248 Overlook Dr, Greenwich, CT 06830
Property image
Property image
FOR SALE
NEW - 1 DAY AGO
0.49 ACRES

$7,595,000

  • 5 Beds
  • 6.5 Baths
  • 7,700 sqft (on 0.49 acres)

248 Overlook Dr, Greenwich, CT 06830

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Home Highlights

Single-Family Home
Built in 2018
0.49 acre lot
$986/sqft
Garage
HOA $1,592/mo

Local Information

  • Map ViewExplore the area around 248 Overlook Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Outdoor fireplaceBalcony overlooking backyardMorning kitchenRec roomDual walk-in closetsElegant open-concept layout
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.
Last check for updates: about 5 hours ago
Listing courtesy of Joseph Barbieri, (203) 940-2025
Sotheby's International Realty
Source: Greenwich MLS, Inc., MLS#125926
Also Listed on Greenwich MLS, Inc..

Home Details for 248 Overlook Dr

Interior Features

Interior Details
Basement: Exterior Entry,Finished
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 7700 Square Feet
Appliances & Utilities
Laundry: Laundry Room
Heating & Cooling
Heating: Natural Gas,Hydro-AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas
Fireplace & Spa
Number of Fireplaces: 5Has a Fireplace
Windows, Doors, Floors & Walls
Window: Double Pane Windows
Levels, Entrance, & Accessibility
Elevator
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: WoodPatio / Porch: TerraceExterior: Balcony, Gas GrillNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageParking Spaces: 2Parking: Garage

Days on Market

Days on Market: 1

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: ResidentialProperty Subtype: Residential, Single Family Residence
Building
Construction Materials: Shingle Siding
Property Information
Included in Sale: Washer/Dryer, All Kitchen ApplncsParcel Number: 013171/S

Price & Status

Price
List Price: $7,595,000Price Per Sqft: $986

Active Status

MLS Status: Active

Location

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

Agent Information

Listing Agent
Listing ID: 125926

Building

Building Area
Building Area: 7700 Square Feet

HOA

HOA Name: MilbrookHas an HOAHOA Fee: $9,550/Semi-Annually

Lot Information

Lot Area: 0.49 acres

Mobile R/V

Mobile Home Park
Mobile Home Units: Feet

Miscellaneous

BasementMls Number: 125926

Around this home

What Locals Say about Greenwich

At least 470 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
    "Dog friendly"
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag

Market trends in Greenwich

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.58M
$150KMoM
Sale-to-List Price
104.8%
1.0%MoM
Price per sq ft
$825
$1MoM
Available listings
152
30MoM

Home Value

Trulia Estimate
$7.44M
Since last month
Increased$472K (+6.8%)
Since last year
Increased$1M (+21.3%)
Since last sale
Increased$3M (+83.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +319% in the last 10 years
MonthEstimated value
2026
September 2026$7.44M
August 2026$6.96M
July 2026$6.96M
June 2026$7.02M
May 2026$6.89M
April 2026$6.73M
March 2026$6.87M
February 2026$6.42M
January 2026$6.33M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
68 Orchard Dr, Greenwich, CT
0.09
Single-Family Home
$3,825,000
10/31/25
5
4
4,930
85 Mallard Dr, Greenwich, CT
0.26
Single-Family Home
$4,350,000
07/03/26
6
6.5
4,053
151 E Elm St, Greenwich, CT
0.18
Single-Family Home
$4,100,000
03/26/26
5
6
5,000
26 Circle Dr, Greenwich, CT
0.44
Single-Family Home
$3,753,750
08/31/26
4
4.5
5,638
105 Woodside Dr, Greenwich, CT
0.21
Single-Family Home
$6,750,000
06/22/26
6
7.5
7,292
141 Woodside Dr, Greenwich, CT
0.24
Single-Family Home
$3,900,000
11/20/25
4
3.5
3,386
155 E Elm St, Greenwich, CT
0.19
Single-Family Home
$5,695,000
06/17/26
5
6.5
5,506
3 Anderson Rd, Greenwich, CT
0.17
Single-Family Home
$9,000,000
02/09/26
6
8.5
9,845
85 Indian Field Rd, Greenwich, CT
0.59
Single-Family Home
$4,450,000
09/10/26
5
6.5
5,773

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
44 Orchard Dr, Greenwich, CT 06830
0.07
$4,140,300
4
4
3,576
Off Market
68 Orchard Dr, Greenwich, CT 06830
0.09
$4,101,400
5
4
4,930
Off Market
59 Le Grande Ave #11, Greenwich, CT 06830
0.06
$1,814,300
3
3.5
2,482
Off Market
59 Le Grande Ave #15, Greenwich, CT 06830
0.07
$2,131,700
3
3.5
2,482
Off Market
37 Orchard Dr, Greenwich, CT 06830
0.11
$4,480,000
5
5.5
4,329
Off Market
219 Overlook Dr, Greenwich, CT 06830
0.09
$5,875,500
6
6
8,001
Off Market
64 Le Grande Ave, Greenwich, CT 06830
0.09
$1,385,000
6
2
2,077
Recently Sold
16 Orchard Dr, Greenwich, CT 06830
0.13
$3,378,800
4
3.5
3,093
Off Market
31 Anderson Rd, Greenwich, CT 06830
0.12
$5,148,300
5
4.5
5,014
Off Market
7 Orchard Dr, Greenwich, CT 06830
0.15
$5,512,000
4
4.5
3,172
Off Market
9 Cottage Ct, Greenwich, CT 06830
0.12
$1,296,200
2
2
1,376
Off Market

Price and Tax history

DateEventPrice
Sep 23, 2026
Source: Greenwich MLS, Inc. #125926
Listed For Sale
$7,595,000
Jan 30, 2020
Source: Greenwich MLS, Inc. #104809
Sold
$4,060,000
Oct 28, 2019
Source: Agent Provided
ListingRemoved
$4,495,000
Jul 24, 2019
Source: Agent Provided
PriceChange
$4,495,000
Price decreased by 10%
Apr 30, 2019
Source: Agent Provided
PriceChange
$4,995,000
Price decreased by 9%

LGBTQ Local Legal Protections

Joseph Barbieri, Sotheby's International Realty
Agent Phone: (203) 940-2025
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.

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Frequently asked questions about 248 Overlook Dr

  • What is the estimated monthly payment for 248 Overlook Dr?
    Based on a $7,595,000 list price with 20% down at today's rates, the estimated monthly payment for 248 Overlook Dr in Greenwich, CT is approximately $53,301 (about $42,530 principal & interest, $10,696 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 248 Overlook Dr compare to homes in Greenwich?
    248 Overlook Dr in Greenwich, CT is listed at $7,595,000, about 194% above the $2.58M median sale price in Greenwich.
  • What do residents say about Greenwich?
    Residents describe Greenwich, CT as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See homes for sale in Greenwich, CT.
  • What are the closest schools to 248 Overlook Dr?
    The closest schools to 248 Overlook Dr in Greenwich, CT are Central Middle School (rated 8/10), Greenwich High School (rated 10/10), Julian Curtiss School (Pre-K/Elementary, rated 7/10).
  • Does 248 Overlook Dr have air conditioning?
    Yes, 248 Overlook Dr in Greenwich, CT has air conditioning.
  • Does 248 Overlook Dr have laundry facilities?
    Yes, 248 Overlook Dr in Greenwich, CT has laundry facilities.
248 Overlook Dr, Greenwich, CT 06830 is a 5 bedroom, 7 bathroom, 7,700 sqft single-family home built in 2018. This property is currently available for sale and was listed by Greenwich MLS, Inc. on Sep 23, 2026. The MLS # for this home is MLS# 125926.