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50 Winsor Way

Weston, MA 02493

Offered at$16,900,000

Residential · Active · MLS #73550581
Listing Courtesy of Blue Ocean Realty, LLC | Rose Hall

6Bedrooms
10Bathrooms
10,116Square feet
2004Year built

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MLS PIN data

About this home

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

Property information

Details at a glance

Interior

Rooms
17
Heating
Central, Forced Air, Natural Gas, Fireplace
Cooling
Central Air
Flooring
Tile, Carpet, Hardwood, Stone / Slate, Flooring - Hardwood, Flooring - Wall to Wall Carpet, Flooring - Stone/Ceramic Tile
Fireplaces
4

Building

Style
Single Family Residence
Year built
2004
Garage
4
Parking
19
Foundation
Concrete Perimeter
Roof
Wood

Land & utilities

Lot size
2.02 acres
Water
Public
Sewer
Private Sewer
Zoning
RES

Financial

Annual taxes
$144,088
Assessment year
2026

Listing history

Price and status timeline

  1. New

    $60,000 · Jun 7, 2026

  2. Ter

    $14,900,000 · Aug 12, 2024

Property value estimate

An informed starting point

Estimated value$9,288,450

Estimated range $8,178,289$10,398,611

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Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Recent comparable sales are not available for this property.

Photo insights

Condition signals

Overall presentationexcellent

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Weston

MetricThis propertyWeston
List price$16,900,000$3,695,000357% above local
Price / sq ft$1,671$692141% above local
Days on market47695% below local
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Active city listing statistics from MLS PIN as of September 6, 2026. Asking prices are not completed-sale values.

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Common questions

About 50 Winsor Way

Can I schedule a private showing?

Yes. Request a tour of 50 Winsor Way and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.