$2,550,000 SOLD Jun 2026
Listed at $2,395,000

500 Maple Street, Winnetka, IL 60093

Closed
5 beds 3.5 baths 5,646 sqft (estimated) Built 1920 Residential MLS #MRD12631320 5 days on market
Listing courtesy of Compass · 847-446-9600 · MLS #MRD12631320 · Status: Closed
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!

Property details

Interior

Appliances
Double Oven, Microwave, Dishwasher, Refrigerator, Freezer, Disposal, Gas Cooktop
Interior features
Vaulted Ceiling(s), Built-in Features, Walk-In Closet(s), Bookcases, Historic/Period Mlwk, Special Millwork, Separate Dining Room
Flooring
Hardwood, Carpet
Fireplaces
2
Fireplace details
Wood Burning, Gas Log
Basement
Partially Finished, Full
Laundry
In Bathroom
Additional rooms
Breakfast Room, Office, Sitting Room, Foyer, Mud Room, Bedroom 5
Total rooms
12

Building & exterior

Style
Colonial
Age
100+ Years
Exterior
Brick
Exterior features
Lighting
Roof
Shake
Windows
Bay Window(s), Display Window(s), Plantation Shutters, Screens, Skylight(s)
Patio & porch
Patio
Other structures
Pergola
Exposure
South,East,West

Parking

Garage spaces
2
Total spaces
2
Parking details
Brick Driveway, Garage Door Opener, Yes, Garage Owned, Detached, Garage

Lot & location

Lot dimensions
97x160
Lot description
Corner Lot, Landscaped, Mature Trees, Garden
Township
New Trier
County
Cook

Utilities

Heating
Radiator(s)
Cooling
Small Duct High Velocity
Water
Lake Michigan
Sewer
Public Sewer

HOA & community

Assessment includes
None
Community features
Park, Curbs, Sidewalks, Street Lights, Street Paved

Schools

Elementary
Greeley Elementary School (36)
Junior high
Carleton W Washburne School (36)
High school
New Trier Twp H.S. Northfield/Wi (203)

Taxes & terms

Annual taxes
$40,526 (2024)
Parcel number (PIN)
05211090100000
PIN
05211090100000
Ownership
Fee Simple
Possession
Closing
Special conditions
List Broker Must Accompany
Listed
5/17/2026
Sold
6/18/2026
Sold price
$2,550,000
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