395 Greenleaf Avenue, Glencoe, IL

$5,599,900

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6

Beds

Baths

6,500

Square feet

0.78

Acres

About 395 Greenleaf Avenue

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.

Features of 395 Greenleaf Avenue

MLS® # 12677721
Price $5,599,900
Bedrooms 6
Bathrooms 7.50
Full Baths 6
Half Baths 3
Square Footage 6,500
Acres 0.78
Year Built 1912
Type Residential
Sub-Type Detached Single
Style Prairie
Status Active

Community Information

Address 395 Greenleaf Avenue
Area Glencoe
City Glencoe
County Cook
State IL
Zip Code 60022

Amenities

Parking Spaces 8
Parking Asphalt, Garage Door Opener, Garage, Yes, Garage Owned, Attached, Detached, Driveway, Owned
# of Garages 3
Is Waterfront No
Has Pool No

Interior

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
Heating Natural Gas, Forced Air
Cooling Central Air
Fireplace Yes
# of Fireplaces 5
Fireplaces Wood Burning, Gas Starter
Stories 3 Stories
Has Basement Yes
Basement Finished, Full

Exterior

Exterior Brick
Exterior Features Balcony, Hot Tub, Fire Pit, Lighting
Lot Description Corner Lot, Landscaped, Mature Trees
Roof Asphalt
Foundation Concrete Perimeter

School Information

District 203
Elementary West School
Middle Central School
High New Trier Twp H.S. Northfield/Wi

Additional Information

Days on Market 33
Foreclosure No
Short Sale No
RE / Bank Owned No
HOA Fees Freq. Not Applicable

Listing Details

Office@properties Christie's International Real Estate

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Listing information last updated on September 20th, 2026 at 7:52pm CDT.