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395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
395 Greenleaf Avenue
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Listed by Jena Radnay with @properties Christie's International Real Estate 312-925-9899
$5,599,900

395 Greenleaf Avenue

7 Beds 9 Baths 6,500 Sq.Ft. 0.78 Acres

Open House

6/23/2026 10:30AM - 1:00PM CDT

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.

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Location

395 Greenleaf Avenue, Glencoe, IL 60022

Status

For Sale
Jena Radnay

Jena Radnay

Property Amenities

Interior
Laundry room Upper Level, Gas Dryer Hookup
Fireplace Wood Burning, Gas Starter
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
Flooring Hardwood
Total Bedrooms: 7
Half Bathrooms: 3
Full Bathrooms: 6
Other Interior Features Vaulted Ceiling(s), Dry Bar, Wet Bar, Built-in Features, Walk-In Closet(s), Bookcases, Special Millwork, Separate Dining Room, Pantry
Area & Lot
Open house

6/23/2026 10:30AM - 1:00PM CDT

Lot Area 0.78 Acres
Living area 6,500 Sq.Ft.
MLS® ID 12677721
Year Built 1912
School District 203
High School New Trier Twp H.S. Northfield/Wi
Middle School Central School
Elementary School West School
Architecture Styles Prairie
Type Residential
Status For Sale
Exterior
Air conditioning Central Air
Heat type Natural Gas, Forced Air
Water Source Lake Michigan
Garage Space 3.0
Sewer Public Sewer
Other Exterior Features Balcony, Hot Tub, Fire Pit, Lighting
Parking Asphalt, Garage Door Opener, Garage, Yes, Garage Owned, Attached, Detached, Driveway, Owned
Lot Features Corner Lot, Landscaped, Mature Trees
Roof Asphalt
Finance
Sales Price $5,599,900
Real Estate Tax $55,569 yearly

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Glencoe

The origins of the name “Glencoe” are not certain but may be related to the town of Glencoe in Scotland.

Work With Jena

Jena Radnay, and the focus of her real estate business, is all about people. Radnay’s love for real estate, houses, marketing, and people have allowed her business to grow organically, albeit explosively, in large part from referrals from her extensive network of contacts and connections.

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