Winnetka (WIN) Homes with Two Levels Stories

Welcome to Winnetka, California—a charming neighborhood nestled in the heart of Los Angeles County that perfectly blends suburban tranquility with urban convenience. Known for its friendly community atmosphere, Winnetka offers a delightful escape from the hustle and bustle of city life while still providing easy access to all the amenities that Los Angeles has to offer.

As you explore this vibrant neighborhood, you’ll discover a diverse array of homes, including stunning two-level properties that cater to families and individuals alike. These multi-story homes are designed to maximize space and comfort, featuring spacious layouts that encourage both relaxation and entertainment. Imagine hosting family gatherings in your expansive living room or enjoying quiet evenings on your private balcony overlooking the lush greenery that characterizes this picturesque area.

Winnetka is not just about beautiful homes; it’s also about lifestyle. The region boasts a variety of parks, schools, and shopping centers, making it an ideal location for families. The nearby Topanga Canyon offers breathtaking hiking trails, while the community is dotted with charming cafes and local boutiques, perfect for an afternoon stroll.

Whether you’re seeking a cozy family home or a stylish retreat, Winnetka’s two-level homes provide the perfect backdrop for creating lasting memories. With its unique blend of suburban charm and urban accessibility, Winnetka is truly a hidden gem in Los Angeles County. Come and discover your dream home in this enchanting neighborhood today!

Newest Winnetka (WIN) Homes with Two Levels Stories

$599,999

3 Beds ⋅ 3 Baths ⋅ 226004589 MLS ⋅ Active Status

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. Inquire about FHA. Model-home charm, gated-community living, a private patio, and a fantastic location--this one is ready to impress and 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

$899,000

3 Beds ⋅ 3 Baths ⋅ SR26203846 MLS ⋅ Active Under Contract Status

Welcome to this beautiful two story pool home in a desirable Winnetka neighborhood. Offering 3 bedrooms, 2.5 bathrooms, and approximately 1,787 square feet of inviting living space, the home blends comfortable everyday living with fresh, contemporary updates. New landscaping, mature shade trees, and freshly painted exterior trim create wonderful curb appeal. Inside, the light filled floor plan features fresh interior paint, recessed lighting, new ceiling fans, new luxury vinyl plank flooring throughout the main living areas, and new carpeting in the bedrooms. The spacious living and dining areas flow into a welcoming family room, where a fireplace with new tile provides a stylish focal point. Expansive sliding glass doors frame views of the backyard and create an effortless connection between indoor and outdoor living. The well appointed kitchen showcases abundant two tone cabinetry, generous quartz countertops, open display shelving, and stainless steel appliances, including a new microwave and dishwasher. The primary bathroom offers a dual sink vanity and a large glass enclosed walk in shower, while the hall bathroom has been refreshed with a new vanity. New faucets throughout add a polished finishing touch. Additional improvements include a NEW HVAC system and new laundry connections in the attached two car garage. Outside, the private backyard is designed for memorable gatherings, with a large resort style pool, rock accents, a waterfall feature, expansive patio space, mature trees, and newly refreshed landscaping. Bright, spacious, and move in ready, this wonderful Winnetka home offers an exceptional setting for relaxing, entertaining, and enjoying Southern California living.

7812 Fairchild 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

$835,000

4 Beds ⋅ 3 Baths ⋅ IV26193220 MLS ⋅ Active Under Contract Status

***Call for offers: Tuesday, September 8th; counters will be sent out Wednesday 9/9; offers will be submitted to the seller Thursday 9/10.*** Welcome to 8006 Comanche Ave in Winnetka! This refreshed 4-bedroom, 3-bath home offers a versatile floor plan with one bedroom and full bathroom conveniently located on the main level. Freshly updated inside and out with new interior and exterior paint, new LVP flooring, and new carpet in all bedrooms. The inviting curb appeal is enhanced by fresh landscaping, while the garage features laundry hookups, a gas dryer connection, and a gas water heater. Ideally located in the heart of the West San Fernando Valley, close to shopping, dining, parks, and major thoroughfares. Move-in ready and perfectly positioned to enjoy all that Winnetka and the surrounding Valley have to offer! *Listing agent will not represent any buyer in this transaction under any circumstances.*

8006 Comanche, Los Angeles

$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.