Browse All Winnetka IL 3 Bedroom Properties for Sale

3 Beds ⋅ 5 Baths ⋅ 12715536 MLS ⋅ NEW 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

$999,000

3 Beds ⋅ 3 Baths ⋅ 12711054 MLS ⋅ CONTINGENT Status

Winnetka "tree streets" gem! This fully updated home blends classic exterior charm with a modern, open layout! Featuring three bedrooms, two and a half baths, a gorgeous kitchen and a beautiful backyard. Huge living room anchored by pretty fireplace flows seamlessly into open newer white kitchen and dining area. Family room - located just off the kitchen - opens to a fully fenced backyard with nice paver patio - and separate patio for grilling. Thoughtful mudroom area, powder room, and entry round out the first floor. The second floor features a large primary suite with two closets and a renovated primary bath. Two more family bedrooms share updated hall bath. Full basement with finished recreation room, laundry room, and huge storage room. Pull down stair attic has tons of additional storage or potential for future expansion. Deep, fully fenced yard with patio provides the perfect retreat. Detached two car garage with built in shelves. Unbeatable location: walk to top-rated schools, the Winnetka train, and all downtown Winnetka has to offer!

419 Provident Avenue, Winnetka

$1,795,000

3 Beds ⋅ 3 Baths ⋅ 12698922 MLS ⋅ ACTIVE 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

$950,000

3 Beds ⋅ 2 Baths ⋅ 12697250 MLS ⋅ CONTINGENT Status

Rare opportunity in East Winnetka. Nestled beside a quiet neighborhood park, this beautifully updated 1919 Tudor blends timeless architectural character with thoughtful modern updates in one of Winnetka's most sought-after locations. A scenic path just behind the home provides easy access to the Green Bay Trail, making it an easy walk or bike ride to Hubbard Woods School, the Metra, and downtown Hubbard Woods. From the moment you step inside, you'll appreciate the abundance of natural light streaming through white Marvin windows, creating bright, inviting living spaces throughout. The welcoming living room centers around a fireplace, while the renovated kitchen with newer quartz countertops opens seamlessly to the spacious family and dining rooms. A dramatic wall of windows and door opens to the professionally landscaped backyard and patio, creating an ideal setting for both everyday living and entertaining. The second floor offers three generously sized bedrooms and a beautifully renovated marble hall bath completed in 2021, while an updated full bath on the main level provides added convenience for guests. The freshly painted basement offers flexible space for a home gym, playroom, or additional storage. Extensive recent improvements make this home truly move-in ready, including refinished hardwood floors, fresh interior and exterior paint, and numerous cosmetic updates completed in 2025. Buyers will also appreciate the peace of mind that comes with a complete tear-off roof and HVAC system installed in 2016, along with exterior tuckpointing of both the home and chimney completed in 2023. Outside, the professionally landscaped yard is filled with mature trees and seasonal blooms, creating exceptional curb appeal and year-round beauty. There is also the potential to add a detached garage or porte cochere (buyer to verify with the Village). Low real estate taxes and the unique benefit of access to both the Winnetka and Glencoe Park Districts add even more value to this exceptional offering. Everything you love about East Winnetka is just moments away-from Hubbard Woods School, the Metra, downtown Hubbard Woods, Tower Road Beach, and the Green Bay Trail just steps from your back door-making this a home you'll enjoy from day one.

154 Glenwood Avenue, Winnetka

$1,195,000

3 Beds ⋅ 2 Baths ⋅ 12604512 MLS ⋅ CONTINGENT Status

Nestled in the heart of Winnetka's coveted " TREE STREETS" neighborhood sits the storybook home you've been waiting for. This special home is a sun-filled Mediterranean villa with an effortless blend of timeless architecture and a fresh, coastal-inspired aesthetic throughout. The home showcases airy interiors, soft neutral tones, and a well appointed floor plan that perfectly suits today's lifestyle. The great room has soaring ceilings, white washed wood beams, windows overlooking the park and a cozy gas fireplace. The bright white kitchen has high end appliances and beautiful marble countertops. The dining room is conveniently located adjacent to the kitchen. The first floor primary suite was recently expanded to create a spacious beautiful space. Equipped with a spa-like bathroom and large walk-in closet. The second floor has a bright landing desk/reading area, two large bedrooms connected by a beautiful bathroom, as well as a sun-filled bonus tandem room overlooking the gorgeous yard. The finished basement is currently being used as a music room but can easily be whatever you desire for the space. The tranquil oversized backyard is a peaceful place to retreat. Lush and green with a large bluestone patio, fire-pit and grill area, all with perfect views of the Fourth of July fireworks! Enjoy easy living with the premier walk-to location-just steps to award winning schools K-8, tennis, paddle, golf, sports fields, town + train and a short walk to the beach. Drop your bags & enjoy!!

1208 Oak Street, Winnetka

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