Winter Garden Homes with Association Recreation - Owned Community Features

Winter Garden Homes with Association Recreation - Owned Community Features

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County. Known for its picturesque landscapes and vibrant community spirit, Winter Garden offers a perfect blend of small-town charm and modern amenities. With its roots dating back to the 19th century, the city boasts a rich history that is beautifully reflected in its well-preserved downtown area, featuring quaint shops, delightful restaurants, and a lively farmers market that draws residents and visitors alike.

For those seeking a home in this idyllic locale, Winter Garden is home to several residential communities that offer association recreation features, ensuring a lifestyle filled with leisure and enjoyment. Imagine living in a neighborhood where amenities such as sparkling swimming pools, well-maintained parks, and fitness centers are just steps away from your front door. These community features foster a sense of belonging and make it easy to meet neighbors and create lasting friendships.

Winter Garden is also renowned for its outdoor activities, with an extensive network of trails and parks that cater to every outdoor enthusiast. Whether you enjoy hiking, biking, or simply taking a leisurely stroll, you'll find plenty of options to explore the natural beauty that surrounds you.

With its welcoming atmosphere, excellent schools, and proximity to major attractions like Walt Disney World, Winter Garden is not just a place to live—it's a place to thrive. Come discover the charm of Winter Garden and find your dream home in this delightful community!

Newest Winter Garden Homes with Association Recreation - Owned Community Features

4 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully designed 4-bedroom, 3.5-bath home offering stylish upgrades and exceptional indoor-outdoor living in the charming Town of Oakland. From the inviting covered entry and brick-paver driveway to the bright, open interior, every space has been thoughtfully designed for comfortable everyday living and effortless entertaining. The impressive kitchen features abundant cabinetry, expansive countertops, stainless-steel appliances, a natural gas cooktop, built-in oven and microwave, subway-tile backsplash, and an oversized center island with generous seating. Fabulous pantry features custom shelving and refrigerator. The kitchen flows seamlessly into the spacious living area, highlighted by a dramatic floor-to-ceiling accent wall with a sleek electric fireplace and built-in cabinetry. The formal dining room offers soaring ceilings, abundant natural light, and an elegant statement fixture. The spacious first-floor primary suite provides a peaceful retreat with a tray ceiling and a luxurious ensuite bathroom featuring a large glass-enclosed shower, separate soaking tub, dual-sink vanity, huge walk-in closet and distinctive designer finishes. Upstairs, you will find three additional bedrooms and a versatile bonus room—perfect for a home office, media room, playroom, or additional gathering space. One of the upstairs bedrooms includes a private ensuite bathroom, providing an ideal arrangement for guests. Sliding glass doors open to a private, screened outdoor oasis featuring an extended brick-paver patio, covered dining space, multiple conversation areas, and a relaxing 8-person spa—perfect for enjoying Florida living throughout the year. A privacy fence enhances the peaceful backyard setting. Residents of Hull Island enjoy access to a community pool, dog park, playground, and picnic area. The neighborhood also offers convenient access to the Oakland Nature Preserve, 22-mile West Orange Trail, and downtown Oakland. Enjoy the town’s Thursday farmers market, Arts and Heritage Center, local coffee shop, and Speer Park, with vibrant downtown Winter Garden just minutes away. Conveniently located near major highways, theme parks, downtown Orlando, Orlando International Airport, restaurants, shopping, and hospitals, this exceptional Oakland home combines contemporary style, thoughtful design, and an outstanding Central Florida lifestyle. You're only an hours' drive to some of Florida's finest beaches. Schedule your private showing today!

1016 Catori Road, Oakland

4 Beds ⋅ 3 Baths ⋅ Oakland Parkb-3 SubDv. ⋅ 34787 Zip Code

A rare opportunity in highly sought-after Oakland Park—this beautifully furnished, turnkey home offers **4 spacious bedrooms, 3 full bathrooms, including a first-floor bedroom and full bath ideal for guests, extended family, or an in-law arrangement**, plus the exceptional Winter Garden lifestyle buyers are looking for. Tall ceilings, 8-foot doors, elegant architectural details, high-end décor, and thoughtfully designed living spaces create an elevated yet comfortable feel throughout. (If the buyer prefers not to keep the furniture and furnishings, they can be excluded from the sale.) The showpiece kitchen is truly the heart of the home, featuring premium quartz countertops, a 5-burner gas range, stainless steel hood, striking designer backsplash, and spacious walk-in pantry. The spa-inspired primary suite offers an expansive private bathroom and generous walk-in closet, creating the perfect retreat. And for a little extra personality, the home even has its very own “Harry Potter” closet! Enjoy Florida living from the inviting screened front porch, complete with a porch swing perfect for morning coffee, an afternoon book, or relaxing at the end of the day. The back patio and fenced yard provide another comfortable setting for entertaining, outdoor dining, or simply enjoying the beautiful Florida weather. An expansive 3-car garage offers exceptional space and storage. Offered fully furnished with beautiful, high-end furnishings and décor, this home is truly turnkey—just bring your suitcase and start enjoying the lifestyle. Located near highly regarded schools and just moments from the West Orange Trail, walk, bike, take your golf cart, or drive to charming Downtown Winter Garden, the Farmers Market, restaurants, shopping, and entertainment. Move in before the holidays and experience everything this incredible community has to offer, including festive neighborhood traditions and upcoming celebrations such as the golf cart parade, fall festival, and more. An exceptional opportunity to own a remarkably equipped home in one of the area’s most desirable communities at an amazing value.

226 Hammock Preserve Loop, Oakland

4 Beds ⋅ 4 Baths ⋅ Waterside/Johns Lk-Ph 2a SubDv. ⋅ 34787 Zip Code

FORMER BUILDER MODEL HOME - and it shows. When a builder builds their own model, they hold nothing back, and this 4-bedroom, 3.5-bath, 2,958 sq ft home in Waterside on John's Lake is the proof: Upgrades everywhere! Gourmet kitchen with stacked cabinets, 8-foot doors throughout, recessed lighting, wood panel on ceiling, a whole-home speaker system, plus so much more! A finish package that is nearly impossible to replicate today. The open kitchen-living-dining space was designed to entertain. The kitchen is finished wall to wall with stacked upper cabinets plus crown molding, lighted glass-front uppers, quartz countertop, double built-in ovens, gas cooktop, decorative tile backsplash and an oversized island with seating. A butler's pantry and a fully built-out walk-in pantry with its own seating area keep everything in place, and the laundry room is also finished with custom cabinetry, a sink and extra countertop space. Across the room, a floor-to-ceiling stacked-stone wall anchors the living area, with an electric fireplace and the TV and entertainment system built right in, framed by lighted shelving and cabinets. A dedicated study sits off the dining room with its own work island, wall-to-wall shelving and a wood-planked ceiling. A first-floor bedroom with an en-suite bath makes an ideal guest or in-law suite, plus a powder bath for visitors. Upstairs, the primary suite features a wood beam ceiling and a walk-in closet outfitted with a custom shelving system. The primary bath is built around an oversized walk-in glass shower spanning an entire wall, with dual vanities opposite. Two additional bedrooms, a full bath, and a generous loft with a built-in media center complete the second level. Bidets in the baths. Engineered hardwood in the loft and primary bedroom, wood-look tile downstairs. Outside, a screened lanai with a tongue-and-groove wood ceiling opens to a private paver courtyard. The 2-car garage is already fitted with a NEMA 14-50 EV charging outlet, providing extra storage and parking for your Tesla or other electric car. Best of all: NO FRONT NEIGHBORS. The community pool and amenity center sit directly across the street with plenty of guest parking, and there are water views of John's Lake from the front of the home. Waterside on John's Lake offers something most communities do not: a true lap pool with lane markers for training and distance swimming, plus a separate leisure pool. Add a playground, fitness center, clubhouse and oak-canopied trails with picnic and grill areas leading to a lakefront pier for an evening walk or a little fishing. Minutes from Winter Garden Village, Hamlin and SR-429, with downtown Winter Garden's Plant Street, farmers market and the West Orange Trail just up the road - and Disney a short drive away. Model homes are built to sell a neighborhood. Here is your chance to own one - schedule your private showing today.

16924 Tradewind Point, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code

Almost New & Move-In Ready! Built in 2024, this beautifully maintained corner-unit townhome offers the perfect combination of modern style, comfort, and functionality. Featuring 4 full bedrooms and 3 full bathrooms, the thoughtfully designed floor plan includes a convenient first-floor bedroom, ideal for a home office, guest suite, or private bedroom. The home showcases upgraded tile flooring throughout the main living areas and stylish granite countertops, creating a clean and contemporary feel. The spacious kitchen comes fully equipped with stainless steel appliances, including refrigerator, microwave, and dishwasher, plus a washer and dryer for added convenience. Enjoy Florida living from the screened-in back porch, perfect for relaxing or entertaining while enjoying the outdoors. A private 2-car garage located at the rear of the home provides secure parking and additional storage. Residents enjoy an impressive selection of community amenities, including a resort-style pool, fitness center, gathering area, playground, and community mailbox. With its desirable corner-unit location, modern finishes, flexible first-floor bedroom, and excellent amenities, this almost-new townhome is an exceptional opportunity for both homeowners and investors. Come see why this beautiful 2024 townhome is the perfect place to call home!

14075 Lochend Way, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 1b-A Rep SubDv. ⋅ 34787 Zip Code

Welcome home to this freshly painted, charming Craftsman- inspired residence offering 2193 square feet of thoughtfully designed living space in one of Winter Garden's most desirable communities! This beautifully maintained home features 3 spacious bedrooms, 2 1/2 baths and a versatile loft/bonus room- perfect for a home office, media room or play area. The heart of the home is the open-concept kitchen overlooking the dining and family room, complete with an EXTRAORDINARY walk-in pantry that provides exceptional storage. Tile flooring flows throughout the main living areas, while the primary suite features warm hardwood flooring. Upstairs, the loft and secondary bedrooms are finished with comfortable Berber carpet. Step outside to relax or entertain on the screened lanai, offering the perfect space to enjoy Florida's beautiful weather year-round. Residents enjoy outstanding community amenities, including a resort-style pool, clubhouse, tennis courts, zip line and a dog park. Summerlake also appreciates access to TOP-RATED "A" schools. Conveniently located with easy access to Disney, Universal, Sea World, shopping, dining, major highways and all that Central Florida has to offer, this home truly combines comfort, convenience and an exceptional lifestyle!

7921 Iceland Gull Street, Winter Garden

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

ONE-YEAR HOME WARRANTY AVAILABLE WITH A FULL-PRICE OFFER! Welcome to this beautifully maintained 3-bedroom, 2-bathroom FIRST-FLOOR condo in the gated Southern Pines community of Winter Garden. Featuring a FRESH INTERIOR REPAINT (2026), UPDATED FIXTURES, a bright, open-concept layout, and NO CARPET THROUGHOUT FOR EASY MAINTENANCE, this home is truly move-in ready. Step inside to a spacious open living area offering a dedicated dining room and breakfast nook just off the kitchen. The kitchen features STAINLESS STEEL APPLIANCES, GRANITE COUNTERTOPS, NEUTRAL CABINETRY, and a pantry offering additional storage. The desirable split-bedroom floor plan provides added privacy, with the primary suite positioned on one side of the home and two additional bedrooms with a guest bathroom on the opposite side. All three generously sized bedrooms feature walk-in closets, providing plenty of storage throughout the home. Ideal as a primary residence or investment property, this low-maintenance condo offers excellent rental potential in a desirable Winter Garden location. HOA dues include internet and basic cable, adding further value and convenience. Southern Pines offers an impressive collection of resort-style amenities, including a pool and spa, fitness center, tennis courts, indoor basketball and volleyball courts, playground, dog park, clubhouse, theater room, billiards room, BBQ area, resident car wash station, and on-site management. Conveniently located near highly regarded public schools, Publix, Winter Garden Village, the West Orange Trail, and vibrant Downtown Winter Garden, with easy access to SR-429, Florida’s Turnpike, and major Orlando attractions. Whether you're searching for a comfortable primary residence or a great investment opportunity, this well-located Winter Garden condo delivers space, convenience, amenities, and value.

431 Southern Pecan Circle Unit 101, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Waterside/Johns Lake Ph 1 SubDv. ⋅ 34787 Zip Code

Beyond the gates of Waterside at Johns Lake, where tranquil lakefront living meets the energy of Winter Garden, 16795 Turtle Hatch Drive invites you into a home designed for life at its most memorable. A stately courtyard entrance creates a striking sense of arrival, opening to a grand foyer, soaring ceilings, and sun-filled interiors that feel both impressive and welcoming. This exceptional two-story residence offers 5 bedrooms, 4.5 bathrooms, an expansive bonus room, and an oversized 3-car garage, delivering the space, flexibility, and refined comfort today’s luxury buyer desires. Upgraded tile and hardwood flooring flow through the main living areas, bringing warmth and sophistication to the open-concept great room and dining spaces. Here, quiet mornings transition effortlessly into lively evenings, with generous gathering areas designed for intimate dinners, holiday celebrations, and everything in between. At the heart of the home, the gourmet kitchen is as beautiful as it is functional. Upgraded 42-inch cabinetry, granite countertops, a custom tile backsplash, stainless steel appliances, a gas cooktop, double ovens, and an oversized island with abundant seating create a natural destination for cooking, conversation, and connection. A dedicated workspace with built-in cabinetry and extensive counter space makes working from home, studying, or managing daily life seamless. The main-floor primary suite is a private sanctuary, featuring hardwood flooring, large windows, a custom walk-in closet, and a spa-inspired bath with dual vanities, a soaking tub, and an expansive tiled walk-in shower. Additional bedrooms and baths offer privacy and versatility for guests, extended household members, hobbies, or home offices. Upstairs, the oversized bonus room is a blank canvas for your lifestyle, imagine a cinematic home theater, game lounge, fitness studio, creative space, or secluded guest retreat. Thoughtful details continue in the laundry room with built-in storage, shelving, and a utility sink. Energy-efficient windows, natural gas, and a tankless water heater further enhance everyday comfort and efficiency. And when you step outside you will enjoy your resort-style pool and spa, a private backyard retreat designed to make everyday living feel like a vacation. Beyond the home, Waterside at Johns Lake elevates the experience with gated entry, a lakefront community pool, clubhouse, fitness center, private fishing dock, playground, parks, sidewalks, and scenic walking paths. It is a setting where weekends can begin with a peaceful lakeside walk, continue with an afternoon by the pool, and end beneath a brilliant Florida sunset. The address also places you near the best of Winter Garden and Horizon West, with shopping, acclaimed dining, entertainment, and leading healthcare all within easy reach. Historic Downtown Winter Garden adds timeless charm with boutiques, cafés, restaurants, breweries, the Saturday Farmers Market, Plant Street Market, and Crooked Can Brewing Company. Access to State Road 429, Florida’s Turnpike, and State Road 50 connects you to all things Walt Disney World and Universal Orlando. More than a beautiful residence, 16795 Turtle Hatch Drive is an invitation to live with greater ease, entertain with confidence, and come home to a community that feels worlds away, yet close to everything. Schedule your private tour today! ***Seller is providing up to $5,000 towards mortgage rate incentives when using their Preferred Lender.

16795 Turtle Hatch Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code

Most evenings, unforgettable sunsets spill across the pool and water, casting a breathtaking glow over this premier cul-de-sac homesite. Positioned on an oversized lot with an expansive side yard, this residence enjoys one of Stoneybrook West’s most coveted viewpoints—serene water vistas paired with sweeping Back 9 scenery, including uninterrupted sightlines to the 13th green and 14th tee. Welcome home to an immaculate 3-bedroom, 2-bath split-plan retreat that is truly move-in ready. Step inside and immediately feel the care, quality, and comfort woven throughout. Thoughtful upgrades include brand-new plantation shutters, a custom built-in kitchen nook with outlet, updated light fixtures and fans, and a new refrigerator. Major systems add peace of mind with a roof, HVAC, hot water heater, and interior paint all less than 3 years old. The open living area impresses with a striking white stone accent wall and durable wood-like tile flooring that flows seamlessly through the home. The primary suite features a barn-door entry to the bath and an exceptionally spacious walk-in closet. Outside, your private oasis awaits: a covered lanai overlooking a stunning saltwater pool with sun shelf and water features, all less than 5 years old. The backdrop is pure magic—tranquil water, golf course views, and sunsets that feel like a nightly masterpiece. The fully fenced yard offers fresh tree trimming and an extra-large side yard, ideal for pets, play, or future enhancements. Perfectly situated on a quiet cul-de-sac next to the residents’ gate, this home blends privacy with convenience. Community amenities are exceptional: golf course, playgrounds, pickleball, tennis, basketball, hockey court, resort-style pool, gym, and the Stoneybrook restaurant. Zoned for highly rated schools and just minutes from Winter Garden Village with easy access to the 429, the location is unbeatable. Additional highlights include built-in garage storage and shelving, a fenced yard, and standout curb appeal. This home delivers comfort, style, and a lifestyle that’s hard to match. Call today for a private showing!

2420 Balforn Tower Way, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code

Virtually Staged. Virtually Staged. Best value on Wel Webb Oasis . Experience the renowned 55+ lifestyle at Del Webb Oasis, a world-class, resort-style boutique community offering exclusive amenities, a prime Horizon West location, and natural gas single-family homes nestled in wooded conservation. Residents enjoy a full calendar of social events led by a full-time Lifestyle Director, all centered around a stunning clubhouse. Amenities include a resort-style zero-entry pool with lap lanes and sun shelf, private poolside cabanas, spa, outdoor fire pits with fireworks views, fitness center, tennis and pickleball courts, and a walking trail with exercise stations. Just minutes from Flamingo Crossings, Disney, and major new-construction neighborhoods, Del Webb Oasis is ideally located within one of Central Florida’s fastest-growing master-planned communities, with rising home values throughout the area. Every inch of this thoughtfully designed single-story Palmary floorplan is crafted to make life better, happier, and easier. The home features 3 bedrooms, 2 bathrooms, an open-concept kitchen, café, and gathering room, a covered lanai, and a 2-car garage, offering both comfort and functionality for effortless living and entertaining. Step through the impressive foyer into the heart of the home, where the kitchen, café, and gathering room flow seamlessly to the covered lanai for ideal indoor/outdoor living. The kitchen is appointed with 42” soft-close cabinets, granite countertops, a white center island, built-in stainless-steel appliances, sink and faucet, pendant lighting, and a corner walk-in pantry—perfect for making meals and memories. The private Owner’s Suite features a spacious walk-in closet and a luxurious en suite bathroom with dual-sink granite-topped vanity, private water closet, linen closet, and a luxe super shower. Toward the front of the home, the secondary bedrooms, a full bathroom with shower, and laundry room provide privacy and space for everyone. This home is loaded with functional luxury, including a patio extension, kitchen and owner’s bath, laundry room enhancements, interior doors, electrical upgrades, tile flooring throughout, and professionally designed selections throughout. Located on Sunny Retreat Lane. Get spoiled at Del Webb Oasis—after all, this is your time. Your dream home awaits—schedule your visit today!

13360 Sunny Retreat Lane, Winter Garden

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

Welcome to this charming single story home in Waterleigh, offering 3 bedrooms, 2 bathrooms, and a bright, open concept layout designed for comfortable living and effortless entertaining. The well appointed kitchen overlooks the spacious family room and features stainless steel appliances, generous preparation space, a walk in pantry, and a large center island ideal for casual dining and gatherings. Brick pavers enhance the driveway, welcoming front porch, and covered lanai creating an inviting outdoor space to relax and enjoy the Florida lifestyle. Located in Winter Garden’s desirable Horizon West area near Walt Disney World, Waterleigh offers exceptional amenities, including two clubhouses, resort-style pools, two fitness centers, tennis courts, and a putting green. Schedule your private showing and experience everything this home and community have.

9357 Jaywood Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Villas/Tucker Oaks SubDv. ⋅ 34787 Zip Code

Welcome to your beautifully updated home in the gated community of Winter Garden. This charming residence offers 3 bedrooms, 2.5 baths, 2-car garage, and approximately 1,737 sq. ft. of comfortable living space. In 2025, this home underwent a $53K renovation, featuring a modern kitchen with 42” shaker white cabinets with undermount lighting and quartz counters, stainless steel appliances, and a double oven for added convenience. The renovation also includes kitchen and bathroom upgrades, frameless shower doors, LVP flooring on the upstairs level and stairs, interior and exterior paint, new drapes, and elevated finishes throughout. Additional details include crown molding and 5” baseboards. Enjoy peace of mind with an A/C unit (3 years old) and a new roof (2025). Relax or entertain on the screen-covered patio with pond views. The garage floors feature non-slip coating, and the home includes all-new light fixtures, ceiling fans, and updated lighting. Additional benefits include a security system for added safety and convenience. Community amenities include a pool, playground, dog park, basketball courts, BBQ grills, and walking trails, perfect for everyday enjoyment. Located near Downtown Plant St, Fowler’s Grove, and with convenient access to 429 and the Florida Turnpike, you’re close to dining, shopping, entertainment, and major travel routes. Schedule your showing today!

1424 Scarlet Oak Loop, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Valencia Shores SubDv. ⋅ 34787 Zip Code

Welcome to 301 Valencia Ct., a well maintained 4bedroom 2.5 bath home situated on a large, beautifully landscaped lot with mature trees and established landscaping in desirable Winter Garden. This inviting home offers a comfortable and functional floor plan with plenty of space for everyday living, entertaining and hosting family and friends. Inside a beautiful stone fireplace creates a warm and inviting focal point, while the interior laundry room adds everyday convenience. Step outside to enjoy the spacious backyard, with plenty of room to add a pool, creating the opportunity to design your own private Florida retreat. One of the property’s standout features is its location within the Winter Garden golf cart district, allowing you to enjoy the sought after golf cart lifestyle. Take a golf cart ride toward historic downtown Winter Garden and enjoy its popular restaurants, shops, Farmers market, entertainment, community events and small town charm.Numerous updates have been made to the home to include a new roof in 2021, A/C 2020, master bathroom,guest bathroom remodel in 2023 and Kitchen 2017.

301 Valencia Court, Winter Garden

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