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105 Woodside DriveGreenwich, CT 06830

For Sale

$6,995,000

Smart Buyer Rebate $69,950

105 Woodside Drive captures the very best of Country Club Living in Greenwich. Chic fieldstone classic set within the gated Milbrook community, home to the coveted Milbrook Club, with the opportunity to apply for private membership--creating a lifestyle where recreation, relaxation, and social life are just moments from your front door. Perfectly sited overlooking the lake on nearly an acre, the six-bedroom residence blends modern interiors with an effortless indoor-outdoor flow designed for entertaining and everyday enjoyment. Renovated and expanded for seamless living, the crisp, light-filled residence unfolds across four levels, highlighted by a spectacular great room with soaring 19-foot ceilings, elegant formal rooms, and a welcoming family room that opens to a gourmet kitchen with center island, professional appliances and a sunny breakfast room. French doors lead to terraces and a lush backyard--an inviting setting for outdoor dining, gatherings, and play.

Upstairs, the serene primary suite offers generous walk-in closets and two luxurious baths, accompanied by three additional ensuite bedrooms. A versatile top floor provides two more bedrooms or a creative retreat, while the finished lower level (additional 1500+ sq ft) has another media area, gym, wine space and much more.

Life in Milbrook is uniquely effortless--gated privacy, dedicated security and a neighborhood playground create a true sense of community, while membership at the Milbrook Club brings golf, tennis, paddle, swimming and dining just steps away. This is what you have been waiting for!!

Listed by Ellen Mosher

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License #RES.0775225

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Houlihan Lawrence

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203-705-9680

Last updated March 13, 2026

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Source: FlexMLS #124480

Listing Facts

  • TypeSingle-family
  • NeighborhoodMillbrook
  • Bedrooms6
  • Bathrooms7.5
  • Days on Prevu4
  • HOA/Maint. Fees$10,826/year
  • Taxes$53,260/year
  • Size7,292 sqft
  • Price per sqft$959

Amenities

  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

03/12/2026
Listed by Houlihan Lawrence
$6,995,000

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: Other
  • Construction Materials: Stone

Features

  • Fencing: Invisible Fence
  • Patio And Porch Features: Terrace
  • Waterfront Features: Lake, Waterfront
  • Waterfront: Yes

Measurements

  • Building Area Total: 7,292
  • Lot Features: Level
  • 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: $4,309,410.00

Interior

Features

  • Fireplace: Yes
  • Fireplaces Total: 4
  • Interior Features: Cedar Closet(s), Vaulted Ceiling(s), Built-in Features, Entrance Foyer, Sep Shower, Back Stairs

Rooms

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

Other

General

  • Exclusions: Invisible Fence, Call LB

Location

  • City Region: South Of Post Road

Parking

Parking

  • Garage Spaces: 2
  • Parking Features: Attached Garage

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 28% above the average price for single-family homes in Millbrook and has been on the market for 58 less 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 7,292 sqft.

105 Woodside Drive is a 6-bedroom, 7.5-bath single-family home for sale in Greenwich CT 06830. Available on Prevu for 4 days at $6,995,000. This property features 7,292 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 private outdoor space, air conditioning, parking, and washer/dryer. Browse more 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.