Winter Garden/Oakland Homes with Golf Course Amenities

Winter Garden/Oakland Homes with Golf Course Amenities

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This charming area is not just a place to live; it’s a vibrant community steeped in history and natural beauty. With its picturesque landscapes, quaint downtown, and thriving local culture, Winter Garden and Oakland offer a lifestyle that is both relaxed and invigorating.

One of the region's standout features is its stunning golf course amenities. Imagine waking up to the serene views of lush fairways and pristine greens right outside your window. Homes in this area often boast direct access to some of Florida’s finest golf courses, making it a haven for golf enthusiasts and nature lovers alike. Whether you're an avid golfer or simply appreciate the tranquility that comes with living near a course, these properties provide the perfect backdrop for a fulfilling lifestyle.

Beyond golf, Winter Garden and Oakland offer a plethora of outdoor activities, from scenic parks and lakes to walking trails and community events. The historic downtown Winter Garden is a delightful blend of boutique shops, gourmet dining, and vibrant farmers markets, creating a sense of community that is hard to match.

With the perfect balance of leisure and activity, Winter Garden and Oakland are not just places to call home; they are destinations that inspire a lifestyle of enjoyment and connection. Explore the homes with golf course amenities in this beautiful region, and discover the perfect place to create lasting memories. Your dream home awaits in this idyllic corner of Florida!

Newest Winter Garden/Oakland Homes with Golf Course Amenities

$525,000
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
$465,000
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
$829,900
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
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