Browse All Winnetka IL Historical Properties for Sale

4 Beds ⋅ 5 Baths ⋅ 12751307 MLS ⋅ NEW Status

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

579 Hill Terrace, Winnetka

$899,000

3 Beds ⋅ 2 Baths ⋅ 12743165 MLS ⋅ RE-ACTIVATED Status

A rare opportunity on one of Winnetka's most beloved neighborhood streets. Welcome to 790 Foxdale Avenue, a charming Dutch Colonial offering timeless character, a wonderful sense of community and an exceptional location in the sought-after Greeley Elementary attendance area and New Trier High School district. Foxdale is more than just a beautiful tree-lined street-it's the kind of block where neighbors know one another, kids are often outside playing and spontaneous conversations happen at the end of the driveway. Longtime neighborhood traditions have included Flamingo Fridays, block parties and even a "Foxdale Float" in Winnetka's Fourth of July Parade. It's vibrant, welcoming and the kind of street that inspires people to say, "Foxdale-that's a fun block." This well taken care of home offers classic curb appeal with durable, low-maintenance composite siding and a newly fenced backyard. Step inside to hardwood floors, original architectural details and a surprisingly generous entry coat closet. The spacious living room features a marble fireplace with flanking built-ins, while the formal dining room flows into the kitchen with white cabinetry, stainless steel appliances and a charming breakfast nook overlooking the backyard-a perfect spot for morning coffee, casual meals or homework. Upstairs are three bedrooms, a full bath and a versatile bonus room adjoining one of the bedrooms. Currently used as a home office, this flexible space could also make a wonderful playroom, sitting room, nursery or creative retreat. The finished lower level provides additional recreation space, laundry and a workshop, while a playful hidden wine nook tucked along the stairway adds an unexpected bit of character. Outside, the private newly fenced backyard features a brick paver patio and built-in fire pit, creating an inviting setting for dining, entertaining and play. A two-car garage completes the property. Beautifully maintained and inviting as it stands, the home is also an ideal canvas for a buyer to add their own finishing touches and thoughtful cosmetic updates over time. Ideally located near downtown Winnetka, Hubbard Woods, Metra, the Green Bay Trail, parks, beaches and everything the village has to offer, 790 Foxdale presents an increasingly rare opportunity to enjoy a classic Winnetka home on a street known as much for its community as its location. Select images have been AI-rendered to help illustrate the home's amazing potential with cosmetic enhancements and are intended for visualization purposes only. Buyers and agents to verify all finishes and dimensions in person.

790 Foxdale Avenue, Winnetka

$1,295,000

4 Beds ⋅ 3 Baths ⋅ 12737437 MLS ⋅ PENDING Status

Timeless Elegance Meets Modern Luxury with this prime Winnetka home on a large corner lot. Discover the perfect blend of historic character and contemporary living in this meticulously maintained residence. From the moment you step inside, rich vintage craftsmanship takes center stage, highlighted by striking coffered ceilings, multiple cozy fireplaces, and an exquisite built-in buffet. At the heart of the home is a spectacular chef's kitchen that flows seamlessly into the expansive family room, creating an ideal hub for both daily living and grand entertaining. Retreat to the sprawling primary suite, a private sanctuary complete with a boutique-style walk-in closet, a dedicated sitting room, and an updated bath. The sprawling yard has plenty of room for games and entertaining. Exceptional bonuses include an abundance of storage via the attic and crawl space. The location provides unbeatable North Shore convenience. Step out your front door and walk to top-rated schools, Duke Childs Field, and the vibrant shops and restaurants of Hubbard Woods. The listing agent is related to the seller.

1110 Elm Street, Winnetka

$1,295,000

3 Beds ⋅ 3 Baths ⋅ 12718382 MLS ⋅ PENDING Status

600 Sheridan Road, Winnetka

$2,499,000

3 Beds ⋅ 5 Baths ⋅ 12732091 MLS ⋅ CONTINGENT Status

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!

1192 Chatfield Road, Winnetka

$2,950,000

4 Beds ⋅ 5 Baths ⋅ 12729556 MLS ⋅ PENDING Status

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!

567 Oak Street, Winnetka

$2,695,000

4 Beds ⋅ 5 Baths ⋅ 12715045 MLS ⋅ ACTIVE Status

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

1140 Oakley Avenue, Winnetka

$1,950,000

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

$1,395,000

4 Beds ⋅ 3 Baths ⋅ 12705964 MLS ⋅ CONTINGENT Status

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

$1,500,000

4 Beds ⋅ 3 Baths ⋅ 12699325 MLS ⋅ PENDING Status

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.

1360 Sunview Lane, Winnetka

$1,779,000

4 Beds ⋅ 3 Baths ⋅ 12683501 MLS ⋅ CONTINGENT Status

Nestled in an exceptional location, this beautifully appointed home offers the perfect combination of charm, comfort, and convenience. Just moments from vibrant downtown Winnetka, you'll enjoy easy access to outstanding restaurants, boutique shopping, the train station, and the beach-making it easy to embrace the very best of the community. Inside, the thoughtfully designed floor plan features spacious living areas ideal for both everyday living and entertaining. The inviting family room and elegant living room each showcase their own fireplace, creating warm and welcoming spaces to gather throughout the seasons. A delightful sunroom fills with natural light and provides the perfect place to relax, while the adjacent breakfast area offers a cozy setting for casual meals. The home includes four generously sized bedrooms and a spacious mudroom conveniently connected to the attached two-car garage, adding functionality to its timeless appeal. Outside, enjoy a wonderful outdoor living space with a beautifully fenced yard that offers privacy and plenty of room for play, gardening, or entertaining. With its unbeatable location, versatile layout, and exceptional amenities, this is a home that truly delivers the lifestyle today's buyers are looking for.

639 Lincoln Avenue, Winnetka

$1,795,000

3 Beds ⋅ 3 Baths ⋅ 12698922 MLS ⋅ PENDING Status

BRAND NEW ROOF JUST INSTALLED WITH TRANSFERABLE WARRANTY!! Beautifully maintained home offering over 4,300 square feet above grade on a rare 0.53-acre corner lot in a sought-after Winnetka location. The centerpiece of the home is the dramatic main living space featuring soaring vaulted cathedral ceilings, abundant natural light, and an impressive open feel that creates an immediate sense of scale and warmth. Hardwood floors and a flowing layout provide comfortable everyday living along with excellent entertaining space throughout. A heated and air-conditioned bonus room off the garage adds exceptional versatility, ideal for a home office, gym, playroom, studio, or additional lounge space. Situated on a generous corner lot with expansive outdoor space, the property offers endless potential to enjoy as-is or further personalize over time. Conveniently located near top-rated schools, parks, downtown Winnetka, and Metra access, this is a rare opportunity to own a home with outstanding space, character, and flexibility in an exceptional North Shore location.

180 Westview Road, Winnetka

$2,785,000

6 Beds ⋅ 6 Baths ⋅ 12680099 MLS ⋅ ACTIVE Status

Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush, manicured grounds set the stage. Inside, the craftsmanship is unmistakable. You'll find expansive living spaces defined by rich architectural details and massive windows that frame the private, park-like backyard. The chef's kitchen is a masterpiece of function and style, flowing effortlessly into inviting family spaces that feel warm despite their scale. A first floor bedroom includes a private full bath and access to the patio. The primary suite serves as a genuine retreat, complete with a spa bath and enough closet space to satisfy any wardrobe. A sitting area surrounded by windows and a walkout overlooks the exquisite property. Each additional bedroom is en-suite and generously sized, ensuring everyone has their own corner of comfort. The third level includes flexible space with 3 lovely rooms and a full bath. There is an extra bonus space above the attached garage-perfect for a studio! Outside, the property truly shines. The expansive patio and rolling lawns create an incredible backdrop for summer garden parties or a quiet evening under the stars. Living here means more than just enjoying a beautiful residence; it's about the Winnetka lifestyle. You're minutes away from world-class schools, boutique shopping in the village, the shores of Lake Michigan, and the Metra for an easy commute to the city. It's sophisticated, it's private, and it's ready for its next chapter.

82 Woodley Road, Winnetka

$2,250,000

4 Beds ⋅ 6 Baths ⋅ 12673083 MLS ⋅ ACTIVE Status

Rarely available first floor primary! Unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners. Owner extremely motivated!!!

42 Woodley Road, Winnetka

$2,569,900

6 Beds ⋅ 6 Baths ⋅ 12637769 MLS ⋅ ACTIVE Status

The time is NOW to jump on this "southern charm" architectural beauty on exclusive Woodley Road. Beautifully appointed on a magnificent 1.5 acre lush lot with rolling greens, this estate is in prime position to be elevated to the next level of luxury. With over 8500 square feet of classic tasteful space over three floors of living, this house could never be duplicated close for the list price as the land value alone is worth at least $2 million dollars. Step inside to a grand foyer entrance where timeless black and white checkered marble floors meet a dramatic double atrium staircase wrapped in elegant wrought iron setting the tone for the architectural beauty that unfolds throughout. Gracious comfort exudes throughout this 13 room estate with that desirable southern exposure that allows natural sunlight to flood through the endless windows outlining the incredible backyard. Step down to a beautiful formal living room with a stone Parisian FP & custom French doors that open up to the cozy sunroom with picturesque windows overlooking the backyard. Finely appointed dining room with Visual Comfort light fixture layered with de Gournay wallpaper, antique marble fireplace and another set of French doors open out to the bluestone patio and deep backyard. Finely crafted white Chef's kitchen by O'Brien Harris with Villa Blanca marble, Clark & Barlow hardware, antique mirrored backslash and Holly Hunt pendents. Seamless transition to family rm ideal for cooking and entertaining at the same time. Command center mudroom, 2 powder rooms, and brand new laundry room also on this level. Two staircases lead the way up to large 2nd floor with intimate "Ralph Lauren" inspired den richly finished in restored paneled chestnut walls & handsome built-ins w/ dark marble FP. Large primary suite with room for even more expansion over porch is completed with Ann Sacks white bath and gracious marble FP with custom built-ins accented by a built-in window bench. 3 additional bedrooms with one being a large family bedroom w/ en-suite bath. The other 2 beds share pretty all white redone bathroom. Up to the oversized fully finished 3rd floor with 2nd family room and 2 beds ideal for in-law quarters or nanny. Lower level with mechanicals and ample storage space. The vibe of this home is effortlessly inviting-warm, layered, and livable across all 3 finished levels, seamlessly blending indoor & outdoor living. And with ample space to add a pool, the vision of true Southern comfort could be fully realized, elevating this already timeless retreat into a personal resort unlike any other.

62 Woodley Road, Winnetka

$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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Winnetka Historical Real Estate

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