Active
56 Days on market
50 Winsor Way Weston — Photo 1 of 35

50 Winsor Way Weston — Photo 1 of 35

$16,900,000

50 Winsor Way, Weston, MA 02493

Weston, MA 02493

Beds

6

Baths

8.5

SqFt

10,116

Style

Single Family

Built

2004

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

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$1671/sqft
Local Avg (Weston)$735/sqft
127% AboveMarket Average

* Analysis is based on 22 actively listed and recently sold comparable properties strictly within Weston, MA.

Property Details

Financials

Original Price$16,900,000
Annual Taxes$144,088

Parking

Garage4
Off-Street19

Interior Specifications

Total Rooms17
Fireplaces4
FlooringTile, Carpet, Hardwood, Stone / Slate, Flooring - Hardwood, Flooring - Wall to Wall Carpet, Flooring - Stone/Ceramic Tile
BasementFull, Finished, Interior Entry

Climate & Utilities

HeatingCentral, Forced Air, Natural Gas, Fireplace
CoolingCentral Air
WaterPublic
SewerPrivate Sewer

Building & Exterior

ConstructionFrame
RoofWood
FoundationConcrete Perimeter
ZoningRES

Property & Lot

Acres2.02
SqFt Lot87,878
Lot Features--

Amenities & Appliances

Gas Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator • Washer • Dryer

Neighborhood

Pool • Tennis Court(s) • Walk/Jog Trails • Golf • Bike Path • Conservation Area

Geography

Floorplan Breakdown

Structural Layout

Second
Bedroom 2Bedroom 3Bedroom 4Bedroom 5Bathroom 2
First
KitchenBathroom 1
Main,First
Living RoomDining RoomFamily RoomMaster BedroomBathroom 3
Main
Office
Living Room
Lvl Main,First

Flooring - Hardwood, Window(s) - Picture, Open Floorplan, Recessed Lighting, Wainscoting, Lighting - Overhead, Decorative Molding

Dining Room
Lvl Main,First

Closet, Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Window(s) - Picture, Breakfast Bar / Nook, Recessed Lighting, Decorative Molding

Kitchen
Lvl First

Coffered Ceiling(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Picture, Countertops - Stone/Granite/Solid, French Doors, Breakfast Bar / Nook, Cabinets - Upgraded, Exterior Access, Open Floorplan, Recessed Lighting, Second Dishwasher, Stainless Steel Appliances, Half Vaulted Ceiling(s)

Office
Lvl Main

Fireplace, Ceiling - Coffered, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Recessed Lighting

Family Room
Lvl Main,First

Flooring - Hardwood, Window(s) - Picture, French Doors, Exterior Access, Open Floorplan, Recessed Lighting, Decorative Molding

Master Bedroom
Lvl Main,First

Bathroom - Full, Walk-In Closet(s), Flooring - Hardwood, Window(s) - Picture, French Doors, Exterior Access, Recessed Lighting, Decorative Molding

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second

Bathroom - Full, Closet, Flooring - Hardwood, Window(s) - Picture, Recessed Lighting

Bedroom 4
Lvl Second

Bathroom - Full, Walk-In Closet(s), Flooring - Hardwood, Window(s) - Picture, Recessed Lighting

Bedroom 5
Lvl Second

Bathroom - Full, Flooring - Hardwood, Window(s) - Picture, Recessed Lighting, Closet - Double

Bathroom 1
Lvl First

Bathroom - Half, Flooring - Stone/Ceramic Tile

Bathroom 2
Lvl Second

Bathroom - Full, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub, Flooring - Stone/Ceramic Tile, Steam / Sauna

Bathroom 3
Lvl Main,First

Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Recessed Lighting

Property History

Listed
$16,900,000

Jul 15, 2026

MLS® 73550581

Listed
$60,000

Jun 7, 2026

MLS® 73531424

Terminated
$14,900,000

Oct 15, 2024

MLS® 73276596

Listed
$14,900,000

Aug 12, 2024

MLS® 73276596

Population

11,579

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$250K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

12.5%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Middlesex County

2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 10,116 sq ft principal dwelling). Lot size: 87,878 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Full Weston, MA market report ZIP 02493 market data
Listing Provided By

Listing Agent: Rose Hall

Listing Office: Blue Ocean Realty, LLC

MLS® Number: 73550581

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