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: 26
Lot Size: 0,78
Map
Street View

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
1912
Prairie
No
0.78
Cook
— / Not Applicable
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
Second Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Third Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Fourth Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Fifth Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Sixth Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Seventh Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Bathroom Info:
Full Bathrooms: 9
Partial Bathrooms: 3
Bathroom Amenities: Whirlpool,Separate Shower,Double Sink
Bathroom in Basement: 1
Additional Rooms Info:
Rooms: —
Basement: —
Basement Description: —

Other Specifics

3
37X37X6X154X186X46X45X45X1
Finished
Not in DB

Tax History

Year Property Taxes
2026 $55,569

Nearby Similar Homes

396 Sheridan Road, Glencoe, Illinois 60022
For Sale
$2,650,000
5 beds / 4.1 baths / 0 ft2
Single Family / Built: 1930
96

255 Harbor Street, Glencoe, Illinois 60022
For Sale
$2,849,050
5 beds / 5.2 baths / 7,989 ft2
Single Family / Built: 1996
50

621 Sheridan Road, Glencoe, Illinois 60022
For Sale
$3,250,000
6 beds / 6.1 baths / 5,903 ft2
Single Family / Built: 1998
5

231 Woodlawn Avenue, Winnetka, Illinois 60093
For Sale
$4,699,000
6 beds / 6.3 baths / 6,000 ft2
Single Family / Built: 2014
74

413 Jackson Avenue, Glencoe, Illinois 60022
For Sale
$1,949,000
4 beds / 4.1 baths / 4,578 ft2
Single Family / Built: 2007
31

154 Glenwood Avenue, Winnetka, Illinois 60093
For Sale
$950,000
3 beds / 2.0 baths / 2,333 ft2
Single Family / Built: 1919
10

Nearby Sold Comparables

419 Greenleaf Avenue, Glencoe, Illinois 60022
Sold
$2,175,000
5 beds / 7.2 baths / 0 ft2
Single Family / Built: 2002
5584

419 Greenleaf Avenue, Glencoe, Illinois 60022
Sold
$1,995,000
5 beds / 7.2 baths / 7,500 ft2
Single Family / Built: 2002
2350

231 Fairview Road, Glencoe, Illinois 60022
Sold
$3,350,000
4 beds / 6.1 baths / 0 ft2
Single Family / Built: 2007
6017

231 Fairview Road, Glencoe, Illinois 60022
Sold
$2,995,000
4 beds / 6.1 baths / 5,067 ft2
Single Family / Built: 2008
1081

206 Fairview Road, Glencoe, Illinois 60022
Sold
$1,149,000
5 beds / 3.1 baths / 4,304 ft2
Single Family / Built: 1918
2598

190 Fairview Road, Glencoe, Illinois 60022
Sold
$2,699,000
5 beds / 6.2 baths / 7,380 ft2
Single Family / Built: 2018
2636


Contact Agent

Listing Provided By

@properties Christie's International Real Estate