395 Greenleaf Ave
Glencoe, IL 60022
For more information on this listing, contact us at: (773) 998-2401
Active
$5,599,900
395 Greenleaf Ave Glencoe, IL 60022
Detached Single
Property Type
6
Beds
6 Full 3 Half
Baths
6,500
Sq. Ft.
1912
Year Built
Cook
County
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.
MLS #
12677721
Monthly HOA
N/A
On Site
89 Days
Last Updated
7/24/2026
Contact Agent
Property Rocks
(773) 998-2401Property Details
Community Information
School Information
School District
35
High School
New Trier Twp H.S. Northfield/Wi
Middle School
Central School
Elementary School
West School
Architecture
Bedrooms
6
Bathrooms
6 Full / 3 Half
Year Built
1912
Style
Prairie
Construction Materials
Brick
Age Range
100+ Years
Type Detached
3 Stories
Roof
Asphalt
Foundation
Concrete Perimeter
Basement Type
Finished, Full
Parking Features
Asphalt, Garage Door Opener, Garage, Yes, Garage Owned, Attached, Detached, Driveway, Owned
Features / Amenities
Interior Features
Vaulted Ceiling(s), Dry Bar, Wet Bar, Built-in Features, Walk-In Closet(s), Bookcases, Special Millwork, Separate Dining Room, Pantry
Appliances
Double Oven, Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Washer, Dryer, Disposal, Stainless Steel Appliance(s), Wine Refrigerator, Cooktop, Oven, Range Hood, Gas Cooktop
Equipment
Security System, Fire Sprinklers, CO Detectors, Sump Pump, Security Cameras
Fireplace Features
Wood Burning, Gas Starter
Fireplaces Total
5
Flooring
Hardwood
Laundry
Upper Level, Gas Dryer Hookup
Rooms
Bedroom 5, Bedroom 6, Bedroom 7, Exercise Room, Foyer, Recreation Room, Play Room, Sitting Room, Breakfast Room
Exterior Features
Balcony, Hot Tub, Fire Pit, Lighting
Patio And Porch
Patio
Other Structures
Guest House, Second Garage
Window
Screens, Plantation Shutters, Shutters, Window Treatments
Parking Total
8
Garage Spaces
3
Air Conditioning
Central Air
Heat Source / Type
Natural Gas, Forced Air
Fireplace(s)
Family Room, Living Room, Master Bedroom
Total Rooms
16
Property Features
Lot Size
0.78 Acres
Lot Dimensions
.50-.99 Acre
Lot Features
Corner Lot, Landscaped, Mature Trees
Sewer
Public Sewer
Water
Lake Michigan
Electric
Circuit Breakers, Fuses, 200+ Amp Service
Transportation
School Bus Service
Open House Count
1
Open House Update
2026-07-24T20:07:41
Directions
Sheridan South to Greenleaf to 395
Tax and Financial Info
Tax Year
2024
Tax Annual Amount
$55,569.48
Ownership
Fee Simple
Rooms
| Level | |
| Bedroom 7 | Basement |
| Exercise Room | Basement |
| Recreation Room | Basement |
| Dining Room | Main |
| Family Room | Main |
| Kitchen | Main |
| Living Room | Main |
| Foyer | Main |
| Breakfast Room | Main |
| N/A | |
| Bedroom 2 | Second |
| Bedroom 3 | Second |
| Laundry | Second |
| Master Bedroom | Second |
| Sitting Room | Second |
| Bedroom 5 | Third |
| Bedroom 4 | Third |
| Bedroom 6 | Third |
| Play Room | Third |
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Listing provided courtesy of @Properties Christie's International Real Estate.Listings courtesy of MRED MLS as distributed by MLS GRID
Based on information submitted to the MLS GRID as of September 18, 2026 7:00 AM CST. 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.
Properties displayed may be listed or sold by various participants in the MLS