Winnetka (WIN) Homes with Two Levels Stories

Welcome to Winnetka, California, a hidden gem nestled in the vibrant heart of Los Angeles County. Known for its family-friendly atmosphere and diverse community, Winnetka offers a perfect blend of suburban charm and urban convenience. With its tree-lined streets, well-maintained parks, and a variety of local shops and eateries, this neighborhood is an ideal place to call home.

One of the standout features of homes in Winnetka is the availability of two-level stories, which provide ample space and versatility for families of all sizes. These multi-level residences are perfect for those seeking a balance between privacy and togetherness. With spacious layouts, these homes often include multiple bedrooms, cozy living areas, and expansive kitchens, making them perfect for entertaining guests or enjoying quiet family evenings.

Imagine waking up in a beautifully designed two-story home, where natural light floods through large windows, illuminating your living space. The upper level often features private retreats, perfect for relaxation, while the lower level invites you to gather with loved ones. Many of these homes also come with outdoor spaces, where you can enjoy California's sunny weather, whether it's hosting a weekend barbecue or simply unwinding after a long day.

In Winnetka, you’re not just buying a house; you’re investing in a lifestyle. With excellent schools, convenient access to public transportation, and a strong sense of community, this neighborhood is ideal for anyone looking to thrive in Los Angeles County. Discover your dream home in Winnetka today and experience the perfect blend of comfort and convenience!

Newest Winnetka (WIN) Homes with Two Levels Stories

$699,000

4 Beds ⋅ 3 Baths ⋅ 26876737 MLS ⋅ Active Status

Situated in the premier position of a secure Winnetka enclave, 20300 Vanowen Street, #44, is an end-unit townhouse that effortlessly balances privacy with open-concept living. Bathed in natural light, the main level unfolds through rich hardwood floors into an expansive living area and a chef's kitchen anchored by warm granite countertops designed intentionally for effortless hosting. Upstairs, sanctuary takes center stage. Plush wool-blend carpets lead to a sophisticated primary suite featuring a private jetted soak, an expansive walk-in closet, and serene views of the surrounding mountains. Step outside to a secluded, private courtyard built for alfresco evenings. Complete with direct-access two-car parking and resort-style community amenities, including a pool and spa, this residence offers an elevated retreat minutes from the West Valley's finest shopping and dining.

20300 Vanowen Street Unit 44, Los Angeles

$1,590,000

5 Beds ⋅ 5 Baths ⋅ OC26182547 MLS ⋅ Active Status

2025 Construction NEVER LIVED IN. 4 bedroom 3 bath main house 1 bedroom 1 bath attached ADU. Energy efficient AC heat pumps. Copper plumbing. State of the art electrical. Thermador appliances with cabinets galore. Mirrored wardrobes. 11 ft ceilings. Top of the line wood clad aluminum windows.Hardwood floors. Solid doors throughout. Completely insulated to latest building codes. Gorgeous pavers driveway. Solid wood garage door. $430/sq foot Brand NEW less expensive than 25 year old homes.

20329 Stagg Street, Winnetka

$695,999

3 Beds ⋅ 3 Baths ⋅ GD26181898 MLS ⋅ Active Status

Home may qualify for up to $15,000 towards down payment assistance or closing costs! Where can you find a detached home in a gated community with an HOA of only $70 per month? Right here at 20230 Keswick #3! Add in a low $87 monthly solar lease, thoughtful upgrades, and a desirable Winnetka location, and this home offers a combination of value, comfort, and convenience that is hard to find. This beautifully updated 3-bedroom, 3-bathroom detached home has no common walls and has been thoughtfully improved to create a bright, modern, and welcoming living space. The kitchen has been opened up to create an inviting open-concept floor plan, allowing the kitchen, dining, and living areas to flow effortlessly together—perfect for everyday living and entertaining. Inside, you'll find hardwood flooring, fresh interior paint, recessed lighting, upgraded electrical, new plumbing, a cozy fireplace, and appliances included. The kitchen offers generous counter and cabinet space while opening directly into the main living areas, creating a spacious and connected feel. All three bedrooms are located upstairs, offering privacy and separation from the main entertaining spaces. With three bathrooms, including a convenient guest bathroom on the main level, the layout is as functional as it is comfortable. Step outside to your private patio, a space ready for morning coffee, weekend BBQs, entertaining friends, or simply creating memories with the people you love. Additional upgrades and conveniences include a new garage system, new washer and dryer, refrigerator, attached 2-car garage, solar panels with a low $87 monthly lease payment, and the added privacy and security of a gated community. With an incredibly low $70 monthly HOA, low solar payment, numerous upgrades, private outdoor space, and a detached-home feel, this property delivers exceptional value in a great neighborhood. Location is another standout. Situated in the heart of the San Fernando Valley, the home offers convenient access to the 101, 118, and 405 freeways, making it easy to get around the Valley and beyond. You're also close to CSUN, shopping, dining, entertainment, and everyday conveniences—putting so much of what the Valley has to offer within easy reach.

20230 Keswick Unit 3, Winnetka

$999,500

4 Beds ⋅ 3 Baths ⋅ 26874079 MLS ⋅ Active Status

Tucked away on a quiet double cul-de-sac, this charming Traditional home radiates warmth and comfort at every turn. Offering approximately 2,230 square feet of thoughtfully designed living space, the home features a formal living room with integrated in-ceiling speakers, a formal dining room, newer flooring, and recessed lighting throughout.Designed for modern living, this is a true smart home with Alexa-enabled lighting, a Control4 audio/video system, and whole-home integration, and a solar system. The light-filled den is ideal for entertaining, complete with a wet bar and fireplace, and easily converts into a theater-like experience featuring a 110-inch drop-down motorized screen, 4K projector (included), and surround sound perfect for cozy movie nights at home. At the heart of the home is the beautifully remodeled, open-concept kitchen, showcasing quartz countertops, a breakfast bar, coffee nook, built-in TV, and seamless sight lines throughout the entire downstairs. A remodeled powder room completes the main level. Upstairs, the spacious primary suite includes a remodeled en-suite bath, accompanied by three additional well-sized bedrooms and a fully remodeled secondary bath.The low-maintenance backyard is an entertainer's dream, offering a covered patio, deck, built-in BBQ center, multiple seating areas, backyard sound system, and a built-in fire pit creating the perfect setting for memorable evenings. The two-car garage with direct access has been converted into an additional fifth bedroom with a fourth bathroom (unpermitted), featuring Brilliant smart touch light switches and Wi-Fi-enabled ceiling lights. The space can easily be restored to a traditional garage if desired. Additional highlights include a security system, Leased Solar System (Buyer to assume lease), newer roof, and updated electrical panel. Ideally located near shopping, dining, and entertainment this exceptional home truly has it all. Look no further.

20241 Baltar Street, Los Angeles

$925,000

4 Beds ⋅ 3 Baths ⋅ SR26180966 MLS ⋅ Active Status

Welcome to this lovingly owned and meticulously maintained two-story Winnetka home, cherished by the same family for 51 years! Situated on a quiet street and thoughtfully designed with a smart, flexible floorplan, this 4-bedroom, 3-bath home offers comfortable living with plenty of space to accommodate today’s lifestyle. The main level features a welcoming living room with fireplace, formal dining area, and a spacious kitchen/great room complete with wet bar—an ideal gathering space for everyday living and entertaining. A downstairs bedroom and ¾ bath provide wonderful flexibility for a home office, guests, or multi-generational living. Upstairs, the private primary suite features a beautifully remodeled bath, along with two additional bedrooms and hall bath. The extensive list of updates reflects years of thoughtful care: 2026—smooth ceilings, fresh interior paint, updated interior door hardware and hinges, new ceiling fans, Decora-style switches and outlets, new drapes and rods, hall toilet, and new and updated recessed lighting; 2025—remodeled primary bath and new water heater; 2018—new roof; 2015—dual-zone HVAC and new windows, including triple-pane windows upstairs and double-pane windows downstairs; 2010—house replumbed with pex; 1994—chimney rebuilt. With its flexible layout, inviting outdoor spaces, substantial updates, and peaceful Winnetka location close to parks, shopping, and schools, this special home is ready for its next chapter. Don’t miss the opportunity to make it yours!

8126 Laramie Avenue, Winnetka

$644,000

3 Beds ⋅ 3 Baths ⋅ BB26177607 MLS ⋅ Active Status

Move-in ready 3-bedroom, 3-bathroom townhome situated on a quiet residential street surrounded by homes, within an intimate 27-unit community. The bright living room features vaulted ceilings, recessed lighting, a fireplace, and direct access to a private patio, creating an inviting space for everyday living and entertaining. The open-concept kitchen flows into the dining area and features granite countertops and new porcelain tile flooring. Recent improvements include new Pergo flooring throughout, new carpet on the stairs, a remodeled primary bathroom, new tankless water heater, new electrical subpanel, and recessed lighting. All three bedrooms are located upstairs and feature vaulted ceilings. The spacious primary suite includes a walk-in closet and remodeled ensuite bathroom, while a second full bathroom serves the additional bedrooms. A guest powder room is conveniently located on the main level. Enjoy the convenience of a large private 2-car garage with direct access and a dedicated laundry area, plus central air and heat. The community also features a large gated swimming pool. Offering a comfortable floor plan, thoughtful updates, private outdoor space, and a desirable residential setting, this townhome is ready to welcome its next owner.

19928 Chase Street Unit 23, Winnetka

$1,100,000

4 Beds ⋅ 3 Baths ⋅ SR26172508 MLS ⋅ Active Under Contract Status

This is a must see. A home in the valley that offers a large downstairs along with a spacious loft upstairs perfect for entertaining space, play room, movie room or in home office. The downstairs has a large living room, designated dining space, eat in kitchen with a wet bar, a family room with a sliding glass door that leads to the backyard, a half bath and indoor laundry area. There's also a two car garage attached to the house. Upstairs are 4 bedrooms. The main bedroom is large enough to have its own living room space. The main bathroom has double sinks, bathtub and a shower, as well as walk in closet. from the main bedroom is a french door that leads out to the balcony. There is a large loft, and three other bedrooms, and an additional bathroom. The backyard has citrus trees, a dog run and plenty of room for outdoor seating and dining. This house has newer paint inside and out, newer double paned windows and sliders, all new recessed lighting, plantation shutters and custom wood blinds.

7923 Casaba, Winnetka

$395,000

2 Beds ⋅ 2 Baths ⋅ SB26170238 MLS ⋅ Active Status

Welcome to this beautifully updated condominium offering comfort, style, and exceptional value. This spacious two-bedroom home features an ideal layout with two generously sized bedrooms, each offering the feel and privacy of a primary suite. The open-concept kitchen overlooks the living room, creating the perfect space for entertaining, while the private balcony provides a relaxing place to enjoy views of the surrounding neighborhood. Recent renovations include fresh interior paint, new flooring, upgraded granite countertops, and a modern ceiling design that adds warmth and character throughout the home. Additional features include in-unit laundry, two tandem parking spaces, and access to a well-maintained community with outstanding amenities for residents to enjoy. Best of all, this is one of the best-priced units in the complex, making it an incredible opportunity for first-time buyers, down sizers, or anyone looking for exceptional value. Come see why this beautiful home is the perfect place to call your own!

20253 Keswick Unit 322, Winnetka

$1,575,000

4 Beds ⋅ 5 Baths ⋅ SR26166115 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 upstairs. One bedroom and one bathroom located downstairs, Spacious master bedroom with balcony, walk in master closet, Upstairs has 3 additional bedrooms, Most Windows have shutter installed, 2 Car Garage, Paid off Solar. Move-In ready home with many upgrades, located in the center of the valley.

20811 W Seeasons Lane, Winnetka

$500,000

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

$529,000

2 Beds ⋅ 3 Baths ⋅ 26862971 MLS ⋅ Active 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

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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.