3 Woodside Drive, Greenwich, Connecticut 06830

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

Flood risk: check the FEMA flood map for this address.

Schools

Interior

Building & Exterior

Lot & Land

Energy

What it would cost per month

An estimate you can adjust — not a quote, and not an offer of credit. Principal and interest only, plus the taxes and HOA already on this listing. Insurance, PMI and closing costs are not included. Rate seeded at 6.5% (August 2026); change it to whatever your lender quotes.

What's nearby

Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.

Recent comparable sales

The 5 closest recent sales to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded sale prices from the MLS, not estimates. No automated valuation is shown, because what a home is worth depends on condition, layout and timing that a formula cannot see — call John at 203·883·3399 to read them properly against this home.

5 comparable sales — median $9,000,000, ranging $6,250,000 to $16,500,000.

Within about a mile and a half, sold in the last 2 years
• 3 Anderson Road6 bd · 9 ba · 9,845 sq ft · 0.6 mi away
  $9,000,000$914/sq ft2026-02-09
Same town, sold in the last 3 years
• 14 Meadow Drive10 bd · 9 ba · 9,483 sq ft · 1.4 mi away
  $7,700,000$811/sq ft2025-11-28
• 52 Carriglea Drive6 bd · 7 ba · 9,418 sq ft · 1.5 mi away
  $12,900,000$1,369/sq ft2025-12-05
• 382 North St Street6 bd · 12 ba · 14,126 sq ft · 1.7 mi away
  $16,500,000$1,168/sq ft2025-12-17
• 386 North Street5 bd · 9 ba · 13,474 sq ft · 1.7 mi away
  $6,250,000$463/sq ft2026-06-23

More homes in Greenwich

Closest in price to this one.

• 532 Round Hill Road7 bed · 11 bath · 14,000 sq ft$14,495,000
• 4 Little Cove Lane5 bed · 7 bath · 6,069 sq ft$12,900,000
• 190 North Street7 bed · 11 bath · 12,176 sq ft$12,750,000
• 86 Howard Road7 bed · 11 bath · 15,896 sq ft$11,995,000
• 67 Stag Lane6 bed · 10 bath · 12,310 sq ft$10,995,000
• 41 Mohawk Lane6 bed · 9 bath · 7,838 sq ft$9,995,000

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