O'Neil Property Group

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$5,599,900
139 Days On Site

395 Greenleaf Avenue
Glencoe, IL 60022

For Sale|Single Family Residence|Active
6
Beds
9
Total Baths
6
Full Baths
3
Partial Baths
6,500
SqFt
$862
/SqFt
1912
Built
County:
Cook
Listing Courtesy of MRED as distributed by MLS Grid of @properties Christie's International Real Estate
395 Greenleaf Avenue395 Greenleaf Avenue395 Greenleaf Avenue395 Greenleaf Avenue
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What's behind the timeless classic brick facade of this East Glencoe home lies an unexpected world of glamorous high-end design with a beautiful preservation to the architectural heritage of this 1912 estate. Majestically perched above high on a rare .78 acre corner lot wrapped in a tapestry of mature trees, sculpted hedges, and lush perennial gardens, all 4 levels have been completely reimagined in a youthful vibe & rebuilt with the finest craftsmanship with no expense spared. From restored stained glass windows, marble grey & white entry with lacquered moldings and vibrant matching wallpaper to the phenomenal 3-story gym with sport court, wellness area and weight room, there are too many things to fall in love with as every room reveals a new surprise. Formal foyer leads to all the entertainment spaces with a gallery-worthy living room, to den, and then elegant dining to kitchen. This is one savvy custom Chef's kitchen with a matching butler's pantry and sleek command center, as it's right out of Elle Decor magazine. Relax and cook at the same time in the beautiful solarium breakfast room or step outside to the terraced patio for your morning coffee overlooking the lush gardens & patio. Huge family room adjacent to kitchen with limestone FP, artistic custom built-ins, and vaulted ceilings sets the mood for your nightly Love Island episode! Second and third floors with all redone high-end baths with Callista, Waterworks & Ann Sacks. Posh primary with hotel-level bath, customized closet with 2 private sections, fab sitting room with FP flanked by custom bookshelves, a true retreat. Laundry room and 2 other beds complete this floor. Third-floor retreat with decked-out hang space, 3 beds, and 2 baths. Step down to this unique lower level with direct access to heated 2 garage, a huge built-out mudroom, game room, 7th bed and bath, and of course, the gym that is fit for a professional athlete. Best yet, plan for your massage after hitting some cardio and playing basketball on your indoor court. The separate coachhouse now serves as a game room with full bath and lower level with pandora glass doors that open right onto the outdoor sports court. Gorgeous grounds with rolling greens surrounding this entire entertainment oasis. This is more than a home-it is a private luxury compound where classic elegance meets unapologetic glamour with a touch of athletic power! The pictures don't do this special home justice ...it's simply phenomenal if you are looking for a beautifully done rehab with a soul that outweighs new construction.

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Listing Snapshot
PriceΒ 
$5,599,900
Days On SiteΒ 
139 Days
BedroomsΒ 
6
Inside Area (SqFt)Β 
6,500 sqft
Total BathsΒ 
9
Full BathsΒ 
6
Partial BathsΒ 
3
Lot SizeΒ 
0.78 Acres
Year BuiltΒ 
1912
MLS NumberΒ 
12677721
StatusΒ 
Active
Property TaxΒ 
$55,569.48
HOA/Condo/Coop FeesΒ 
N/A
Sq Ft SourceΒ 
Estimated
Friends & Family
Recent Activity
4 months agoListing updated with changes from the MLS
4 months agoStatus changed to Active
5 months agoListing first seen on site
General Features
AcresΒ 
0.78
Attached GarageΒ 
Yes
Direction FacesΒ 
East
FoundationΒ 
Concrete Perimeter
GarageΒ 
Yes
Garage SpacesΒ 
3
ParkingΒ 
AsphaltGarage Door OpenerGarageAttachedDetachedDriveway
Parking SpacesΒ 
8
Property Sub TypeΒ 
Single Family Residence
SecurityΒ 
Security System
SewerΒ 
Public Sewer
StyleΒ 
Prairie
Interior Features
AppliancesΒ 
Double OvenRangeMicrowaveDishwasherFreezerWasherDryerDisposalStainless Steel Appliance(s)Wine RefrigeratorCooktopOvenRange HoodGas Cooktop
BasementΒ 
Sump PumpFinishedFull
CoolingΒ 
Central Air
ElectricΒ 
Circuit BreakersFuses200+ Amp Service
FireplaceΒ 
Yes
Fireplace FeaturesΒ 
Family RoomLiving RoomMaster BedroomWood BurningGas Starter
FireplacesΒ 
5
FlooringΒ 
Hardwood
HeatingΒ 
Natural GasForced Air
InteriorΒ 
Entrance FoyerVaulted Ceiling(s)Dry BarWet BarBuilt-in FeaturesWalk-In Closet(s)BookcasesPantry
Laundry FeaturesΒ 
Upper LevelGas Dryer Hookup
SpaΒ 
Yes
Window FeaturesΒ 
ScreensPlantation ShuttersShuttersWindow Treatments
Bedroom 2Β 
Dimensions - 15X14Level - Second
Bedroom 3Β 
Dimensions - 15X14Level - Second
Bedroom 4Β 
Dimensions - 15X13Level - Third
Bedroom 5Β 
Dimensions - 16X15Level - Third
Bedroom 6Β 
Dimensions - 18X14Level - Third
Bedroom 7Β 
Dimensions - 16X15Level - Basement
Breakfast RoomΒ 
Dimensions - 12X18Level - Main
Dining RoomΒ 
Dimensions - 21X15Level - Main
Exercise RoomΒ 
Dimensions - 28X24Level - Basement
Family RoomΒ 
Dimensions - 23X22Level - Main
FoyerΒ 
Dimensions - 26X8Level - Main
KitchenΒ 
Dimensions - 27X26Level - MainDescription - Island,Custom Cabinetry,Pantry,Updated Kitchen
LaundryΒ 
Dimensions - 7X8Level - Second
Living RoomΒ 
Dimensions - 34X17Level - Main
Master BedroomΒ 
Dimensions - 21X15Level - Second
Play RoomΒ 
Dimensions - 21X16Level - Third
Recreation RoomΒ 
Dimensions - 30X16Level - Basement
Sitting RoomΒ 
Dimensions - 15X13Level - Second
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Exterior Features
Construction DetailsΒ 
Brick
ExteriorΒ 
BalconyFire PitLighting
Lot FeaturesΒ 
Corner LotLandscaped
Other StructuresΒ 
Guest HouseSecond Garage
Patio And PorchΒ 
Patio
RoofΒ 
Asphalt
SpaΒ 
Yes
Windows/DoorsΒ 
ScreensPlantation ShuttersShuttersWindow Treatments
Community Features
Accessibility FeaturesΒ 
Therapeutic Whirlpool
Community FeaturesΒ 
CurbsSidewalks
MLS AreaΒ 
Glencoe
School DistrictΒ 
New Trier Twp H.S. Northfield/Wi
TownshipΒ 
New Trier
Schools
School District
New Trier Twp H.S. Northfield/Wi
Elementary School
West School
Middle School
Central School
High School
New Trier Twp H.S. Northfield/Wi
Listing Courtesy of MRED as distributed by MLS Grid of @properties Christie's International Real Estate



Based on information submitted to the MLS GRID as of 2026-11-09 05:37 AM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Last checked: 2026-11-09 05:37 AM UTC
MRED DMCA Copyright Information Copyright Β© 2026 Midwest Real Estate Data LLC. All rights reserved.

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