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$1,100,000
4 Beds ⋅ 2 Baths ⋅ 12746221 MLS ⋅ NEW Status
Charming House in Winnetka with Timeless Appeal Welcome to this charming four-bedroom, 1 1/2 bath Winnetka home that beautifully blends classic character with comfortable, inviting living spaces. Warm and welcoming from the moment you walk past the stately over four-hundred-year-old Burr Oak in the front yard, this home offers a wonderful combination of livability and an in-town location. Thoughtfully maintained and filled with old-world craftsmanship, the entire home has a comfortable flow for everyday living with custom details throughout with features such as wood moldings, built-in bookshelves, and hardwood floors. The first floor includes spacious living and dining rooms and a lovely sunroom/den with windows on three sides. The second floor features a generous sitting room/office with beautiful 180-degree views of the property. The peaceful, private rear yard has a gracious stone patio. A commercial Life Safety System protects the entire home and alerts local authorities in case of fire, smoke, or carbon monoxide danger. The current owner has lived there for fifty-one years and has never had water in the basement. The location of this home is unique, situated in a desirable Winnetka neighborhood within easy walking distance of schools and parks, and three blocks to the train, shopping, dining -and all this wonderful community has to offer. This is a truly lovely home that offers a special opportunity to enjoy the charm and convenience of Winnetka in a setting that is easy to love.

592 Provident Avenue, Winnetka
$4,500,000
5 Beds ⋅ 9 Baths ⋅ 12753203 MLS ⋅ NEW Status
Phenomenal value as this finely built newer construction home privately set with serene panoramic Winnetka Golf Club vistas just hit "elevated luxury" status with an impeccable 2026 no expense spared rehab. Starting off with the new stunning Chef's kitchen that radiates with extra-thick Taj Mahal honed quartzite c-tops, Perrin & Rowe fixtures, Frankie sink, Visual Comfort brushed brass pendants & handcrafted new custom cabinets painted in Farrow & Ball Au Lait. ABT professional-grade S/S appliance package includes Sub-Zero, Bosch, Thermador, Fisher & Paykel with 2 butler's pantries & walk-in pantry. The rest of this 8500 sq. ft. all-stone-built beauty is loaded with the highest standard of designer upgrades, making it turnkey ready! With over 10-foot ceilings creating huge volume with soaring natural light, the dramatic double atrium entry with cascading bridal is the first grand impression. Step into beautifully scaled entertaining spaces with freshly stained, pristine hardwood floors accented with crisp painted white walls, creating a light and welcoming vibe. Living to dining to great room, all with new low-voltage Lutron lighting and Urban Electric fixtures, showcase grand open entertaining, while the cozy custom wood-paneled walnut office is the perfect hideout retreat with its own private patio. Both 1st floor powder rooms are now outfitted in Villa Blanca marble with custom fluted vanities, Phillip Jeffries linen wallpapers & Ann Sacks tiling. Second floor hits a new note with brand new primary "boutique hotel" suite with gorgeous Gold Calcutta marble heated floors, Iceberg quartzite c-tops, Victoria & Albert free-standing soaking tub, oversized shower w/rain heads and separate vanity areas. 4 additional bedrooms all with en-suite freshened Rohl and Villa Blanca marble baths, customized closets and white plantation shutters. Loaded lower level with high ceilings as it all from the sauna, guest suite, handsome wine room, large theater, billiards area with custom granite bar area/second kitchen, exercise wellness room, and storage. Then there are all the extras: slate roof, newer mechanicals, 3-car heated garage, water filtration & backup generator, huge mudroom, dual staircases & incredible bluestone tiered viewing patios with built-out BBQ area finish off this private sanctuary. It's all here, so get ready to roll this holiday season in this new rehab with transitional sparkle!

1380 Westmoor Trail, Winnetka
$2,000,000
4 Beds ⋅ 5 Baths ⋅ 12751307 MLS ⋅ NEW Status
A rare expression of extraordinary North Shore living, this quintessential red-brick Colonial sits on a 100' x 175' double lot (.39 of an acre) on coveted Hill Terrace, one of Winnetka's prettiest private lanes, in an A+ walk-to-everything location. Designed by prolific architect Bertram A. Weber, this much-loved residence has been completely reimagined by its current owners, who've seamlessly married classic architecture with sophisticated, thoughtful updates (new Visual Comfort and Restoration Hardware lighting fixtures, new hardwood floors, new recessed lighting, new Emtek door hardware, new Sonos system, and new Graber custom window treatments, to name a few). A welcoming foyer with rich architectural moldings leads to the light-filled living room with gas fireplace and adjacent formal dining room. Cook's kitchen has Calacatta marble countertops, Sub-Zero paneled fridge and upgraded stainless steel appliances. The spacious family room boasts a wall of built-ins, two walls of windows, and a wet bar with GE Cafe refrigerator. Modernized attached screened porch and mudroom overlook the lush, professionally landscaped backyard with multiple patios, new oversized composite deck, newly expanded paver patio and walkway, new cedar fence, and vegetable garden with raised beds. A home office with a view and updated powder room complete the first floor. Upstairs, the serene primary suite has a walk-in and two additional closets leading to an oversized bath with cathedral ceilings, Jacuzzi tub, shower, and dual vanities. At the other end of the floor, the most incredible junior suite offers the versatility of a second primary, complete with walk-in closet, remodeled bath with dual vanities, and a private back staircase to the family room below. Two more bedrooms share a new RH hall bath. The finished lower level has a recreation room, exercise area, new bedroom, laundry room with new LG washer and dryer, full bath (expanded from half) and private entrance with ADT Bluetooth lock. The detached two-plus-car garage includes a dedicated shed/storage area and walk-up attic. Dual-zone heating and air conditioning, irrigation system and new exterior lighting. With just eight residences, Hill Terrace has a hidden-away, private cul-de-sac like setting, yet it's steps from the Green Bay Trail, top-rated schools (New Trier, Greeley Elementary, Faith, Hope and Charity, and North Shore Country Day all less than half a mile away), parks, lake, town and train, making 579 a True Treasure in the Heart of Winnetka!

579 Hill Terrace, Winnetka
$2,695,000
4 Beds ⋅ 5 Baths ⋅ 12715045 MLS ⋅ ACTIVE Status
A rare, fully renovated and updated home offering move-in-ready luxury and thoughtful craftsmanship throughout. The primary bath was renovated down to the studs, and now offers a generous shower, private water closet, and all-new fixtures, plumbing, and lighting, plus a huge closet/dressing room with a 7-foot quartz-topped built-in with 24 custom drawers, and floor to ceiling custom built-ins. Two bedrooms were combined into a spacious home office (larger than the primary) with hardwood floors, updated lighting, custom closet built-ins, and upgraded networking. The first-floor office was reimagined as a dramatic library, with custom maple built-ins, matching ceiling moldings, a window seat, and high-gloss lacquered finishes. The home is wired throughout for CAT6 and wifi, with home theater wiring, an upgraded security system, energy-efficient attic insulation, and improved HVAC routing - smart, efficient, and move-in ready. Owner is a Licensed Real Estate Broker.

1140 Oakley Avenue, Winnetka
$4,200,000
5 Beds ⋅ 9 Baths ⋅ 12701871 MLS ⋅ ACTIVE Status
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!

1128 Mt. Pleasant Road, Winnetka
$2,795,000
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
$4,949,000
5 Beds ⋅ 7 Baths ⋅ 12698685 MLS ⋅ ACTIVE Status
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.

320 Woodley Road, Winnetka
$2,785,000
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
$29,900,000
7 Beds ⋅ 13 Baths ⋅ 12680920 MLS ⋅ ACTIVE Status
It's time to unveil the pinnacle of lakefront living in IL, as this newer construction estate is better than brand new construction as it encompasses features that could never be built today with the new lakefront building ordinances. Try to top this...your personal wellness club that is only 20 steps out to your own private, 141-foot wide, sandy beach with indoor pool, sauna, and state-of-the-art gym, to outdoor entertainment space with built-in bluff terrace, 20x40 pool & spa with matching cabana, enclave fire pit, outdoor kitchen and grass tennis court. And the inside...first start from the very top by taking the elevator to the 3rd floor: where guests can have privacy in the in-law suite with a bar, studio, and private patio with panoramic lake views. Hit the 2nd floor with 5 more beds, laundry, and posh master suite with marble bath and jaw dropping lake views, 2 walk-in wardrobe rooms and massive bedroom with fireplace and private patio. Now for the main floor... a dramatic entry with cascading bridal staircase that was made famous with the hit show "Empire" will seem familiar as you step into the reception hallway with 15-foot soaring ceilings. Sun-drenched formal rooms with a stoic mahogany paneled office where deals get done as you step right out the French doors to the pool area. The great room is the perfect viewpoint to capture all the magnificent outdoor fun zones through the floor to ceiling windows with the blues of the lake in the distance. A kitchen that no real chef cannot fall in love with...double islands, endless counter space, all high-end appliances, even a built-in rice maker. The Solarium breakfast room allows for non-depressing meals even on a rainy day and a fabulous sun room with terraced patio for private conversations. Now down to the lower level as there is not one thing missing... theater room, wine room, bar, massive rec room for teenage parties and that secret tunnel to your own wellness wing. Of course, an attached 4-car garage, private gated entrance & motor court drive. No words can really bring this estate to life as only a private tour can bring this living experience to reality. No need to build... as this would cost over $55 million minimum to replicate. Your smartest lakefront investment is now available and even with lake front homes it's still about location, location, location. 319 Sheridan Rd. is the PRIME part of Sheridan Road where two other $30 million plus homes have just closed in the last year as these homes are not high in the bluffs but are in-town estates. Walk to Greeley & New Trier in 10 minutes, ride your bike to town in 5 minutes, jump on the train for a 29 minute ride to the city, and best yet...spend only 3 minutes pulling out your boat from the commercial level boathouse right into the gorgeous waters of Lake Michigan from your own private sandy beach! Private lakefront fun zone...enter at your own risk!

319 Sheridan Road, Winnetka
$2,250,000
4 Beds ⋅ 6 Baths ⋅ 12673083 MLS ⋅ ACTIVE Status
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!!!

42 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
$16,900,000
6 Beds ⋅ 10 Baths ⋅ 12600188 MLS ⋅ ACTIVE Status
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

915 Sunset Road, Winnetka



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