Winnetka (WIN) Homes with Gated Community Security Features

Welcome to Winnetka, California—a hidden gem nestled in the heart of Los Angeles County. Known for its charming suburban atmosphere and family-friendly environment, Winnetka offers an idyllic setting that perfectly balances the hustle and bustle of city life with the tranquility of a close-knit community.

Winnetka boasts a rich tapestry of cultural diversity, beautiful parks, and a myriad of recreational opportunities. Residents enjoy easy access to nearby attractions, including stunning hiking trails, shopping centers, and excellent dining options. The area's top-rated schools and community programs make it an ideal place for families to thrive.

One of the standout features of living in Winnetka is the availability of homes within gated communities. These exclusive neighborhoods offer an added layer of security and privacy, ensuring peace of mind for residents. With controlled access points and 24-hour surveillance, these gated communities are designed to provide a safe haven for families and individuals alike.

The homes in these secure enclaves are often beautifully designed, featuring modern amenities and spacious layouts that cater to a variety of lifestyles. Whether you’re looking for a cozy single-family home or a luxurious estate, Winnetka's gated communities have something for everyone.

Experience the charm of Winnetka, where community spirit meets modern living. Discover your dream home in one of our gated communities and enjoy the perfect blend of security, comfort, and convenience in this vibrant Los Angeles suburb. Welcome home!

Newest Winnetka (WIN) Homes with Gated Community Security Features

$475,000

2 Beds ⋅ 2 Baths ⋅ 26864991 MLS ⋅ Active Under Contract Status

Charming Gated Townhome in the Heart of Winnetka **Rare end-unit at the back of the complex** opportunity in a sought-after gated Winnetka community! This meticulously maintained two-story townhome-style condo comes with a coveted bonus: a private, oversized two-car attached garage offering direct ground-floor access ideal for everything from everyday convenience to extra storage flexibility. The main level is designed to impress. The open-concept first floor is an entertainer's dream, anchored by rich bamboo floors, a cozy fireplace, and recessed lighting, with a handy closet at the base of the stairs adding smart everyday function. The kitchen shines with newer stainless steel appliances and flows effortlessly into the dining and living areas perfect for hosting or simply unwinding. A sliding glass door opens to a private patio, made for warm summer evenings. A stylish half bath completes this level. Upstairs, you'll find 2 generously sized bedrooms, a full bath, and the ease of nearby laundry area with space for additonal storage right beside the linen closet. Both the primary and guest bedroom enjoy sliding glass door access to a long private patio a lovely spot for morning coffee or an evening spent unwinding with a good book. The primary suite also boasts a huge walk-in closet. Life here comes with resort-style perks: a sparkling pool, relaxing hot tub, recreation room, and lush green landscaping. HOA-covered water, trash, professionally maintained landscaping. With every convenience close at hand, this home truly checks every box.Don't wait homes like this move fast! Fireplace is considered decorative, seller does not know if it works!

20155 Keswick Street Unit 107, Winnetka

$459,000

3 Beds ⋅ 2 Baths ⋅ SR26146532 MLS ⋅ Active Status

Welcome to this spacious and inviting two-story condominium offering 1,340 square feet of comfortable living space in the heart of Winnetka. This well-designed home features 3 generously sized bedrooms and 2 bathrooms, providing the perfect blend of comfort and functionality. Enjoy the added bonus of both a front and private rear patio, creating ideal spaces for morning coffee, outdoor dining, or simply unwinding after a long day. Additional conveniences include a covered parking space and access to an on-site laundry room. Residents of this well-maintained community enjoy an impressive array of resort-style amenities, including two sparkling swimming pools, a fitness center, a banquet hall/clubhouse, community laundry facilities, and beautifully maintained common grounds, offering something for everyone. Ideally situated in the central San Fernando Valley, this home provides convenient access to shopping centers, restaurants, grocery stores, parks, schools, and everyday essentials. Commuters will appreciate the proximity to major thoroughfares, including the 101 and 118 Freeways, while nearby public transportation options make getting around even easier. Enjoy being just minutes from Pierce College, Westfield Topanga, Topanga Village, Warner Center, and a variety of entertainment, dining, and recreational destinations. Whether you're a first-time buyer, growing household, or investor, this home offers an exceptional opportunity to enjoy comfort, convenience, and outstanding community amenities in a desirable Winnetka location. (Some photos have been virtually staged with Ai)

20146 Cohasset Street Unit 5, Winnetka

$345,000

1 Beds ⋅ 1 Baths ⋅ SR26149183 MLS ⋅ Active Status

Condo in the City of Winnetka sounds like a Great Opportunity for a New Owner or Investor looking for Passive Rental Income. Come and Make this your Home. This Condo is has been Recently Remolded and is Turnkey Ready and it's in the City of Winnetka; just waiting for You! Secured Lobby Entrance; providing an added level of safety and security. This beautifully Well Maintained Unit Features; Spacious One Bedrooms, One Bathrooms; providing ample living space for residents, a Walk-in Closet, Plenty of Storage Space, Kitchen Granite Counter Tops, Stainless Steel Appliances including; Stove Range, an Over Range Microwave, and a Refrigerator, Dining Area with an Open Floorplan Leading into the Livingroom, along with Laminated, and Tile Flooring; combining aesthetics and easy maintenance. , Your Own Central HVAC System, Two Tandem Assigned Parking Spots, and Very Low HOA including; Trash, Water, Insurance, and Sewer. This Condo Complex offers a Community Pool, Spa, BBQ Area, and laundry room Area. Centrally Located on the Westside of the San Fernando Valley, and only minutes away from the Orange Line, Warner Center, Future Ram Headquarters, Topanga Mall, The Village at Westfield Topanga, Shopping Centers, and more! Come and Schedule your Private Viewing.

20327 Saticoy Unit 309, Winnetka

$645,000

3 Beds ⋅ 4 Baths ⋅ OC26127703 MLS ⋅ Active Status

This highly desireable Townhome has been freshly painted, includes a smart Frig, Thermostat, $8,000 of custom drapes, and a fantastic location for quick commuting through out LA. 3 bedrooms, 2 full bathrooms upstairs, 1 - 3/4 bathroom downstairs, and 1 half bath on the main floor. Nice wood floors, carpet, and tile on the main floor. Seller is getting bid/price for new carpet on the stairs and upstairs hall way. Nice garage entry on the 1st floor with laundry and a bedroom on this floor. Upstairs are 2 large bedrooms, a primary with a walkin closet, and soaking tub. The other bedroom is also oversized and has an attached full bathroom. The community has a nice club house, pool, and spa just two building away. Gated for security.

19932 Sherman Way Unit B, Winnetka

$330,000

1 Beds ⋅ 1 Baths ⋅ 26843921 MLS ⋅ Active Under Contract Status

ALL APPLIANCES INCLUDED. Charming and move-in ready 1-bedroom, 1-bath condominium featuring 630 sq. ft. of comfortable living space. This home boasts high ceilings, a cozy fireplace, and an outdoor patio, creating a bright and inviting atmosphere. Enjoy a well-appointed kitchen, spacious living area, and the convenience of a 2-car tandem community garage with in-unit washer/dryer combo. The community offers fantastic amenities including a pool, gym, and outdoor gathering spaces perfect for enjoying the California lifestyle. Located in a desirable neighborhood with easy access to shopping, dining, and major freeways, this property is ideal for first-time buyers, investors, or anyone seeking a low-maintenance lifestyle. Only three miles from Northridge Fashion Center, Westfield Topanaga Mall, CSUN and Pierce College. Don t miss the opportunity to make this cozy and stylish condo your own!

20253 Keswick Street Unit 205, Winnetka

$499,000

3 Beds ⋅ 2 Baths ⋅ 26838973 MLS ⋅ Active Status

Positioned on the top floor as a coveted corner unit, this refined Winnetka condominium offers an elevated sense of privacy, space, and modern comfort. Upon entry, the expansive living environment immediately captivates with its striking vaulted ceilings, creating an open, voluminous atmosphere rarely found in condominium living. The interior spaces flow naturally toward a private outdoor balcony, ideal for quiet morning coffee or evening relaxation.The heart of the home features a modern kitchen equipped with updated appliances and thoughtful storage, situated perfectly to serve both casual dining and larger gatherings. Laminated wood flooring runs seamlessly throughout the residence, complementing the crisp, freshly painted palette. The generous primary suite serves as a peaceful retreat, featuring a spacious layout and a dedicated primary bathroom. Two additional bedrooms provide dynamic flexibility, serving effortlessly as comfortable guest accommodations or dedicated home office spaces.Set within a secure, beautifully maintained gated community, residents enjoy access to resort-style amenities including a central swimming pool, three relaxing spa zones, manicured lush green grounds, community laundry facilities, and convenient elevator access. Complete with secured, assigned tandem parking, this pristine residence offers an effortless Southern California lifestyle within close proximity to local shopping, dining, and public parks.

20134 Leadwell Street Unit 334, 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

$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

$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 square feet of light-filled living space and an open, multi-level floor plan designed for comfort, functionality, and entertaining. The inviting living room showcases updated wood-style flooring, recessed lighting, a cozy gas fireplace, and seamless access to a private patio—perfect for relaxing, entertaining, or enjoying your morning coffee. The thoughtfully updated kitchen features quartz countertops, stainless steel appliances, bar seating, newer cabinetry and paint, and an adjoining dining area with its own private balcony that brings in abundant natural light. Overlooking the living room, the formal dining area creates an open and connected flow ideal for both everyday living and gatherings. Both bedrooms feature remodeled en-suite bathrooms, offering privacy and convenience. The spacious primary suite is highlighted by vaulted, beamed ceilings and a versatile raised bonus area that can serve as a home office, gym, lounge, reading area, or creative space. Additional improvements include a newer central A/C system, updated plumbing, partial electrical upgrades, updated flooring, recessed lighting, removal of the original popcorn ceilings, and remodeled bathrooms. Further highlights include direct access to a private 2-car garage, a side-by-side laundry area, ceiling fans, and ample storage throughout. Residents of Windsor Park enjoy beautifully landscaped grounds, a sparkling community pool and spa, abundant guest parking, and a peaceful residential atmosphere. Conveniently located near shopping, dining, schools, public transportation, and other everyday amenities, this move-in-ready townhome offers space, comfort, and community living in one complete package.

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

$420,000

2 Beds ⋅ 2 Baths ⋅ WS26073035 MLS ⋅ Active Status

First Team Real Estate welcomes you home to your private retreat in the heart of Winnetka. Tucked inside a beautifully maintained gated community, this charming 2-bedroom, 2-bathroom corner-unit condominium located on the third floor offers the perfect blend of comfort, convenience, and everyday enjoyment. This desirable corner location provides added privacy, pleasant views, and an abundance of natural light throughout. The property is currently tenant-occupied by a responsible and well-maintaining tenant who has taken excellent care of the home, making it an attractive opportunity for both investors and future homeowners. Imagine starting your mornings on your private balcony, enjoying a cup of coffee as the day begins, or unwinding in the evening in your serene living space, away from the noise of the street below. The thoughtfully designed layout features an open-concept kitchen that flows seamlessly into the living and dining areas, enhanced by higher ceilings that create an airy and inviting atmosphere. The primary suite includes its own private ensuite bathroom, while the second bedroom offers versatility—ideal for guests, a home office, or additional living space. The home also features convenient in-unit stackable laundry. The community invites you to relax and recharge with amenities including a sparkling pool and Jacuzzi—perfect for weekends or casual gatherings. With gated parking, elevator access, a furnished lobby, and well-maintained grounds, every detail is designed to make daily living effortless. Whether you are a first-time buyer searching for a place to call your own or an investor seeking a well-maintained property in a desirable location, this home presents an incredible opportunity. Ideally situated near shopping, dining, and major freeways, everything you need is just moments away. This isn’t just a condominium—it’s a place to truly feel at home.

7640 Oso Unit 318, Winnetka

Start Your Search

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.