Quick Winnetka IL MLS Search

Browse All Winnetka IL Properties for Sale

$1,599,000
5 Beds 5 Baths 11871573 MLS NEW Status
A true classic East Winnetka home, steps to the Village Green. beaches, town, and train. Beautiful inside and out! Situated on a private wide lot (65') with lush landscaping and secluded outdoor spaces. Indoors, there are multiple casual and formal gathering spaces with hardwood floors throughout, gorgeous vintage millwork, and large, bright windows streaming with natural light. A gracious foyer welcomes you into the incredibly generous living room boasting a handsome stone fireplace, original etched glass windows, and a beautiful bay with verdant vistas along with the dining room area, accommodating any size gathering. A comfortable family room and bright sunroom with decorative fireplace overlook the gardens. They are conveniently located next to the renovated kitchen with top of the line appliances, granite countertops, a great center island, and abundant pantry space with panoramic views of the gardens. Step out of the kitchen to a fabulous deck, outdoor kitchen, lovely stone patio with a fire pit, and 2 car garage. Everyone's favorite spot to wile days away is the screened-in porch overlooking the lush backyard. The private primary is a storybook retreat with a wonderful newly updated bath and wood burning fireplace. Three additional bedrooms and refreshed hall bath complete the 2nd floor. The treetop suite on the third floor offers a large bedroom with skylights, bath, and loads of storage space. There is room for everyone with a great rec room with half bath and wet bar in the basement. Enjoy a wonderfully comfortable lifestyle in a most premiere East Winnetka location!

636 Cherry Street, Winnetka

$1,100,000
4 Beds 3 Baths 11882355 MLS CONTINGENT Status
Are you ready to turn your real estate dreams into reality? Look no further! Nestled on a serene and picturesque 75' x 165' lot, this property presents a unique opportunity for those with a vision. Situated on a tranquil winding street, you'll find yourself captivated by the charm of the surroundings and the promise of transformation. A rare location, this property is perfectly positioned just a stone's throw away from all the amenities you desire. Enjoy the convenience of being near shops, the train station, schools, parks, and the beach. Your lifestyle upgrade awaits! This spacious lot provides a canvas for your imagination to run wild. Imagine the possibilities - from a complete rehabilitation to designing and building your dream home from scratch. Whether you're an investor looking to maximize returns or a homeowner ready to customize your ideal living space, the potential of this property is unparalleled. Create a modern masterpiece that complements the neighborhood while reflecting your personal style. Despite its close proximity to bustling amenities, the property's location on a quiet winding street offers a peaceful and serene ambiance. Embrace the best of both worlds - a serene retreat that's also within reach of urban conveniences. With the right vision and execution, this property can become a significant investment opportunity. The growth potential in this coveted area ensures that any investment made will yield remarkable returns in the years to come. Whether you choose to rehab the existing structure or build anew, the possibilities are boundless. Seize the opportunity to shape your real estate dreams in a location that has it all.

636 Walden Road, Winnetka

$1,100,000
4 Beds 3 Baths 11873350 MLS CONTINGENT Status
Are you ready to turn your real estate dreams into reality? Look no further! Nestled on a serene and picturesque 75' x 165' lot, this property presents a unique opportunity for those with a vision. Situated on a tranquil winding street, you'll find yourself captivated by the charm of the surroundings and the promise of transformation. A rare location, this property is perfectly positioned just a stone's throw away from all the amenities you desire. Enjoy the convenience of being near shops, the train station, schools, parks, and the beach. Your lifestyle upgrade awaits! This spacious lot provides a canvas for your imagination to run wild. Imagine the possibilities - from a complete rehabilitation to designing and building your dream home from scratch. Whether you're an investor looking to maximize returns or a homeowner ready to customize your ideal living space, the potential of this property is unparalleled. Create a modern masterpiece that complements the neighborhood while reflecting your personal style. Despite its close proximity to bustling amenities, the property's location on a quiet winding street offers a peaceful and serene ambiance. Embrace the best of both worlds - a serene retreat that's also within reach of urban conveniences. With the right vision and execution, this property can become a significant investment opportunity. The growth potential in this coveted area ensures that any investment made will yield remarkable returns in the years to come. Whether you choose to rehab the existing structure or build anew, the possibilities are boundless. Seize the opportunity to shape your real estate dreams in a location that has it all.

636 Walden Road, Winnetka

$5,999,000
6 Beds 9 Baths 11870023 MLS ACTIVE Status
A remarkable opportunity awaits to acquire one of Winnetka's most sought-after properties. This extraordinary 5+BD/6.3BA Nantucket-inspired residence seamlessly combines coastal charm and comfortable luxurious living on a lush 1.3 acre landscape right in the heart of Winnetka. Constructed in 2013 as a collaborative vision of owner and designers, this exceptional abode is the epitome of timeless design. From its striking exterior to its meticulously curated interiors, every detail has been carefully orchestrated, promising a lifestyle of simple luxury to the most discerning buyer. A majestic driveway and captivating front porch welcome you with an air of coastal refinement. Step inside the grand foyer to be greeted by superb craftsmanship, a sweeping staircase, rich hardwood floors, impeccable millwork, and expansive floor-to-ceiling windows that set the stage for the ambiance that permeates throughout. The expansive open floor plan boasts soaring ceilings, effortlessly merging formal and informal spaces.The spacious central family room is an architectural marvel in design as it offers breathtaking outdoor views that evolve with the changing seasons and spans across to the sun room/living room bathed in natural light on the west side and to the kitchen then screened porch to the east. Perfect for entertaining, the generous dining room exudes a welcoming grandeur. A haven for culinary enthusiasts, the gourmet kitchen is a true masterpiece with top-of-the-line appliances, custom cabinetry, exquisite marble countertops and a walk-in pantry. The wet bar and expansive center island plus seating around the fireplace provide space for gathering while the captivating breakfast room in-the-round and screened porch with a wood-burning fireplace overlook the meticulously landscaped grounds.On the main level, a private guest suite alongside a beautifully wood-paneled library with a discreet door leading to the sunroom, and an expansive private office complete with a conference area. The potential for a primary wing on the first floor adds to the allure. Additional main level features include an impressive mudroom wing, a "command central" office and an attached heated 4-car garage.The primary suite is a sanctuary of serenity, featuring a private sitting area, its own outdoor balcony with a remotely controlled screened porch conversion, two walk-in dressing galleries and two spa-like bathrooms adorned with the finest marble and custom cabinetry finishes. Flexible private room can serve as an additional office, exercise room, or nursery. Four additional well-proportioned bedrooms, each meticulously designed for absolute comfort and privacy, offer luxurious en-suite bathrooms and custom walk-in closets amplifying the sense of casual luxury. The second-floor laundry suite with ample storage overlooks the lush grounds. The breathtaking third floor with its treetop views and natural light boasts an impressive 1900+ square feet of additional living space: rec room, exercise room, media room & more! Outdoor living seamlessly extends the home's allure, with expansive bluestone verandas overlooking the professionally manicured grounds that showcase lush gardens, mature trees and fragrant blossoms. These expansive grounds lead to a private oasis that exudes a resort-like experience, all within the confines of your own estate. In every aspect, this exceptional Nantucket-style home establishes a benchmark for luxurious living. With its awe-inspiring design, meticulous attention to detail, high end technology and a fusion of elegance and comfort, it delivers an unparalleled experience of refined living in a coveted locale. Prepare to embrace a lifestyle that surpasses all expectations, all within walking distance to town, train, Winnetka schools, and more.

931 Sunset Road, Winnetka

$1,599,000
5 Beds 4 Baths 11871177 MLS PENDING Status
Enjoy lake breezes and an amazing lifestyle in an immaculate 5 bedroom, 3.5 bathroom East Winnetka Hemphill gem on a coveted private lane steps to Elder beach, the train, and New Trier schools. Set on an extra wide lot (75'), this meticulously maintained and solidly built home gleams with natural light and boasts many updates harmonizing modern functionality with beauty and charm. Across the back of the house are incredible open vistas of the carefully curated backyard. The custom, gourmet kitchen boasting top-of-the-line appliances and finishes adjoins the comfortable family room overlooking the private verdant gardens. The living room with gorgeous millwork and a wood burning fireplace is the perfect space for both large gatherings and quiet contemplation. Adjacent is a wonderful dining room with french doors opening to the lushly landscaped backyard with pergola; a tranquil haven for relaxation and entertainment. The first floor also features a welcoming foyer and a mudroom situated next to the attached custom organized two car garage. The primary suite is a private oasis, complete with a spa-like ensuite bathroom and custom closet space. Enjoy fresh air, beautiful sunsets, and green views on the balcony. Three additional well-sized bedrooms on the 2nd floor, one with ensuite, two sharing a 'Jack and Jill' bathroom complete the second floor. With the remarkable 3rd-floor tree-top suite and the fabulous basement rec room plus loads of storage space, there are versatile spaces for everyone, whether it's an extra bedroom, a home gym, or a quiet home office. A fabulous home in an A+location!

150 Fuller Lane, Winnetka

$1,295,000
5 Beds 5 Baths 11874709 MLS ACTIVE Status
Nestled on a private cul-de-sac and surrounded by nearly an acre of manicured grounds, this timeless custom-built Hemphill home is an updated classic, inside and out. As you come up the private driveway, you will see that the home is set among mature trees and decorative plantings. The front of the property is especially lovely at night when landscaping and facade are custom lit. Walk around back for the spectacular setting: The large bluestone patio fronts a koi pond fed by a boulder scaped waterfall. Lush plantings, including Magnolia trees and Japanese maples, create an enclosed haven for parties, a simple BBQ, or just star gazing. The yard provides plenty of room for games, or perhaps adding that family pool. Inside, the large rooms have been professionally decorated and continually updated. The main floor perfectly flows for entertaining but practical and comfortable for everyday living. Hardwood oak flooring covers several rooms. Many other features include a marble entry, custom gourmet's kitchen with top-line and luxury appliances, utility and prep sinks, grill, and adjacent breakfast room opening onto the patio. Also enjoy wet bars in the family room and library. The light filled living room has a wood burning fireplace with a marble mantle & tumbled marble surround, custom display lighted shelving, and plantation shutters. The dining room has French doors and excellent storage for dinnerware and linens. There is a main floor bedroom with full bath adjoining. An exquisite powder room is convenient to all entertainment areas. The large family room with loads of storage also accesses the patio. The 2nd floor has a unique, recently renovated Primary suite: a private retreat boasting magnificent hardwood built-ins custom designed for both decor and function, a serene view, 2 separate marble and granite bathrooms, 2 walk-in closets and custom lighting. Three additional bedrooms-2 with walk in closets- a hallway bath with double vanity, and a walk-in linen closet complete the 2nd floor. All carpeted bedrooms have oak wood flooring beneath. The house sits midway between the Avoca District's award winning schools and is a short ride to New Trier High. PRIVACY, LUXURY, COMFORT AND CONVENIENCE; THIS HOME HAS IT ALL, INCLUDING A NEW ROOF! (This property is broker owned.)

24 Longmeadow Road, Winnetka

$4,950,000
5 Beds 8 Baths 11849043 MLS ACTIVE Status
Get ready to be taken into world of enchantment & beauty as this sole owner custom brick manor masterpiece transports you into the English countryside. Award winning collaboration of picturesque grounds & layered gardens by notable landscape architect Craig Bergmann led by the elegant vision of timeless design by Soucie Horner LTD Interiors. Set on over an half acre on coveted Kent Road, the stone gate entrance with graveled courtyard & permitter blue stone pathways highlight the beautiful peaks of slate roof, replicated lead glass arched windows, intricate brickwork w/copper downspouts & gutters & 12 ft custom front door create an authentic English vision. The mood is instantly felt as you step inside to the formal entry with custom wrought iron railed staircase accented with a Ralph Lauren oversized lantern with view of the step down great room. 14 foot soaring ceilings, custom glass display cabinets painted in an earth tone Farrow & Ball color flank the stately limestone FP, and floor to ceiling windows naturally flood translucent light with the natural highlight of gardens in the background. Ideally positioned, cozy office is nestled off the great room outfitted in handsome custom built-ins, cathedral peaked ceiling and Mahogany trimmed FP w/white veined black marble & even a private entrance to the outside. Sultry dining room overlooks great room with de Gournay wall coverings, Visual Comfort fixtures and custom walnut butler's pantry that leads you into the culinary haven. Custom Christopher Peacock kitchen blends the best in design with soapstone countertops, Ann Sacks tumbled limestone backspalsh, clay colored Farrow & Ball cabinets and Holly Hunt matching lanterns. Huge island with prep sink and separate breakfast space with command center and French doors that lead to one of the many dining patios. Separate courtyard patio off kitchen as well ideal for cocktails leads to a perfected manicured square lawn accented with pear trees & nightscape lighting that majestically sets the stage for any outside event or spots game. Step down to the cozy family room, reminiscent of a countryside retreat, boasts stunning walnut woodwork, grand fireplace & pairs of French doors that beautifully embrace the bluestone patios with the vibrant blooms of the garden - a harmonious blend of indoor & outdoor living with even the sounds of the fountain trickling in the background. First floor large private laundry & 2 mudroom areas with custom cabinetry leads to 2.5 car attached garage. 2nd level with 5 generously appointed bedrooms all ensuite, including the hotel level primary suite with a walk-in closet with window seat & its own powder room. Continuing into the suite, a graceful hall leads you to the bedroom, with walk in custom closets & the luxurious primary with a soaking tub, separate shower & dual vanities. Primary sitting room off the bedroom a perfect place to relax & unwind with fireplace. Explore to the other 4 additional bedrooms as they are all unique with their own luxurious white marble private bath. This very distinctive floor is full of character and ideal for those all wanting their own space. Entertaining galore can be found on the lower level, large rec room, movie theatre, exposed brick wine room (that can be fully customized), work out room, full bath with steam shower and separate storage room. This home is a destination of beauty & privacy and it would be impossible to replicate this level of fine detail & divine landscaping at this price. A true luxe inspired opportunity in a 5 star Winnetka location that even comes with a tow path for kids at the end of Kent through the "secret woods" to Hubbard Woods Elementary School. A true English fairytale indeed at 8 Kent Road !

8 Kent Road, Winnetka

$4,449,900
6 Beds 9 Baths 11837429 MLS ACTIVE Status
The largest property in coveted Crow Island school district with over 2.5 acres of the most spectacular rolling green lush grounds, 151 Meadow is truly a pinnacle opportunity to own the most significant in-town estate. Gloriously set on beautiful lane with a natural canopy of mature landscaping with a handful of exquisite homes, this classic Georgian home is ripe for someone who wants this exclusive opportunity to rehab as the bones & architectural details of this classic beauty cannot be replicated today. Use the existing scale of the graceful, southern 5 white pillar exterior with the elegance of the formal foyer entrance with classic Palladian window entry staircase to create your own 2023 luxurious version of this special home. This 6 bed/6.3 bath home encompasses an ideal floor plan as all the rooms are in the right spaces with large formal rooms & expansive kitchen that can bring to life so many optional designs. Huge 3rd floor that can be built out for fitness room /stuido or home office floor. Fine features are woven throughout: 6 FPs, arched doorways with beautifully cased opening, intricate mill work, custom built ins and just a timeless stoic vibe. Attached 3 car garage, greenhouse, sweeping bluestone terrace, 2 sets of staircases and picturesque pool in the rear of the property are are added value features. Incredible light shines throughout all rooms with panoramic views of the lush 2.6 acres that surround this property. If rehabbing is your veins... then there is no reason why you won't fall in love with this golden opportunity! This is the house that would make for an award winning renovation that would grace all social media as it is already so beautiful to begin with! Incredible location close to Crow Island, New Trier, NSCC, Loyola. Steps to Indian Hill train. This is a chance of a lifetime to be in Winnetka proper school district with the most glorious setting!

151 Meadow Lane, Winnetka

$4,695,000
5 Beds 7 Baths 11853694 MLS ACTIVE Status
Welcome to the #1 Prospect in East Winnetka! This new construction gem will be beautifully situated on a wide property (100x150) just 3 blocks to the beach, and 4 blocks to the finest restaurants in Winnetka. The proposed plans feature a board and batton and stone home with a welcoming front porch, that will fit perfectly into the neighborhood. Step inside to discover a flexible and open floor plan, thoughtfully designed to meet the needs of modern living. The heart of the home is a gourmet chef's kitchen that flows into the inviting family room and living room with double-sided fireplace and built-ins. Adjacent to the living areas, you'll find a sophisticated dining room and a custom-built library, complete with a cozy fireplace. Enhancing convenience, an expansive mudroom and a three-car attached garage provide ample storage and organization options. Ascend the light-filled staircase to the second floor, where four spacious bedrooms await. The crowning jewel is the primary suite, boasting his and her walk-in closets and a luxurious marble master bath with heated floors. The attic floor features a fifth bedroom suite that enjoys ample light. The lower level promises endless entertainment for the entire family. Discover an exercise room overlooking a deep sport court with soaring 17-foot ceilings, a media room for cinematic experiences, a wine room for connoisseurs, a basement bar for social gatherings, and a sixth bedroom for guests or extended family members. Outside, the expansive yard is your own private oasis with a covered porch and an exterior fireplace. Work with our team to customize this home to your to fit your unique lifestyle!

844 Prospect Avenue, Winnetka

$2,975,153
6 Beds 7 Baths 11852768 MLS ACTIVE Status
Step into this bright and airy modern farmhouse new construction in coveted Hubbard Woods, and call it home. Situated between Hubbard Woods and Winnetka Metra stations, this charming light-filled 7 bed 6.5 bath home is situated on Walden Road, a serene tree-lined street just a 5 minute walk to the heart of the village's commercial and social center. The house boasts every detail for comfortable modern living, from an elegant formal dining room and parlor in the front of the house to an open concept kitchen and family room in the back. On warm days, throw open the french doors on either side of the stone fireplace, and walk out onto the large stone paved patio encompassed by a cozy sitting wall. The outdoor fireplace will keep your guests warm on cool spring and fall evenings. It's an entertainer's dream. The kitchen and butler's pantry are outfitted with custom built cabinetry, honed Taj Mahal quartzite countertops, top-of-the-line appliances and elegant lighting for a cozy and polished living space. Also on the first floor are a bedroom that can be used as an office with an ensuite bathroom, a stately powder room and a mudroom and additional storage for containing an active household. The opulent master bedroom on the second floor flaunts grand 13-foot vaulted ceilings with transom windows framing the property's 200-yr old oak and maple trees in every season, customized walk-in closet and a tranquil bathroom with custom built vanity and dressing table. In the master bathroom, luxuriate in the Kohler vichy body and rain showers or soak the day away in the Victoria and Albert volcanic limestone bathtub, and never walk on cold tiles again on frigid winter mornings with programmable heated floors. On the second floor are 3 additional spacious bedrooms, two that share a Jack-and-Jill bathroom and one with a chic ensuite bathroom. All 2nd floor bathrooms floors are heated. The third floor houses a bright bedroom with a southern exposure, a roomy bathroom with sophisticated stone and tile work, a window seat at the end of the hall that's perfect for a reading nook. Down in the basement are all the amenities for relaxing and entertaining. The ample recreation room is furnished with built-in shelves around the TV wall and cabinets to contain games and consoles. A polished custom antique mirrored wall and brass bar tap faucet details lend sophistication to the wet bar. Remaining living spaces include a 7th bedroom, a bathroom and an exercise room waiting to be turned into a home gym, a private yoga or pilates studio or a dance studio. White oak flooring and stairs throughout the house, pre-wired for customized home entertainment systems by Hooked Up Installs, Inc., underground storm water drainage systems around the periphery of the property, programmable irrigation systems, 2-car garage with space in the attic for additional storage and a gorgeous stone paved driveway that's the envy of the neighborhood! Move into this lovely house and the serene neighborhood today! BROKER OWNED

747 Walden Road, Winnetka

$750,000
2 Beds 2 Baths 11842543 MLS PENDING Status
Fantastic, bright & elegant 2 bed 2 bath, 2nd floor unit with sunny west facing balcony located in the heart of Winnetka's tree streets. Built in '97, the combination of open concept and dedicated spaces merge to form the perfect floor plan. White kitchen with custom cabinetry, island seating & office desk area is adjacent to separate dining room. Dining room is open to living room and has a sliding door to the balcony with room for seating. Spacious living room is scaled for entertaining family and friends, complete with custom built in bookcases suitable for an entertainment system and personal library. The living room can accommodate 2 seating areas. There is also plenty of space for a piano or card table. Oversized primary suite features a wall of windows with transom, allowing natural light to filter through during the day with a glimpse of tree-top views. The primary bath boasts a double sink, separate shower and tub, water closet and organized walk-in closet. Second bedroom has double closet, custom bookcases & shares the 2nd full bath across the hall. In unit laundry within the outfitted utility closet. Additional features: hardwood floors in main rooms, carpeted bedrooms, lofty ceilings, wide hallways, generous built out closets, high-end custom cabinetry, millwork, crown molding and wainscoting. Attractive brick exterior, recently renovated lobby and hallways throughout, bench seating in private courtyard. Two (2) garage spaces (#2 and #3) and storage unit (#9). Live in the center of the village - close to everything: train, shops, restaurants, Dwyer park, award winning schools (K-8), post-office, banks, the beach - you name it! Unit is in an estate and being sold As Is.

812 Oak Street Unit #201, Winnetka

$3,990,000
4 Beds 6 Baths 11821089 MLS PENDING Status
Introducing an extraordinary masterpiece that redefines luxury living. Designed by renowned architect Paul Konstant, this contemporary farmhouse is a true marvel, surpassing anything you've ever encountered. Completed in 2016, this home boasts unique and exquisite finishes, including a professional-level tennis court and a wine cellar for your prized collection. No expense was spared in crafting every detail to perfection, highlighting the expansive and sunlit floor plan that sets the standard for seamless indoor-outdoor resort-like living. Meticulously engineered with state-of-the-art technology and minimalist sophistication, this home caters to today's discerning buyers. Step onto the heated circle drive and enter through the stately glass doors into the reception foyer, surrounded by panoramic windows that showcase the breathtaking views. The heated limestone flooring throughout adds an opulent touch, while the soaring ceilings create an air of grandeur. Off the foyer, you'll find separate mudroom areas, each thoughtfully designed with custom cubbies and convenient access to the 3-car attached heated garage. Indulge in the sun-drenched great room, the heart of this entertainer's paradise, seamlessly combining a gourmet kitchen, dining area, family room, and a full-size bar. The sleek chef's kitchen features galaxy-white waterfall countertops, island bar seating, and top-of-the-line appliances from Miele, Wolf, and SubZero. Additionally, a walk-in butler's pantry and storage pantry offers ample space for culinary endeavors. Soaring high above, the beamed ceilings create a visual spectacle that immediately captures attention. Crafted with precision and artistry, the beams traverse the expanse of the ceiling, adding depth, character, and a touch of warmth. The family room is anchored by a custom stone fireplace, window seats, and a fully equipped bar, all overlooking the heated courtyard patio, grilling station, and tennis court. The back wing of the home hosts four custom-designed bedrooms. The redesigned luxurious primary suite has vaulted wood ceilings, and two large walk-in closets and the bath boasts dual vanities, a soaking tub, and a walk-in steam shower. Bedroom two with built-in queen beds and an ensuite bath, and a hidden second-floor loft complete the picture-perfect accommodations. The third bedroom is currently set up as an office. Ascend to the second level to discover the ultimate 4th bedroom/guest suite, featuring a separate kitchen and sitting area. The finished lower level is where you will find the 850-bottle wine cellar where your passion for wine finds its perfect sanctuary - no detail has been overlooked, from the carefully selected materials to the expert craftsmanship. This temperature-controlled environment ensures optimal conditions for aging and preserving your most cherished bottles. The state-of-the-art cooling system guarantees precise temperature and humidity control, safeguarding your collection and allowing your wines to reach their full potential. In addition, the lower level has a spacious recreation room with a theater screen and a fifth bedroom with a full bath. Situated on one acre of meticulously landscaped grounds, this property embodies modern perfection. Experience resort-style living with this extraordinary outdoor patio, boasting not only a professionally designed tennis court but also an expansive fenced-in yard that will transport you to a private oasis of luxury. Don't miss this rare opportunity to own this breathtaking one-of-a-kind custom home.

111 Woodley Road, Winnetka

$4,250,000
4 Beds 6 Baths 11813711 MLS PENDING Status
Nestled within 1.2 acres of verdant, professionally landscaped grounds, this breathtaking singular interpretation of 18th century American architecture offers unparalleled luxury in a most picturesque setting. Under the helm of architects Tom Beeby, an original member of the Chicago Seven, and Lawton Theis, meticulous craftsmanship and refined design offer the most discerning buyer a seamless blend of classical and traditional with the highest modern standards. A collaborative labor of love, the design and construction of these enchanted grounds and property left no detail undone. Upon entry, the unparalleled level of finish is immediately evident with soaring ceilings, rich hardwood floors, exceptional craftsmanship, millwork and an overall ambiance of refined grandeur and warmth. A generously sized dining room with marble surround fireplace and designer upholstered walls offers ample room for seated dinners and entertaining. The gourmet kitchen features top-of-the-line appliances (Sub-Zero, Viking, KitchenAid, etc.), a charming breakfast area with views overlooking a beautifully landscaped terrace. Beyond the kitchen/breakfast room, a recently added (2023) spectacular sunroom (everyone's favorite retreat) fitted with remote retractable screens, a soaring coved ceiling and a gas fireplace, provides a serene setting for morning coffee and more! With expansive space to spread out and relax in the utmost comfort, 1st floor living areas include a family room with an exceptional, wood-paneled bar, a handsome library/office and a stunning living room with fireplace and views of the elegant front courtyard. A sanctuary of tranquility, the primary suite completes the 1st floor and features lavish his and hers en-suite bathrooms with marble accents and exceptional walk-in dressing room and closet. The 2nd floor features 3 additional bedrooms, 2 full baths and extensive storage space. The lower level with lofty ceiling heights encompasses an oversized rec room, temperature controlled wine cellar, playroom/or bedroom 5, a potential bath that has been stubbed for plumbing, several storage areas and a generous, unfinished bonus area with tall ceilings, primed for a golf simulator. Additional features include: heated, attached 3-car garage, 1st floor laundry room, mudroom, walk-in pantry, professionally designed interiors and exterior grounds meticulously by Craig Bergman. The exceptional grounds and gardens can be enjoyed by the expansive bluestone patio or most rooms on the first floor due to the brilliant U-shaped design. One floor living at its finest. Set on one of the most desirable private roads, this one-of-kind home designed in the spirit, style & form of Gunston Hall (Fairifax County, VA home of George Mason signatory of the Declaration of Independence) offers a fusion of timeless beauty and modern luxury, providing a haven of sophistication, tranquility and an extraordinary place to call home. Showings begin 6/27 at broker open.

25 Indian Hill Road, Winnetka

$2,289,000
4 Beds 6 Baths 11813039 MLS PENDING Status
Private daily entrance on Maple Street - steps from the Lake. Rare opportunity for newer construction brick classic on large lot in premier neighborhood: close to Maple Street Beach, parks, town and train. Designed with distinction and set on over 1/3 acre of grounds surrounded privately by foliage with lake breezes and seasonal third floor lake views! Openness and serenity throughout with gracious well proportioned rooms offering a fabulous open floor plan on four levels. High ceilings, custom millwork and fine architectural details. The main level has an open foyer, formal living room with stunning fireplace, bright dining room with butlers pantry leading to the updated smartly designed gourmet kitchen with island and breakfast area leading to spacious family room with handsome fireplace, leading out to the patio and back yard. The first floor also includes a private office and a mudroom accessed from the two car attached garage. The second floor offers a spacious primary suite with a third fireplace, a large en-suite bathroom with tub, dual vanities and walk-in, steam shower plus walk-in-closets (including a walk-out to an attic storage space above the entire garage). Three further spacious bedrooms on the 2nd level, one with an en-suite bathroom and the other two share a "jack and jill" bathroom plus a great 2nd floor laundry. The third floor tree-top suite offers seasonal lake views with a full bathroom and bonus hang-out space/office. The extraordinary lower level boasts a huge recreational room with wet bar, ice maker and dishwasher as well as a media/exercise room, a 5th bedroom and full bathroom and excellent storage. Private fenced back yard and bluestone patio with access from Maple St. Open space provides opportunity for play for "all ages". In addition, the front entrance features a brick paver circular driveway off Sheridan Road. Exquisite private retreat in premiere walk to all location! Total estimated above grade sq ft = 5205 and total estimated including basement sq ft = 7146. Please make appointments in Showing Time.

670 Sheridan Road, Winnetka

$3,750,000
6 Beds 8 Baths 11816185 MLS ACTIVE Status
LOCATION, LOCATION, LOCATION! This magnificent French Chateau located on the North Shore of Chicago is magically set on the premier "Sheridan to Shore" drive in East Winnetka, This spectacular home's location arguably is one of the best pockets on the entire North Shore that sits on a half acre, surrounded by exquisite homes, Lake Michigan and steps from Winnetka's premier Maple & Tower beaches. Prepared to be wowed, as you enter the stunning grand foyer with twin winding staircases- you're greeted by an enormous sun-filled and elegant living room with floor to ceiling windows overlooking the backyard. The home offers a flexible floor plan with first floor library, en suite bedroom, formal living room & spacious dining room. Newer kitchen and family room open to an awesome deck with a pergola and backyard. Fabulous for entertaining both inside and out. Good-sized laundry room and a guest powder room complete this level attached 3 car garage. Second floor features an expansive Primary Suite with a spa-like bathroom, sauna and huge walk-in closet. All other bedrooms are very generously sized with lots of windows and light and have ensuite bathrooms. The finished basement is enormous - first impression could fit a bowling alley, hockey rink, soccer field - it includes a full level of living and entertaining space with guest room, full bathroom, sauna, second full kitchen, bar & full home theater. 3 car attached garage. Large driveway with a bluestone turn around and additional parking spaces. This is PRIME East Winnetka. Don't miss this wonderful opportunity to experience the best location Winnetka has to offer - Close to downtown Winnetka & Hubbard Woods, Metra & Greeley Elementary School & New Trier. You will fall in love! Make us an offer - very negotiable - motivated seller.

745 Sheridan Road, Winnetka

$4,975,000
7 Beds 9 Baths 11800099 MLS ACTIVE Status
An extraordinary testament to the highest standards of luxury living! This home was completely gutted down to the studs and masterfully reimagined by award-winning architect, Karl Straussburger. Whether you're an athlete, artist, chef, or simply an enthusiast, this property is custom-built to suit your needs. One of only 14 homes on Lake Longmeadow with exclusive riparian rights and the only home on the lake with an incredible private peninsula. Along the waterfront is the ultimate fishing hub, abundant with bass, bluegill, and other natural wildlife. A retaining wall to prevent erosion has been installed by the US Army Corps of Engineers. A floating dock off the lake provides access to the water and leads to a separate brick patio, which offers views of the serene natural surroundings. The patio also features a cozy fire pit, perfect for enjoying the beauty of the outdoors while staying warm and comfortable. With 111 feet of lakefront access and riparian rights, this home is perfect for kayaking, paddle boarding, fishing, and ice skating in the winter months, all from your quiet backyard. The grandiose backyard has been impeccably landscaped, including an invisible dog fence in the backyard, and still with enough room to add a swimming pool. The prime outdoors of this home is adorned with apple and peach trees as well as a tomato and herb garden. Every inch of the property has been thoughtfully redesigned and beautifully updated to create a truly breathtaking living experience. From the moment you step off the custom brick circular driveway and enter through the magnificent foyer, you'll be greeted by an open and spacious floor plan, where all of the home has been perfectly designed with meticulous detail that is apparent in every room. The main floor, with all hardwood flooring throughout, flows from the brightest piano room with a fireplace to a separate formal dining room with comfortable seating for 12 people. Also on the main level are two custom-designed offices with fantastic custom woodwork, a powder room, an elevator connecting 3 floors, and an expansive mudroom. The picturesque kitchen with a butler's pantry and informal dining space is an entertainer's dream, with serene views of the backyard, and connects to the living room with a fireplace. Off the kitchen is a bright sunroom with 100-year-old barn wood accents and heated floors, and a fireplace that opens to the grand brick outdoor patio space. The second floor boasts 5 en suite bedrooms with the finest finishes, heated bathroom floors, and large walk-in closets. The impressively spacious primary suite is a true retreat and opens to a balcony with the best views of the backyard and lake. Adjacent to the primary suite is a separate sitting room, and a spiral staircase leading to a private library above the primary bedroom with more impeccable woodwork, which is illuminated by four custom stained-glass skylights. Also on the third level is a safe room, full bath, and two large rooms currently being used as an artist studio and film developing studio but could also be bedrooms. The lower level continues to impress with an additional bedroom with a full bath and kitchenette that makes for a private part of the home for hosting guests. A few stellar features of the home reside on the lower level with a full temperature-controlled glass wine cellar, complete with a separate private tasting room with custom wood accents. The theater boasts 3 rows of seating and is uniquely adorned with a charming back row to mimic vintage theater seating. The theater is also equipped with double soundproofed walls and ceiling making for an idyllic viewing experience. Also along this level are two expansive gym and exercise rooms, one with 10 ft ceilings adequate to add a golf simulator, and another bathroom with a sauna connecting to the other exercise room. Don't miss out on the opportunity to make this exquisite home your own and experience the very best in upscale living!

104 Longmeadow Road, Winnetka

$5,250,000
7 Beds 8 Baths 11789138 MLS ACTIVE Status
REIMAGINED LUXURY - Immerse yourself in the exquisite transformation of an English manor estate nestled on a private lane within one mile of Winnetka's town center. 35 Indian Hill was extensively renovated (exterior and interior- see upgrades under additional information) in 2017 and 2021. Set on approximately 2.3 acres of lush grounds adorned with a fountain, swimming pool, and a spring fed lake, this home has been meticulously redesigned to meet the highest modern standards. As you step into the grand foyer, a circular stairway greets you. Beyond the dramatic entry lies the dining room, adorned with hand-painted country scenes, custom silver leaf paper, and new lighting fixtures that create an enchanting ambiance. The living room, featuring original bookshelves and a fireplace, seamlessly leads to the preserved oak paneled Library/Game Room reminiscent of classic English architecture. The Pine Room, a cozy and inviting space, beckons for fireside movie screenings or sipping cocktails on warm summer nights, with the doors open to the outdoors, perfect for entertaining. Adjacent to the formal dining room, the Modern Bar & Butler's Pantry boasts a nickel sink, Subzero beverage drawers, wine storage, and custom cabinetry all leading to the contemporary kitchen. Vibrant variations of blue adorn this culinary haven, featuring a separate pantry, leathered Dolomite stone countertop on center island and custom cabinetry and lighting. Top-of-the-line professional chef appliances, including a Wolf double range, two Bosch dishwashers, True commercial refrigerators, a Subzero freezer, ensure that cooking becomes a true delight. The adjoining eating area seamlessly transitions to a glass conservatory overlooking the brick walled garden to ensure privacy. The casual family room opens up to inviting terraces outside. Ascend the grand stairway to the second floor, where the reimagined primary bedroom wing awaits, boasting two walk-in closets, a sitting room with a fireplace, and a luxurious bath featuring a soaking tub overlooking the grounds, a separate steam shower & commode room along with custom millwork cabinetry/drawers topped with double sink stone vanities. Two additional bedrooms (and a third shown as home office) each with new ensuite baths, and a generous gym that is sure to inspire, complete the second floor. The third floor boasts two light-filled bedrooms that share a full bath, accompanied by a cedar closet and a large multi-purpose room. The basement encompasses several storage rooms, a half bath, and a second full laundry area and allows for exterior access. All these features & benefits ensure that every aspect of comfortable living is accommodated. No detail has been overlooked in this exceptional home. Additional features include an oversized 4-car heated garage, an elevator, heated floors, professionally designed interiors, new zoned HVAC, a new slate roof, smart technology lighting, and custom built-ins throughout. This residence provides four seasons of indoor/outdoor living: endless gardens to stroll, afternoon swims in the summer, brisk ice skating in the winter on the pond, and touch football games surrounded by fall colors. This truly one-of-a-kind property presents limitless possibilities and is certain to captivate discerning buyers seeking unparalleled luxury and privacy.*******Proof of funds required before showing confirmation *******

35 Indian Hill Road, Winnetka

$6,999,900
6 Beds 9 Baths 11786905 MLS ACTIVE Status
When the curb appeal of a house is so exquisite, it speaks for itself! This is the most exquisite full house restoration in the entire North Shore. The flawless blend of a carefully selected hue of French light blue shutters against the timeless beauty of lime-stained white brick, all framed by a pebble stone motor courtyard creates a timeless vision of architectural perfection. This magnificent North Shore estate possesses an undeniable "IT factor" that sets it apart from the rest. This is just only the beginning to describe this award winning home set on "Versailles like" manicured gardens on 1.3 acres with a flawless 6 star FULL house renovation & addition w/ a 3-car attached showroom style radiant heated garage. The reawakening of this classic S.S Beman home is brought to modern day excellence by the vision of notable architect, J. Lawton Thies. Step inside to the captivating foyer as your eyes wonder through the double Dutch door with the site of the matching cabana house & pool in the distance surrounded by marvelous gardens, enchanting dining patios & scalloped grey and white stripped accented awnings. Boutique hotel vibe radiates from the pool cabana house with WB fireplace, white marble bath, laundry and kitchenette with great room. From the French inspired light blue & white O'Brien Harris kitchen accented with Borghini marble countertops & backsplashes, Grand Palais La Cornue range and a buffed zinc paneled hood bordered in polish nickel to the conservatory with a botanical themed hand painted mural, tumbled white & black checkered marbled heated flooring overlooking the Parisian fountain and splendid rose beds, there is not one room that isn't extraordinary. Over 11,000 square feet of pure luxury with stunning natural sawn oak floors with new subfloors, meticulously restored plaster moldings, French Regency windows with brass hardware, and exquisite marbles and stones, every detail speaks of opulence & elegance in this extraordinary space. Expansive snow melt driveway, heated garage flooring w/lift system, all new low voltage lighting & engineering brings this home right up to todays speed. Experience a house renovation that was executed to outshine all modern day needs with 6 bedrooms including a primary with separate his/her marble baths, dual laundry, separate entrance wing in-law suite w/ full bath and the best in class & finishes. It's all here with even a creme de le creme location for all schools; Crow Island, FHC, Loyola, NSCD and New Trier. Privately off Hill Road in it's own world of tranquility with a sensational southern facing orientation, this North Shore estate is the perfect blend of old grace & modern day elegance. This is estate turn key perfection...and it is THIS that is extremely rare in the entire North Shore!

969 Hill Road, Winnetka

$3,295,000
6 Beds 8 Baths 11749607 MLS PENDING Status
Exceptional and captivating country get-away in the heart of Hubbard Woods with over an acre of lush landscapes. Expansive blue stone terrace surrounds the incredible interior renovations found within this extraordinary home (architectural design by Morgante Wilson and custom interior design by designer/owner) . Steps from shops, restaurants, train, schools K-8 and parks, this enchanting get-away is truly a forever home. Of the many highlights, the new gorgeous kitchen which opens beautifully to a large family room and outdoor patio -all which has been designed with utmost perfection -represents the utmost attention to every detail found throughout this extraordinary home. A large island, custom cabinets, stone counters, high-end appliances and a breakfast area for a large gathering is ideal. The fabulous family room with fireplace and lovely views offers room for the crowd. A dramatic curved bar is perfect for entertaining and is easily accessed from one of the most incredible dining rooms in Winnetka with impressive proportions, designer finishes (plus wine fridge and ice maker) and French doors to the terrace which are perfect for entertaining. Also near the kitchen is the mudroom entrance with extra closet space. The first floor continues to a handsome office for two with custom features throughout and large windows which view the terrace and spectacular yard. The adjacent formal living room with grand proportions, custom built-ins and French doors to the patio is ideal for entertaining. A formal powder room is located off the main entrance hall and a second powder room is located near the mudroom and staircase to the second floor. The expansive second floor features an exquisite primary suite wing with a luxurious bedroom with sitting area, spa marble bath with double vanity, tub, fabulous shower, water closet plus enviable walk-in closets for two. The second floor continues to three secondary bedrooms, each with updated private baths and a bonus second laundry room. The full third floor includes a spacious media room, large bedroom, full bath and crafts/bonus room. The classic lower level offers an additional media area with adjacent billiards room and exercise area, laundry room, powder room and loads of storage rooms. The private outdoor oasis is unparalleled with a huge lawn, putting green, majestic trees, tetherball, gardens, fire pit at terrace, chef's grilling area and a delightful al fresco dining patio. Plenty of room for a future pool if desired. All that this home offers is steps from the charming Hubbard Woods shopping area, restaurants, park, train plus enchanting paths to Hubbard Woods school for utmost convenience . An offering like no other all in the heart of Hubbard Woods.

860 Auburn Road, Winnetka

$2,799,900
5 Beds 8 Baths 11699258 MLS PENDING Status
Right on target, after the December delivery of jaw dropping 425 Sunset Winnetka. OCT 2023 delivery of this architectural beauty w/an edge of sophistication & comfort. Set on maturely landscaped extra wide 78 x 161 lot on a cul-de-sac with curved driveway, this sensationally designed 6 bed, 6.2 bath home hits all marks as the attention to detail & design if off your favorite inspiration Pinterest page! Warm colored hues threaded throughout all natural stones, hand sanded white oak floors, and floor-to-ceiling Pella windows throughout. Sun drenched reception hallway with a desirable open floor plan and cozy office with custom built-ins. Oversized Great room highlighted by more custom built-ins and stately fireplace opening up to the unbeatable Chef's kitchen with top of the line customizable appliances, custom cabinetry, huge walk-in pantry, large island with breakfast bar seating, and access to the large dining room overlooking the backyard and covered patio. Two powder rooms and built-out large mudroom on this level. Beautifully crafted staircase to the second level with 4 ensuite beds including a massive primary suite with awesome walk-in closets. Spa-like master bathroom with quartz and marble finishes with dual vanities, soaking tub and shower. Bonus third floor loft or play room also has 5th bedroom and full bath. And that's not all....head downstairs to practice your golf swing, hit the gym, entertain in the game/recreation room or just cozy up by the fire! Jump in now to collaborate with the most talented builder and customize your upgrades and finishes before it is too late! The time is now to experience new construction with a trendy cozy flare. Only thing missing in the background is the mountains!

1361 Edgewood Lane, Winnetka

Start Your Search



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2023 MRED LLC. All rights reserved.

Based on information submitted to the MRED as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MRED. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Winnetka Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Winnetka and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!