Browse All Winnetka IL 4 Bedroom Properties for Sale

4 Beds ⋅ 5 Baths ⋅ 12706253 MLS ⋅ NEW Status

Winnetka

4 Beds ⋅ 3 Baths ⋅ 12705964 MLS ⋅ NEW Status

Winnetka

4 Beds ⋅ 2 Baths ⋅ 12684251 MLS ⋅ ACTIVE Status

This 4-Bedrm and 2-Bath Cottage style home sits on a 5,267 Sq Ft lot in coveted Winnetka Hubbard Woods. This property located in top -rated schools (Hubbard Elementary) presents potential to renovate, expand or reimagine in a premier North Shore setting. The main floor plan unveils an open concept with a sprawling Family room filled with natural light next to separate sitting room with a gorgeous brick fireplace and hinged French doors to a formal Dining Room. A generous size kitchen finished with 36" cabinetry with glass facade accents, stainless steel appliances. Two good size bedrooms with a shared full bathroom between and a room as a separate office. Hardwood floors throughout. The second floor has 2 bedrooms and a loft. Full unfinished lower level with a half bathroom. Private fenced in yard and plenty of parking. Close to Metra, downtown Winnetka, Lake Michigan, parks, trails, shopping and MORE *** Sellers motivated.

979 Vine Street, Winnetka

$1,500,000

4 Beds ⋅ 3 Baths ⋅ 12699325 MLS ⋅ ACTIVE 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

$1,799,000

4 Beds ⋅ 3 Baths ⋅ 12704826 MLS ⋅ CONTINGENT Status

Exceptional 4-bedroom, 2.1-bath home on Winnetka's coveted Tree Streets, offering an expansive third-floor loft and situated on a 50' x 187' deep lot. Blending timeless charm with thoughtfully designed living spaces, this home is filled with natural light, soaring ceilings, and beautiful hardwood floors throughout. A welcoming covered front porch leads into gracious living and dining rooms, while the attached extra-deep 2-car garage comfortably accommodates a full-size SUV suburban with direct access to a mudroom and powder room. Designed for both entertaining and daily living, the impressive chef's kitchen features sleek cabinetry, granite countertops, exceptional storage, an oversized island, separate breakfast bar, stainless steel appliances, double ovens, beverage refrigerator, and a sunny breakfast area overlooking the spectacular backyard. The adjacent family room is warm and inviting with custom built-ins, a wood-burning fireplace, and French doors opening to the deck, creating seamless indoor-outdoor living. Upstairs, you'll find four spacious bedrooms, including a stunning primary suite with soaring vaulted ceilings, two walk-in closets, and a beautifully updated spa-inspired bath featuring heated floors, dual vanities, a skylight, soaking tub, and a separate glass-enclosed shower. A private staircase leads to the extraordinary third-floor, complete with a wet bar and offering incredible flexibility as a luxurious primary retreat, home office, or private fitness studio. Vaulted ceilings, skylights, and abundant natural light make this one of the home's most unforgettable spaces. The finished basement provides even more flexible living space with a large recreation room, laundry room, and storage. Additional highlights include dual-zone heating and cooling, a deep attached garage, and a beautifully landscaped, fully fenced backyard with a spacious deck ideal for entertaining, relaxing, and play. All of this is just moments from Crow Island School, parks, downtown Winnetka's shops and restaurants, and the Metra, offering the perfect combination of space, style, and an unbeatable location.

922 Ash Street, Winnetka

$2,699,000

4 Beds ⋅ 6 Baths ⋅ 12690581 MLS ⋅ CONTINGENT Status

Winnetka! This checks all of the boxes! 5 Beds/5.1 Baths. This gorgeous SFH comes with all of the perks. Gourmet kitchen with Sub-Zero/Thermador, large island, walk-in pantry and gorgeous breakfast area that opens to the family room. The first floor office has built-ins and French doors. Step into the formal dining room with beautiful ceiling details and moldings. Relax in the formal living room in front of the fireplace. Incredible primary suite with large his-and-her closets, and luxurious bath. The second floor has 2 additional ensuite bedrooms and a nicely appointed laundry room. The 3rd floor is light-filled and offers a 4th ensuite bedroom. The fantastic lower level has it all: a huge recreation room, 5th bedroom, exercise/theatre room, wine room, golf simulator, and the 5th full bath. Great location near schools, tennis, golf, playfields, and the train. Experience everything Winnetka has to offer.

1050 Spruce Street, Winnetka

$2,899,000

4 Beds ⋅ 4 Baths ⋅ 12688378 MLS ⋅ CONTINGENT Status

792 Walden Road, Winnetka

$3,799,000

4 Beds ⋅ 5 Baths ⋅ 12688040 MLS ⋅ CONTINGENT Status

785 Mount Pleasant Street, 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

$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

$1,795,000

4 Beds ⋅ 4 Baths ⋅ 12678232 MLS ⋅ CONTINGENT Status

Located in the heart of Winnetka and within the highly sought-after Crow Island School District, this impeccably maintained 5-bedroom, 3.1-bath home checks every box. Thoughtfully reimagined and beautifully updated, the first floor offers exceptional flow, abundant natural light and timeless finishes throughout. At the center of the home is the stunning kitchen, completely gutted and renovated in 2022 with top-of-the-line finishes and a thoughtful design. A large island serves as the heart of the kitchen and gathering space, while the chef's appliances and custom high-end cabinetry make it as functional as it is beautiful. The kitchen opens seamlessly to the family room, creating the perfect space for everyday living and entertaining. The screened porch offers great indoor/outdoor living. The first floor also features a gracious dining room, inviting living room, refreshed mudroom, stylish powder room, and exceptional custom millwork throughout. Upstairs, you'll find four spacious bedrooms and two full baths. The oversized primary suite has generous closet space and a beautifully appointed bath featuring dual vanities, a separate shower, and soaking tub. Three additional bedrooms are bright and airy, each with custom closet organizers. The lower level was largely renovated in 2023 and offers incredible additional living space with updated flooring, lighting, drywall, and expanded recreation areas. A fifth bedroom and full bath provide the perfect accommodations for guests, an au pair, or a private home office. The backyard offers great space for entertaining, kids playing and sunshine. The garage is oversized (2.5 spaces) and has extra depth for those suburban mom SUVs. Meticulously maintained and move-in ready, this exceptional home is ideally located just steps from town, train, parks, schools, and everything that makes Winnetka one of the North Shore's most desirable communities.

1037 Oak Street, Winnetka

$1,495,000

4 Beds ⋅ 4 Baths ⋅ 12688534 MLS ⋅ CONTINGENT Status

Set on a professionally landscaped half-acre in the coveted Hubbard Woods School District, this exceptional 4-bedroom, 3.1-bath home offers expansive living spaces, refined finishes, and an effortless floor plan. A gracious foyer opens to an elegant circular layout featuring a sun-filled living room anchored by a striking fireplace, a handsome private office overlooking the landscaped grounds, and a sophisticated dining room with doors opening to the bluestone patio. The inviting family room enjoys picturesque views of the garden-like front lawn and flows seamlessly into the expansive eat-in kitchen, complete with a generous island, high-end appliances, and sweeping views of the lush backyard. A butler's pantry, spacious mudroom, and attached two-car garage complete the thoughtfully designed main level. Upstairs, two luxurious primary suites are complemented by two oversized secondary bedrooms, abundant closet space, and exceptional flexibility. The finished lower level offers a spacious recreation room, dedicated craft studio, and extensive storage. Walk to schools, town, tennis courts and the Winnetka Golf Course!

1347 Sunview Lane, Winnetka

$1,495,000

4 Beds ⋅ 3 Baths ⋅ 12687072 MLS ⋅ ACTIVE 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 agent is related to the seller.

1110 Elm Street, Winnetka

$1,399,000

4 Beds ⋅ 4 Baths ⋅ 12657695 MLS ⋅ PENDING Status

Privately tucked on an extra wide 1/3rd acre property, this fully re-imagined mid-century modern home offers exceptional design and incredible vistas of its lushly landscaped property. Thoughtfully curated with attention to detail and a sophisticated eye for design, the home blends timeless architecture with abundant natural beauty, right in the heart of Winnetka. A super chic, modern kitchen with abundant custom cabinetry and top-tier appliances is anchored by a large island and opens to a stunning dining room with radiant-heated floors and walls of windows beautifully framing panoramic views of the verdant property. The stylized mid-century living room features a contemporary gas fireplace and overlooks the professionally landscaped grounds, perennial gardens, and brick patio. The inviting family room, complete with radiant-heated floors and a second fireplace, offers a warm and stylish gathering place. The luxurious primary suite is a true sanctuary, featuring a private sitting room with built-ins, custom closets, and a spa-inspired bath. Three additional generously sized bedrooms - one ensuite and two sharing a hall bath - provide beautifully appointed modern accommodations for family and guests. The large rec room offers plenty of space for lounging, a work-out area and/or game area, plus a separate laundry room and access to the attached and heated 2-car garage. Every detail of this home has been thoughtfully re-imagined to create effortless indoor-outdoor living. Enjoy an intentional, design-forward home surrounded by beautiful grounds with blooming gardens, and located within easy walking distance to town, schools, parks, the A.C. Nielsen Tennis Center, the Winnetka Golf Club, and the Skokie Lagoons.

1225 Elm Street, Winnetka

$975,000

4 Beds ⋅ 4 Baths ⋅ 12617031 MLS ⋅ CONTINGENT Status

Prepare to be captivated by this picture-perfect 4-bedroom, 3.1-bathroom colonial-cottage home, meticulously updated with high-end designer finishes throughout. Boasting incredible curb appeal with its deep blue siding, crisp white trim, and brick-paver paths, this turn-key residence seamlessly blends historic architectural character with contemporary luxury. Inside, an airy, light-filled layout features pristine hardwood flooring, clean architectural lines, and an adaptable floor plan. The heart of the home is the stunning new kitchen, showcasing custom sage-green shaker cabinetry, durable stone countertops, a timeless white farmhouse sink, and high-efficiency stainless steel appliances. The kitchen overlooks the rear living space, where sliding glass doors offer a clear view and effortless access to the private rear entertainment deck. The upper levels house a spectacular primary retreat, designed as a private sanctuary. The primary bathroom offers a true spa experience with its freestanding soaking tub, walk-in shower, expansive double vanity, and a massive skylight overhead. The remaining three bedrooms feature charming sloped cottage ceilings, bright windows, and classic millwork. A second beautifully renovated hall bath showcases a sophisticated, moody color palette, a premium marble vanity, and an integrated skylight. Additional living and recreation space awaits in the finished lower level, anchored by a cozy electric fireplace is ideal for a family room, home theater, or private office. The laundry room, a wine closet, an enormous storage room, third fill bathroom and a craft room round out the flexible basement level. Outside, enjoy a detached 1-car garage and low-maintenance landscaping. Nestled in a premier neighborhood, this home offers unparalleled convenience with its close proximity to town, the train, and local schools. A masterful combination of sophisticated design and everyday functionality!

882 Willow Road, Winnetka

$2,250,000

4 Beds ⋅ 6 Baths ⋅ 12673083 MLS ⋅ ACTIVE Status

Rarely available 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.

42 Woodley Road, Winnetka

$1,700,000

4 Beds ⋅ 4 Baths ⋅ 12629591 MLS ⋅ PENDING Status

They don't build them like this anymore, but they should! This solidly built custom Hemphill home is ideally located in sought-after East Winnetka and offers timeless character, quality craftsmanship, and thoughtful updates. Built in 1936 with exceptional materials and lovingly maintained by only two owners, this home combines classic elegance with modern comfort. The spacious living room features decorative plaster crown molding, a gas-log fireplace, and built-in cabinetry, while the formal dining room showcases equally impressive molding and elegant wainscoting. The kitchen is appointed with high-end appliances, beautiful wood cabinetry, granite countertops, and an eating area. A welcoming family room overlooks the expansive fenced backyard and slate patio. Upstairs, four generously sized bedrooms each offer walk-in closets. The second level also includes an updated primary bath, a hall bath, and an en-suite bath, along with a large cedar closet and a deck overlooking the backyard. The basement offers exceptional additional space with four separate rooms: a recreation room with wood-burning fireplace, a work/hobby room, a "canning"/storage room, and a utility area with laundry. Direct access to the oversized attached two-car garage adds convenience. Set on a wide lot, 478 Sunset offers a wonderful floor plan just a few blocks from parks, schools, beaches, the train, and more.

478 Sunset Road, Winnetka

$2,695,000

4 Beds ⋅ 5 Baths ⋅ 12620950 MLS ⋅ PENDING Status

This incredible & expansive 4 bedroom, 3.2 bathroom home is situated on a spectacular property in an idyllic & private location. Surrounded by mature trees and beautiful foliage, the fantastic gardens & outdoor area boast three bluestone patios. The home brings the outdoors inside with oversized windows throughout the home. When you walk into the home, you are welcomed in the large foyer and move into the living room with marble surround fireplace that is sun-filled and bright. This leads you to the enclosed porch area where you can bask in the sun with walls of windows & surrounded by private, beautiful and mature landscaping. This home truly brings the outdoors inside to you! The dining room is perfect for hosting events and leads to the white eat-in kitchen with an island and double ovens that is very spacious for cooking and entertaining. The kitchen is conveniently located next to the first-floor laundry room. Down the hall from the kitchen is a huge wood beamed ceiling family room with patio doors that open to the outside, a fireplace with granite surround and built-in bookshelves where the media resides. The octagonal office with an oversized vaulted ceiling and is flanked with floor to ceiling windows and beautiful built-in bookshelves. Working from home has never been more relaxing in this serene setting. Take the steps off the family room up to the recreation room where you can play pool, games or watch tv in this amazing playroom area. The functionality of having a large first floor primary suite, with attached bathroom, closets galore, near your own outdoor oasis is spectacular. You are in your own bed and breakfast when sleeping in the first-floor primary suite retreat surrounded by gardens and a bluestone walkway. The second floor has three additional bedrooms and two full bathrooms. With an attached 3 car garage, circular driveway on the property and parking for guests in front of the home, you are ready to host any event at this incredible home. The lower level has storage galore and a wine cellar. This is a very special home that has been well loved for many years on the most incredible and expansive property.

92 Indian Hill Road, Winnetka

$2,799,388

4 Beds ⋅ 6 Baths ⋅ 12573223 MLS ⋅ PENDING Status

510 Provident Avenue, Winnetka

Start Your Search

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

Copyright 2026 MRED LLC. All rights reserved.

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

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

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

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

Some listings have been excluded from this website.

4 Bedroom Winnetka Real Estate

Our website features the best real estate search for 4 bedroom properties available in Winnetka and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

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

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

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