23 Chieftans Rd, Greenwich, CT 06831
OFF MARKET

23 Chieftans Rd
Greenwich, CT 06831

  • 4 Beds
  • 3.5 Baths
  • 5,999 sqft (on 0.87 acres)

$2,522,100

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $16,593/mo*
Refinance Your Home

$2,522,100

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $16,593/mo*
Refinance Your Home
4 Beds
3.5 Baths
5,999 sqft
(on 0.87 acres)

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
2002
Lot Size
0.87 acres
Living Area
5,999 sqft
Price/Sqft
$420
Parking
Garage
HOA
$2,300/Monthly

About this House

Stunning partially stone and shingle four-bedroom Manor with expansive terrace graces a manicured .87 acre with possible pool site on cul-de-sac in coveted, gated Chieftans community. Dramatic double height entry introduces a gracious floor plan, designed for entertaining and casual living with high ceilings, oak wood floors and custom detailing. Elegant formal rooms, granite-clad eat-in kitchen, adjacent family room with fireplace and office/den comprise main level. Second floor offers primary suite with fireplace, and dual walk-in closets, en-suite bedroom, two bedrooms, full bath and second family room. Top floor provides playroom or office and finished lower level with additional 508 sqft includes family room and wine cellar. Attached three-car garage. One of only 28 homes on 96 acres with 24/7 security.
23 Chieftans Rd, Greenwich, CT 06831 is a 4 bedroom, 4 bathroom, 5,999 sqft single-family home built in 2002. It last sold for $3,450,000 on Oct 16, 2024 (10% below the $3,850,000 asking price). It is currently off market. The Trulia Estimate is $2,522,100.

Home Details for 23 Chieftans Rd

Interior Features

Interior Details
Basement: Full,Partially Finished
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5999 Square Feet
Appliances & Utilities
Utilities: PropaneLaundry: Laundry Room
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace
Security
Security: Security Guard, Security System

Exterior Features

Exterior Home Features
Roof: SlatePatio / Porch: TerraceNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Has a GarageParking Spaces: 3Parking: Garage
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 2002Year Renovated: 2018
Property Type / Style
Property Type: ResidentialProperty Subtype: Residential, Single Family ResidenceArchitecture: English Manor
Building
Construction Materials: Shingle Siding, Stone
Property Information
Included in Sale: Call LBParcel Number: 103603

Price & Status

Price
List Price: $3,850,000
Status Change & Dates
Off Market Date: Thu Aug 08 2024

Active Status

MLS Status: Closed

Location

Direction & Address
City: Greenwich
School Information
Elementary School: ParkwayJr High / Middle School: Western

Building

Building Area
Building Area: 5999 Square Feet

HOA

HOA Name: ChieftansHas an HOAHOA Fee: $2,300/Monthly

Lot Information

Lot Area: 0.87 acres

Mobile R/V

Mobile Home Park
Mobile Home Units: Feet

Miscellaneous

BasementMls Number: 120971
Last check for updates: about 18 hours ago
Listed by Julie Church, (203) 561-9373
Houlihan Lawrence
Bought with: Martha Jeffrey, (203) 964-7800, Sotheby's International Realty
Source: Greenwich MLS, Inc., MLS#120971

Price History for 23 Chieftans Rd

DatePriceEventSource
10/16/2024$3,450,000Sold
Greenwich MLS, Inc. #120971
08/08/2024$3,850,000PendingGreenwich MLS, Inc. #120971
07/26/2024$3,850,000ContingentGreenwich MLS, Inc. #120971
07/09/2024$3,850,000Listed For SaleGreenwich MLS, Inc. #120971

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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Comparable Sales for 23 Chieftans Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
8 Chieftans Rd, Greenwich, CT
0.25
Single-Family Home
$4,370,000
06/11/26
5
8.5
10,640
2 Legendary Circle, Port Chester, NY
0.27
Single-Family Home
$1,550,000
07/14/26
4
2.5
3,148
107 Stonehedge Drive North, Greenwich, CT
0.78
Single-Family Home
$2,000,000
03/13/26
4
3
3,814
39 High Point Circle, Port Chester, NY
0.37
Single-Family Home
$1,350,000
08/27/25
4
3.5
4,018
9 Meeting House Lane, Port Chester, NY
0.28
Single-Family Home
$1,500,000
07/15/26
3
3.5
3,886
29 Fellowship Lane, Port Chester, NY
0.43
Single-Family Home
$1,475,000
10/30/25
4
3.5
3,662
311 Riversville Rd, Greenwich, CT
0.83
Single-Family Home
$3,100,000
06/22/26
4
3.5
3,915
22 Bellefair Road, Pt Chester, NY
0.42
Single-Family Home
$1,430,000
08/25/25
4
2.5
3,318

Nearby homes

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Assigned Schools

These are the assigned schools for 23 Chieftans Rd.
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
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  • Kellysgreensllc
    "There are good schools,parks,library here. Conveniently located near mass transit.Not to forget our beaches. Local restaurants "
    0
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  • eiji.nishimuras
    "No good dog park to speak of. And generally park regulation and beach regulation is not very dog friendly "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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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Homes for sale near 23 Chieftans Rd

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Off Market Homes Near 23 Chieftans Rd

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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.