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

65 Greenleaf Ave
Darien, CT 06820

  • 4 Beds
  • 3.5 Baths
  • 5,350 sqft (on 1 acre)

$4,129,200

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $26,574/mo*
Refinance Your Home

$4,129,200

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $26,574/mo*
Refinance Your Home
4 Beds
3.5 Baths
5,350 sqft
(on 1 acre)

Local Information

  • Map ViewExplore the area around 65 Greenleaf Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

GORGEOUS HOME IN A WONDERFUL LOCATION on a quiet street - walk to elementary, middle and high schools. This bright and completely updated 4 bedroom home has been extensively renovated and expanded, adding 800 square feet including a high-end custom kitchen and breakfast room, large coffered-ceiling sunroom and office (or playroom) and roomy mudroom, tons of storage, upstairs bathrooms updated and new Marvin windows throughout the home. A blue stone patio and newly expanded backyard and landscaping add to the charm of the outdoor living space in this acre lot.
65 Greenleaf Ave, Darien, CT 06820 is a 4 bedroom, 4 bathroom, 5,350 sqft single-family home built in 1981. It last sold for $2,560,000 on Dec 5, 2008. It is currently off market. The Trulia Estimate is $4,129,200, with a rent estimate of $18,686/month.

Home Highlights

Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 65 Greenleaf Ave

Interior Features

Interior Details
BasementAdditional StorageAtticNumber of Rooms: 11Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, Recreation Room, Sun RoomStorageWet Bar
Heating & Cooling
Heating: Other, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalMicrowaveRefrigerator
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: WoodLawnPatioSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1981Year Updated: 2015
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price History for 65 Greenleaf Ave

DatePriceEventSource
12/05/2008$2,560,000Sold
Smart MLS #98392569
09/13/2008$2,595,000Listed For SaleAgent Provided
11/17/1987$725,000Sold
N/A

Market trends in Darien

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
1MoM
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Property Tax and Assessment

Year2025
Tax$29,109
Assessment$1,880,410
Home facts updated by county records

Comparable Sales for 65 Greenleaf Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
76 Deepwood Road, Darien, CT
0.18
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
3 Hickory Lane, Darien, CT
0.20
Single-Family Home
$2,875,000
07/01/26
4
4
2,920
15 Waterbury Lane, Darien, CT
0.16
Single-Family Home
$4,400,000
04/28/26
5
5
6,052
39 Deepwood Road, Darien, CT
0.37
Single-Family Home
$4,022,500
08/01/25
5
3.5
4,932
1 Top O Hill Rd, Darien, CT
0.18
Single-Family Home
$4,444,000
08/19/25
5
5
4,760
39 Briar Brae Road, Darien, CT
0.43
Single-Family Home
$2,358,000
08/01/25
4
3
3,242
26 Holly Lane, Darien, CT
0.74
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
326 Hollow Tree Ridge Road, Darien, CT
0.38
Single-Family Home
$3,650,000
08/20/25
5
4.5
6,860
19 Georgian Lane, Darien, CT
0.31
Single-Family Home
$3,250,000
03/02/26
6
5.5
6,407
261 Hollow Tree Ridge Road, Darien, CT
0.45
Single-Family Home
$4,350,000
12/15/25
5
5.5
6,135

Nearby homes

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Assigned Schools

These are the assigned schools for 65 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. "
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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 "
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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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Off Market Homes Near 65 Greenleaf Ave

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