Winnetka (WIN) Homes for Sale

Welcome to this rare opportunity featuring three detached homes on one expansive 9,461 sqft lot 8434, 8436 & 8438 Oakdale Avenue. Beautifully redesigned with modern finishes, energy efficiency, and flexible living in mind, this one-of-a-kind property is ideal for multi-generational living, owner-users, or savvy investors seeking immediate cash flow potential. The main residence at 8434 Oakdale offers approximately 1,300 sqft of thoughtfully designed living space featuring 3 spacious bedrooms and 2 beautifully updated bathrooms. Completely remodeled inside and out, this home showcases an open-concept floor plan filled with natural light, recessed lighting, new flooring throughout and seamless indoor-outdoor living. The stunning chef-inspired kitchen opens directly to the living and dining areas, creating the perfect atmosphere for entertaining. Step outside to your own private backyard retreat featuring a covered gazebo with ceiling fans & TV, outdoor built-in kitchen and ample space for gatherings and relaxation. Additional highlights include fully paid-off solar panels and an EV charger for energy-efficient living. The detached ADU at 8436 Oakdale, newly built in 2024 offers approximately 1,067 sqft with 3 bedrooms and 2 bathrooms. Designed for complete independence and privacy, this stylish home features a modern kitchen with new appliances, laminate flooring throughout, efficient heating and cooling systems, in-unit washer and dryer, and its own private backyard space. Privately situated at the rear of the property, the SB9 studio at 8438 Oakdale is a beautifully designed 430 sqft detached unit maximizing every inch of space. Complete with a kitchenette, private bathroom, in-unit laundry, private entrance, and dedicated front yard area, this flexible space is ideal for rental income, guests, extended family, or a home office setup. Each residence enjoys separate addresses, private entrances, front and backyard areas, and no shared walls offering true privacy and independence for every occupant. The property also features a circular driveway with abundant parking, modern energy-efficient construction, and exceptional versatility rarely found on the market today. Whether you’re looking to live in one unit while offsetting your mortgage with rental income, accommodate extended family with separate yet connected living spaces, or capitalize on a high-income-producing investment opportunity, this extraordinary Winnetka compound offers endless possibilities.

8434 Oakdale Avenue, Winnetka

$780,000

3 Beds ⋅ 2 Baths ⋅ SR26183308 MLS ⋅ Active Status

Welcome to 8043 Sunnybrae Avenue, a beautifully updated single-story home tucked away on a quiet residential street in Winnetka. This inviting 3-bedroom, 2-bath residence blends modern finishes, comfortable living spaces, and an impressive oversized lot. The bright and open interior features a spacious living room with a fireplace, stylish wood-look flooring, and an updated kitchen showcasing quartz countertops, contemporary cabinetry, stainless steel appliances, and ample storage. Both bathrooms have been tastefully remodeled, while generously sized bedrooms offer excellent natural light and closet space. Additional highlights include central HVAC, ceiling fans throughout, a dedicated laundry room with washer and dryer hookups, and an attached two-car garage. Step outside to an expansive backyard offering exceptional space for entertaining, outdoor dining, gardening, a pool, ADU, or future expansion possibilities. With approximately 8,097 square feet of lot space, this property offers tremendous versatility and long-term potential. Move-in ready, thoughtfully updated, and offering the indoor-outdoor lifestyle Southern California buyers are looking for, this Winnetka home is one you won’t want to miss.

8043 Sunnybrae, 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

$849,900

4 Beds ⋅ 2 Baths ⋅ 226003954 MLS ⋅ Active Status

Welcome to this charming Winnetka single story on a sweeping corner lot! From the moment you enter, you'll feel the warmth and care that's been put into this beautiful home. 4 bedrooms, 2 bathrooms, formal dining room, living room with Swedish fireplace, family/recreation room with custom bar, perfect for your family gatherings! So much love here. Granite kitchen with custom cabinets and breakfast bar. Lots of natural light and plenty of built-ins and storage throughout entire home. Large primary suite with huge walk in shower. The spacious backyard has a newer concrete patio and large grassy yard for pets and kiddos! 2 car garage. Roof is only 4 years old. Hurry and start making wonderful memories in this special home!

20256 Londelius Street, 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

$1,649,950

7 Beds ⋅ 5 Baths ⋅ SR26177843 MLS ⋅ Active Status

Welcome to this rare opportunity featuring three detached homes on one expansive 9,461 sqft lot 8434, 8436 & 8438 Oakdale Avenue. Beautifully redesigned with modern finishes, energy efficiency, and flexible living in mind, this one-of-a-kind property is ideal for multi-generational living, owner-users, or savvy investors seeking immediate cash flow potential. The main residence at 8434 Oakdale offers approximately 1,300 sqft of thoughtfully designed living space featuring 3 spacious bedrooms and 2 beautifully updated bathrooms. Completely remodeled inside and out, this home showcases an open-concept floor plan filled with natural light, recessed lighting, new flooring throughout and seamless indoor-outdoor living. The stunning chef-inspired kitchen opens directly to the living and dining areas, creating the perfect atmosphere for entertaining. Step outside to your own private backyard retreat featuring a covered gazebo with ceiling fans & TV, outdoor built-in kitchen and ample space for gatherings and relaxation. Additional highlights include fully paid-off solar panels and an EV charger for energy-efficient living. The detached ADU at 8436 Oakdale, newly built in 2024 offers approximately 1,067 sqft with 3 bedrooms and 2 bathrooms. Designed for complete independence and privacy, this stylish home features a modern kitchen with new appliances, laminate flooring throughout, efficient heating and cooling systems, in-unit washer and dryer, and its own private backyard space. Privately situated at the rear of the property, the SB9 studio at 8438 Oakdale is a beautifully designed 430 sqft detached unit maximizing every inch of space. Complete with a kitchenette, private bathroom, in-unit laundry, private entrance, and dedicated front yard area, this flexible space is ideal for rental income, guests, extended family, or a home office setup. Each residence enjoys separate addresses, private entrances, front and backyard areas, and no shared walls offering true privacy and independence for every occupant. The property also features a circular driveway with abundant parking, modern energy-efficient construction, and exceptional versatility rarely found on the market today. Whether you’re looking to live in one unit while offsetting your mortgage with rental income, accommodate extended family with separate yet connected living spaces, or capitalize on a high-income-producing investment opportunity, this extraordinary Winnetka compound offers endless possibilities.

8434 Oakdale Avenue, Winnetka

$899,950

4 Beds ⋅ 2 Baths ⋅ SR26178270 MLS ⋅ Active Under Contract Status

Beautifully renovated four-bedroom, two-bathroom home offering approximately 1,300 square feet of thoughtfully updated living space. This move-in-ready property features a brand-new roof, new heating and air-conditioning system with all-new ductwork, energy-efficient double-pane windows, and new vinyl flooring throughout. The updated kitchen includes brand-new cabinets, countertops, and modern finishes. Both bathrooms feature new vanities and stylish upgrades. Additional improvements include extensive plumbing and electrical work, a tankless water heater, and sewer line upgrades. The freshly improved exterior features new landscaping, grass, plants, tree removal, and a brand-new irrigation system. The interior and exterior have been freshly painted, creating a clean and welcoming appearance. All work has been completed with permits, offering added confidence and peace of mind. Simply move in and enjoy this beautifully updated home.

20701 Schoolcraft, Winnetka

$900,000

3 Beds ⋅ 1 Baths ⋅ SR26178067 MLS ⋅ Active Status

Great opportunity to build your own compound on this 17,000+ SF lot with two driveway gates and street entries. Space to build an ADU or expand the main house to suit your needs. All flat land and ready for your dream ideas! Perfect setup for SB 9 or the upcoming AB 1033 opportunities to sell two separate homes from one large parcel, or other new laws that allow for more units on a single lot. The block wall along the front of the property provides privacy. The two gates make it easy to drive in and out, or use one as a separate driveway to reach the back part of the lot. The potential is amazing, and the location is undergoing rapid redevelopment. Two-car garage with large expansion for a workshop or other uses. Plenty of room for an RV or multiple cars on this property. Do not miss this rare opportunity.

20744 Parthenia, Winnetka

$829,900

3 Beds ⋅ 2 Baths ⋅ SR26166729 MLS ⋅ Active Status

Welcome to your dream home—an incredible opportunity you don’t want to miss! This beautifully upgraded 3-bedroom, 2-bathroom gem is truly turnkey and ready for you and your family to move right in. Whether you’re a commuter looking for convenience or ready to settle into a peaceful lifestyle, this home offers the perfect blend of comfort, style, and location. Recently renovated from top to bottom, it features a stunning remodeled primary bathroom, upgraded fixtures throughout, fresh interior paint, brand-new carpeting in the bedrooms, and newly installed waterproof vinyl flooring that adds both beauty and durability. The versatile bonus room provides endless possibilities—create your ideal home office, cozy den, playroom, or even a guest space. Let your imagination bring it to life! Step outside and fall in love with your private backyard oasis. Enjoy sunny California days in the fully gated pool complete with a diving board, surrounded by a beautifully landscaped yard and even your own orange tree—perfect for relaxing or entertaining. The upgrades don’t stop there—a newer roof (just one year old!) comes with a 30-year warranty, offering peace of mind for years to come. Located in a well-established, family-friendly neighborhood with a charming suburban feel, this home is ideally situated near Woodland Hills, Northridge, and Canoga Park. You’ll enjoy easy access to parks, top shopping and dining, schools, and entertainment—all in a prime central Valley location with strong rental and resale potential. Imagine the memories waiting to be made here… This is more than a home—it’s a lifestyle and an unbeatable value. Opportunities like this don’t last—submit your offer before it’s gone! It's time to start your new chapter! Property is being sold (AS IS). All information, including but not limited to measurements and calculations of area, has been obtained from various sources and has not been, and will not be, verified by the broker, agent, or MLS. The accuracy of such information is not guaranteed. Buyers are strongly advised to independently verify all information and conduct their own due diligence regarding all aspects of the property. The seller and listing agent make no representations or warranties, expressed or implied, as to the accuracy of all the information provided.

7509 Sunnybrae, Winnetka

$949,000

3 Beds ⋅ 2 Baths ⋅ SR26175136 MLS ⋅ Active Status

Why settle for ordinary when you can have retro-inspired charm, modern updates, and your own private pool? Welcome to 8012 Comanche - a 3-bedroom, 2-bathroom, Woodland Hills adjacent, Mid-Century Modern home in the heart of Winnetka that blends personality with classic Southern California living. Approximately 1,733 square feet on a 5,227-square-foot lot, the house has been updated while keeping its fun retro vibe. Step through the solid wood front door into a spacious living room with a gas fireplace. The kitchen, finished with stainless-steel appliances, opens to an outdoor dining area made for long dinners and weekend gatherings. The primary bedroom opens to the pool, giving it a quiet resort feel. The other two bedrooms currently function as private home offices. All bedrooms have ceiling fans. Both bathrooms feature modern walk-in showers. An attached 2-car garage, owned solar, and a 10-camera HIK Vision security system add everyday convenience and peace of mind. Out back, the private inground pool turns the yard into a true retreat. Fruit trees in the front garden add a touch of productive charm. Updated, move-in ready, filled with character, and complete with your own private pool - 8012 Comanche offers a combination that’s increasingly hard to find. Come see what makes this Winnetka home anything but ordinary! Furnishings, artwork, and select electronics are available for separate purchase if you want a turnkey start. Ideally located near the 101 and 118 freeways, CSUN, Pierce College, Warner Center, Westfield Topanga, and The Village. Convenient access to Whole Foods plus easy drive through Topanga Canyon to Malibu.

8012 Comanche, Winnetka

$1,049,500

4 Beds ⋅ 3 Baths ⋅ 226003821 MLS ⋅ Active Status

Completely reimagined and meticulously renovated, this exceptional Winnetka residence delivers the rare combination of modern design and thoughtful functionality. From the moment you step inside, you're greeted by new luxury vinyl plank flooring and a light-filled open flow. The showpiece kitchen features custom cabinetry, quartz countertops, an oversized island, and recessed lighting, creating a space equally suited for everyday living and entertaining.While title reflects a 3-bedroom, 2-bath home, the current layout offers the functionality of 4 bedrooms, 2.5 bathrooms, plus a dedicated office--ideal for today's evolving lifestyle. Adding to the home's unique story, the original building plans, available for review, depict the home as being designed with four bedrooms plus the bonus room, indicating this layout is original to the home rather than the result of a later addition or expansion.The bathrooms have been fully remodeled with timeless finishes, walk-in closets add everyday convenience, and fresh paint with updated hardware carries throughout the home. Behind the walls, major infrastructure upgrades include copper plumbing and a new electrical panel, providing added peace of mind.Out front, a gated entry and low-maintenance turf create clean, secure curb appeal. The attached two-car garage includes laundry hookups, with additional paved RV parking alongside the home, while a large detached storage room provides incredible space for hobbies, tools, seasonal items, or additional storage. The backyard offers a clean, low-maintenance canvas ready to be customized to your vision.Located in the heart of Winnetka, you'll enjoy convenient access to local parks, shopping, dining, schools, and major commuter routes, making everyday living as practical as it is enjoyable.This is far more than a cosmetic refresh--it's a thoughtfully executed renovation where nearly every surface and major system has been updated to create a home that feels cohesive, intentional, and truly move-in ready.

8018 Winnetka Avenue, Winnetka

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