22 Greenleaf Ave, Darien, CT 06820
Property image
Property image
OFF MARKET

22 Greenleaf Ave
Darien, CT 06820

  • 5 Beds
  • 4 Baths
  • 3,542 sqft (on 1.32 acres)

$3,939,000

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $25,747/mo*
Refinance Your Home

$3,939,000

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $25,747/mo*
Refinance Your Home
5 Beds
4 Baths
3,542 sqft
(on 1.32 acres)

Home Value

Trulia Estimate
$3.94M
Since last month
Decreased$3K (-0.1%)
Since last year
Increased$379K (+10.7%)
Since last sale
Increased$2M (+101.1%)
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 +64% in the last 10 years
MonthEstimated value
2026
August 2026$3.92M
July 2026$3.92M
June 2026$3.99M
May 2026$3.85M
April 2026$3.87M
March 2026$3.82M
February 2026$3.67M
January 2026$3.58M
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
76 Deepwood Road, Darien, CT
0.27
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
3 Hickory Lane, Darien, CT
0.21
Single-Family Home
$2,875,000
07/01/26
4
4
2,920
26 Holly Lane, Darien, CT
0.52
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
15 Waterbury Lane, Darien, CT
0.20
Single-Family Home
$4,400,000
04/28/26
5
5
6,052
29 Hillcrest Avenue, Darien, CT
0.41
Single-Family Home
$3,352,000
08/19/26
5
3.5
3,621
16 Libby Lane, Darien, CT
0.48
Single-Family Home
$2,976,000
06/24/26
4
4.5
2,928
261 Hollow Tree Ridge Road, Darien, CT
0.28
Single-Family Home
$4,350,000
12/15/25
5
5.5
6,135
300 Hollow Tree Ridge Road, Darien, CT
0.16
Single-Family Home
$4,900,000
09/02/25
5
7
6,118
3 Revere Road, Darien, CT
0.46
Single-Family Home
$2,350,000
05/01/26
5
3
3,395
8 Haskell Ln, Darien, CT
0.29
Single-Family Home
$4,750,000
06/22/26
6
5
6,810

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
8 Windsor Road, Darien, CT 06820
0.08
$2,942,300
5
3
3,028
Off Market
300 Hollow Tree Ridge Road, Darien, CT 06820
0.16
$5,209,000
5
7
6,118
Off Market
326 Hollow Tree Ridge Road, Darien, CT 06820
0.17
$3,882,200
5
4.5
6,860
Off Market
3 Hickory Lane, Darien, CT 06820
0.21
$2,875,000
4
4
2,920
Recently Sold
15 Waterbury Lane, Darien, CT 06820
0.20
$4,400,000
5
5
6,052
Recently Sold
39 Deepwood Road, Darien, CT 06820
0.21
$4,281,500
5
3.5
4,932
Off Market
345 Hollow Tree Ridge Road, Darien, CT 06820
0.22
$100,000
4
2.5
2,913
Recently Sold
1 Hickory Lane, Darien, CT 06820
0.24
$2,684,200
4
3.5
3,094
Off Market
18 Wee Burn Lane, Darien, CT 06820
0.24
$5,416,600
6
6
6,936
Off Market
280 Hollow Tree Ridge Road, Darien, CT 06820
0.25
$4,324,100
5
5
5,579
Off Market
76 Deepwood Road, Darien, CT 06820
0.27
$2,287,500
5
4
3,897
Recently Sold
261 Hollow Tree Ridge Road, Darien, CT 06820
0.28
$4,350,000
5
5.5
6,135
Recently Sold

Local Information

  • Map ViewExplore the area around 22 Greenleaf Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1956
Lot Size
1.32 acres
Living Area
3,542 sqft
Price/Sqft
$1,112
Parking
Garage

About this House

This 5BR colonial is located on one of the most private & desirable streets in Darien offering light & airy space throughout with fabulous oversized rooms and great flow for entertaining. Also known as Bumpalong, this picturesque private road is located close to MMS, DHS & Noroton train station & is a convenient & easy commute to NYC. Brand-new kitchen with high end appliances, granite counters, new hand-finished hardwood oak floors. The eating area, casual space & DR all flow from the expansive kitchen making entertaining easy & fun. The downstairs finished area features a playroom with addl'l fireplace, & unfinished space for storage. Over 1 acre of land surrounded by mature trees provides wooded privacy & tranquil views of nature.
22 Greenleaf Ave, Darien, CT 06820 is a 5 bedroom, 4 bathroom, 3,542 sqft single-family home built in 1956. It last sold for $1,950,000 on Mar 1, 2013. It is currently off market. The Trulia Estimate is $3,939,000, with a rent estimate of $17,440/month.

Home Details for 22 Greenleaf Ave

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9Types of Rooms: Recreation Room
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1956Year Updated: 2013
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 1.32 acres

Price and Tax history

DateEventPrice
Mar 1, 2013
Source: Smart MLS #99007674
Sold
$1,950,000
Jan 4, 2013
Source: Agent Provided
PriceChange
$1,975,000
Price decreased by 8%
Oct 16, 2012
Source: Agent Provided
Listed For Sale
$2,150,000

Market trends in Darien

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.98M
$246KMoM
Sale-to-List Price
108.9%
3.3%MoM
Price per sq ft
$800
$12MoM
Available listings
36
18MoM

Around this home

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

  • 82 % 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
    Flag
  • 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
    Flag
  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
    0
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 22 Greenleaf Ave

  • What is 22 Greenleaf Ave estimated to be worth?
    Trulia's estimated value for 22 Greenleaf Ave in Darien, CT is $3,939,000.
  • What is the price history for 22 Greenleaf Ave?
    22 Greenleaf Ave in Darien, CT last sold for $1,950,000 in March 2013.
  • Is Darien a buyer's or seller's market?
    Darien is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Darien?
    The median sale price in Darien is $2.98M. That is up $246K from the prior month.
  • Does 22 Greenleaf Ave have a pool?
    Yes, 22 Greenleaf Ave in Darien, CT has a pool.
  • How big is the lot at 22 Greenleaf Ave?
    The lot at 22 Greenleaf Ave in Darien, CT is about 1.3 acres.

Explore by feature - Pet Friendly

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