Winnetka IL Real Estate & Homes for Sale

Fabulous opportunity to own this 2 Bed/2 Bath condo in sought after Winnetka Mews building. Conveniently located near downtown Winnetka's shops, restaurants, train, bike path, park district facilities, Winnetka Community House and beaches. The two bedroom floor plan includes a large living room, dining room, kitchen, and East facing private balcony. The primary suite is highlighted by a spacious walk-in closet and primary bathroom with double vanity, separate shower and tub. The building amenities include an exercise room, outdoor pool, elevator, heated garage parking, and outdoor guest parking. All major capital improvements have been completed while maintaining a healthy reserve balance. Additional perks include two units per floor, an onsite engineer, and newly remodeled foyer and common areas. Garage parking and Storage included in the price.

New magnificent transitional home situated on 1 acre picturesque lot with approximately 15,000 square feet finished space. Exterior is constructed of stone and limestone with slate roof which represents timeless construction. The house features 6 bedrooms, 7.1 bath, 4 fireplaces, spectacular Neff kitchen with top-of-the-line appliances including Sub-Zero refrigerators/freezers, luxury Wolf range, espresso/cappuccino machine, drawer style microwave, and much more, walnut library has a built-in desk and filing cabinets. Spectacular finished lower level includes entertainment room with fireplace and TV, refrigerated wine cellar, full size wet bar, media room with 4K technology, surround sound and leather reclining chairs, Sport Court. The house also offers security system, back-up generator. home is prewired for Smart home system. House has 3 stops elevator. This house has it all! Agent owned.

Centrally located in a premiere "get to everything" A+ location, this quintessential North Shore coastal shingle home delivers the best of both worlds. Thoughtfully remodeled and reimagined by notable North Shore architect Paul Konstant that beautifully blends classic character with a refreshed, modern floor plan that marries timeless architecture with designer-perfected living. Step inside to a gracious foyer that opens to the formal living and dining rooms. Sun-drenched living room shines with restored original built-in bookshelves & accented by WBFP with a fab Chicago common brick surround creating a warm welcome. Living room flows effortlessly into stoic Polo lounge/office painted in a cozy Farrow & Ball liquorice, custom built-ins, huge bay window, custom Ralph Lauren window treatments & classic window seat. Elegant dining room, bathed in natural light, connects seamlessly to the butler's pantry opening to the Chef's kitchen - the hub of this extensive first floor. Crisp white cabinetry, s/s appliances, an oversized breakfast island outfitted in gorgeous Villa Bianco marble with seating for 4. Directly off the kitchen, mudroom with back door entrance and 2nd powder room. Bright breakfast room bathed in light w/ thoughtfully designed built-in command center connects directly to the new phenomenal Great room addition with soaring vaulted ceilings, intricate trim work, a window bench flanked by custom built-ins, a soapstone surround FP, and French doors that open to the covered back porch with FP that overlooks the lush, beautifully landscaped 1/2 acre grounds. Second floor with 4 bedrooms: two share a Jack & Jill bath, one ensuite, and bedrooms two and three share a cheerful sun-drenched tandem room with custom built-in desks - a perfect homework space or kids' hangout. Large primary suite is a true retreat with a stunning newly redone spa bath featuring Ann Sacks tile, thick white marble counters, soaking tub, dual vanity, and a marble-clad walk-in shower. Large walk-in closet and best yet, a private second-floor balcony. 3rd floor with 2 additional bedrooms that share a hall bath - ideal for guests. Incredible new lower level dug out with radiant heat, soaring ceilings with natural light in the large rec room. Pretty full bath with caesarstone grey c-tops, subway tile, and white cabinetry. HUGE storage space on the unfinished side with craft area and ample closets. Just steps from town, train, and all schools including Faith Hope, NSCD, New Trier & Loyola, 213 Linden is the kind of home that feels magical in every season - from summer nights in the backyard to cozy holidays by the fire. A timeless Winnetka classic that is turn key charming all American beauty!

Beautifully reimagined in 2023, this custom Hemphill-designed home blends modern elegance with timeless craftsmanship. This sophisticated Winnetka home is completely transformed, including new electrical and plumbing, an updated floor plan, bay windows, and new exterior doors, while maintaining the charm and character of original plaster crown moldings and Hemphill's signature wrought-iron staircase. Every space exudes calm, understated luxury. The chef's kitchen features quartzite counters, custom cabinetry, and Wolf/Sub-Zero appliances, flowing seamlessly into the light-filled family room framed by black-trimmed windows and natural wood tones. The living and dining spaces are anchored by a stunning fireplace and layered lighting that set the tone for relaxed sophistication. Upstairs, the serene primary suite has a luxurious spa-inspired bath, with a marble-slab shower, custom storage, and a private balcony. Each bathroom offers its own distinct character, from the dramatic powder room to the sleek secondary baths. All full baths feature heated floors for added comfort. The lower level is designed to feel like an extension of the main living space and features a refined theater lounge with a drop-down projector and custom wood-burning fireplace. 2-car attached garage completes this rare turnkey home near top schools, Hubbard Woods, downtown Winnetka shops and restaurants, metra, plenty of parks and Tower beach access. Schedule your private tour today and experience modern Winnetka living at its finest.

Nestled on a private lane east of Sheridan Road, this distinguished residence combines timeless sophistication with everyday livability. With over 6 bedrooms (including an in-law/guest suite) and 7.1 baths, the home is designed to accommodate a variety of lifestyles - whether hosting large gatherings, working from home, or enjoying intimate quiet time. A sunlit two-story foyer with a sweeping bridal staircase sets the stage, opening into expansive living and dining areas, and a richly appointed library/office. A great room with coffered ceilings and a wet bar offers additional space for entertaining. The chef's kitchen - ideal for both everyday cooking and special occasions - boasts a substantial island, white cabinetry, and premium appliances: professional gas range, double wall ovens, two dishwashers, full-size refrigerator and freezer, beverage fridge, and built-in microwave. Welcoming family room with dramatic fireplace offers casual dining and access to lovely patio. Practical features abound, including a large mudroom with stackable laundry and a full bath, conveniently serving the outdoor pool and spa. Upstairs, the serene primary suite features three walk-in closets, a luxurious bath with steam shower, and abundant vanity space. Two additional en-suite bedrooms, a full guest suite with kitchen, plus two more bedrooms, a hall bath, and second laundry room complete the level. The finished lower level offers a home theater, game room, gym, bedroom with full bath, bonus room, and extensive storage. Additional amenities include gated entry, heated garage and driveway, professional landscaping, sprinkler system, and exterior lighting. Built with exceptional quality and thoughtful design, this extraordinary property offers privacy, space, and proximity to the lake-an unmatched opportunity in one of Winnetka's most sought-after locations.

Incredible Coveted Home with 5 bedrooms, 5.2 bathrooms, 3 garages on 1/3 acre property boasts Winnetka address and Kenilworth School District. Built in 2004, this beautiful brick home feels like new construction with a complete first floor renovation in 2019 and upgrades throughout the home. As you enter the sun filled foyer, you are greeted with an open floor plan and 9'.5" ceilings. Flanking the foyer is the spacious dining room with gracious bay windows and a separate den with built-in bookshelves, fireplace and gorgeous wood beamed ceiling. The formal living room boasts floor to ceiling windows, limestone fireplace and opens into the fabulous kitchen. The kitchen is completely new from 2019 and is a chef's dream. A twelve-foot oversized island with a quartzite waterfall finish hosts custom cabinetry, generous workstation sink, custom cabinetry and island seating space. The incredible Miele appliances include a Six Burner Cooktop, 48" Dual Fuel Range with Steam Hook Up, Speed Oven, Warming Drawer, Convection Oven with Steam Hook Up and Griddle. The Miele Master Cool Built-In 30" Refrigerator and Miele Master Cool 30" Built-In Freezer make storing food a dream come true, especially when you utilize the walk-in pantry. There are two dishwashers and two sinks in the kitchen, both oversized with accessories, disposal, and an insta hot/cold filtered water dispenser. Last but not least, the built in Miele Combo steam oven adds to easy, healthy and efficient cooking. The eat-in kitchen area with custom, built-in banquet seating is nestled between the sunny bay windows. Anchoring the kitchen is the limestone fireplace making this room truly the heart of the home. From the kitchen patio doors, step out onto an outdoor entertaining space that is perfect for entertaining or relaxing in the great outdoors. The built-in bluestone bar area along with a wood burning fireplace, outdoor television, built-in gas grill, seven person all-season resort spa are included on the 1/3 of an acre outdoor playground. Moving back inside, the second floor primary suite has vaulted ceilings, separate closets and a primary bathroom with double sinks, oversized shower and Jacuzzi tub where you can gaze at the moon through the skylight. There are three additional bedrooms on the second floor, all en-suite. The laundry room is conveniently located on the second floor with folding area and built-in cabinets and sink. The lower level has an incredible recreation area with kitchenette, granite countertops, island for seating, cabinetry, a double sink, Fisher Paykel Double Dishwasher Drawers, a mini refrigerator, microwave, and a built-in wine closet. Enjoy the theatre space, exercise room, gracious 5th bedroom, full bathroom and storage galore! There are two separate garage areas: a two car garage and an additional one car garage all attached to the home equaling a 3 car attached garage with EV vehicle charger. The exterior front of the house welcomes you with an over sized circular brick driveway, with professional landscaping and lighting on the entire property. Newer roof, new hot water tanks, new thermostats and central vacuum system make this home move in ready! The home is conveniently located near schools, train, and a block and a half from Lake Michigan. This home is meticulously maintained in a prime location.

Gracefully tucked away on 1.55 acres of lush manicured grounds, 62 Woodley Road is a true Southern-inspired masterpiece reimagined for today's living. From the moment you approach the iconic black lacquered screen door with its Chippendale detail, you're drawn into a world of classic sophistication. 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 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.

Presenting one of Winnetka's most admired homes with an expansive back yard and spectacular pool. The home is majestically perched at the top of Arbor Vitae, making it our own "Castle on the Hill" built in 1915 by Otis & Clark Architects. This Edwin Hill Clark masterpiece, featured in Luxe magazine in 2021 and on the Winnetka Community Housewalk Home Tour in 2023, was painstakingly renovated in 2019, yet retains the charm and grandeur of the original architectural details that inspire classic new homes today. The stunning barrel-ceiling reception gallery, ideal for an art collector and entertaining, immediately sets the tone. Fine, grand rooms all designed for casually elegant living span the first floor. The centerpiece of this special home, an atrium great room with skylights and three series of windows, overlooks beautiful vistas of the rolling backyard, patios & pool. Soaring ceilings, intricate millwork, nine sets of double French doors, and incredible light make this floor absolutely stunning. The kitchen has been completely renovated with a La Cornue range, Sub Zero refrigerator, Miele steam/convection oven, Waterworks faucets, radiant floor heating, new custom cabinetry, and spectacular countertops & oven backsplash. Enjoy the beautiful decor and mural wallpaper in dining room, built-in bar and wine refrigerator in den, new gas fireplace and built-in cabinetry in family room, hand-painted "wallpaper" in powder room, and built-in Sonos ceiling speakers throughout the first floor. The second floor boasts a new primary suite spa retreat with Waterworks faucets, steam shower, new free-standing tub, heated marble floors, huge closet with custom island, built-in shoe organizer, floor-length jewelry storage, and incredible separate lounge/office space. Three en suite bathrooms were completely renovated on the second and third floors, along with an update and reconfiguration of the third floor with new gym space (which could double as a small bedroom) and large recreation room or play area. This home has it all! The huge, park-like backyard with large pool, renovated in 2021, has two new hardscape patio areas and a built-in gas firepit. Professionally landscaped in one of the best East Winnetka locations. Close to town, schools, Lake Michigan, and downtown Winnetka.

Nestled just blocks from Winnetka's famed lakefront, this 4-bed/1.5-bath single-family home at 979 Vine St offers approximately 2,100 sq ft of living space, hardwood floors, a spacious kitchen, and thoughtful layout across levels. Located a few blocks to Tower Road Park/ beach - Lake Michigan and Lloyd Park Boat Launch.. Steps to Green Bay Train - for biking, running, and casual strolls. Plus close to downtown amenities. Homes within a one-mile radius average about $1.7-2.2 million, making this residence a rare opportunity to live the lakefront lifestyle without the million-plus premium. Coming soon to auction. Contact listing broker for more details.

Exciting chance to refashion this light-filled ranch home to your personal vision. Large windows throughout the home offer beautiful views and light. The spacious kitchen opens to the vaulted family room. The master bedroom and second bedroom are on the first floor, plus two full baths, family room, living room, dining room, and screened porch. Outdoors, there is an expansive stone patio and pond overlooking the lush grounds. The house presents a unique opportunity to upgrade by adding additional rooms on the unfinished second floor walk-up attic. The current square footage of the home is 2,316 which can be expanded to 6,805 sq. ft (per the Village of Winnetka.) That is also the floor area for new construction on this lot. Whether you want to renovate, flip, build new, or rent it, 1295 Sunview offers you a range of options!

Perfectly nestled on one of Winnetka's finest enclaves, this stately 6-bedroom, 5.2-bath Georgian estate offers a rare fusion of architectural elegance, exceptional craftsmanship, and resort-style amenities. Set on nearly an acre of meticulously manicured grounds, the estate is introduced by a sweeping circular drive that highlights the home's classic brick facade, brand-new DaVinci slate roof, columned portico, and timeless symmetry. Together, these elements create a striking first impression and set the stage for interiors that exude sophistication at every turn. Step inside the grand "bookmatched" marble-floored foyer, where a dramatic staircase sets a refined tone for the home. To one side, the formal living room offers an inviting gathering space anchored by a marble fireplace, while the formal dining room is perfectly scaled for both intimate dinners and large-scale entertaining. A massive, richly paneled home office with dramatic coffered ceilings offers an impressive and inspiring workspace. At the heart of the home, the gourmet kitchen boasts professional-grade appliances, an oversized island, full wall of pantry storage, and a sunlit breakfast area all overlooking the magnificent pool and grounds. A butler's pantry ideally placed between the kitchen and dining room provides effortless entertaining. Just beyond, the kitchen opens to a cozy family room with a fireplace and wet bar, while French doors lead to an expansive covered terrace framed by graceful curved archways and cooled by ceiling fans. This spectacular outdoor living space features a brand-new outdoor kitchen fully equipped for grilling and al fresco dining, leading to the sparkling pool, surrounding patio and yard, creating a seamless setting for summer entertaining and secluded relaxation. A convenient first-floor laundry/mud room right off the 3-car heated garage with epoxy flooring and 2 powder rooms adds everyday ease. Upstairs, the elegantly appointed primary suite offers dual walk-in closets, a dedicated vanity area, and a spa-inspired bath with separate vanities and radiant heated floors. Four well-proportioned additional bedrooms, each with generous closets and either en-suite or adjoining baths, provide comfortable accommodations for family and guests. This level is further enhanced by expansive linen closets, abundant storage, and a dedicated luggage room. The impeccably finished lower-level rivals any private club, featuring a state-of-the-art home theatre, richly paneled billiards and game room, fully outfitted bar, expansive fitness studio, wine cellar, guest suite, and a dedicated woodshop for refined hobbyists or craftsmen. Located in one of Winnetka's most prestigious locations and served by its award-winning schools, this remarkable estate perfectly balances classic sophistication with modern luxury. Combining architectural pedigree, unparalleled amenities, and impeccably landscaped grounds, this is a home to be cherished for generations. Furniture available for sale.

This is the ultimate North Shore 2 acre lakefront estate with every single possible luxurious amenity with no expense spared...the pinnacle of owning a true entertainment destination AND also being in the most premier lakefront location in Winnetka steps to town, train, and award winning schools. Over 25,000 square feet of finished space with the latest addition of an incredible wellness wing right on the lake with incredible views of your private 137ft sandy beach. Indoor and outdoor pools, full gym & sauna, private patios, spa, gourmet chefs kitchen, 4 car garage, gated entry, grass tennis court, elevator, and huge volume throughout all floors. This house would cost way over $55M to rebuild with build costs, land value, hardscape, beach, new pools, and some features that could NEVER be duplicated today! A modern way to get what you want on the lake without the hassle of building...over the top sensational!

Better than NEW! Impeccably renovated 6BR/5.2BA center-entry colonial set on an oversized (66 x 159) professionally landscaped lot. This four-level home features abundant natural light, oversized windows, wide room openings, custom millwork and gleaming hardwood floors throughout. Spacious rooms, a current layout, high-end finishes and thoughtful design exist at every turn. First floor includes a gourmet kitchen, butler's pantry, formal dining room, sun-drenched living & family spaces, a private home office, and handsome mudroom & full 1st fl laundry room. Upstairs, the luxurious primary suite offers a spa-like shower, double vanity and walk-in his and hers closets. Additional bedrooms are generously sized, one bedroom is en-suite and the 3rd & 4th bedrooms share a large hall bath. There is additional 2nd floor laundry for ultimate convenience. Fully finished lower level and 3rd fl provide flexible living space for extra BR's, recreation, guests, or work-from-home needs. Both floors have gorgeous full bathrooms. Exceptional outdoor living space includes brick patio, lush landscaping and private, fenced yard. A rare blend of classic charm and modern luxury in a prime location, just blocks to Hubbard Woods town, train, shops, restaurants, school, parks, the forest preserve bike and running trails. Easy access to downtown Chicago.

Rehabbers-Opportunity Awaits! Have you been searching for a home on one of Hubbard Woods' most cherished streets? A place where your family can grow, in a community known for its charm and friendly community? This is that rare opportunity. This solid 4 bed, 2.5 bath home is full of potential and perfectly situated in a sought-after neighborhood with top-rated schools. With thoughtful updates and a little vision, this property can be transformed into something truly special-adding immediate value in a location that supports it. Offered AS-IS, this is an ideal chance to customize without overpaying for someone else's choices. It's priced to reflect the work it needs-making it a smart move for those who understand the value of investing in the right home, in the right location Don't miss the chance to create something amazing in one of the North Shore's most beloved communities. Come take a look and imagine the possibilities! AS-IS

Nestled down a winding, private road on 1.9 meticulous park-like acres, this grand, almost 10,000 square foot residence exudes luxury and timeless elegance. The front entrance is set apart from the road by a sweeping circular drive bordered by private hedges and mature trees. Upon entering the stately, two-story foyer with a 25' ceiling, bridal staircase, black and white marble floor, formal powder room and two coat closets, you are greeted by the sophistication that defines this home. The main level features a spacious, step down living room with inlaid floors, a marble, gas and wood fireplace, and two picture windows that fill the room with natural light. Pass through the living room to an adjoining, architecturally beautiful solarium with a slate floor, that offers panoramic views of the lush grounds surrounding the residence. The formal dining room also features inlaid floors, and picture window. The handsome family room with custom cabinetry, lighting, millwork, and a marble, gas and wood fireplace, provides the perfect space for entertaining and relaxation while overlooking a yard large enough for a pool. The family room seamlessly flows into a large kitchen area that includes not only a custom kitchen but also a breakfast room, butler's pantry, back staircase, and mud room. The butler's pantry has an ice maker, second dishwasher, and beverage refrigerator. Upstairs the luxurious primary bedroom suite boasts a marble, gas and wood fireplace, walk-in closet, and an adjoining sun room with stunning views of the grounds. It is perfect for family gatherings, office space or nursery. Adjacent to the dual sink primary bath with a vanity table, there is a winding staircase that leads upstairs to the third floor where you will find a beautifully crafted wardrobe/dressing room with many custom built-ins, lighting and mirrors. This lovely area conveniently leads to an exercise room, powder room and an oversized cedar closet, and this completes the third floor. There are four additional family bedrooms on the second floor, two share a Jack and Jill bathroom, one has its own en-suite, and the fifth bedroom suite offers versatile living space. The fifth bedroom and sitting room, located near the back stairs, welcomes an in-law arrangement, live in nanny, or out of town guests. The full basement offers at least another 2444 square feet of living space and includes a large recreation room with fireplace, billiard room, wet bar, spacious laundry room, large cedar closet, another storage room with built-in shelving, and a powder room. The yard is professionally landscaped, private, and nearly two acres is quite hard to come by in Winnetka. Additional features of this remarkable residence include: a three car, heated, attached garage, magnificent craftsmanship, glorious room sizes, four fireplaces, a slate roof, copper gutters, circular driveway and uncommon privacy. This residence is a true gem in the heart of Winnetka. Live a life of luxury and sophistication in this exceptional home. Woodley Road, with its canopy of mature trees, is a coveted private oasis, and yet is conveniently located near town, train, restaurants, schools and a public golf course. This property is not located in the flood plane.