Winnetka (WIN) Homes with Two Levels Stories

Welcome to Winnetka, a charming neighborhood nestled in the heart of Los Angeles County, California. This vibrant community is known for its friendly atmosphere, diverse culture, and convenient access to a wealth of amenities. With a rich blend of suburban tranquility and urban convenience, Winnetka offers residents the perfect balance of comfort and excitement.

One of the standout features of homes in Winnetka is the abundance of two-level story residences. These multi-story homes provide not only spacious living but also a sense of privacy and separation between living spaces. Imagine entertaining guests in an expansive living room while your family enjoys a cozy movie night upstairs. The versatility of two-level homes allows for creative use of space, accommodating everything from home offices to playrooms.

Winnetka's real estate market showcases an array of architectural styles, from modern designs to charming traditional homes. Many properties feature lush backyards, perfect for weekend barbecues or tranquil evenings under the stars. The neighborhood is also known for its excellent schools, parks, and recreational facilities, making it a prime choice for families looking to settle down.

With its close-knit community vibe and easy access to major highways, shopping centers, and dining options, Winnetka is not just a place to live—it's a place to thrive. Whether you're searching for your first home, a family haven, or an investment opportunity, Winnetka's two-level homes offer the perfect canvas for your next chapter. Explore the possibilities and discover why Winnetka is the ideal place to call home!

Newest Winnetka (WIN) Homes with Two Levels Stories

$1,350,000

4 Beds ⋅ 3 Baths ⋅ SR26174769 MLS ⋅ Active Status

Fabulous "One of a kind" opportunity property with TWO SEPARATE PERMITTED STRUCTURES Come see this Gigantic Flat Lot, 26,200 sq ft with a long, private gated driveway that leads to TWO SEPARATE STRUCTURES: Structure #1 is MAIN HOUSE, and Structure #2 is separate 1,200 sq ft building which is a FIXER with a Permit and a Certificate of Occupancy This separate building would make an awesome Guest House or it would be perfect for a home business! This property has endless possibilities! There is also a private backyard w/ a beautiful sparkling swimming pool and spa in beautiful condition! The moment you enter the grounds, the size of the lot, mature fruit trees, open space, and resort-style pool create a private retreat atmosphere that is increasingly difficult to find. Property sold "As is" without warranty by Seller or Seller's Agent. Buyer to verify all info. Buyers are encouraged to independently verify all zoning, permits, lot utilization, development possibilities, and intended uses with the appropriate agencies and professionals.

20054 Arminta, Winnetka

$1,100,000

4 Beds ⋅ 3 Baths ⋅ SR26172508 MLS ⋅ Active 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

$425,000

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

$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 Under Contract 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 upstairs. One bedroom and one bathroom located downstairs,Powder room, 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.

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

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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.