Winter Garden/Oakland Townhomes for Sale

Winter Garden/Oakland Townhomes for Sale

**Discover the Enchantment of Winter Garden and Oakland, Florida**

Nestled in the heart of Orange County, Winter Garden and its charming neighbor, Oakland, offer a captivating blend of small-town charm and modern convenience. Known for its picturesque landscapes and vibrant community spirit, this region boasts a rich history that dates back to the early 1900s, making it a delightful place to call home.

Winter Garden is renowned for its historic downtown area, where brick-lined streets are adorned with unique shops, delightful cafes, and the celebrated Plant Street Market. Residents enjoy a variety of outdoor activities, thanks to the stunning West Orange Trail that winds through the area, perfect for walking, jogging, or biking. The community also hosts numerous events throughout the year, fostering a close-knit atmosphere that welcomes newcomers with open arms.

Just a stone's throw away, Oakland offers a tranquil escape with its lush greenery and serene lakes. This quaint town is perfect for those seeking a peaceful lifestyle while still being in proximity to the vibrant amenities of Winter Garden.

For those considering a move to this enchanting region, the townhomes for sale in Winter Garden and Oakland present an incredible opportunity. These modern residences often feature spacious layouts, contemporary finishes, and community amenities that cater to a variety of lifestyles. Whether you’re looking for a cozy retreat or a bustling family home, the townhomes here provide the perfect backdrop for creating lasting memories.

Embrace the charm of Winter Garden and Oakland—where history meets modern living, and every day feels like a vacation. Explore the townhomes for sale today and discover your dream home in this delightful Florida gem!

Newest Winter Garden/Oakland Townhomes for Sale

3 Beds ⋅ 3 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code

Virtually Staged. **Virtually Staged | Tenant Occupied | Great Investment Opportunity** Beautiful two-story home in the desirable Storey Grove community in Winter Garden, currently rented for the full year—ideal for investors seeking immediate rental income. This home offers 3 bedrooms, 2.5 bathrooms, approximately 1,717 sq. ft. of living space, peaceful pond views, and a detached two-car garage. The open-concept layout features a kitchen with island overlooking the family and dining areas. Upstairs, the primary suite includes an oversized bathroom and walk-in closet. Residents enjoy a clubhouse, fitness center, resort-style pool, hedge maze, and dog park. Conveniently located near SR-429, US-192, and SR-545, just minutes from Walt Disney World, Orange County National Golf Center, shopping, dining, and Walmart. A great opportunity in one of Winter Garden’s most sought-after communities.

11367 Great Rock Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

MOVE-IN READY! BRAND-NEW CONSTRUCTION, NEVER LIVED IN! Located in the highly desirable Waterleigh community in Winter Garden, this beautiful Ibis townhome offers 3 bedrooms, 2.5 bathrooms, a one-car garage, and a long driveway providing additional parking space. With modern finishes and a bright, open-concept design, this home is ready for its first owner! Step inside through the welcoming foyer and into an open living space where the kitchen, dining area, and living room flow seamlessly together. The kitchen features upgraded stainless steel appliances, quartz countertops, ample cabinetry, and convenient bar seating, making it ideal for everyday living and entertaining. The living area overlooks a covered patio, offering additional space to relax and enjoy the Florida lifestyle. A powder room and rear-entry garage complete the first floor. Upstairs, you’ll find all three bedrooms, two full bathrooms, and a conveniently located laundry room. The spacious primary suite features a walk-in closet, double-sink vanity, and generously sized shower. Two additional bedrooms and a full guest bathroom provide flexibility for family, guests, or a home office. The home also includes a Smart Home technology package, allowing convenient control of compatible home features from your smart device whether you’re home or away. Located in Waterleigh, one of Horizon West’s sought-after master-planned communities, residents enjoy an exceptional lifestyle with resort-style amenities and convenient access to shopping, dining, entertainment, and major Central Florida destinations. SR-429 is nearby, providing easy connectivity throughout the Orlando area. With attractive curb appeal, modern finishes, newer construction, and a low-maintenance townhome lifestyle, this Ibis offers an excellent opportunity to own a move-in-ready home in Winter Garden. Schedule your private showing today!

16570 Barbours Creek Way, Winter Garden

3 Beds ⋅ 4 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code

Downtown Winter Garden becomes part of everyday life at this one-of-nine residence at 30 North Park, where a covered balcony overlooks the West Orange Trail and Plant Street’s dining, shops, and gathering spots are only a short stroll away. Arranged across three thoughtfully designed levels, the home balances connected gathering spaces with room to work and unwind. The main level brings the kitchen, dining area, and living room together beneath tall ceilings. An oversized island anchors the kitchen, complemented by quartz countertops, tall two-tone cabinetry, stainless steel appliances, and natural-gas cooking. Decorative wood beams, built-ins, and a gas fireplace feature wall give the living room character, while sliding glass doors extend the space to the balcony. Each of the three bedroom suites includes a walk-in closet and private full bathroom. Two suites occupy the upper level, including the primary with fitted closet storage, dual sinks, a glass-enclosed shower, and a separate water closet, while the second-level suite is currently arranged as a window-lined office. A ground-level bonus room with an adjoining fourth full bath creates another adaptable space for media, fitness, hobbies, or guests. Engineered hardwood and designer tile keep the interior carpet-free, while upper-level laundry, a tankless water heater, zoned HVAC, spray-foam ceiling insulation, and an attached rear-entry two-car garage add practical convenience. From quiet time on the balcony to mornings on the trail and evenings along Plant Street, this home pairs polished, flexible interiors with a distinctly downtown Winter Garden lifestyle.

72 N Park Avenue Unit 8, Winter Garden

2 Beds ⋅ 3 Baths ⋅ Signature Lakes Parcel 1b SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained 2 bedroom, 2 bath townhome in the highly sought-after Independence community at Signature Lakes. This home offers a bright, open layout with comfortable living spaces perfect for both everyday living and entertaining. The kitchen flows seamlessly into the dining and living areas, creating a welcoming atmosphere filled with natural light. Both bedrooms are generously sized, offering privacy and flexibility for guests, a home office, or a cozy retreat. The attached 2-car garage provides secure parking and additional storage—an added convenience rarely found in townhome living. The HOA includes internet access, pest control, ground maintenance and access to the pool, clubhouse and fitness center. Independence is known for its peaceful surroundings, well-kept landscaping, and prime location near top Winter Garden attractions and highly rated schools. Enjoy easy access to major highways, shopping, dining, and the vibrant Hamlin and Horizon West areas. Whether you're relaxing at home or exploring everything the community has to offer, this townhome delivers comfort, convenience, and a true sense of home. Come experience the lifestyle waiting for you at Independence.

14766 Peekskill Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2e SubDv. ⋅ 34787 Zip Code

This stylish townhome in one of Winter Garden’s most desirable resort-style communities, offers a blend of comfort, convenience, and everyday luxury. The home sits in a beautifully planned neighborhood known for its amenities,GainesvillecinfgainesLoo surroundings, and welcoming atmosphere—an ideal setting for anyone seeking a relaxed yet connected lifestyle. Its location is a major highlight. Winter Garden is home to some of Central Florida’s top-rated schools, making this property especially appealing for families who value strong educational options. You’re also just minutes from premier shopping and dining at places like Hamlin Town Center and Winter Garden Village, giving you easy access to everything from groceries to entertainment. And of course, the magic of Disney theme parks is right around the corner, making weekend outings effortless and adding a touch of excitement to everyday life. This townhome places you in a thriving, fast-growing area where convenience meets resort-style living. With beautiful community amenities, excellent schools, nearby shopping, and world-famous attractions close enough to enjoy anytime, it’s a standout opportunity in one of Winter Garden’s most sought-after.

10119 Salt Point Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Westside Townhomes Phase 2 19/100 Lot 5 Blk 11 SubDv. ⋅ 34787 Zip Code

Beautiful Family-Oriented Townhouse in a Great Location! Well-maintained and move-in ready, this home offers low-maintenance living with a low HOA fee. Conveniently located approximately 10–17 miles from Walt Disney World, Disney Springs, and many of Orlando’s top entertainment destinations. Easy access to major highways makes commuting and exploring the area convenient. A wonderful opportunity for a family, second home, or investment property. More photos coming soon!

988 Stucki Terrace, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

Welcome home to a place where life feels just a little easier. Tucked inside the peaceful Westbrook community of Winter Garden, this beautifully maintained, move in ready townhome offers the perfect blend of comfort, style, and convenience. Step inside to discover an inviting open living and dining space that naturally brings everyone together. The heart of the home is the kitchen, thoughtfully designed with gleaming granite countertops, stainless steel appliances, a contemporary tile backsplash, and plenty of space to prepare everything from quick weekday breakfasts to weekend gatherings with friends. Stylish upgraded lighting throughout adds a fresh, modern touch to every room. Upstairs, all three bedrooms create a private retreat away from the main living areas. The spacious primary suite is designed for relaxation and features dual walk in closets, giving everyone room to stay organized. With two additional bedrooms and two and a half bathrooms, there's plenty of flexibility for family, guests, or a dedicated home office. Behind the scenes, a newer high efficiency HVAC system with a UV germicidal light provides year round comfort and added peace of mind. Outside your front door, you'll love being just minutes from Winter Garden Village, the award winning shops and restaurants of Historic Downtown Winter Garden, and the excitement of Disney Springs. Easy access to SR 429 puts Orlando, Tampa, and Central Florida's top attractions within easy reach, making both your daily commute and weekend adventures effortless. Beautiful, meticulously cared for, and ideally located, this is more than a townhome. It's the beginning of your next chapter. Schedule your private showing today.

1017 Priory Circle, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code

Luxury living in the ENZO Model townhome located in Lakeshore Preserve, a Toll Brothers community surrounded by million-dollar homes in Winter Garden. This spacious executive style townhome offers 5 bedrooms, 4 bathrooms, and over 3,100 square feet of living space, including a private 1-bedroom apartment with kitchenette above the garage and its own private entrance perfect for guests, multigenerational living, or a student retreat. Built in 2017, this home features an open concept layout, Wolf gas cooktop, two gas tankless water heaters, whole home water softener, and two A/C systems with Nest thermostats. Recent updates include luxury vinyl flooring throughout the downstairs, all new carpet installed upstairs and in all bedrooms, and plantation shutters, adding both style and functionality. The home has also been upgraded with over $20,000 in custom closet systems, providing exceptional storage, organization, and convenience throughout. Enjoy the extended wrap around front porch, private courtyard, and even views of Disney fireworks and space launches from the front of the home. Lakeshore Preserve offers resort style amenities including a lakefront clubhouse, fitness center, pool, lake access, kayak launch, volleyball court, firepit, and dog park. Conveniently located near Disney, Hamlin shopping and dining, Flamingo Crossings, Orlando Health, and top rated schools. HOA includes exterior maintenance, cable, internet, and community amenities. A rare opportunity to own a luxury townhome in one of Winter Garden’s most desirable communities.

8866 Bismarck Palm Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code

Almost New & Move-In Ready! Built in 2024, this beautifully maintained corner-unit townhome offers the perfect combination of modern style, comfort, and functionality. Featuring 4 full bedrooms and 3 full bathrooms, the thoughtfully designed floor plan includes a convenient first-floor bedroom, ideal for a home office, guest suite, or private bedroom. The home showcases upgraded tile flooring throughout the main living areas and stylish granite countertops, creating a clean and contemporary feel. The spacious kitchen comes fully equipped with stainless steel appliances, including refrigerator, microwave, and dishwasher, plus a washer and dryer for added convenience. Enjoy Florida living from the screened-in back porch, perfect for relaxing or entertaining while enjoying the outdoors. A private 2-car garage located at the rear of the home provides secure parking and additional storage. Residents enjoy an impressive selection of community amenities, including a resort-style pool, fitness center, gathering area, playground, and community mailbox. With its desirable corner-unit location, modern finishes, flexible first-floor bedroom, and excellent amenities, this almost-new townhome is an exceptional opportunity for both homeowners and investors. Come see why this beautiful 2024 townhome is the perfect place to call home!

14075 Lochend Way, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code

BACK ON THE MARKET WITH A PRICE IMPROVEMENT! Don’t miss this highly upgraded Toll Brothers townhome in Westhaven at Ovation. Built in 2024, this popular floor plan that is NO LONGER AVAILABLE FROM THE BUILDER. The open-concept main level features a beautifully upgraded kitchen with quartz countertops, designer cabinetry and backsplash, stainless steel appliances, and an oversized island. Step outside to your private courtyard featuring a hot tub that can come along—perfect for relaxing and enjoying the Florida lifestyle. Additional upgrades include upgraded finishes throughout. Upstairs, the spacious primary suite offers a walk-in closet and upgraded en-suite bath, plus two additional bedrooms. Located approximately 2 MINUTES FROM THE NEARBY ELEMENTARY SCHOOL and close to Horizon West, Hamlin, shopping, dining, entertainment, and major roadways. Multiple upgrades, included spa, prime Winter Garden location, and a floor plan you can no longer purchase from the builder!

13953 Easdale Alley, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code

Welcome to 1511 Sweet Apple Street, a well-maintained, stunning, and ready-to-move-in townhouse located in the highly desirable Longleaf at Oakland community. Built in 2019, this beautifully maintained home offers 3 spacious bedrooms, 2.5 bathrooms, and 1,620 square feet of bright, open-concept living space designed for both relaxation and entertaining. The inviting front porch is the perfect place to enjoy your morning coffee. Inside, abundant natural light flows through the numerous windows, enhancing the spacious open-concept layout. The large and contemporary kitchen features an island, stainless steel appliances, granite countertops, and an oversized pantry, with premium finishes that seamlessly flow into the main living and dining areas, making it ideal for both everyday living and entertaining. Upstairs, the primary suite serves as your private retreat, featuring an En-suite bath and ample closet space, alongside two additional bedrooms perfect for family, guests, or a dedicated home office. Step outside to the private courtyard, perfect for grilling and enjoying Florida’s beautiful weather with plenty of space for outdoor seating or even a hot tub. The two-car garage offers private rear entry into the home with a spacious driveway that provides additional parking along with guest parking nearby. There is additional parking in the front of this home also. Enjoy being just steps away from the beautiful community pool overlooking the pond and the neighborhood playground. This home and community provides everything the Florida Lifestyle has to offer ! Living here means embracing an incredible Central Florida lifestyle. The Longleaf community features a sparkling resort-style pool with a cabana, a playground, and scenic walking paths. Best of all, you are just steps away from the historic West Orange Trail and the Oakland Nature Preserve, making outdoor adventures effortless. When you want to head out for dinner or shopping, the vibrant culture of downtown Winter Garden and the famous Plant Street Market are only minutes away. Plus, with quick access to major highways like the Florida Turnpike and SR-429, you are seamlessly connected to all of Orlando's world-class theme parks, dining, and entertainment. Don't miss the opportunity to make this beautiful turnkey property your own!

1511 Sweet Apple Street, Oakland

3 Beds ⋅ 3 Baths ⋅ Mezzano Townhomes SubDv. ⋅ 34787 Zip Code

Welcome to this modern two-story townhome in Winter Garden. 2,024 square feet of interior living space, this home features 3 bedrooms and 3 full bathrooms, including a primary suite on the upper level and a full bedroom with a full bathroom conveniently located on the main level. The open-concept layout seamlessly connects the kitchen, dining, and gathering areas, creating an inviting space for daily living and entertaining. The kitchen is outfitted with quartz countertops, 42-inch cabinetry with crown molding, and a multi-functional center island. Additional highlights include an upper-level loft, a dedicated laundry room, smart home technology, and a private paver courtyard connecting the residence to a detached two-car garage equipped with an electric vehicle charging outlet. Residents enjoy access to community amenities, including a swimming pool and playground, with convenient proximity to local shopping, dining, and major thoroughfares.

7025 Twilight Bay Drive, Winter Garden

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