Browse All Winnetka IL 5 Bedroom Properties for Sale

5 Beds ⋅ 8 Baths ⋅ 12672761 MLS ⋅ CONTINGENT Status

Winnetka

5 Beds ⋅ 3 Baths ⋅ 12703898 MLS ⋅ PENDING Status

An extraordinary Colonial offering timeless elegance, exceptional estate-like privacy, and breathtaking views along the 12th hole of the Winnetka Golf Course. Set on nearly one acre of beautifully landscaped grounds and positioned approximately 250 feet from the road, this property feels like a private retreat yet is just minutes from downtown Winnetka, the Metra, premier shopping, dining, and award-winning schools. Designed for both elegant entertaining and everyday living, the home features generously scaled rooms, hardwood floors throughout, and an inviting floor plan. The living room with fireplace and custom built-ins flows seamlessly into the formal dining room, while the sun-filled family room showcases sweeping golf course views. An updated kitchen with a spacious breakfast area anchors the home, and a first-floor den provides flexible space for a home office, library, or fifth bedroom. The primary suite is a private sanctuary with a fireplace, sitting area, outdoor deck, and stunning views. Thoughtfully renovated and maintained by the current owners, this exceptional home offers a bucolic setting, golf course walks and cross-country skiing outside its back door. Cherished by the same owners for the past 28 years, a true testament to the home's timeless appeal.

1440 Tower Road, Winnetka

$1,725,000

5 Beds ⋅ 5 Baths ⋅ 12711173 MLS ⋅ CONTINGENT Status

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".

555 Cherry Street, Winnetka

$4,200,000

5 Beds ⋅ 9 Baths ⋅ 12701871 MLS ⋅ ACTIVE Status

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

1128 Mt. Pleasant Road, Winnetka

$2,795,000

5 Beds ⋅ 6 Baths ⋅ 12688601 MLS ⋅ ACTIVE Status

Basement renovation just done to add 6th bedroom that adjoins full bath! So much light enters basement through windows! A rare opportunity to own a home on one of the most sought after, serene country-like settings on the North Shore. The house is just steps from the Indian Hill Golf Club and part of the coveted Indian Hill neighborhood. Be close to other magnificent homes and wooded and mature landscaping. Only one owner since home was completed on this property in 2012. Stately and traditional two story brick home with 5 bedrooms and 5.1 baths. The large finished basement with overly generous storage allows for a 6th bedroom. The basement has a full bathroom and space that is plumbed and ready for installation of a kitchen. Your eyes are drawn to the gracious two story foyer finished in marble. The rest of the first floor is finished in hardwood oak and cherry except for the family room that has plank flooring. The wel designed first floor has spacious living room, dining room, family room, eat-in kitchen, den and mudroom. The enormous primary bedroom is a tranquil retreat with spa like bath with jacuzzi and walk-in shower finished in travertine tile. The new owner will greatly appreciate the two walk-in closets located in this escape space. There are four other bedrooms on the second floor. Mature landscaping and brick pavers offer welcoming outdoor space. The driveway also boasts of brick pavers. Approximately 4319 square feet of above ground living space and 2066 below in basement for a total of 6385 square feet of enjoyable space. So close to schools, shopping, and even the beach. Enjoy the incomparable Winnetka lifestyle. Hurry, because this house, designed for everyday living and gracious entertaining, will not last long!

73 Locust Road, Winnetka

$4,949,000

5 Beds ⋅ 7 Baths ⋅ 12698685 MLS ⋅ ACTIVE Status

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

320 Woodley Road, Winnetka

$4,950,000

5 Beds ⋅ 7 Baths ⋅ 12283033 MLS ⋅ ACTIVE Status

Nestled down a winding, private road on 1.9 meticulous park-like acres, this grand, almost 10,000 square foot residence exudes luxury and timeless elegance. The front entrance is set apart from the road by a sweeping circular drive bordered by private hedges and mature trees. Upon entering the stately, two-story foyer with a 25' ceiling, bridal staircase, black and white marble floor, formal powder room and two coat closets, you are greeted by the sophistication that defines this home. The main level features a spacious, step down living room with inlaid floors, a marble, gas and wood fireplace, and two picture windows that fill the room with natural light. Pass through the living room to an adjoining, architecturally beautiful solarium with a slate floor, that offers panoramic views of the lush grounds surrounding the residence. The formal dining room also features inlaid floors, and picture window. The handsome family room with custom cabinetry, lighting, millwork, and a marble, gas and wood fireplace, provides the perfect space for entertaining and relaxation while overlooking a yard large enough for a pool. The family room seamlessly flows into a large kitchen area that includes not only a custom kitchen but also a breakfast room, butler's pantry, back staircase, and mud room. The butler's pantry has an ice maker, second dishwasher, and beverage refrigerator. Upstairs the luxurious primary bedroom suite boasts a marble, gas and wood fireplace, walk-in closet, and an adjoining sun room with stunning views of the grounds. It is perfect for family gatherings, office space or nursery. Adjacent to the dual sink primary bath with a vanity table, there is a winding staircase that leads upstairs to the third floor where you will find a beautifully crafted wardrobe/dressing room with many custom built-ins, lighting and mirrors. This lovely area conveniently leads to an exercise room, powder room and an oversized cedar closet, and this completes the third floor. There are four additional family bedrooms on the second floor, two share a Jack and Jill bathroom, one has its own en-suite, and the fifth bedroom suite offers versatile living space. The fifth bedroom and sitting room, located near the back stairs, welcomes an in-law arrangement, live in nanny, or out of town guests. The full basement offers at least another 2444 square feet of living space and includes a large recreation room with fireplace, billiard room, wet bar, spacious laundry room, large cedar closet, another storage room with built-in shelving, and a powder room. The yard is professionally landscaped, private, and nearly two acres is quite hard to come by in Winnetka. Additional features of this remarkable residence include: a three car, heated, attached garage, magnificent craftsmanship, glorious room sizes, four fireplaces, a slate roof, copper gutters, circular driveway and uncommon privacy. This residence is a true gem in the heart of Winnetka. Live a life of luxury and sophistication in this exceptional home. Woodley Road, with its canopy of mature trees, is a coveted private oasis, and yet is conveniently located near town, train, restaurants, schools and a public golf course. This property is not located in the flood plane. NO SIGN

32 Woodley Road, Winnetka

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