Winnetka (WIN) Homes with Three Or More Levels Stories

Welcome to Winnetka, California – a hidden gem nestled in the vibrant landscape of Los Angeles County. This charming neighborhood seamlessly blends suburban tranquility with urban accessibility, making it an ideal choice for families, young professionals, and anyone seeking a welcoming community. With its tree-lined streets, well-maintained parks, and a variety of local amenities, Winnetka offers a delightful lifestyle that feels both peaceful and connected.

One of the standout features of homes in Winnetka is their architectural diversity, particularly the availability of stunning residences with three or more levels. These multi-story homes provide an abundance of space and versatility, perfect for modern living. Whether you’re looking for a spacious family home with multiple bedrooms and bathrooms or a stylish retreat with room for entertaining, Winnetka's three-level properties deliver on both style and functionality.

Imagine waking up in a beautifully designed home that offers panoramic views from the upper levels, or hosting gatherings in your expansive living area that flows seamlessly into a well-appointed kitchen. With ample space for a home office, guest rooms, or even a cozy reading nook, these homes cater to a variety of lifestyle needs.

Winnetka is also conveniently located near major highways, making commutes to nearby hubs like the San Fernando Valley and downtown Los Angeles a breeze. With a blend of community spirit, accessibility, and stunning multi-level homes, Winnetka is not just a place to live; it’s a place to thrive. Explore the possibilities that await you in this enchanting neighborhood and discover your dream home today!

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

$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

$519,900

3 Beds ⋅ 4 Baths ⋅ 226003140 MLS ⋅ Active Under Contract Status

Architecturally distinctive and filled with natural light, this 3-bedroom, 3.5-bath gated end-unit townhome offers approximately 1,860 square feet of thoughtfully designed living space in a desirable gated Winnetka community. Featuring two spacious primary suites, a distinctive split-level floor plan, soaring vaulted ceilings, and versatile living spaces, this residence offers the openness and functionality often associated with a detached home. A private gated front patio welcomes you to the entry, where a solid wood front door opens to an inviting interior. The spacious living room makes an immediate impression with dramatic vaulted ceilings, an architectural overlook to the upper level, a cozy fireplace, and sliding glass doors opening to a private balcony, creating an open and airy atmosphere ideal for relaxing or entertaining. The adjoining dining area is bathed in natural light from oversized windows and is highlighted by a contemporary light fixture. The adjacent kitchen is designed for both style and function, offering granite countertops, extensive cabinetry, a breakfast bar, recessed lighting, a decorative tile backsplash, stainless steel appliances, and generous workspace for everyday living. The split-level design provides excellent separation between gathering spaces and private retreats while maintaining an open, connected feel throughout the home. The upper level features two generously sized primary suites, each with vaulted ceilings, bamboo flooring, generous closet space, and private en-suite bathrooms. One suite includes a walk-in closet, private balcony, and an updated bathroom with granite countertops, a stone tile tub and shower surround, and a glass enclosure. The second suite also offers an updated en-suite bathroom with granite countertops and a beautifully tiled shower, creating an ideal layout for multi-generational living, guests, roommates, or today's work-from-home lifestyle. The lower level features a spacious third bedroom with an adjacent three-quarter bathroom, offering exceptional flexibility for guests, a home office, fitness room, media room, or creative studio. Additional highlights include bamboo flooring throughout the upper level, tile flooring throughout the main living areas, central heating and air conditioning, an indoor laundry area, abundant storage, a direct-access two-car garage, and multiple private balconies that extend the living spaces outdoors. Residents enjoy beautifully maintained grounds, a sparkling community pool, relaxing spa, clubhouse, guest parking, and a secured gated entrance, all conveniently located near shopping, dining, parks, schools, public transportation, Pierce College, Westfield Topanga, Topanga Village, Warner Center, and convenient freeway access. Offering architectural character, dual primary suites, a highly functional floor plan, desirable community amenities, and a prime Winnetka location, this exceptional end-unit residence presents a rare opportunity to enjoy comfortable, low-maintenance living.

19950 Sherman Way Unit A, 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

$655,000

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.