Winnetka Homes with Colonial Style

Welcome to Winnetka, Illinois – a picturesque village nestled along the shores of Lake Michigan in Cook County. Known for its stunning landscapes, charming downtown, and strong sense of community, Winnetka is a place where history meets modern living. With a rich heritage dating back to the late 19th century, this vibrant community boasts tree-lined streets, award-winning schools, and an array of recreational opportunities, making it an ideal location for families and professionals alike.

One of the standout features of Winnetka is its architectural diversity, particularly the enchanting colonial-style homes that grace the neighborhood. These timeless residences, characterized by their symmetrical facades, gabled roofs, and classic brick or clapboard exteriors, exude an air of elegance and sophistication. With spacious interiors, well-manicured lawns, and inviting front porches, colonial homes in Winnetka offer a perfect blend of charm and functionality.

Living in a colonial-style home in Winnetka means embracing a lifestyle steeped in tradition while enjoying the conveniences of contemporary amenities. Many of these homes have been meticulously maintained or thoughtfully updated, ensuring that they meet the needs of today’s discerning buyers. The sense of community in Winnetka is palpable, with local events, farmers markets, and parks that encourage neighborly connections.

Whether you're strolling along the scenic lakefront, exploring local boutiques, or enjoying a meal at one of the charming eateries, Winnetka provides a serene escape from the hustle and bustle of city life. Discover the allure of colonial-style living in this idyllic village, where every home tells a story and every street invites exploration. Welcome to Winnetka – your new home awaits!

Newest Winnetka Homes with Colonial Style

$1,995,000

5 Beds ⋅ 5 Baths ⋅ 12786632 MLS ⋅ ACTIVE Status

Completely reimagined and thoughtfully designed, 1288 Sunview is an exceptional Winnetka home set on a picturesque half-acre lot. The property has been redeveloped from top to bottom with a focus on design, functionality and quality, creating a home that feels entirely new while maintaining the character and setting of the original property. The spacious floor plan offers 5 bedrooms, 3 full bathrooms and 2 half bathrooms, including four bedrooms upstairs and a fifth bedroom with ensuite bath on the main level that can function as a second primary suite. Two beautiful masonry fireplaces serve as focal points within the home, adding warmth, character and a timeless architectural element to the thoughtfully designed spaces. Multiple living spaces include two family rooms, a dedicated office and a fully finished basement, providing exceptional flexibility for today's lifestyle. The home's design creates an easy flow between the living, dining, kitchen and family spaces, while the main-level bedroom offers versatility as a guest suite, bedroom or second primary. The upper level features a spacious primary suite along with three additional bedrooms and a full hall bathroom. A convenient second laundry area is located on the bedroom level, while the fully finished basement provides additional recreation and living space, along with laundry, storage and mechanical areas. Outdoor living is a major highlight, with an expansive back patio, generous backyard and rooftop deck overlooking the property. The huge half-acre lot provides an uncommon amount of outdoor space in this Winnetka setting and is ideal for entertaining, relaxing or enjoying time with family and friends. Additional features include a two-car attached garage with EV charging hookup, beautiful hardwood flooring and thoughtfully designed spaces throughout. Set in an exceptional Winnetka location, 1288 Sunview is just minutes from New Trier schools, Skokie Playfields, parks, downtown shopping and dining, Metra and the lakefront. A rare combination of thoughtful design, substantial living space, architectural character and an exceptional half-acre setting, 1288 Sunview has been completely reimagined for modern living and is truly move-in ready.

1288 Sunview Lane, Winnetka

$2,699,000

6 Beds ⋅ 6 Baths ⋅ 12680099 MLS ⋅ ACTIVE Status

Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush, manicured grounds set the stage. Inside, the craftsmanship is unmistakable. You'll find expansive living spaces defined by rich architectural details and massive windows that frame the private, park-like backyard. The chef's kitchen is a masterpiece of function and style, flowing effortlessly into inviting family spaces that feel warm despite their scale. A first floor bedroom includes a private full bath and access to the patio. The primary suite serves as a genuine retreat, complete with a spa bath and enough closet space to satisfy any wardrobe. A sitting area surrounded by windows and a walkout overlooks the exquisite property. Each additional bedroom is en-suite and generously sized, ensuring everyone has their own corner of comfort. The third level includes flexible space with 3 lovely rooms and a full bath. There is an extra bonus space above the attached garage-perfect for a studio! Outside, the property truly shines. The expansive patio and rolling lawns create an incredible backdrop for summer garden parties or a quiet evening under the stars. Living here means more than just enjoying a beautiful residence; it's about the Winnetka lifestyle. You're minutes away from world-class schools, boutique shopping in the village, the shores of Lake Michigan, and the Metra for an easy commute to the city. It's sophisticated, it's private, and it's ready for its next chapter.

82 Woodley Road, Winnetka

$2,569,900

6 Beds ⋅ 6 Baths ⋅ 12637769 MLS ⋅ ACTIVE Status

The time is NOW to jump on this "southern charm" architectural beauty on exclusive Woodley Road. Beautifully appointed on a magnificent 1.5 acre lush lot with rolling greens, this estate is in prime position to be elevated to the next level of luxury. With over 8500 square feet of classic tasteful space over three floors of living, this house could never be duplicated close for the list price as the land value alone is worth at least $2 million dollars. Step inside to a grand foyer entrance where timeless black and white checkered marble floors meet a dramatic double atrium staircase wrapped in elegant wrought iron setting the tone for the architectural beauty that unfolds throughout. Gracious comfort exudes throughout this 13 room estate with that desirable southern exposure that allows natural sunlight to flood through the endless windows outlining the incredible backyard. Step down to a beautiful formal living room with a stone Parisian FP & custom French doors that open up to the cozy sunroom with picturesque windows overlooking the backyard. Finely appointed dining room with Visual Comfort light fixture layered with de Gournay wallpaper, antique marble fireplace and another set of French doors open out to the bluestone patio and deep backyard. Finely crafted white Chef's kitchen by O'Brien Harris with Villa Blanca marble, Clark & Barlow hardware, antique mirrored backslash and Holly Hunt pendents. Seamless transition to family rm ideal for cooking and entertaining at the same time. Command center mudroom, 2 powder rooms, and brand new laundry room also on this level. Two staircases lead the way up to large 2nd floor with intimate "Ralph Lauren" inspired den richly finished in restored paneled chestnut walls & handsome built-ins w/ dark marble FP. Large primary suite with room for even more expansion over porch is completed with Ann Sacks white bath and gracious marble FP with custom built-ins accented by a built-in window bench. 3 additional bedrooms with one being a large family bedroom w/ en-suite bath. The other 2 beds share pretty all white redone bathroom. Up to the oversized fully finished 3rd floor with 2nd family room and 2 beds ideal for in-law quarters or nanny. Lower level with mechanicals and ample storage space. The vibe of this home is effortlessly inviting-warm, layered, and livable across all 3 finished levels, seamlessly blending indoor & outdoor living. And with ample space to add a pool, the vision of true Southern comfort could be fully realized, elevating this already timeless retreat into a personal resort unlike any other.

62 Woodley Road, Winnetka

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Winnetka Homes with Colonial Style

Newest Winnetka Homes with Colonial Style

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