Winnetka (WIN) Homes with Multi Level Stories

Welcome to Winnetka, California – a hidden gem nestled in the heart of Los Angeles County. Known for its vibrant community and family-friendly atmosphere, Winnetka offers a perfect blend of suburban charm and urban convenience. With tree-lined streets, lush parks, and an array of local shops and eateries, this neighborhood is ideal for those seeking a tranquil lifestyle without sacrificing access to the excitement of the city.

Winnetka is particularly renowned for its diverse housing options, including stunning multi-level homes that cater to a variety of lifestyles. These multi-story residences not only provide ample living space but also offer unique architectural designs that stand out in the neighborhood. Imagine waking up to breathtaking views from your master suite or hosting family gatherings in spacious living areas that seamlessly flow from one level to another.

The multi-level homes in Winnetka are perfect for families, providing individual space for everyone while fostering togetherness in shared areas. With modern amenities and thoughtful layouts, these homes are designed for comfort and functionality. Whether you’re looking for a cozy retreat or an entertainer’s paradise, Winnetka’s multi-level properties present endless possibilities.

In addition to the beautiful homes, residents enjoy easy access to local parks, schools, and recreational facilities. The community spirit is palpable, with numerous events and activities that bring neighbors together. If you’re searching for a vibrant neighborhood with stunning multi-level homes, look no further than Winnetka – where your dream home awaits!

Newest Winnetka (WIN) Homes with Multi Level Stories

$1,499,999

6 Beds ⋅ 6 Baths ⋅ 26862297 MLS ⋅ Active Status

Beautiful updated home with rental property income. First property is a 3 bedroom 2 bath 1225 sqft with private backyard. Garage has been converted into JR ADU with full kitchen, bathroom and laundry. The second free standing unit is a brand new 2 story ADU just finished in the back with private access and private backyard. The newly built ADU features an open floor, high ceilings 2 bedroom, 2 and a half bathrooms with laundry unit inside as well with a 1200 sqft open floor plan. All units have with tankless water heaters installed. PAID OFF SOLAR PANELS. This property also has 2 power meters and 3 addresses. Everything is permitted, buyer to verify with local building and safety office.

6915 Laramie Avenue, Winnetka

$1,465,000

10 Beds ⋅ 6 Baths ⋅ 26853711 MLS ⋅ Active Status

6-Unit multifamily in the heart of Winnetka one of the San Fernando Valley's most sought-after rental markets. Situated on a 7,412 SF lot with 4,800 SF of rentable space, the property offers a strong unit mix of four 2BD/1BA and two 1BD/1BA units averaging 800 SF each. One unit delivered vacant at close, with approximately 38% rental upside across the remaining five. The detached garage presents additional ADU potential, giving a new owner multiple paths to maximize income and long-term value. Ideally positioned near Canoga Park and Woodland Hills with convenient access to major employment, shopping, and dining throughout the West Valley.

20542 Hartland Street Unit 2, Winnetka

$330,000

1 Beds ⋅ 1 Baths ⋅ 26843921 MLS ⋅ Active Under Contract Status

ALL APPLIANCES INCLUDED. Charming and move-in ready 1-bedroom, 1-bath condominium featuring 630 sq. ft. of comfortable living space. This home boasts high ceilings, a cozy fireplace, and an outdoor patio, creating a bright and inviting atmosphere. Enjoy a well-appointed kitchen, spacious living area, and the convenience of a 2-car tandem community garage with in-unit washer/dryer combo. The community offers fantastic amenities including a pool, gym, and outdoor gathering spaces perfect for enjoying the California lifestyle. Located in a desirable neighborhood with easy access to shopping, dining, and major freeways, this property is ideal for first-time buyers, investors, or anyone seeking a low-maintenance lifestyle. Only three miles from Northridge Fashion Center, Westfield Topanaga Mall, CSUN and Pierce College. Don t miss the opportunity to make this cozy and stylish condo your own!

20253 Keswick Street Unit 205, Winnetka

$585,000

2 Beds ⋅ 3 Baths ⋅ 26839989 MLS ⋅ Active Status

Welcome to this beautiful 2-bedroom, 2.5-bathroom townhome located in the highly desirable, controlled-access Windsor Park community. The thoughtfully designed floor plan features a light-filled living area with sleek floors, recessed lighting, and a cozy gas fireplace. The well-appointed kitchen boasts granite countertops and includes stainless steel appliances. A skylight leads to the upper level, which includes a dedicated laundry area complete with full-size machines and built-in cabinetry. The large primary bedroom serves as a true retreat, offering two closets, a unique step-up bonus room, and an en-suite master bath that comes with a separate tub, shower, and a double vanity. The spacious second bedroom provides excellent privacy, featuring its own attached bathroom with a tub. Complete with a private 2-car attached garage, central A/C and heating, and access to an inviting community pool and spa, this townhome is perfectly situated near shopping, parks, and transportation.

20737 Roscoe Boulevard Unit 704, Winnetka

$569,500

2 Beds ⋅ 3 Baths ⋅ SR26102761 MLS ⋅ Active Status

Centrally located between the 118 and 101 freeways, this beautiful 2-bedroom, 2.5-bathroom Windsor Park townhome has been meticulously remodeled into a turnkey, move-in-ready residence. Situated within a gated community featuring peaceful garden walkways, the home opens to a light and bright interior freshly painted in crisp white. Modern upgrades abound, including new laminate flooring throughout, smooth ceilings with inset lighting, and updated lighting fixtures and ceiling fans in the entry, dining area, living spaces, and bedrooms. The multi-level floor plan offers exceptional flexibility; upon entry, you are welcomed by a spacious living room featuring a cozy fireplace and sliding doors that lead to an enclosed private patio. The first level also provides convenient direct access to an attached two-car garage. The gourmet kitchen is fully equipped with new stainless-steel appliances—including a refrigerator, stovetop/oven, dishwasher, and microwave—alongside ample cabinetry and a counter for bar seating. The adjacent formal dining area is brightened by a private balcony, with a guest-friendly powder room located just around the corner. Privacy is a hallmark of the split-level design. As natural light pours through the hallway skylight, you reach the primary suite, which features vaulted beamed ceilings and a versatile flex space perfect for a home office, gym, or hobby area. The secondary bedroom is equally private and located near the convenient hallway laundry room. Both bedrooms feature remodeled en-suite bathrooms including new vanity cabinets, countertops, and fixtures, with the primary bathroom offering luxurious amenities such as a separate tub and shower. Residents also enjoy community access to a pool and spa. Ideally positioned near the Winnetka Recreation Center—which offers sports, fitness, and cultural programs along with a lighted baseball diamond, play area, and picnic tables—the home is also close to Warner Center, the vibrant downtown of the San Fernando Valley. This location puts you just minutes from the shopping, dining, and entertainment at The Village and Westfield, as well as the outdoor beauty of Warner Center Park.

20737 Roscoe Boulevard Unit 703, 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

$559,990

2 Beds ⋅ 3 Baths ⋅ SR26098808 MLS ⋅ Active Status

Welcome to this beautifully updated townhome in the highly desirable Windsor Park community, offering resort-style living in a gated and meticulously maintained setting. This spacious 2-bedroom, 2.5-bath residence features nearly 1,600 square feet of light-filled living space and an open, multi-level floor plan designed for comfort, functionality, and entertaining. The inviting living room showcases updated wood-style flooring, recessed lighting, a cozy gas fireplace, and seamless access to a private patio—perfect for relaxing, entertaining, or enjoying your morning coffee. The thoughtfully updated kitchen features quartz countertops, stainless steel appliances, bar seating, newer cabinetry and paint, and an adjoining dining area with its own private balcony that brings in abundant natural light. Overlooking the living room, the formal dining area creates an open and connected flow ideal for both everyday living and gatherings. Both bedrooms feature remodeled en-suite bathrooms, offering privacy and convenience. The spacious primary suite is highlighted by vaulted, beamed ceilings and a versatile raised bonus area that can serve as a home office, gym, lounge, reading area, or creative space. Additional improvements include a newer central A/C system, updated plumbing, partial electrical upgrades, updated flooring, recessed lighting, removal of the original popcorn ceilings, and remodeled bathrooms. Further highlights include direct access to a private 2-car garage, a side-by-side laundry area, ceiling fans, and ample storage throughout. Residents of Windsor Park enjoy beautifully landscaped grounds, a sparkling community pool and spa, abundant guest parking, and a peaceful residential atmosphere. Conveniently located near shopping, dining, schools, public transportation, and other everyday amenities, this move-in-ready townhome offers space, comfort, and community living in one complete package.

20737 Roscoe Boulevard Unit 203, 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.