Lake Forest, IL 60045 1266 Winwood Drive
$1,775,000
Sold: Jun 27, 2025



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Presented By: Baird & Warner
Home Details
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)
Presented By: Baird & Warner
General for 1266 Winwood Drive
Additional Parcels Y/NNo
Architectural StyleContemporary
Assoc Fee Paid PerNot Applicable
Association Fee IncludesNone
CityLake Forest
Close Price1850000
Community FeaturesPark, Pool
Construction MaterialsGlass, Stone, Wood Siding
CoolingCentral Air, Zoned
CountyLake
DirectionsTake Waukegan Road to Winwood Drive, go east to property
Electric200+ Amp Service
Elementary SchoolEverett Elementary School
Elementary School District67
Full Baths6
Garage Spaces4
HeatingNatural Gas, Forced Air
High SchoolLake Forest High School
High School District115
Living Area4993
MLS AreaLake Forest
Middle/Junior High SchoolDeer Path Middle School
Middle/Junior School District67
ModificationTimestamp2025-07-02T08:51:02.049Z
New ConstructionNo
Other StructuresPool House, Garage(s)
OwnershipFee Simple
PossessionClosing, Immediate, Negotiable
Property TypeResidential
Property TypeDetached Single
RoofAsphalt, Rubber
SewerSeptic Tank
Standard StatusClosed
StatusClosed
Tax Annual Amount24822
Tax Year2023
Total Rooms12
TownshipShields
Year Built1965
Interior for 1266 Winwood Drive
BasementFinished, Full
Bedrooms Possible5
Fireplace FeaturesWood Burning, Gas Starter
FlooringHardwood
Half Baths1
Interior AmenitiesCathedral Ceiling(s), Built-in Features, Walk-In Closet(s), Open Floorplan
Laundry FeaturesMain Level, Gas Dryer Hookup, Electric Dryer Hookup, Sink
LivingAreaSourceAssessor
Room TypeLoft, Bedroom 5, Breakfast Room, Recreation Room, Foyer, Utility Room-Lower Level, Storage, Walk In Closet, Terrace, Other Room
Total Baths7
Total Bedrooms5
Total Fireplaces2
Exterior for 1266 Winwood Drive
Exterior AmenitiesFire Pit
Foundation DetailsConcrete Perimeter
Lot Dimensions327 X 319 X 230 X 49 X 557 X 417
Lot FeaturesCul-De-Sac, Forest Preserve Adjacent, Nature Preserve Adjacent, Landscaped, Wooded, Mature Trees
Lot Size Acres4
Parking FeaturesGravel, Circular Driveway, Garage Door Opener, On Site, Garage Owned, Attached, Detached, Garage
Total Parking4
Water SourcePublic
Waterfront Y/NNo
Additional Details
Price History

SQFT • 4,993