Winter Garden/Oakland Homes with Association Recreation - Owned Community Features

Winter Garden/Oakland Homes with Association Recreation - Owned Community Features

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant area is renowned for its picturesque landscapes, rich history, and a close-knit community atmosphere that makes it a perfect place to call home. With its charming downtown filled with boutique shops, delightful eateries, and a bustling farmer's market, Winter Garden offers a unique blend of small-town charm and modern conveniences.

One of the standout features of this region is the abundance of homes within association recreation-owned communities. These neighborhoods are designed with lifestyle in mind, providing residents with access to exceptional amenities that enhance day-to-day living. Imagine waking up to the serene views of beautifully landscaped parks, or taking a leisurely stroll along scenic walking trails. Many of these communities boast resort-style pools, fitness centers, and clubhouse facilities that serve as social hubs for residents, fostering a sense of belonging and community spirit.

The allure of Winter Garden and Oakland extends beyond just the homes; it’s about the lifestyle. Families can enjoy a wealth of outdoor activities, from kayaking on the nearby lakes to biking along the West Orange Trail. Additionally, the proximity to major attractions like Disney World and Universal Studios makes this area an ideal location for those seeking both tranquility and adventure.

Whether you're looking for a cozy family home or a vibrant community to retire in, Winter Garden and Oakland offer an array of options to suit every lifestyle. Discover the magic of this region and find your dream home today!

Newest Winter Garden/Oakland Homes with Association Recreation - Owned Community Features

$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
$1,395,000
4 Beds ⋅ 3 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. Newly remodeled in 2026 and presented in like-new condition, this exceptional single-story lakefront home blends an elevated luxe coastal feel with relaxed Florida waterfront living. Set on a rare oversized lot along skiable Huckleberry Lake, the property offers exceptional privacy and space, with approximately 40 feet of separation between neighboring homes. The light and inviting interior features (4) four bedrooms, (3) three full baths, and a spacious open-concept floor plan. The beautifully updated kitchen showcases quartz countertops and flows seamlessly into the main living and entertaining areas. A generously sized open flex room offers additional versatility as a formal dining room, home office, formal living room, or sitting room and can easily be enclosed for additional privacy. Step outside to a large fenced backyard with a private pool and spa, all overlooking Huckleberry Lake. Enjoy direct lake frontage and water access, with the opportunity for a private dock, subject to applicable HOA approval and permitting. The (3) three-car garage includes a Tesla EV charger, and the expansive driveway accommodates up to (6) six additional vehicles. Lakeview Pointe offers a community dock on Huckleberry Lake, resort-style pool with splash area, and fully equipped fitness center. The HOA also takes care of the home's exterior lawn maintenance, giving you more time to enjoy the lake, pool, and Florida lifestyle. Ideally located in Winter Garden's Horizon West area, with easy access to SR 429 and minutes from shopping, dining, entertainment, and everyday conveniences. The property is currently zoned for A-rated Summerlake Elementary, Hamlin Middle School, and Horizon High School. Nearby early-learning options include Primrose School of Horizon West, The Learning Experience - Horizon West, and KLA Schools of Horizon West. Walt Disney World is approximately 20 minutes away. Buyers should independently verify current school assignments and grades. A rare opportunity to own a beautifully remodeled single-story pool home on skiable Huckleberry Lake, combining privacy, flexible living spaces, an oversized lakefront lot, and true Florida waterfront living.

14048 Larkspur Lake Drive, Winter Garden
$1,170,000
5 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Welcome home to this like-new luxury home in Lakeshore Preserve, the highly desirable community in Horizon West (West Orange County). Great location just off the 429 Western Beltway providing easy access to Orlando and Tampa, and less than 8 miles to Disney parks. You can even view the Disney fireworks nightly from this neighborhood. Wonderfully situated on one of the largest Executive Home sites with views of the green space in the back and a pond across the street, the Toll Brothers Gardenia Model is sure to please the pickiest buyers. This floor plan of just under 4200 sf offers 10' ceilings, 2 primary suites, 3 additional bedrooms, an enormous bonus room, 4 1/2 bathrooms, an extended screened patio downstairs and screened balcony upstairs to enjoy the views and outdoors. Attractive tile roof, tankless water heater, low-e windows and natural gas provide the maximum energy efficiency. Beautiful upgrades are found throughout the home starting with the luxury vinyl plank flooring in all the downstairs living areas. The well-appointed kitchen features an extended island with eating area, upgraded appliances and fixtures, convection oven, deep farmhouse sink and plenty of cabinetry. Off the kitchen is the butler's pantry and walk-in pantry leading to a formal dining room. Entertaining is a breeze with the open floor plan combining the kitchen with the family room with 3 huge sliding doors opening to the oversized brick-paver screened patio. The downstairs primary suite is spacious and works well for multi-generational households. The upstairs primary suite is even larger and its luxury, spa-like bathroom is like no other with a custom stand-alone 7' tub, oversized frameless shower with multiple shower heads, and 2 walk-in closets with custom organizers. A 22' x 18' loft separates the primary bedroom from the remaining 3 bedrooms and 2 additional full bathrooms. Come enjoy the Lakeshore lifestyle and amenities including clubhouse where numerous social activities are held to network with fabulous neighbors, a resort-style pool, fitness center, volleyball court, playgrounds, dog park, and canoes to enjoy Panther Lake which wraps around the clubhouse. The HOA fee includes grounds maintenance, 1 gig internet, cable, sidewalk pressure washing, and all amenities. Make your appointment to view this one in person. It's even more beautiful than the photos.

8222 Topsail Place, Winter Garden
$845,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2c-1 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully RENOVATED home, The SEA CLIFF model -One of the largest floorplans in the Waterleigh community.where modern elegance meets comfortable living. The home has been extensively updated with a sophisticated neutral palette, designer lighting, luxury vinyl plank flooring, custom-style cabinetry, quartz countertops, and upgraded fixtures throughout. . This beautiful 2 story home features 4 bedrooms & 3.5 full baths,as you enter the foyer, you are greeted with a formal dining room. Customize this area to meet your needs with an optional den. The show-stopping kitchen is the heart of the home, featuring a large waterfall-edge island, abundant cabinetry, statement backsplash, upgraded appliances, and beautiful accent lighting. The open-concept design seamlessly connects the kitchen, dining, and living spaces, creating an ideal setting for both everyday living and entertaining. bathrooms have been stylishly renovated with contemporary vanities, quartz countertops, modern black fixtures, designer mirrors, and beautiful tile finishes. Additional highlights include custom wall paneling, upgraded trim, elegant lighting, and carefully curated finishes throughout. within walking distance of the community clubhouse and amenities This amazing home is in the highly desirable community “Waterleigh.” Located just off the 429 west of Disney, This community amenities include a huge resort style pool, fitness gym, club house, dog park, huge sports fields, playground, beach volleyball, Tennis, lake view BBQ/picnic area, with sidewalks that wind around the scenic lakes, nature, and community for a relaxing and enjoyable lifestyle with periodic fitness stops if you choose. Fast and easy access anywhere. Hospitals, restaurants and shopping are all nearby. Great schools; Water Spring Elementary, Water Spring Middle, and Horizon Highschool

10169 Shallow Water Drive, Winter Garden
$549,500
3 Beds ⋅ 3 Baths ⋅ Waterleigh Phase 3a SubDv. ⋅ 34787 Zip Code
Welcome HOME to this beautifully upgraded Bellake floorplan located in the HIGHLY sought-after Waterleigh community in the heart of Horizon West! From the moment you walk through the front door, you'll be welcomed by a bright, open-concept layout designed for both everyday living and effortless entertaining. Just off the entry, the ENCLOSED FLEX ROOM offers the perfect space for a home office, playroom or media room. The heart of the home is the kitchen, where you'll find stainless steel appliances, a stylish subway tile backsplash, an updated faucet, upgraded lighting, and elegant crown molding throughout. Overlooking the spacious dining and living areas, this inviting space makes it easy to stay connected whether you're hosting family gatherings or enjoying a quiet evening at home. Upstairs, escape to your spacious primary suite, thoughtfully designed to feel like your own private retreat. Custom touches including a MODERN ACCENT WALL, CROWN MOLDING, and a custom walk-in closet with built-in shelving. Two additional bedrooms provide flexibility for family, guests, or hobbies, while the upgraded laundry room features added cabinets and shelving for exceptional organization. Step outside to your EXTENDED COVERED LANAI with an ALUMINUM ROOF, creating the perfect outdoor living space for morning coffee, weekend barbecues, or relaxing Florida evenings. The home has been beautifully updated with FRESH EXTERIOR PAINT completed in MAY 2026 and a professionally repainted interior, offering a modern, MOVE-IN-READY feel from the moment you arrive! Additional upgrades include GUTTERS, upgraded ceiling fixtures, NO CARPET DOWNSTAIRS or on the lower portion of the staircase, and a garage featuring EPOXY FLOORS and overhead storage racks. Living in Waterleigh means enjoying more than just a beautiful home, it's a lifestyle. This community offers the convenience of NO CDD and HOA-maintained landscaping! Residents enjoy access to FOUR resort-style amenity centers featuring pools, fitness centers, clubhouses, playgrounds, sports courts, scenic walking trails, community events, and a GOLF CART FRIENDLY atmosphere. You'll even enjoy views of Walt Disney World fireworks and NASA rocket launches from within the community. Located just minutes from Walt Disney World, you'll also be close to shopping, dining, major highways, the newly opened Horizon West Regional Park, the new Horizon West Library opening soon, and the highly anticipated Lifetime Fitness coming soon. This home has been thoughtfully upgraded, meticulously maintained, and is ready for its next owners to make lasting memories. Schedule your private showing TODAY and discover why so many families love calling Waterleigh home!

9462 Komika Lane, Winter Garden
$290,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to Southern Pines, one of Winter Garden's most desirable gated condominium communities. This spacious second floor 3 bedroom, 2 bathroom condo offers approximately 1,453 square feet of comfortable living space with an open, functional layout that is perfect for everyday living, working from home, or entertaining family and friends. The unit offers luxury vinyl flooring, the kitchen overlooks the living and dining areas, creating a bright and inviting gathering space, while the split bedroom floor plan provides added privacy for the primary suite. The generous primary bedroom features a walk in closet, and the two additional bedrooms offer excellent space for guests, family, or a home office. Southern Pines is known for its outstanding amenities, including a resort style pool and spa, clubhouse with a gaming area and a movie room, fitness center, indoor basketball and racquetball courts, tennis courts, playground, picnic and barbecue area, and beautifully maintained grounds. The monthly condominium fee also covers valuable services including water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and security, making ownership both convenient and low maintenance. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major shopping and dining, the West Orange Trail, SR 429, the Florida Turnpike, Highway 50, and world famous attractions such as #Disney and #Universal, this home offers an exceptional combination of location, lifestyle, and value. Whether you are looking for your primary residence, a second home, or an investment opportunity, this move in ready condo is one you will not want to miss. Schedule your private showing today and discover everything Southern Pines has to offer.

142 Southern Pecan Circle Unit 204, Winter Garden
$244,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden
$650,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Great house fronting the park, gym, and community pool. Tons of upgrades inside and out. Beautiful screened pool with motorized shade for privacy on patio. Saltwater pool. Luxury Vinyl Plank throughout the house. NO Carpet! Kitchen has lots of upgrades as well. KitchenAid appliances. Wall oven and cooktop. Samsung refrigerator included. Washer and Dryer also stay! 5 mounted TV's will convey as well! Ring alarm system with cameras as well. Plantation shutters throughout.

14048 Lake Abbotts Drive, Winter Garden
$565,000
3 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Luxurious upgraded TOLL BROTHERS Townhome located in coveted Lakeshore Preserve! As you enter this Immaculate 3-bedroom, 2.5-bathroom townhouse the living area offers a bright spacious open floor plan with 10' ceilings and upgraded kitchen area perfect for entertaining or simply bringing out your inner chef! The large center island provides plenty of space for multiple people to enjoy and an additional generous sized counter invites guests to join all activities centered in the kitchen. Featuring 42" upgraded cabinets, stainless steel appliances and a natural gas range, the area has sliding glass doors that open up to the private patio so that enjoying the outdoors becomes effortless. Outside, a covered walkway leads to the 2-car garage located across the beautifully paved patio. Moving upstairs, the primary bedroom is a tranquil retreat with a generous sized walk-in closet and an ensuite bathroom with dual sinks and at private water closet. From the relaxing bedroom you can enjoy beautiful sunsets in the evening without leaving the comfort of your home. Located on the other side of the second floor are two comfortable bedrooms that share a spacious bathroom across the hall. In addition, the home offers a whole house water filtration system, tankless water heater and above head storage racks in the garage. If you are ready to enjoy resort style living, Lakeshore Preserve also offers plenty of activities with a beautiful clubhouse with fitness center, outdoor community pool and playgrounds nestled along the shores of Panther Lake. Whether you enjoy going for a stroll along one of the walkways or grabbing a seat in one of the beautifully landscaped park areas, you are sure to find a quiet place with views. Best of all, your HOA dues cover not only all the amenities, but also exterior maintenance of your townhome, exterior painting, roof cleaning, and basic cable and internet. This well-maintained townhome in Horizon West is close to top rated schools, Disney attractions, shopping, dining, and has easy access to HWY 429.

8932 Bismarck Palm Drive, Winter Garden
$499,900
3 Beds ⋅ 3 Baths ⋅ Longleaf At Oakland SubDv. ⋅ 34787 Zip Code
Welcome to Longleaf at Oakland by Pulte! Built in 2020, this move-in-ready three-bedroom, 2.5-bath home offers 1,811 square feet of stylish living space featuring brand-new luxury vinyl plank flooring throughout, fresh interior paint, quartz countertops, stainless steel appliances and an open-concept layout designed for comfortable everyday living and effortless entertaining. Located less than five minutes from the new Oakland Town Center, you’ll be close to an exciting new lifestyle destination featuring chef-driven restaurants, boutique shopping, fitness and wellness concepts, medical services, outdoor gathering spaces and everyday conveniences. Historic Downtown Winter Garden, the West Orange Trail and major highways are also just minutes away. Residents of Longleaf at Oakland enjoy a community pool, playground and beautifully maintained green spaces, all within one of West Orange County’s most desirable communities. Don’t miss the opportunity to own this beautifully updated, move-in-ready home in one of Oakland’s most sought-after neighborhoods. Schedule your private showing today!

2766 Bobcat Chase Boulevard, Winter Garden
$295,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
NEWEST TOWER | TOP FLOOR | FOUNTAIN VIEW This is resort-style living at its absolute finest. This Fountain View Palm Unit in Tower 2 — the newest and most beautifully appointed tower in the community — offers the perfect blend of luxury, lifestyle, and income-generating opportunity. Step into a world-class destination that rivals the finest resorts anywhere in the world. With stunning superior views, the most updated and designer-curated décor in the entire property, and access to an unparalleled collection of amenities, this is more than a home — it's a five-star experience every single day. When you're not enjoying it yourself, let your investment work for you. This property sits within a prestigious hotel-managed rental program, meaning a professional, on-site operator handles everything — from bookings and guest services to housekeeping and maintenance. Completely hands-off ownership with income flowing in while the resort does all the heavy lifting. Owners enjoy access to resort amenities including pools, restaurants, spa, fitness facilities, and more — all maintained to the highest hospitality standards. Whether you're seeking a personal escape, a vacation retreat, or a smart investment vehicle, this unit checks every box. Newest tower. Most updated finishes. Superior views. World-class amenities. Professionally managed income potential. Financials available. Opportunities like this are rare — and they don't stay on the market long.

14501 Grove Resort Avenue Unit 2703, Winter Garden
$190,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort SubDv. ⋅ 34787 Zip Code
TOWER 3 LOCATION CLOSEST TO THE WATERPARK! Exceptional opportunity to own at The Grove Resort & Water Park, one of Central Florida’s premier vacation ownership destinations just minutes from Walt Disney World. This condo is a beautifully furnished Birch Plan residence offering a comfortable, turnkey layout designed for personal enjoyment and income-producing vacation rental use. The open living area, full kitchen, private bedrooms, and resort-style finishes create an inviting retreat for Owners and guests alike. The Grove offers an impressive amenity package including a water park, multiple pools, lazy river, restaurants, bars, spa, fitness center, lake activities, arcade, onsite market, and full-service onsite management. Owners may enjoy generous personal use while the onsite management team handles guest services, reservations, maintenance, and day-to-day rental operations. With its strong location, established resort setting, and continued appeal to Orlando visitors, this Birch Plan condo is a compelling choice for Buyers seeking lifestyle, convenience, and long-term Central Florida vacation ownership.

14501 Grove Resort Avenue Unit 3231, Winter Garden
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