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

$990,000

4 Beds ⋅ 3 Baths ⋅ SR26193908 MLS ⋅ Active Status

Welcome to this spacious and beautifully appointed 4 bedroom, 3 bathroom home offering approximately 2,491 square feet of comfortable living space. Designed with an inviting open floor plan, the home offers distinct living, dining, and family rooms that provide plenty of space for everyday living, entertaining, and gathering with family and friends. Hand finished hardwood flooring extends throughout the home, adding warmth and character, while vaulted ceilings enhance the sense of openness and natural light. The kitchen is both stylish and functional, featuring granite countertops, a center island, maple cabinetry, and stainless steel appliances, creating a welcoming space for preparing meals and entertaining. The generously sized primary suite provides a relaxing retreat with a walk in closet and an elegant en suite bathroom featuring dual sinks, marble countertops, custom tile and mosaic details, and an oversized shower. Additional features include central air conditioning and heating, a gas fireplace, tankless water heater, dual glazed high efficiency vinyl framed windows, and a convenient second floor indoor laundry room. Outside, the paved driveway provides easy access, while the wood fenced rear and side yards offer privacy and flexibility for outdoor enjoyment. The outdoor gazebo and dedicated BBQ area create an inviting setting for weekend gatherings, al fresco dining, or relaxing outdoors. With its spacious layout, thoughtful finishes, comfortable amenities, and versatile indoor and outdoor living spaces, this home offers a wonderful opportunity to enjoy both everyday comfort and effortless entertaining.

7861 Fluffy Duckling Lane, 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. All Bathrooms 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 Status

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

$495,000

2 Beds ⋅ 3 Baths ⋅ GD26187826 MLS ⋅ Active Status

This inviting Winnetka townhouse perfectly combines comfort, convenience, and charm in a desirable community. Pull into your spacious 2-car garage and step inside this beautifully maintained 2-bedroom, 3-bathroom home, 2 Fireplaces, & ideally located in the heart of Winnetka. The bright and spacious floor plan features generous living and dining areas, highlighted by a cozy fireplace that creates the perfect setting for relaxing evenings and effortless entertaining. Upstairs, both bedrooms offer privacy and comfort. The spacious primary suite features its own fireplace, creating a warm and tranquil retreat for relaxing at the end of the day. Step outside to enjoy your private patio—perfect for weekend BBQs, morning coffee, or an evening drink. Residents can also take advantage of the community’s resort-style amenities, including a sparkling pool, relaxing spa, and tennis/pickleball court. The beautifully maintained courtyard provides a pleasant space to walk your pet and enjoy the outdoors. Conveniently located near California State University, Northridge, Pierce College, schools, shopping, dining, parks, schools, and major freeways, this home offers the perfect balance of peaceful community living and easy access to everything the area has to offer. Whether you're a first-time buyer, looking to downsize, or searching for a great investment opportunity, this charming Winnetka gem is ready to welcome you home!

8330 Penfield Unit 11, Winnetka

$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. Water included in the HOA dues.

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

$925,000

4 Beds ⋅ 3 Baths ⋅ SR26180966 MLS ⋅ Active Under Contract 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

$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

$1,525,000

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. Please google 7329 Kelvin Ave., Winnetka, CA - 91306 for directions as the house is located on a private street.

20811 W Seeasons Lane, 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.