Winter Garden/Oakland Homes with Golf Community Features

Winter Garden/Oakland Homes with Golf Community Features

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant locale is renowned for its picturesque landscapes, charming downtown area, and a rich tapestry of outdoor activities, making it an ideal destination for families, retirees, and golf enthusiasts alike.

Winter Garden boasts a delightful blend of historic charm and modern conveniences. Stroll through the beautifully restored downtown, where you can explore boutique shops, savor delicious cuisine at local eateries, and enjoy the lively atmosphere of weekly farmers' markets. The area is also home to a variety of parks and recreational facilities, perfect for those who appreciate the great outdoors.

For golf lovers, the Winter Garden/Oakland area is a true paradise. With several stunning golf communities, residents can enjoy access to meticulously maintained courses that cater to all skill levels. Imagine waking up to the serene views of lush fairways and rolling greens right outside your window. These golf communities offer not just homes, but a lifestyle centered around leisure and camaraderie. Many properties feature luxurious amenities such as clubhouses, swimming pools, and fitness centers, providing a perfect blend of relaxation and recreation.

Whether you are looking for a cozy single-family home or an elegant estate, Winter Garden and Oakland offer a diverse selection of properties to suit your needs. Embrace the Florida sunshine and discover the charm of this thriving community, where every day feels like a vacation. Experience the joy of living in a golf community that truly embodies the spirit of Florida living!

Newest Winter Garden/Oakland Homes with Golf Community Features

3 Beds ⋅ 3 Baths ⋅ Summerlake Grvs Ph 2 SubDv. ⋅ 34787 Zip Code

Discover this **stunning and meticulously maintained** 3-bedroom, 2.5-bath home, presented in **excellent condition**. The interior has been **freshly painted**, featuring **granite countertops** in both the kitchen and bathrooms. The kitchen is equipped with **stainless steel appliances**, a **spacious island**, a large breakfast bar, and an inviting eat-in area. Enjoy **new flooring throughout the downstairs** in this lovely home. The **generous primary bedroom** is located upstairs and includes an ensuite bath with dual sinks, a roomy shower, and a walk-in closet. The secondary bedrooms are thoughtfully arranged in a **split plan**, ensuring privacy from the primary suite. Convenience continues with a downstairs laundry room featuring hookups. Step outside to a **private, expansive paved lanai**, perfect for entertaining, barbecuing, or relaxing. A large **green space** is just off the front porch. Located just 10 minutes from Disney property, this home is close to all parks, restaurants, shopping, and entertainment. Hamlin Town Center is only a few miles away, and **Orange County National**, the largest golf course in Florida, is nearby. The community offers **resort-style amenities** just steps away, including a pool, two parks, a dog park, pickleball courts, green spaces, and tennis facilities. Enjoy low-maintenance living with the HOA covering exterior upkeep, including roof care, yard maintenance, exterior painting, and lawn care. This home is situated in a **top-rated school district** and boasts a **superb location** with ample parking. Townhomes in this **highly sought-after community** rarely become available. This property is **move-in ready** for its new owners! All info should be verified.

8019 Jeremy Joseph Alley, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to this beautifully landscaped 3-bedroom, 2-bathroom home in the 24-hour guard-gated Stoneybrook West community. Featuring a split-bedroom floor plan, the layout includes a versatile flex room ideal for a home office or den. The kitchen is equipped with white appliances and granite countertops and flows easily into the main living spaces, with ceiling fans installed throughout the home for comfort. A standout feature of this property is the seamless outdoor integration: the living room, family room, and primary suite all open directly onto a spacious, screened-in porch. The primary suite serves as a quiet retreat, complete with an attached bath featuring a garden tub and a separate walk-in shower. Residents of Stoneybrook West enjoy robust community amenities, including a clubhouse, swimming pool, golf course, tennis courts, and a private community boat dock with direct access to Black Lake.

1343 Castleport Road, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code

Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Palmetto floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open-concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, quartz countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.

642 Medora Way, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Stoneybrook West 47/78 SubDv. ⋅ 34787 Zip Code

Move-in ready home located in the highly desirable guard-gated community of Stoneybrook West. This well-maintained property offers a bright and open layout with a functional split-bedroom floor plan designed for comfortable everyday living. The spacious primary suite features a walk-in closet, dual vanities, soaking tub, separate shower, A flexible bonus area just off the suite can easily serve as a home office, nursery, or additional bedroom. The kitchen provides ample storage and flows seamlessly into the main living space, making it ideal for both daily use and entertaining. The family room is highlighted by a cozy fireplace, adding warmth and charm. Enjoy the fully screened backyard with plenty of room to relax or entertain outdoors. Stoneybrook West residents have access to resort-style amenities, including lake access, multiple sports courts, a community pool, playground, fitness center, and an active Town Centre. Conveniently located near shopping, dining, and major highways, this home offers both lifestyle and location.

2281 Oakington Street, Winter Garden

5 Beds ⋅ 3 Baths ⋅ Stoneybrook West Un 06 SubDv. ⋅ 34787 Zip Code

WOW!!! OVER $60,000 RECENT PRICE REDUCTION!! BRAND NEW AC SYSTEM INSTALLED LAST WEEK (7/2/26) Experience refined Florida living in this beautifully enhanced home located within a highly desirable golf course community. The property offers both style and peace of mind with a roof replaced just five years ago and a recently sealed and painted exterior. Inside, the home is designed for both comfort and entertainment, featuring an immersive surround sound system throughout the main level and an impressive dedicated theater/bonus space. Every detail has been curated to elevate everyday living. Step outside to your own private retreat—an exceptional backyard showcasing a custom pool and spa with a striking grotto feature, creating the perfect setting for relaxing or entertaining guests year-round. Residents enjoy access to an array of resort-style amenities, including a clubhouse with dining, fitness center, tennis and basketball courts, beach volleyball, playgrounds, and an expansive community pool. Ideally situated just minutes from world-renowned attractions like Walt Disney World, with convenient access to major expressways and premier shopping and dining destinations nearby, this home offers the perfect balance of luxury, location, and lifestyle. One or more photo(s) have been virtually staged. PLEASE REMOVE SHOES BEFORE ENTERING THE HOME!

13412 Fox Glove Street, Winter Garden

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

It can be negotiated along with the furniture. Welcome to this beautifully maintained 3-bedroom, 3-bathroom townhouse located in the highly desirable Waterleigh community. This modern home offers a functional and inviting open-concept layout, perfect for both everyday living and entertaining. The property features spacious bedrooms, well-appointed bathrooms, and a thoughtfully designed living area filled with natural light. The kitchen stands out with contemporary finishes, ample cabinetry, and a seamless flow into the dining and living spaces. Furniture can be negotiated, providing a convenient move-in-ready opportunity. Residents of Waterleigh enjoy a resort-style lifestyle, including multiple clubhouses, sparkling pools, fully equipped fitness centers, scenic walking trails, playgrounds, sports courts, and beautifully maintained green spaces. The community is known for its welcoming atmosphere and well-planned design. Ideally located, this home offers easy access to everyday essentials and top destinations, including Horizon West, Hamlin Town Center, and the popular Walt Disney World Resort. Enjoy a wide variety of nearby shopping, dining, and entertainment options, along with convenient access to major highways. This is an excellent opportunity to enjoy comfort, convenience, and one of the most sought-after communities in the area.

10089 Salt Point Drive, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Oakland Park B-2 SubDv. ⋅ 34787 Zip Code

Step into a custom residence where calmness, grace, and thoughtful design greet you from the moment you arrive. In the quiet part of community, overlooking peaceful pond views, this luxury home features an open, airy floor plan filled with natural light, upscale laminate planks throughout, large lot. The gourmet kitchen is a true centerpiece here, offering a commercial-grade hood ideal for entertaining, gas stove, Bosch appliances, pot filler, walk-in pantry, and an appliance garage. The living area flows seamlessly to the outdoors through fully retractable sliding glass doors, complemented by surround sound and custom-tinted windows for comfort and privacy. With 4 bedrooms and 3 full baths—including one with direct patio access—the layout is designed for both convenience and flexibility. One bedroom is located on the main level, while upstairs you’ll find a Jack-and-Jill setup and a spacious primary suite featuring a tray ceiling, spotlight accents, and a spa-inspired bath with walk-in shower, separate soaking tub, and a stunning built-in closet with natural light. An exceptional bonus is the private in-law suite above the garage, complete with its own kitchen, living area, bedroom, and stackable washer/dryer—perfect for guests or multi-generational living. The outdoor oasis is a destination of its own, surrounded by bamboo, olive, lime, and persimmon trees. The covered patio invites year-round enjoyment, and the fully fenced property offers privacy and space to unwind. From your backyard, you can even watch Space Shuttle launches light up the sky. Located in the highly desirable golf cart district, this home places you just a 2-minute walk from the West Orange Trail and only 3 miles from historic Downtown Winter Garden. Unbeatable location, unmatched lifestyle. Schedule your private showing today.

906 Allendale Lane, Winter Garden

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