500 Maple Street Winnetka, IL 60093
Listing Courtesy of: MLS LogoMidwest Real Estate Data as distributed by MLS GRID / Compass

  500 Maple Street Winnetka, IL 60093

Active (4 Days)
$2,395,000 (USD)
5
BED
5
BATH
5,646
SQFT

Description

Exceptional East Winnetka Georgian on serene and lush . 4-acre grounds (96x160) with sweeping views of the Village Green. Architecturally significant and award-winning William Aiken classic restored and preserved to the modern standard, including a 2007 addition. Just a short walk to everything - town, train, beaches, school, and more - with your own private backyard garden oasis, this home offers a unique blend of timeless charm and contemporary luxury overlooking the iconic Village Green vistas. This classic architectural gem has been meticulously renovated and lovingly maintained to showcase architectural details, with every graciously scaled room beautifully appointed with breathtaking panoramic views. From the moment you enter the classic foyer with detailed millwork and soaring ceilings, the seamless flow of the home provides an ideal layout for everyday living and formal entertaining. The expansive living room features gorgeous built-in bookshelves, a beautiful wood-burning fireplace (overmantle designed by the homeowner), and glass French doors along every wall, offering incredible natural light and floor-to-ceiling Village Green views. Enjoy stunning vistas at any time of the year from either of the two 4-exposure sunrooms (one off LR and one off DR). A separate formal dining room, conveniently located with access to the kitchen, offers enough space for all of your entertaining needs, and opens to the second sunroom. The family room (2007) is a showstopper with vaulted ceilings and skylights, a handsome stone fireplace (gas), detailed built-in bookshelves, and oversized windows highlighting breathtaking views of the award-winning backyard. The bright kitchen with center island and wall-to-wall built-ins is perfectly positioned between the dining room, family room, and back hall mudroom. The gracious front hall staircase invites you upstairs to find the primary suite with bay window overlooking the gorgeous grounds, private bath, and walk-in closet. Two additional well-sized bedrooms share a Jack-and-Jill bath, as well as a hall bath with washer/dryer offering potential for a full second floor laundry room. Retreat up to the third floor with two bedrooms and a full bath - the ultimate treetop suite! The lower level offers a large finished recreation room that was dug out in 2007 while the expansive unfinished area has unlimited potential and endless possibilities. The backyard is a true private oasis - a sanctuary from the hustle and bustle of everyday life - offering serene tranquility and peaceful moments. Featuring bluestone terraces and limestone pathways, the backyard reveals a true secret garden with lush plantings, 3 waterfalls, a koi pond, and a bridge to the Japanese teahouse / gazebo. This home was thoughtfully renovated in 1989 and updated meticulously over the years, including an award-winning 2007 addition, 2003 detached garage, and updated Marvin windows. Experience elegance and comfort in an A+ location, just steps from town, train, schools, and Maple Beach!

MLS #:
12631320
Taxes
$40,527(2024)
Lot Size
0.4 acres
Type
Single-Family Home
Year Built
1920
Style
Colonial
School District
203,36
County
Cook County

Listed By

Paige Dooley, Compass
Source
Midwest Real Estate Data
Last checked May 20 2026 at 10:26 PM GMT+0000
Bathroom Details
  • Full Bathrooms: 3
  • Half Bathrooms: 2
Interior Features
  • Walk-In Closet(s)
  • Built-In Features
  • Historic/Period Mlwk
  • Special Millwork
  • Separate Dining Room
  • Bookcases
  • Appliance: Refrigerator
  • Appliance: Dishwasher
  • Appliance: Disposal
  • Appliance: Microwave
  • Appliance: Double Oven
  • Appliance: Freezer
  • Appliance: Gas Cooktop
  • Laundry: In Bathroom
  • Vaulted Ceiling(s)
Lot Information
  • Mature Trees
  • Garden
  • Corner Lot
  • Landscaped
Property Features
  • Pergola
  • Fireplace: Living Room
  • Fireplace: Family Room
  • Fireplace: 2
  • Fireplace: Wood Burning
  • Fireplace: Gas Log
Heating and Cooling
  • Radiator(s)
  • Small Duct High Velocity
Basement Information
  • Partially Finished
  • Full
Exterior Features
  • Roof: Shake
Utility Information
  • Utilities: Water Source: Lake Michigan
  • Sewer: Public Sewer
School Information
  • Elementary School: Greeley Elementary School
  • Middle School: Carleton W Washburne School
  • High School: New Trier Twp H.s. Northfield/Wi
Parking
  • Garage Door Opener
  • Garage Owned
  • Garage
  • Brick Driveway
  • Detached
  • Yes
Living Area
  • 5,646 sqft
Location
   
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Disclaimer: Square footage is based on information available to agent, including County records. Information has not been verified by agent and should be verified by buyer.
Based on information submitted to the MLS GRID as of 5/20/2026 22:26. 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.