20 Chieftans Rd, Greenwich, CT 06831
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Property image
OFF MARKET

$3,048,200

Trulia Estimate
  • 4 Beds
  • 6 Baths
  • 4,995 sqft (on 1.08 acres)

20 Chieftans Rd, Greenwich, CT 06831

Est. Refi. Payment $20,103/mo*
Refinance Your Home
Currently Off Market - Sold Mar 3, 2021 for $2,450,000

Home Value

Trulia Estimate
$3.05M
Since last month
Increased$55K (+1.8%)
Since last year
Decreased$304K (-9.1%)
Since last sale
Increased$598K (+24.4%)
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 decreased by -4% in the last 10 years
MonthEstimated value
2026
August 2026$3.05M
August 2026$3.03M
July 2026$2.99M
June 2026$2.97M
May 2026$3.1M
April 2026$3.17M
March 2026$3.18M
February 2026$3.33M
January 2026$3.03M
2025

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
8 Chieftans Rd, Greenwich, CT
0.33
Single-Family Home
$4,370,000
06/11/26
5
8.5
10,640
7 Honeysuckle Lane, Port Chester, NY
0.47
Single-Family Home
$2,395,000
11/24/25
4
5.5
4,889
1050 King St, Greenwich, CT
0.60
Single-Family Home
$1,920,000
11/03/25
4
4
3,264
107 Stonehedge Drive North, Greenwich, CT
0.72
Single-Family Home
$2,000,000
03/13/26
4
3
3,814
9 Meeting House Lane, Port Chester, NY
0.22
Single-Family Home
$1,500,000
07/15/26
3
3.5
3,886
12 Mansion Pl, Greenwich, CT
0.74
Single-Family Home
$1,700,000
09/12/25
4
3.5
2,730
2 Legendary Circle, Port Chester, NY
0.29
Single-Family Home
$1,550,000
07/14/26
4
2.5
3,148
29 Fellowship Lane, Port Chester, NY
0.41
Single-Family Home
$1,475,000
10/30/25
4
3.5
3,662

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
21 Chieftans Rd, Greenwich, CT 06831
0.03
$3,168,400
4
6
6,708
Off Market
22 Chieftans Rd, Greenwich, CT 06831
0.07
$2,993,900
5
7.5
6,033
Off Market
23 Chieftans Rd, Greenwich, CT 06831
0.09
$2,510,800
4
3.5
5,999
Off Market
12 Chieftans Road, Greenwich, CT 06831
0.11
$2,196,500
4
4.5
4,140
Off Market
1 Chieftans Rd, Greenwich, CT 06831
0.14
$3,295,500
4
6
6,481
Off Market
2 Chieftans Rd, Greenwich, CT 06831
0.15
$3,745,900
4
6
7,705
Off Market
27 Chieftans Rd, Greenwich, CT 06831
0.15
$3,343,200
4
6
6,020
Off Market
4 Chieftans Rd, Greenwich, CT 06831
0.17
$2,516,500
3
4.5
4,810
Off Market
1099 King St, Greenwich, CT 06831
0.14
$1,551,400
4
3
1,924
Off Market
26 Reunion Road, Port Chester, NY 10573
0.17
$1,065,500
2
3.5
3,145
Recently Sold
70 Sherwood Ave, Greenwich, CT 06831
0.23
$5,136,500
5
7
7,727
Off Market

Local Information

  • Map ViewExplore the area around 20 Chieftans Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2000
1.08 acre lot
4,995 sqft
$610/sqft
Garage

About this House

Classic stone and shingle manor home located in the prestigious, gated community of Chieftans. This home is privately nestled on a peaceful cul-de-sac. Dramatic 2 story entry opens to spacious public rooms and bright gourmet kitchen. 1st Floor Master w/French doors to Terrace. Luxury Bath, his & her closets. 3 ensuite bedrooms plus a bonus room and mahogany study complete the 2nd floor. Lower Level is fully built out with bar, gym, family room/media area, lounge room, play room, full bath and mudroom with access to outdoors.
20 Chieftans Rd, Greenwich, CT 06831 is a 4 bedroom, 7 bathroom, 4,995 sqft single-family home built in 2000. It last sold for $2,450,000 on Mar 3, 2021 (6% below the $2,595,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,048,200.
Last check for updates: about 9 hours ago
Listed by Leslie Carlotti, (203) 536-8505
Houlihan Lawrence
Bought with: Kori Sassower, (914) 727-0169, Compass Connecticut, LLC
Source: Greenwich MLS, Inc., MLS#111528

Home Details for 20 Chieftans Rd

Interior Features

Interior Details
Basement: Finished
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 7Number of Bathrooms (full): 5Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 4995 Square Feet
Appliances & Utilities
Utilities: PropaneLaundry: Laundry Room
Heating & Cooling
Heating: Hydro-Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hydro Air
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace
Security
Security: Security Guard

Exterior Features

Exterior Home Features
Roof: SlatePatio / Porch: Terrace, DeckNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageParking Spaces: 2Parking: Garage
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 2000Year Renovated: 2001
Property Type / Style
Property Type: ResidentialProperty Subtype: Residential, Single Family ResidenceArchitecture: English Manor
Property Information
Included in Sale: Washer/Dryer, All Kitchen ApplncsParcel Number: 103606

Price & Status

Price
List Price: $2,595,000
Status Change & Dates
Off Market Date: Fri Jan 15 2021

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 4995 Square Feet

HOA

HOA Name: ChieftansHas an HOA

Lot Information

Lot Area: 1.08 Acres

Mobile R/V

Mobile Home Park
Mobile Home Units: Feet

Miscellaneous

BasementMls Number: 111528

Additional Information

HOA Amenities: Gated

Price and Tax history

DateEventPrice
Mar 3, 2021
Source: Greenwich MLS, Inc. #111528
Sold
$2,450,000
Jul 1, 2013
Source: Greenwich MLS, Inc. #83994
Sold
$2,300,000

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

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

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.

Frequently asked questions about 20 Chieftans Rd

  • What is 20 Chieftans Rd estimated to be worth?
    Trulia's estimated value for 20 Chieftans Rd in Greenwich, CT is $3,048,200.
  • What is the price history for 20 Chieftans Rd?
    20 Chieftans Rd in Greenwich, CT last sold for $2,450,000 in March 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 $2.44M. That is up $338K from the prior month.
  • Does 20 Chieftans Rd have air conditioning?
    Yes, 20 Chieftans Rd in Greenwich, CT has air conditioning.
  • Does 20 Chieftans Rd have laundry facilities?
    Yes, 20 Chieftans Rd in Greenwich, CT has laundry facilities.

Explore by feature - Pet Friendly

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