395 Greenleaf Avenue, Glencoe, Illinois 60022


$5,599,900

For Sale
Status: Active
Sqft: 6,500
Cost/Sqft: $862
Beds: 6
Baths: 9
Year Built: 1912
Property Taxes: $55,569
Days On Market: 129
Lot Size: 0,78

Description

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.

Property Specifics

Single Family
—
Prairie
1912
2006
Finished, Full
Brick
Asphalt
Prairie
No
0.78
Cook
—
— / Not Applicable
None
Lake Michigan
Public Sewer
Central Air
Natural Gas, Forced Air
No
12677721
05083010030000

Nearby Schools

NAME: DISTRICT: DISTANCE:
Grade School
West School
35 —
Middle School
Central School
35 Not in DB
High School
New Trier Twp H.s. Northfield/wi
203 Not in DB

Property History

DATE: EVENT: PRICE: SOURCE:
22 Jun, 2026 Listed for sale $5,599,900 MRED MLS

Room Specifics

All Bedroom Info:
Total Bedrooms: 7
Bedrooms Above Ground: 6
Bedrooms Below Ground: 1
Master Bedroom Info:
Dimensions: 21X15
Location: 2nd Level
Floor Type: Hardwood
Second Bedroom Info:
Dimensions: 15X14
Location: 2nd Level
Floor Type: Hardwood
Third Bedroom Info:
Dimensions: 15X14
Location: 2nd Level
Floor Type: Hardwood
Fourth Bedroom Info:
Dimensions: 15X13
Location: 3rd Level
Floor Type: Hardwood
Bathroom Info:
Full Bathrooms: 9
Partial Bathrooms: 3
Bathroom Amenities: Whirlpool, Separate Shower, Double Sink
Bathroom in Basement: 1
Dining Room Info:
Dimensions: 21X15
Location: Main Level
Floor Type: Hardwood
Kitchen Info:
Dimensions: 27X26
Location: Main Level
Floor Type: Hardwood
Features: Island, Custom Cabinetry, Pantry, Updated Kitchen
Laundry Room Info:
Dimensions: 7X8
Location: 2nd Level
Floor Type: Hardwood
Living Room Info:
Dimensions: 34X17
Location: Main Level
Floor Type: Hardwood
Family Room Info:
Dimensions: 23X22
Location: Main Level
Floor Type: Hardwood
Additional Rooms Info:
Rooms: Bedroom 5, Bedroom 6, Bedroom 7, Exercise Room, Foyer, Recreation Room, Play Room, Sitting Room, Breakfast Room
Basement: Finished, Full
First Additional Room Info:
Name: Bedroom 5
Dimensions: 16X15
Location: 3rd Level
Floor Type: Hardwood
Second Additional Room Info:
Name: Bedroom 6
Dimensions: 18X14
Location: 3rd Level
Floor Type: Hardwood
Third Additional Room Info:
Name: Bedroom 7
Dimensions: 16X15
Location: Basement
Floor Type: Hardwood
Fourth Additional Room Info:
Name: Exercise Room
Dimensions: 28X24
Location: Basement
Floor Type: Hardwood
Fifth Additional Room Info:
Name: Foyer
Dimensions: 26X8
Location: Main Level
Floor Type: Marble
Sixth Additional Room Info:
Name: Recreation Room
Dimensions: 30X16
Location: Basement
Floor Type: Other
Seventh Additional Room Info:
Name: Play Room
Dimensions: 21X16
Location: 3rd Level
Floor Type: Hardwood
Eighth Additional Room Info:
Name: Sitting Room
Dimensions: 15X13
Location: 2nd Level
Floor Type: Hardwood
Ninth Additional Room Info:
Name: Breakfast Room
Dimensions: 12X18
Location: Main Level
Floor Type: Slate

Other Specifics

3
Concrete Perimeter
Asphalt, Garage Door Opener, Garage, Garage Owned, Attached, Detached, Driveway, Owned
Upper Level, Gas Dryer Hookup
Hardwood
Patio
Guest House, Second Garage
Balcony, Hot Tub, Fire Pit, Lighting
Corner Lot, Landscaped, Mature Trees
37X37X6X154X186X46X45X45X1
Finished
Full
Vaulted Ceiling(s), Dry Bar, Wet Bar, Built-in Features, Walk-In Closet(s), Bookcases, Special Millwork, Separate Dining Room, Pantry
Double Oven, Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Washer, Dryer, Disposal, Stainless Steel Appliance(s), Wine Refrigerator, Cooktop, Oven, Range Hood, Gas Cooktop
Not in DB
Curbs, Sidewalks, Street Paved
—
Wood Burning, Gas Starter

Tax History

Year Property Taxes
2026 $55,569

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Listing Provided By

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