240 Overlook Dr, Greenwich, CT 06830
Property image
Property image
OFF MARKET

240 Overlook Dr
Greenwich, CT 06830

  • 5 Beds
  • 5 Baths
  • 6,591 sqft (on 0.80 acres)

$6,038,600

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $38,891/mo*
Refinance Your Home

$6,038,600

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $38,891/mo*
Refinance Your Home
5 Beds
5 Baths
6,591 sqft
(on 0.80 acres)

Local Information

  • Map ViewExplore the area around 240 Overlook Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Secluded in the beautiful, private Milbrook Association, this stately 2005 colonial embraces a gorgeous one-half acre landscape punctuated by lovely fragrant gardens, stone walls and a fabulous in-ground spa with waterfall. Exceptional quality craftsmanship, detailed millwork, extensive built-ins and rich oak flooring distinguish the stylish interior. A front-to-back entry hall introducing generously scaled principal rooms leads to a gracious terrace for seasonal entertaining. Fireplaces enhance the elegant living room, a wonderful family room with French doors to the terrace and a spacious media/game room on the lower level with exterior access. A formal dining room, granite-appointed center-isle gourmet kitchen with breakfast area, handsome cherry paneled library, five bedrooms, four baths and two powder rooms complete the layout. The luxurious master suite with a marble bath includes two large walk-in custom closets. The idyllic setting in the heart of town is within walking distance to the Milbrook Club, shops, schools and the train station. There is potential for expansion.
240 Overlook Dr, Greenwich, CT 06830 is a 5 bedroom, 6 bathroom, 6,591 sqft single-family home built in 2005. It last sold for $3,400,000 on Jun 15, 2012. It is currently off market. The Trulia Estimate is $6,038,600, with a rent estimate of $26,204/month.

Home Highlights

Parking
Garage
Outdoor
Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 240 Overlook Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 15
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Wood
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2005Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.80 acres

Price History for 240 Overlook Dr

DatePriceEventSource
06/15/2012$3,400,000Sold
Greenwich MLS, Inc. #80376
02/11/2012$3,775,000Listed For SaleAgent Provided
09/23/2005$3,825,000Sold
N/A
11/17/2003$1,400,000Sold
N/A
06/09/1998$850,000Sold
N/A

Market trends in Greenwich

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.76M
$257KMoM
Sale-to-List Price
101.2%
1.0%MoM
Price per sq ft
$779
$4MoM
Available listings
183
8MoM
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Property Tax and Assessment

Year2025
Tax$29,480
Assessment$2,385,320
Home facts updated by county records

Comparable Sales for 240 Overlook Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
68 Orchard Dr, Greenwich, CT
0.10
Single-Family Home
$3,825,000
10/31/25
5
4
4,930
16 Orchard Dr, Greenwich, CT
0.12
Single-Family Home
$3,150,000
09/09/25
4
3.5
3,093
131 Woodside Dr, Greenwich, CT
0.22
Single-Family Home
$4,110,000
04/09/26
4
3.5
4,161
141 Woodside Dr, Greenwich, CT
0.25
Single-Family Home
$3,900,000
11/20/25
4
3.5
3,386
52 Morningside Dr, Greenwich, CT
0.35
Single-Family Home
$2,995,000
07/31/25
5
4
4,476
151 E Elm St, Greenwich, CT
0.18
Single-Family Home
$4,100,000
03/26/26
5
6
5,000
18 Woodside Dr, Greenwich, CT
0.52
Single-Family Home
$3,600,000
12/15/25
4
5
3,532
105 Woodside Dr, Greenwich, CT
0.22
Single-Family Home
$6,750,000
06/22/26
6
7.5
7,292
44 W Brother Dr, Greenwich, CT
0.37
Single-Family Home
$7,875,000
09/22/25
7
7
6,337
42 Mallard Dr, Greenwich, CT
0.40
Single-Family Home
$4,950,000
08/14/25
5
8
6,000

Nearby homes

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Assigned Schools

These are the assigned schools for 240 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 468 Trulia users voted on each feature.

  • 88 % Say it's dog friendly

  • 82 % Say car is needed

  • 77 % Say parking is easy

  • 76 % Say there's holiday spirit

  • 73 % Say yards are well-kept

  • 73 % Say people would walk alone at night

  • 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
    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
  • 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
    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

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Homes for sale near 240 Overlook Dr

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Off Market Homes Near 240 Overlook Dr

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