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271 Overlook Drive, 
Greenwich, CT 06830

$4,795,000


5

Beds


5

Baths


4,778

Sq Ft


Single Family

Active

Listed by

Ellen Mosher

Houlihan Lawrence

Last updated:

October 8, 2026, 02:43 PM

MLS#

125962

Source:

CT GAR

About This Home

271 Overlook Drive

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!

Home Facts

Single Family

5 Baths

5 Bedrooms

Built in 2011

Price Summary

4,795,000

$1,003 per Sq. Ft.

MLS #:

125962

Last Updated:

October 8, 2026, 02:43 PM

Added:

10 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

4

Interior

Living Area:

4,778 Sq. Ft.


Structure

Structure

Building Area:

4,778 Sq. Ft.

Year Built:

2011


Lot

Lot Size (Sq. Ft):

12,632


Finances & Disclosures

Finances

Price:

$4,795,000

Price per Sq. Ft:

$1,003 per Sq. Ft.

Source:CT GAR
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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.