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$6,995,000
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Property Description
105 Woodside Drive captures the very best of Country Club Living in Greenwich. Chic stone 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 with incredible water view 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!!
Full Property Details
Full Property Details for 105 Woodside Dr
General
- Price: $6,995,000
- Taxes: $53,260
- Status: Active
- Type: Single Family
- Source: Greenwich
- MLS ID: 124480
- Updated: 3/24/2026
- Added to Site: 14 day(s) ago
Interior
- Interior Features: Cedar Closet(s), Vaulted Ceiling(s), Built-in Features, Entrance Foyer, Sep Shower, Back Stairs
- Number of Fireplaces: 4
Rooms
Bathrooms
- Total Bathrooms: 9
- Full Bathrooms: 6
- Half Bathrooms: 3
Bedrooms
- Total Bedrooms: 6
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared Amenities: Gated
- Security/Safety: Security Guard, Security System
Exterior
- Porch/Patio/Deck: Terrace
Parking
- Garage: Yes
- Garage Spaces: 2
Location
- Area: 3 - Greenwich
- County: Fairfield
School Information
- Elementary School: Julian Curtiss
- Middle School: Central
Community
- Association: Yes
- Assoc. Name: Milbrook
Heating & Cooling
- Central air: Yes
- Air Conditioning: Yes
- Cooling Type: Central Air
- Heating Type: Natural Gas, Combination
- Heating Fuel: Gas
- Water Heater: Gas
Utilities
- Gas: Public Utility
- Sewer: Town Sewer
- Water: Public
Structural Information
- Architectural Style: Other
- Construction: Stone
- Basement Desc.: Finished
- Roof: Tile
- Square Feet: 7,292
- Sq. Ft. Source: Taxcard
- Year Built: 1930
- Year Addition: 2015
- Remodeled/Updated: 2015
Lot Features
- Lot Size (Acres): 0.88
- Lot Size (Sq. Ft.): 38,332.8
- Lot Features: Level
- Zoning: R-12
- Lot Description: Level
- Fencing (Description): Invisible Fence
Water Features
- Water Front: Yes
- Water Front Desc.: Lake, Waterfront
- Lake Front: Yes
Financial Considerations
- Price Per Sq. Ft.: $959.27
- Tax Amount: $53,260
Disclosures and Reports
- Exclusions: Invisible Fence, Call LB
- Inclusions: Washer/Dryer, All Kitchen Applncs
- Property ID: 01-1081/S
Listed by Houlihan Lawrence
Get Pre-Approved Today
Schools
Schools serving 105 Woodside Dr
School District:Greenwich School District
| Name | Grades | Distance |
|---|---|---|
Julian Curtiss School 180 East Elm Street, Greenwich, CT 06830 | PK-5 | 0.4 mi |
Central Middle School 9 Indian Rock Lane, Greenwich, CT 06830 | 6-8 | 1.4 mi |
Greenwich High School 10 Hillside Road, Greenwich, CT 06830 | 9-12 | 0.7 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 105 Woodside Dr
Date
Details
Price
Change
Source
3/12/2026
Listed
$6,995,000
14.02%
MLS
7/05/2005
Sold
$6,135,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 105 Woodside Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$53,260
4%
$4,309,410
—
2023
$51,437
3%
$4,309,410
—
2023
$50,144
1%
$4,309,410
—
2022
$49,687
—
$4,309,410
-1%
2021
$49,688
-5%
$4,366,040
—
2020
$52,480
-1%
$4,366,040
—
2019
$53,004
2%
$4,366,040
—
2018
$51,825
-1%
$4,366,040
—
2017
$52,475
8%
$4,366,040
6%
2016
$48,591
26%
$4,107,810
26%
2015
$38,662
2%
$3,259,060
—
2014
$37,887
3%
$3,259,060
—
2013
$36,860
—
$3,259,060
—
2011
$36,860
—
$3,259,060
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 105 Woodside Dr
105 Woodside Drive, Greenwich, CT 06830 (MLS# 124480) is a Single Family property with 6 bedrooms, 6 full bathrooms and 3 partial bathrooms. 105 Woodside Drive is currently listed for $6,995,000 and was received on March 12, 2026. Want to learn more about 105 Woodside Drive? Do you have questions about finding other Single Family real estate for sale in Greenwich? You can browse all Greenwich real estate or contact a Coldwell Banker agent to request more information.

