Woodland Hills (WHLL) Homes with Two Levels Stories

Welcome to Woodland Hills, a charming enclave nestled in the heart of Los Angeles County, California. Known for its lush landscapes, vibrant community, and serene suburban feel, Woodland Hills is a hidden gem that perfectly balances the hustle and bustle of city life with the tranquility of nature. With the majestic Santa Monica Mountains as a backdrop, residents enjoy a plethora of outdoor activities, from hiking scenic trails to picnicking in local parks.

One of the standout features of Woodland Hills is its diverse real estate market, particularly its stunning two-story homes. These properties are designed to maximize space and offer a sense of grandeur, making them ideal for families and individuals alike. With spacious layouts, these homes often boast open-concept living areas, gourmet kitchens, and luxurious master suites, providing both comfort and style. The two-level design not only enhances the aesthetic appeal but also offers functional living spaces that cater to modern lifestyles.

Living in Woodland Hills means being part of a vibrant community with access to top-rated schools, shopping centers, and dining options. The neighborhood is known for its friendly atmosphere and strong sense of community, making it a wonderful place to call home. Whether you’re enjoying a leisurely stroll through tree-lined streets or hosting a gathering in your beautifully designed two-story home, Woodland Hills offers an unparalleled quality of life. Discover your dream home in this idyllic region and experience all that Woodland Hills has to offer!

Newest Woodland Hills (WHLL) Homes with Two Levels Stories

$2,549,000

6 Beds ⋅ 7 Baths ⋅ IG26175993 MLS ⋅ Coming Soon Status

Experience elevated living in this Italian-French villa-inspired estate, where timeless architecture, impressive scale, and resort-style amenities come together to create an exceptional Southern California lifestyle. Designed to embrace its surroundings, the residence offers beautiful views from multiple sides, soaring ceilings, elegant Italian columns, crown molding, rich African Cherry hardwood flooring, and an abundance of natural light. The home features 6 bedrooms and 6.5 bathrooms, with en-suite accommodations and private balconies, offering comfort and privacy for family and guests alike. The luxurious primary retreat provides its own fireplace and spa-inspired bath with a Jacuzzi tub, creating a peaceful sanctuary at the end of the day. Three fireplaces throughout the residence add warmth and ambiance, while a spacious bonus room offers flexibility for a home office, gym, media room, or additional living space. At the heart of the home, the kitchen is appointed with Thermador appliances, granite surfaces, and a generous pantry, creating an inviting setting for both everyday living and sophisticated entertaining. A surround-sound system further enhances the home's entertainment experience. Step outdoors and discover your own private resort-style escape. Spend sun-filled afternoons beside the gas-heated pool and spa, wander through mature landscaping filled with an extraordinary collection of fruit trees, including pear, guava, fig, lemon, pomegranate, peach, apricot, plum, olive, cherry, jujube, and more bringing the charm of a private Mediterranean garden to your backyard. Thoughtful amenities include a 4-car garage with tandem parking, two EV chargers, dual-zone HVAC, a new tankless water heater, water softener and filtration system, dual-pane windows, security cameras and system, abundant storage, and upstairs laundry. A new 2026 roof with a 10-year warranty adds another meaningful upgrade. Grand yet inviting, private yet designed for entertaining, this distinctive estate offers more than a beautiful home; it delivers a lifestyle of comfort, elegance, and resort-inspired living.

5369 Medina Road, Woodland Hills

$2,799,000

6 Beds ⋅ 6 Baths ⋅ 26870583 MLS ⋅ Coming Soon Status

Elevate your lifestyle in this meticulously reimagined South of the Boulevard retreat, where the effortless coastal sophistication of Malibu meets the refined tranquility of Woodland Hills. Spanning over 4,500 square feet, the residence is a masterclass in organic modernism, defined by artisanal Roman Clay finishes that bathe the interiors in a soft, tactile warmth.The heart of the home centers on a chef's kitchen equipped with professional-grade Thermador appliances, flowing seamlessly into airy living spaces designed for high-end entertaining. Five generous ensuite bedrooms offer ultimate privacy, including a primary sanctuary featuring a spa-inspired bath and a private balcony for morning coffee.Outside, the grounds transform into a private resort. A designer pool and spa with an expansive baja shelf are framed by sculptural olive trees and manicured landscaping.

22269 Avenue San Luis, Woodland Hills

$1,950,000

4 Beds ⋅ 5 Baths ⋅ SR26175458 MLS ⋅ Active Status

Completely remodeled Mid-Century modern pool home desirably located on an approx. 13,000 SF lot West of Valley Circle on a quiet street adjacent to Hidden Hills. The property is set back with expansive frontage including new sprawling synthetic lawns, olives, & full growth trees that provide a serene & private feel. A newly paved driveway leads to the 2-car garage with epoxy flooring & direct access. Newly added cement steps with accent lighting ascend to a grand covered entry with newly tiled front porch. Step through a double door entry to find completely remodeled interiors flooded with natural light. Oversized living room features plaster finished fireplace & sliding glass door that opens to the yard. Separate formal dining room has second glass slider that opens to the yard & direct kitchen access. Remodeled kitchen boasts quartz counters, soft close cabinetry, new stainless appliances, double ovens, large peninsula with bar top seating, walk-in pantry, & another glass slider. The kitchen opens to a separate family room/den with fully remodeled bathroom providing ideal flex space for office or potential downstairs bedroom suite. Upstairs you will find four generous sized bedrooms each with custom closets & access to their own en-suite bathrooms. Luxurious primary features wall-to-wall windows overlooking lush grounds, large walk-in closet with custom built-ins, & gorgeous remodeled bathroom with fluted vanity, dual sinks, & walk-in shower with designer tiling, raindrop shower head, & bench seat. Second bedroom suite has walk-in closet & private bathroom with dual sinks & bath tub with shower. Two additional secondary rooms each have spacious closets & share en-suite new bathroom with walk-in shower. There’s also a convenient indoor laundry room with built-in cabinetry. Entertainer’s backyard is highlighted by remodeled pebble finished swimming pool with Baja ledge, newly built spa with spillover waterfall, large cement patio for outdoor dining, newly added synthetic lawns for play with putting green, outdoor pool bathroom with walk-in shower, new vinyl fencing, lush landscaping & accent lighting. Additional system upgrades per seller: new roof, HVAC system, electrical panel, & all new pool equipment with smart app controls. Adjacent to fine dining/shopping, Westfield Mall/Village, Calabasas Commons, Warner Center with the new Rams Village in development, local parks/hiking trails, & zoned for award-winning El Camino & Hale charter schools.

5789 Fairhaven Avenue, Woodland Hills

$545,000

2 Beds ⋅ 2 Baths ⋅ SR26173068 MLS ⋅ Active Status

Welcome to this desirable and rare 2 bedroom plus loft and 2 bath condo in the exclusive, gated community of The Met! Beautifully updated top floor unit enjoys a loft that is perfect for an office, for an extra guest or a play room! The open floor plan has abundant natural light in every room. The spacious kitchen features stainless steel appliances, refrigerator and granite countertops. Enjoy updated floorings, lighting and an in-unit washer and dryer. Living room opens to a balcony with a storage closet and view of tree tops. The fireplace is perfect addition for those cooler evening. The Met offers a resort-style living with landscaped grounds and a host of amenities: including 4 sparkling pools, spas, saunas, a steam room, underground racquetball and basketball courts, fitness center, 6 tennis courts, and a children's playground and pool table in clubhouse. There are 2 subterranean garage parking spaces. With 24-hour gated security, this community provides peace of mind and an exceptional lifestyle.

21500 Burbank Unit 328, Woodland Hills

$1,360,000

4 Beds ⋅ 3 Baths ⋅ 26869603 MLS ⋅ Active Status

This beautifully updated 4-bedroom, 2.5-bath Cape Cod was made for entertaining. The living, dining and kitchen spaces come together around a show-stopping 9-foot Calacatta quartz island. The open floor plan is big enough for a house full of friends, yet intimate enough for just the family. The main living spaces open to the private backyard, creating a great indoor-outdoor flow. Major updates include new HVAC and ducting, a 2-year-old roof, updated plumbing and electrical panel. Incredibly inviting and ready to enjoy, in a quiet Woodland Hills neighborhood near Westfield Topanga, The Village and the new Rams development.

6460 Penfield Avenue, Los Angeles

$1,899,000

4 Beds ⋅ 4 Baths ⋅ SR26171213 MLS ⋅ Active Status

Perched high above the San Fernando Valley on a quiet cul-de-sac in one of Woodland Hills-South's most coveted hillside neighborhoods, this exceptional 4-bedroom, 4-bathroom family home offers approximately 2,862 square feet of meticulously remodeled living space on an expansive 17,403-square-foot lot, showcasing breathtaking, irreplaceable panoramic views that steal the show. From virtually every room and nearly every corner of the property, enjoy sweeping vistas across the San Fernando Valley, spectacular daily cotton candy sunsets, and a mesmerizing display of twinkling city lights that create an unforgettable backdrop from sunrise to nightfall. Thoughtfully reimagined from top to bottom with designer-quality finishes, the light-filled floor plan is designed to maximize the incredible views while offering multiple living areas, formal dining, and a beautifully remodeled chef’s kitchen featuring quartz countertops, custom cabinetry, stainless steel appliances, an oversized serving peninsula, and a sunny breakfast area. The luxurious primary suite is a private retreat with its own view balcony, walk-in closet, and spa-inspired bathroom, while a remodeled downstairs bedroom and full bath provide ideal accommodations for guests or multigenerational living. Completing this remarkable offering is a resort-inspired backyard with a stunning rock waterfall swimmer’s pool and spa, expansive entertaining patios, lush mature landscaping, and an exceptional sense of privacy and exclusivity, creating the ultimate setting for luxurious California indoor-outdoor living.

4525 Tenango Drive, Woodland Hills

$1,599,000

5 Beds ⋅ 4 Baths ⋅ SR26171202 MLS ⋅ Active Status

Modern contemporary architecture, resort-inspired living, and timeless design come together in this extraordinary 5 bedroom and 4 bathroom family home, thoughtfully reimagined with an uncompromising vision and true pride of ownership. Created as the sellers’ dream home without a budget, every detail has been carefully curated to deliver exceptional quality, sophisticated style, and effortless indoor-outdoor living. Expansive walls of glass, soaring ceilings, and designer finishes fill the home with natural light, while the open-concept floor plan flows seamlessly into a stunning chef’s kitchen featuring sleek cabinetry, quartz countertops, premium stainless steel appliances, and generous entertaining spaces perfect for family and friends. The luxurious primary suite offers a serene retreat with a beautifully renovated spa-inspired bathroom, complemented by spacious secondary bedrooms and stylishly updated baths. Outside, the lavishly landscaped grounds were thoughtfully designed with love and intention, showcasing lush turf, sculptural succulents, mature trees, drought-tolerant landscaping, and multiple outdoor living spaces that surround the sparkling remodeled pool, covered patio, fire pit, and expansive grassy yard, creating a private resort-like setting. Extensive renovations and system upgrades completed from 2004 through 2026 provide peace of mind and reflect years of meticulous investment and craftsmanship. Ideally situated in an A+ neighborhood adjacent to the exceptional shopping, dining, parks, hiking trails, and endless amenities of both Calabasas and Woodland Hills, this is far more than a beautifully remodeled home—it’s an exceptional lifestyle property where luxury, comfort, and enduring quality come together in one unforgettable offering.

4391 Pampas Road, Woodland Hills

$1,595,000

4 Beds ⋅ 4 Baths ⋅ 26862529 MLS ⋅ Active Status

20727 Dolorosa Street is a 4 bedroom, 3.5 bath home where high ceilings and a striking architectural staircase define the main living space. Just off the main living area, a versatile bonus room offers the flexibility to serve as a home office, gym, media room, playroom, or guest space. Open living areas create a natural flow for everyday living and entertaining. The kitchen features built-in appliances, custom cabinetry, and quality finishes throughout. New flooring, a new roof, and carefully selected upgrades complete the home. Outside, the covered patio and peaceful green views create the perfect setting for entertaining, relaxing, or watching the sunset. Ideally located just minutes from Ventura Boulevard, Westfield Topanga, The Village, restaurants, shopping, and the 101 Freeway, this home puts the best of Woodland Hills within easy reach.

20727 Dolorosa Street, Woodland Hills

$1,350,000

2 Beds ⋅ 1 Baths ⋅ SR26171134 MLS ⋅ Active Status

Nestled within the coveted Girard Tract, this enchanting storybook-inspired vintage residence is surrounded by lush, park-like grounds and showcases breathtaking, panoramic Valley views. Set on an expansive approximately 12,000-square-foot property with nearly 175 feet of street frontage, this exceptional offering includes two additional separate lots, presenting a rare opportunity for investors, builders, or owner-users seeking to create a truly extraordinary estate. Towering mature trees, manicured gardens, and picturesque landscaping provide a private, tranquil setting that feels worlds away from the city, while remaining just minutes from Woodland Hills' premier shopping, dining, and entertainment. The charming existing home exudes warmth and character, offering timeless appeal with remarkable potential to expand or reimagine, following the example of the larger luxury residences that define this highly sought-after neighborhood. Whether you're looking to preserve its vintage charm, renovate, or build your dream home, this is a rare chance to own one of the most unique view properties in one of Woodland Hills' most desirable enclaves.

4924 Drive Alatar, Woodland Hills

$5,600,000

7 Beds ⋅ 7 Baths ⋅ SR26157820 MLS ⋅ Active Status

Set on a quiet street south of Ventura Boulevard, 4744 Vista De Oro is a thoughtfully designed modern organic estate where timeless architecture meets exceptional craftsmanship. Framed by mature olive trees, smooth white stucco, natural stone, and dramatic gabled rooflines, this newly constructed residence offers refined luxury with effortless California living. A circular driveway and attached two-car garage create an impressive arrival. Inside, soaring ceilings, wide-plank white oak floors, hand-applied Venetian plaster, custom decorative plaster finishes, and seamlessly integrated mudded recessed lighting create a warm, gallery-inspired aesthetic throughout. The expansive great room is anchored by a statement fireplace and opens through walls of sliding glass to the backyard. At the heart of the home, the designer kitchen features an oversized Taj Mahal quartzite island and Taj Mahal countertops, premium Graff faucets, professional-grade appliances, custom cabinetry, and a fully equipped butler's pantry with prep kitchen. The formal dining room is highlighted by a custom glass wine display and artisan plaster feature wall, while the main level also offers a private theater, dedicated office, designer powder room, and an ensuite guest bedroom. Upstairs, a light-filled loft opens to a covered terrace, while the luxurious primary suite offers vaulted ceilings with exposed beams, a fireplace, sitting area, wet bar, private balcony, spa-inspired bath, and an expansive boutique-style dressing room. Three additional ensuite bedrooms complete the upper level. Designed for year-round entertaining, the private backyard features a sparkling pool and spa, expansive grassy lawn, built-in outdoor kitchen, covered patio, custom firepit lounge, and multiple gathering spaces. A detached ADU with its own bedroom, bath, kitchen, and living area provides exceptional flexibility for guests, extended family, or a private office. Additional highlights include a fully integrated Control4 smart home system and premium designer finishes throughout. Conveniently located just minutes from the newly reimagined Westfield Topanga, Calabasas Commons, and a short drive to the world-famous beaches of Malibu.

4744 Vista De Oro Avenue, Woodland Hills

$675,000

2 Beds ⋅ 2 Baths ⋅ 26868075 MLS ⋅ Active Status

Step into this stunning Woodland Hills townhome that truly defines modern Southern California living. This exquisite two-bedroom, two-bathroom residence welcomes you through a charming private patio before unveiling a beautifully remodeled interior that blends every day sophistication and comfort. From the moment you enter, you'll be greeted by beautiful high ceilings and an abundance of natural light, creating an inviting, sun-drenched ambiance throughout every room. The thoughtfully designed open floor plan ensures effortless flow between the main family room, dining area, and upgraded kitchen. Upstairs, discover two generously sized bedrooms, each hosting its own dedicated bathroom. The convenience continues with your own attached two-car garage. Step outside to enjoy the lush, meticulously landscaped community grounds, where a sparkling pool and rejuvenating spa can be found. Set in a sought-after Woodland Hills neighborhood, this exceptional townhome offers a harmonious blend of style and functionality.

6241 Nita Avenue, Woodland Hills

$669,000

2 Beds ⋅ 3 Baths ⋅ SR26165354 MLS ⋅ Active Status

Some places remind you why where you live matters. Warner Village III has long been one of Warner Center’s most sought-after communities, offering something increasingly rare: a peaceful, garden-inspired setting in the heart of Woodland Hills. Meandering streams, mature trees, charming bridges, and beautifully landscaped walking paths create an environment that encourages you to slow down, take an evening stroll, or simply enjoy your morning coffee surrounded by greenery. This rarely available Plan C enjoys a tranquil location within the community, where garden views and lush landscaping create a welcome sense of privacy. Yet just moments away, you’ll find The Village at Topanga, Westfield Topanga, Warner Center Park, restaurants, cafés, shopping, grocery stores, fitness studios, and entertainment. Here, nature and convenience exist side by side. Inside, nearly 1,900 square feet of thoughtfully designed living space is filled with natural light from soaring vaulted ceilings and expansive windows. Wood flooring, plantation shutters, recessed lighting, generous storage, newer HVAC system (installed 2020) and multiple private patios create a warm, inviting atmosphere for everyday living and entertaining. Upstairs, both bedrooms feature en-suite bathrooms, including a spacious primary suite with a walk-in closet, private balcony, and peaceful garden views. The oversized lower-level bonus room offers exceptional flexibility as a media room, home office, fitness space, guest retreat, or potential third bedroom. An oversized attached two-car garage with direct access provides outstanding convenience and additional storage. Residents enjoy pools, spas, a tennis court, recreation room, beautifully maintained grounds, and scenic walking paths throughout the community. HOA dues include water, sewer, basic cable, high-speed internet, and earthquake insurance. Warner Village III is also an FHA-approved community, providing financing flexibility that’s increasingly difficult to find in Warner Center. More than a home, this is a lifestyle where peaceful surroundings and everyday convenience come together, making it easy to enjoy the best of both nature and city living. Assessor data states square footage as 1,526SF which is believed not to include the downstairs bonus room. Builder Floor Plan attached with estimated square footage listed as 1,870sf. Buyer to verify.

21901 Burbank Boulevard Unit 218, Woodland Hills

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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.