395 Greenleaf Ave Glencoe, IL 60022
395 Greenleaf Ave Glencoe, IL 60022 | MLS 12677721 Photo 1
395 Greenleaf Ave Glencoe, IL 60022 | MLS 12677721 Photo 2
395 Greenleaf Ave Glencoe, IL 60022 | MLS 12677721 Photo 3
395 Greenleaf Ave Glencoe, IL 60022 | MLS 12677721 Photo 4
395 Greenleaf Ave Glencoe, IL 60022 | MLS 12677721 Photo 5
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
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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.
MLS # 12677721
Monthly HOA N/A
On Site 89 Days
Last Updated 7/24/2026

Contact Agent

Property Rocks

Property Rocks

(773) 998-2401

Property Details

Community Information

Address 395 Greenleaf Ave, Glencoe, IL 60022
Area Glencoe
County Cook
City Glencoe
Township New Trier
Zip Code 60022

School Information

School District 35
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 7Basement
Exercise RoomBasement
Recreation RoomBasement
Dining RoomMain
Family RoomMain
KitchenMain
Living RoomMain
FoyerMain
Breakfast RoomMain
N/A
Bedroom 2Second
Bedroom 3Second
LaundrySecond
Master BedroomSecond
Sitting RoomSecond
Bedroom 5Third
Bedroom 4Third
Bedroom 6Third
Play RoomThird

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395 Greenleaf Ave Glencoe, IL 60022 | MLS 12677721
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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

(773) 998-2401
395 Greenleaf Ave Glencoe, IL 60022
  • $5,599,900
  • 6 beds
  • 6 full  3 half baths
  • 6,500 Sq. Ft.