23 Greenleaf Ave, Darien, CT 06820
OFF MARKET

23 Greenleaf Ave
Darien, CT 06820

  • 4 Beds
  • 4 Baths
  • 3,221 sqft (on 4.14 acres)

$4,568,400

Trulia Estimate
as of Jun 7, 2026
Est. Refi. Payment $29,369/mo*
Refinance Your Home

$4,568,400

Trulia Estimate
as of Jun 7, 2026
Est. Refi. Payment $29,369/mo*
Refinance Your Home
4 Beds
4 Baths
3,221 sqft
(on 4.14 acres)

Local Information

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

Description

Hidden gem set on Four plus beautiful acres. This 4 bedroom, 3.1 bathroom Colonial is move in condition. This home boasts hardwoods floors throughout, 3 wood burning fireplaces and gorgeous natural light. A spacious sunroom off the main level is the perfect spot to take in the expansive property. Tall oak trees and other mature plantings screen the grounds beautifully. Located in one of Darien's most desirable neighborhoods- close to schools, trains and downtown.
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
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 23 Greenleaf Ave

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Wood
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 4.14 acres

Price History for 23 Greenleaf Ave

DatePriceEventSource
08/03/2022ListingRemovedHoulihan Lawrence Inc
07/09/2022$9,000Listed For RentHoulihan Lawrence Inc #170507070
07/07/2022$2,315,000Sold
Smart MLS #170497846
06/18/2022$2,095,000ContingentSmart MLS #170497846
06/07/2022$2,095,000Listed For SaleSmart MLS #170497846

Market trends in Darien

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
14MoM
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Property Tax and Assessment

Year2025
Tax$25,393
Assessment$1,640,380
Home facts updated by county records

Comparable Sales for 23 Greenleaf Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
178 Christie Hill Road, Darien, CT
0.30
Single-Family Home
$2,150,000
07/31/25
4
4.5
3,436
7 Lantern Lane, Darien, CT
0.47
Single-Family Home
$2,355,000
06/12/25
4
3.5
3,742
76 Deepwood Road, Darien, CT
0.37
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
326 Hollow Tree Ridge Road, Darien, CT
0.15
Single-Family Home
$3,650,000
08/20/25
5
4.5
6,860
26 Holly Lane, Darien, CT
0.53
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
19 Stephanie Lane, Darien, CT
0.68
Single-Family Home
$2,700,000
07/18/25
4
2.5
2,976
15 Waterbury Lane, Darien, CT
0.13
Single-Family Home
$4,400,000
04/28/26
5
5
6,052
39 Deepwood Road, Darien, CT
0.34
Single-Family Home
$4,022,500
08/01/25
5
3.5
4,932
39 Briar Brae Road, Darien, CT
0.60
Single-Family Home
$2,358,000
08/01/25
4
3
3,242
112 Camp Avenue, Darien, CT
0.78
Single-Family Home
$2,395,000
04/15/26
4
3.5
3,550

Nearby homes

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Assigned Schools

These are the assigned schools for 23 Greenleaf Ave.
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 Darien

At least 147 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 89 % Say yards are well-kept

  • 88 % Say parking is easy

  • 87 % Say car is needed

  • 84 % Say there's holiday spirit

  • 81 % Say people would walk alone at night

  • 80 % Say kids play outside

  • 73 % Say there's wildlife

  • 71 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 58 % Say neighbors are friendly

  • 58 % Say there are community events

  • 58 % Say there are sidewalks

  • 55 % Say it's walkable to restaurants

  • 48 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Kimrichardnyc
    "Happy, safe and friendly place to live and raise children. Need more diversification like in wesport CT though. "
    0
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  • Trulia User
    "This is the best town to raise kids and build friendships. The beaches, parks, restaurants, nature and proximity to NYC also makes a great place to live. We have found the people generally friendly and welcoming. "
    0
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  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
    0
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  • Jessica_hatch7
    "NA commute to the city is an easy 65 minute train ride. We have two stations in Darien, both easily accessible. "
    3
    Flag
  • Peter S.
    "Holidays and school events. Dining and activities such as sports, the arts and many many social events"
    0
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  • Mzengo8
    "My neighborhood plays kid lacrosse/ basketball or football games. And we have parties on almost every holiday. Which is very fun for all of the kids on the block "
    0
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  • Bill T.
    "Dead end but on a hill and has a loop so kids can run around, play and explore. Lots of trees and woods surround the neighborhood."
    3
    Flag
  • Tad
    "My commute is five minutes to the train station, five minute walk from parking lot to the tracks, then an hour on the train to grand central each work day. "
    1
    Flag
  • Allison w.
    "They would love it, such a friendly area. Dogs are everywhere and appreciated. I have 2 dogs and I am so glad there are a ton of dogs around. "
    0
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  • Chad W.
    "Darien is as family friendly as it gets. There is a lot of money here. Some are kind, but many are snobby. It's a bit of a bubble, which is why many families move here."
    0
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  • Jessica_hatch7
    "The people are amazing and the schools are fantastic. We are only 60 minutes from the city and the trains run very frequently. "
    2
    Flag
  • Victoria_belluscio
    "Great place to raise children- excellent schools- everything is 5-10 min away so good for busy schedules! 2 train stations for easy commuting, beaches, parks and more!"
    0
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  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
    0
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  • Bill T.
    "Big circle where no cars or trucks visit unless they live here or have business in the neighborhood... great place for kids"
    1
    Flag
  • dwenger
    "Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
    0
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23 Greenleaf Ave, Darien, CT 06820 is a 4 bedroom, 4 bathroom, 3,221 sqft single-family home built in 1955. This property is not currently available for sale. 23 Greenleaf Ave was last sold on Jul 7, 2022 for $2,315,000. The current Trulia Estimate for 23 Greenleaf Ave is $4,568,400.