Winnetka IL Real Estate & Homes for Sale

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.

Rarely available first floor primary! Unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners. Owner extremely motivated!!!

Welcome Home to this hidden gem in Lincoln Garden! Fabulous location right in the heart of town. Newly refreshed kitchen with open floor plan and first floor laundry and half bath. Quaint private patio off kitchen. Gorgeous hardwoods throughout living area and second and third levels. Hardwood stairs bring you to the 2 generous bedrooms and pristine vintage bath on the 2nd floor, tons of storage in multiple closets! Finished 3rd floor offers additional flex space for family room or office. All this and one garage space included. There are options for additional parking with the city as well.

HOME EXCLUDED FROM FLOOD ZONE/INSURANCE - DOCUMENTATION PROVIDED. Exclusive quality builder-designed home with fabulous curb appeal! This exceptional residence features an open-concept floor plan, 4 fireplaces, 2 additional parking spaces and dual laundry areas. The kitchen offers Sub Zero/Thermador stainless steel appliances and a custom designed island. Coiffured ceilings in the dining room and den add an elegant touch. The expansive finished lower level offers a versatile sleeping area and additional living space. Beautiful hardwood flooring extends throughout the main and upper levels. 9 foot ceilings throughout really expand the space! 2 additional bedrooms upstairs have ensuite bathrooms. The garage is equipped with EV charging, while a new fence enhances the privacy and curb appeal. Step outside to your own private backyard retreat, surrounded by lush, thoughtfully designed landscaping with an in ground sprinkler system - perfect for relaxing or entertaining. Built-in vegetable garden area next to garage! Close proximity to schools and downtown makes it convenient for walking.

Why would you rent at Winnetka One when you can OWN a beautiful 2 bed 1900 sq. ft. condo much bigger than a 2 bed unit right next door! One heated garage spot (#13) included with this beautifully renovated unit by notable North Shore Benvenuti & Stein with quality details and neutral finishes throughout. The entire space is finished with pristine engineered hardwood floors throughout main living areas & bedrooms which lifts the space beautifully. Formal entry with large coat closet opens to sun drenched great room with ample space for both living & dining. Custom wall of built-ins with display shelving and storage is ideal for office needs. B&S customized a fantastic eat-in kitchen with large breakfast bar island and cozy window bench area overlooking Oak street. Refined lightly stained maple cabinetry with RH hardware, brushed chrome faucets, Miele dishwasher, double oven, and Wolf induction cook-top w/custom hood. All is pulled seamlessly together with stainless steel appliances & layered with Cambria quartz counter tops. Huge, sun lit primary suite with large windows, and ensuite spa stone bath with large walk-in shower, Toto, soaking tub & floors outfitted in marble. 2nd bed is across from newer crisp stone bath with built-in vanity, walk-in shower, and custom glass tile inlay. This expansive unit boasts its own laundry room equipped with Bosch W/D, sink, custom cabinetry, countertop space for folding and extra supplies, and storage shelving. This third floor unit offers 48 inch wide hallways for ease of movement, pocket doors for maximum space, and a newer 3 zoned HVAC system allowing perfect zone control. Unit includes additional storage cage which is easily accessible in this well maintained building equipped with 2 large scale elevators. Bonus expansive back parking lot for your additional cars or guests which is ideal as this is right in downtown Winnetka. Recent 2026 building improvements include new roof, new entry security intercom, all halls/trim painted, and tuck-pointing (25/26). If you want to jump on the train, watch the huge music fest, grab lunch at Hometown, or just enjoy all that Winnetka offers this is a PRIME condo to buy! No rentals, No pets. Easy to show, vacant and can close ASAP.

Built to impress, this beautifully designed, custom crafted home is discreetly tucked in next to Crow Island Woods you will have nature at your doorstep and be perfectly situated on an amazing half-acre lot. This stunning 5 + bedroom, 6.3 bath home combines timeless architecture with thoughtful modern accents, offering a level of comfortable, elegant living in the North Shore's most sought-after location. Masterful custom cabinetry fills the bright, well equipped kitchen begging to be used for entertaining or casual family gathering. The primary suite boasts a view of the treetops and almost welcomes you out to the balcony which adjoins. The spa inspired primary bath has all the ammenities. When the weather starts getting nice the backyard patio extends the home to the outdoors and beautifully compliments the aesthetic. You really must see this home to appreciate how the approximately 6950 sq/ft on first and second floors and 2800 sq/ft of beautifully finished lower level can become the home of your dreams!

Completely reimagined and thoughtfully designed, 1288 Sunview is an exceptional Winnetka home set on a picturesque half-acre lot. The property has been transformed 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.

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!

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.

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.

A Home That Redefines Scale and Lifestyle. With over 17,000 square feet of meticulously designed living space-including 7,500 square feet dedicated to main-floor living and entertaining-this residence represents one of the most comprehensive lifestyle homes ever built in Winnetka. Designed and built by noted builder, every element was curated for collectors, entertainers, and owners who value privacy, wellness, and architectural presence-without compromise. Designed with a timeless, classic architectural aesthetic and infused with modern innovation for 2026 living, this residence delivers true first-floor living and entertaining with every amenity required for builders "Five Star Living Every Day". The main floor estate amenities feature builders signature 50-foot art gallery with museum-quality lighting, a spectacular kitchen connected to outdoor entertaining, a 60-foot in-ground pool, dining capacity for 30, dine-in wine cellar, billiards and bar lounge, home theater, golf and sports simulator room, private office and den, wellness center with steam, sauna, whirlpool spa, cold plunge, massage room, and fitness center, and a luxurious primary suite, all on the main level. Situated on a rare one-acre lot in the coveted Crow Island School District, the 3 stop elevator to the second floor offers four ensuite guest bedrooms, with additional guest accommodations and extensive storage on the 10' ceilings lower level. Extensive landscaping and heated outdoor living spaces for entertainment and pool and outdoor spa fun complete this unique opportunity. Offered at $16,900,000. Serious inquiries only