Winnetka (WIN) Homes with Two Levels Stories

Welcome to Winnetka, California—a hidden gem nestled in the heart of Los Angeles County. This vibrant neighborhood offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, young professionals, and retirees alike. Known for its friendly community atmosphere, Winnetka boasts lush parks, excellent schools, and a variety of shopping and dining options. With a rich cultural diversity, residents enjoy a plethora of local events and festivals that bring the community together throughout the year.

One of the standout features of Winnetka is its charming two-story homes. These properties not only maximize living space but also provide a sense of grandeur and elegance that single-story homes often lack. With spacious layouts, these two-level homes are perfect for families seeking room to grow, offering multiple bedrooms, expansive living areas, and often, beautifully landscaped yards. Imagine hosting family gatherings or cozy movie nights in your inviting living room, with the kids playing in their own dedicated space upstairs.

Winnetka's two-story homes are designed to cater to modern lifestyles while maintaining a classic appeal. Many feature open-concept designs, updated kitchens, and outdoor spaces ideal for entertaining. The proximity to major highways and public transportation also ensures that you’re never far from the bustling energy of Los Angeles, while still enjoying the peaceful retreat that Winnetka provides.

Discover the charm of Winnetka and explore the wonderful two-story homes that await you in this delightful neighborhood! Your dream home is just around the corner.

Newest Winnetka (WIN) Homes with Two Levels Stories

$550,000

3 Beds ⋅ 2 Baths ⋅ GD26165117 MLS ⋅ Active Status

Welcome to 19920 Kittridge St, a brand-new two-story residence offering the privacy and feel of a home through a Tenant-in-Common (TIC) ownership structure. With its functional multi-level layout, this home provides an ideal separation between living and sleeping areas, creating a comfortable and practical floor plan for everyday living. The home features spacious living areas, an updated kitchen and bathrooms, abundant natural light, and modern finishes throughout. Enjoy the convenience of a private entrance and exclusive-use outdoor space, all within a well-maintained property in the heart of Winnetka. Conveniently located near shopping, restaurants, parks, schools, and major freeways, this home combines comfort with an excellent location. A unique opportunity for first-time buyers, owner-occupants, or anyone seeking an affordable alternative to traditional single-family homeownership in the San Fernando Valley. Property is being sold as a Tenant-in-Common (TIC) interest and is subject to the recorded TIC Agreement, which grants exclusive occupancy rights to this residence. Financing is available through lenders experienced with TIC properties. Buyer to verify all information and satisfy themselves regarding the property and TIC ownership structure.

19920 Kittridge Street, Winnetka

$569,900

3 Beds ⋅ 3 Baths ⋅ SR26162272 MLS ⋅ Active Status

Welcome to this beautifully maintained townhome nestled in one of Winnetka's most desirable communities, offering the perfect blend of comfort, convenience, and exceptional value. Ideally situated just steps from the community pool and directly adjacent to a picturesque park with tennis courts, playgrounds, and expansive green space, this inviting residence provides a peaceful setting with resort-style amenities right outside your door. Step inside to a bright and spacious living room filled with natural light, creating a warm and welcoming atmosphere. The thoughtfully designed floor plan features a convenient guest powder room, additional storage, and a seamless flow into the dining area and updated kitchen. The kitchen offers crisp white cabinetry, updated countertops, abundant workspace, and an oversized pantry for exceptional storage. Sliding glass doors lead to a generously sized private patio enhanced with artificial turf and mature landscaping, creating the perfect outdoor retreat for relaxing, entertaining, or enjoying dining under the stars. Upstairs, the spacious primary suite features an oversized closet, a separate walk-in closet and a private 3/4 en-suite bathroom. Two additional well-proportioned bedrooms share a full bathroom, and a convenient linen closet provides extra storage. Additional highlights include newer windows & slider, refinished stairs, newer flooring, fresh carpeting upstairs, a tankless water heater, and an oversized two-car garage complete with washer and dryer hookups and direct access to the home through the patio area. Residents enjoy beautifully maintained grounds, lush greenbelts, and a sparkling community pool, all within a quiet, park-side setting. This move-in ready townhome presents an incredible opportunity to own a stylish townhome in one of Winnetka's most sought-after neighborhoods, offering the ideal combination of location, lifestyle, and value.

20119 Leadwell Street Unit 3, Winnetka

$475,000

2 Beds ⋅ 2 Baths ⋅ 26864991 MLS ⋅ Active Under Contract Status

Charming Gated Townhome in the Heart of Winnetka **Rare end-unit at the back of the complex** opportunity in a sought-after gated Winnetka community! This meticulously maintained two-story townhome-style condo comes with a coveted bonus: a private, oversized two-car attached garage offering direct ground-floor access ideal for everything from everyday convenience to extra storage flexibility. The main level is designed to impress. The open-concept first floor is an entertainer's dream, anchored by rich bamboo floors, a cozy fireplace, and recessed lighting, with a handy closet at the base of the stairs adding smart everyday function. The kitchen shines with newer stainless steel appliances and flows effortlessly into the dining and living areas perfect for hosting or simply unwinding. A sliding glass door opens to a private patio, made for warm summer evenings. A stylish half bath completes this level. Upstairs, you'll find 2 generously sized bedrooms, a full bath, and the ease of nearby laundry area with space for additonal storage right beside the linen closet. Both the primary and guest bedroom enjoy sliding glass door access to a long private patio a lovely spot for morning coffee or an evening spent unwinding with a good book. The primary suite also boasts a huge walk-in closet. Life here comes with resort-style perks: a sparkling pool, relaxing hot tub, recreation room, and lush green landscaping. HOA-covered water, trash, professionally maintained landscaping. With every convenience close at hand, this home truly checks every box.Don't wait homes like this move fast! Fireplace is considered decorative, seller does not know if it works!

20155 Keswick Street Unit 107, Winnetka

$529,000

2 Beds ⋅ 3 Baths ⋅ 26862971 MLS ⋅ Coming Soon Status

Welcome to this charming 2-bedroom, 3-bathroom townhouse, offering an incredible opportunity to add your personal touch and create the home of your dreams. The thoughtfully designed floor plan features a spacious living room with soaring vaulted ceilings, creating a bright, open, and inviting atmosphere. A dedicated dining area is ideal for everyday living and entertaining, while the functional galley kitchen offers ample cabinetry and an efficient workspace. A convenient guest bathroom completes the main level.Step outside to your private enclosed patio, where a charming lemon tree provides the perfect setting for morning coffee, outdoor dining, or simply relaxing in your own peaceful retreat.Upstairs, both generously sized bedrooms feature vaulted ceilings that enhance the sense of space and natural light. The spacious primary suite includes a large walk-in closet, offering plenty of storage.Additional highlights include a direct-access two-car garage with a laundry area for added convenience. The well-maintained community also offers a sparkling swimming pool and ample guest parking for residents and visitors alike.Ideally located in one of Winnetka's most desirable neighborhoods, this townhome is just minutes from shopping, dining, parks, schools, and major freeways, providing the perfect blend of comfort, convenience, and potential. Whether you're a first-time buyer, investor, or looking to personalize your next home, this is an opportunity you won't want to miss!

19928 Chase Street Unit 27, Los Angeles

$999,999

4 Beds ⋅ 4 Baths ⋅ SR26160562 MLS ⋅ Active Status

Welcome to your own private retreat in the heart of Winnetka. This beautifully maintained 4-bedroom, 4-bath home offers approximately 2,154 square feet of thoughtfully designed living space with a highly desirable floor plan that combines flexibility, comfort, and effortless California living. A standout feature of the home is its exceptional layout, offering two bedrooms and two bathrooms on the main level, ideal for multigenerational living, overnight guests, or a private home office. Three of the four bedrooms feature walk-in closets and their own attached bathrooms, creating comfortable, private retreats throughout the home. Rich hardwood floors, abundant natural light, and spacious living areas create a warm, inviting atmosphere. The impressive family room showcases a dramatic floor-to-ceiling brick fireplace and opens seamlessly to the backyard, making indoor-outdoor entertaining effortless. Step outside to your own resort-style oasis featuring a sparkling pool and spa, cozy fire pit, expansive patio spaces, and mature fruit-bearing citrus trees that create the perfect setting for relaxing or hosting family and friends year-round. Additional highlights include an attached two-car garage, generous storage, and an unbeatable Winnetka location just minutes from Ventura Boulevard's premier shopping, dining, and entertainment. Thoughtfully designed, beautifully maintained, and loaded with features rarely found in one home, this exceptional property offers the space, privacy, and lifestyle today's buyers have been waiting for.

7940 Sunnybrae, Winnetka

$1,675,000

4 Beds ⋅ 5 Baths ⋅ SR26158070 MLS ⋅ Active Status

NEW CONSTRUCTION – Turn Key Home. Welcome to gated Kelvin Homes! Modern home 4 bed/4.5 bath with a Great room, Open floor plan with sliding doors inviting abundant natural light, Chef’s Kitchen with center island with quartz countertop. High ceilings, Laundry located downstairs. One bedroom and one bathroom located downstairs, Spacious master bedroom with balcony, walk in master closet, Upstairs has 2 additional bedrooms, Windows have shutter installed, 2 Car Garage, Paid off Solar. Move-In ready home with many upgrades, located in the center of the valley.

7329 Kelvin, Winnetka

$869,900

3 Beds ⋅ 3 Baths ⋅ SR26150708 MLS ⋅ Active Status

Elegant, stately and beautiful describle this upgraded home! Quiet tree lined street, in the quaint and sleepy town of Winnetka! Other lovely homes surrounding! The style and design simply put, is a mid century architectual masterpiece!! The lightness, and brightness of this home are sensational. The back wall of windows and height is just incredible and gives this home a feeling of indoor/outdoor living. SO much value for this $$. Amenities in this home are too numerous to mention, you must come see for yourself!. Remodled Kitchen cabinets counters, floors, all done with quality and taste and design. Fabulous open kitchen concept. You will love the simple fireplace. Large, private and serene backyard! Fruit trees front and back..

19957 Lorne, Winnetka

$599,000

3 Beds ⋅ 3 Baths ⋅ SR26153628 MLS ⋅ Active Status

Welcome to this beautifully remodeled 3 bedroom 2.5 bathroom Townhome offering the perfect blend of modern style and comfort. The home is bright and spacious, featuring central A/C and heat, laminate vinyl flooring and recessed lighting throughout the home, window roller shades, ceiling fans in all the bedrooms and in the family room. The remodeled kitchen features quartz counter tops and self-closing cabinetry. The modern updated bathrooms feature large walk-in showers with sleek glass doors, while the primary bathroom offers dual shower heads and body jet, and frameless LED anti-fog vanity mirrors. The spacious floor plan is complemented by two private patios and a large two car garage with plenty of shelves for storage. The HOA includes association pool and spa, grounds maintenance, water, and guest parking. The home is conveniently located in the center of the San Fernado Valley close to the Topanga Mall, Northridge Fashion Center, CSUN, Piece College, restaurants, schools, and parks. Lots of Upgrades. Must see to appreciate. Clean and Move-In Ready!

8241 Mason Avenue Unit C, Winnetka

$459,000

3 Beds ⋅ 2 Baths ⋅ SR26146532 MLS ⋅ Active Status

Welcome to this spacious and inviting two-story condominium offering 1,340 square feet of comfortable living space in the heart of Winnetka. This well-designed home features 3 generously sized bedrooms and 2 bathrooms, providing the perfect blend of comfort and functionality. Enjoy the added bonus of both a front and private rear patio, creating ideal spaces for morning coffee, outdoor dining, or simply unwinding after a long day. Additional conveniences include a covered parking space and access to an on-site laundry room. Residents of this well-maintained community enjoy an impressive array of resort-style amenities, including two sparkling swimming pools, a fitness center, a banquet hall/clubhouse, community laundry facilities, and beautifully maintained common grounds, offering something for everyone. Ideally situated in the central San Fernando Valley, this home provides convenient access to shopping centers, restaurants, grocery stores, parks, schools, and everyday essentials. Commuters will appreciate the proximity to major thoroughfares, including the 101 and 118 Freeways, while nearby public transportation options make getting around even easier. Enjoy being just minutes from Pierce College, Westfield Topanga, Topanga Village, Warner Center, and a variety of entertainment, dining, and recreational destinations. Whether you're a first-time buyer, growing household, or investor, this home offers an exceptional opportunity to enjoy comfort, convenience, and outstanding community amenities in a desirable Winnetka location. (Some photos have been virtually staged with Ai)

20146 Cohasset Street Unit 5, Winnetka

$550,000

3 Beds ⋅ 3 Baths ⋅ SR26145333 MLS ⋅ Active Status

Welcome to this spacious 3-bedroom, 2.5-bathroom townhome with approximately 1,424 square feet of comfortable living space in the heart of Winnetka. Situated within a well-maintained community, this home is ideally located in one of the San Fernando Valley’s most convenient neighborhoods. The thoughtfully designed floor plan features an inviting living area filled with natural light, a dedicated dining space, and a functional layout that is ideal for everyday living and entertaining. Upstairs, you’ll find three generously sized bedrooms, including a spacious primary suite with its own private bathroom. An attached two-car garage provides secure parking and additional storage. Conveniently located near Westfield Topanga Mall, Topanga Village, Warner Center, Pierce College, local parks, schools, restaurants, grocery stores, and entertainment. The home provides a wonderful opportunity to update and personalize the interior to your own style and preferences. With its desirable floor plan, spacious layout, and outstanding location, this townhome offers exceptional potential in a sought-after Winnetka community. Don’t miss the chance to make this wonderful property your next home!

8231 Mason Avenue Unit C, 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

$529,000

2 Beds ⋅ 3 Baths ⋅ SR26136752 MLS ⋅ Active Status

GATED COMMUNITY • DUAL EN-SUITE BEDROOMS • QUARTZ COUNTERTOPS • RECENTLY INSTALLED AC • PRIVATE COURTYARD ENTRY • PRIVATE PATIO • DETACHED 2-CAR GARAGE • GUEST PARKING NEARBY Beautifully updated 2-bedroom, 2.5-bath townhome located in the highly desirable Franciscan Park gated community. Thoughtfully updated and featuring a functional floor plan, this residence blends modern improvements with everyday convenience. The main level features an open-concept living and dining area designed for comfortable everyday living and entertaining. Recessed lighting enhances the space, complemented by brand-new luxury vinyl plank flooring, freshly painted walls, and newly updated baseboards. A sliding glass door provides access to the private covered patio, creating a seamless indoor-outdoor living experience. The upgraded kitchen features quartz countertops, newer cabinetry, and ample workspace, offering both style and functionality for meal preparation and everyday use. Upstairs, two spacious en-suite bedrooms each feature dual closets and new ceiling fans for added comfort. The well-designed layout provides separation between the bedrooms, enhancing privacy and functionality. Both bathrooms offer direct access from each bedroom for added convenience, and one bathtub was recently reglazed. Additional features include a recently installed AC system, brand-new luxury vinyl plank flooring downstairs, new carpet upstairs, fresh interior and exterior paint, recessed lighting on the main level, updated light fixtures upstairs, and laundry hookups located in the detached two-car garage. The detached garage also provides secure parking and additional storage with convenient access from the private drive. The covered patio located between the unit and garage offers additional outdoor living space and flexibility for a variety of uses. A private courtyard entry enhances the property's appeal and provides an additional outdoor area. Residents of the Franciscan Park community enjoy access to a resort-style pool and well-maintained common areas. Guest parking is conveniently located nearby. Conveniently situated near shopping, dining, parks, and major commuter routes, including the 101 and 118 freeways, the property offers easy access to a variety of everyday amenities and services. Move-in ready while offering opportunities for future customization, this townhome presents a combination of updated features, functional design, and a convenient location.

7509 Winnetka Ave, 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.