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 strong sense of community, making it an ideal place to call home.

Winter Garden boasts a charming downtown district filled with quaint shops, delightful cafes, and lively farmers' markets, all against the backdrop of beautifully preserved historic buildings. Just a stone's throw away, the serene town of Oakland offers a peaceful retreat with its scenic parks and lush greenery, perfect for nature enthusiasts and those seeking a tranquil lifestyle.

One of the standout features of homes in this region is their access to community amenities through association recreation. Many neighborhoods in Winter Garden and Oakland are part of well-maintained communities that prioritize resident enjoyment and social interaction. These communities often feature sparkling swimming pools, well-equipped fitness centers, playgrounds, and picturesque walking trails, ensuring there's something for everyone to enjoy.

Imagine spending your weekends lounging by the pool, hosting barbecues in the community park, or joining in on neighborhood events that foster connections with your neighbors. The association recreation not only enhances your living experience but also cultivates a friendly and welcoming atmosphere.

Whether you are looking for a cozy single-family home, a modern townhouse, or a spacious estate, Winter Garden and Oakland offer diverse real estate options to suit every lifestyle. Discover the magic of this remarkable area, where community spirit meets suburban charm, and make your dream home a reality.

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

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

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

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

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

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

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

5 Beds ⋅ 4 Baths ⋅ Lakeview Pointe At Horizon West SubDv. ⋅ 34787 Zip Code

WELCOME TO LAKEVIEW POINTE AT HORIZON WEST! This 5-bedroom, 4-full-bath Pulte Creekview floorplan offers a flexible two-story layout with a downstairs primary suite, upstairs loft, flex room, 3-car garage, and a fully fenced corner-lot backyard. Hardwood flooring extends throughout the first floor, complemented by tray ceilings in the foyer and primary suite, plantation shutters, neutral interior paint, and updated lighting in the flex space and breakfast nook. The open kitchen, café, and family room create a central gathering space, featuring 42-inch maple cabinetry with crown molding and hardware, granite countertops, an oversized island with breakfast bar seating, built-in wall oven and microwave, corner walk-in pantry, and extended cabinetry along the breakfast nook for additional storage. Glass sliders with a remote-controlled window treatment open to the covered, extended screened brick-paver patio overlooking the private fenced yard. The downstairs primary suite includes a tray ceiling, oversized walk-in closet, dual-sink granite vanity, glass-enclosed tiled walk-in shower, and private water closet. Three additional bedrooms are located downstairs, including one adjacent to a full bath with dual-sink granite vanity, while two bedrooms share another full bath. Upstairs, a loft, storage room, fifth bedroom with extensive closet space, and a fourth full bath provide versatile space for guests, work, hobbies, or media use. Recent improvements include interior and exterior paint, two new AC systems installed in 2025, ceiling fans, bathroom mirrors, front door hardware, epoxy-finished garage floor, and overhead garage storage racks. Kitchen appliances, washer, and dryer convey. A transferable Choice Home Warranty is included through May 2027, subject to warranty terms. Lakeview Pointe HOA includes lawn care, irrigation, community pool, fitness center, playground, and additional community amenities. Convenient Horizon West location near Hamlin shopping and dining, SR-429, Winter Garden Village, Walt Disney World Resort, and major Central Florida attractions.

7052 Enchanted Lake Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained Laurel floor plan, featuring fresh professional exterior paint (2026), 3 bedrooms, 2 bathrooms, and an open-concept layout thoughtfully designed for comfortable everyday living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring stainless steel appliances, a breakfast bar, a walk-in pantry, and an adjoining dining area that flows seamlessly into the living room. Elegant ceramic tile extends throughout the main living areas, while the abundant natural light create a bright, inviting atmosphere. The private primary suite offers a generous walk-in closet and an ensuite bath with dual vanities and a large walk-in shower. Two additional bedrooms are thoughtfully positioned toward the front of the home, providing flexibility for guests, a home office, or hobbies. Enjoy Florida living year-round on the private brick-paver patio, with additional upgrades including an epoxy-coated garage floor, overhead storage racks, seamless gutters, upgraded front elevation with brick accents, and a rear-entry garage for enhanced curb appeal. Located in the Waterleigh master-planned community, residents enjoy resort-style amenities including multiple pools, fitness centers, walking trails, parks, playgrounds, sports courts, community gardens, and scenic lakes. Conveniently located near Horizon West, Hamlin Town Center, New Publix, shopping, dining, major roadways, Walt Disney World, and everything Winter Garden has to offer. Don't miss the opportunity to own this move-in-ready home in one of Central Florida's most desirable communities.

16802 Oakboro Street, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Southern Pines SubDv. ⋅ 34787 Zip Code

**Click the Virtual Tour Link for 3-D walk-through tour** Welcome home to this well maintained FIRST FLOOR 3-bedroom, 2-bath condominium in Winter Garden, ideally located near shopping, dining, and with easy access to major roadways for trips to the airport and theme parks. This corner unit condo offers convenience to parking and features an open floor plan with spacious living room plus a den - perfect for a home office or flex space. The kitchen includes a breakfast bar, pantry, and convenient laundry room just through the kitchen. The split floor plan provides privacy to the primary suite with walk-in closet, linen closet, and en-suite bathroom. Additional bedrooms also feature walk-in closets and the hallway bathroom has an extended vanity for extra space and storage. Residents of Southern Pines Condos enjoy an exceptional array of amenities such as a pool and spa, outdoor kitchen, clubhouse with theater, office space and billiards, indoor basketball and racquetball courts, fitness center, playroom, covered outdoor playground, tennis and beach volleyball courts, and a car wash station. The gated community's HOA fee includes cable, internet, water, sewer, trash, and exterior maintenance, making for a truly low-maintenance lifestyle. Call for a showing today!

200 Southern Pecan Circle Unit 104, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Waterleigh Phase 3bcd SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained home in the master-planned community of Waterleigh community of Horizon West in Winter Garden. This popular Bellake floor plan offers over 2,200 square feet of beautifully maintained living space. Rare concrete block construction on both the first and second floors, thoughtful updates by the current owner, and a functional open-concept layout make this home stand out from the moment you arrive. As you step inside, you're welcomed by a versatile flex room to the left, perfect for a home office, playroom, or formal sitting area, while the updated half bath with a new vanity and light fixture is conveniently located to the right. Continue into the spacious great room that flows seamlessly into the kitchen, creating an inviting space for everyday living and entertaining. The kitchen features stainless steel Whirlpool appliances, granite countertops, a large center island with additional cabinet storage, ample cabinetry, a dedicated dining area, and overlooks the main living space. Select areas of fresh interior paint, refreshed tile flooring, updated lighting, and a new ceiling fan add to the home's clean, well-cared-for feel. Just beyond the kitchen, a mudroom provides access to the attached two-car garage. Additional storage can be found beneath the staircase. Upstairs you'll find all three bedrooms, two full bathrooms, the laundry room, and an additional storage closet. The spacious primary suite features a beautifully remodeled en-suite bathroom with a walk-in shower finished in timeless subway tile, contrasting dark grout, sleek matte black fixtures, and a custom-designed walk-in closet. The secondary bedrooms share a full bathroom with a dual-sink vanity. Sliding glass doors off the great room open to the covered, screened lanai with paver flooring overlooking the side and backyard. The security system, security cameras, washer, and dryer all convey. Enjoy Waterleigh's resort-style amenities including four pools, four parks, two fitness centers, tennis courts, beach volleyball, putt-putt golf, walking trails, a fishing pier, and a beautiful clubhouse, while the HOA maintains the lawn and shrubs. Minutes from Hamlin Town Center, Publix, SR 429, Disney, and the shores of Hickory Nut Lake, you'll even enjoy Disney fireworks from your driveway. Schedule your private showing today!

15741 Fountain Springs Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve SubDv. ⋅ 34787 Zip Code

Luxury Toll Brothers End-Unit Townhome in Lakeshore Preserve! This beautifully maintained CICERO Spanish Colonial floorplan offers an open-concept layout with 10' ceilings, 8' doors, wood-look tile flooring, and abundant natural light. The gourmet kitchen features a center island, 42" cabinets, Diamond white-quartz countertops, stainless steel appliances, natural gas cooking, a large pantry, and a new oversized single-basin sink. The first-floor owner's suite includes a spacious walk-in shower and dual vanities. Upstairs you'll find two generous bedrooms, a loft, and a charming wraparound balcony. A covered walkway connects the home to the attached two-car garage. Recent upgrades include new landscaping, French doors added to the kitchen, water-resistant laminate flooring throughout the upstairs, updated quartz countertops in the kitchen and guest bath, upgraded lighting and staircase chandelier, new refrigerator, washer and dryer, saltwater softener system, patio pavers, and added garage storage. The home has been meticulously maintained with annual HVAC servicing and regular tankless water heater maintenance. Enjoy resort-style living at Lakeshore Preserve with a lakefront clubhouse, fitness center, gathering room, catering kitchen, resort pool, kayaking, and paddleboarding. Ideally located in Horizon West, just minutes from Disney, Universal, shopping, dining, and major retail centers.

8873 Fountain Palm Alley, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 4 SubDv. ⋅ 34787 Zip Code

Captivating water and golf course views set the stage for a chic and distinguished single-story residence in Lakeshore Preserve. This better-than-new home boasts a great room floorplan with split bedroom layout, sliding pocket doors, an exceptional screened pool patio area with hybrid saltwater and chlorine pool with sun shelf and water features, plus tranquil lake beyond. Elegant white on white kitchen with stainless appliances, gas cooktop with hood, waterfall quartz island, and an abundance of cabinetry including a few lighted glass showplace cubicles with doors. Graced with wood-look tile flooring and transitional neutral grays and whites throughout this home offers a clean-look elegant canvas. Landscape lighting creates an elegant ambiance at night. Enjoy a nearly carefree lifestyle with exterior yard maintenance included in your monthly HOA fee. 1-gig high-speed internet is also included. Community features resort-style amenities including a waterfront community pool, cabanas, walking trails, and access to Lake Panther via a community ramp for canoes, kayaks, and other non-motorized watercraft. There’s also a community clubhouse with fitness center and activity spaces. Top-rated Panther Lake Elementary is located within the neighborhood and Horizon High School is across the street. Orange County National Golf Center is just minutes away. Enjoy nightly fireworks from the Magic Kingdom at Walt Disney World and easy access to the SR-429 to connect to downtown Orlando. Welcome to Horizon West’s best address for lifestyle, luxury, and livability.

15619 Giant Foxtail Court, Winter Garden

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