3 Woodside Drive, Greenwich, Connecticut

$14,495,000

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9

Beds

15

Baths

14,000

Square feet

1.66

Acres

About 3 Woodside Drive

Welcome to Milbrook Manor! No need to live in mid or back country to enjoy a sprawling estate. This prestigious, private sanctuary spanning 4 light filled floors with 7 fireplaces is situated on 1.66 acres in the picturesque Milbrook neighborhood of Greenwich with its own gated security and country club. Built with the finest interior and exterior designer finishes- cedar roof, copper gutters, cedar siding and front stone siding and chimneys comprised of stone from the surrounding grounds- There is no other new construction home currently on the market of this size and scale in town close to elite restaurants, school and shops. The walk out lower level with tall 10' ceilings and top floor feature multiple bars, fireplaces and flex spaces for sleeping quarters, office and recreational use for family or staff with all floors accessible by elevator. This energy efficient smart home compound sports a sophisticated AV prewired system in the theater room, music/dance studio, gym and separate golf simulator room with extra height ceilings in the garden level. Pet grooming station, second laundry room, sauna, beauty parlor and temperature controlled wine room finish the magnificent lower level wellness retreat. An inviting double height foyer, double staircase and soaring ceilings greet all who enter this breathtaking modern New England colonial home with open floor plan. Exit seamlessly to the backyard, a serene oasis of meticulously landscaped bluestone terraces highlighted

Features of 3 Woodside Drive

MLS® # 24209961
Price $14,495,000
Bedrooms 9
Bathrooms 15.00
Full Baths 12
Half Baths 3
Square Footage 14,000
Acres 1.66
Type Single Family For Sale
Style Colonial, Contemporary
Status Active

Community Information

Address 3 Woodside Drive
Area N/A
City Greenwich
County Fairfield
State Connecticut
Zip Code 06830

Amenities

Features Energy Star Rated, Home Energy Rating, Programmable Thermostat
Parking Attached Garage
# of Garages 4
Is Waterfront No
Waterfront Beach Rights
Has Pool Yes
Pool Gunite, Heated, In Ground Pool

Interior

Interior Features Cable - Pre-wired, Central Vacuum, Elevator, Open Floor Plan, Sauna, Security System
Appliances Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Dishwasher, Disposal, Washer, Dryer
Heating Hydro Air, Propane
Cooling Central Air
Fireplace Yes
# of Fireplaces 7
Has Basement Yes
Basement Full, Heated, Fully Finished, Garage Access, Cooled, Liveable Space

Exterior

Exterior Cedar, Stone
Exterior Features Balcony, Terrace
Lot Description Level Lot
Roof Shake
Foundation Concrete

School Information

Elementary Julian Curtiss
Middle Central
High Greenwich

Additional Information

Date Listed September 26th, 2026
Days on Market 11
Zoning R-20
RE / Bank Owned No

Listing Details

OfficeBerkshire Hathaway NE Prop.

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Listing information last updated on October 6th, 2026 at 10:44pm EDT.