Prevu by reAlpha
BuySellBlogBrowse Listings

105 Woodside DriveGreenwich, CT 06830

For Sale

$7,825,000

Smart Buyer Rebate $78,250

Located within the sought-after private association of Milbrook, this stately stone manor blends timeless old-world charm with thoughtful modern updates. A recent addition and renovation features a stunning great room with a soaring 19-foot ceiling and lake views, as well as a stone terrace overlooking the water, a beautifully updated primary suite, and an exceptional mudroom. Perfectly suited for entertaining and memorable family gatherings, the home offers both elegance and comfort. Milbrook Association features gated access, a dedicated security team, and the Milbrook Country Club, providing an unparalleled lifestyle. This remarkable residence offers the rare combination of close-to-town convenience and the exclusivity of a private community.

Listed by Sarah Muir

·

License #RES.0813247

·

Houlihan Lawrence

·

203-219-1535

Last updated January 23, 2026

·

Source: FlexMLS #123529

Listing Facts

  • TypeSingle-family
  • NeighborhoodMillbrook
  • Bedrooms6
  • Bathrooms7.5
  • Days on Prevu147
  • HOA/Maint. Fees$10,826/year
  • Taxes$53,260/year
  • Size8,970 sqft
  • Price per sqft$872

Amenities

  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

01/14/2026
Price Decreased
$7,825,000
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 Fence
  • 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 43% above the average price for single-family homes in Millbrook and has been on the market for 85 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. Available on Prevu for 147 days at $7,825,000. This includes a recent price decrease of $125,000. 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. Additional amenities include 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.