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!
Under contract
$4,795,000
271 Overlook Dr, Greenwich, CT 06830
5beds
4,778sqft
Residential, Single Family Residence
Built in 2011
0.29 Acres Lot
$4,749,800 Zestimate®
$1,004/sqft
$260/mo HOA
What's special
En-suite bedroomNewly redesigned contemporary kitchenHigh ceilingsFantastic vegetable gardenAbundant natural lightGracious formal roomsExceptional closet
- 11 days
- 2,142
- 159
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Ellen Mosher 203-705-9680,
Houlihan Lawrence
Source: Greenwich MLS, Inc.,MLS#: 125962
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Heating
- Natural Gas, Forced Air
Cooling
- Central Air
Appliances
- Laundry: Laundry Room
Features
- Pantry, Central Vacuum
- Basement: Finished
- Number of fireplaces: 2
Interior area
- Total structure area: 4,778
- Total interior livable area: 4,778 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Garage
- Garage spaces: 2
Features
- Patio & porch: Terrace
Lot
- Size: 0.29 Acres
- Features: Level
Details
- Parcel number: 13193/S
- Zoning: R-12
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Residential, Single Family Residence
Materials
- Shingle Siding, Stone
- Roof: Asphalt
Condition
- Year built: 2011
- Major remodel year: 2020
Utilities & green energy
- Water: Public
Community & HOA
Community
- Security: Security System
HOA
- Has HOA: Yes
- HOA fee: $3,124 annually
- HOA name: Milbrook
Location
- Region: Greenwich
Financial & listing details
- Price per square foot: $1,004/sqft
- Tax assessed value: $2,055,410
- Annual tax amount: $21,549
- Date on market: 9/30/2026
- Inclusions: Washer/Dryer, All Kitchen Applncs
Estimated market value
$4,749,800
$4.51M - $4.99M
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 10/8/2026 | Contingent | $4,795,000$1,004/sqft |
Source: | ||
| 9/30/2026 | Listed for sale | $4,795,000+88%$1,004/sqft |
Source: | ||
| 8/1/2017 | Sold | $2,550,000-5.4%$534/sqft |
Source: Public Record Report a problem | ||
| 6/1/2017 | Price change | $2,695,000-5.4%$564/sqft |
Source: Houlihan Lawrence #99589 Report a problem | ||
| 5/22/2017 | Price change | $2,850,000-3.4%$596/sqft |
Source: Houlihan Lawrence #99589 Report a problem | ||
| 4/21/2017 | Listed for sale | $2,950,000+218.9%$617/sqft |
Source: Houlihan Lawrence #99589 Report a problem | ||
| 12/16/2010 | Sold | $925,000$194/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $19,465 +3.5% | $1,574,930 |
| 2024 | $18,798 +2.6% | $1,574,930 |
| 2023 | $18,326 +0.9% | $1,574,930 |
| 2022 | $18,159 -10.6% | $1,574,930 -6.6% |
| 2021 | $20,309 +0.2% | $1,686,790 |
| 2020 | $20,275 -1% | $1,686,790 |
| 2019 | $20,478 +2.3% | $1,686,790 |
| 2018 | $20,022 -2.3% | $1,686,790 -1% |
| 2017 | $20,487 +30.6% | $1,704,570 +29.5% |
| 2015 | $15,691 +2.6% | $1,315,790 |
| 2014 | $15,296 +2.8% | $1,315,790 |
| 2013 | $14,882 +49.7% | $1,315,790 +45.6% |
| 2012 | $9,941 +28.7% | $903,700 +24.4% |
| 2011 | $7,727 -0.1% | $726,180 -15.2% |
| 2010 | $7,737 +3.4% | $855,890 |
| 2009 | $7,480 +3.5% | $855,890 |
| 2008 | $7,224 | $855,890 |
| 2007 | -- | -- |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 06830
Nearby schools
Schools provided by the listing agent
- Elementary: Julian Curtiss
- Middle: Central
Source: Greenwich MLS, Inc.. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.





