19 Overlook Dr, Greenwich, CT 06830
OFF MARKET

19 Overlook Dr
Greenwich, CT 06830

  • 5 Beds
  • 5.5 Baths
  • 6,421 sqft (on 0.36 acres)

$5,205,900

Trulia Estimate
as of Jul 28, 2026
Est. Refi. Payment $34,198/mo*
Refinance Your Home

$5,205,900

Trulia Estimate
as of Jul 28, 2026
Est. Refi. Payment $34,198/mo*
Refinance Your Home
5 Beds
5.5 Baths
6,421 sqft
(on 0.36 acres)

Local Information

  • Map ViewExplore the area around 19 Overlook Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1929
Lot Size
0.36 acres
Living Area
6,421 sqft
Price/Sqft
$811
Parking
Garage

About this House

Luxurious 5BR/5.1BA Milbrook estate redefines modern living. The chef's kitchen, with a 12-foot island and Wolf/Gaggenau appliances, connects to the family room, fireplace, and French doors opening to a bluestone patio with a built-in grill. The living room features a wet bar, while the dining room boasts coffered ceilings and oversized windows. The primary suite offers cathedral ceilings, a 14' X 18' walk-in closet, and a stunning bath. 4 more bedrooms, 3 full baths, and a laundry room are on the 2nd level. The 3rd level provides versatile space, and the finished lower level offers additional playroom, living space, and storage. With hardwood floors, custom cabinetry, and meticulous attention to detail, this home epitomizes luxury.
19 Overlook Dr, Greenwich, CT 06830 is a 5 bedroom, 6 bathroom, 6,421 sqft single-family home built in 1929. It last sold for $4,350,000 on Sep 16, 2024 (7% above the $4,050,000 asking price). It is currently off market. The Trulia Estimate is $5,205,900, with a rent estimate of $7,980/month.

Home Details for 19 Overlook Dr

Interior Features

Interior Details
Basement: Finished,PartialWet Bar
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 6421 Square Feet
Appliances & Utilities
Laundry: Laundry Room
Heating & Cooling
Heating: Natural Gas,Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: TerraceExterior: Gas Grill
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageParking Spaces: 2Parking: Garage Door Opener

Property Information

Year Built
Year Built: 1929Year Renovated: 2021
Property Type / Style
Property Type: ResidentialProperty Subtype: Residential, Single Family ResidenceArchitecture: Tudor
Building
Construction Materials: Stucco
Property Information
Included in Sale: Washer/Dryer, All Kitchen ApplncsParcel Number: 011392/S

Price & Status

Price
List Price: $4,050,000
Status Change & Dates
Off Market Date: Mon Aug 05 2024

Active Status

MLS Status: Closed

Location

Direction & Address
City: Greenwich
School Information
Elementary School: Julian CurtissJr High / Middle School: Central

Building

Building Area
Building Area: 6421 Square Feet

HOA

HOA Name: Milbrook

Lot Information

Lot Area: 0.36 acres

Mobile R/V

Mobile Home Park
Mobile Home Units: Feet

Miscellaneous

BasementMls Number: 120938
Last check for updates: about 16 hours ago
Listed by Jenny Allen, (203) 921-6327
Compass Connecticut, LLC
Bought with: Ellen Mosher, (203) 705-9680, Houlihan Lawrence
Source: Greenwich MLS, Inc., MLS#120938

Price History for 19 Overlook Dr

DatePriceEventSource
09/16/2024$4,350,000Sold
Greenwich MLS, Inc. #120938
08/06/2024$4,050,000PendingGreenwich MLS, Inc. #120938
07/16/2024$4,050,000ContingentGreenwich MLS, Inc. #120938
07/07/2024$4,050,000Listed For SaleGreenwich MLS, Inc. #120938
09/09/2021$3,349,000Sold
Greenwich MLS, Inc. #113865
08/19/2021$3,398,000ContingentSmart MLS #170419010
07/14/2021$3,398,000Listed For SaleSmart MLS #170419010
10/14/2020$2,050,000Sold
N/A
05/30/2019$1,799,000Listed For SaleAgent Provided

Market trends in Greenwich

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.1M
$340KMoM
Sale-to-List Price
102.7%
1.5%MoM
Price per sq ft
$801
$22MoM
Available listings
190
7MoM
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Property Tax and Assessment

Year2025
Tax$27,613
Assessment$2,234,260
Home facts updated by county records

Comparable Sales for 19 Overlook Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
42 Mallard Dr, Greenwich, CT
0.17
Single-Family Home
$4,950,000
08/14/25
5
8
6,000
85 Mallard Dr, Greenwich, CT
0.35
Single-Family Home
$4,350,000
07/03/26
6
6.5
4,053
17 Pintail Ln, Greenwich, CT
0.23
Single-Family Home
$4,271,000
03/16/26
5
4.5
3,643
7 Stanwich Rd, Greenwich, CT
0.46
Single-Family Home
$4,100,000
01/21/26
5
3.5
4,000
24 Annjim Dr, Greenwich, CT
0.69
Single-Family Home
$4,753,000
04/20/26
5
4.5
4,937
68 Orchard Dr, Greenwich, CT
0.59
Single-Family Home
$3,825,000
10/31/25
5
4
4,930
50 North St, Greenwich, CT
0.54
Single-Family Home
$5,250,000
12/15/25
5
5.5
7,569
52 Morningside Dr, Greenwich, CT
0.59
Single-Family Home
$2,995,000
07/31/25
5
4
4,476

Nearby homes

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Assigned Schools

These are the assigned schools for 19 Overlook Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Greenwich

At least 469 Trulia users voted on each feature.

  • 88 % Say it's dog friendly

  • 83 % Say car is needed

  • 77 % Say parking is easy

  • 76 % Say there's holiday spirit

  • 74 % Say people would walk alone at night

  • 73 % Say yards are well-kept

  • 69 % Say kids play outside

  • 67 % Say it's walkable to restaurants

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say it's quiet

  • 60 % Say there are sidewalks

  • 60 % Say there's wildlife

  • 58 % Say neighbors are friendly

  • 57 % Say streets are well-lit

  • 55 % Say it's walkable to grocery stores

  • 45 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Great long walking trails all Over the town, and dog parks! So it is just wonderfully dog friendly. "
    0
    Flag
  • Justine
    "Greenwich car show, dog day out, Bruce museum, proximity to Highway, public beach and pool for Greenwich residents"
    0
    Flag
  • Trulia User
    "School events, country club, cohen civic center, beach, walk-to-town, nice holiday environments, nice neighbors and neighborhoods!"
    0
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  • Dalvesbrito
    "Block party School Halloween party School movie party Fireworks on 4th of July Center civic events "
    0
    Flag
  • Kellysgreensllc
    "There are good schools,parks,library here. Conveniently located near mass transit.Not to forget our beaches. Local restaurants "
    0
    Flag
  • eiji.nishimuras
    "No good dog park to speak of. And generally park regulation and beach regulation is not very dog friendly "
    0
    Flag
  • Sharon Elkayam
    "It is a friendly community where the kids ride bikes and play together. The schools are good. The kids play in the front yards. "
    0
    Flag
  • Jp
    "It’s the best blend of good suburban town systems and support, and easy access to the center of economic opportunity and culture. "
    0
    Flag
  • Stefanie Lacoff, Realtor
    "Many parks and trails to walk your dog. Dogs are allowed at the beach during winter months. Greenwich is a great place to live! "
    1
    Flag
  • Stefanie Lacoff, Realtor
    "Greenwich is diverse and inclusive. People are educated and parents are involved. We have great amenities and resources for our community. "
    0
    Flag
  • Stefanie Lacoff, Realtor
    "Greenwich is a fantastic town to live in and raise a family. It’s great for all ages from kids through seniors. "
    0
    Flag
  • Jmcdg22m5w
    "It’s a quiet and clean neighborhood, I like it a lot. The restaurants are beautiful, the people are friendly, it is an easily accessible place for pharmacies or clothing and accessories stores."
    0
    Flag
  • Trulia User
    "I’ve lived here 25 years and love it. Looking to stay in the area only need a bigger house with no steps."
    1
    Flag
  • Trulia User
    "Great neighborhood! Love it here just looking for something more private single family home on a dead end or curl de sac."
    2
    Flag
  • Trulia User
    "Very dog friendly. Lots of great places to walk with a dog. Many dog owners. The beach in Old Greenwich is a fun place to meet other dog owners and allow them to play."
    0
    Flag
  • Trulia User
    "I95 is the worst and the Merritt parkway are very difficult to commute on. Good luck if you need to commute during peak times. "
    1
    Flag
  • Sharonelkayam
    "Kid and pet friendly. Nice neighbors and well kept homes. The schools are great. Good area for walking and running. Near trains and shopping area in Old Greenwich. Beach is also a few minutes away."
    1
    Flag
  • Sandra
    "Halloween decoration is the best! Neighbors are very nice and safety, kids walk and play safety school is very good"
    0
    Flag
  • Barbara J.
    "Great public and private schools and safe neighborhoods. People are friendly and it’s a great place to raise kids. "
    5
    Flag
  • Charles M.
    "Pretty perfect. Train, buses, the parkway and 95. What’s left? Car pooling! and we have that as well."
    0
    Flag
  • Janette S. A.
    "Family oriented neighborhood with nice parks and sidewalk restaurants. Feel safe going for a walk and at the park. "
    0
    Flag
  • Diane L.
    "The police involvement with their community, the amazing schools and circular activities, the friendly neighborhood, so many other Positive things to say not enough time!"
    4
    Flag
  • Hercoles_silveir4
    "Grande offers better security public transport schools hospital than any other city that my family and I have ever lived in I think a good place to live would recommend to anyone that I like a safe and educated home"
    1
    Flag
  • Daniel C.
    "I need a car most of the time. There’s 2 buses line that serves the town, one takes you to the metro north station "
    0
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  • Trevor M.
    "Love living here!! It is beautiful,safe and fun. Tods point is amazing. Great schools and plenty of things to do!"
    0
    Flag
  • Leila
    "The is very. Nice friendly I like to live in Grreewich because is Quite and gentle I can walk to my dog in the nighttime no danger"
    5
    Flag
  • Lynn M.
    "Busy street traffic, leash mandatory , people drive by fast! Dogs being walked are friendly. People pick up their dog waste. It’s a plus!"
    1
    Flag
  • Allforsummer
    "I grew up in Glenville. It’s a very family oriented neighborhood. Local businesses are owned by neighbors. Kids can ride their bikes freely or take walks to Glenville Pizza. Great place to live! "
    0
    Flag
  • Katetaylor83
    "Yes - there are a number of places close by to walk your dogs. It’s not ideal, as there aren’t a lot of off leash options and the dog run is tiny and unusable. "
    3
    Flag
  • Ksziman
    "Strong sense of community and neighborly support and camaraderie. Folks generally look out for one another "
    3
    Flag
  • Stephanie
    "Yes there are lots of dogs. With lots of parks to walk dogs. Anyone who has a dog would be comfort in. "
    0
    Flag
  • Lynn M.
    "My area is not particularly family friendly. I live in the main avenue. Better suited to working person/s."
    2
    Flag
  • Lesliegodner
    "I’ve lived here for a year. It’s a great neighborhood. We have amazing restaurants and stores. Great for families and singles alike. "
    0
    Flag
  • Jesselynn G.
    "The elementary school fairs/carnivals, trick or treating, fireworks at the park nothing else in particular but overall a great neighborhood "
    0
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  • Mdandola
    "Lots of families in the area and great schools. The town has tons of wonderful programs, and there are great additional programs through YMCA and other organizations in town. The town party is awesome, as well."
    4
    Flag
  • Sarah G.
    "I reverse commute to North Haven—50 mikes away. I have zero traffic and can get to 95 quickly, so that’s a plus. "
    0
    Flag
  • Lynn M.
    "Stores that do not want to allow pets in post signs, most are ok with a quick in and out with a small dog."
    0
    Flag
  • Andrea T.
    "Is very safe has great schools clean streets is near most shops people respect each other I would love rents to be not as expensive forces people to move out "
    0
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  • Gissella E.
    "Safe area to live. Great school with a exceptional , espectacular kids activities and kids friendly and pleasure to live here and grow up your family. Good , good ,good "
    0
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  • Debtifrob
    "This community is as close as you can get to a home town like Father Knows Best or Andy Griffin. With. the exception of the high cost, it's a very warm, exclusive neighborhood with mansions & working class ppl. lots of celebrities move here bc if safety & school system. I was born here & living here 65yrs now. Downfall is the high housing, upside lots if culture & a few beaches, public pool & island a ferry brings you to."
    4
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Explore by feature - Pet Friendly

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28 rentals with an outdoor space in Greenwich, CT

Homes for sale near 19 Overlook Dr

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Off Market Homes Near 19 Overlook Dr

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Listing data courtesy of Greenwich MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS.