23 Smith Rd, Greenwich, CT 06830
Property image
Property image
OFF MARKET

$22,620,600

Trulia Estimate
  • 7 Beds
  • 8.5 Baths
  • 8,150 sqft (on 5.60 acres)

23 Smith Rd, Greenwich, CT 06830

Est. Refi. Payment $157,846/mo*
Refinance Your Home
Currently Off Market - Sold May 6, 2021 for $27,750,000

Home Value

Trulia Estimate
$22.6M
Since last month
Increased$1M (+5%)
Since last year
Increased$4M (+20.8%)
Since last sale
Decreased$5M (-18.5%)
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 +123% in the last 10 years
MonthEstimated value
2026
October 2026$22.62M
September 2026$22.52M
August 2026$21.54M
July 2026$19.34M
June 2026$20.63M
May 2026$19.95M
April 2026$19.8M
March 2026$19.99M
February 2026$19.13M
January 2026$18.56M
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
25 Field Point Cir, Greenwich, CT
0.35
Single-Family Home
$16,800,000
08/28/26
6
8
9,565
44 & 40 Mayo Ave, Greenwich, CT
0.40
Single-Family Home
$21,250,000
09/15/26
7
7
18,217
33 Byram Dr, Greenwich, CT
0.69
Single-Family Home
$21,500,000
07/24/26
6
6
6,238
55 Otter Rock Dr, Greenwich, CT
0.51
Single-Family Home
$15,000,000
07/16/26
8
7
10,780
16 Windrose Way, Greenwich, CT
0.77
Single-Family Home
$14,000,000
03/23/26
8
10.5
10,171
33 Meadow Wood Dr, Greenwich, CT
0.70
Single-Family Home
$8,000,000
11/05/25
6
5.5
5,040
197 Otter Rock Dr, Greenwich, CT
0.51
Single-Family Home
$10,623,500
08/13/26
5
5.5
5,277
579 Indian Field Rd, Greenwich, CT
1.10
Single-Family Home
$40,000,000
11/19/25
6
9.5
11,500
553 Indian Field Rd, Greenwich, CT
1.15
Single-Family Home
$19,900,000
06/11/26
4
5.5
5,385
201 Shore Rd, Greenwich, CT
0.55
Single-Family Home
$2,025,000
05/22/26
5
4
3,598

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
17 Smith Rd, Greenwich, CT 06830
0.05
-
-
-
-
Off Market
27 Smith Rd, Greenwich, CT 06830
0.05
$18,033,400
9
12
7,028
Off Market
76 Summit Rd, Greenwich, CT 06830
0.06
$3,337,400
5
4.5
3,477
Off Market
39 Pear Ln, Greenwich, CT 06830
0.07
-
-
-
-
Off Market
9 Smith Rd, Greenwich, CT 06830
0.08
-
Studio
-
-
Off Market
8 Broad Rd, Greenwich, CT 06830
0.09
$9,255,800
5
6
5,671
Off Market
8 Broad Rd, Greenwich, CT 06830
0.09
-
-
-
-
Off Market
26 Broad Rd, Greenwich, CT 06830
0.10
$10,781,400
7
7
9,333
Off Market
52 Pear Ln, Greenwich, CT 06830
0.11
-
4
6
4,495
Off Market
25 Pear Ln, Greenwich, CT 06830
0.11
$12,957,400
8
11
6,228
Off Market
10 Broad Rd, Greenwich, CT 06830
0.12
$13,070,800
6
7
9,286
Off Market
140 Field Point Cir, Greenwich, CT 06830
0.12
$25,033,900
6
6
4,687
Off Market
1 Smith Rd, Greenwich, CT 06830
0.12
-
Studio
-
-
Off Market
48 Pear Ln, Greenwich, CT 06830
0.12
$38,557,200
6
12
9,890
Off Market
15 Pear Ln, Greenwich, CT 06830
0.14
$10,143,000
5
7
8,856
Off Market
50 Pear Ln, Greenwich, CT 06830
0.15
-
Studio
-
-
Off Market
135 Field Point Cir, Greenwich, CT 06830
0.15
$20,086,500
6
7.5
9,856
Off Market
14 Broad Rd, Greenwich, CT 06830
0.16
$11,366,000
5
8
7,771
Off Market
6 Broad Rd, Greenwich, CT 06830
0.16
$9,834,900
6
6
6,290
Off Market
11 Broad Rd, Greenwich, CT 06830
0.16
$7,946,800
6
6.5
6,900
Off Market

Local Information

  • Map ViewExplore the area around 23 Smith Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1937
5.6 acre lot
8,150 sqft
$2,776/sqft
Garage

About this House

Magnificent waterfront estate embraces six exquisitely sculptured acres on a private road with heated pool, guest cottage, oak-paneled barn, gorgeous gardens, dock and extensive shoreline on Greenwich Harbor. Classic elegance untarnished by the passage of time defines renovated/expanded 1937 residence with sophisticated interior design by Cullman and Kravis of New York; 6 fireplaces; panoramic water views; fabulous waterfront terrace. Gracious formal rooms; family room adjoining grand gourmet kitchen with two granite islands; stunning Great Room; 4-season solarium opening to terrace with fireplace. Seven bedrooms include one ideal for guests; children's bunk room; luxury master with fireplace, his/her baths, walk-in custom closet. Home gym; wine room; generator; 4-car garage.
23 Smith Rd, Greenwich, CT 06830 is a 7 bedroom, 9 bathroom, 8,150 sqft single-family home built in 1937. It last sold for $27,750,000 on May 6, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $22,620,600.

Home Details for 23 Smith Rd

Exterior Features

Exterior Home Features
Roof: Slate
Pool
Pool
Parking & Garage
GarageParking Spaces: 4Parking: Garage Detached

Property Information

Year Built
Year Built: 1937
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Interior Features

Interior Details
Attic
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Hot Tub or Spa

Community

Units in Building: 1

Lot Information

Lot Area: 5.60 acres

Price and Tax history

DateEventPrice
May 6, 2021
Source: Greenwich MLS, Inc. #106692
Sold
$27,750,000
Feb 26, 2021
Source: Greenwich MLS, Inc.
ListingRemoved
Nov 12, 2020
Source: Agent Provided
PriceChange
$29,900,000
Price decreased by 24%
May 20, 2019
Source: Agent Provided
Listed For Sale
$39,500,000

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

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

LGBTQ Local Legal Protections

Frequently asked questions about 23 Smith Rd

  • What is 23 Smith Rd estimated to be worth?
    Trulia's estimated value for 23 Smith Rd in Greenwich, CT is $22,620,600.
  • What is the price history for 23 Smith Rd?
    23 Smith Rd in Greenwich, CT last sold for $27,750,000 in May 2021.
  • Is Greenwich a buyer's or seller's market?
    Greenwich is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Greenwich?
    The median sale price in Greenwich is $2.58M. That is up $150K from the prior month.
  • Does 23 Smith Rd have air conditioning?
    Yes, 23 Smith Rd in Greenwich, CT has air conditioning.
  • Does 23 Smith Rd have a pool?
    Yes, 23 Smith Rd in Greenwich, CT has a pool.

Explore by feature - Pet Friendly

41 pet-friendly rentals in Greenwich, CT

Explore by feature - Garage

56 rentals with a garage in Greenwich, CT

Explore by feature - Air Conditioning

136 rentals with air conditioning in Greenwich, CT

Explore by feature - Pool

22 rentals with a pool in Greenwich, CT

Explore by feature - Washer/dryer

108 rentals with a washer/dryer in Greenwich, CT

Explore by feature - Outdoor Space

20 rentals with an outdoor space in Greenwich, CT

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Off Market Homes Near 23 Smith Rd

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