Winter Garden Homes with Trail(s) Amenities

Winter Garden Homes with Trail(s) Amenities

Welcome to Winter Garden, Florida—a hidden gem nestled in the heart of Orange County! This charming city is renowned for its picturesque landscapes, vibrant downtown area, and an abundance of outdoor recreational opportunities. With its delightful blend of small-town charm and modern amenities, Winter Garden is the perfect place for families, retirees, and young professionals alike.

One of Winter Garden's standout features is its extensive network of trails and parks. Residents can enjoy a lifestyle that embraces the great outdoors, thanks to the West Orange Trail, which stretches over 22 miles and winds through scenic landscapes, offering a perfect setting for walking, jogging, and biking. Homes in this area often come with direct access to these trails, making it easy to enjoy the fresh air and beautiful surroundings right from your doorstep.

The city boasts a rich history, evident in its beautifully preserved historic district, where you can find quaint shops, delightful eateries, and a lively farmers market. Community events throughout the year foster a strong sense of belonging, making it easy to connect with neighbors and create lasting friendships.

When it comes to housing, Winter Garden offers a diverse range of options, from charming bungalows to modern family homes, many of which feature coveted trail amenities. Imagine stepping outside to find a network of trails just waiting to be explored—perfect for morning runs or leisurely strolls with family and friends.

Discover the enchanting lifestyle of Winter Garden, where community, nature, and home come together in perfect harmony. Your dream home awaits in this vibrant city!

Newest Winter Garden Homes with Trail(s) Amenities

1362 Union Club Drive, Winter Garden
$910,000
3 Beds ⋅ 3 Baths ⋅ Oakland Parka F1 & F2 SubDv. ⋅ 34787 Zip Code
Welcome to 1362 Union Club Drive in Oakland Park, where a charming park-front setting and inviting outdoor spaces create a wonderful place to call home. A large front porch overlooks the park, providing the perfect spot to enjoy your morning coffee, relax with a book or take in the neighborhood scenery. With no rear neighbor, the home also offers a wonderful sense of privacy. This 3-bedroom, 2.5-bath home features all bedrooms upstairs, including a spacious primary suite that also enjoys peaceful park views. The main living areas are downstairs, with convenient access to the backyard and pool. Outside, you'll find a beautiful pavered pool area that offers plenty of space for relaxing and entertaining. Between the park views from the front porch and the private setting in back, this home offers exceptional outdoor living. Located in the desirable Oakland Park community of Winter Garden, this home presents an opportunity to enjoy one of the area's sought-after neighborhood settings while adding your own personal touches inside.

1362 Union Club Drive, Winter Garden
15688 Orange Harvest Loop, Winter Garden
$473,000
3 Beds ⋅ 3 Baths ⋅ Hickory Hammock SubDv. ⋅ 34787 Zip Code
Welcome to your own piece of paradise in the prestigious dual-gated enclave of Hickory Hammock at Johns Lake! This magnificent 3-bedroom, 2.5-bathroom former builder’s model townhome offers the perfect blend of luxury, comfort, and Florida’s natural beauty. Set amidst THREE breathtaking waterways—the 2,500-acre Johns Lake, Lake Burnett, and Lake Claire—this home delivers a serene lifestyle surrounded by lush landscapes and wildlife. Hickory Hammock is filled with resort-style amenities, including a zero-entry community pool, clubhouse, fitness center, tennis and sand volleyball courts, dog park, playgrounds, parks, walking trails, and a community pier perfect for sunset strolls and lakeside relaxation. Step inside to discover a home that feels brand new. The sellers have just replaced the entire carpet, installed an UV lights for HVAC system, freshly painted the interior, updated the exterior pavers, and installed a brand-new lanai screen, giving the home a crisp, move-in-ready feel from the moment you arrive. The light-filled living area features modern finishes and opens seamlessly to the dining space and gourmet kitchen—an entertainer’s dream with its energy-efficient appliances, stylish countertops, and abundant storage. Enjoy peaceful pond views from your living room and kitchen, making everyday moments feel like a retreat. Upstairs, a versatile loft offers the flexibility for a home office, media room, playroom, or additional guest space. The expansive primary suite is your private sanctuary, complete with a luxurious en-suite bathroom featuring a walk-in shower, dual vanities, and abundant natural light. Designed with exceptional energy efficiency, this home includes block foam insulation, high-performance windows and doors, and a high-efficiency HVAC system, all contributing to lower energy bills and year-round comfort. Perfectly situated in the heart of Winter Garden, you’ll be just minutes from Downtown Winter Garden, Winter Garden Village, Highway 429, the Florida Turnpike, top-rated K–12 schools, Foundation Academy, Montverde Academy, and Windermere Prep. And of course—just a few minutes from Walt Disney World and close to all major shopping, dining, and Orlando attractions. Don’t miss your chance to experience this serene, luxury, resort-style lifestyle. Schedule your private tour today and make this beautifully updated retreat your next home!

15688 Orange Harvest Loop, Winter Garden
11232 Carding Mill Lane, Winter Garden
$690,000
3 Beds ⋅ 3 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Amenities | Close to Park | Covered Lanai. New Construction - November Completion! Welcome to the Sereno at 11232 Carding Mill Lane in Esplanade at McKinnon Groves! This thoughtfully designed single-story home offers the perfect balance of comfort and connection, with an open-concept gourmet kitchen, dining area, and great room that create a bright and inviting gathering space. The spacious primary suite is tucked away for added privacy and features a luxurious bath and generous walk-in closet. Two secondary bedrooms are located near a full bath, making it easy to host guests or create a home office. A covered lanai and private courtyard extend your living space outdoors, while the convenient laundry room, powder bath, and two-car garage add everyday functionality. This home is designed for effortless living with stylish spaces that feel welcoming from the moment you arrive. Additional Highlights Include: 8' doors, blinds, and Cafe Advantage appliances. Photos are for representative purposes only. MLS#O6445005 Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

11232 Carding Mill Lane, Winter Garden
11397 Bourbon Rose Circle, Winter Garden
$840,000
4 Beds ⋅ 4 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Covered Lanai | 3-Car Garage. New Construction - November Completion! Welcome to the Bainbridge at 11397 Bourbon Rose Circle in Esplanade at McKinnon! This thoughtfully designed single-story home offers four bedrooms, three-and-a-half bathrooms, a dedicated study, and a spacious open-concept layout. At the heart of the home, the gourmet kitchen features a large island overlooking the dining area and great room, creating the perfect space for entertaining. The private primary suite is tucked away at the rear of the home and includes a spa-inspired bathroom and expansive walk-in closet. Two secondary bedrooms share a bath near the front of the home, while a private bedroom suite offers added flexibility for guests. Elegant tray ceilings, crown molding, and 8-foot interior doors enhance the home's appeal, while the covered lanai extends the living space outdoors. Additional Highlights Include: powder bath in place of storage. Photos are for representative purposes only. MLS#O6444985 Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

11397 Bourbon Rose Circle, Winter Garden
14169 Avenue Of The Groves, Winter Garden
$375,000
2 Beds ⋅ 3 Baths ⋅ Signature Lks-Pcl 01d Ph 01 SubDv. ⋅ 34787 Zip Code
Resort-style ease meets everyday comfort in this move-in ready Independence townhome that lives like a single-family home. Two bedroom, two and a half bath, with both bedrooms featuring private en suites.  Enjoy a welcoming front porch for morning coffee and an expansive private courtyard that truly feels like your own backyard, with direct access to a 2-car garage—giving you outdoor living space, privacy and functionality you don’t always find in townhome living. **And when the sun goes down, enjoy the magic of Magic Kingdom fireworks right from home.** Fresh exterior paint and newer roof, inside brand new carpet, newer Trane HVAC, upgraded LG Smart stainless steel appliances app controlled plus W/D (with added features like bio defense light) set a clean, modern tone. An open-concept layout features a kitchen with an island breakfast bar that flows seamlessly into the dining and living areas, keeping everyone connected. Soaring ceilings and abundant natural light from numerous windows create a bright, airy feel throughout. Smart-home conveniences include a Ring security system with remote monitoring and My Q remote-access garage controls, giving you added convenience whether you’re home or away. The HOA covers lawn care, so your weekends are truly yours. Step outside and you’ve got a Gazebo on corner to enjoy lakefront picnics, two clubhouses in close distance where lots of community parties happen with resort pools, fitness center, game room, holiday events, giant open lawns for sports and activities, walking and biking trails, multiple playgrounds and parks, basektball and tennis courts, dog parks, a community boat ramp onto Lake Hancock, access to a PokemonGo Pokestop, and that signature Indenpendence reflecting pond. (Lake Views from Master BD and front porch). All the polish of a model home, with the space and feel of a single family, plus the low maintenance lifestyle you want. Just minutes from shopping, groceries, and dining, with Walt Disney World approximately 20 minutes away. Everyday convenience and weekend magic, right at your doorstep. Organized community events, including festivals, pool events, food-truck nights and Independence's annual fireworks event.

14169 Avenue Of The Groves, Winter Garden
150 Hammock Preserve Loop, Oakland
$879,000
4 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Some homes simply sit in a neighborhood. This one feels like it belongs there. Welcome to 150 Hammock Preserve Loop, a 2023 Rockwell Homes residence tucked into the heart of Oakland Park, where the front porch looks out toward mature oak trees and the best parts of the Winter Garden lifestyle are never far from home. Step inside and you’re immediately greeted by a dedicated office to the left of the entry, creating the perfect work-from-home space while keeping it separate from the main living areas. Throughout the home, thoughtful custom updates give each space a personality of its own. The primary suite is conveniently located on the main floor, while the additional bedrooms and spacious loft are upstairs, creating a layout that offers both separation and flexibility. A rare three-car garage provides the extra space that can be difficult to find in Oakland Park, whether you need room for vehicles, golf carts, bikes, storage, or all of the above. Out back, the generous yard offers plenty of room to create your own outdoor retreat, including space for a future pool. But what makes this home especially difficult to replicate is everything beyond the front door. Oakland Park is one of Winter Garden’s most sought-after communities for a reason. Tree-lined streets, front porches, parks, playgrounds, two resort-style community pools, a clubhouse, dog park, waterfront spaces, and miles of trails create a neighborhood designed to actually be enjoyed. Hop on your bike and connect to the West Orange Trail, or grab the golf cart and head toward Downtown Winter Garden for a morning at the Farmers Market, drinks at Crooked Can, dinner along Plant Street, boutique shopping, community events, and everything surrounding Plant Street Market. Here, weekends can start with coffee on the front porch beneath the oaks, turn into an afternoon by the pool or on the trail, and end with a golf cart ride into Downtown Winter Garden. Built in 2023, filled with custom touches, complete with a dedicated office, rare three-car garage, and a backyard ready for what comes next, 150 Hammock Preserve Loop offers more than a beautiful home. It offers the Oakland Park lifestyle that makes this neighborhood so special.

150 Hammock Preserve Loop, Oakland
6379 Argent Wood Drive, Winter Garden
$469,690
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Under Construction. Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! The new construction Foxtail Interior Unit townhome features 3 bedrooms, 2 full bathrooms, a powder room, an open concept kitchen, café and gathering room, a private courtyard, a 2-car rear-facing garage and our Move-In Ready package with includes a refrigerator, washer, dryer, and 2” faux wood blinds. The first floor is ideal for entertaining, featuring a spacious gathering room, café and kitchen, with a large center island, storage pantry, Trenton Burlap cabinets, a decorative tile backsplash, quartz countertops and Whirlpool stainless-steel kitchen appliances – including a refrigerator. A powder room and laundry on the first floor add to the thoughtful convenience. Enjoy entertaining loved ones from your private, fenced rear courtyard. After a long day, retreat upstairs to your private oasis. The Owner's Suite features a spacious walk-in closet and en suite bathroom with a double sink quartz-topped vanity, private water closet and a walk-in shower. Two additional bedrooms, the secondary bathroom and extra storage offered by a linen closet are on the opposite side of the second floor, offering privacy and space for everyone. Professionally curated design finishes for this popular Foxtail townhome include window blinds, luxury wood-look vinyl plank flooring throughout the first-floor, tile in the bathrooms, and soft, stain-resistant, Shaw brand carpet in the bedrooms and second floor living areas, and so much more.

6379 Argent Wood Drive, Winter Garden
14371 Shocklach Drive, Winter Garden
$700,000
3 Beds ⋅ 2 Baths ⋅ Latham Park North SubDv. ⋅ 34787 Zip Code
Every single day, you’ll experience the ultimate Central Florida lifestyle in your own private backyard paradise. Tucked into the coveted Latham Park community of Winter Garden, just two miles from Disney’s Magic Kingdom, this pristine 2018-built home pairs luxurious outdoor living with unbeatable convenience to world-class entertainment, shopping, and dining. Surrounded by updated curb appeal, mature landscaping, and a quiet neighborhood setting, it offers a rare combination of comfort, style, and resort-style amenities right at home. Inside, the light-filled floor plan feels crisp, elevated, and completely turn-key, highlighted by elegant crown molding and durable wood-look tile floors running throughout the main living areas. High tray ceilings accentuate the main open-concept living and dining spaces, leading seamlessly into a dedicated flex space. Showcasing true Florida indoor-outdoor living, the home features both a standard sliding door and a triple sliding glass door that opens directly from the flex space out to the pool area. At the center of it all is a modern chef’s kitchen designed for both quiet mornings and hosting friends. It boasts 42-inch cabinets, sleek quartz countertops, under-cabinet accent lighting, a gas range, and premium stainless steel appliances. Conveniently nearby, an oversized laundry room comes fully equipped with a washer and dryer while providing exceptional extra storage space. For total peace of mind and remarkable efficiency, the home is secured with a SimpliSafe security system, equipped with a tankless water heater, and features fully paid-off solar panels for ultra-low electricity bills. The primary suite serves as your private sanctuary, featuring a custom built-in walk-in closet system and a beautifully appointed primary bathroom complete with a luxurious, walk-in shower. Two additional spacious bedrooms with luxury vinyl flooring provide exceptional flexibility for family, guests, or a dedicated home office setup. Step out back into your personal outdoor oasis—a custom screen-enclosed pool deck featuring a stunning heated saltwater pool and spa, built-in controllable LED lighting overhead and within the enclosure, and a Char-Broil outdoor kitchen perfect for weekend barbecues. The fully fenced backyard ensures a private, safe space for relaxation or outdoor fun. Beyond your doorstep, enjoy Latham Park’s vibrant community events, pool, playground, and spectacular views of the Disney fireworks right from within the neighborhood—plus access to top-tier schools including Panther Lake Elementary, Hamlin Middle, Horizon High, and Windermere Prep. From private poolside relaxation to nightly magic nearby, this is a rare gem in one of Winter Garden’s most sought-after pockets.

14371 Shocklach Drive, Winter Garden
2696 Bobcat Chase Boulevard, Oakland
$515,000
3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Welcome home to this beautifully maintained 3-bedroom, 2.5-bath home in the highly sought-after Longleaf at Oakland community! From the moment you arrive, you will appreciate the inviting feel, thoughtful layout, and pride of ownership throughout. Inside, enjoy spacious bedrooms, a versatile upstairs loft perfect for a home office, media room, or additional living space, and a comfortable family room designed for everyday living and entertaining. Step outside to a wonderful backyard and porch area, with both the family room and porch pre-wired for speakers—perfect for creating an effortless indoor-outdoor entertaining experience. The two-car garage even features an electric vehicle charging outlet. The location is hard to beat— take a quick 5-minute walk to the West Orange Trail, enjoy the shops, dining, and charm of Downtown Winter Garden just 10 minutes away, and reach the Florida Turnpike in minutes. Beautifully cared for, ideally located, and truly move-in ready—this is the Oakland home you’ve been waiting for!

2696 Bobcat Chase Boulevard, Oakland
910 Trowman Aly, Winter Garden
$638,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to this modern 3-bedroom, 2 and 1/2-bath residence, 1650 square feet located in McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. This Home has a nice welcoming front porch and showcases timeless architecture, upscale designer finishes. Step inside to discover soaring ceilings, beautiful luxury vinyl plank flooring throughout the main living areas. At the heart of the home on the 2nd Story, the Executive kitchen features custom cabinetry with updated hardware, quartz countertops, an island, a gas range, vent hood, tile backsplash, and abundant storage. The open-concept design flows effortlessly into the spacious family room with a Balcony to have coffee in the morning or tea in the evening. The upstairs has a lofty feel has a nice living space. Cathedral ceilings, walk-in closet. One of Winter Garden's most desirable lifestyles. This award-winning, master-planned community of Oakland Park features tree-lined streets, scenic parks, resort-style pools, playgrounds, and miles of walking and biking trails, including direct access to the renowned West Orange Trail. Residents enjoy a true neighborhood atmosphere just a golf cart ride from Historic Downtown Winter Garden, where you'll find award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, and the nationally recognized Winter Garden Farmers Market close to Winter Garden Village at Fowler Groves the outdoor Mall and the Orlando International Airport. With convenient access to Florida's Turnpike, SR-429, 408, to downtown Orlando, and Central Florida's world-famous attractions and Themed Parks, this exceptional residence offers the perfect blend of luxury, convenience, community, and lifestyle.

910 Trowman Aly, Winter Garden
5751 New Independence Parkway, Winter Garden
$405,000
2 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
Well-maintained and thoughtfully updated, this New Independence townhome offers the perfect combination of style, comfort, and low-maintenance Florida living, all while located in a highly desirable community. Step inside to find updated flooring throughout, plantation shutters, and a bright, inviting layout designed for effortless everyday living. The renovated primary suite adds a modern, elevated touch, while the home’s thoughtful design provides the perfect setting for both relaxing and entertaining. Outside, discover a beautifully organized backyard oasis—a private space to enjoy your morning coffee, host friends, or simply take advantage of the Florida sunshine. And the lifestyle extends well beyond the property. New Independence offers an impressive collection of amenities, including two resident clubhouses, two resort-style pools with cabanas and grills, a whirlpool spa, two fitness centers, tennis and basketball courts, parks, playgrounds, and more than 6 miles of walking, running, and biking trails. Residents also have private lake access with boat ramps and on-lake ski ramps serving the lakes between Lake Hancock and Lake Speer. The community also features two dedicated dog parks, including separate areas for large and small dogs. Additionally, the HOA also includes basic high-speed internet and cable TV service, adding even more value to the community’s amenities package. Location is a major advantage; this home is only minutes from the popular Hamlin shopping and dining district, as well as the Winter Garden Village, downtown Winter Garden, and major roadways. Enjoy convenient access to some of the area’s best restaurants, shopping, and everyday necessities while still coming home to a peaceful, established community. Updated. Turnkey. Ideally located. And ready for its next owner.

5751 New Independence Parkway, Winter Garden
8174 Bluejack Oak Drive, Winter Garden
$465,900
4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 2c 2d 2e SubDv. ⋅ 34787 Zip Code
LAKEFRONT LUXURY IN SUMMERLAKE! Stunning 4BR/3BA townhome with bonus room, open concept living, brand new roof, state of the art appliances & decorative lighting included! Enjoy breathtaking lake views, nightly Disney fireworks, and a private PVC fenced brick paver courtyard perfect for morning coffee or relaxing. Spacious 2 car garage. Resort style amenities include clubhouse, gym, pool, soccer field, walking trails, tennis court, basketball court, playground, zip line & fishing dock. Walking distance to the Orange County National Golf Center, minutes to Disney, Downtown Winter Garden, endless dining & shopping. A MUST SEE! Buyer to verify room sizes and all measurements. Public records reflect 3BR/2BA; actual configuration is 4BR/3BA plus bonus room

8174 Bluejack Oak Drive, Winter Garden
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