$5,599,900

395 Greenleaf Avenue, Glencoe, IL 60022

Active
6 beds (7 possible) 6.5 baths 6,500 sqft (estimated) Built 1912 Residential MLS #MRD12677721 33 days on market
Listing courtesy of @properties Christie's International Real Estate · 847-881-0200 · MLS #MRD12677721 · Status: Active
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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Property details

Interior

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
Interior features
Vaulted Ceiling(s), Dry Bar, Wet Bar, Built-in Features, Walk-In Closet(s), Bookcases, Special Millwork, Separate Dining Room, Pantry
Flooring
Hardwood
Fireplaces
5
Fireplace details
Wood Burning, Gas Starter
Basement
Finished, Full
Laundry
Upper Level, Gas Dryer Hookup
Additional rooms
Bedroom 5, Bedroom 6, Bedroom 7, Exercise Room, Foyer, Recreation Room, Play Room, Sitting Room, Breakfast Room
Total rooms
16

Building & exterior

Style
Prairie
Age
100+ Years
Exterior
Brick
Exterior features
Balcony, Hot Tub, Fire Pit, Lighting
Roof
Asphalt
Foundation
Concrete Perimeter
Windows
Screens, Plantation Shutters, Shutters, Window Treatments
Doors
French Doors
Patio & porch
Patio
Other structures
Guest House, Second Garage
Exposure
North,South,East,West

Parking

Garage spaces
3
Total spaces
8
Parking details
Asphalt, Garage Door Opener, Garage, Yes, Garage Owned, Attached, Detached, Driveway, Owned

Lot & location

Lot dimensions
37X37X6X154X186X46X45X45X159
Lot description
Corner Lot, Landscaped, Mature Trees
Township
New Trier
County
Cook

Utilities

Heating
Natural Gas, Forced Air
Cooling
Central Air
Water
Lake Michigan
Sewer
Public Sewer
Electricity
Circuit Breakers, Fuses, 200+ Amp Service
Equipment
Security System, Fire Sprinklers, CO Detectors, Sump Pump, Security Cameras

HOA & community

Assessment includes
None
Community features
Curbs, Sidewalks, Street Paved

Schools

Elementary
West School (35)
Junior high
Central School (35)
High school
New Trier Twp H.S. Northfield/Wi (203)

Taxes & terms

Annual taxes
$55,569 (2024)
Parcel number (PIN)
05083010030000
PIN
05083010030000
Ownership
Fee Simple
Possession
Closing
Special conditions
None
Listed
6/22/2026

Rooms

RoomSizeLevelFlooring
Bedroom 516X15ThirdHardwood
Bedroom 618X14ThirdHardwood
Bedroom 716X15BasementHardwood
Exercise Room28X24BasementHardwood
Foyer26X8MainMarble
Recreation Room30X16BasementOther
Play Room21X16ThirdHardwood
Sitting Room15X13SecondHardwood
Breakfast Room12X18MainSlate
Bedroom 215X14SecondHardwood
Bedroom 315X14SecondHardwood
Bedroom 415X13ThirdHardwood
Dining Room21X15MainHardwood
Family Room23X22MainHardwood
Kitchen27X26MainHardwood
Laundry7X8SecondHardwood
Living Room34X17MainHardwood
Master Bedroom21X15SecondHardwood

What would this home cost per month?

Using this listing's actual tax bill (2024) — adjust anything.

Rates move daily — edit to today's quote. Under 20% down adds PMI automatically.

Estimated monthly payment
$0
Principal & interest
Property taxes
Insurance
PMI (under 20% down)
HOA / assessments

Estimates only — not a loan offer or quote; your rate, insurance and PMI depend on your credit and lender. Run other scenarios on the full mortgage calculator, or ask us to connect you with lenders our clients actually close with.

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