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50 Winsor Way, Weston MA 02493

Weston, MA 02493
$16,900,000
Est. $97,663/month
6
Beds
8.5
Baths
10,116
Sq Ft
$1,671
Price/Sq Ft
2.02
Acres
2004
Year Built
4
Garage Spaces
6 hours 1 minute
Time on Market
Active Listed Jul 15, 2026 • MLS# 73550581 Copied! • Updated Jul 15, 2026

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

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Recently Sold Nearby

Property History

Market Insights

39.6%
Price Range
1
Previous Sales

Property Timeline

🏠
Listed for Sale
Jul 16, 2026
$16,900,000
Original listing
Agent: Rose Hall Office: Blue Ocean Realty, LLC
Previous Transaction - MLS #72904167
Full transaction history available when tracking began
🏷️
Previously Sold
Jan 21, 2022
$10,200,000
MLS #72904167

Tax History

Year Taxes Assessment
2026 $144,088 $13,243,400

Financial Details

Annual Property Tax
$144,088
Tax Year 2026
Assessed Value
$13,243,400

Facts & Features

4 Car Garage
Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 2004
Living Area 10,116 sq ft
Lot Size 2.02 acres
Bedrooms 6
Full Baths 7
Half Baths 3
Total Rooms 17

Interior

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
Appliances Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Fireplace Family Room, Living Room, Master Bedroom
Fireplaces 4
Basement Full, Finished, Interior Entry
Laundry Electric Dryer Hookup, Washer Hookup, First Floor
Features Closet/cabinets - Custom Built, Recessed Lighting, Coffered Ceiling(s), Closet, Study, Office, Media Room, Wine Cellar, Bonus Room, Exercise Room, Sauna/steam/hot Tub

Exterior

Construction Frame
Architecture Colonial
Roof Wood
Features Patio, Balcony, Pool - Inground, Pool - Inground Heated, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard, Stone Wall
Pool In Ground, Pool - Inground Heated
Spa None
Fencing Fenced
Patio/Porch Patio
Garage Spaces 4
Has Garage Yes
Features Attached, Garage Door Opener, Heated Garage, Storage, Paved Drive, Off Street, Driveway
Total Spaces 19
Electric Generator
Water Public
Sewer Private Sewer
Gas None
Other For Gas Range
Annual Tax $144,088
Assessed Value $13,243,400
Fee Includes None
Amenities None
Optional Fee Includes None
Seller Disclosures None
Possession None
Accepted Financing None
Structure Type []
Sq Ft Source Public Record
Sq Ft Disclosures Living area is approximate
Documents None
County Middlesex

Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
2004
Bedrooms
6
Full Bathrooms
7
Half Bathrooms
3
Living Area
10,116 sq ft
Total Rooms
17
Main Level Bedrooms
1

Room Details

First Floor

Bathroom1
Bathroom - Half, Flooring - Stone/Ceramic Tile
Kitchen
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)

Second Floor

Bedroom5
Bathroom - Full, Flooring - Hardwood, Window(s) - Picture, Recessed Lighting, Closet - Double
Bedroom4
Bathroom - Full, Walk-In Closet(s), Flooring - Hardwood, Window(s) - Picture, Recessed Lighting
Bedroom3
Bathroom - Full, Closet, Flooring - Hardwood, Window(s) - Picture, Recessed Lighting
Bathroom2
Bathroom - Full, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub, Flooring - Stone/Ceramic Tile, Steam / Sauna
Bedroom2
Bathroom - Full, Closet, Flooring - Hardwood, Window(s) - Picture, Recessed Lighting

Main Floor

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

Other Floor

Master Bathroom
Yes

Main,First Floor

Dining Room
Closet, Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Window(s) - Picture, Breakfast Bar / Nook, Recessed Lighting, Decorative Molding
Living Room
Flooring - Hardwood, Window(s) - Picture, Open Floorplan, Recessed Lighting, Wainscoting, Lighting - Overhead, Decorative Molding
Bathroom3
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
Master Bedroom
Bathroom - Full, Walk-In Closet(s), Flooring - Hardwood, Window(s) - Picture, French Doors, Exterior Access, Recessed Lighting, Decorative Molding
Family Room
Flooring - Hardwood, Window(s) - Picture, French Doors, Exterior Access, Open Floorplan, Recessed Lighting, Decorative Molding

Interior Features

Flooring: Tile, Carpet, Hardwood, Stone / Slate, Flooring - Hardwood, Flooring - Wall to Wall Carpet, Flooring - Stone/Ceramic Tile
Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Interior Features: Closet/Cabinets - Custom Built, Recessed Lighting, Coffered Ceiling(s), Closet, Study, Office, Media Room, Wine Cellar, Bonus Room, Exercise Room, Sauna/Steam/Hot Tub
Windows: Window(s) - Picture, Window(s) - Bay/Bow/Box, Insulated Windows, Screens
Basement: Full, Finished, Interior Entry
Laundry: Electric Dryer Hookup, Washer Hookup, First Floor
Security: Security System

Construction & Materials

Style: Colonial
Year Built: 2004
Structure Type:
Exterior Materials: Frame
Roof: Wood
Foundation: Concrete Perimeter

Heating, Cooling & Utilities

Heating: Central, Forced Air, Natural Gas, Fireplace
Heating Zones: 8
Cooling: Central Air
Cooling Zones: 8
Hot Water:
Water Source: Public
Sewer: Private Sewer
Energy Features: Thermostat

Exterior & Lot

Exterior Features: Patio, Balcony, Pool - Inground, Pool - Inground Heated, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard, Stone Wall
Patio & Porch: Patio
Fencing: Fenced
Other Structures:
Lot Features:
Road Surface:

Parking & Garage

Garage Spaces: 4
Garage Type: Attached
Total Parking Spaces: 19
Parking Features: Attached, Garage Door Opener, Heated Garage, Storage, Paved Drive, Off Street, Driveway

Special Features

Fireplaces: 4
Fireplace Type: Family Room, Living Room, Master Bedroom
Pool: Private Pool
Pool Features: In Ground, Pool - Inground Heated
View: Yes
View Type: Scenic View(s)
Community Amenities: Pool, Tennis Court(s), Walk/Jog Trails, Golf, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School

Nearby Schools

School information not available for this location.

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Including down payment
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $12,007
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Location

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Neighborhood

50 Winsor Way, Weston MA 02493

Weston, MA 02493

Listing Information

Listing Agent Rose Hall
Listing Office Blue Ocean Realty, LLC
Office Phone 617-206-5700
Agent MLS ID CN200679
Office MLS ID AN2056
Listing Data Updated Jul 15, 2026 9:14 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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