21 Flagler Dr, Greenwich, CT 06830
OFF MARKET

21 Flagler Dr
Greenwich, CT 06830

  • 4 Beds
  • 4 Baths
  • 3,176 sqft (on 2.40 acres)

$6,001,500

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $38,465/mo*
Refinance Your Home

$6,001,500

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $38,465/mo*
Refinance Your Home
4 Beds
4 Baths
3,176 sqft
(on 2.40 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Exceptional parklike grounds of 2.4 acres with lovely gardens and a rolling meadow surround this charming 1930s Colonial home with a heated pool on this favorite lane with an all??e of stately trees close to the North Street School. A broad circular driveway leads to the entrance. The portico with lovely carved detailing and arched coins has intricate leaded glass in the fanlight and the door has classic raised panels. The center hall has exceptional random-width, wide-board, hobnailed floors which continue into the living room with a fireplace, nice proportions, east and west exposures and french doors to the solarium with glass on three sides overlooking the gardens. The dining room is formal with two exposures including a large west-facing bow window and the inviting library has two exposures and a bathroom. The country kitchen has wonderful cabinetry, and the family room with a fireplace and a beamed ceiling opens to the verandah, beyond which is the pool, plus there is a changing room, the laundry and the two-car garage. Upstairs is a lovely master bedroom with a fireplace, three exposures, two window seats and a bathroom. There are three additional bedrooms, two bathrooms, back stairs and a third-floor office with a powder room.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 21 Flagler Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 15
Heating & Cooling
Heating: Forced AirAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1932Year Updated: 1995
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.40 acres

Price History for 21 Flagler Dr

DatePriceEventSource
04/16/2012$2,425,000Sold
Greenwich MLS, Inc. #80883
01/25/2012$2,975,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$37,282
Assessment$3,096,520
Home facts updated by county records

Comparable Sales for 21 Flagler Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
512 North St, Greenwich, CT
0.36
Single-Family Home
$3,999,000
06/13/25
5
4.5
4,078
5 Wooddale Rd, Greenwich, CT
0.63
Single-Family Home
$3,525,000
10/10/25
4
3.5
3,978
81 Clapboard Ridge Rd, Greenwich, CT
0.18
Single-Family Home
$5,300,000
01/29/26
5
4.5
5,126
14 Pinecroft Rd, Greenwich, CT
0.61
Single-Family Home
$5,550,000
04/23/26
4
3.5
4,304
80 Sawmill Ln, Greenwich, CT
0.54
Single-Family Home
$3,550,000
06/16/25
4
4.5
3,986
15 Red Coat Ln, Greenwich, CT
0.85
Single-Family Home
$2,575,000
08/18/25
5
4
3,837
65 Perkins Rd, Greenwich, CT
0.80
Single-Family Home
$3,700,000
03/06/26
4
4.5
4,687
8 Stoney Wylde Ln, Greenwich, CT
0.59
Single-Family Home
$4,600,000
05/31/25
5
5.5
5,022
12 Joshua Ln, Greenwich, CT
0.73
Single-Family Home
$3,425,000
03/23/26
4
3
2,977
12 Wooddale Rd, Greenwich, CT
0.52
Single-Family Home
$4,450,000
04/09/26
5
5.5
4,852

Nearby homes

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Assigned Schools

These are the assigned schools for 21 Flagler 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 464 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.
  • 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
  • Rebecca
    "People r always out walking their dogs. Cars know they have the right of way and will either slow or go around completely "
    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
  • Ryan S.
    "Rarely anything and the things they do have are usually very expensive. Wish there were more things to do to build the community. "
    0
    Flag
  • Msuppodvm
    "Many special events around families and children. Many resources available for families and kids. Excellent afternoon programs, many sports programs. "
    0
    Flag

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21 Flagler Dr, Greenwich, CT 06830 is a 4 bedroom, 4 bathroom, 3,176 sqft single-family home built in 1932. This property is not currently available for sale. 21 Flagler Dr was last sold on Apr 16, 2012 for $2,425,000. The current Trulia Estimate for 21 Flagler Dr is $6,001,500.