50 Winsor Way Weston — Photo 1 of 35
$16,900,000
Investment Analysis — 50 Winsor Way
Weston, MA 02493
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 6-bedroom in 02493 carries an estimated $4,010/mo in gross rent — about a -0.64% cap rate and $-107,517/yr in estimated NOI at the $16,900,000 list price. Adjust every assumption in the calculator below.
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
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
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
Living Room
Lvl Main,FirstFlooring - Hardwood, Window(s) - Picture, Open Floorplan, Recessed Lighting, Wainscoting, Lighting - Overhead, Decorative Molding
Dining Room
Lvl Main,FirstCloset, Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Window(s) - Picture, Breakfast Bar / Nook, Recessed Lighting, Decorative Molding
Kitchen
Lvl FirstCoffered 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 MainFireplace, Ceiling - Coffered, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Recessed Lighting
Family Room
Lvl Main,FirstFlooring - Hardwood, Window(s) - Picture, French Doors, Exterior Access, Open Floorplan, Recessed Lighting, Decorative Molding
Master Bedroom
Lvl Main,FirstBathroom - Full, Walk-In Closet(s), Flooring - Hardwood, Window(s) - Picture, French Doors, Exterior Access, Recessed Lighting, Decorative Molding
Bedroom 2
Lvl SecondBedroom 3
Lvl SecondBathroom - Full, Closet, Flooring - Hardwood, Window(s) - Picture, Recessed Lighting
Bedroom 4
Lvl SecondBathroom - Full, Walk-In Closet(s), Flooring - Hardwood, Window(s) - Picture, Recessed Lighting
Bedroom 5
Lvl SecondBathroom - Full, Flooring - Hardwood, Window(s) - Picture, Recessed Lighting, Closet - Double
Bathroom 1
Lvl FirstBathroom - Half, Flooring - Stone/Ceramic Tile
Bathroom 2
Lvl SecondBathroom - Full, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub, Flooring - Stone/Ceramic Tile, Steam / Sauna
Bathroom 3
Lvl Main,FirstBathroom - 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
$16,900,000
Jul 15, 2026
MLS® 73550581
$60,000
Jun 7, 2026
MLS® 73531424
$14,900,000
Oct 15, 2024
MLS® 73276596
$14,900,000
Aug 12, 2024
MLS® 73276596
Listing Agent: Rose Hall
Listing Office: Blue Ocean Realty, LLC
MLS® Number: 73550581