6376.0
  • Color: White
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Water View: No
  • Year Built Details: Actual
  • Year Built Source: Public Records
Location/School
  • Grade School: Miller School
  • High School: Holliston
  • Middle School: Robert H Adams
Features
Interior Features
  • Appliances: Range, Dishwasher, Disposal, Refrigerator, Oil Water Heater, Utility Connections for Electric Range, Utility Connections for Electric Oven
  • Basement Features: Full, Finished, Partially Finished, Walk Out, Interior Access
  • Num of Baths: 5.0
  • Num of Full Baths: 3
  • Num of Half Baths: 2
  • Bathrooms Total Decimal: 4.00
  • Bathrooms Total Integer: 5
  • DoorFeatures: Insulated Doors, French Doors
  • FireplaceFeatures: Living Room
  • FireplaceYN: Yes
  • Fireplaces: 3
  • Flooring: Tile, Concrete, Hardwood, Stone / Slate, Flooring - Stone/Ceramic Tile, Flooring - Hardwood
  • Interior Features: Wet bar, Slider, Closet - Walk-in, Bathroom - Full, Office, Entry Hall, Home Office, Bathroom, Central Vacuum, Sauna/Steam/Hot Tub, Wetbar, Internet Available - Unknown
  • Interior Features: Central Vacuum, Sauna/Steam/Hot Tub, Wetbar, Internet Available - Unknown, French Doors, Intercom, Security System
  • Laundry Features: Flooring - Stone/Ceramic Tile, Second Floor, Washer Hookup
  • Other Equipment: Intercom
  • Primary Bath: Yes
  • Window Features: Insulated Windows, Screens
Exterior Features
  • Construction: Frame
  • Exterior Features: Balcony / Deck, Balcony, Rain Gutters, Storage Shed, Professional Landscaping, Sprinkler System
  • Exterior Features: Fenced Yard, Pool - Inground, Screens, Cabana, Balcony, Storage Shed, Professional Landscaping, Sprinkler System, Porch, Deck, Deck - Roof, Deck - Composite, Porch - Enclosed
  • Fencing: Fenced/Enclosed, Fenced
  • Lot Description: Cul-De-Sac, Wooded, Gentle Sloping, Level
  • Other Structures: Cabana
  • Patio And Porch Features: Deck - Exterior, Porch, Deck, Deck - Roof, Deck - Composite, Enclosed
  • Pool Features: In Ground
  • Pool Private: Yes
  • Roof Material: Shingle
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 6.00
  • Garage: Yes
  • Garage Parking: Attached, Under, Garage Door Opener, Heated, Storage, Work Area, Side Entry, Paved Drive, Off-Street, Improved Driveway, Paved Driveway
  • Open Parking: Yes
  • Parking Features: Attached, Under, Garage Door Opener, Heated, Storage, Work Area, Side Entry, Paved Drive, Off-Street, Improved Driveway, Paved Driveway
  • Parking Features: Heated, Work Area, Side Entry, Off-Street, Improved Driveway, Paved Driveway
Utilities
  • Cooling: Central Air, 3 or More
  • Cooling: Yes
  • Electric: 110 Volts, 220 Volts, Circuit Breakers
  • Green Energy Efficient: Thermostat
  • Heating: Baseboard, Oil, Fireplace
  • Heating: Yes
  • Sewer: Private Sewerage
  • Utility Connections: for Electric Range, for Electric Oven, Washer Hookup
  • Water: Public
Room Information
Primary Bedroom
  • Room Primary Bedroom Area: 266.0
  • Room Primary Bedroom Features: Flooring - Hardwood
  • Room Primary Bedroom Length: 14.0
  • Primary Bedroom Level: Second Floor
  • Room Primary Bedroom Width: 19.0
Bedroom 2
  • Bedroom2 Area: 196.0
  • Bedroom2 Features: Flooring - Hardwood
  • Bedroom2 Length: 14.0
  • Bedroom2 Level: Second
  • Bedroom2 Width: 14.0
Bedroom 3
  • Bedroom3 Area: 168.0
  • Bedroom3 Features: Flooring - Hardwood
  • Bedroom3 Length: 14.0
  • Bedroom3 Level: Second
  • Bedroom3 Width: 12.0
Bedroom 4
  • Bedroom4 Area: 196.0
  • Bedroom4 Features: Flooring - Hardwood
  • Bedroom4 Length: 14.0
  • Bedroom4 Level: Second
  • Bedroom4 Width: 14.0
Bedroom 5
  • Bedroom5 Features: Flooring - Hardwood
Bathroom 1
  • Bathroom1 Area: 42.0
  • Bathroom1 Features: Bathroom - Full,Flooring - Stone/Ceramic Tile
  • Bathroom1 Length: 6.0
  • Bathroom1 Level: First
  • Bathroom1 Width: 7.0
Bathroom 2
  • Bathroom2 Area: 169.0
  • Bathroom2 Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Bathroom - Tiled With Shower Stall,Bathroom - Tiled With Tub,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile
  • Bathroom2 Length: 13.0
  • Bathroom2 Level: Second
  • Bathroom2 Width: 13.0
Bathroom 3
  • Bathroom3 Area: 140.0
  • Bathroom3 Features: Bathroom - Full,Flooring - Stone/Ceramic Tile
  • Bathroom3 Length: 14.0
  • Bathroom3 Level: Second
  • Bathroom3 Width: 10.0
Dining Room
  • Dining Room Area: 196.0
  • Dining Room Features: Flooring - Hardwood
  • Dining Room Length: 14.0
  • Dining Room Level: First
  • Dining Room Width: 14.0
Family Room
  • Family Room Area: 280.0
  • Family Room Features: Flooring - Hardwood
  • Family Room Length: 14.0
  • Family Room Level: First
  • Family Room Width: 20.0
Kitchen
  • Kitchen Area: 392.0
  • Kitchen Features: Flooring - Stone/Ceramic Tile,Exterior Access,Peninsula
  • Kitchen Length: 28.0
  • Kitchen Level: Main
  • Kitchen Width: 14.0
Laundry
  • Laundry Dimen: 16X14
Living Room
  • Room Living Room Area: 368.0
  • Room Living Room Features: Flooring - Hardwood,Cable Hookup
  • Room Living Room Length: 16.0
  • Room Living Room Level: Main
  • Room Living Room Width: 23.0
Other Room 1
  • Room Office Area: 266.0
  • Room Office Features: Flooring - Stone/Ceramic Tile,Wet bar
  • Room Office Length: 14.0
  • Room Office Level: First
  • Room Office Width: 19.0
Property Information
Property Info
  • UFFI: No
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • Lot Size Units: Acres
  • Road Frontage Type: Public, Dead End
  • Road Responsibility: Public Maintained Road
  • Road Surface Type: Paved
  • Disclosures: Large basement with jacuzzi/steam room along with additional storage
Tax Information
  • Tax ID: M:007 B:0006 L:0810,523851
  • Assessments: $1,432,200
  • Book: 20334
  • Tax Year: 2021
  • Zoning: CL8
Building / Association Information
Living Characteristics
  • Beds Total: 4
Other Building Characteristics
  • Accessibility Features: Accessible Entrance
  • Foundation: Concrete Perimeter
  • Foundation Area: 0.0
  • Cooling Zones: 4
  • Heat Zones: 6
Complex & Association Information
  • Association Security: Security System
Market and Agent Information
Sale Info
  • Buyer Broker Comp: 2.5
  • Other Agent Compensation: 0

Property History for 33 Winston Road

DateEvent & SourcePriceAppreciation
Nov 23, 2021

Sold

MLS PIN #72882731

$1,140,000
Sep 18, 2021

Under Agreement

MLS PIN #72882731

Sep 18, 2021

Contingent

MLS PIN #72882731

DateEvent & SourcePrice
11/23/2021

Sold

MLS PIN #72882731

$1,140,000
09/18/2021

Under Agreement

MLS PIN #72882731

09/18/2021

Contingent

MLS PIN #72882731

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 33 Winston Road

Taxable ValueLand$320,000Additions$1,261,900Total$1,581,900
Tax Record2025$23,175 ($1,931 / month)
Home Facts
Beds4Baths4Total Finished SqFt6,376 SqFtAbove Grade Finished SqFt6,376 SqFtStories2Lot Size117,612 SqFtStyleSingle Family ResidenceYear Built1988Year Renovated1998ZoningCL8CountyMIDDLESEXAPNHOLL M:007 B:0006 L:0810

Schools near 33 Winston Road

This home is within Holliston School District.
Rating
School
Type
Grades
Distance
Public - PK to 2
Public - 3 to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Placentino Elementary School
PublicPK to 2

Miller School
Public3 to 5

Robert H. Adams Middle School
Public6 to 8

Holliston High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 33 Winston Road, Holliston, MA 01746
$1,140,000
4
6,376
117,656
$795,000
4
4,139
145,055
$760,000
4
3,148
57,064
17,860
$1,215,000
4
4,914
55,321
$58,500
5
2.5
2,376
50,530

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of RE/MAX Executive Realty, The Results Team; RE/MAX Executive Realty, Robert Black

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.