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 vibrant area seamlessly blends the charm of small-town living with the allure of modern conveniences, making it a sought-after destination for families, retirees, and golf enthusiasts alike.

Winter Garden, with its picturesque downtown, boasts a rich history and a thriving arts scene. Stroll along the beautifully restored historic district, where quaint shops, delightful cafes, and local farmers' markets create a warm and inviting atmosphere. Just a stone's throw away, the serene community of Oakland offers a tranquil retreat, surrounded by lush landscapes and stunning lakes, perfect for those who appreciate nature's beauty.

For golf lovers, the homes in Winter Garden and Oakland are a dream come true. Many properties are situated within exclusive golf course communities, offering residents easy access to meticulously manicured greens and breathtaking views. Imagine waking up to the gentle sounds of nature and stepping out onto your patio, with the fairways stretching before you. These homes with golf course amenities provide not just a residence but a lifestyle—one that encourages relaxation, recreation, and social interaction among neighbors who share a passion for the game.

Whether you're looking for a luxurious estate or a cozy family home, Winter Garden and Oakland present a diverse selection of properties that cater to every taste and budget. With its unbeatable combination of scenic beauty, community spirit, and golf course living, this region is truly a hidden gem in Florida. Come discover your perfect home in Winter Garden and Oakland, where every day feels like a vacation!

Newest Winter Garden/Oakland Homes with Golf Course Amenities

$438,000
3 Beds ⋅ 2 Baths ⋅ Stoneybrook West Unit 3 Rep SubDv. ⋅ 34787 Zip Code
Located in the highly desirable Stoneybrook West community of Winter Garden, this 3-bedroom, 2-bath home offers over 1,600 square feet of living space in a 24-hour manned, Guard-Gated Golf community. The home features vaulted ceilings, a built-in closet system in the primary bedroom, and a spacious covered and screened-in back patio overlooking a fully fenced backyard with lush landscaping. Recent updates include an A/C replaced in December 2024, a 2023 water heater, and a NEW roof scheduled to be installed in approximately two weeks. The combination of these major updates provides added peace of mind for the next owner. Stoneybrook West offers an incredible array of amenities, including a resort-style Olympic-sized pool, children's splash area, clubhouse, fitness center, tennis, pickleball, basketball and volleyball courts, playground, fishing pier, private boat ramp and access to Black Lake, along with numerous community activities. The community also features 24-hour guarded security, and the low HOA fee includes cable and internet. Zoned for highly desirable Whispering Oak Elementary, SunRidge Middle School and West Orange High School, this home is conveniently located near Winter Garden Village, Fowler's Grove, Historic Plant Street and downtown Winter Garden, offering an abundance of shopping, dining and entertainment. Easy access to major roadways including State Road 429 makes commuting throughout Central Florida convenient. A great opportunity to own a well-maintained home with valuable updates in one of Winter Garden's most sought-after gated golf communities!

2250 Oakington Street, 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
Start Your Search