Winnetka IL Real Estate & Homes for Sale

Welcome to Sherwood Forest living at its finest. Tucked within one of Northfield's most picturesque communities, this sun-filled 3-bedroom, 2-bath townhome lives like a single-family home featuring vaulted ceilings and oversized windows fill the spacious living room with natural light, while the large eat-in kitchen offers abundant cabinetry, generous prep space, and seamless access to the patio and garden beyond; with a rare feature few residences here can offer-a private, dedicated backyard surrounded by mature trees and lush landscaping. The flexible floor plan includes a main-level bedroom and full bath, two spacious upstairs bedrooms, hardwood floors, excellent storage, and a full basement with laundry and room for recreation, hobbies, or future expansion. Two dedicated parking spaces add everyday convenience. Enjoy a peaceful setting with beautifully maintained grounds, award-winning schools, and easy access to shopping, dining, and transportation-all in a highly sought-after Northfield location.

This is the opportunity buyers wait for. An architecturally significant Hubbard Woods Georgian that could never be duplicated today for anywhere near this cost. Perfectly positioned on one of the neighborhood's most coveted cul-de-sac streets, this distinctive home showcases extraordinary vintage details paired with over $1.2 million in thoughtful renovations and infrastructure improvements. Step inside and right away feel the elegant original details with original black & white marble floors, leaded glass windows and doors, gorgeous plaster dining room ceiling, interior arched doors, and rich architectural beams. The gracious first floor offers seamless circular flow, featuring a stately step-down living room/great room with a French mantel fireplace and curved leaded bay windows overlooking the professionally landscaped front yard. Oversized dining room, ideal for entertaining, showcases arched French doors and a Benjamin Marshall-inspired cove-molded ceiling and Philip Jefferies wallpaper. Just completed, a beautifully subtle off-white Chef's kitchen highlighted by creamy-hued Ann Sacks glazed subway tile, Wolf stove accented by Ikat inlay marble backsplash & 2 sinks. Brand new breakfast room space with custom glass built-ins leads to new oversized mudroom with artistic tiled flooring striking the perfect balance of fun. Office with FP & original mosaic tile restores character. Stoic staircase with original wrought iron handrails leads to 3 spacious bedrooms centered around a gracious reception hallway with a continued staircase to the 3rd floor. Tailored primary suite with custom window treatments in Kravet fabric ties into the renovated classic marble spa bath. Two new en-suite baths for both of the other beds and an attic space plumbed and ready for another bed/playroom. Just completed in June 2026, a dug-out lower-level rec space with exceptional ceiling height and 4th bedroom and marble bath. Beyond the beautiful finishes, this home has been comprehensively upgraded with a new architectural shingle roof, all-new copper gutters and downspouts, a fully underpinned foundation with deep-dig basement, new Marvin oversized basement windows, new sewer line, upgraded electrical service with underground power, new water service, new boiler, EV charger, and extensive renovations throughout both the first and second floors. If new construction is not your thing...then get ready to be taken back to the beautiful world of character & charm with all the new must-have upgrades of today's living. This was a labor of love rehab that got short due to a relo situation, so stomp on this one to be the first owner to enjoy the completed regal renovation. Steps to Hubbard Woods Elementary, 8 min walk to train and all the boutique stores & restaurants in Hubbard Woods...so convenient & divine living!

Incredible opportunity on desirable private Dorina Drive in Northfield's award-winning New Trier school district! Breathtaking, newly reimagined mansion on nearly 1 acre lot, with 7800 square feet of living space, plus 3500 square foot unfinished basement. Rare find in this prestigious Northshore neighborhood, private cul-de-sac street surrounded by multi-million dollar estates. Old world charm loaded with luxurious modern amenities. 5-car garage, accessed by secluded separate motor-court. Circular main drive leads to elegant limestone entrance portico, through the double-doors to the regal foyer with grand circular staircase. Living room and family room, each w/ fireplace. Throughout the home, refined wood paneling and accents. Huge main level primary suite w/ additional fireplace, sitting area, stunning bath with oversized shower and elegant soaking tub and private toilet room, and a giant walk-in closet. One-of-a-kind kitchen has been enlarged with double islands and the highest standard of cabinetry, features, and appliances (Wolf/SubZero/Cove). Stately office suite w/privacy room (or additional bedroom). Upstairs sitting area with fireplace leads to 4 large bedrooms, 2 of which are ensuite. Tall ceilings and hardwood floors, large laundry room, ample storage with 20+ closets, an abundance of natural light through 45 French doors and windows and multiple skylights, 4 HVAC zones with all new units...too many features to mention. To top it off...a huge, separate entrance, guest suite with another full eat-in kitchen, living room, bedroom and full bathroom! Perfect for multi-generational living, long-term guests, or rental income. CALL TONY FOR PRIVATE SHOWING.

The quintessential white-painted Colonial always makes a timeless statement-but set on one of East Winnetka's most spectacular blocks, just steps from town, train, beach and Village Green, it becomes truly exceptional. Welcoming in all the most beautiful ways, this designer showcase house is the one you look forward to coming home to this summer. After hitting the beach, be home in 5 min to get the outdoor kitchen in motion while preparing for s'mores over the fire pit & nightcap cocktails while conversations continue from the screened-in porch. Comforting the second you open the Farrow & Ball blue-painted door, you step inside to a traditional floor plan that all makes sense without missing a thing. The elegant foyer with cascading staircase floods the home with natural light as you step down to the elegantly appointed living room wrapped in a warm, rich blue/green hue with FP. Soothing dining room toned in a muted blush cream accented by a Ralph Lauren fixture opens to Carrara marble butler's pantry. Classic Chef's kitchen outfitted in white custom cabinetry, honed soapstone c-tops, & white subway tile overlooks manicured backyard reimagined by Midwest Arbor. Cozy breakfast room with command center, large mudroom with 2nd powder rm ideal for kid drop zone. Fab family room with beautiful bay window highlights the lush outdoors, and best of all is the attached screened-in porch for seamless indoor-to-outdoor living. 2nd floor has all been beautifully redone, starting with a luxe primary suite with customized walk-in closet & sleek stone bath. All nicely sized bedrooms, two beds sharing a marble jack-and-jill bath and 4th bed with en-suite bath. LL with movie area, 5th bed now serving as an office and huge storage room that can be reimagined as a workout room in a snap. It's all here as this special home is the pinnacle of North Shore living with a picture-perfect curb appeal that makes it a home run...and yes, a 5 min walk to Hometown too!

Move right into this impeccably updated and professionally decorated three-bedroom, two-and-a-half-bath residence offering sophisticated design and effortless living. The first floor showcases rich hardwood flooring and a stunning custom kitchen by DiGiulio Kitchen Design, thoughtfully designed for both everyday living and entertaining. Blonde wood cabinetry is beautifully paired with DiGiulio's signature white cabinetry, granite countertops, and top-of-the-line stainless steel appliances, including a Wolf double oven, five-burner cooktop, Bosch dishwasher, and Sub-Zero refrigerator. The kitchen opens seamlessly to a sun-drenched living room with a gas fireplace, creating a warm and inviting gathering space. As a highly sought-after corner unit, this home is filled with exceptional natural light, enhanced by expansive privacy windows throughout the dining room, kitchen, and living room. Sliding glass doors lead to an expansive west-facing L-shaped patio overlooking a tranquil pond with fountains and swans. Partially enclosed by brick walls and surrounded by mature landscaping, this private outdoor retreat serves as a true extension of the home. With the doors open, the soothing sound of the fountains in the pond and the beautiful swans swimming creates a utopic indoor-outdoor living experience. A separate dining room offers the perfect setting for formal entertaining. Upstairs, the second floor features three generously sized bedrooms, including a luxurious primary suite overlooking the pond and fountains with west facing sunsets. The suite includes custom California Closets and a beautifully appointed bath with double vanities, granite countertops, a walk-in shower, and the added convenience of an in-suite stacked washer and dryer. The front bedroom also features California Closets, a custom wall of built-in shelving and storage, and acoustic paneling, making it ideal as a bedroom, office, or creative space. The finished lower level provides flexible space for a home office, fitness area, or recreation room, and offers direct access to the garage and convenient covered parking with many built-in shelves for storage. This exceptional home combines luxury finishes, abundant natural light, and picturesque pond views in one of the community's most desirable Meadowlake corner locations.

PRISTINE TWO BEDROOM/TWO BATH CONDO IN DESIRABLE NORTHFIELD SQUARE. RECENT REHAB WITH AMPLE SPACE. BEAUTIFUL KITCHEN WITH WHITE QUARTZ COUNTERTOPS, GE FULL APPLIANCE PACKAGE IN SLATE FINISH, WHITE KITCHEN CABINETS, NEW NEUTRAL FLOORING, CUSTOM CLOSETS, RECESSED LIGHTING THROUGH-OUT, NEW ELECTRIC PANEL. LARGE SUN-FILLED BEDROOMS WITH FULL BATHS. FIRST FLOOR CONVENIENCE WITH TWO LOVELY PATIO AREAS FRONT AND BACK. STEPS AWAY FROM NEWLY REDONE POOL AND DEDICATED GARAGE SPACE. PAID SPECIAL ASSESSMENT INCLUDES NEW STAIRS, RAILINGS AND SHINGLES. THIS TRULY IS MOVE-IN READY AND WILL NOT LAST.

If you've been looking for room to spread out and don't want to sacrifice quality for quantity, this stately brick Colonial home is the answer. Blending timeless architecture with the layout families want today, this home has over 10,000 square feet and is set on 1.16 beautifully landscaped acres. Better than new, it was built with exceptional craftsmanship that is difficult to replicate today. Offering expansive rooms, tall ceilings, and abundant natural light throughout, it feels both grand and comfortable at the same time. Its classic curb appeal makes a lasting impression with a graceful arched front entry welcoming you inside. Upon entering, the stunning grand staircase sets the tone for the elegant yet inviting interiors. Your guests will be ushered from the dramatic foyer to the living room overlooking the back patio, and the dining room ideal for hosting large dinner parties. The layout naturally transitions from entertaining rooms to everyday living spaces, which revolve around the oversized kitchen with its expansive eat-in breakfast room. Directly off of the kitchen is the spacious family room with a vaulted game table area with wet bar, perfect for mahjong or poker nights. The well-appointed mudroom and laundry room help keep life organized and lead to the attached 3-car garage with 2 EV chargers. A gracious 1st floor guest suite and private home office are tucked away from the action at the other end of the home, providing quiet spaces to work and find respite. The grand staircase leads you upstairs to the primary suite with a massive walk-in closet and spa-like bath. Additionally, there are 3 bedrooms with ensuite bathrooms, and a 2nd-floor playroom-an increasingly sought-after feature that offers the perfect space for toys, homework, gaming, crafts, or a quiet retreat separate from the main living areas. The finished lower level has an enormous rec room, a home gym with a dug-out floor and full bath, a large wine cellar, and seemingly endless storage space. Outside, the private setting offers exceptional space to relax, entertain, and enjoy the beauty of the surrounding landscape, while being tucked away on one Northfield's most coveted private lanes. Located close to the award-winning elementary schools and famed Clarkson Park, you'll soon be embraced by one of the North Shore's most sought-after communities when making your home here.

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.

Beautifully updated all-brick ranch with a full, partially finished basement in the highly desirable Riverside neighborhood. This exceptional property backs to the scenic Middle Fork of the Chicago River, offering a private, beautifully landscaped backyard with a raised elevation and no flood insurance required. Located in the award-winning New Trier School District. This home is located within walking distance to Clarkson Park and just 20 miles from downtown Chicago. Extensively renovated in 2019. Featuring a new roof with added attic insulation, refinished hardwood floors throughout, a stunning kitchen with quartz countertops, a center island, and stainless steel appliances. The spacious family room addition was fully renovated and offers a dramatic 30-foot beamed ceiling, gas-start fireplace, abundant natural light, and sliding glass doors leading to the backyard patio-perfect for entertaining and everyday living. Additional updates include new bathroom vanities and a new sump pump with battery backup.Outstanding location, and a rare riverfront setting. Low property taxes! Please do not solicit and do not disturb occupants. Thank you very much.

Beautifully restored idyllic Victorian home expanded for today's living features a flexible floorplan with easy flow, generously sized rooms, dramatic ceiling heights, detailed millwork and plaster moldings, inlaid floors and an abundance of tall oversized windows. The lushly landscaped property highlighted by majestic oak trees is ideally located on a favorite east Winnetka street near lakefront beaches, shopping, restaurants, Metra, Greeley and New Trier East. The quintessential front porch welcomes you to sit and enjoy the view of the park-like lawn. The front entry opens to the foyer connecting the first floor rooms and a striking staircase. Grandly scaled great room sets the tone for the rest of the home, and offers a wonderful space for gathering and relaxing. The formal living and dining rooms echo the same gracious, comfortable style. An updated white kitchen with granite countertops has top appliances and opens to the family room with doors to the deck and paver patio. Second floor includes a stunning primary suite featuring a gorgeous bedroom filled with light, soaring ceilings, two walk-in closets, a luxurious spa bath and a lofted office above. Three additional bedrooms and two renovated baths complete this level. The third floor has treetop views, a bedroom, office and full bath. The lower level features a laundry room, playroom and storage. Very private back yard with two level deck and separate paver patio. Attached heated garage. Property sold "As- Is".

Regent Wood homes rarely come to market, and once you see this one, you'll understand why buyers wait years for a chance like this. As the largest home in this maintenance free subdivision at just over 5,100 total square feet, and the only one with a 3 car attached garage, 22 Regent Wood Rd stands apart even within a community known for quality. Tucked at the back of a peaceful cul-de-sac and wrapped in wooded privacy, the setting sets the tone before you even step inside, especially in the sunroom, a glass roofed, atrium style retreat with slate tile underfoot and windows on nearly every side framing mature trees and glimpses of the pond and its lily pads beyond. The living room makes its own impression, with soaring vaulted ceilings, a statement crystal chandelier, and a classic fireplace flanked by arched, transom topped doorways, with the sunroom opening off one side and black and white checkerboard tile carrying through the space on the other, giving the home real personality from the moment you walk in. The kitchen was built for function first, with glossy white cabinetry curving around a black granite topped island and perimeter counters, a built in double wall oven, and a sunny window over the sink looking straight into the trees. The first floor primary suite offers true single level convenience with a walk in closet and full en suite bath, while the private office just off the foyer pairs a bay window over the front grounds with a full wall of custom cherry wood built ins, ideal for a serious home library, office, or both. Upstairs, a loft style hallway open to the floor below leads to two generously sized bedrooms, each with its own full bathroom and walk in closet, a smart and private layout for family or guests, with playful dutch doors along the way that open from both the top and bottom. The fully finished basement nearly doubles the home's living space, anchored by a large recreation room and flanked by an exercise room, a second office, and a full wet bar built for hosting, along with a full bathroom featuring a steam shower and two separate storage rooms. This home has been genuinely cared for, not just maintained, and it's ready for its next owners to make it their own, offering low maintenance living without compromising on space, character, or privacy, whether that means more time in the sunroom watching the pond or hosting friends at the basement bar instead of running errands on a Saturday. Northfield's location adds to the appeal, with easy access to top rated schools, Metra service into the city, shopping, dining, and the North Shore lifestyle that draws people to this pocket of Chicagoland. Homes like this in Regent Wood simply do not come around, and this is a rare chance to own the largest, most distinctive home in the community, quietly tucked away and truly ready for its next chapter.

This 4-Bedrm and 2-Bath Cottage style home sits on a 5,267 Sq Ft lot in coveted Winnetka Hubbard Woods. This property located in top -rated schools (Hubbard Elementary) presents potential to renovate, expand or reimagine in a premier North Shore setting. The main floor plan unveils an open concept with a sprawling Family room filled with natural light next to separate sitting room with a gorgeous brick fireplace and hinged French doors to a formal Dining Room. A generous size kitchen finished with 36" cabinetry with glass facade accents, stainless steel appliances. Two good size bedrooms with a shared full bathroom between and a room as a separate office. Hardwood floors throughout. The second floor has 2 bedrooms and a loft. Full unfinished lower level with a half bathroom. Private fenced in yard and plenty of parking. Close to Metra, downtown Winnetka, Lake Michigan, parks, trails, shopping and MORE *** Sellers motivated.

Incredible opportunity to develop, customize, or thoughtfully renovate this traditional four-bedroom home situated on a picturesque half-acre lot backing directly to the Winnetka Golf Club on a quiet, tree-lined street. Whether you're envisioning a stunning custom new construction or transforming the existing residence into your dream home, this exceptional property offers endless possibilities in one of Winnetka's most desirable locations. The existing home features nearly 2,900 square feet of living space, an attached two-car garage, two main-level bedrooms, generous living and entertaining areas, and a partially finished basement with high ceilings that provides excellent expansion potential. Large windows throughout the home frame beautiful views of the golf course and fill the interior with natural light. The expansive backyard offers a rare combination of privacy, open green space, and breathtaking golf course settings, creating an ideal setting for outdoor entertaining or a future custom residence. All of this is just moments from award-winning schools, parks, downtown Winnetka, Metra, shopping, dining, and the lakefront. A truly rare opportunity to secure a premier half-acre homesite and bring your vision to life.

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!

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!

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.

Set on approximately 2.5 breathtaking private acres in one of Northfield's most coveted locations, 2311 Burr Oak presents a once-in-a-lifetime opportunity to own one of the North Shore's most remarkable private 5 bedroom, 4.2 bath estates. This timeless five-bedroom, four-full and two-half-bath residence seamlessly blends classic architectural elegance with graciously scaled living spaces designed for both everyday comfort and grand entertaining. Rich in character, the home features beautifully appointed formal living and dining rooms, exceptional millwork, multiple fireplaces, a dramatic vaulted-ceiling family room, an expansive primary suite, and an incredible temperature-controlled wine cellar. Every room reflects thoughtful craftsmanship and offers seamless views of the spectacular grounds. The estate's resort-inspired setting is truly unparalleled. The professionally landscaped grounds offer complete privacy and include a sparkling swimming pool with spa, a fully appointed pool house with a kitchen, laundry, full bath, and separate sleeping quarters, tennis and pickleball courts, a picturesque koi pond with zen waterfall and bridge, expansive rolling lawns, mature trees, and an attached six-car garage. Every detail has been thoughtfully designed to create an extraordinary lifestyle where recreation, relaxation, and elegant entertaining exist in perfect harmony. The combination of approximately 2.5 private acres, decades of meticulously cultivated landscaping, and an unmatched collection of amenities makes 2311 Burr Oak an irreplaceable offering. More than a residence, it is one of the North Shore's most iconic private estates-a legacy property to be enjoyed by all!

If you've been searching for RANCH-LIKE LIVING with a BREATHTAKING BACKYARD, this is it! Located in desirable Northfield where you get more space to spread out, this timeless Colonial home is on 1.1 acres of land with a serene backyard nestled beneath a canopy of towering oak trees. A long drive leads to an expansive parking court allowing guests to park with ease. Upon entering, you'll notice the dramatic floor-to-ceiling windows filling the home with natural light, and the charming moldings and millwork which create a comfortable atmosphere. The impressive foyer has sweeping backyard views, and overlooks the private brick patio - an idyllic setting for your morning coffee or entertaining on warm summer evenings. You'll want to host holiday gatherings in the elegant living room with a wood-burning fireplace and sun-filled bay window, and celebrate your special occasion dinners in the spacious dining room. Unwind with family in the inviting family room, or up the ante at the game table. For everyday living, the handsome wood-paneled study with a roaring fireplace is an ideal home office or library/den. The eat-in kitchen with plenty of pantry storage is adjacent to the laundry/mudroom, as well as the powder room. The attached two-car garage has deep built-in shelving to store everything you need, extra shelving along the side, and you can still park your two SUVs inside! The highly sought-after 1st-floor primary suite offers the ease and comfort of single-level living, while 2 extra-large upstairs bedrooms with spacious walk-in closets and a shared full bath provide comfortable accommodations for family and guests. Ideally located near Blue Ribbon Award-winning Sunset Ridge School, parks, shopping, dining, and transportation, this exceptional home offers the serenity of estate-style living with every convenience just moments away. Agent owned.

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.

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!

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!!!

An extraordinary "boutique hotel" living experience, impeccably situated in the heart of Winnetka. Beyond a stately solid-iron gate adorned with gold medallion accents lies a private sanctuary just 18 miles from Chicago and less than half a mile from the sandy shores of Lake Michigan. Evoking the glamour and grandeur of a Roaring Twenties estate, this remarkable residence channels the elegance of The Great Gatsby era with five-star refinement at every turn. A dramatic foyer welcomes you with gleaming marble floors and a sweeping bridal staircase crowned by intricate wrought-iron railings, all illuminated by a stunning domed Art Deco skylight overhead. The main level unfolds with gracious formal rooms designed for both grand entertaining and effortless flow. An elegantly appointed dining room transitions seamlessly into a spectacular chef's kitchen, where a striking black-and-white palette of stone and texture creates a timeless aesthetic. Top-tier appliances-including a side-by-side Sub-Zero glass-door refrigerator and freezer-complement a bespoke upholstered dining banquette, offering a restaurant-caliber culinary experience at home. Thoughtfully designed corridors and private retreats provide space for both gathering and solitude. A finely finished office of magazine-worthy distinction, a warm and inviting family room with an 80-inch television and custom lacquered walls, a first-floor laundry room, guest suite with full bath, and a fully equipped mudroom enhance everyday living. The heated four-car garage wing is a masterpiece in itself, featuring epoxy floors, custom cabinetry, and stone countertops-an exceptional showcase for the discerning automotive collector. Upstairs, an expansive second level hosts a primary suite truly fit for royalty. A serene sitting room with a fireplace precedes a breathtaking onyx bath with dual custom vanities and a commercial-grade steam shower complete with body sprays and a rain head. Bathed in natural light, the craftsmanship and stonework must be experienced to be fully appreciated. Four additional bedrooms, each with pristine white-stone en-suite baths, provide luxurious accommodations for family and guests. An exercise studio with a dedicated yoga retreat, adorned in palm-inspired wall coverings, offers a tranquil escape for wellness and balance. The fully finished lower level features a kitchenette, bath, wine room, and expansive entertainment spaces designed for comfort and leisure. Outdoors, enchanting terraces, sun-drenched patios, and winding pathways create a private oasis ideal for alfresco dining and elegant gatherings. Meticulously renovated with no expense spared and exquisitely furnished to celebrate its Art Deco heritage, this residence offers a rare opportunity that feels more akin to a world-class luxury hotel than a private home.

It is exceptionally rare to find a privately set masterpiece with sweeping views of the Winnetka Golf Course that also offers the opportunity to step directly into a freshly completed 2025/2026 designer showcase renovation. Nestled on a beautifully landscaped half-acre site overlooking the golf course, this extraordinary stone residence has been impeccably transformed through a comprehensive renovation marrying timeless architecture with sophisticated design. With coveted western exposure and surrounding lush grounds, the home captures spectacular sunset skies across the golf course from most rooms in the home. Thoughtfully curated throughout, the 6 bed, 9 bath home showcases exceptional craftsmanship with a diamond leaded glass front door, custom millwork, designer lighting, 5 fireplaces, and a refined mix of marble, porcelain, and rich wood flooring. Smart home enhancements include Lutron lighting and integrated Sonos access points throughout much of the home. Ring security and exterior cameras have been integrated to provide both convenience and peace of mind. The stunning chef's kitchen was designed with both beauty and functionality in mind, featuring Taj Mahal honed quartzite countertops with elegant ogee edging, custom cabinetry, Perrin & Rowe fixtures, Franke sink, Sub-Zero refrigeration, Thermador appliances including a 6-burner range with grill, both Bosch and Fisher & Paykel dishwashers, warming drawer, walk-in pantry, and dual butler's pantries. The adjacent breakfast area opens beautifully to the outdoor entertaining spaces and picturesque golf course setting beyond. The primary suite, with a spacious private terrace overlooking the golf course, was designed with a quiet, hotel-inspired feel, featuring Calcutta Gold marble heated floors and shower, Victoria + Albert freestanding soaking tub, custom built-ins, iceberg polished quartzite surfaces, and elevated designer finishes throughout. All guest suites are en-suite with ample custom closets and continue the home's sophisticated aesthetic with premium quartzite countertops and Perrin & Rowe or Rohl Lombardia fixtures in the bathrooms. Designed for exceptional entertaining and lifestyle living, the expansive lower level includes a theater room, recreation space, workout/wellness room, sauna, wet bar, expansive wine cellar, guest suite, secondary kitchen, and extensive storage. Outdoors, professionally designed gardens provide exceptional entertaining areas including gas grill area with fire pit. The fully fenced and sprinklered yard creates a remarkably private setting with sweeping golf course views. Additional highlights include a slate roof, newer mechanical systems, dual sump pumps with triple redundancy, whole-house water filtration, generator backup, 3-car attached heated garage with additional overflow parking, and an advanced security system. Conveniently located near schools, AC Nielsen Tennis Center, Skokie Playfields and the Winnetka Ice Arena while positioned along one of the North Shore's sought-after golf locations.

A true crown jewel in Northfield filled with possibilities! This 2.4-acre property is at the end of one of the Village's most prestigious lanes, affording you all the privacy you could desire coupled with the convenience of being close to Blue Ribbon award-winning schools and downtown Northfield. The elegant red brick manor home has opportunity written all over it. Enter into the slate-floored foyer with lovely curving staircase, which flows into the grand living room with beautiful french doors facing south, sunlight streaming in. A private office is perfectly situated off of the corner of the living room, ideal for working from home. An oversized dining room adjoining the kitchen with eat-in table could be reimagined by extending the kitchen into the dining room, it would be a game changer! A large family room and amazing solarium overlooking the backyard and patio, and a mudroom leading to the 2.1-car attached garage with b completes the first floor. The 2nd floor features the primary suite, 2 large bedrooms with a jack-and-jill bath, 2 smaller bedrooms with a shared bath, and the laundry. Ask the list agent for transformation ideas! An unfinished basement and full-height attic offer additional potential. The parcel itself features soaring, mature oak trees, a cut through to Middlefork circle opening up a streamlined pathway to Middlefork Tennis Club, and is situated a stone's throw from Sunset Ridge Country Club. With a little imagination, this home could be totally transformed into the forever home of your DREAMS. Home is being sold AS IS.

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.