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3 Woodside Drive

Greenwich, Connecticut 06830

ACTIVE - NEW$14,495,000
Beds
9
Baths
12 | 3
SqFt
14,000
Acres
1.66
Year Built
2027
Matt Caiola

Matt Caiola

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ElevatorWine CellarPool4-Car Garage7 FireplacesNew Construction

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$82,214

per 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

Similar Properties

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Listed By

Nina Frandson

(646) 284-0088

Berkshire Hathaway NE Prop.

(203) 869-0500

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.