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$7,825,000

  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 6 Full Baths
  • 3 Partial Baths
  • 8,970 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 105 Woodside Dr

General

  • Price: $7,825,000
  • Taxes: $53,260
  • Status: Active
  • Type: Single Family
  • Source: Greenwich
  • MLS ID: 123529
  • Updated: 1/21/2026
  • Added to Site: 179 day(s) ago

Interior

  • Interior Features: Kitchen Island, Built-in Features, Entrance Foyer, Sep Shower
  • 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, Smoke Detector(s)

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: Normandy
  • Construction: Stone
  • Basement Desc.: Finished
  • Roof: Tile
  • Square Feet: 8,970
  • Sq. Ft. Source: Architect
  • 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: Corner Lot, Parklike
  • Zoning: R-12
  • Lot Description: Park
  • Fencing (Description): Invisible Fence

Water Features

  • Water Front: Yes
  • Water Front Desc.: Pond, Lake, Waterfront
  • Lake Front: Yes

Financial Considerations

  • Price Per Sq. Ft.: $872.35
  • Tax Amount: $53,260

Disclosures and Reports

  • Exclusions: Invisible Fence
  • Inclusions: Washer/Dryer, All Kitchen Applncs
  • Property ID: 01-1081/S

Listed by Houlihan Lawrence

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Listing agent

— 105 Woodside Dr —

  • Houlihan Lawrence

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 105 Woodside Dr

School District:Greenwich School District
NameGradesDistance
Julian Curtiss School
180 East Elm Street, Greenwich, CT 06830
PK-50.4 mi
Central Middle School
9 Indian Rock Lane, Greenwich, CT 06830
6-81.4 mi
Greenwich High School
10 Hillside Road, Greenwich, CT 06830
9-120.7 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 105 Woodside Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/14/2026
Price Reduced
$7,825,000
-1.57%
MLS
9/05/2025
Listed
$7,950,000
29.58%
MLS
7/05/2005
Sold
$6,135,000
—
Public Record
Get Price Alerts and Save Property
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 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
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Houlihan Lawrence

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105 Woodside Drive, Greenwich, CT 06830 (MLS# 123529) is a Single Family property with 6 bedrooms, 6 full bathrooms and 3 partial bathrooms. 105 Woodside Drive is currently listed for $7,825,000 and was received on September 05, 2025. 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.

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