Winding Walk Real Estate

Welcome to Winding Walk, a vibrant neighborhood located in Chula Vista, San Diego County, California. Nestled in the heart of Southern California, Winding Walk offers residents a perfect blend of suburban tranquility and urban convenience.

Situated in Chula Vista, Winding Walk is known for its family-friendly atmosphere and close-knit community. The neighborhood boasts well-maintained streets, lush green spaces, and a variety of amenities that cater to all ages. Whether you're a young professional, a growing family, or a retiree, Winding Walk has something for everyone.

One of the highlights of living in Winding Walk is its convenient location. With easy access to major highways and public transportation, residents can easily commute to neighboring cities like San Diego, National City, and El Cajon. Additionally, the neighborhood is just a short drive away from popular attractions such as the Chula Vista Marina, Aquatica San Diego, and the Otay Ranch Town Center, offering endless entertainment options.

Winding Walk is also known for its excellent schools, making it an ideal place for families. The neighborhood is served by the highly-rated Chula Vista Elementary School District and Sweetwater Union High School District, ensuring that children receive a quality education.

In terms of real estate, Winding Walk offers a variety of housing options, including single-family homes, townhouses, and apartments. The architectural styles range from modern to traditional, providing something to suit every taste and budget.

If you're looking for a welcoming community, convenient location, and a high quality of life, Winding Walk in Chula Vista, San Diego County is the perfect place to call home.

Newest Listings in Winding Walk

$710,000

3 Beds ⋅ 4 Baths

Checkout this well-designed󠃳󠂠󠂀󠂠󠃢󠂁󠂢󠃢󠂁󠂣󠃢󠂁󠂣󠃍󠂏󠃍󠂏 condo in the Winding Walk Eastlake priced in range of $699,000 - $710,000. The home offers an open-concept layout with plenty of natural light, plantation shutters, newer washer/dryer and comfortable living spaces. Newer roof has just recently installed. Enjoy the convenience of a direct-access garage with a first floor bedroom and full bath. Community amenities, including a pool and spa. Conveniently located near shopping and dining just a couple minutes walk to Otay Ranch Town Center parks, and public transportation, with easy access to nearby freeways. A great opportunity to enjoy low-maintenance living in Eastlake Chula Vista. Checkout this well-designed condo in the Winding Walk Eastlake priced in range of $699,000 - $710,000. The home offers an open-concept layout with plenty of natural light, plantation shutters, newer washer/dryer and comfortable living spaces. Newer roof has just recently installed. Enjoy the convenience of a direct-access garage with a first floor bedroom and full bath. Community amenities, including a pool and spa. Conveniently located near shopping and dining just a couple minutes walk to Otay Ranch Town Center parks, and public transportation, with easy access to nearby freeways. A great opportunity to enjoy low-maintenance living in Eastlake Chula Vista.

1622 Gila Ct Unit 168, Chula Vista

$1,049,000

4 Beds ⋅ 3 Baths

Fresh, bright, and󠃳󠂠󠂀󠂠󠃢󠂁󠂢󠃢󠂁󠂣󠃢󠂁󠂣󠃍󠂏󠃍󠂏 move-in ready in the desirable Windingwalk community. This spacious 4-bedroom, 3-bath home offers approximately 2,496 square feet with an open, comfortable layout designed for everyday living and entertaining. Recent improvements include new laminate flooring, fresh interior paint, new baseboards, updated kitchen countertops and backsplash, refreshed kitchen and bathroom fixtures, and new lighting in the entry and dining areas. The kitchen opens naturally to the main living space, while the private, low-maintenance backyard provides a comfortable setting for relaxing, dining, or entertaining. Additional highlights include central air conditioning, a dedicated laundry room, and an attached garage. Windingwalk residents also have access to community pools, parks, walking trails, and other neighborhood amenities. Conveniently located near schools, shopping, dining, and major commuter routes. Select interior and exterior photographs have been virtually staged; corresponding photographs of the homes current condition are included. Fresh, bright, and move-in ready in the desirable Windingwalk community. This spacious 4-bedroom, 3-bath home offers approximately 2,496 square feet with an open, comfortable layout designed for everyday living and entertaining. Recent improvements include new laminate flooring, fresh interior paint, new baseboards, updated kitchen countertops and backsplash, refreshed kitchen and bathroom fixtures, and new lighting in the entry and dining areas. The kitchen opens naturally to the main living space, while the private, low-maintenance backyard provides a comfortable setting for relaxing, dining, or entertaining. Additional highlights include central air conditioning, a dedicated laundry room, and an attached garage. Windingwalk residents also have access to community pools, parks, walking trails, and other neighborhood amenities. Conveniently located near schools, shopping, dining, and major commuter routes. Select interior and exterior photographs have been virtually staged; corresponding photographs of the homes current condition are included.

2372 Wander St, Chula Vista

$1,100,000

4 Beds ⋅ 3 Baths

Welcome to this beautifully maintained, move-in ready 4-bedroom home in desirable Winding Walk! Ideally situated on a corner lot, this home offers extra outdoor space, added privacy, and a wonderful floor plan designed for both everyday living and entertaining. Step inside to discover a bright, inviting interior with a spacious open-concept kitchen and family room at the back of the home. The well-appointed chefs kitchen features double ovens, a generous center island, and a breakfast bar, making meal prep and gathering with family and friends a breeze. Plantation shutters add a polished touch downstairs and in the primary suite. Upstairs, youll find four spacious bedrooms plus a convenient laundry room, providing plenty of room for family, guests, a home office, or hobbies. Recent improvements include fresh interior paint and new carpeting upstairs, giving the home an updated feel. The outdoor spaces are just as inviting. Enjoy the spacious backyard with a built-in BBQ and gas fire pit, perfect for relaxed evenings and entertaining. Around the corner, a charming courtyard patio and storage shed provide even more flexibility and functionality. Residents of Winding Walk enjoy an exceptional lifestyle with a beautiful clubhouse, pools, fitness center, and more, while the homes convenient location puts shopping, restaurants, major roadways, and the 125 toll road close at hand. Add in great schools, and this home truly has it all! Mello Roos fees with only 5 years to go. Welcome to this beautifully maintained, move-in ready 4-bedroom home in desirable Winding Walk! Ideally situated on a corner lot, this home offers extra outdoor space, added privacy, and a wonderful floor plan designed for both everyday living and entertaining. Step inside to discover a bright, inviting interior with a spacious open-concept kitchen and family room at the back of the home. The well-appointed chefs kitchen features double ovens, a generous center island, and a breakfast bar, making meal prep and gathering with family and friends a breeze. Plantation shutters add a polished touch downstairs and in the primary suite. Upstairs, youll find four spacious bedrooms plus a convenient laundry room, providing plenty of room for family, guests, a home office, or hobbies. Recent improvements include fresh interior paint and new carpeting upstairs, giving the home an updated feel. The outdoor spaces are just as inviting. Enjoy the spacious backyard with a built-in BBQ and gas fire pit, perfect for relaxed evenings and entertaining. Around the corner, a charming courtyard patio and storage shed provide even more flexibility and functionality. Residents of Winding Walk enjoy an exceptional lifestyle with a beautiful clubhouse, pools, fitness center, and more, while the homes convenient location puts shopping, restaurants, major roadways, and the 125 toll road close at hand. Add in great schools, and this home truly has it all! Mello Roos fees with only 5 years to go.

2327 Trellis St, Chula Vista

$815,000

4 Beds ⋅ 3 Baths

Highly sought-after Otay󠃳󠂠󠂀󠂠󠃢󠂁󠂢󠃢󠂁󠂣󠃢󠂁󠂣󠃍󠂏󠃍󠂏 Ranch! Impeccably maintained, this exquisite two-story home features 4 bedrooms and 3 baths in the picturesque Winding Walk community of Chula Vista. Beautifully appointed with a light, bright open floor plan ideal for everyday living and entertaining. The spacious kitchen offers rich wood cabinetry, granite countertops, stainless steel appliances and a large center island, flowing seamlessly into the dining and living areas. The living room features custom built-ins, an accent wall and large windows showcasing peaceful open views. Spacious primary suite includes a private balcony and beautifully upgraded bath with dual sinks, granite counters, stylish lighting and upgraded flooring. Two separate private 1-car garages. Additional upgrades include flooring at the stairs, washer/dryer area and first-level entrance, recessed lighting, ceiling fans and a whole-home water filtration system. Private patio provides the perfect space to relax and enjoy the views. Ideally located near top-rated schools, shopping, dining, parks and everyday conveniences.

2205 Andalusia Ln Unit 6, Chula Vista

$1,200,000

4 Beds ⋅ 3 Baths

Welcome to 1675 Picket Fence Drive, a beautifully maintained home in the highly sought-after Eastlake community of Chula Vista. Offering approximately 2,844 square feet of well-designed living space, this 4-bedroom (+ BONUS ROOM), 2.5-bath residence combines comfort, functionality, and flexibility for today's lifestyle. The inviting open floor plan features durable tile flooring throughout the main level, creating a seamless flow between the living, dining, and family rooms. The spacious kitchen is equipped with newer appliances and opens to the family room, making it ideal for both everyday living and entertaining. Upstairs, you'll find a generous primary suite complete with an en-suite bath and his and hers walk-in closets, along with spacious versatile bonus room that can easily be converted into a fifth bedroom, home office, media room, or playroom to suit your needs. Enjoy year-round comfort with a dual-zone HVAC system, providing independent climate control for each floor for increased efficiency and convenience. Outside, the private backyard offers the perfect space for relaxing, entertaining, or enjoying Southern California's beautiful weather. Ideally located near top-rated schools, parks, shopping, dining, golf, and scenic walking trails, this exceptional Otay Ranch home offers the perfect blend of space, convenience, and value. Welcome to 1675 Picket Fence Drive, a beautifully maintained home in the highly sought-after Eastlake community of Chula Vista. Offering approximately 2,844 square feet of well-designed living space, this 4-bedroom (+ BONUS ROOM), 2.5-bath residence combines comfort, functionality, and flexibility for today's lifestyle. The inviting open floor plan features durable tile flooring throughout the main level, creating a seamless flow between the living, dining, and family rooms. The spacious kitchen is equipped with newer appliances and opens to the family room, making it ideal for both everyday living and entertaining. Upstairs, you'll find a generous primary suite complete with an en-suite bath and his and hers walk-in closets, along with a versatile bonus room that can easily be converted into a fifth bedroom, home office, media room, or playroom to suit your needs. Enjoy year-round comfort with a dual-zone HVAC system, providing independent climate control for each floor for increased efficiency and convenience. Outside, the private backyard offers the perfect space for relaxing, entertaining, or enjoying Southern California's beautiful weather. Ideally located near top-rated schools, parks, shopping, dining, golf, and scenic walking trails, this exceptional Otay Ranch home offers the perfect blend of space, convenience, and value.

1675 Picket Fence, Chula Vista

1713 Cripple Creek Dr Unit 2, Chula Vista

$725,000

3 Beds ⋅ 2 Baths

PRICE IMPROVEMENT NOW󠃳󠂠󠂀󠂠󠃢󠂁󠂢󠃢󠂁󠂣󠃢󠂁󠂣󠃍󠂏󠃍󠂏 $725,000! Dont miss this exceptional opportunity to own a beautifully upgraded CORNER-UNIT townhome in highly desirable Winding Walk, Otay Ranch! Offering 1,728 sq. ft., 3 bedrooms, 2 baths, and 3 levels, this spacious home delivers the comfort and feel of a much larger residence. Step inside to an inviting open-concept layout filled with natural light, high ceilings, elegant travertine flooring, granite countertops, custom glass doors, and thoughtful upgrades throughout. The attached 2-car garage features extensive custom storage, while the water softener adds everyday convenience. Flexible living at its best: The second and third bedrooms are currently being enjoyed as a media room and dining area, creating versatile spaces that can easily be converted back to bedrooms to fit your lifestyle.Enjoy the exceptional Winding Walk lifestyle with resort-style pools, parks, walking trails, and beautifully maintained surroundings, all while being close to top-rated schools, shopping, dining, entertainment, and major transportation routes. Meticulously maintained and truly move-in ready, this is the opportunity youve been waiting for! With the new $725,000 price, this corner-unit gem offers incredible value in one of Chula Vistas most sought-after communities. PRICE IMPROVEMENT NOW $725,000! Dont miss this exceptional opportunity to own a beautifully upgraded CORNER-UNIT townhome in highly desirable Winding Walk, Otay Ranch! Offering 1,728 sq. ft., 3 bedrooms, 2 baths, and 3 levels, this spacious home delivers the comfort and feel of a much larger residence. Step inside to an inviting open-concept layout filled with natural light, high ceilings, elegant travertine flooring, granite countertops, custom glass doors, and thoughtful upgrades throughout. The attached 2-car garage features extensive custom storage, while the water softener adds everyday convenience. Flexible living at its best: The second and third bedrooms are currently being enjoyed as a media room and dining area, creating versatile spaces that can easily be converted back to bedrooms to fit your lifestyle.Enjoy the exceptional Winding Walk lifestyle with resort-style pools, parks, walking trails, and beautifully maintained surroundings, all while being close to top-rated schools, shopping, dining, entertainment, and major transportation routes. Meticulously maintained and truly move-in ready, this is the opportunity youve been waiting for! With the new $725,000 price, this corner-unit gem offers incredible value in one of Chula Vistas most sought-after communities.

1713 Cripple Creek Dr Unit 2, Chula Vista

$580,000

2 Beds ⋅ 2 Baths

SHORT SALE ACCEPTED!!!󠃳󠂠󠂀󠂠󠃢󠂁󠂢󠃢󠂁󠂣󠃢󠂁󠂣󠃍󠂏󠃍󠂏 BUYER DID NOT PERFORM!! Newer home built in 2005, with a desirable layout conveniently located near schools, shopping, park, lake, and the 125 freeway in the sought-after Winding Walk community of Eastlake. This corner unit offers added privacy and features recessed lighting, a balcony, full sized laundry, and an attached one car garage. The front of this home enjoys unobstructed views of the additional parking spaces, leased solar - add to the home's appeal - along with access to community's wonderful amenities. The super nice and motivated seller is excited to hand over the keys to the next lucky homeowner. SHORT SALE ACCEPTED!!! BUYER DID NOT PERFORM!! Newer home built in 2005, with a desirable layout conveniently located near schools, shopping, park, lake, and the 125 freeway in the sought-after Winding Walk community of Eastlake. This corner unit offers added privacy and features recessed lighting, a balcony, full sized laundry, and an attached one car garage. The front of this home enjoys unobstructed views of the additional parking spaces, leased solar - add to the home's appeal - along with access to community's wonderful amenities. The super nice and motivated seller is excited to hand over the keys to the next lucky homeowner.

2285 Whistling Ln, Chula Vista

Start Your Search

This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by San Diego MLS®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2026 San Diego MLS®,