59 Hillside Dr, Greenwich, CT 06830
Property image
Property image
PENDING
0.36 ACRES

$4,995,000

  • 5 Beds
  • 6 Baths
  • 6,108 sqft (on 0.36 acres)

59 Hillside Dr, Greenwich, CT 06830

Est. Mortgage $32,842/mo*
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Home Highlights

Property Type
Single-Family Home
Year Built
2012
Lot Size
0.36 acres
Price/Sqft
$818
Parking
Garage

Local Information

  • Map ViewExplore the area around 59 Hillside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Elegant and thoughtfully designed, this exceptional 5-bedroom, 5-full and 2-half bath residence offers approximately 6,000 square feet of beautifully appointed living space in central Greenwich. Generously scaled public rooms and an effortless floor plan create an ideal setting for both everyday living and sophisticated entertaining. The gourmet kitchen opens to inviting living spaces and outdoor terraces with fireplace, surrounded by beautifully landscaped grounds. Five en-suite bedrooms provide privacy and comfort. The entire top floor offers a versatile office suite with room for multiple workspaces. A lower-level entertainment area with bar, wine cellar, and gym completes the home. Ideally located near Greenwich's top schools, downtown shopping, restaurants and train station.
Last check for updates: about 16 hours ago
Listing courtesy of Alison Leigh, (203) 667-7832
Brown Harris Stevens CT, LLC
Source: Greenwich MLS, Inc., MLS#125651
Also Listed on Greenwich MLS, Inc., Halstead / Brown Harris Stevens.

Home Details for 59 Hillside Dr

Interior Features

Interior Details
Basement: Finished
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 7Number of Bathrooms (full): 5Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 6108 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: 2Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: TerraceFencing: FencedNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1Has a GarageParking Spaces: 1Parking: Garage

Days on Market

Days on Market: 21

Property Information

Year Built
Year Built: 2012
Property Type / Style
Property Type: ResidentialProperty Subtype: Residential, Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Clapboard
Property Information
Included in Sale: Washer/Dryer, All Kitchen ApplncsParcel Number: 072061/S

Price & Status

Price
List Price: $4,995,000Price Per Sqft: $818
Status Change & Dates
Off Market Date: Tue Aug 18 2026

Active Status

MLS Status: Pending

Location

Direction & Address
City: Greenwich
School Information
Elementary School: North StreetJr High / Middle School: Central

Agent Information

Listing Agent
Listing ID: 125651

Building

Building Area
Building Area: 6108 Square Feet

Lot Information

Lot Area: 0.36 acres

Mobile R/V

Mobile Home Park
Mobile Home Units: Feet

Miscellaneous

BasementMls Number: 125651

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 July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.44M
$338KMoM
Sale-to-List Price
103.8%
1.1%MoM
Price per sq ft
$825
$24MoM
Available listings
182
8MoM

Home Value

Trulia Estimate
$5.19M
Since last month
Increased$95K (+1.9%)
Since last year
Increased$582K (+12.6%)
Since last sale
Increased$3M (+96.5%)
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 +97% in the last 10 years
MonthEstimated value
2026
August 2026$5.2M
August 2026$5.2M
July 2026$5.11M
June 2026$5.15M
May 2026$5.13M
April 2026$5M
March 2026$4.98M
February 2026$4.79M
January 2026$4.7M
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
46 Hillside Dr, Greenwich, CT
0.07
Single-Family Home
$2,715,000
08/06/26
6
3.5
2,901
16 Martin Dale N, Greenwich, CT
0.24
Single-Family Home
$5,450,000
05/14/26
6
7
5,590
37 Ridgeview Ave, Greenwich, CT
0.36
Single-Family Home
$2,800,000
12/12/25
4
4.5
2,182
50 North St, Greenwich, CT
0.24
Single-Family Home
$5,250,000
12/15/25
5
5.5
7,569
10 Echo Ln, Greenwich, CT
0.26
Single-Family Home
$4,000,000
06/24/26
4
3.5
3,457
200 Old Church Rd, Greenwich, CT
0.36
Single-Family Home
$3,100,000
08/03/26
4
3.5
4,366
22 Carleton St, Greenwich, CT
0.76
Single-Family Home
$4,487,500
01/09/26
5
6.5
5,005
191 North St, Greenwich, CT
0.23
Single-Family Home
$4,700,000
02/12/26
4
4.5
4,156
69 Fairfield Rd, Greenwich, CT
0.75
Single-Family Home
$2,875,000
09/30/25
5
5
5,320
40 Ridgeview Ave, Greenwich, CT
0.39
Single-Family Home
$5,675,000
05/08/26
5
6.5
5,473

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
10 Francine Dr, Greenwich, CT 06830
0.08
$6,178,000
6
5
5,133
Off Market
6 Francine Dr, Greenwich, CT 06830
0.08
$4,256,500
4
3.5
2,962
Off Market
46 Hillside Dr, Greenwich, CT 06830
0.07
$2,715,000
6
3.5
2,901
Recently Sold
139 North St, Greenwich, CT 06830
0.09
$8,523,600
5
6.5
8,646
Off Market
1 Lita Dr, Greenwich, CT 06830
0.13
$3,160,600
4
3.5
2,805
Off Market
98 North St, Greenwich, CT 06830
0.17
$5,458,000
5
5.5
4,506
Off Market
1 Martin Dale, Greenwich, CT 06830
0.18
$8,768,400
6
7
-
Off Market
2 Martin Dl, Greenwich, CT 06830
0.21
$6,824,400
4
6
6,902
Off Market
51 North St, Greenwich, CT 06830
0.22
$4,623,400
7
4.5
5,535
Off Market
11 Martin Dale Dale North, Greenwich, CT 06830
0.22
$7,544,700
6
8
8,616
Off Market
50 North St, Greenwich, CT 06830
0.24
$5,250,000
5
5.5
7,569
Recently Sold
24 Martin Dale, Greenwich, CT 06830
0.24
$3,811,100
5
3.5
3,038
Off Market

Price and Tax history

DateEventPrice
Aug 19, 2026
Source: Greenwich MLS, Inc. #125651
Pending
$4,995,000
Aug 11, 2026
Source: Halstead / Brown Harris Stevens #125651
Listed For Sale
$4,995,000
Oct 23, 2013
Source: Greenwich MLS, Inc. #84003
Sold
$2,647,500
May 22, 2013
Source: Agent Provided
PriceChange
$2,988,000
Price increased by 3%
Jan 12, 2013
Source: Agent Provided
Listed For Sale
$2,895,000

LGBTQ Local Legal Protections

Alison Leigh, Brown Harris Stevens CT, LLC
Agent Phone: (203) 667-7832
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 59 Hillside Dr

  • What is the estimated monthly payment for 59 Hillside Dr?
    Based on a $4,995,000 list price with 20% down at today's rates, the estimated monthly payment for 59 Hillside Dr in Greenwich, CT is approximately $33,417 (about $26,307 principal & interest, $7,035 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 59 Hillside Dr compare to homes in Greenwich?
    59 Hillside Dr in Greenwich, CT is listed at $4,995,000, about 105% above the $2.44M 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 59 Hillside Dr?
    The closest schools to 59 Hillside Dr in Greenwich, CT are Central Middle School (rated 8/10), Greenwich High School (rated 10/10), North Street School (Pre-K/Elementary, rated 9/10).
  • Does 59 Hillside Dr have air conditioning?
    Yes, 59 Hillside Dr in Greenwich, CT has air conditioning.
  • Does 59 Hillside Dr have laundry facilities?
    Yes, 59 Hillside Dr in Greenwich, CT has laundry facilities.
59 Hillside Dr, Greenwich, CT 06830 is a 5 bedroom, 7 bathroom, 6,108 sqft single-family home built in 2012. This property is currently available for sale and was listed by Greenwich MLS, Inc. on Aug 11, 2026. The MLS # for this home is MLS# 125651.