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50 Winsor WayWeston, MA 02493

For Sale

$16,900,000

Smart Buyer Rebate $84,500

A true showcase luxury gated estate, 50 Winsor Way is situated on over 2 acres of elevated and private land located off the Weston Golf Club. The estate features truly picturesque professionally landscaped grounds, expansive terraces and patios with views for entertaining, and a large showpiece swimming pool and patio with elegant fountains. 50 Winsor boasts more than 6 bedrooms including the luxurious main level master suite, 7 full bathrooms, 3 half bathrooms, and an expansive 4-car garage. Designed by Thoughtforms, this home boasts an expansive open floor plan and luxurious craftmanship and attention to detail throughout. The fully finished lower level is equipped with a recreation room, wine cellar, full theater room, wet bar, steam room, and sauna. On the second floor, four bedrooms offer private en suite bathrooms. This exceptional home is a unique grand colonial estate for the discerning buyer set in one of the most highly desired locations in all of Weston

Last updated September 03, 2026

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Source: MLSPin #73550581

Listing Facts

  • TypeSingle-family
  • NeighborhoodWeston
  • Bedrooms6
  • Bathrooms10
  • Days on Prevu61
  • Taxes$144,088/year
  • Size10,116 sqft
  • Price per sqft$1,671

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking
  • Swimming Pool

Location

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Listing History

07/16/2026
Listed by
$16,900,000
  1. 07/16/2026$16,900,000
    Listed by

Property Details for 50 Winsor Way

Association

Amenities

  • Community Features: Pool, Tennis Court(s), Golf

Exterior

Construction

  • Roof: Wood
  • Window Features: Insulated Windows, Screens, Bay Window(s)
  • Year Built: 2004
  • Year Built Details: Actual
  • Architectural Style: Colonial
  • Construction Materials: Frame
  • Exterior Features: Balcony, Rain Gutters, Lighting

Features

  • Fencing: Fenced, Stone
  • Patio And Porch Features: Patio
  • Pool Features: In Ground, Heated, Private
  • Pool Private: Yes
  • Road Frontage Type: Private Road
  • View: Scenic

Measurements

  • Building Area Total: 10,116
  • Building Area Units: Square Feet
  • Lot Features: Landscaped
  • Lot Size Acres: 2.02
  • Lot Size Area: 2
  • Lot Size Square Feet: 87,878
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:028.0 L:0063 S:000.0,867981
  • Tax Annual Amount: $144,088.00
  • Tax Assessed Value: $13,243,400.00
  • Tax Year: 2026

Interior

Features

  • Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
  • Fireplace Features: Family Room, Living Room, Master Bedroom
  • Fireplace: Yes
  • Fireplaces Total: 4
  • Flooring: Tile, Carpet, Hardwood
  • Interior Features: Recessed Lighting, Coffered Ceiling(s), Master Downstairs, Walk-In Closet(s), Open Floorplan

Measurements

  • Living Area: 10,116
  • Living Area Source: Public Records

Rooms

  • Basement: Full, Finished, Interior Entry
  • Has Basement: Yes
  • Bathrooms Full: 7
  • Bathrooms Half: 3
  • Bathrooms Total Integer: 10
  • Bedrooms Total: 6
  • Main Level Bathrooms: 1
  • Main Level Bedrooms: 1
  • Rooms Total: 17

Other

Environmental

  • Green Energy Efficient: Thermostat

Parking

Parking

  • Attached Garage: Yes
  • Covered Spaces: 4
  • Garage Spaces: 4
  • Garage: Yes
  • Open Parking Spaces: 15
  • Open Parking: Yes
  • Parking Features: Paved, Attached, Garage Door Opener, Heated Garage, Storage, Off Street, Driveway, Garage
  • Parking Total: 19

Schools

Elementary School

  • Elementary School: Weston Elem

High School

  • High School: Weston Hs

Middle or Junior School

  • Middle Or Junior School: Weston Ms

Utilities

Equipment

  • Cooling: Central Air, Zoned
  • Has Cooling: Yes
  • Electric: Generator
  • Heating: Natural Gas, Central, Forced Air, Zoned
  • Has Heating: Yes
  • Laundry Features: Electric Dryer Hookup, Washer Hookup
  • Sewer: Private Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 6 bedrooms and 10 bathrooms in this single-family home at 50 Winsor Way.

What schools are nearby to 50 Winsor Way?

Nearby schools include the Weston Elem Elementary School, Weston Ms Middle School, and Weston Hs High School.

Does this single-family home have parking?

Yes, there are 4 parking spaces available for 50 Winsor Way.

What are the annual taxes for 50 Winsor Way?

Annual taxes for this single-family home are estimated at $144,088.

How does 50 Winsor Way compare to other single-family homes in Weston?

This single-family home is listed 229% above the average price for single-family homes in Weston and has been on the market for 33 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 10,116 sqft.

50 Winsor Way is a 6-bedroom, 10-bath single-family home for sale in Weston MA 02493. Listed on Prevu for 61 days at $16,900,000. This residence features 10,116 square feet of living space, located in Weston. The median listing price for single-family homes in this area is $3,722,500. Nearby schools include Weston Elem Elementary School, Weston Ms Middle School, and Weston Hs High School. The home offers private outdoor space, dishwasher, air conditioning, parking, swimming pool, and washer/dryer. Browse more single-family home listings in Middlesex County.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. 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, leasing or renting 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, leasing or renting. MLS Property Information Network, Inc. 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.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.