Winter Garden/Oakland Homes with Golf Community Community Extras

Winter Garden/Oakland Homes with Golf Community Community Extras

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. Known for its charming small-town vibe and vibrant community spirit, this area offers a delightful blend of natural beauty and modern amenities. With its picturesque landscapes, lush parks, and scenic lakes, Winter Garden is an outdoor enthusiast's paradise, perfect for those who enjoy hiking, biking, or simply soaking in the sun.

One of the standout features of this region is its exceptional golf communities, which provide residents with an unparalleled lifestyle. Imagine waking up to stunning views of manicured fairways and lush greens right outside your window. Homes in these golf communities are designed with elegance and comfort in mind, offering spacious layouts, modern finishes, and often, private pools and outdoor living spaces perfect for entertaining.

In addition to the luxurious homes, residents of Winter Garden and Oakland enjoy a wealth of community extras. Many golf communities feature clubhouses, fitness centers, and social events, fostering a strong sense of camaraderie among neighbors. You’ll find everything from gourmet dining options to boutique shopping, all within a short drive or leisurely stroll.

With its rich history, top-rated schools, and easy access to major highways and attractions like Disney World, Winter Garden and Oakland are not just places to live—they are vibrant communities where families can thrive and create lasting memories. Whether you are a golf enthusiast or simply seeking a tranquil lifestyle, this region has something for everyone. Come and discover your dream home in Winter Garden and Oakland today!

Newest Winter Garden/Oakland Homes with Golf Community Community Extras

$689,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code
Welcome to Stoneybrook West—a one-of-a-kind community in Winter Garden! This premier neighborhood offers 24-hour guarded entry, a massive town center, and resort-style amenities including an Olympic-sized pool with a splash zone, state-of-the-art fitness center, playground, tennis, basketball, and pickleball courts. Enjoy lakeside living with a fishing/viewing pier and private boat ramp, plus a full calendar of community events. Best of all, your HOA fees cover both internet and cable! Set on a tranquil pond with no rear neighbors, this home boasts irresistible curb appeal from the moment you arrive. Inside, the thoughtfully designed floor plan balances elegance and ease. The front of the home features formal living and dining areas—perfect for hosting—while the rear opens to a bright, open-concept kitchen and family room ideal for everyday living. The kitchen is a chef's delight with ample counter space, a walk-in pantry, stainless steel appliances, stylish tile backsplash, and a breakfast bar. Step through the sliding doors to a screened patio and fully fenced backyard—a private oasis for pets, play, or peaceful pond gazing. Need space for guests or extended family? A main-floor bedroom with a full bath offers flexibility and privacy. Upstairs, a generous loft awaits—use it as a media room, playroom, or second living area. Both the loft and the primary suite open to a screened balcony with serene views. The primary retreat itself is a showstopper, featuring a garden tub, separate walk-in shower, dual vanities with a makeup station, and an enormous walk-in closet. Convenience continues with an upstairs laundry room equipped with cabinets and a utility sink. Fresh new flooring has been installed throughout the entire upper level, and the home has been treated to a brand-new coat of paint, giving it a clean, modern feel throughout. Recent upgrades also include a new roof (2023), new water heater (2023), and AC (2019). You'll also appreciate surround sound pre-wiring in the family room and loft, ceiling fans throughout, and abundant storage. Located just steps from the resident gate, Balforn Tower Way places you minutes from the community town center, golf clubhouse, top-rated schools, dining, shopping, medical facilities, and entertainment. This is more than a home—it's a lifestyle.

2549 Balforn Tower Way, Winter Garden
$635,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated community of Stoneybrook West. Offering over 2,800 square feet of living space, this home combines a spacious and flexible floor plan with a fantastic setting overlooking the 6th hole and no rear neighbors. Recent improvements include a newer roof and A/C, fresh exterior paint, renovated kitchen, bathrooms, and flooring. The main level offers multiple living and dining spaces, while the kitchen features stone countertops, stainless steel appliances and abundant cabinetry. Upstairs, the spacious primary suite includes a tray ceiling, walk-in closet and private bath with dual vanities and a beautifully remodeled walk-in shower. The oversized loft provides plenty of flexibility for a second living area, media room, playroom or home office. Step outside to a large backyard with expansive golf course views and plenty of room to enjoy the outdoor living. Stoneybrook West offers an impressive collection of amenities, including a community pool, golf, clubhouse, tennis and basketball courts, playgrounds and walking paths. Ideally located near Winter Garden Village, historic Downtown Winter Garden, shopping, dining and major roadways, this home offers a great combination of space, improvements, amenities and community.

15081 Masthead Landing Circle, Winter Garden
$1,137,150
4 Beds ⋅ 4 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code
Under Construction. 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, striking Calacatta 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
$710,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
*Some photos are virtually staged. Video tour available.* This home has a full-home SOLAR PACKAGE that is included in the sales price and generates enough energy to produce a $0 ELECTRIC BILL! The only power utility payment is a $55 monthly connectivity to Duke. That’s it! You’ll be welcomed by the inviting FRONT PORCH, fresh landscaping and EXTENDED PAVER DRIVEWAY. The spacious entry is surrounded by wood floors and upgrading lighting in the formal living and dining rooms. The tall ceiling in the family room makes the already large space feel even more grand as it opens to the kitchen and breakfast nook. This kitchen has a walk-in pantry, ample counter space, a NEW MICROWAVE and 2 NEW REFRIGERATORS, one of which is in the EXTRA-LARGE LAUNDRY ROOM. There is a full guest/pool bath downstairs with direct access to the SCREENED PATIO that runs the length of the house. Outside you’ll find a large backyard with a PRIVATE VINYL FENCE, raised GARDEN BEDS and a FIRE PIT. Two sets of sliding doors lead back to both the family room and the primary suite. The downstairs primary suite has nice natural lighting, a WALK-IN CLOSET with built-in storage, a garden tub, separate shower, and water and linen closets. Upstairs you’ll find a BARRE DANCE STUDIO, a full wall of mirrors and a fan to keep your dancers cool. This is also a versatile space if you don’t have a dancer in the family. There is also an open loft, 3 secondary bedrooms and a hall bath. Additional upgrades include TWO NEW AC SYSTEMS (2026), NEWER ROOF (2022), epoxy flooring in the garage, all appliances convey, and ceiling fans throughout! The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks.

13527 Fox Glove Street, Winter Garden
$400,000
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
$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
$465,000
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
$1,765,000
5 Beds ⋅ 4 Baths ⋅ Oakland Park B-2 SubDv. ⋅ 34787 Zip Code
Welcome home to calm, light-filled luxury on a peaceful pond in the sought-after golf cart district—just steps from the West Orange Trail and 3 miles to historic Downtown Winter Garden. This 4-bed, 3-bath custom home sits on a large lot and features an open, airy floor plan with upscale laminate flooring throughout. The gourmet kitchen is built to entertain: commercial-grade hood, gas range, Bosch appliances, pot filler, walk-in pantry, and appliance garage. Fully retractable sliding glass doors open the living area to the outdoors, with surround sound and custom-tinted windows adding comfort and privacy. One bedroom is on the main level; upstairs offers a Jack-and-Jill suite plus a private primary retreat with tray ceiling, spotlight accents, walk-in shower, soaking tub, and a stunning light-filled built-in closet. A rare bonus: a private in-law suite above the garage with its own kitchen, living area, bedroom, and stackable laundry—ideal for guests or multi-generational living. Outside, escape to your own oasis surrounded by bamboo, olive, lime, and persimmon trees, with a covered patio, full fencing, and even rocket launch views from your backyard. Unbeatable location. Unmatched lifestyle. Schedule your private showing today.

906 Allendale Lane, Winter Garden
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