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$2,800,000
4 Beds ⋅ 5 Baths ⋅ 12760634 MLS ⋅ NEW Status
A rare Winnetka offering, this distinguished 1965 Hemphill-built Georgian residence showcases exceptional main-level living on a spectacular one-acre property. With a primary suite and two additional bedrooms on the first floor, the home embraces the ease of living predominantly on one level while retaining the scale, privacy and timeless North Shore architecture for which Hemphill homes are known. A classic red brick exterior creates a striking first impression, approached through a generous gravel courtyard. A columned bluestone entrance welcomes you into the gallery-sized travertine foyer, immediately establishing the grand scale and elegance found throughout the home. The dramatic step-down living room with fireplace offers an elegant setting for entertaining, while the formal dining room, with its handsome parquet floor, is equally suited to intimate dinners and larger gatherings. A formal powder room is conveniently located off the foyer. The richly paneled family room with bamboo flooring is warm and inviting, with a fireplace, wet bar and floor to ceiling built-in bookcases. The spacious kitchen, featuring a third fireplace, island, breakfast area and butler's pantry, brings wonderful character to the heart of the home and creates a natural gathering place for family and friends. The sunroom with slate floor provides a peaceful connection to the surrounding landscape. With three walls of windows and a distinctive built-in planter, the room is filled with natural light and offers wonderful views of the grounds, a perfect place to settle in with a book and watch the seasons change. The bedroom wing encompasses the primary suite with a large dressing room, doors opening directly to the bluestone patio and a bath with separate shower and tub and dual vanity. Two additional generously sized bedrooms share a full hall bath. A first-floor laundry/mud room adds everyday convenience, while a second powder room is thoughtfully positioned near the three-car garage which has an additional half bay for storage. Upstairs, a private suite offers remarkable flexibility with its own living area, bedroom, full bath and cedar closet making it ideal for guests, extended family or as a completely separate retreat. The home also has a large unfinished basement. The magnificent one-acre grounds, tucked into a quiet lane, are an integral part of the property. Towering mature trees and established landscaping create a remarkable sense of privacy and give the property the character that only comes with time. An expansive walled bluestone patio provides a beautiful extension of the home's living and entertaining spaces. A charming brick storage shed provides additional space for gardening, outdoor furnishings and seasonal storage. Ready for its next chapter, this special residence presents an increasingly rare opportunity - a remarkable property with the space, setting and flexibility to be thoughtfully personalized for its next generation of ownership. This is an estate sale and the home is being offered as-is.

64 Locust Road, Winnetka
$1,400,000
5 Beds ⋅ 5 Baths ⋅ 12736036 MLS ⋅ NEW Status
Set on approximately half an acre in sought-after Hubbard Woods, this five-bedroom + office, 4.1-bath home offers exceptional space, a versatile floor plan, and an outstanding North Shore location. The thoughtfully designed main level features a private office or living room, formal dining room, updated eat-in kitchen, and spacious family room overlooking the backyard, in-ground pool, oversized deck, and patio, perfect for gatherings with friends and family. A convenient mudroom provides direct access to the attached two-car garage. Upstairs are five bedrooms, an office and a dedicated laundry room, while the walk-up attic offers abundant storage and exciting potential for additional finished living space. Ready for its next chapter, the home presents a wonderful opportunity to update and personalize while enjoying a Hubbard Woods address rarely available at this price point-all within walking distance of the train, shops, and Winnetka schools.

874 Boal Parkway, Winnetka
$1,200,000
12759407 MLS ⋅ NEW Status
***Build your dream home!!!*** Amazing opportunity in the East Winnetka neighborhood, tear down and build your forever home! Original 1913 home standing on 11,555 sf 70x165 Corner LOT. Prime Winnetka location, walking distance to lake, parks, school, Metra stop and downtown Winnetka. 'As-IS/Where-Is' Estate Sale.

590 Willow Road, Winnetka
$1,200,000
5 Beds ⋅ 4 Baths ⋅ 12758782 MLS ⋅ NEW Status
***Build your dream home!!!*** Amazing opportunity in the East Winnetka neighborhood, tear down and build your forever home! Original 1913 home standing on 11,555 sf 70x165 Corner LOT. Prime Winnetka location, walking distance to lake, parks, school, Metra stop and downtown Winnetka. 'As-IS/Where-Is' Estate Sale.

590 Willow Road, Winnetka
$1,999,000
5 Beds ⋅ 5 Baths ⋅ 12755931 MLS ⋅ NEW Status
Completely reimagined and thoughtfully designed, 1288 Sunview is an exceptional Winnetka home set on a picturesque half-acre lot. The property has been transformed from top to bottom with a focus on design, functionality and quality, creating a home that feels entirely new while maintaining the character and setting of the original property. The spacious floor plan offers 5 bedrooms, 3 full bathrooms and 2 half bathrooms, including four bedrooms upstairs and a fifth bedroom with ensuite bath on the main level that can function as a second primary suite. Two beautiful masonry fireplaces serve as focal points within the home, adding warmth, character and a timeless architectural element to the thoughtfully designed spaces. Multiple living spaces include two family rooms, a dedicated office and a fully finished basement, providing exceptional flexibility for today's lifestyle. The home's design creates an easy flow between the living, dining, kitchen and family spaces, while the main-level bedroom offers versatility as a guest suite, bedroom or second primary. The upper level features a spacious primary suite along with three additional bedrooms and a full hall bathroom. A convenient second laundry area is located on the bedroom level, while the fully finished basement provides additional recreation and living space, along with laundry, storage and mechanical areas. Outdoor living is a major highlight, with an expansive back patio, generous backyard and rooftop deck overlooking the property. The huge half-acre lot provides an uncommon amount of outdoor space in this Winnetka setting and is ideal for entertaining, relaxing or enjoying time with family and friends. Additional features include a two-car attached garage with EV charging hookup, beautiful hardwood flooring and thoughtfully designed spaces throughout. Set in an exceptional Winnetka location, 1288 Sunview is just minutes from New Trier schools, Skokie Playfields, parks, downtown shopping and dining, Metra and the lakefront. A rare combination of thoughtful design, substantial living space, architectural character and an exceptional half-acre setting, 1288 Sunview has been completely reimagined for modern living and is truly move-in ready.

1288 Sunview Lane, Winnetka
$2,749,900
4 Beds ⋅ 5 Baths ⋅ 12433803 MLS ⋅ NEW Status

438 Birch Street, Winnetka
$1,649,000
4 Beds ⋅ 3 Baths ⋅ 12745759 MLS ⋅ CONTINGENT Status
Enjoy an East Winnetka lifestyle on a beautifully landscaped expansive .3 acre all brick home in an ideal location, only blocks to Tower Road beach, Hubbard Woods/Winnetka shops and restaurants, schools, parks, and train. This sophisticated Georgian offering a great circular floorplan, grandly scaled rooms filled with natural light, fabulous outdoor spaces with a fully fenced yard, and an attached 2+-car garage, is perfect for seamless everyday living and entertaining. The welcoming foyer with a gracious staircase centers the home and opens to a spacious sunny living room with a gas log fireplace and handsome mantel. A comfortable family room with custom built-ins and oversized windows has panoramic vistas of the grounds and mature trees.The gourmet kitchen features custom cabinetry, high-end appliances, a large island with table seating, and a sitting area for play or relaxation with access to a private patio to enjoy al fresco dining and outdoor living. The elegant dining room is ideal for any size gathering. Upstairs the private primary includes a renovated ensuite bath and a large cedar lined walk-in custom closet. 3 additional generously sized bedrooms share a beautifully renovated hall bath with a double sink. The basement with laundry has abundant storage and awaits your design ideas. Hardwood flooring is under all carpeting. This is a great opportunity for a timeless East Winnetka home in a walk-to-all location.

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

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

1380 Westmoor Trail, Winnetka
$2,000,000
4 Beds ⋅ 5 Baths ⋅ 12751307 MLS ⋅ CONTINGENT Status
**Multiple Offers Received** Highest and Best due Tuesday 9/15 by 9am** 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
$1,950,000
3 Beds ⋅ 4 Baths ⋅ 12748077 MLS ⋅ PENDING Status
An inviting front porch welcomes you to this custom home designed by Reynolds Architecture. Fresh interiors with designer finishes and details create the feel of this curated residence, reflecting a modern sensibility and balance of casual and formal living. The foyer showcases herringbone hardwood floors leading to all first floor rooms. Custom cabinetry lines the hall adjacent to the elegant white kitchen, which features an oversized island, new marble counters, Artistic Tile marble backsplash, Visual Comfort lighting, high end appliances, dining area and new French doors. The adjoining great room features a fireplace and wall of built-ins beneath a coffered ceiling and opens to the sun room featuring new Marvin windows overlooking the professionally landscaped yard, pond and patio. An elegant dining room provides ample space for entertaining. An unexpected upgrade is the elevator servicing all three levels offering a rare and genuine alternative to one floor living, without sacrificing scale or architectural interest. A convenient powder room and mud room with a walk-in closet complete the first floor. The second floor includes a spacious primary suite featuring an oversized walk-in custom closet. The primary spa bath with two separate vanities, separate shower, tub and heated floor offers an ideal retreat. Two additional generously sized bedrooms share the hall bath, one ensuite and one accessed from the hall. Additionally there is a bright second floor laundry room that offers abundant counter space, and a walk-in linen closet. The impressive lower level offers a fourth bedroom, an exercise room and a stunning family room with a wall of built-ins and huge windows. This home offers a fenced, professionally landscaped yard and pond, along with an oversized two car garage. Well scaled rooms and nine foot ceilings create a generous sense of space and ease, while extensive millwork, coffered ceilings, and custom trim work reflect a level of craftsmanship rarely found in newer construction. Thoughtful finishes are woven throughout, warm and refined, resulting in interiors that are both livable and quietly elevated. All this in a fabulous tree street location just a few blocks to restaurants, shops, train and schools.

887 Ash Street, Winnetka
$899,000
3 Beds ⋅ 2 Baths ⋅ 12743165 MLS ⋅ CONTINGENT 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
$1,350,000
4 Beds ⋅ 3 Baths ⋅ 12732812 MLS ⋅ ACTIVE Status ⋅ Winnetka Mews BLDG.
Be prepared to be impressed by this rarely available, beautifully updated top-floor 4 bedroom, 3 bath residence in the historic Winnetka Mews, perfectly positioned with a Pine Street exposure. Thoughtfully renovated with exceptional attention to detail, this sun drenched home combines gracious living spaces, timeless finishes and an abundance of thoughtfully designed storage. At the heart of the home is a stunning chef's kitchen featuring custom cabinetry, a Wolf convection oven, Sub-Zero refrigerator, beverage refrigerator and striking granite countertops imported from India. The expansive living and dining rooms flow seamlessly together, creating an ideal setting for both everyday living and effortless entertaining. A custom marble fireplace anchors the space, while an exquisite chandelier imported from Sweden adds a distinctive finishing touch. The fourth bedroom is currently designed as an inviting library with custom built-in bookcases, offering wonderful flexibility as a home office, den or bedroom. The desirable Pine Street exposure fills the residence with natural light and offers peaceful treetop views along with a wonderful sense of privacy. All three bathrooms have been beautifully updated with Italian Carrara tile, medicine cabinets and RH plumbing fixtures. A feature rarely found in condominium living, is the custom mudroom with built-in lockers, providing additional storage and organization. Rich hardwood flooring extends throughout the main living spaces, while luxurious carpeting adds warmth and comfort to the bedrooms. Custom closets throughout further enhance the home's impressive storage. With four bedrooms, three full baths, generous entertaining spaces and a premier top-floor location, this is a rare opportunity to "right size" without compromise. Enjoy the space, quality and thoughtful design of a single-family home paired with the ease of condominium living, all just moments from downtown Winnetka, Lake Michigan beaches, Metra, boutique shopping, acclaimed restaurants and beautiful parks. Residents of Winnetka Mews enjoy an outdoor pool, fitness center, on-site management and a dedicated building engineer. Sophisticated, spacious and beautifully appointed, this exceptional residence offers an effortless lifestyle in one of Winnetka's most desirable locations.

640 Winnetka Mews Unit #403, Winnetka
$899,000
2 Beds ⋅ 2 Baths ⋅ 12604430 MLS ⋅ PENDING Status
Your perfect Winnetka lifestyle awaits! Grab a coffee from Hometown and walk to the beach, library, or jump on the Metra. Don't feel like cooking dinner? Head to one of the many great restaurants right in town. All are just steps away from this East Winnetka Gem. A pleasure to show, this entire condo was thoughtfully & beautifully renovated by Benvenuti and Stein with quality details and finishes throughout. A large foyer welcomes you with a coat closet adorned with solid core French doors. Glass French doors lead you to the expansive combined living & dining room complete with built in storage cabinets and display shelving. Entertain in the expanded eat in kitchen with breakfast bar island, custom maple cabinetry, Grohe chrome faucets, Miele dishwasher, double oven, Wolf induction cook top /with custom hood and exhaust to exterior, stainless steel appliances and gorgeous Cambria quartz counter tops. Relax after a long day in one of the freshly painted bedrooms, each with their own walk in closet(s). This large unit boasts its own laundry room equipped with a sink, custom cabinetry, countertop space for folding or extra supplies, storage shelving and Bosch washer/dryer. Two beautiful bathrooms are nicely appointed. One featuring a built in vanity, walk in shower & beautiful glass tile inlay. The second boasts a self cleaning / drying air tub and additional closet space. Engineered hardwood throughout main living areas & bedrooms. This third floor unit offers 48 inch wide hallways for ease of movement , pocket doors for maximum space and a newer 3 zoned HVAC system for your comfort in any room. Too many details to list, so much storage space! This one is a must see to appreciate! Heated garage parking (#13) and additional storage cage are easily accessible in this well maintained; 2 large scale elevator equipped building with an expansive back parking lot for your additional cars or guests. Recent building improvements include New roof 2026, New entry security intercom 2026, All halls/trim painted 2026, & Tuckpointing 25/26. A beautiful location and condo to call home! No rentals, No pets

711 Oak Street Unit #308, 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
$3,495,000
5 Beds ⋅ 8 Baths ⋅ 12672761 MLS ⋅ PENDING Status

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
$2,595,000
12213495 MLS ⋅ ACTIVE Status
Discover a once-in-a-lifetime opportunity to build your dream estate in one of the North Shore's most coveted neighborhoods. Situated on prestigious Woodley Road in Winnetka, this rarely available 1.45-acre property offers an extraordinary canvas for creating a truly exceptional residence. The existing home has already been demolished, leaving this premier homesite shovel-ready. Bring your own architect and builder, or take advantage of thoughtfully designed plans already in the final stages of the permitting process. With multiple PINs and over 63,000 square feet of land, the possibilities are endless. This property presents the rare opportunity to create a private estate with unparalleled scale, luxury, and privacy. Nestled among some of the North Shore's finest homes, the setting perfectly balances serene seclusion with everyday convenience. Located within the nationally acclaimed New Trier High School District, the property is just minutes from the boutiques, restaurants, and amenities of both Winnetka and Wilmette. Bring your vision and your grandest ideas to this remarkable offering.

61 Woodley Road, 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
$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
$2,675,000
5 Beds ⋅ 6 Baths ⋅ 12688601 MLS ⋅ PRICE CHANGE 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
$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
$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
$3,049,000
4 Beds ⋅ 5 Baths ⋅ 12693763 MLS ⋅ PENDING Status
Inspired by timeless French Eclectic architecture and impeccably built in 2007, this extraordinary residence offers an exceptional blend of architectural character, refined craftsmanship, and modern luxury. Ideally located just blocks from Lake Michigan, top-rated schools, parks, town, and train, the home sits on a beautifully landscaped lot designed for both elegant entertaining and everyday living. From the striking Stone and Limestone exterior and handsome front porch to the custom millwork, exquisite stonework, hardwood floors, and designer lighting throughout, every detail reflects thoughtful design and superior quality. Grand, light-filled living spaces include a chef's kitchen with premium finishes, a spacious family room, formal dining areas, and beautifully appointed private spaces ideal for work or relaxation. The luxurious primary suite is complemented by good sized secondary bedrooms and well-designed living areas across three finished levels. The fully finished lower level offers exceptional versatility with recreation spaces, an exercise room, additional bedroom suite, and spa-inspired amenities including a steam shower and dry sauna. Outdoors, professionally landscaped grounds create a private retreat featuring an inviting patio and lush lawn for seamless indoor-outdoor entertaining. Combining timeless architecture, exceptional craftsmanship, and an unparalleled location in one of the North Shore's most desirable neighborhoods, this remarkable home offers an extraordinary lifestyle defined by elegance, comfort, and enduring quality.

654 Pine Street, Winnetka
$2,785,000
6 Beds ⋅ 6 Baths ⋅ 12680099 MLS ⋅ ACTIVE Status
Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush, manicured grounds set the stage. Inside, the craftsmanship is unmistakable. You'll find expansive living spaces defined by rich architectural details and massive windows that frame the private, park-like backyard. The chef's kitchen is a masterpiece of function and style, flowing effortlessly into inviting family spaces that feel warm despite their scale. A first floor bedroom includes a private full bath and access to the patio. The primary suite serves as a genuine retreat, complete with a spa bath and enough closet space to satisfy any wardrobe. A sitting area surrounded by windows and a walkout overlooks the exquisite property. Each additional bedroom is en-suite and generously sized, ensuring everyone has their own corner of comfort. The third level includes flexible space with 3 lovely rooms and a full bath. There is an extra bonus space above the attached garage-perfect for a studio! Outside, the property truly shines. The expansive patio and rolling lawns create an incredible backdrop for summer garden parties or a quiet evening under the stars. Living here means more than just enjoying a beautiful residence; it's about the Winnetka lifestyle. You're minutes away from world-class schools, boutique shopping in the village, the shores of Lake Michigan, and the Metra for an easy commute to the city. It's sophisticated, it's private, and it's ready for its next chapter.

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

319 Sheridan Road, Winnetka
$2,250,000
4 Beds ⋅ 6 Baths ⋅ 12673083 MLS ⋅ ACTIVE Status
Rarely available first floor primary! Unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners. Owner extremely motivated!!!

42 Woodley Road, Winnetka



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