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5 Beds
5 Baths
4,778 sqft

$4,795,000

271 Overlook Drive, Greenwich CT, 06830

Price per sqft$1,003.56
Built in2011
Property size4,778 sqft
Property typeResidential

Overview

Active

Listed Sep 30, 2026

Updated 20h ago

The property you have been waiting for! Chic, sun-filled and turn key, this beautifully appointed five-bedroom home pairs fresh, modern interiors with the warmth and character of a classic Greenwich residence. Tucked into the coveted Milbrook Association, just around the corner from the private Club and minutes from Greenwich Avenue, the train and schools, 271 Overlook offers an exceptional combination of neighborhood charm, in-town convenience and relaxed luxury. High ceilings, hardwood floors and abundant natural light set the tone throughout. Gracious formal rooms give way to a welcoming Great Room with fireplace, a sun-filled breakfast room and newly redesigned contemporary kitchen with direct access to an expansive stone terrace. A walk-in pantry, mudroom and powder room complete the main level. Upstairs, the spectacular primary suite features vaulted ceiling, an exceptional closet and a luxurious bath with radiant heated floors. Three additional light-filled bedrooms provide generous accommodations for family and guests. The finished lower level adds flexible living and entertaining space with a wine cellar, family/playroom, office/gym, second laundry and en-suite bedroom. Outside, the setting is truly enchanting with lovely lawn for play, a shaded terrace and a fantastic vegetable garden. Experience the best of Milbrook, with dedicated security, a neighborhood playground and a welcoming sense of community, plus priority positioning for Club membership. Just steps away, the Milbrook Club offers golf, tennis, paddle, swimming and dining - an exceptional lifestyle in one of Greenwich's most coveted neighborhoods. This is Greenwich living at its best!

$31,901/mo

Est. mortgage payment based on a $4,795,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
125962

Interior Features

Bedrooms
5
Bathrooms
5
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.29 Acres

Other Property Details

Taxes
$21,549
Tax Frequency
Annually
Garage
Yes
MLS provider logo

Listed by Ellen Mosher with Houlihan Lawrence
Listing Contact:  

The IDX display contains information sourced from the Greenwich Association of REALTORS® as of 10/5/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Greenwich Association of REALTORS® all rights reserved.

Data last updated on 10/5/2026 at 6:35 AM UTC

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