Date
Details
Price
Change
Source
6/22/2026
Listed
$5,599,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
No photo available
$5,599,900 Just Listed
Property 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.
Full Property Details
Full Property Details for 395 Greenleaf Ave
General
- Price: $5,599,900
- Taxes: $55,569 (2024)
- Status: Active
- Type: Single Family
- Source: MRED
- MLS ID: 12677721
- Updated: 6/22/2026
- Added to Site: 5 day(s) ago
Rental Information
- Complex Features: Curbs, Sidewalks, Street Paved
Interior
- Basement: Finished, F
- Interior Features: Vaulted Ceiling(s), Dry Bar, Wet Bar, Built-in Features, Walk-In Closet(s), Bookcases, Special Millwork, Separate Dining Room, Pantry
- Fireplace: Yes
- Number of Fireplaces: 5
- Fireplace(s): Family Room, Living Room, Master Bedroom, Other, 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
Rooms
Bathrooms
- Total Bathrooms: 9
- Full Bathrooms: 6
- Half Bathrooms: 3
- Basement Baths: Yes
- Bathroom Features: Whirlpool, Separate Shower, Double Sink
Bedrooms
- Total Bedrooms: 7
- Bedrooms(Blw Grade): 1
Additional Information
- Equipment: Security System, Fire Sprinklers, Carbon Monoxide Detectors, Sump Pump, Security Cameras
- Other Features: School Bus Service
Exterior
- Exterior Features: Balcony, Hot Tub, Fire Pit, Lighting
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Total Spaces: 8
- Parking Features: Asphalt, Garage Door Opener, Garage, Yes, Garage Owned, Attached, Detached, Driveway, Owned
Location
- Area: Glencoe
- County: Cook
- Township: New Trier
- Driving Directions: Sheridan South to Greenleaf to 395
School Information
- School District: 35
- Elem School District: 35
- Midd School District: 35
- High School District: 203
- Elementary School: West School
- Middle School: Central School
- High School: New Trier Twp H.S. Northfield/Wi
- Private School: New Trier Twp H.S. Northfield/Wi
Community
- Assoc. Fees Include: None
Heating & Cooling
- Cooling Type: Central Air Conditioning
- Heating Type: Natural Gas, Forced Air
Utilities
- Sewer: Public Sewer
- Water: Lake Michigan
Structural Information
- Architectural Info: Prairie
- Architectural Style: Prairie
- Model: Prairie
- Construction: Brick
- Exterior Const.: Brick
- Basement: Yes
- Basement Desc.: Finished, Full
- Foundation: Concrete Perimeter
- Roof: Asphalt
- Windows: Screens, Plantation Shutters, Shutters, Window Treatments
- Doors: French Doors
- Sub-Flooring: Hardwood
- Square Feet: 6,500
- Sq. Ft. Source: Estimated
- Year Built: 1912
- Built Before 1978: Yes
- Remodeled/Updated: 2006
Manufactured Home
- Model: Prairie
Additional Structures
- Other Structures: Guest House, Second Garage
Lot Features
- Lot Size (Acres): 0.78
- Lot Size Range: .50 to .99 Acre
- Lot Dimensions: 37 x 37 x 6 x 154 x 186 x 46 x 45 x 45 x 159
- Lot Features: Corner Lot, Landscaped, Mature Trees
Financial Considerations
- Parking Included: Yes
- Assessment Year: 1912
- Tax Amount: $55,569.48
- Tax Year: 2024
- Pays Sewer: Public Sewer
Disclosures and Reports
- Ownership: Fee Simple
- Property ID: 5083010030000
Listed by @properties Christie's International Real Estate
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— 395 Greenleaf Ave —
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Schools
Schools serving 395 Greenleaf Ave
School Districts:Glencoe School District 35, New Trier Township High School District 203
| Name | Grades | Distance |
|---|---|---|
South Elementary School, Glencoe, IL 266 Linden Avenue, Glencoe, IL 60022 | PK-2 | 0.4 mi |
Central School, Glencoe, IL 620 Greenwood Avenue, Glencoe, IL 60022 | 5-8 | 0.6 mi |
West School 1010 Forestway Drive, Glencoe, IL 60022 | 3-4 | 1.5 mi |
New Trier Township H S Northfield 7 North Happ Road, Northfield, IL 60093 | 9- | 2.8 mi |
New Trier Township H S Winnetka 385 Winnetka Avenue, Winnetka, IL 60093 | 10-12 | 2.9 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 395 Greenleaf Ave
Tax History
Tax History for 395 Greenleaf Ave
Year
Property Taxes
Change
Tax Assessment
Change
2023
$52,470
—
$250,000
15%
2023
$52,470
7%
$217,519
—
2022
$48,963
3%
$217,519
28%
2021
$47,636
3%
$169,483
—
2020
$46,311
5%
$169,483
-7%
2019
$44,221
12%
$182,240
15%
2018
$39,559
3%
$159,052
—
2017
$38,448
6%
$159,052
—
2016
$36,302
-6%
$159,052
6%
2015
$38,606
2%
$150,024
—
2014
$37,666
5%
$150,024
—
2013
$35,914
-25%
$150,024
-29%
2012
$48,083
—
$212,606
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 395 Greenleaf Ave
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- Single Family
- Active
- Updated 11 days ago
- 6Beds
- 9Total Baths
- 7,480Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 4Total Baths
- 2,000Sq. Ft.
Listed by The Sheu Team (847) 544-8207
![[Address not provided], Highland Park, IL 60035 - Photo 1](https://m1.cbhomes.com/p/196/12663892/1be07D22711e478/s23cc.webp)
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- Single Family
- Active
- Updated 4 days ago
- 3Beds
- 3Total Baths
- 1,648Sq. Ft.
- Condo / Townhouse
- Active
- Updated 2 days ago
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- Active
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- Single Family
- Closed
- Updated 12 days ago
- 6Beds
- 6Total Baths
- 6,020Sq. Ft.
395 Greenleaf Avenue, Glencoe, IL 60022 (MLS# 12677721) is a Single Family property with 7 bedrooms, 6 full bathrooms and 3 partial bathrooms. 395 Greenleaf Avenue is currently listed for $5,599,900 and was received on June 22, 2026. Want to learn more about 395 Greenleaf Avenue? Do you have questions about finding other Single Family real estate for sale in Glencoe? You can browse all Glencoe real estate or contact a Coldwell Banker agent to request more information.