Browse All Winnetka IL 5 Bedroom Properties for Sale

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

$1,995,000

5 Beds ⋅ 3 Baths ⋅ 12775682 MLS ⋅ ACTIVE Status

A rare offering on one of East Winnetka's most desirable streets, just two blocks from Lake Michigan. This exceptional property presents a unique opportunity to either thoughtfully renovate an existing home or create a custom residence with the potential for approximately 8,400 square feet of finished living space. Set on a beautiful, private lot surrounded by lush greenery, the property offers the perfect canvas for reimagining a home in an extraordinary setting. With no comparable lots currently available, and neighboring properties valued at over $5 million, the possibilities are truly exceptional. Enjoy an easy walk to downtown Winnetka, Greeley School, New Trier High School, the Metra train, Lake Michigan, parks and more. A rare opportunity to bring your vision to life in an unmatched location, whether through a beautiful renovation or a custom new build. Existing home is sold as-is, with no inspections.

510 Ash Street, Winnetka

$2,750,000

5 Beds ⋅ 6 Baths ⋅ 12783379 MLS ⋅ CONTINGENT Status

Situated on over half an acre on picturesque private Fisher Lane in the heart of Hubbard Woods, this gracious, grand yet warm 5 bedroom home is flooded with natural light and pairs impressive scale with timeless architecture and beautifully connected living spaces. Walls of windows frame lush green views of the ravine throughout, while soaring ceilings, hardwood floors and elegant millwork give the home a sense of presence from the moment you enter. The expansive 2 year old kitchen is the heart of the home, anchored by a spectacular oversized 11 foot island and opening to a sun-drenched breakfast room with fireplace and French doors to the outdoors. Generous formal and casual living spaces offer incredible flexibility for both everyday life and entertaining including a formal living room w/ fireplace, formal dining room, distinguished office/library, large family room w/ custom built-ins flanking the fireplace & attached 3-car garage. The dramatic second-floor gallery, vaulted ceilings and magnificent arched window add an unexpected architectural moment on the second floor where you'll find 5 generously sized bedrooms, 4 full bathrooms, a laundry room & abundant storage/closets. The massive primary suite is outfitted with a steam shower, soaking tub, dual vanities & dual walk-in closets. The finished lower level offers even more living space with a rec room, gym, wine storage & massive storage room. This is a truly special home that feels substantial yet inviting, classic yet fresh, and designed to be lived in beautifully.

936 Fisher Lane, Winnetka

$3,999,000

5 Beds ⋅ 9 Baths ⋅ 12774096 MLS ⋅ ACTIVE Status

1128 Mt. Pleasant Road, Winnetka

$1,400,000

5 Beds ⋅ 5 Baths ⋅ 12736036 MLS ⋅ PENDING Status

Set on approximately half an acre in sought-after Hubbard Woods, this five-bedroom + office, 4.1-bath home offers exceptional space, a versatile floor plan, and an outstanding North Shore location. The thoughtfully designed main level features a private office or living room, formal dining room, updated eat-in kitchen, and spacious family room overlooking the backyard, in-ground pool, oversized deck, and patio, perfect for gatherings with friends and family. A convenient mudroom provides direct access to the attached two-car garage. Upstairs are five bedrooms, an office and a dedicated laundry room, while the walk-up attic offers abundant storage and exciting potential for additional finished living space. Ready for its next chapter, the home presents a wonderful opportunity to update and personalize while enjoying a Hubbard Woods address rarely available at this price point-all within walking distance of the train, shops, and Winnetka schools.

874 Boal Parkway, Winnetka

$1,200,000

5 Beds ⋅ 4 Baths ⋅ 12758782 MLS ⋅ PENDING Status

***Build your dream home!!!*** Amazing opportunity in the East Winnetka neighborhood, tear down and build your forever home! Original 1913 home standing on 11,555 sf 70x165 Corner LOT. Prime Winnetka location, walking distance to lake, parks, school, Metra stop and downtown Winnetka. 'As-IS/Where-Is' Estate Sale.

590 Willow Road, Winnetka

$1,950,000

5 Beds ⋅ 3 Baths ⋅ 12703898 MLS ⋅ PENDING Status

An extraordinary Colonial offering timeless elegance, exceptional estate-like privacy, and breathtaking views along the 12th hole of the Winnetka Golf Course. Set on nearly one acre of beautifully landscaped grounds and positioned approximately 250 feet from the road, this property feels like a private retreat yet is just minutes from downtown Winnetka, the Metra, premier shopping, dining, and award-winning schools. Designed for both elegant entertaining and everyday living, the home features generously scaled rooms, hardwood floors throughout, and an inviting floor plan. The living room with fireplace and custom built-ins flows seamlessly into the formal dining room, while the sun-filled family room showcases sweeping golf course views. An updated kitchen with a spacious breakfast area anchors the home, and a first-floor den provides flexible space for a home office, library, or fifth bedroom. The primary suite is a private sanctuary with a fireplace, sitting area, outdoor deck, and stunning views. Thoughtfully renovated and maintained by the current owners, this exceptional home offers a bucolic setting, golf course walks and cross-country skiing outside its back door. Cherished by the same owners for the past 28 years, a true testament to the home's timeless appeal.

1440 Tower Road, Winnetka

$2,595,000

5 Beds ⋅ 6 Baths ⋅ 12688601 MLS ⋅ ACTIVE Status

Basement renovation just done to add 6th bedroom that adjoins full bath! So much light enters basement through windows! A rare opportunity to own a home on one of the most sought after, serene country-like settings on the North Shore. The house is just steps from the Indian Hill Golf Club and part of the coveted Indian Hill neighborhood. Be close to other magnificent homes and wooded and mature landscaping. Only one owner since home was completed on this property in 2012. Stately and traditional two story brick home with 5 bedrooms and 5.1 baths. The large finished basement with overly generous storage allows for a 6th bedroom. The basement has a full bathroom and space that is plumbed and ready for installation of a kitchen. Your eyes are drawn to the gracious two story foyer finished in marble. The rest of the first floor is finished in hardwood oak and cherry except for the family room that has plank flooring. The wel designed first floor has spacious living room, dining room, family room, eat-in kitchen, den and mudroom. The enormous primary bedroom is a tranquil retreat with spa like bath with jacuzzi and walk-in shower finished in travertine tile. The new owner will greatly appreciate the two walk-in closets located in this escape space. There are four other bedrooms on the second floor. Mature landscaping and brick pavers offer welcoming outdoor space. The driveway also boasts of brick pavers. Approximately 4319 square feet of above ground living space and 2066 below in basement for a total of 6385 square feet of enjoyable space. So close to schools, shopping, and even the beach. Enjoy the incomparable Winnetka lifestyle. Hurry, because this house, designed for everyday living and gracious entertaining, will not last long!

73 Locust Road, Winnetka

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Browse All Winnetka IL 5 Bedroom Properties for Sale

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