$5,599,900

395 Greenleaf Ave Glencoe, IL 60022

Glencoe Area

Estimated payment $35,055/month

Total Views 5,868
7 Beds
9 Baths
6,500 Sq Ft
$862 Price per Sq Ft

Highlights

  • Guest House
  • Spa
  • 0.78 Acre Lot
  • Central School Rated A
  • Second Garage
  • 4-minute walk to Shelton Park

About This Home

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.

Listing Agent

Jena Radnay

@properties Christie's International Real Estate License #475141392 Listed on: 06/22/2026

@properties Christie's International Real Estate

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $55,569

Year Built

  • Built in 1912 | Remodeled in 2006

Lot Details

  • 33,977 Sq Ft Lot
  • Lot Dimensions are 37x37x6x154x186x46x45x45x159
  • Landscaped Professionally
  • Corner Lot
  • Paved or Partially Paved Lot
  • Mature Trees

Parking

  • 3 Car Garage
  • Second Garage
  • Parking Available
  • Garage Door Opener
  • Driveway
  • Parking Included in Price

Home Design

  • Prairie Architecture
  • Brick Exterior Construction
  • Asphalt Roof
  • Concrete Perimeter Foundation

Interior Spaces

  • 6,500 Sq Ft Home
  • 3-Story Property
  • Wet Bar
  • Built-In Features
  • Bookcases
  • Dry Bar
  • Historic or Period Millwork
  • Vaulted Ceiling
  • Wood Burning Fireplace
  • Fireplace With Gas Starter
  • Plantation Shutters
  • Window Screens
  • French Doors
  • Mud Room
  • Entrance Foyer
  • Family Room with Fireplace
  • 5 Fireplaces
  • Living Room with Fireplace
  • Sitting Room
  • Breakfast Room
  • Formal Dining Room
  • Recreation Room
  • Play Room
  • Home Gym
  • Wood Flooring
  • Finished Attic

Kitchen

  • Butlers Pantry
  • Double Oven
  • Gas Cooktop
  • Range Hood
  • Microwave
  • High End Refrigerator
  • Freezer
  • Dishwasher
  • Wine Refrigerator
  • Stainless Steel Appliances
  • Disposal

Bedrooms and Bathrooms

  • 7 Bedrooms
  • 7 Potential Bedrooms
  • Fireplace in Primary Bedroom
  • Walk-In Closet
  • Dual Sinks
  • Whirlpool Bathtub
  • Separate Shower

Laundry

  • Laundry Room
  • Laundry on upper level
  • Dryer
  • Washer

Finished Basement

  • Basement Fills Entire Space Under The House
  • Sump Pump
  • Finished Basement Bathroom

Home Security

  • Home Security System
  • Carbon Monoxide Detectors
  • Fire Sprinkler System

Outdoor Features

  • Spa
  • Balcony
  • Patio
  • Fire Pit
  • Exterior Lighting

Additional Homes

  • Guest House

Schools

  • West Elementary School
  • Central Middle School
  • New Trier Twp High School Northfield/Wi

Utilities

  • Forced Air Heating and Cooling System
  • Heating System Uses Natural Gas
  • 200+ Amp Service
  • Lake Michigan Water

Community Details

  • Prairie

Home Details

Home Type

Single Family

Est. Annual Taxes

$55,569

Year Built

Built in 1912 | Remodeled in 2006

Lot Details

0.78 Acres

Parking

3

Listing Details

  • Property Type: Residential
  • Property Type: Detached Single
  • Type Detached: 3 Stories
  • Ownership: Fee Simple
  • ArchitecturalStyle: Prairie
  • HabitableResidenceYN: Yes
  • New Construction: No
  • Property Sub-Type: 3 Stories
  • Year Built: 1912
  • Age: 100+ Years
  • Built Before 1978 (Y/N): Yes
  • Disability Access and/or Equipped: No
  • General Information: School Bus Service
  • Rebuilt (Y/N): No
  • Rehab (Y/N): Yes
  • Rehab Year: 2006
  • Actual Status: Active
  • SomePhotosVirtuallyStaged: No
  • Special Features: VirtualTour
  • Property Sub Type: Detached
  • Year Renovated: 2006

Interior Features

  • 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
  • Basement: Finished, Full
  • Full Bathrooms: 6
  • Half Bathrooms: 3
  • Total Bathrooms: 9
  • Total Bedrooms: 7
  • Door Features: French Doors
  • Fireplace Features: Wood Burning, Gas Starter
  • Fireplaces: 5
  • Flooring: Hardwood
  • Interior Amenities: Vaulted Ceiling(s), Dry Bar, Wet Bar, Built-in Features, Walk-In Closet(s), Bookcases, Special Millwork, Separate Dining Room, Pantry
  • LivingArea: 6500
  • Other Equipment: Security System, Fire Sprinklers, CO Detectors, Sump Pump, Security Cameras
  • Room Type: Bedroom 5, Bedroom 6, Bedroom 7, Exercise Room, Foyer, Recreation Room, Play Room, Sitting Room, Breakfast Room
  • Window Features: Screens, Plantation Shutters, Shutters, Window Treatments
  • Estimated Total Finished Sq Ft: 0
  • Bathroom Amenities: Whirlpool,Separate Shower,Double Sink
  • Basement Bathrooms: Yes
  • Below Grade Bedrooms: 1
  • Dining Room: Separate
  • Fireplace Location: Family Room,Living Room,Master Bedroom,Other
  • Total Sq Ft: 0
  • Attic: Finished
  • Flooring: Hardwood

Exterior Features

  • Construction Materials: Brick
  • ExteriorFeatures: Balcony, Hot Tub, Fire Pit, Lighting
  • Foundation Details: Concrete Perimeter
  • Lot Features: Corner Lot, Landscaped, Mature Trees
  • OtherStructures: Guest House, Second Garage
  • Patio And Porch Features: Patio
  • Roof: Asphalt
  • Waterfront: No

Garage/Parking

  • Garage Spaces: 3
  • Parking Features: Asphalt, Garage Door Opener, Garage, Yes, Garage Owned, Attached, Detached, Driveway, Owned
  • ParkingTotal: 8

Utilities

  • Sewer: Public Sewer
  • Cooling: Central Air
  • Electric: Circuit Breakers, Fuses, 200+ Amp Service
  • Heating: Natural Gas, Forced Air
  • Laundry Features: Upper Level, Gas Dryer Hookup
  • Water Source: Lake Michigan

Condo/Co-op/Association

  • Association Fee Frequency: Not Applicable
  • Community Features: Curbs, Sidewalks, Street Paved
  • Master Association Fee Frequency: Not Required

Fee Information

  • Association Fee Includes: None

Schools

  • Elementary School: West School
  • High School: New Trier Twp H.S. Northfield/Wi
  • Middle/Junior School: Central School

Lot Info

  • Lot Size Acres: 0.78
  • Lot Dimensions: 37X37X6X154X186X46X45X45X159
  • Rural (Y/N): N
  • Lot Size: .50-.99 Acre
  • Special Assessments: N

Rental Info

  • Board Number: 8
  • Is Parking Included in Price: Yes

Tax Info

  • Tax Annual Amount: 55569.48
  • Tax Year: 2024
  • Tax Exemptions: None

Map

Range of Values:

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Value Increase
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $52,470 $250,000 $68,758 $181,242
2024 $52,470 $217,521 $75,634 $141,887
2023 $48,963 $217,521 $75,634 $141,887
2022 $48,963 $217,521 $75,634 $141,887
2021 $47,636 $169,483 $72,195 $97,288
2020 $46,311 $169,483 $72,195 $97,288
2019 $44,221 $182,240 $72,195 $110,045
2018 $39,559 $159,052 $61,882 $97,170
2017 $38,448 $159,052 $61,882 $97,170
2016 $36,302 $159,052 $61,882 $97,170
2015 $38,606 $150,024 $52,427 $97,597
2014 $37,666 $150,024 $52,427 $97,597
2013 $35,914 $150,024 $52,427 $97,597
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft
06/22/2026 06/22/26 For Sale $5,599,900 -- $862 / Sq Ft
Source: Midwest Real Estate Data (MRED)

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Type Sale Price Title Company
Warranty Deed -- --
Warranty Deed $2,881,500 Cti
Corporate Deed $1,675,000 Cti
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Loan Amount Loan Type
Previous Owner $2,750,000 Construction
Source: Public Records

Source: Midwest Real Estate Data (MRED)

MLS Number: 12677721

Midwest Real Estate Data (MRED)

APN: 05-08-301-003-0000

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