Winter Garden Homes with Trail(s) Amenities

Winter Garden Homes with Trail(s) Amenities

Welcome to Winter Garden, Florida—a vibrant and charming city nestled in the heart of Orange County. Known for its picturesque landscapes and rich history, Winter Garden seamlessly blends small-town charm with modern conveniences. With a thriving downtown area filled with boutique shops, delightful eateries, and an array of community events, it's no wonder that Winter Garden is a sought-after destination for families and individuals alike.

One of the standout features of Winter Garden is its incredible access to outdoor recreational opportunities. The city is home to a network of scenic trails, perfect for walking, jogging, or biking. Imagine stepping out of your front door and onto a beautiful trail that winds through lush parks and serene lakes. Homes in Winter Garden often come equipped with trail amenities, allowing residents to enjoy an active lifestyle while soaking in the natural beauty that surrounds them.

The community is also known for its excellent schools, friendly neighborhoods, and a strong sense of community spirit. Whether you're exploring the historic downtown or enjoying a weekend at the local farmers' market, you'll find that Winter Garden offers a welcoming atmosphere that feels just like home.

If you're searching for a place where you can enjoy both the tranquility of nature and the vibrancy of community life, look no further than Winter Garden. With its beautiful homes and inviting trails, it’s an ideal setting for those who appreciate a balanced lifestyle. Come discover the charm of Winter Garden, where your dream home awaits!

Newest Winter Garden Homes with Trail(s) Amenities

13055 Sandcastle Drive, Winter Garden
$874,990
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Step into the Renown, a new construction, single-story home situated within walking distance of the amenity center offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an enclosed flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where soft-close cabinetry with clear glass uppers meets luxurious quartz countertops and a decorative tile backsplash. Thoughtfully designed features like easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including double ovens and a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a built-in bench and rain shower head, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, matte black hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

13055 Sandcastle Drive, Winter Garden
5685 New Independence Parkway, Winter Garden
$464,999
3 Beds ⋅ 3 Baths ⋅ Signature Lakes, Independence SubDv. ⋅ 34787 Zip Code
INDEPENDENCE Community! This END unit is nothing like you have ever seen in the neighborhood before!! Offering stylish finishes, thoughtful improvements, and an exceptional location, this MOVE IN READY home is the perfect blend of comfort, functionality, and modern living. EXTENSIVELY UPDATED!! This home features a freshly painted exterior and interior (2024), updated trim, new 6-inch baseboards, 3-inch door casings, and upgraded lighting, ceiling fans, and fixtures throughout (2024). In 2023, the home received luxury vinyl plank flooring on the main level and in the upstairs bathrooms, a fully remodeled kitchen, an updated laundry area, and a new water heater. The high-efficiency TRANE 20-SEER A/C system (2020) adds year-round comfort and efficiency. Luxury Vinyl Plank flooring added to the stairs and upstairs this year! (2026) NO CARPET!! New refrigerator (2026!) The stunning remodeled kitchen is the heart of the home, featuring quartz countertops, solid wood cabinetry with soft-close drawers and crown molding, a farmhouse sink, a walk-in pantry, and an oversized island complete with a wine fridge. Stainless steel appliances complete this stylish and functional space, offering plenty of storage and room to gather. The open-concept layout flows seamlessly into the dining area and spacious living room, where abundant natural light creates a warm and inviting atmosphere. A convenient half bath on the main level adds to the home's everyday functionality.Upstairs, you'll find three comfortable bedrooms and two upgraded bathrooms featuring refreshed vanities, new mirrors, updated lighting, and comfort-height, skirted self-cleaning toilets. Outside, enjoy the added privacy and curb appeal of this end-unit townhome, complete with a covered front porch, block and stucco construction extending to the roof, and a two-car rear-facing garage with additional ceiling storage installed in 2021. The outdoor living space is just as inviting, featuring a private, fenced paver patio with green space beyond the fence—perfect for morning coffee, relaxing evenings, or entertaining guests. Additional improvements include all-new appliances (2021), new window screens and blinds (2021), a wired security system, and energy-efficient lighting throughout. Located in a highly rated A-rated school district, Independence offers desirable community amenities and a welcoming neighborhood atmosphere. Conveniently situated in the heart of Winter Garden/Horizon West, you'll enjoy easy access to shopping, dining, entertainment, theme parks, SR-429, and other major roadways. With extensive updates, modern finishes, added privacy, and an outstanding location, this beautifully maintained townhome is ready for its next owner. Don't miss your opportunity to make this exceptional property your own—schedule your private showing today!

5685 New Independence Parkway, Winter Garden
5522 New Independence Parkway, Winter Garden
$499,900
3 Beds ⋅ 2 Baths ⋅ Signature Lakes, Independence SubDv. ⋅ 34787 Zip Code
Independence ** Rare floor plan for Independence with 3 bedrooms and +/-17x12' DEN or living room space ** FRESHLY painted neutral soft white interior and BRAND NEW LAMINATE FLOORING in the 3 bedrooms ** 19x10' Florida Room with AC and heat ** Primary bedroom has 2 walk in closets with built in white shelving & ensuite primary bath with two sinks, granite counters, garden tub and separate shower ** The kitchen has a large cooking island with granite counters and includes the stainless steel stove, refrig and dishwasher ** Laundry room with built in white shelving and washer and dryer included ** Ceiling fans in every room ** Great completely fenced back yard with Florida room and brick paver patio area 2018 ** 2 car attached garage ** Lovely front porch with brick patio pavers ** Beautiful Florida Room Other upgrades include: NEW Trane A/C SYSTEM 10/2025, NEW white vinyl fence and gates 2/2024, NEW exterior brass whole house water shutoff valve 3/2026, NEW garage door system, SPRINGS 2/2021 and garage door opener 10/2024 ** LOW HOA fees $194.69 incl cable & internet which currently includes HBO and Max! Incredible amenities including 2 community pools, play areas, a lg community park plus other neighborhood green space and play areas thru-out the neighborhood, loads of sidewalks & conservation thru-out... All room measurements are approximate from the Builder floor plan. Buyer to verify measurements. Square footage is from Orange County Appraiser records ** Refrigerator ice maker is not working **

5522 New Independence Parkway, Winter Garden
11390 Bourbon Rose Circle, Winter Garden
$860,494
4 Beds ⋅ 3 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
What's Special: No Rear Neighbors | Larger Lot | Convenient 1st Floor Living. New Construction - Ready Now! Welcome to the Bainbridge at 11390 Bourbon Rose Circle in Esplanade at McKinnon Groves! This spacious single-story home offers four bedrooms, three bathrooms, a versatile flex room, and a three-car garage. The open-concept layout features a bright great room that flows into the dining area and gourmet kitchen with walk-in pantry, creating the perfect space for gathering and entertaining. The private primary suite is tucked away at the rear of the home, while three secondary bedrooms provide comfort and flexibility. Enjoy outdoor living on the covered lanai. Additional Highlights Include: tray ceiling package, whole house 8' interior doors, outdoor kitchen rough-in, and prewired for future pool and spa. MLS#O6451559 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.

11390 Bourbon Rose Circle, Winter Garden
17055 Seville Orange Road, Winter Garden
$649,000
3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
A DREAM IS A WISH YOUR HEART MAKES! LIVE JUST 3 MINUTES FROM THE GATES OF DISNEY! Discover an exceptional opportunity to experience MAGICAL FLORIDA LIVING in the highly desirable NORTHLAKE AT OVATION community of HORIZON WEST, where sophisticated design, modern convenience, and an extraordinary location come together just moments from the MAGIC OF WALT DISNEY WORLD. This beautifully appointed 2024 BUILT ASHTON WOODS RESIDENCE offers the elegance of LUXURY LIVING minutes from Disney gates without the MULTI MILLION DOLLAR PRICE TAG. Crafted by ASHTON WOODS, recognized as BUILDER magazine’s 2023 BUILDER OF THE YEAR, this thoughtfully designed residence showcases an impressive combination of architectural sophistication, quality craftsmanship, and carefully curated upgrades. An inviting OPEN CONCEPT FLOOR PLAN welcomes abundant NATURAL LIGHT, creating an atmosphere of understated elegance throughout. At the heart of the home, a beautifully appointed GOURMET KITCHEN seamlessly connects the principal living and entertaining spaces, offering an ideal setting for intimate gatherings and effortless everyday living. GENEROUSLY PROPORTIONED BEDROOMS, a VERSATILE LOFT, DESIGNER FINISHES, ENHANCED LIGHTING, and a thoughtfully equipped laundry room with UTILITY SINK further elevate the experience. Outdoors, an EXTENDED LANAI overlooks the PRIVATE BACKYARD, providing an inviting retreat for enjoying Florida’s year round lifestyle and the opportunity to watch DISNEY FIREWORKS LIGHT UP THE EVENING SKY. An EV READY TWO CAR GARAGE adds another layer of modern convenience. Beyond the residence, NORTHLAKE AT OVATION presents an exceptional RESORT INSPIRED LIFESTYLE, complete with a COMMUNITY POOL, CLUBHOUSE, DOG PARK, PLAYGROUND, WALKING TRAILS, and beautifully maintained GREEN SPACES. This thoughtfully planned neighborhood offers a peaceful residential setting while placing some of Central Florida’s most sought after destinations within remarkably easy reach. LOCATION IS THE ULTIMATE LUXURY, and few addresses offer such an extraordinary connection to the WALT DISNEY WORLD RESORT. Enjoy convenient access to the WESTERN ENTRANCE OF DISNEY, FLAMINGO CROSSINGS TOWN CENTER, HAMLIN, SR 429, highly regarded schools, upscale shopping, dining, and entertainment. Whether seeking a refined primary residence, an elegant Florida retreat, or the convenience of living near one of the world’s most celebrated destinations, this location offers an enviable balance of TRANQUILITY, ACCESSIBILITY, and LIFESTYLE. A rare opportunity to own a MOVE IN READY, BEAUTIFULLY UPGRADED ASHTON WOODS HOME in one of HORIZON WEST’S most desirable communities, where MODERN ELEGANCE meets the extraordinary privilege of having DISNEY MAGIC just moments away. LIVE WHERE OTHERS DREAM OF VACATIONING. YOUR HAPPILY EVER AFTER BEGINS HERE.

17055 Seville Orange Road, Winter Garden
14743 Field Daisy Drive, Winter Garden
$654,718
3 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Loft | Balcony. New Construction - December Completion! Welcome to the Newberry at 14743 Field Daisy Drive in Harvest at Ovation! Welcome to this stunning two-story home. Thoughtfully designed for both comfort and flexibility, this spacious floor plan features three bedrooms, four-and-a-half bathrooms, a versatile loft, an expansive game room, and a two-car garage. The open-concept main living area seamlessly connects the great room, designer kitchen, casual dining space, and lanai, creating an inviting setting for everyday living and entertaining. Upstairs, the private primary suite offers a relaxing retreat with a spacious bath and generous walk-in closet, while the loft provides additional space for work, play, or gathering. A secondary bedroom and bath on the upper level, plus an oversized game room with its own bathroom on the top floor, provide privacy and flexibility for guests or multigenerational living. 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: 8' interior doors, tray ceiling package, wet bar at game room and shower in place of tub at bath 2. Photos are for representative purposes only. MLS#O6450084

14743 Field Daisy Drive, Winter Garden
12934 Harvest Rain Avenue, Winter Garden
$750,000
3 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Amenities | 3 Full Baths. New Construction - February Completion! Welcome to the Ozark at 12934 Harvest Rain Avenue in Harvest at Ovation! This thoughtfully designed one-story home offers three bedrooms, three and a half bathrooms, and a private study off the foyer. The open-concept layout centers around a spacious gathering room that flows seamlessly into the dining area and gourmet kitchen with a walk-in pantry, creating the perfect space for everyday living and entertaining. The private primary suite features a spacious bathroom and large walk-in closet, while the secondary bedrooms provide comfort and flexibility for guests or hobbies. Enjoy outdoor living on the covered extended lanai and the convenience of a two-car garage with tandem storage space. 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: pocket sliding glass door at great room, tray ceiling package, whole house 8' interior doors, quartz countertops, whole house blinds, and outdoor kitchen rough-in. Virtually staged photos are for representative purposes only. MLS#O6450081

12934 Harvest Rain Avenue, Winter Garden
8067 Glenlloyd Avenue, Winter Garden
$394,000
3 Beds ⋅ 3 Baths ⋅ Hawksmoor-Ph 1 SubDv. ⋅ 34787 Zip Code
SELLER CREDIT OF $5,000 OFFERED! Welcome home to this better-than-new townhome in Horizon West! Why pursue new construction when you can have UPDATES AND UPGRADES GALORE including a new primary bathroom barn door and shower, faucets and commodes in all bathrooms, carpet padding, soft-close cabinets, ceiling fans, hue lighting in the living room, and fresh touch-up paint inside and out. This townhome requires that you sacrifice nothing! The curb appeal is waiting to welcome you from the moment you pull up to the house. A massive covered front porch is ready for your morning coffee to be sipped and/or your evening beverage of choice. Step inside and forget that you are in a townhome as you take in the HUGE kitchen in the middle of the open concept downstairs living. Whether prepping meals, socializing, or landing an airplane, this kitchen island was made for enjoyment. This kitchen features stone countertops, loads of cabinetry, and stainless steel appliances all with a popular and tasteful color palette. A dining space on one side of the kitchen and a living room on the other, both lined with windows for natural lighting, make this space one to write home about. Head upstairs and find the primary suite on one side and the secondary bedrooms on the other. The primary bathroom has a brand new shower, dual vanity, and private water closet. You can even SEE DISNEY FIREWORKS from the bedroom and bathroom! The 2 remaining bedrooms share a bathroom that includes a shower/bathtub combination. Step out back to your private brick-paved courtyard ready for your outdoor enjoyment. The home and the 2-car garage are connected by an overhang across this courtyard for convenience and weather protection. This community is situated in the heart of Horizon West between Hamlin and Waterleigh for ample shopping and dining options, is super close to Disney, and right off of Highway 429 to bring you to all your favorite Central Florida destinations. Inquire today to make this gem your own!

8067 Glenlloyd Avenue, Winter Garden
14747 Field Daisy Drive, Winter Garden
$573,147
3 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Amenities | Gas Range | 1st Floor Guest Suite. New Construction - December Completion! Welcome to the Newberry at 14747 Field Daisy Drive in Harvest at Ovation! This thoughtfully designed two-story home offers three bedrooms, three-and-a-half baths, and inviting spaces that blend comfort with everyday convenience. The bright kitchen with a spacious island opens to the casual dining area and great room, creating a warm and welcoming setting for gathering with family and friends. A first-floor secondary bedroom with an ensuite full bath is perfect for guests, while upstairs, the private primary suite provides a peaceful retreat with a generous walk-in closet and well-appointed bath. A versatile loft adds flexible living space, and the covered lanai is ideal for relaxing or enjoying time outdoors. Complete with a two-car garage, this home is as functional as it is charming. 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: Shower in place of tub at secondary bath, 8' interior doors, pre-plumb for future laundry tub, LVP flooring throughout, and whole house blinds. Photos are for representative purposes only. MLS#O6449322

14747 Field Daisy Drive, Winter Garden
14779 Field Daisy Drive, Winter Garden
$625,000
4 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Game Room | Close to Amenities | 1st Floor Guest Suite. New Construction - November Completion! Welcome to the Newberry at 14779 Field Daisy Drive in Harvest at Ovation! Step into this thoughtfully designed four-bedroom home featuring flexible living spaces and inviting areas to gather. The open-concept main level showcases a bright kitchen with a large island overlooking the casual dining area and spacious great room, creating the perfect setting for everyday living and entertaining. A secondary bedroom and full bath on the main floor provide flexibility for guests, a home office, or multi-generational living. Upstairs, the private primary suite provides a relaxing retreat, while two additional bedrooms, a versatile game room, and convenient laundry room provide plenty of space to fit your lifestyle. Enjoy seamless indoor-outdoor living with a covered lanai that extends your living space year-round. 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: 8' interior doors, wet bar at game room, shower in place of tub at bath 2, luxury vinyl plank flooring and quartz countertops. Photos are for representative purposes only. MLS#O6449273

14779 Field Daisy Drive, Winter Garden
16735 Silver Brook Way, Winter Garden
$531,190
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 situated on a corner homesite 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.

16735 Silver Brook Way, Winter Garden
16651 Evermore Alley, Winter Garden
$524,090
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 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.

16651 Evermore Alley, Winter Garden
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