86 Greenleaf Avenue, Darien, CT 06820
OFF MARKET

86 Greenleaf Avenue
Darien, CT 06820

  • 6 Beds
  • 5.5 Baths
  • 5,691 sqft (on 2.03 acres)

$4,237,700

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $27,182/mo*
Refinance Your Home

$4,237,700

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $27,182/mo*
Refinance Your Home
6 Beds
5.5 Baths
5,691 sqft
(on 2.03 acres)

Local Information

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

Description

Welcomed by the new year, chance brings an opportunity to capture this elegant estate that is highly approachable by today’s modern living, on one of the most coveted streets in Darien. Situated on a private 2 acre lot, this gracious home welcomes you the minute you enter through the grand and stately front porch. Enjoy long summer days by your pool and pergola that are surrounded by landscaping details such as a stately Japanese Maple and evergreens. Abundant light pours in and fills the generous main entry rooms with 9’ ceilings. There is plenty of space for all with 6 bedrooms, 2 bonus rooms, primary with en suite and upper laundry. A remodeled classic white kitchen and fully updated bathrooms make this a turn key residence and ready for you to simply move right in. Additional amenities include a greenhouse & gym, sauna, wine cellar and much more. Come enjoy a taste of New England and start making your own memories for generations to come!
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. This description is from July 10, 2024

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Patio, Pool
A/C
Heating & Cooling
HOA
$33/Monthly
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 86 Greenleaf Avenue

Interior Features

Interior Details
Basement: Full,Unfinished,Concrete,Storage Space,Sump PumpNumber of Rooms: 13Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Other
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5691 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Oven, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Dryer, Water HeaterDishwasherDisposalDryerLaundry: Lower Level,Upper LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,Radiator,Zoned,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Patio, PorchFencing: PartialOther Structures: Gazebo, Shed(s), GreenhouseExterior: Awning(s), Rain Gutters, Lighting, Underground SprinklerFoundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Attached,Garage Door Opener,Private
Pool
Pool: In Ground, Heated, Fenced, ConcretePool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 5286 Square FeetFinished Area (below surface): 405 Square Feet

Property Information

Year Built
Year Built: 1926
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Vinyl Siding, Aluminum SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 105639

Price & Status

Price
List Price: $2,995,000
Status Change & Dates
Off Market Date: Fri Feb 16 2024Possession Timing: Negotiable

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Darien
School Information
Elementary School: HolmesJr High / Middle School: MiddlesexHigh School: Darien

Building

Building Area
Building Area: 5691 Square Feet

Community

Community Features: Near Public Transport, Golf, Health Club, Library, Paddle Tennis, Park, Playground, Tennis Court(s)
Other
Playground

HOA

Has an HOAHOA Fee: $400/Annually

Lot Information

Lot Area: 2.03 Acres

Miscellaneous

BasementMls Number: 170615649Attic: Walk-up, Floored, StorageAbove Grade Unfinished Area: 5286

Additional Information

Near Public TransportGolfHealth ClubLibraryPaddle TennisParkPlaygroundTennis Court(s)
Last check for updates: about 3 hours ago
Listed by Ashley Bartolotta, (646) 271-8430
Brown Harris Stevens, (203) 655-1418
Bought with: Casey Lange, (203) 249-0900, Compass Connecticut, LLC, (203) 423-3100
Source: Smart MLS, MLS#170615649

Price History for 86 Greenleaf Avenue

DatePriceEventSource
04/25/2024$2,995,000Sold
Smart MLS #170615649
02/16/2024$2,995,000PendingSmart MLS #170615649
02/09/2024$2,995,000PriceChange
Smart MLS #170615649
01/01/2024$3,150,000Listed For SaleHalstead / Brown Harris Stevens #170615649
05/06/2015$2,200,000Sold
N/A
07/30/2014$2,200,000Sold
Smart MLS #99056372
05/07/2014$2,199,000Listed For SaleAgent Provided
10/14/2013$2,575,000ListingRemovedAgent Provided
09/03/2013$2,575,000PriceChange
Agent Provided
06/11/2013$2,745,000PriceChange
Agent Provided
04/25/2013$2,895,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$32,421
Assessment$2,094,400
Home facts updated by county records

Comparable Sales for 86 Greenleaf Avenue

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
19 Georgian Lane, Darien, CT
0.21
Single-Family Home
$3,250,000
03/02/26
6
5.5
6,407
76 Deepwood Road, Darien, CT
0.14
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
15 Waterbury Lane, Darien, CT
0.29
Single-Family Home
$4,400,000
04/28/26
5
5
6,052
326 Hollow Tree Ridge Road, Darien, CT
0.49
Single-Family Home
$3,650,000
08/20/25
5
4.5
6,860
4 Echo Drive, Darien, CT
0.32
Single-Family Home
$3,500,000
08/06/25
5
5
5,348
261 Hollow Tree Ridge Road, Darien, CT
0.49
Single-Family Home
$4,350,000
12/15/25
5
5.5
6,135
7 Lantern Lane, Darien, CT
0.40
Single-Family Home
$2,355,000
06/12/25
4
3.5
3,742
39 Deepwood Road, Darien, CT
0.42
Single-Family Home
$4,022,500
08/01/25
5
3.5
4,932

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Assigned Schools

These are the assigned schools for 86 Greenleaf Avenue.
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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
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  • 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
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  • 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
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  • dwenger
    "Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
    0
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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Homes for rent near 86 Greenleaf Avenue

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86 Greenleaf Avenue, Darien, CT 06820 is a 6 bedroom, 6 bathroom, 5,691 sqft single-family home built in 1926. This property is not currently available for sale. 86 Greenleaf Avenue was last sold on Apr 25, 2024 for $2,995,000 (0% higher than the asking price of $2,995,000). The current Trulia Estimate for 86 Greenleaf Avenue is $4,237,700.