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105 Woodside DriveGreenwich, CT 06830

For Sale

$7,950,000

Smart Buyer Rebate $79,500

This stately prewar stone manor, located in the exclusive gated community of Milbrook, has been thoughtfully expanded and reimagined for modern living while preserving its timeless elegance. Stepping into the grand foyer, graced with a beautiful curved staircase, the home reveals its extraordinary character and sophistication.
Designed for both comfortable living and exceptional entertaining, the home features a great room overlooking the lake with a soaring 19-foot ceiling. The entertaining rooms are spacious with extra ceiling height. The primary suite has 2 luxurious bathrooms and a spacious dressing room.
Set on nearly an acre of lakefront property and ideally situated near the Milbrook Club, Greenwich Ave, schools, & train, this remarkable home combines convenience & exclusivity.

Listed by Sarah Muir

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License #RES.0813247

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Houlihan Lawrence

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203-219-1535

Last updated October 08, 2025

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Source: FlexMLS #123529

Listing Facts

  • TypeSingle-family
  • NeighborhoodMillbrook
  • Bedrooms6
  • Bathrooms7.5
  • Days on Prevu97
  • HOA/Maint. Fees$10,826/year
  • Taxes$53,260/year
  • Size8,970 sqft
  • Price per sqft$886

Amenities

  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

09/05/2025
Listed by Houlihan Lawrence
$7,950,000

Property Details for 105 Woodside Drive

Association

Amenities

  • Association Amenities: Gated

Fees

  • Association Fee: $10,826.00 Annually

General

  • Association Name: Milbrook

Exterior

Construction

  • Roof: Tile
  • Year Built: 1930
  • Architectural Style: Normandy
  • Construction Materials: Stone

Features

  • Fencing: Invisible
  • Waterfront Features: Pond, Lake, Waterfront
  • Waterfront: Yes

Measurements

  • Building Area Total: 8,970
  • Lot Features: Corner Lot, Parklike
  • Lot Size Acres: 0.88
  • Lot Size Area: 0
  • Lot Size Square Feet: 38,332
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 01-1081/S
  • Tax Annual Amount: $53,260.00
  • Tax Assessed Value: $6,156,300.00

Interior

Features

  • Fireplace: Yes
  • Fireplaces Total: 4
  • Interior Features: Kitchen Island, Built-in Features, Entrance Foyer, Sep Shower

Rooms

  • Basement: Finished
  • Bathrooms Full: 6
  • Bathrooms Half: 3
  • Bathrooms Total Integer: 9
  • Bedrooms Total: 6

Other

General

  • Exclusions: Invisible Fence

Location

  • City Region: South Of Post Road

Parking

Parking

  • Garage Spaces: 2
  • Parking Features: Attached Garage, Garage Door Opener

Schools

Elementary School

  • Elementary School: Julian Curtiss

Middle or Junior School

  • Middle Or Junior School: Central

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Heating: Natural Gas, Combination
  • Has Heating: Yes
  • Laundry Features: Laundry Room
  • Sewer: Town Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 6 bedrooms and 7.5 bathrooms in this single-family home at 105 Woodside Drive.

What schools are nearby to 105 Woodside Drive?

Nearby schools include the Julian Curtiss Elementary School and Central Middle School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 105 Woodside Drive.

What are the annual taxes for 105 Woodside Drive?

Annual taxes for this single-family home are estimated at $53,260.

How does 105 Woodside Drive compare to other single-family homes in Millbrook?

This single-family home is listed 45% above the average price for single-family homes in Millbrook and has been on the market for 35 more days than the typical home in this area.

What building or home owners association is the single-family home part of?

This single-family home is part of the Milbrook home owners association.

What is the square footage on this single-family home?

According to the MLS, this listing is 8,970 sqft.

105 Woodside Drive is a 6-bedroom, 7.5-bath single-family home for sale in Greenwich CT 06830. On Prevu for 97 days at $7,950,000. This residence features 8,970 square feet of living space, located in Fairfield County. The median listing price for single-family homes in this area is $5,472,000. Nearby schools include Julian Curtiss Elementary School and Central Middle School. The home offers air conditioning, parking, and washer/dryer. View other single-family home listings in Fairfield County.

Based on information from Greenwich Multiple Listing Service, Inc. and/or other sources. All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by Prevu or the MLS. Information is provided exclusively for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.