Winnetka (WIN) Homes with Three Or More Levels Stories

Welcome to Winnetka, California – a charming neighborhood nestled in the heart of Los Angeles County, where suburban tranquility meets urban convenience. Known for its warm community spirit and family-friendly atmosphere, Winnetka offers a delightful blend of residential comfort and vibrant local amenities. With its tree-lined streets, parks, and close-knit community, it’s no wonder that many families and professionals are drawn to this enchanting area.

Winnetka boasts a diverse range of homes, including the unique and spacious properties with three or more levels. These multi-story homes provide an abundance of living space, making them ideal for families seeking room to grow or those who simply enjoy the luxury of expansive living. Imagine waking up to breathtaking views from your upper-level master suite or entertaining guests in a stylishly designed rooftop terrace. The added levels not only enhance the aesthetic appeal of these homes but also offer practical solutions for modern living, with dedicated spaces for work, play, and relaxation.

Beyond the homes, residents of Winnetka enjoy access to a variety of parks, recreational facilities, and shopping destinations. The community is well-connected by public transport and major highways, making it easy to explore the greater Los Angeles area. Whether you’re drawn to the allure of a multi-story home or the welcoming vibe of the neighborhood, Winnetka is a hidden gem waiting to be discovered. Come experience the perfect blend of comfort and convenience in this delightful Los Angeles enclave!

Newest Winnetka (WIN) Homes with Three Or More Levels Stories

$379,000

1 Beds ⋅ 1 Baths ⋅ 26869727 MLS ⋅ Active Status

Charming 1 Bedroom condominium featuring plenty of natural light, bright large size of 744 square foot, a tastefully updated bathroom and a recently updated kitchen and with two tandem parking spaces. Better check this out! This home offers a cozy and restful living space, making it a paradigm choice for first-time home buyers, young people, those looking for a convenient living arrangement in the heart of Los Angeles or an investment property. An attractively updated bathroom, and kitchen with modernized cabinets. The kitchen comes with new stainless appliances such as refrigerator, dishwash, and oven. A new paint job throughout the whole unit, a good amount of space in the storage room, and suitable balcony too. A beneficial size walk-in closet that gives more storage space. The elegant condominium is perfect for those who want to take advantage of the city's vivid lifestyle, cultural scene, and energetic entertainment options. The community also features an original pool for relaxation, a well-equipped gym for fitness, and polished recreation room for social gatherings. Improve and enjoy your life in this beautiful unit and community performances. Located within minutes of The Orange Line, the Topanga Westfield Shopping Center, and a few local restaurants too. Check this stunning condo for a first investment property or your first sweet home today!

20234 Cantara Street Unit 229, Winnetka

$899,950

4 Beds ⋅ 3 Baths ⋅ OC26159383 MLS ⋅ Active Status

Welcome to 20259 Gifford St, a beautifully maintained split-level home in the heart of Winnetka offering 4 bedrooms, 3 bathrooms, a dedicated office or possible 5th bedroom, and 2,395 sqft of spacious, light-filled living space on a 5,202 sqft lot. Thoughtfully updated throughout, this inviting home blends generous living areas with modern finishes and a highly functional floor plan designed for both everyday living and entertaining. Rich flooring, recessed lighting, crown molding, and an abundance of natural light create a warm, move-in ready atmosphere from the moment you step inside. The main living spaces offer exceptional flexibility with multiple gathering areas, including an expansive living room, a separate family room anchored by a cozy fireplace, and a formal dining area that flows seamlessly into the beautifully updated kitchen. The kitchen is a true centerpiece featuring granite countertops, crisp white cabinetry, stainless steel appliances, an oversized breakfast bar, and ample cabinet and prep space, making it ideal for everything from casual mornings to hosting family and friends. A dedicated office provides the perfect work-from-home space, study, hobby room, or fitness area. The spacious primary suite offers a peaceful retreat with generous proportions and an updated en-suite bathroom, while three additional bedrooms and well-appointed bathrooms provide comfortable accommodations for family and guests. A newer HVAC system ensures year-round comfort and keeps the home cool during warm San Fernando Valley summers, while the attached garage includes an EV charger for added convenience. Outside, you'll find charming curb appeal with a fully fenced front yard highlighted by mature landscaping and colorful rose gardens, creating a welcoming first impression. The private backyard features a large patio, elevated deck, and plenty of room for outdoor dining, entertaining, gardening, or simply relaxing in your own outdoor retreat. Tucked between Northridge, Canoga Park, and West Hills, minutes to Westfield Topanga, The Village, Pierce College, CSUN, and the 101 / 118 / 405. LAUSD with magnet and charter options. FHA, VA, and conventional financing all welcome. Call your Realtor to schedule a tour and make an offer today! Welcome home!

20259 Gifford, Winnetka

$345,000

1 Beds ⋅ 1 Baths ⋅ SR26149183 MLS ⋅ Active Status

Condo in the City of Winnetka sounds like a Great Opportunity for a New Owner or Investor looking for Passive Rental Income. Come and Make this your Home. This Condo is has been Recently Remolded and is Turnkey Ready and it's in the City of Winnetka; just waiting for You! Secured Lobby Entrance; providing an added level of safety and security. This beautifully Well Maintained Unit Features; Spacious One Bedrooms, One Bathrooms; providing ample living space for residents, a Walk-in Closet, Plenty of Storage Space, Kitchen Granite Counter Tops, Stainless Steel Appliances including; Stove Range, an Over Range Microwave, and a Refrigerator, Dining Area with an Open Floorplan Leading into the Livingroom, along with Laminated, and Tile Flooring; combining aesthetics and easy maintenance. , Your Own Central HVAC System, Two Tandem Assigned Parking Spots, and Very Low HOA including; Trash, Water, Insurance, and Sewer. This Condo Complex offers a Community Pool, Spa, BBQ Area, and laundry room Area. Centrally Located on the Westside of the San Fernando Valley, and only minutes away from the Orange Line, Warner Center, Future Ram Headquarters, Topanga Mall, The Village at Westfield Topanga, Shopping Centers, and more! Come and Schedule your Private Viewing.

20327 Saticoy Unit 309, Winnetka

$645,000

3 Beds ⋅ 4 Baths ⋅ OC26127703 MLS ⋅ Active Status

This highly desireable Townhome has been freshly painted, includes a smart Frig, Thermostat, $8,000 of custom drapes, and a fantastic location for quick commuting through out LA. 3 bedrooms, 2 full bathrooms upstairs, 1 - 3/4 bathroom downstairs, and 1 half bath on the main floor. Nice wood floors, carpet, and tile on the main floor. Seller is getting bid/price for new carpet on the stairs and upstairs hall way. Nice garage entry on the 1st floor with laundry and a bedroom on this floor. Upstairs are 2 large bedrooms, a primary with a walkin closet, and soaking tub. The other bedroom is also oversized and has an attached full bathroom. The community has a nice club house, pool, and spa just two building away. Gated for security.

19932 Sherman Way Unit B, Winnetka

$250,000

1 Baths ⋅ SR26119063 MLS ⋅ Active Status

This is perhaps the lowest price point for entry in the area today, you can be a homeowner in the valley.Very Important-this is by appointment only you must call the listing agent in order to show, please do not disturb tenant or go to the unit without an appointment first.

20234 Cantara Unit 342, Winnetka

$647,000

3 Beds ⋅ 3 Baths ⋅ SW26096401 MLS ⋅ Active Status

Welcome to Sherman Courts — One of Winnetka's Most Sought-After Gated Communities This stunning multi-level townhome offers the perfect blend of space, style, and resort-style living in the heart of the San Fernando Valley. Situated as a corner unit with only one shared wall, this home lives large with an open, airy feel and natural light pouring in from multiple directions. Spread across three levels, the thoughtfully designed floor plan offers incredible flexibility. The lower level features a generous bonus room perfect as a third bedroom, home office, media room, or gym — a true flex space that adapts to your lifestyle. The main level is made for entertaining, anchored by a warm and inviting family room with a gorgeous red brick fireplace. The open living and dining area features a wet bar and flows seamlessly to a private patio — the perfect spot to relax or dine al fresco in Southern California's year-round sunshine. The beautifully appointed kitchen boasts granite countertops and stainless steel appliances, making it as functional as it is stylish. The upper level is home to the spacious primary suite with a private bath, his-and-hers closets, and a private balcony, plus an additional bedroom and a versatile loft — ideal as a home office, playroom, creative retreat, or 4th bedroom. Updated bathrooms throughout and new flooring add a fresh, modern finish at every turn. The attached direct-access 2-car garage includes washer and dryer hookups for everyday convenience, plus ample storage. An additional reserved parking spot is also included — a rare bonus. Sherman Courts is a beautifully maintained gated community featuring a sparkling pool, spa, lighted tennis courts, and picnic area. A true resort-style living steps from your front door. HOA dues of $485/month cover water, trash, exterior structural insurance, roof maintenance, and 1 reserved parking space. Located in the heart of Winnetka just 25 miles northwest of downtown Los Angeles, residents enjoy easy access to top shopping, diverse dining, parks, Pierce College, Cal State Northridge, and major commuter routes. 1,843 sq ft | 3 Bed + Loft | 2.5 Bath | 2-Car Garage + Reserved Parking | Gated Community Spacious. Stylish. Move-in ready. This is the one.

20224 Sherman Unit 48, Winnetka

$420,000

2 Beds ⋅ 2 Baths ⋅ WS26073035 MLS ⋅ Active Status

First Team Real Estate welcomes you home to your private retreat in the heart of Winnetka. Tucked inside a beautifully maintained gated community, this charming 2-bedroom, 2-bathroom corner-unit condominium located on the third floor offers the perfect blend of comfort, convenience, and everyday enjoyment. This desirable corner location provides added privacy, pleasant views, and an abundance of natural light throughout. The property is currently tenant-occupied by a responsible and well-maintaining tenant who has taken excellent care of the home, making it an attractive opportunity for both investors and future homeowners. Imagine starting your mornings on your private balcony, enjoying a cup of coffee as the day begins, or unwinding in the evening in your serene living space, away from the noise of the street below. The thoughtfully designed layout features an open-concept kitchen that flows seamlessly into the living and dining areas, enhanced by higher ceilings that create an airy and inviting atmosphere. The primary suite includes its own private ensuite bathroom, while the second bedroom offers versatility—ideal for guests, a home office, or additional living space. The home also features convenient in-unit stackable laundry. The community invites you to relax and recharge with amenities including a sparkling pool and Jacuzzi—perfect for weekends or casual gatherings. With gated parking, elevator access, a furnished lobby, and well-maintained grounds, every detail is designed to make daily living effortless. Whether you are a first-time buyer searching for a place to call your own or an investor seeking a well-maintained property in a desirable location, this home presents an incredible opportunity. Ideally situated near shopping, dining, and major freeways, everything you need is just moments away. This isn’t just a condominium—it’s a place to truly feel at home.

7640 Oso Unit 318, Winnetka

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Based on information from California Regional Multiple Listing Service, Inc. as of . This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.