Winter Garden Homes with Trail(s) Amenities

Winter Garden Homes with Trail(s) Amenities

Welcome to Winter Garden, Florida—a vibrant city nestled in the heart of Orange County, where the charm of small-town living meets the excitement of modern amenities. With its picturesque streets lined with historic buildings, Winter Garden boasts a rich heritage that is beautifully complemented by its thriving community spirit. The city is known for its lush parks, scenic lakes, and a bustling downtown area filled with delightful shops, restaurants, and entertainment options.

One of the standout features of Winter Garden is its commitment to outdoor living, making it a haven for nature enthusiasts and families alike. The city is home to an extensive network of trails that wind through stunning landscapes, offering residents ample opportunities for biking, jogging, and leisurely strolls. Imagine waking up each day and stepping out your front door to explore miles of scenic paths that lead you through the beauty of Florida’s natural surroundings.

If you're looking for a home that embraces this active lifestyle, you'll find a variety of properties in Winter Garden equipped with trail amenities. Many neighborhoods feature direct access to these trails, allowing you to enjoy the great outdoors right from your doorstep. Whether you’re seeking a cozy single-family home or a modern townhouse, Winter Garden's real estate market offers something for everyone.

With its blend of community charm, outdoor adventure, and a welcoming atmosphere, Winter Garden is not just a place to live—it's a place to thrive. Come discover your dream home in this enchanting city where trails and tranquility await!

Newest Winter Garden Homes with Trail(s) Amenities

4 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. What's Special: Corner Lot | Dedicated Study | Oversized Garage | Gourmet Kitchen. New Construction – December Completion! Built by America's Most Trusted Home Builder. Welcome to the Saint Clair at 12940 Harvest Rain Avenue in Harvest at Ovation! This spacious single-story home offers a thoughtfully designed open-concept layout centered around an impressive great room that flows seamlessly into the dining area and gourmet kitchen with a large island. The private primary suite features a luxurious bathroom and generous walk-in closet. Three secondary bedrooms, a dedicated study, and multiple full bathrooms provide flexibility for work, guests, or hobbies. Direct access to the laundry area through the convenient drop zone just off the two-car garage provides added convenience. Enjoy indoor-outdoor living with the expansive lanai, perfect for relaxing or entertaining. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights include: Tray ceiling package, whole house 8' interior doors, study in place of flex, deluxe primary bathroom, outdoor kitchen rough-in, cushion close doors and drawers kitchen cabinet package, and whole house blinds. Photos are for representative purposes only. MLS#O6430978

12940 Harvest Rain Avenue, Winter Garden

6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 SubDv. ⋅ 34787 Zip Code

Virtually Staged. The photo showing Disney fireworks is the only pic that is virtually staged. This beautiful Hancock Lake family friendly home is custom built for maximum lakefront enjoyment including a private covered dock protecting a 20’ +/- boat and 2 jet skis. Motor boat or pontoon around the lake, drop a line in or ski on one of the best skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, manicured gardening beds for your green thumb and plenty of room for outdoor games and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry, cabana bath and a custom salt pool showcasing a water slide, Fiber optic lighting, solar heated and whimsical Disney characters embedded in the rock’s facade. Relax to lake views, or pull down the projector screen for a movie then watch the Disney’s fireworks nightly over the lake. The home has a freshly painted exterior and interior with crown trim throughout. The Kitchen space is designed for multiple chefs with newer appliances, walk-in pantry, island and informal seating. The first level’s primary suite with patio access was previously a media room complete with surround sound that remains intact. The loft with a balcony overlooking the patio and lake is prepped for entertaining. Two additional ensuites, 3 more bedrooms and a laundry room are also on the upper level. Both A/C Systems, all patio doors, reinforced exterior balcony railings and LR/DR bamboo engineered hardwood flooring are updated. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy.

7301 Wild Blackberry Trail, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Cypress Reserve Ph 1 SubDv. ⋅ 34787 Zip Code

Welcome to luxury living at its finest! Perfectly positioned on the largest homesite in the community, this exceptional 4 bedroom home, fully equipped with oversized loft and theatre/bonus room, sits on a premium 1/3-acre oversized lot with tranquil green space views, offering both privacy and room to enjoy Florida living. From the moment you arrive, you’ll be impressed by the freshly painted exterior, upgraded landscaping, elegant stone accents, and expansive paver driveway. Inside, thoughtful upgrades and quality craftsmanship are showcased throughout, including 8-foot interior doors, crown molding, custom window casings and sills, upgraded wood flooring, premium carpeting, and designer tray ceilings in both the dining room and the luxurious owner’s suite. The heart of the home is the stunning gourmet kitchen, featuring upgraded cabinetry, a California-style countertop, a vented exterior range hood, motion-activated faucet, and abundant space for entertaining and everyday living. The spacious owner’s retreat provides a peaceful escape with its elegant tray ceiling and spa-like atmosphere, while the open-concept layout is designed for both comfort and entertaining. This home is full of valuable efficiency upgrades, including a radiant barrier roof for exceptionally low energy costs, gutters, and numerous quality enhancements that provide peace of mind for years to come. This is a rare opportunity to own one of the community’s most desirable homesites, combining luxury finishes, energy efficiency, and an unbeatable oversized lot with beautiful green space views. A truly exceptional home, with LOW HOA and A RATED SCHOOL-ZONES that is as impressive inside as it is out. Schedule your showing today!

13852 Jomatt Loop, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1b SubDv. ⋅ 34787 Zip Code

Welcome to your beautiful water-view home in the highly sought-after Waterleigh community! This stunning property offers the convenience of single-story living with 4 bedrooms, 3 full bathrooms and picturesque water views. Perfectly positioned with a large green space in front and stunning pond and lake views in the back, this home features a gated backyard offering added privacy and convenient outdoor access. End your evenings by enjoying a glimpse of Disney's nightly fireworks right from your own backyard. Inside, you'll find numerous recent updates, including a new HVAC system, brand-new carpet, a new refrigerator, new dishwasher, new garbage disposal, and a new washer and dryer, making this home truly move-in ready! One of the many perks of living in Waterleigh is that lawn care is included in the HOA, allowing you to spend more time enjoying the exceptional resort-style amenities. Residents have access to resort-style pools, state-of-the-art fitness centers, beautiful clubhouses, mini golf, a dog park, expansive sports fields, multiple playgrounds, beach volleyball, tennis courts, a community dock, and scenic walking trails and picnic areas, creating the perfect setting for an active and relaxing lifestyle. Ideally located in the heart of Horizon West, just minutes from Walt Disney World with quick access to SR-429, this home offers easy commuting throughout Central Florida while being zoned for highly rated schools. This is a rare opportunity to own a beautifully updated home with exceptional views in one of Horizon West's most desirable communities. Schedule your private showing today!

16130 Wind View Lane, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code

Under Construction. What's Special: Dedicated Study | Close to Amenities | Covered Lanai. New Construction - December Completion! Welcome to the Cresta at 17742 Sedona Street in Esplanade at McKinnon Groves! Welcome home to a thoughtfully designed floorplan that balances open-concept living with comfortable private spaces. The spacious great room serves as the heart of the home and flows seamlessly into the dining area and gourmet kitchen, complete with upgraded appliances, abundant cabinetry, and a large center island that is perfect for entertaining. Extended vinyl flooring runs throughout the main living areas, while elegant tray ceilings and 8' interior doors add the perfect touch. Just off the foyer, the study features beautiful French doors, creating an ideal space for a home office. The private primary suite is tucked away at the rear of the home and offers a spacious bedroom, luxurious bath, and generous walk-in closet. Two additional bedrooms, one with an en-suite, and an additional full bathroom provide comfortable accommodations for family or guests. Enjoy indoor-outdoor living with sliding glass doors leading to the covered lanai, perfect for relaxing or gathering with friends. Completing the home is a spacious three-car garage, dedicated laundry room, and a charming courtyard entry that enhances the home's curb appeal. Additional Highlights Include: 42" cabinetry in kitchen and laundry room, and whole house blinds. Photos are for representative purposes only. MLS#O6427570 - Esplanade at McKinnon Groves brings resort-style living to Winter Garden with beautifully designed open-concept homes set among natural views. This vibrant gated community offers a lifestyle centered on wellness, unique experiences, and signature amenities that make every day feel like a getaway. The Venue will feature a fitness center, movement studio, treatment room, lifestyle spaces, outdoor terrace seating, Bahama bar, and a resort pool with a spa and cabanas. You’ll also enjoy fireside seating, yoga and flex lawns, pickleball, tennis and bocce courts, a bark park, rose garden, and a trailhead connecting miles of equestrian and walking trails. Concierge services and year-round events elevate the experience even more. With zoning for Lake County public schools, this community blends everyday convenience with resort-style comfort!

17742 Sedona Street, Winter Garden

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! Introducing the Benton bungalow, a brand-new home that includes 3 spacious bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-load attached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. This inviting space is perfect for both everyday living and entertaining. The kitchen boasts a large center island, a convenient storage pantry, and top-of-the-line Whirlpool stainless steel appliances—including a refrigerator. White cabinetry, decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite, two additional bedrooms, a second full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a frameless glass-enclosed shower, quartz-topped dual vanity, and linen closet. Throughout the first floor, enjoy the beauty of Wood-Look Luxury Vinyl Plank flooring, while tile enhances the laundry room and bathrooms. Plush, stain-resistant Shaw carpet covers the stairs and bedrooms, adding comfort and style. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

16827 Evermore Alley, Winter Garden

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 Exterior Unit townhome features 3 bedrooms, 2 full bathrooms, a powder room, an open concept kitchen, café and gathering room, a private courtyard, and a 2-car rear-facing garage. The first floor is ideal for entertaining, featuring a spacious gathering room, café and kitchen, with a large center island, storage pantry, white cabinetry, 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 2” faux wood window blinds, Whirlpool washer and dryer, wood-look luxury vinyl plank flooring throughout the first floor, tile flooring in the laundry room and bathrooms, and soft, stain-resistant, Shaw brand carpet in the bedrooms, and so much more. This new construction townhome perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind. Schedule your tour today!

6355 Argent Wood Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code

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! Introducing the Haddock bungalow, a brand-new home that combines modern design and ultimate comfort, featuring 3 spacious bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-load attached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. This inviting space is perfect for both everyday living and entertaining. The kitchen boasts a large center island, a convenient storage pantry, and top-of-the-line Whirlpool stainless steel appliances—including a refrigerator and vented microwave. Tilden white cabinetry, decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite, two additional bedrooms, a second full bathroom, a loft, and a laundry closet. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a frameless glass-enclosed shower, quartz-topped dual vanity, private water closet, and linen closet. Throughout the entire first floor enjoy wood-look luxury vinyl plank flooring, while tile flooring spans the laundry room and bathrooms. Plush, stain-resistant Shaw carpet covers the stairs, loft, and bedrooms, adding comfort and style. Smart home features include a smart thermostat, a smart doorbell, and additional LED downlights—ensuring your home is as connected as it is stunning. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

16803 Evermore Alley, Winter Garden

4 Beds ⋅ 5 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code

Under Construction. What's Special: Gourmet Kitchen | 3-Car Garage | Dedicated Home Office. New Construction - December Completion! Welcome to the Bradley at 11341 Bourbon Rose Circle in Esplanade at McKinnon Groves! This thoughtfully designed home features a spacious open-concept layout with a bright great room, dining area, and gourmet kitchen at the heart of the home, creating the perfect space for entertaining and everyday living. The private primary suite offers a relaxing retreat with an elegant bathroom and generous walk-in closet, while three secondary bedroom suites provide comfort and privacy for guests. A versatile flex room adds extra space for a home office, hobby room, or lounge, and the covered lanai extends living outdoors for seamless indoor-outdoor enjoyment. A three-car garage and laundry room complete the home. Additional Highlights include: Tray ceiling package, shower in place of tub in bath three and four, pool pre-wire, and outdoor kitchen rough-in. Photos are for representative purposes only. MLS#O6427362 Esplanade at McKinnon Groves brings resort-style living to Winter Garden with beautifully designed open-concept homes set among natural views. This vibrant gated community offers a lifestyle centered on wellness, unique experiences, and signature amenities that make every day feel like a getaway. The Venue will feature a fitness center, movement studio, treatment room, lifestyle spaces, outdoor terrace seating, Bahama bar, and a resort pool with a spa and cabanas. You’ll also enjoy fireside seating, yoga and flex lawns, pickleball, tennis and bocce courts, a bark park, rose garden, and a trailhead connecting miles of equestrian and walking trails. Concierge services and year-round events elevate the experience even more. With zoning for Lake County public schools, this community blends everyday convenience with resort-style comfort!

11341 Bourbon Rose Circle, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code

Under Construction. What's Special: Corner Lot | Close to Park | Dedicated Study | Spacious Kitchen. New Construction – September Completion! Welcome to the Caicos at 11275 Silver Trumpet Loop in Esplanade at McKinnon Groves! This welcoming new home showcases an airy open-concept design where the great room, kitchen, and dining area come together to create a seamless space for gathering and everyday living. Just beyond the great room, the covered lanai extends your living area outdoors. The private primary suite is tucked away at the rear of the home and includes a well-appointed bathroom and generous walk-in closet. A secondary bedroom, full bathroom, and versatile study provide comfortable space for guests, hobbies, or a home office, while the convenient laundry room and two-car garage add everyday functionality. Additional Highlights Include: Double pocket doors at study, extended lanai, garden fence, and extended tile. Photos are for representative purposes only. MLS#O6427248 - Esplanade at McKinnon Groves brings resort-style living to Winter Garden with beautifully designed open-concept homes set among natural views. This vibrant gated community offers a lifestyle centered on wellness, unique experiences, and signature amenities that make every day feel like a getaway. The Venue will feature a fitness center, movement studio, treatment room, lifestyle spaces, outdoor terrace seating, Bahama bar, and a resort pool with a spa and cabanas. You’ll also enjoy fireside seating, yoga and flex lawns, pickleball, tennis and bocce courts, a bark park, rose garden, and a trailhead connecting miles of equestrian and walking trails. Concierge services and year-round events elevate the experience even more. With zoning for Lake County public schools, this community blends everyday convenience with resort-style comfort!

11275 Silver Trumpet Loop, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code

Under Construction. What's Special: Dedicated Study | Covered Lanai | Close to Park. New Construction - September Completion! Welcome to the Caicos at 11259 Silver Trumpet Loop in Esplanade at McKinnon Groves! This charming new home features a kitchen that overlooks the dining area and great room, creating an open and connected space for everyday living and entertaining. Step outside to the covered lanai, perfect for enjoying morning coffee or relaxing in the Florida sunshine. The private primary suite is situated at the rear of the home and features a well-appointed bathroom and generous walk-in closet. A secondary bedroom, full bathroom, versatile study, convenient laundry room, and two-car garage complete this well-balanced home designed for today's lifestyle. Additional Highlights Include: Double pocket doors at study, single pocket door at secondary bedroom to bath, extended lanai, garden fence, and extended tile flooring. Photos are for representative purposes only. MLS#O6427237 - Esplanade at McKinnon Groves brings resort-style living to Winter Garden with beautifully designed open-concept homes set among natural views. This vibrant gated community offers a lifestyle centered on wellness, unique experiences, and signature amenities that make every day feel like a getaway. The Venue will feature a fitness center, movement studio, treatment room, lifestyle spaces, outdoor terrace seating, Bahama bar, and a resort pool with a spa and cabanas. You’ll also enjoy fireside seating, yoga and flex lawns, pickleball, tennis and bocce courts, a bark park, rose garden, and a trailhead connecting miles of equestrian and walking trails. Concierge services and year-round events elevate the experience even more. With zoning for Lake County public schools, this community blends everyday convenience with resort-style comfort!

11259 Silver Trumpet Loop, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code

Under Construction. What's Special: Dedicated Study | Close to Park. New Construction - September Completion! Welcome to the Caicos at 11279 Silver Trumpet Loop in Esplanade at McKinnon Groves! This charming new home has a spacious great room that connects seamlessly to the kitchen and dining area, creating a bright central space for gathering. Just off the great room, the covered lanai provides the perfect spot to relax and enjoy the outdoors. The private primary suite features a well-appointed bathroom and generous walk-in closet, while a secondary bedroom and full bathroom provide comfortable accommodations for guests. A versatile study, convenient laundry room, and two-car garage complete this functional and inviting home. Additional Highlights Include: Garden fence, laundry package, GE refrigerator, 8' interior doors, and extended vinyl flooring. Photos are for representative purposes only. MLS#O6427229 - Esplanade at McKinnon Groves brings resort-style living to Winter Garden with beautifully designed open-concept homes set among natural views. This vibrant gated community offers a lifestyle centered on wellness, unique experiences, and signature amenities that make every day feel like a getaway. The Venue will feature a fitness center, movement studio, treatment room, lifestyle spaces, outdoor terrace seating, Bahama bar, and a resort pool with a spa and cabanas. You’ll also enjoy fireside seating, yoga and flex lawns, pickleball, tennis and bocce courts, a bark park, rose garden, and a trailhead connecting miles of equestrian and walking trails. Concierge services and year-round events elevate the experience even more. With zoning for Lake County public schools, this community blends everyday convenience with resort-style comfort!

11279 Silver Trumpet Loop, Winter Garden

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