3 Woodside Drive
Greenwich, Connecticut 06830
- Beds
- 9
- Baths
- 12 | 3
- SqFt
- 14,000
- Acres
- 1.66
- Year Built
- 2027
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
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
Key Facts
- City/Town
- Greenwich
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Contemporary
- Year Built
- 2027
- Days on Market
- 0 days
- Beds
- 9
- Baths
- 12 full · 3 half
- Living Area
- 14,000 sq ft
- Lot Size
- 1.66 acres
- Garage / Parking
- 4 garage
- Property Taxes
- Not on file from MLS
Market Snapshot
The Greenwich Market
Single Family · trailing 12 months
Active Listings
52
20 under contract
Median List Price
$3.25M
52 active listings
Median Closed Price
$2.50M
210 sales
Median Days on Market
27
52 active listings
Median $ / Sq Ft
$848
52 active listings
Sale-to-List Ratio
101.2%
210 sales
How this home compares
List Price
$14.49M
vs $3.25M median
4.5× the median
Price / Sq Ft
$1,035
vs $848 median
22.1% above median
Days on Market
0 days
vs 27 days median
27 days fresher than median
Based on 52 active and 210 closed sales (trailing 12 mo) of single family in Greenwich. Source: SmartMLS · As of September 26, 2026.
Location
3 Woodside Drive, Greenwich, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$77,382
- Property Taxes$0
- Insurance$4,832
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Greenwich
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial,Contemporary
- Year Built
- 2027
- New Construction
- Under Construction
- Living Area
- 14,000 sq ft
Schools
- Elementary
- Julian Curtiss
- High
- Greenwich
Interior
- Heating
- Hydro Air
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 7
- Laundry
- Lower LevelUpper Level
- Laundry Location
- separate rooms
- Appliances
- Gas RangeWall OvenMicrowaveRange HoodRefrigeratorFreezerSubzeroDishwasherDisposalWasherDryer
- Basement
- FullHeatedFully FinishedGarage AccessCooledLiveable Space
- Interior Features
- Cable - Pre-wiredCentral VacuumElevatorOpen Floor PlanSaunaSecurity System
- Additional Rooms
- Bonus RoomExercise RoomGymMud RoomMusic RoomSteam/SaunaWine Cellar
Exterior & Lot
- Lot Size
- 1.66 acres
- Zoning
- R-20
- Garage / Parking
- 4 garage spacesAttached Garage
- Waterfront Details
- Beach Rights
- Water Source
- Public Water Connected
- Sewer
- Public Sewer In Street
- Pool
- GuniteHeatedIn Ground Pool
- Construction
- CedarStone
- Color
- white
- Roof
- Shake
- Foundation
- Concrete
- Exterior Features
- BalconyTerrace
- Lot Description
- Level Lot
Listing & Financials
- Days on Market
- 0
- MLS #
- 24209961
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/26/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/26/2026 at 9:15 PM UTC.