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$7,595,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 6 Full Baths
  • 1 Partial Bath
  • 7,700 Sq. Ft.
  • 2 Car Garage
  • Updated 8 days ago
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Featured in House Beautiful (Feb '22), this home in the private Milbrook Association showcases the exceptional work of renowned interior designer Jamie Drake set amidst the beautifully curated grounds by Janice Parker. Elegant open-concept layout with 10-ft ceilings perfectly suited for both grand entertaining and quiet escape. Luxurious owner's suite with fireplace, morning kitchen, spa bath, dual walk-in closets and balcony overlooking backyard. Three additional en-suite bedrooms upstairs. Lower level with office/5th bedroom, gym and rec room. Highlights include 3-floor elevator, attached 2-car garage, Sonos/Savant smart home system, fiber-optic internet, electronic window shades. Terrace with covered seating area, outdoor fireplace and barbecue. Opportunity to buy home fully furnished.

Full Property Details for 248 Overlook Dr

General

  • Price: $7,595,000
  • Taxes: $37,943
  • Status: Active
  • Type: Single Family
  • Source: Greenwich
  • MLS ID: 125926
  • Updated: 9/26/2026
  • Added to Site: 12 day(s) ago

Interior

  • Interior Features: Built-in Features, Pantry, Elevator
  • Number of Fireplaces: 5

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 6
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Security/Safety: 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, Hydro-Air
  • Heating Fuel: Gas
  • Water Heater: Gas

Utilities

  • Gas: Public Utility
  • Sewer: Town Sewer
  • Water: Public

Structural Information

  • Architectural Style: Shingle
  • Construction: Shingle Siding
  • Basement Desc.: Exterior Access, Finished
  • Roof: Wood
  • Windows: Double Pane Windows
  • Square Feet: 7,700
  • Sq. Ft. Source: Architect
  • Year Built: 2018

Lot Features

  • Lot Size (Acres): 0.49
  • Lot Size (Sq. Ft.): 21,344.4
  • Topography: True
  • Lot Features: Parklike
  • Zoning: R-12
  • Lot Description: Park

Financial Considerations

  • Price Per Sq. Ft.: $986.36
  • Tax Amount: $37,943

Disclosures and Reports

  • Exclusions: Call LB
  • Inclusions: Washer/Dryer, All Kitchen Applncs
  • Property ID: 01-3171/S

Listed by Sotheby's International Realty

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Listing agent

— 248 Overlook Dr —

  • Sotheby's International Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 248 Overlook Dr

School District:Greenwich School District
NameGradesDistance
Julian Curtiss School
180 East Elm Street, Greenwich, CT 06830
PK-50.3 mi
Central Middle School
9 Indian Rock Lane, Greenwich, CT 06830
6-81.5 mi
Greenwich High School
10 Hillside Road, Greenwich, CT 06830
9-120.7 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 248 Overlook Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/23/2026
Listed
$7,595,000
87.07%
MLS
1/14/2020
Sold
$4,060,000
—
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 248 Overlook Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$36,682
4%
$2,968,000
—
2023
$35,426
3%
$2,968,000
—
2023
$34,536
1%
$2,968,000
—
2022
$34,221
-12%
$2,968,000
-9%
2021
$39,092
—
$3,246,880
—
2020
$39,027
-11%
$3,246,880
-10%
2019
$43,634
125%
$3,594,220
120%
2018
$19,418
102%
$1,635,900
105%
2017
$9,594
2%
$798,210
—
2016
$9,442
16%
$798,210
16%
2015
$8,155
2%
$687,400
—
2014
$7,991
3%
$687,400
—
2013
$7,774
—
$687,400
—
2011
$7,774
—
$687,400
—
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 Sotheby's International Realty

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248 Overlook Drive, Greenwich, CT 06830 (MLS# 125926) is a Single Family property with 5 bedrooms, 6 full bathrooms and 1 partial bathroom. 248 Overlook Drive is currently listed for $7,595,000 and was received on September 23, 2026. Want to learn more about 248 Overlook 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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