Winter Garden Homes with Two Story Style

16730 Rusty Anchor Road, Winter Garden

3 Beds ⋅ 4 Baths ⋅ O6436917 MLS ⋅ Taylor Morrison BLDG.

Under Construction. What's Special: Flat Lot | 3 Full Baths | Bonus Room. New Construction – November Completion! Welcome to the Ashwood at 16050 Honey Harvest Street in Harvest at Ovation! This warm and inviting two-story home blends comfort, flexibility, and effortless everyday living. A charming front porch opens to a bright foyer with a private study, while the heart of the home features a spacious great room that flows into the beautifully designed kitchen with a large island, walk-in pantry, and inviting lanai for indoor-outdoor gatherings. Upstairs, the serene primary suite offers a relaxing retreat with a spa-inspired bath and generous walk-in closet, while two secondary bedrooms share a full bath. The top-floor game room with its own bath provides the perfect space for entertaining, hobbies, or cozy evenings at home. Thoughtfully designed and filled with natural flow, this home is made for connection and comfort. 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: Wet bar at game room, game room with full bath above garage, covered extended lanai, pre-plumb for future laundry tub, and whole house blinds. Photos are for representative purposes only. MLS#O6436917

16050 Honey Harvest Street, Winter Garden

$787,000

5 Beds ⋅ 4 Baths ⋅ O6436008 MLS

Virtually Staged. Built in 2020, this beautifully designed five-bedroom, four-bathroom home offers 2,840 square feet of thoughtfully planned living space in the sought-after Waterleigh community. The private outdoor retreat features a heated saltwater pool, screened enclosure, and covered lanai, perfect for year-round relaxation and entertaining. Inside, the open-concept main level showcases quartz countertops, upgraded cabinetry, and a seamless flow from the kitchen to the dining and gathering areas, with sliding glass doors opening to the pool and lanai. A first-floor bedroom with an adjacent full bathroom provides exceptional flexibility for guests, multigenerational living, or a private home office. Upstairs, four additional bedrooms and well-appointed bathrooms offer plenty of space and privacy. Built in 2020, the home also offers the advantage of newer roofing, HVAC, and major systems. Additional features include a two-car garage and access to Waterleigh’s impressive amenities, including resort-style community pools, clubhouses, fitness centers, tennis courts, a dog park, multiple parks, and stocked fishing ponds. Homes offering a private heated saltwater pool and first-floor guest accommodations are a rare find. Schedule your private showing today.

16771 Oakboro Street Street, Winter Garden

$600,000

3 Beds ⋅ 3 Baths ⋅ O6436549 MLS

Welcome to a home that feels as inviting as it is impressive, tucked into the quaint gated community of Amberleigh, just minutes from the charm of historic Downtown Winter Garden and the West Orange Trail. With more than 2,600 square feet of thoughtfully designed living space, this home blends warmth, character, and room to gather. Step inside and the story begins with soaring ceilings that draw your eye toward the upstairs landing, while graceful architectural details, rounded corners, decorative niches, and beautifully appointed engineered hardwood floors bring warmth and character throughout the home. The generous family room creates a natural heart of the home, while a dedicated downstairs office offers a comfortable space for working from home, reading, or tackling the day's to-do list. At the center of it all is a kitchen designed for both everyday moments and memorable gatherings. Granite countertops pair beautifully with abundant cherry cabinetry and a custom cherry wood bar top, while generous prep space, upgraded appliances, double ovens with convection, a built-in desk, and an oversized pantry make the space as functional as it is welcoming. The first-floor owner's suite offers a peaceful retreat with a tray ceiling, dual closets, dual marble vanities, a dual-head shower, and a relaxing Roman tub. Upstairs, the home continues to unfold with spacious secondary bedrooms and a generous bonus room, creating a wonderfully flexible second living space for movie nights, games, hobbies, or simply relaxing at the end of the day. Thoughtful details continue throughout with marble vanities in the secondary baths, ceramic tile in the foyer, laundry room, and secondary bath, convenient under-stair storage, and a four-zone irrigation system. Behind the scenes, meaningful updates bring added comfort and efficiency to everyday living. New HVAC systems provide refreshed climate control, with the system serving the upstairs featuring advanced air filtration. A new energy-efficient hot water heater and whole-home water softener add to the home's thoughtful improvements, while energy-efficient insulated windows along the rear of the home help enhance year-round comfort. Move-in ready and wonderfully located, this is a home made for comfortable mornings, lively gatherings, movie nights upstairs, and evenings spent enjoying everything Winter Garden has to offer. Downtown dining, local shops, community events, and miles of recreation along the West Orange Trail are all just minutes away. A charming gated setting, generous living spaces, thoughtful updates, and the Winter Garden lifestyle come together in a home ready for its next chapter.

393 Lake Amberleigh Drive, Winter Garden

$925,000

5 Beds ⋅ 3 Baths ⋅ O6436619 MLS

5 bedrooms. 3 full baths. Nearly 3,740 SF. 3-car garage. Private screened pool. Gated community. Newer roof and A/C. Minutes from Winter Garden Village, AdventHealth, SR-429, the Florida Turnpike, Historic Downtown Winter Garden, and convenient to Walt Disney World. This is the combination buyers spend months trying to find. Set behind the gates of Wintermere Pointe, 2491 Prairie View Drive brings together a flexible five-bedroom floor plan, multiple living and entertaining spaces, private outdoor living, and a connected Winter Garden location with shopping, dining, healthcare, major roadways, and entertainment within easy reach. Step inside and the scale is immediately apparent. Soaring ceilings rise above formal living and dining rooms, leading to a spacious family room anchored by a striking dual staircase. Large sliding glass doors frame the greenery and blue waters of the pool beyond. At the center of the home, the updated gourmet-style kitchen offers stainless steel appliances, abundant cabinetry and counter space, a prep island, casual seating, and views toward the pool and backyard — creating a natural flow between cooking, gathering, and outdoor entertaining. A first-floor bedroom and nearby full pool bath provide valuable flexibility for guests, extended family, multigenerational living, or a private office. Upstairs, two separate loft areas provide space for a media room, game room, second living area, or quiet retreat. The larger opens directly onto an expansive second-story balcony overlooking the pool. An oversized bonus bedroom above the garage, incorporated as a builder upgrade, joins two additional bedrooms and a shared full bath. The naturally bright primary suite features dual walk-in closets and an ensuite with separate vanities, soaking tub, and walk-in shower. Outside, the Florida lifestyle takes over. A private screened pool and covered lanai extend the living space outdoors, with additional yard beyond the enclosure and the second-story balcony above. A generous driveway and three-car garage provide valuable parking and storage, while a newer roof and A/C add two significant improvements already in place. Wintermere Pointe offers the privacy of an established gated community with Winter Garden Village, AdventHealth, shopping, dining, and everyday conveniences nearby. Quick access to SR-429 and the Florida Turnpike keeps Central Florida connected, with Historic Downtown Winter Garden and Walt Disney World conveniently accessible. What makes this home compelling isn't any one feature. It's how rarely they come together. Nearly 3,740 SF. Five bedrooms. First-floor guest space. Two lofts. Oversized bonus bedroom. Expansive balcony. Private screened pool and lanai. Three-car garage. Newer roof and A/C. Gated community. Prime Winter Garden location. You don't have to choose between space and location, indoor and outdoor living, or rooms for everyone and places to come together. It's already here. If this is the combination you've been waiting to find, 2491 Prairie View Drive deserves to be seen.

2491 Prairie View Drive, Winter Garden

$475,000

5 Beds ⋅ 3 Baths ⋅ O6433640 MLS

Welcome to this beautifully renovated 5-bedroom, 2.5-bathroom block-and-stucco home with a peaceful pond view. Extensively updated from top to bottom, this home offers the look and feel of a brand-new home without the wait for new construction. Inside, the popcorn ceilings have been removed and replaced with fresh, modern texture throughout, creating a clean, contemporary feel. The home also features fresh interior and exterior paint, new luxury vinyl plank flooring throughout, new baseboards, and all-new light fixtures, ceiling fans, switches, hinges, and door hardware. The spacious floor plan offers exceptional flexibility, with a convenient bedroom and bathroom located downstairs. The additional bedrooms provide plenty of room for family, guests, an office, or other living needs. The beautifully redesigned kitchen is a true centerpiece, featuring new 42-inch cabinets with light rail molding, full quartz countertops and backsplash, and a stunning waterfall edge. New stainless steel appliances include a slide-in range and counter-depth refrigerator, creating a stylish and functional kitchen perfect for everyday living and entertaining. The bathrooms have been completely updated with custom tile work and modern finishes. The primary suite features a beautifully renovated bathroom with double sinks and the added luxury of two walk-in closets. Major systems provide added peace of mind, with a 2020 roof and a 2021 AC system that has been cleaned and serviced. The home also features durable block-and-stucco construction. For added peace of mind, a four-point inspection, energy report, and wind mitigation report are available for review and may help with insurance discounts. Enjoy the peaceful pond view while being ideally located just minutes from downtown Winter Garden, with convenient access to the 408 and Florida's Turnpike. Shopping, dining, entertainment, major roadways, and Orlando's many attractions are all within easy reach. With extensive renovations, modern finishes, flexible living space, and a tranquil setting, this move-in-ready home is an exceptional opportunity.

427 Regal Downs Circle, Winter Garden

$565,000

3 Beds ⋅ 3 Baths ⋅ S5156149 MLS

Welcome to this beautifully maintained home in the desirable Hawksmoor community of Winter Garden! Built in 2019, this bright and inviting residence offers modern style, thoughtful design, and comfortable living in one of the area’s sought-after communities. From the moment you arrive, the charming curb appeal and beautifully landscaped front yard create a warm welcome. Inside, you’ll find an open and airy layout filled with natural light, recessed lighting, and stylish finishes throughout. The spacious living area features a modern fireplace and large windows with elegant window treatments, creating the perfect space to relax or entertain. A thoughtfully enclosed flex space features beautiful sliding glass doors, creating a private and beautifully finished home office that is perfect for working from home, studying, or a variety of lifestyle needs. The contemporary kitchen offers modern cabinetry, stainless steel appliances, a generous island with seating, and plenty of workspace, flowing seamlessly into the dining and living areas. Sliding glass doors extend the living space to a screened-in lanai, providing a wonderful indoor-outdoor setting for morning coffee, dining, or entertaining while enjoying the Florida lifestyle. The home's neutral finishes, beautiful tile flooring, and well-maintained interiors make it truly move-inready. Located in Hawksmoore, this home offers the perfect combination of modern comfort, community living, and the highly desirable Winter Garden lifestyle. Don't miss the opportunity to make this beautiful home your own!

16273 Taliesin Street, Winter Garden

$475,000

4 Beds ⋅ 3 Baths ⋅ O6436292 MLS ⋅ Mezzano BLDG.

Welcome to 6982 Twilight Bay Drive, a beautifully maintained two-story townhome located in the Mezzano community of Winter Garden. Completed in late 2023, this newer home offers approximately 1,860 square feet of thoughtfully designed living space featuring 4 bedrooms, 2.5 bathrooms, and a spacious 2-car garage. Step inside to a bright and inviting open-concept floor plan filled with natural light and complemented by stylish accent walls and modern finishes throughout. The kitchen flows seamlessly into the main living and dining areas, creating a functional layout for everyday living and entertaining. A first-floor bedroom adds flexibility for use as a guest room, home office, fitness space, or additional living area. Upstairs, the spacious primary suite provides a comfortable retreat alongside two additional bedrooms and well-appointed living spaces. Smart switches throughout much of the home add convenience, while the rear-entry 2-car garage provides additional storage and is equipped with a 240V outlet for electric vehicle charging. The private outdoor patio offers additional space to enjoy the Florida lifestyle. Residents of Mezzano enjoy access to community amenities including a resort-style pool, cabana, recreation areas, playground, and sidewalks. Location is a standout feature of this Winter Garden property. Enjoy convenient access to the Horizon West area, with Hamlin Town Center approximately 10 minutes away for shopping, dining, entertainment, and everyday conveniences. Walt Disney World Resort is approximately 15–20 minutes away, while Disney Springs, Universal Orlando Resort, SeaWorld Orlando, and ICON Park are all within approximately 20–35 minutes, depending on destination, route, and traffic. Historic Downtown Winter Garden is approximately 20–25 minutes away, offering access to Plant Street, local restaurants, shopping, entertainment, community events, and the West Orange Trail. Outdoor recreation is also nearby, including Tibet-Butler Nature Preserve, Orange County National Golf Center, local parks, trails, lakes, and numerous golf and recreation options throughout Winter Garden and Horizon West. Convenient access to SR-429, Florida's Turnpike, and I-4 makes traveling throughout Central Florida easily accessible. Orlando International Airport is approximately 35–40 minutes away, depending on traffic and route. Looking for a Florida beach day? Central Florida's location provides access to both coasts. Cocoa Beach and the Space Coast are approximately 85–90 minutes away, providing access to the Atlantic Ocean, Cape Canaveral, and nearby Space Coast attractions. Gulf Coast destinations such as Clearwater Beach are approximately 1 hour and 55 minutes to 2 hours away, depending on traffic and route. With newer construction, a flexible four-bedroom floor plan, smart-home features, EV charging capability, community amenities, and convenient access to Central Florida's theme parks, shopping, dining, recreation, airports, beaches, and major roadways, 6982 Twilight Bay Drive offers an excellent opportunity to enjoy the Winter Garden and Horizon West area.

6982 Twilight Bay Drive, Winter Garden

$558,000

3 Beds ⋅ 3 Baths ⋅ O6435240 MLS

Welcome to this beautifully designed home in the heart of Winter Garden’s highly sought-after Horizons West area, offering nearly 2,500 square feet of thoughtfully designed living space with a fenced backyard and an upgraded elevation featuring a charming front porch. Located just minutes from Historic Downtown Winter Garden, Hamlin Town Center, shopping, dining, entertainment, and Disney, this home offers an exceptional combination of convenience and lifestyle. You may even enjoy views of Disney fireworks from the home! The spacious open-concept floor plan is designed for comfortable everyday living and entertaining. The main level features a large great room filled with natural light, along with a versatile 3 Bedrooms PLUS **DOWNSTAIRS OFFICE/FLEX room with double-door entry**, perfect for a home office, study, or additional living space. The gourmet kitchen features espresso 42-inch cabinetry, granite countertops, a large center island, and stainless-steel appliances, opening directly to the great room. Tile flooring throughout the main living areas adds both style and easy maintenance. Large sliding glass doors provide seamless access to the **covered lanai and FULLY FENCED backyard**, bringing plenty of Florida sunshine indoors. Upstairs, a spacious loft provides additional flexible living space. The generous primary suite offers a large walk-in closet and a well-appointed ensuite bathroom with an oversized walk-in shower and beautiful tile accents. Two additional bedrooms and a full bathroom complete the second floor. Energy-efficient, spacious, and exceptionally well located, this home is zoned for the **highly desirable Horizon West school district** and offers easy access to Disney, State Road 429, shopping, restaurants, and entertainment. Best of all, the **HOA INCLUDES lawn care**, making this home even easier to maintain. A rare opportunity to enjoy space, convenience, and the Horizon West lifestyle at an exceptional value—this home is a must-see!

14373 Breda Center Loop, Winter Garden

$614,999

4 Beds ⋅ 4 Baths ⋅ O6430058 MLS

**** STUNNING 4 BEDROOM + LOFT | 3.5 BATH HOME IN HARVEST AT OVATION | MODERN LIVING IN WINTER GARDEN **** Welcome to this beautifully maintained 4-bedroom + loft, 3.5-bath single-family home located in the highly sought-after Harvest at Ovation community in Winter Garden. Thoughtfully designed with an open-concept floor plan, stylish finishes, and generous living spaces, this exceptional residence offers the perfect combination of elegance, comfort, and everyday functionality. Step inside to an inviting foyer that leads into a bright and expansive living and dining area, seamlessly connected to the gourmet kitchen—creating the ideal setting for entertaining, family gatherings, or simply enjoying day-to-day living. The versatile flex space on the main level can easily be used as a home office, playroom, fitness room, or additional sitting area to suit your needs. Upstairs, you'll find a spacious loft that serves as the perfect second living room, media room, or workspace. The luxurious primary suite provides a private retreat featuring a spa-inspired ensuite bathroom with dual vanities, an oversized walk-in shower, and generous closet space. Three additional bedrooms and well-appointed bathrooms offer flexibility for family, guests, or multigenerational living. Located in one of Winter Garden's most desirable communities, Harvest at Ovation offers outstanding amenities and an unbeatable location just minutes from SR-429, Walt Disney World, Hamlin Town Center, top-rated schools, shopping, dining, and countless entertainment options. Meticulously cared for and move-in ready, this home provides the opportunity to enjoy the benefits of newer construction without the wait. Whether you're searching for your primary residence or your next Central Florida home, this property offers the perfect balance of location, space, and modern design. Schedule your private showing today and experience everything this exceptional Winter Garden home has to offer!

16319 Honey Harvest Street, Winter Garden

$834,000

5 Beds ⋅ 5 Baths ⋅ O6436505 MLS

Luxury new home 3501 SFT with oversized yard near Walt Disney World theme parks. Frost plan by RockWell Homes, a luxurious new home designed to meet all your needs. This stunning home features 5 bedrooms, 4.5 bathrooms, and a spacious layout that includes both a primary suite and a guest bedroom on the first floor, making it ideal for multi-generational living or hosting visitors. The Frost plan also boasts an oversized covered front patio, 12-foot sliding glass back door, 8-foot front door, and a covered backyard lani for seamless indoor-outdoor living. Step into the heart of the home, where the chef-inspired kitchen features a large eat-in island, stainless steel appliances, including a cooktop, oven, microwave, and dishwasher, and an undermount sink with a Delta faucet. The kitchen is further enhanced with a ceramic tile backsplash, upgraded 42-inch cabinets, abundant solid surface countertop space, and a huge walk-in pantry, offering both style and practicality for meal preparation and storage. The upgraded flooring and lighting package throughout the home complete the modern, elegant aesthetic. The luxurious primary suite is located on the first floor for ultimate convenience and privacy. It includes a dual-sink vanity with solid surface countertops and Delta faucets, a ceramic tile shower with a glass enclosure, ceramic tile flooring, and a lighting package. A spacious walk-in closet and towel bars add to the functionality and style of this retreat. Also located on the first floor, the secondary suite offers a full bath with ceramic tile flooring, a ceramic tile tub/shower surround, Delta faucets, a lighting package, and towel bars, ensuring comfort and convenience for guests or family members. Upstairs, you’ll find three additional secondary bedrooms, each with generous closet space and access to two additional bathrooms, which feature ceramic tile flooring, Delta faucets, lighting packages, and towel bars. The Frost plan also includes a gameroom, perfect for family entertainment or as a versatile space for play, work, or relaxation. The home is designed with energy-efficient block construction and dual-pane energy-efficient windows, keeping your energy costs down while ensuring comfort throughout the year. Additional features of this new home include a full landscaping package, a full sprinkler system, full gutters, a garage door opener, covered back yard lanai, upgraded flooring throughout, and a 10-year structural new home warranty for added peace of mind. With its spacious layout, luxurious finishes, and modern amenities, the Frost plan by RockWell Homes is the perfect choice for those seeking both elegance and functionality in their next home.

17428 Honeybell Tangelo Court, Winter Garden

$652,990

4 Beds ⋅ 4 Baths ⋅ O6436494 MLS

Under Construction. .

12349 Silk Mimosa Alley, Winter Garden

Winter Garden Homes with Two Story Style

Newest Winter Garden Homes with Two Story Style

Adair Realty, Inc.

Search

Resources

About