500 Maple Street, Winnetka, IL 60093
- 5 beds |
- 5 baths |
- 5,646 sqft
Single-Family Home 
Built in 1920 
0.4acre lot
2 car garage 
$424/sqft 
Listed ——
Property 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!
- Listing Status:
- Active
- Data Last Updated:
- May 20, 2026 at 12:19PM
- Listing Office:
- Compass : 847-609-0963
- Listing Agent:
- Paige Dooley : 847-609-0963
- MLS ID:
- 12631320
- General: Lighting
- Style: Colonial
- Other Structures: Pergola
- Parking: Brick DrivewayGarage Door OpenerYesGarage OwnedDetachedGarageParking spaces: 2
- Roofing: Shake
- Windows: Bay Window(s)Display Window(s)Plantation ShuttersScreensSkylight(s)
- General: 3 Stories
- HOA Amenities: ParkCurbsSidewalksStreet LightsStreet PavedNot Applicable
- Originating MLS: mred
- School District: 36
- County: Cook
- Zoning: 05211090100000
- Water: Lake Michigan
- Sewer: Public Sewer
- Source: mred
- Ownership: Fee Simple
This listing courtesy of Paige Dooley , Compass
Monthly Payment
- Principal & Interest $
- Property Taxes $
- Home Insurance $
- VA Funding Fee $
New - 2 days ago 
