Winnetka Homes with Two Levels Stories

Welcome to Winnetka, a vibrant neighborhood nestled in the heart of Los Angeles County, California. Known for its friendly atmosphere and diverse community, Winnetka offers a unique blend of suburban charm and urban convenience. With lush parks, excellent schools, and a variety of shopping and dining options, this neighborhood is perfect for families, young professionals, and retirees alike.

One of the standout features of Winnetka is its stunning homes, particularly those with two-level stories. These multi-story residences provide ample space and flexibility, making them ideal for those seeking room to grow. With spacious layouts, these homes often boast inviting living areas, well-appointed kitchens, and generous bedrooms, perfect for accommodating family life or entertaining guests. The two-level design not only enhances the aesthetic appeal but also offers the advantage of privacy, allowing for personal retreats in the upper levels.

Winnetka’s homes with two levels often come with beautiful outdoor spaces, such as landscaped yards and patios, where residents can enjoy the California sunshine. Imagine hosting summer barbecues or relaxing with a book in your own backyard oasis. The neighborhood is also conveniently located near major freeways, making it easy to explore all that Los Angeles has to offer.

Whether you’re looking for a cozy family home or a spacious retreat, Winnetka’s two-level homes provide the perfect backdrop for your California lifestyle. Come discover the charm of this delightful neighborhood and find your dream home today!

Newest Winnetka Homes with Two Levels Stories

$1,350,000

5 Beds ⋅ 3 Baths ⋅ SR26211941 MLS ⋅ Coming Soon Status

Welcome to 20720 Napa Street, located within The Village at Napa, a desirable community of newer single-family residences featuring thoughtfully designed floor plans, spacious private lots, and attached two-car garages. Tucked away on a quiet cul-de-sac, this beautifully maintained residence offers approximately 2,500 square feet of living space with 5 spacious bedrooms and 3 full bathrooms. Step inside and immediately notice the soaring vaulted ceilings, abundant natural light, neutral color palette, custom architectural niches, and elegant arched openings that give the home an open and inviting feel. Presented in mint condition, the floor plan includes a full-size bedroom on the main level, ideal for guests, multigenerational living, or a private home office, along with a full downstairs bathroom featuring an updated shower and bath area. At the heart of the home is the gourmet kitchen, featuring granite countertops, stone backsplash, stainless steel appliances, wood cabinetry, and recessed lighting. The kitchen flows into the spacious family room with a wood-burning fireplace, while a separate formal dining room provides an ideal setting for entertaining. Additional finishes include wood and stone flooring and designer carpeting throughout. Upstairs, the impressive primary suite offers a private retreat complete with a large walk-in closet, dual vanities, makeup area, separate travertine shower, and spa-style soaking tub with natural stone surround. The secondary bathrooms feature additional travertine finishes, while the generous bedrooms provide flexibility for family, guests, work-from-home space, or recreation. The large private backyard offers excellent space for a future swimming pool while still providing plenty of room for entertaining and outdoor enjoyment. An upgraded covered patio is perfect for outdoor dining and gatherings, while established fruit trees add charm and character to the yard. Additional features include a full laundry room, abundant storage, attached two-car garage, recessed lighting, and numerous upgrades throughout. Conveniently situated near highly regarded local schools, parks, shopping, dining, and everyday amenities, this home delivers the space and versatility today's buyers are looking for. With its cul-de-sac setting, downstairs bedroom and full bath, soaring ceilings, natural light, pool-size backyard, and move-in-ready condition, 20720 Napa Street is a wonderful opportunity to call The Village at Napa home.

20720 Napa Street, Winnetka

$599,999

3 Beds ⋅ 3 Baths ⋅ 226004589 MLS ⋅ Active Status

Assumable FHA loan (subject to lender approval)! Step inside and fall in love. This beautifully appointed townhome has the fresh, polished feel of a model home! Tucked inside a desirable gated community, this charming 3-bedroom, 2.5-bath residence is stylish, inviting, and ready to move right in. The welcoming living room features updated laminate flooring with 4-inch baseboards, while the gourmet island kitchen showcases granite countertops, a pantry, recessed lighting, and appliances including a refrigerator, built-in stove and oven, dishwasher, and microwave. The kitchen flows into the dining and family room combination, creating an open and comfortable setting for everyday living and entertaining. The kitchen, dining, and family room areas feature neutral ceramic tile flooring. Retreat upstairs to the spacious primary bedroom, complete with triple-wide mirrored closet doors and a private en-suite bath. The third bedroom also features mirrored wardrobe doors. Step outside to your own private patio yard, with direct access to the 2-car garage and plenty of room for additional storage. A peaceful greenbelt passage leads to the unit, and the sparkling community pool is conveniently located nearby. Location is another highlight! Enjoy easy access to grocery stores, restaurants, Starbucks, and Runnymede Park, offering tennis courts, picnic tables, and plenty of space to enjoy the outdoors. Model-home charm, gated-community living, a private patio, and a fantastic location make this one ready to impress, and it won't last!

20112 Runnymede Street Unit 3, Winnetka

$839,995

4 Beds ⋅ 3 Baths ⋅ V1-38908 MLS ⋅ Active Status

Tucked in a quiet, private neighborhood, imagine your holidays in this adorable corner lot home. With 2,165 sf, this two-level home offers plenty of space, including 4 bedrooms (primary bedroom on the ground floor), 3 baths, extra yard space, and wonderful curb appeal from multiple angles. Enjoy the big-ticket items already replaced, including a brand-new HVAC (2026) and a new roof (2026), providing comfort and peace of mind for years to come. Home tented in 2025 and sunroom flooring replaced in 2025. Newer appliances (in 2021). Updates continue with dual-paned windows throughout (2019), adding energy efficiency year-round.The ground floor primary bedroom has an updated bathroom, offering a fresh, move-in-ready retreat at the end of the day. Ground floor also has a dining area, living room, den, and large sunroom which leads to the large backyard. Enjoy decorating the 2 sloped-roofline bedrooms plus a large 3rd bedroom upstairs with lovely mountain views. Priced so you can bring your personal touch that matches your style. With over 2,100 square feet of living space, the possibilities are endless. Home is near Pierce College, John A. Sutter Middle School, Calvert St. Elementary, Runnymede Park, Winnetka Recreation Center, shops, restaurants, recreation paths, and so much more.

19860 Arminta Street, Winnetka

$849,995

5 Beds ⋅ 3 Baths ⋅ PF26203330 MLS ⋅ Active Status

First Time on the Market in 30 Years! This longtime family home offers an incredible opportunity to create the home you’ve been dreaming of. Featuring 5 bedrooms and 3 bathrooms, this spacious home offers a versatile floor plan with 4 bedrooms and 2 bathrooms upstairs, plus 1 bedroom and a full bathroom downstairs. Step outside to a nice-sized backyard with plenty of room to relax, entertain, garden, or create your own outdoor retreat. Bring your creativity and imagination and transform this well-loved home into After three decades with the same family, this home is ready for its next chapter. Whether you’re a DIY enthusiast looking for a rewarding project, an investor searching for potential, or a buyer excited to personalize a home to reflect your own style and vision, this property offers endless possibilities.

20259 Ingomar Street, Winnetka

$449,000

2 Beds ⋅ 2 Baths ⋅ P1-28885 MLS ⋅ Active Status

Welcome home to the desirable Forest Glen Community in Winnetka! This updated end unit townhome includes 2 bedrooms, 2 bathrooms, abundant natural light, and thoughtful improvements throughout. Step inside to a freshly painted interior with an inviting open layout and spacious living room that provides plenty of room to relax or entertain. The kitchen features quartz countertops and generous cabinet space, with direct access to the private patio. The patio also includes washer and dryer hookups with a laundry shed, providing added convenience.Upstairs, both generously sized bedrooms with new laminate flooring extends through the bedrooms and hallway. The staircase has also been beautifully upgraded with stained wood treads, wood balusters, and coordinating wood handrails for a warm, updated look. Additional improvements include new Milgard dual pane windows throughout, an Ecobee smart thermostat, and a refreshed downstairs bathroom with updated flooring, toilet, vanity, and medicine cabinet.Easy access to an exceptional collection of community amenities with gated access, two large swimming pools, a separate kids wading pool, jacuzzi, fitness room, clubhouse, playground, and basketball court. This unit also comes with 2 covered parking spaces. Ideally located near Pierce College, Westfield Topanga, The Village, Warner Center, Runnymede Park, Cal State Northridge, and Northridge Fashion Center, this home offers easy access to shopping, dining, recreation, and everything the West Valley has to offer!

20224 Cohasset Street Unit 9, Winnetka

$1,268,000

4 Beds ⋅ 4 Baths ⋅ OC26196498 MLS ⋅ Active Status

Welcome home! This spacious and beautifully updated 4-bedroom, 3.5-bath home with 2,070 SF on a 6,534 SF lot is ready to be yours! The bright and functional floor plan features vaulted ceilings, a formal living room, separate family room, dining area overlooking the backyard, and an updated kitchen with gray shaker cabinetry, quartz countertops, and stainless steel appliances. A downstairs bedroom with ensuite bath is ideal for guests, extended family, or a home office, with an additional powder room and indoor laundry room nearby. Upstairs features three bedrooms and two bathrooms, including a spacious primary suite with vaulted ceilings, walk-in closet, dual-sink vanity, and large shower. The home has been extensively updated with dual-pane windows, recessed lighting, flooring, copper plumbing, updated electrical, HVAC, 200-amp panel, and more. Enjoy the large, private backyard with a covered patio and artificial turf which is perfect for entertaining, outdoor dining, or relaxing with minimal maintenance. Attached two-car garage and convenient location near shopping, dining, schools, Pierce College, Westfield Topanga, and The Village at Topanga. Move-in ready and waiting for its next owner!

19700 Lull, Winnetka

$850,000

3 Beds ⋅ 3 Baths ⋅ SR26184789 MLS ⋅ Active Status

Welcome to "PICKET FENCES" neighborhood! Charming Cul-De-Sac location. Small Community of 16 Detached Homes. 3-Bedrooms with 2-full Baths upstairs. Powder Room Bathroom downstairs. This Model has if needed, a 4th Bedroom downstairs with a good size walk-in Closet or grate room, in home office or TV-Playroom. Home has 2-car attached garage along with an outside extra parking space next to garage (back areas of garage areas are gated). Enter front of home to a beautiful Formal Living Room with Gas Fireplace. Owner had professional Tile Contractor install "Italian Terracotta Tile in 2025 (beautiful Paprika color - Series Contessa by Walker Zanger)" to Fireplace. New Carpet installed 02/2026. Dining Room, TV room, Formal Living Room are engineered wooden flooring as well as Master Bedroom. Master Bath and Downstairs Bath have "TOTO" toilets. Interior Painted 07/2026. Exterior of home painted in 2020. Rain Gutters installed 09/2022. Sun Power Solar installed 12/2022. Solar was Paid in full at installation. NEXGEN A/C - ASX16 installed 06/2020. Kitchen Countertops "QUARTZ STONE" installed 2017. Bay Alarm System installed 03/2019. Mature Orange and Lemon Trees in Front Yard and with relaxing Front Porch. Assessor shows Single Residence - Detached Condominium. This is a MUST SEE!!!

7101 Oso Avenue Unit 14, Winnetka

$1,099,000

5 Beds ⋅ 3 Baths ⋅ SR26189092 MLS ⋅ Active Under Contract Status

SUNDAY OPEN HOUSE CANCELLED. Beautifully remodeled and move-in ready, this five-bedroom Winnetka home blends warm, modern design with curated finishes throughout. White oak engineered wood floors and recessed lighting set the mood, creating a fresh, cohesive feel from room to room. The kitchen shines with abundant upper and lower cabinetry, top-of-the-line Café appliances, SoliTaj quartz countertops, champagne-bronze hardware and West Elm pendant lights. A tumbled-marble fireplace adds texture and warmth to the stylish and inviting living space. The remodeled bathrooms include a polished powder room, a beautifully appointed full bathroom and a luxurious, spa-like primary bathroom. A bright sunroom expands the living space and brings in abundant natural light, while the epoxy-finished garage provides a clean, durable upgrade. Set in a quiet, charming residential neighborhood, the home is surrounded by lushly landscaped front and back yards, creating a private outdoor retreat. An exceptional patio with built-in benches provides the perfect setting for effortless hosting and daily enjoyment, while new driveway pavers complete the home’s polished curb appeal. With extensive upgrades inside and out, there is even more to appreciate in person!

19939 Hemmingway, Winnetka

$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

$620,000

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

$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

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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.