395 Greenleaf Ave
Glencoe, IL 60022
7 Beds
7.5 Baths
6,500 sqft (on 0.78 acres)
7 Beds
7.5 Baths
6,500 sqft
(on 0.78 acres)
Local Information
- Map ViewExplore the area around 395 Greenleaf Ave.
- Schools1 Preschool School3 Elementary Schools2 Middle Schools2 High Schools
- Shop & Eat
-- mins to
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.
Open House
Tuesday, June 23
10:30 AM to 1:00 PM
Home Highlights
Parking
3 Car Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
$862
Listed
1 day ago
Home Details for 395 Greenleaf Ave
|
|---|
MLS Status: New |
|
|---|
Interior Details Basement: Finished,FullNumber of Rooms: 16Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Bedroom 6, Bedroom 7, Breakfast Room, Dining Room, Exercise Room, Family Room, Foyer, Kitchen, Laundry, Living Room, Play Room, Recreation Room, Sitting RoomWet Bar |
Beds & Baths Number of Bedrooms: 7Number of Bathrooms: 9Number of Bathrooms (full): 6Number of Bathrooms (half): 3 |
Dimensions and Layout Living Area: 6500 Square Feet |
Appliances & Utilities Appliances: Double Oven, Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Washer, Dryer, Disposal, Stainless Steel Appliance(s), Wine Refrigerator, Cooktop, Oven, Range Hood, Gas CooktopDishwasherDisposalDryerLaundry: Upper Level,Gas Dryer HookupMicrowaveWasher |
Heating & Cooling Heating: Natural Gas,Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas |
Fireplace & Spa Number of Fireplaces: 5Fireplace: Wood Burning, Gas Starter, Family Room, Living Room, Master Bedroom, OtherSpa: Outdoor Hot TubHas a FireplaceHas a Spa |
Gas & Electric Electric: Circuit Breakers, Fuses, 200+ Amp Service |
Windows, Doors, Floors & Walls Window: Screens, Plantation Shutters, Shutters, Window TreatmentsDoor: French DoorsFlooring: Hardwood |
Levels, Entrance, & Accessibility Stories: 3Accessibility: No Disability AccessFloors: Hardwood |
View No View |
Security Security: Security System, Fire Sprinkler System, Carbon Monoxide Detector(s), Closed Circuit Camera(s) |
|
|---|
Exterior Home Features Roof: AsphaltPatio / Porch: PatioOther Structures: Guest House, Second GarageExterior: Balcony, Fire Pit, LightingFoundation: Concrete Perimeter |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3Has a GarageHas an Attached GarageHas Open ParkingParking Spaces: 8Parking: Asphalt,Garage Door Opener,Garage,Yes,Garage Owned,Attached,Detached,Driveway,Owned |
Frontage Not on Waterfront |
Water & Sewer Sewer: Public Sewer |
|
|---|
Days on Market: 1 |
|
|---|
Year Built Year Built: 1912Year Renovated: 2006 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Prairie |
Building Construction Materials: BrickNot a New ConstructionIs Habitable Residence |
Property Information Parcel Number: 05083010030000Model Home Type: Prairie |
|
|---|
Price List Price: $5,599,900Price Per Sqft: $862 |
Status Change & Dates Possession Timing: Close Of Escrow |
|
|---|
|
|---|
Direction & Address City: Glencoe |
School Information Elementary School: West SchoolElementary School District: 35Jr High / Middle School: Central SchoolJr High / Middle School District: 35High School: New Trier Twp H.S. Northfield/WiHigh School District: 203 |
|
|---|
Listing Agent Listing ID: 12677721 |
|
|---|
Building Details Builder Model: Prairie |
|
|---|
Community Features: Curbs, Sidewalks, Street Paved |
|
|---|
HOA Fee Includes: None |
|
|---|
Lot Area: 0.78 acres |
|
|---|
Special Conditions: None |
|
|---|
Business Information Ownership: Fee Simple |
|
|---|
BasementMls Number: 12677721Attic: Finished |
|
|---|
CurbsSidewalksStreet PavedSource Internet Consumer CommentSource Internet Entire Listing DisplayMRD IDX Comments Reviews: YesMRD Listing On IDX Display: YesMRD AVM On IDX Display: YesMRD Address On VOW Display: YesSource Internet Automated Valuation DisplayMRD Price History On IDX Display: YesMRD Market Time On IDX Display: YesMRD REMARKSINTERNET: YesSource Internet Address DisplayMRD Remarks On VOW Display: Yes |
Last check for updates: about 7 hours ago
Listing courtesy of: Jena Radnay, (312) 925-9899
@properties Christie's International Real Estate
Source: MRED as distributed by MLS GRID, MLS#12677721
Also Listed on MRED as distributed by MLS GRID.
Market trends in Glencoe
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
29
6MoM
Price History for 395 Greenleaf Ave
| Date | Price | Event | Source |
|---|---|---|---|
| 06/22/2026 | $5,599,900 | Listed For Sale | MRED as distributed by MLS GRID #12677721 |
| 06/10/2026 | $5,900,000 | ListingRemoved | MRED as distributed by MLS GRID #12481858 |
| 04/09/2026 | $5,900,000 | Listed For Sale | MRED as distributed by MLS GRID #12481858 |
| 01/09/2006 | $2,881,500 | Sold | N/A |
| 12/17/2003 | $1,675,000 | Sold | N/A |
Similar Homes You May Like
2.31 ACRES@properties Christie's International Real Estate, Active
1.61 ACRESJameson Sotheby's International Realty, Price Change
2.02 ACRESBerkshire Hathaway HomeServices Chicago, Active
0.78 ACRES@properties Christie's International Real Estate, Active
2.4 ACRESJameson Sotheby's Intl Realty, Active
0.51 ACRES@properties Christie's International Real Estate, Active
1.69 ACRES@properties Christie's International Real Estate, Active
0.5 ACRES@properties Christie's International Real Estate, Active
0.38 ACRESColdwell Banker Realty, Active
3.18 ACRES@properties Christie's International Real Estate, Price Change
0.4 ACRES@properties Christie's International Real Estate, Active
Jameson Sotheby's Intl Realty, Active
1.09 ACRES@properties Christie's International Real Estate, Active
@properties Christie's International Real Estate, Active
OPEN SUN, 12-2PM1.05 ACRES@properties Christie's International Real Estate, Active
Jameson Sotheby's Intl Realty, Active
NEW CONSTRUCTION0.5 ACRES@properties Christie's International Real Estate, Active
NEW - 14 HRS AGO2.02 ACRES@properties Christie's International Real Estate, New
0.52 ACRESColdwell Banker Realty, Active
1.85 ACRESJason Mitchell Real Estate IL, Active
Jameson Sotheby's Intl Realty, Active
NEW CONSTRUCTION0.34 ACRES@properties Christie's International Real Estate, Active
@properties Christie's International Real Estate, Active
1.14 ACRES@properties Christie's International Real Estate, Active
@properties Christie's International Real Estate, Active
Jameson Sotheby's Intl Realty, Active
Jameson Sotheby's Intl Realty, Active
0.55 ACRES@properties Christie's International Real Estate, Active
9.36 ACRESColdwell Banker Realty, Active
Keller Williams ONEChicago, Active
0.4 ACRES@properties Christie's International Real Estate, Active
OPEN SAT, 1-3PM0.25 ACRESJameson Sotheby's Intl Realty, Active
0.4 ACRESWinnetka Realty, Inc., Active
9.62 ACRESJameson Sotheby's International Realty, Active
See more homes for sale inGlencoe
New Listings near 395 Greenleaf Ave
1.25 ACRES@properties Christie's International Real Estate, Active
2.2 ACRES@properties Christie's International Real Estate, Active
@properties Christie's International Real Estate, New- 0.52 ACRESColdwell Banker Realty, Active
- 0.5 ACRES@properties Christie's International Real Estate, Active
0.76 ACRES@properties Christie's International Real Estate, Active- 0.51 ACRES@properties Christie's International Real Estate, Active
- 1.14 ACRES@properties Christie's International Real Estate, Active
- 0.4 ACRES@properties Christie's International Real Estate, Active
1.2 ACRES@properties Christie's International Real Estate, Active
0.72 ACRESRE/MAX Premier Luxury Collection, Price Change
0.95 ACRES@properties Christie's International Real Estate, Active- See more homes for sale inGlencoe
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | |
| Assessment | $2,175,210 |
Home facts updated by county records
Comparable Sales for 395 Greenleaf Ave
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.05 | Single-Family Home | $3,450,000 | 06/25/25 | 6 | 7 | 6,403 | |
0.19 | Single-Family Home | $3,500,000 | 08/11/25 | 6 | 7 | 8,000 | |
0.18 | Single-Family Home | $3,700,000 | 10/10/25 | 6 | 6.5 | 8,445 | |
0.23 | Single-Family Home | $3,750,000 | 11/21/25 | 5 | 5.5 | 5,764 | |
0.34 | Single-Family Home | $2,650,000 | 10/06/25 | 5 | 6.5 | 5,783 | |
0.15 | Single-Family Home | $3,140,000 | 03/05/26 | 5 | 5 | 3,916 | |
0.33 | Single-Family Home | $4,700,000 | 06/25/25 | 6 | 7 | 9,200 | |
0.34 | Single-Family Home | $2,460,000 | 11/12/25 | 5 | 5 | 7,788 | |
0.16 | Single-Family Home | $1,962,000 | 12/16/25 | 5 | 3.5 | 3,702 | |
0.48 | Single-Family Home | $2,460,000 | 06/27/25 | 6 | 6.5 | 5,573 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKET@properties Christie's International Real Estate, Closed- FOR SALE0.55 ACRES@properties Christie's International Real Estate, Active
SOLDMAR 5, 2026@properties Christie's International Real Estate, Closed
SOLDDEC 16, 2025@properties Christie's International Real Estate, Closed
OFF MARKET@properties Christie's International Real Estate, Closed
OFF MARKET@properties Christie's International Real Estate, Closed
OFF MARKET@properties Christie's International Real Estate, Closed
OFF MARKETBaird & Warner, Closed
Assigned Schools
These are the assigned schools for 395 Greenleaf Ave.
- New Trier Township High School Winnetka
- 10-12
- Public
- 2730 Students
8/10GreatSchools RatingParent Rating AverageNew Trier high school is full of students who bully others relentlessly. The administration sweeps all sorts of problems under the rugs. They really only care about students who are athletes and parents who donate money. Many move here because of the schools. Our family can’t wait to leave because of how awful the administration and teachers have treated my children.Parent Review2mo ago - New Trier Township H S Northfield
- 9
- Public
- 880 Students
NAGreatSchools RatingParent Rating AverageIf it was good enough for Charlton Heston, it's good enough for you.Other Review2y ago - South Elementary School
- PK-2
- Public
- 403 Students
NAGreatSchools RatingParent Rating AveragePicture perfect school in picture perfect town. Principal and staff know all the children's names and parent's names. Lots of opportunities for parent involvement and volunteering and most moms are there regularly. Incredible technology presence due to generous PTO and foundation. Smart boards in every room and iPads and computers available for teachers to sign out and use for lessons. The PTO sponsors free before school clubs such as math, guitar, environment, video announcement, yoga. The park district supplements half day kindergarten and after school time with nearby sports, art, chess and computer classes. Specials include Spanish, Art, Music, Library and Gym. 1st and 2nd grade gets gym every day. Teachers are specifically matched to students for the following school year by using a long process of talking to all the specials teachers. All teachers make effort to differentiate within the classroom for students learning above grade level but wish they would bring back the differentiation (gifted) specialist. The curriculum includes SEL Social and Emoional Learning where students are encouraged to communicate with each other about their feelings. Bullying is not tolerated.Parent Review11y ago - Central School
- 5-8
- Public
- 561 Students
8/10GreatSchools RatingParent Rating Averagesome the kids at this school are very materialistic, there are a few groups of nice kids but bullying happens alot. i am in 8th grade and i see people struggling every day and the kids can be very nasty. i have a very good group of friends but the majority of kids can be mean. i like the academics and teachers are very good. overall i have had a good experienceStudent Review3y ago - West School
- 3-4
- Public
- 252 Students
9/10GreatSchools RatingParent Rating AverageStudents and parents are very cliquey, and teachers follow this social direction. I found the principal to be a glad handler and the PTO keeps his 'family jewels' in their purses. More emphasis placed on which parents are friends and less on academics. For the price of living here, the education should be better, shouldn't it? I also found that many students lack manners and empathy, instead being pushed to be number one no matter what it takes. If you are looking for strong academics and integrity, look elsewhere.Parent Review8y ago 
Check out schools near 395 Greenleaf Ave.
What Locals Say about Glencoe
At least 51 Trulia users voted on each feature.
98 % Say it's dog friendly
91 % Say people would walk alone at night
89 % Say there are sidewalks
86 % Say yards are well-kept
85 % Say kids play outside
84 % Say there's holiday spirit
82 % Say parking is easy
82 % Say there's wildlife
80 % Say it's walkable to restaurants
76 % Say it's quiet
76 % Say car is needed
70 % Say streets are well-lit
69 % Say they plan to stay for at least 5 years
67 % Say neighbors are friendly
65 % Say it's walkable to grocery stores
60 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Jena Radnay, @properties Christie's International Real Estate
Agent Phone: (312) 925-9899
Based on information submitted to the MLS GRID as of 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Click here for more information
395 Greenleaf Ave, Glencoe, IL 60022 is a 7 bedroom, 9 bathroom, 6,500 sqft single-family home built in 1912. This property is currently available for sale and was listed by MRED as distributed by MLS GRID on Jun 22, 2026. The MLS # for this home is MLS# 12677721.