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$875,000
3 Beds 2 Baths 26845941 MLS Active Under Contract Status
Welcome to 20158 Gresham St, a charming 3-bedroom, 2-bath home located in the heart of beautiful Winnetka. Built in 1959 and offering approximately 1,650 square feet of living space, this inviting property presents an exciting opportunity to own a home in one of the San Fernando Valley's most centrally located communities. Filled with warmth, character, and comfortable living spaces, this home offers the perfect setting for everyday living, entertaining guests, or simply relaxing and enjoying all that the neighborhood has to offer. Relax in the covered patio and harvest the sweetest oranges, lemons and tangerines from your generous fruit trees. Your new home is conveniently located near parks, schools, dining, and entertainment, you'll enjoy easy access to Westfield Topanga, The Village at Topanga, Northridge Fashion Center, and the 118 Freeway, making it easy to commute and explore everything Southern California has to offer. Whether you're looking for your first home, your next home, or an investment in a thriving community, this Winnetka gem offers the ideal combination of comfort, convenience, and location. Don't miss the opportunity to make it yours. The heavy lifting has been done with copper plumbing throughout and the roof was just reshingled with "Cool Roof" shingles to reduce utilty costs.

20158 Gresham Street, Winnetka

$549,000
3 Beds 3 Baths SR26118467 MLS Active Status
$40,000 Price Reduction!!! Rare opportunity with unlimited potential in this spacious and inviting townhome! Offering approximately 1,600 square feet of living space, this well-designed residence provides the perfect foundation to create the home you've always envisioned. Featuring three generously sized bedrooms, including a primary suite with its own private balcony, and 2.5 bathrooms, the thoughtfully designed floor plan offers both comfort and functionality. Whether your style leans toward sleek modern finishes, timeless traditional charm, or something entirely unique, this home is ready for your personal touch and creative vision. The attached two-car garage provides direct access to a private patio conveniently located off the kitchen and family room, creating an ideal setting for indoor-outdoor living and entertaining. Relax by the cozy fireplace in the living room, or enjoy the many benefits of this welcoming community, including wide driveways, abundant guest parking, a large community pool, spa, and tennis courts. Ideally situated near parks, shopping, and dining, this hidden gem combines exceptional convenience with incredible potential. Don't miss this chance to transform a wonderful space into your dream home and make it truly your own.

8430 Winnetka Avenue Unit 20, Winnetka

$585,000
2 Beds 3 Baths 26839989 MLS Active Status
Welcome to this beautiful 2-bedroom, 2.5-bathroom townhome located in the highly desirable, controlled-access Windsor Park community. The thoughtfully designed floor plan features a light-filled living area with sleek floors, recessed lighting, and a cozy gas fireplace. The well-appointed kitchen boasts granite countertops and includes stainless steel appliances. A skylight leads to the upper level, which includes a dedicated laundry area complete with full-size machines and built-in cabinetry. The large primary bedroom serves as a true retreat, offering two closets, a unique step-up bonus room, and an en-suite master bath that comes with a separate tub, shower, and a double vanity. The spacious second bedroom provides excellent privacy, featuring its own attached bathroom with a tub. Complete with a private 2-car attached garage, central A/C and heating, and access to an inviting community pool and spa, this townhome is perfectly situated near shopping, parks, and transportation.

20737 Roscoe Boulevard Unit 704, Winnetka

$1,699,950
7 Beds 5 Baths SR26105233 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

$846,600
4 Beds 2 Baths OC26108580 MLS Active Under Contract Status
This inviting single-story home in a quiet Winnetka neighborhood offers 4 bedrooms and 2 bathrooms in the main residence, along with a bonus room with 1-bathroom created from a converted garage—ideal for extended family, guests, or workspace flexibility. Step outside to your own private oasis featuring a refreshing backyard pool, perfect for relaxing or entertaining. Due to the pool layout, the property is not suitable for adding an ADU, but the existing bonus unit provides additional living space. Inside, you’ll find a bright, open living area, a functional kitchen, and a comfortable layout that suits both everyday living and gatherings. The front yard is gated, and while the driveway provides limited parking, the overall lot still offers cozy curb appeal and privacy. Located near schools, parks, shopping, and major transportation routes, this home presents a fantastic opportunity to enjoy Valley living with flexible space and summer-ready amenities.

20606 Skouras Drive, Winnetka

$569,500
2 Beds 3 Baths SR26102761 MLS Active Status
Centrally located between the 118 and 101 freeways, this beautiful 2-bedroom, 2.5-bathroom Windsor Park townhome has been meticulously remodeled into a turnkey, move-in-ready residence. Situated within a gated community featuring peaceful garden walkways, the home opens to a light and bright interior freshly painted in crisp white. Modern upgrades abound, including new laminate flooring throughout, smooth ceilings with inset lighting, and updated lighting fixtures and ceiling fans in the entry, dining area, living spaces, and bedrooms. The multi-level floor plan offers exceptional flexibility; upon entry, you are welcomed by a spacious living room featuring a cozy fireplace and sliding doors that lead to an enclosed private patio. The first level also provides convenient direct access to an attached two-car garage. The gourmet kitchen is fully equipped with new stainless-steel appliances—including a refrigerator, stovetop/oven, dishwasher, and microwave—alongside ample cabinetry and a counter for bar seating. The adjacent formal dining area is brightened by a private balcony, with a guest-friendly powder room located just around the corner. Privacy is a hallmark of the split-level design. As natural light pours through the hallway skylight, you reach the primary suite, which features vaulted beamed ceilings and a versatile flex space perfect for a home office, gym, or hobby area. The secondary bedroom is equally private and located near the convenient hallway laundry room. Both bedrooms feature remodeled en-suite bathrooms including new vanity cabinets, countertops, and fixtures, with the primary bathroom offering luxurious amenities such as a separate tub and shower. Residents also enjoy community access to a pool and spa. Ideally positioned near the Winnetka Recreation Center—which offers sports, fitness, and cultural programs along with a lighted baseball diamond, play area, and picnic tables—the home is also close to Warner Center, the vibrant downtown of the San Fernando Valley. This location puts you just minutes from the shopping, dining, and entertainment at The Village and Westfield, as well as the outdoor beauty of Warner Center Park.

20737 Roscoe Boulevard Unit 703, Winnetka

$640,000
2 Beds 3 Baths SR26103630 MLS Active Under Contract Status
Completely remodeled and move in ready, this spacious end unit 2 bedroom + loft, 2.5 bathroom townhouse offers the feel and functionality of a single family home at an incredible value. Located within a gated community, this approximately 1,780 sq ft home features soaring ceilings, abundant natural light, and an ideal floor plan with generously sized living spaces throughout. As an end unit with only one shared wall, the home offers added privacy and a more single family home feel. The large living room with fireplace flows seamlessly into the formal dining area and oversized eat in kitchen, creating the perfect setup for both everyday living and entertaining. The beautifully remodeled kitchen features new cabinetry, countertops, fixtures, lighting, and stainless steel appliances. Bathrooms have also been tastefully updated with modern finishes throughout. Upstairs, both bedrooms feature their own en-suite bathrooms, including a spacious primary suite with a large walk in closet complete with custom cabinetry. The versatile loft area is ideal for a home office, second living space, gym, or could easily be converted into a third bedroom. Enjoy outdoor living on the oversized private patio with plenty of room for multiple seating areas, dining, and BBQ setup. Additional upgrades include new lighting, flooring, fixtures, and designer touches throughout. The home also features a private 2 car garage with direct access into the kitchen for added convenience. With the space, layout, and privacy typically associated with a single family home, but at a townhouse price point, this is a rare opportunity you won’t want to miss.

20851 Community Unit 1, Winnetka

$655,000
3 Beds 3 Baths SW26096401 MLS Active Status
Welcome to Sherman Courts — One of Winnetka's Most Sought-After Gated Communities This stunning multi-level townhome offers the perfect blend of space, style, and resort-style living in the heart of the San Fernando Valley. Situated as a corner unit with only one shared wall, this home lives large with an open, airy feel and natural light pouring in from multiple directions. Spread across three levels, the thoughtfully designed floor plan offers incredible flexibility. The lower level features a generous bonus room perfect as a third bedroom, home office, media room, or gym — a true flex space that adapts to your lifestyle. The main level is made for entertaining, anchored by a warm and inviting family room with a gorgeous red brick fireplace. The open living and dining area features a wet bar and flows seamlessly to a private patio — the perfect spot to relax or dine al fresco in Southern California's year-round sunshine. The beautifully appointed kitchen boasts granite countertops and stainless steel appliances, making it as functional as it is stylish. The upper level is home to the spacious primary suite with a private bath, his-and-hers closets, and a private balcony, plus an additional bedroom and a versatile loft — ideal as a home office, playroom, creative retreat, or 4th bedroom. Updated bathrooms throughout and new flooring add a fresh, modern finish at every turn. The attached direct-access 2-car garage includes washer and dryer hookups for everyday convenience, plus ample storage. An additional reserved parking spot is also included — a rare bonus. Sherman Courts is a beautifully maintained gated community featuring a sparkling pool, spa, lighted tennis courts, and picnic area. A true resort-style living steps from your front door. HOA dues of $485/month cover water, trash, exterior structural insurance, roof maintenance, and 1 reserved parking space. Located in the heart of Winnetka just 25 miles northwest of downtown Los Angeles, residents enjoy easy access to top shopping, diverse dining, parks, Pierce College, Cal State Northridge, and major commuter routes. 1,843 sq ft | 3 Bed + Loft | 2.5 Bath | 2-Car Garage + Reserved Parking | Gated Community Spacious. Stylish. Move-in ready. This is the one.

20224 Sherman Unit 48, Winnetka

$1,449,000
8 Beds 5 Baths 26832777 MLS Active Status
.......Huge Price Reduction...... Main house (2 Story - 4 beds & 3 bath) & ADU (1 Story- ADU 4 beds & 2 baths) both are side by side allowing each house to have its own street access and private backyards. Newly constructed with current upgrades, vaulted ceiling, stainless steel appliances, built in conventional oven, commercial grade flooring, open floor plan, great entertainment area in the back & front of the house with built-in barbeque grill and drought resistance landscape ZERO maintenance... Main house has 2 car garage with onsite parking for 8 cars with direct Street access.... ADU has 2 car parking which is separate from the main house and it has it's own direct street access.... Each unit has it's own separate...Electric meter, Gas tankless water heater, Central heating & cooling, washer & dryer hook up....Can live in either of the house while renting out the other to long term tenant or Short term guests (via Airbnb, booking.com & VRBO) if needing the units for occasional friends or family.... The Main is perfect for a family and when the kids move out the parents can relocate to the one level ADU which is perfect for owner to occupy at a later age while collecting rental income on the main house and not having to sell while maintaining a lower property tax base *Please seek CPA advise and sale is subject to terms & conditions.

20456 W Strathern Street, Winnetka

$495,000
3 Beds 2 Baths OC26099495 MLS Active Status
Welcome to this bright and inviting 3-bedroom, 2-bath home located in a lovely neighborhood of Winnetka. Featuring a desirable first-floor entry and a spacious functional layout, this beautifully upgraded home is move-in ready and filled with natural light throughout. Fresh neutral paint enhances the warm and airy atmosphere, while walk-in closets in most rooms provide generous storage and everyday convenience. This charming residence offers comfort, style, and privacy, making it an excellent opportunity for buyers seeking a well-maintained home in a desirable setting. Situated within a gated community, residents enjoy resort-style amenities including a sparkling pool, relaxing jacuzzi, fully equipped fitness center, and playground. The HOA also covers water and trash for added ease of living. Ideally located near premier shopping, dining, and entertainment destinations such as Westfield Topanga, Northridge Fashion Center, Pierce College, and California State University, Northridge, this home truly has a lot to offer. You may just find exactly what you have been looking for.

20146 Cohasset Unit 11, Winnetka

$559,990
2 Beds 3 Baths SR26098808 MLS Active Status
Welcome to this beautifully updated townhome in the highly desirable Windsor Park community, offering resort-style living in a gated and meticulously maintained setting. This spacious 2-bedroom, 2.5-bath residence features nearly 1,600 sq.ft. of light-filled living space with an open multi-level floor plan designed for both comfort and functionality. The inviting living room showcases rich wood flooring, recessed lighting, a cozy gas fireplace, and seamless access to a private patio perfect for relaxing or entertaining. The updated kitchen is thoughtfully designed with quartz countertops, stainless steel appliances, bar seating, and an adjoining dining area, along with its own private balcony that fills the space with natural light. Overlooking the living area, the formal dining room creates an open and connected flow ideal for both everyday living and entertaining. Both bedrooms feature remodeled en-suite bathrooms, providing privacy and convenience. The spacious primary suite offers vaulted beamed ceilings and a versatile raised bonus area ideal for a home office, gym, lounge area, or creative space. Additional highlights include direct access to a private 2-car garage, side-by-side laundry area, central heating and air conditioning, ceiling fans, and ample storage throughout. Residents of Windsor Park enjoy beautifully landscaped grounds, a sparkling pool and spa, abundant guest parking, and a peaceful community atmosphere, all conveniently located near shopping, dining, schools, and public transportation.

20737 Roscoe Boulevard Unit 203, Winnetka

$699,999
3 Beds 3 Baths GD26096598 MLS Active Status
$70/ HOA and $87/ Solar Panels, HUGE SAVINGS !!! Welcome to this beautifully maintained detached home built in 1999, offering the perfect blend of comfort, style, and efficiency with a low HOA and low solar lease panels for added energy savings. This turnkey Unit 3 has been newly painted and features gorgeous hardwood floors throughout, creating a warm and inviting atmosphere from the moment you enter. The thoughtfully designed layout includes 3 spacious bedrooms—all located upstairs—and 3 bathrooms, including a convenient guest bath on the main level. The bright living area is enhanced by a cozy fireplace and recessed lighting with remote controls, perfect for relaxing or entertaining. Enjoy cooking and everyday living with all appliances included, along with a brand-new washer and dryer. Step outside to your private patio—ideal for unwinding or hosting weekend BBQs. Additional highlights include an attached 2-car garage and a central location in a desirable neighborhood close to shopping, dining, and everything you need. This home truly delivers comfort, convenience, and value all in one.

20230 Keswick Unit 3, Winnetka

$399,000
2 Beds 2 Baths 26821509 MLS Active Under Contract Status
Step into a refined and thoughtfully upgraded condominium where modern comfort meets effortless convenience. This well-maintained residence, set within a secure gated community, offers a rare blend of style, functionality, and lifestyle amenities that appeal to both homeowners and investors. Inside, brand new luxury vinyl tile flooring flows seamlessly throughout the unit, complemented by all-new plumbing for peace of mind. The living room welcomes you with soaring high ceilings and a decorative gas fireplace that adds warmth and character. The functional floor plan creates a natural harmony between the living and dining areas, ideal for both everyday living and entertaining. The kitchen is designed with practicality and ease in mind, featuring ample cabinetry, generous workspace, a stainless steel gas stove and oven, and a dedicated water filtration system for added convenience. Just beyond, a private patio or balcony provides the perfect retreat for outdoor relaxation or intimate gatherings. Comfort continues in the spacious bedrooms, each offering generous closet storage, while the bathrooms are thoughtfully designed for efficiency and daily ease. A new in-unit stackable LG washer and dryer enhances everyday living with modern convenience. This residence includes two tandem parking spaces and an additional storage unit in the community garage, ensuring ample room for your needs. The HOA delivers exceptional value, covering basic cable, internet, water, trash, and building insurance. Residents enjoy access to a suite of amenities, including a fitness center, recreational room, and a refreshing pool, creating a resort-like atmosphere right at home. Ideally situated with convenient access to shopping, dining, and major commuter routes, this property offers seamless connectivity throughout the San Fernando Valley and beyond. A rare opportunity to own a move-in ready home that effortlessly combines upgrades, amenities, and location, this condominium is truly a standout offering.

7211 Cozycroft Avenue Unit 50, Winnetka

$955,000
4 Beds 3 Baths SR26083989 MLS Active Status
Welcome to this beautiful home in the heart of the San Fernando Valley. Boasting lovely curb appeal, this charming two-story residence offers 2,109 square feet of comfortable living space designed for both everyday relaxation and effortless entertaining. The property features four spacious bedrooms and three bathrooms, including two primary suites. The inviting front exterior is highlighted by a lush lawn, a paved driveway, and mature avocado and kumquat trees. Step inside to a welcoming living room featuring the first of two decorative fireplaces and gorgeous wood flooring that flows throughout the home. The adjacent family and dining area features the second fireplace, and is finished with elegant tiling, leading into the kitchen (with granite countertops) and the downstairs primary suite. The main level hosts three bedrooms: two versatile guest rooms served by a full bathroom, and a primary bedroom with direct sliding-glass door access to the rear oasis. Upstairs, the newly carpeted second primary suite serves as a private sanctuary, complete with a full bathroom, a walk-in closet, and a private balcony overlooking the pool. The backyard is an entertainer's dream, featuring a private pool, a cozy fire pit, and dual pergolas. This low-maintenance paved space is surrounded by a mini-orchard of grapefruit, orange, tangerine, pomegranate, and sugar lemon trees. Additional amenities include a two-car garage with laundry facilities and a dedicated storage building for pool equipment. Ideally situated near Pierce College, Warner Center, and Westfield Topanga, this home offers easy access to the 101 and 118 freeways. With proximity to local parks and nature preserves, this is a rare opportunity to own a piece of the Valley. Don't let it pass you by!

20748 Vose, Winnetka

$1,449,000
8 Beds 5 Baths 25549739 MLS Active Status
.......Huge Price Reduction......Main house (2 Story - 4 beds & 3 bath) & ADU (1 Story- ADU 4 beds & 2 baths) both are side by side allowing each house to have its own street access and private backyards. Newly constructed with current upgrades, vaulted ceiling, stainless steel appliances, built in conventional oven, commercial grade flooring, open floor plan, great entertainment area in the back & front of the house with built-in barbeque grill and drought resistance landscape ZERO maintenance... Main house has 2 car garage with onsite parking for 8 cars with direct Street access.... ADU has 2 car parking which is separate from the main house and it has it's own direct street access.... Each unit has it's own separate...Electric meter, Gas tankless water heater, Central heating & cooling, washer & dryer hook up....Can live in either of the house while renting out the other to long term tenant or Short term guests (via Airbnb, booking.com & VRBO) if needing the units for occasional friends or family.... The Main is perfect for a family and when the kids move out the parents can relocate to the one level ADU which is perfect for owner to occupy at a later age while collecting rental income on the main house and not having to sell while maintaining a lower property tax base *Please seek CPA advise and sale is subject to terms & conditions.

20454 W Strathern Street, Winnetka

$399,000
2 Beds 2 Baths SR26046643 MLS Active Status
$35000 Price Reduction WOW WOW WOW Lowest Available in the complex Come see and fall in LOVE, because It all in the name…This COZY, move in ready, spacious 2 bedroom 2 bath condo is calling your name! Featuring high ceilings and a light filled layout, this open floor plan flows using a beautiful segmental archway to accent the space. Snuggle up to a sleek contemporary fireplace, whip up your best recipe in using updated kitchen appliances, and enjoy the newer flooring throughout. The spacious primary suite features a walk-in closet and a private en-suite bathroom with a vanity. The secondary bedroom is generously sized with a large closet. Looking for convenience? This home also includes an in-unit washer and dryer. Community amenities include utilities such as trash and water, along with Spectrum services available. Residents also enjoy a resort style pool & spa, fitness center, meeting room, and additional onsite laundry facilities. Located in a secure building with controlled entry and elevator access to the second floor. Secure tandem garage parking is included, with extra guest parking available. The extended parking space provide you room to store in the large shed. CASH Buyer or Buyer with down payment over 20%.

7211 Cozycroft Unit 32, Winnetka

$249,000
1 Baths SR26040172 MLS Active Status
**PRICE IMPROVEMENT** Turnkey vs fixer opportunity Welcome to this charming studio that offers a warm, inviting ambiance from the moment you enter. Ideal for first-time buyers, this thoughtfully designed open layout provides versatile living space suited for individuals, couples, or investors seeking a great rental opportunity. Perfect first step for FIRST TIME HOMEBUYERS and college students!! Located in the heart of Winnetka, you’ll enjoy convenient access to popular dining spots, neighborhood boutiques, and lively entertainment options just minutes away. With nearby major freeways, public transit, and everyday essentials close at hand, this centrally positioned home makes commuting and daily living effortless while keeping you connected to everything the city has to offer. Only 10 Minutes away from CSUN, Kaiser Permanente Medical Center, Northridge High and Reseda Park Lake! About 5-7 minutes away from Winnetka Elementary, John Middle, Northridge Hospital Medical, Pierce College and Northridge Botanical Garden!

20234 Cantara Street Unit 136, Winnetka

$299,999
1 Beds 1 Baths SR25261765 MLS Active Status
Well-maintained 1-bedroom 1st floor freshly paintedcondo offers a secured entrance and a spacious, open layout. The kitchen features granite countertops and and new dishwasher, and includes stove/range and microwave. Enjoy a dedicated dining area, an open living room, and a mix of laminate and tile flooring throughout. You’ll also have one assigned parking space and a very low HOA that includes trash, water, and sewer. The community amenities include a pool, spa, BBQ area, and shared laundry room. Centrally located on the west side of the San Fernando Valley, you’re just minutes from Warner Center, Westfield Topanga, and a wide variety of dining and entertainment. Don’t miss your chance to make this Winnetka condo your own.

20327 Saticoy Street Unit 102, Winnetka

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.