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$1,850,000
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Property Description
Midcentury Modern Estate sitting in a secluded and serene setting next to the Middlefork Savanna Forest Preserve, one of the most beautiful nature preserves on Chicago's North Shore. This custom built 5-bedroom, 4.5 bath residence offers an unparalleled blend of architectural sophistication with curated views of nature from every window. Designed by renowned local architect Arnold Shaffner, this residence is a masterclass in design, seamlessly integrating clean lines, warm wood tones, and expansive glass walls that invite the forest inside. At the heart of this estate lies a stunning open-air courtyard-a peaceful retreat perfect for morning coffee or evening gatherings under the stars. The home flows effortlessly from indoor to outdoor living, culminating in a resort-style backyard with a sparkling pool, sleek lounge areas, and a fully appointed pool house with kitchen, great room and 2 baths, ideal for entertaining. Upon entering the home, enjoy stunning interior views starting with the floor to ceiling 20-foot windows, Italian terrazzo marble entryway and vaulted two-story living room with hand-built stone fireplace and multiple skylights. Gorgeous views of the courtyard and private lane from the dining room. Spacious, bright, eat in kitchen with tons of storage and counter space, including a large island and highest end stainless steel appliances, including brand new sub-zero refrigerator is the perfect place to cook while also enjoying views of the pool and east courtyard. Adjacent family room has sliders to pool area. The open second floor has a balcony that brings all the bedrooms together with a seating area in the middle. Primary bedroom suite is just shy of 700 ft.2 with a 14ft by 11ft walk-in closet with skylight and separate, floor-to-ceiling shoe closet that will hold up to 180 pairs of shoes. Lofted den with incredible views of the courtyard and grounds makes a perfect office or relaxation area. Three additional spacious bedrooms with two full baths and guest bedroom with ensuite bath complete the second floor. The finished basement contains an additional en-suite bedroom and large recreational area perfect for your home gym and wonderful family room space with fireplace. Current owner installed around $400,000 worth of improvements including major landscaping and beautification project of the 4-acre setting, designed by renowned Lake Forest Landscape Artist, Craig Bergmann, a brand new driveway, creation of fenced courtyard with beautiful southeast facing patio and fire pit, new roof on main house and pool house as well, two new HVAC systems and one new hot water heater, as well as new walnut hardwood flooring throughout the entire 2nd floor. This rare property is a private sanctuary where modern luxury meets the timeless beauty of nature. (Chandelier in kitchen eat-in area is excluded from the sale)
Full Property Details
Full Property Details for 1266 Winwood Dr
General
- Sold For: $1,850,000
- Taxes: $24,822 (2023)
- Status: Closed
- Type: Single Family
- Source: MRED
- MLS ID: 12364818
- Added to Site: 283 day(s) ago
Interior
- Interior Features: Cathedral Ceiling(s), Built-in Features, Walk-In Closet(s), Open Floorplan
- Fireplace: Yes
- Fireplace(s): Family Room, Living Room, Wood-Burning, Gas Starter
- Flooring: Hardwood
Rooms
Bathrooms
- Total Bathrooms: 7
- Full Bathrooms: 6
- Half Bathrooms: 1
- Basement Baths: Yes
Bedrooms
- Total Bedrooms: 5
Exterior
- Exterior Features: Fire Pit
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 4
- Total Spaces: 4
- Parking Features: Gravel, Circular Driveway, Garage Door Opener, On Site, Garage Owned, Attached, Detached, Garage
- Parking On-Site: Yes
Location
- Area: Lake Forest
- County: Lake
- Driving Directions: Take Waukegan Road to Winwood Drive, go east to property
School Information
- School District: 67
- Midd School District: 67
- Elementary School: Everett Elementary School
- Middle School: Deer Path Middle School
- High School: Lake Forest High School
- Private School: Lake Forest High School
Community
- Assoc. Fees Include: None
Heating & Cooling
- Cooling Type: Central Air Conditioning, Zoned
- Heating Type: Natural Gas, Forced Air
Utilities
- Water: Public
Structural Information
- Architectural Style: Contemporary
- Construction: Glass, Stone, Wood Siding
- Exterior Const.: Glass, Stone, Wood Siding
- Basement Desc.: Finished, Full
- Foundation: Concrete Perimeter
- Roof: Asphalt, Rubber
- Windows: Skylight(s)
- Sub-Flooring: Hardwood
- Square Feet: 4,993
- Sq. Ft. Source: Assessor
- Year Built: 1965
- Built Before 1978: Yes
- Remodeled/Updated: 2022
Additional Structures
- Other Structures: Pool House, Garage(s)
Lot Features
- Lot Size (Acres): 4
- Lot Size Range: 4.0 to 4.99 Acres
- Lot Dimensions: 327 x 319 x 230 x 49 x 557 x 417
- Fence: Yes
- Lot Features: Cul-De-Sac, Forest Preserve Adjacent, Nature Preserve Adjacent, Landscaped, Wooded, Mature Trees
- Fencing (Description): Fenced
Water Features
- Water Front Desc.: Pond
Financial Considerations
- Parking Included: Yes
- Assessment Year: 1965
- Tax Amount: $24,822
- Tax Year: 2023
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: List Broker Must Accompany
- Property ID: 12301030010000
Listed by Baird & Warner
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Schools
Schools serving 1266 Winwood Dr
School Districts:Lake Forest Community High School District 115, Lake Forest School District 67
| Name | Grades | Distance |
|---|---|---|
Deer Path Middle School East 95 West Deerpath Road, Lake Forest, IL 60045 | 5-6 | 1.9 mi |
Everett Elementary School, Lake Forest, IL 1111 Everett School Road, Lake Forest, IL 60045 | K-4 | 3.3 mi |
Deer Path Middle School West 155 West Deerpath Road, Lake Forest, IL 60045 | 7-8 | 1.8 mi |
Lake Forest High School 1285 North McKinley Road, Lake Forest, IL 60045 | 9-12 | 2.1 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1266 Winwood Dr
Date
Details
Price
Change
Source
6/27/2025
Sold
$1,850,000
4.23%
MLS
5/14/2025
Listed
$1,775,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
1266 Winwood Drive, Lake Forest, IL 60045 (MLS# 12364818) is a Single Family property that was sold at $1,850,000 on June 27, 2025. Want to learn more about 1266 Winwood Drive? Do you have questions about finding other Single Family real estate for sale in Lake Forest? You can browse all Lake Forest real estate or contact a Coldwell Banker agent to request more information.


