Winter Garden Homes with Two Story Property Description

Winter Garden Homes with Two Story Property Description

Welcome to Winter Garden, a charming city located in the sunny state of Florida. Known for its small-town feel and friendly community, Winter Garden offers a perfect blend of suburban tranquility and urban convenience.

If you are looking for homes with a two-story property description, Winter Garden has plenty to offer. These homes are perfect for families looking for a bit of extra space or individuals who appreciate the separation of living and sleeping areas. With beautiful architecture and modern amenities, two-story homes in Winter Garden provide both comfort and style.

Imagine coming home to a spacious living room, a gourmet kitchen, and cozy bedrooms upstairs where you can unwind and relax. Whether you are hosting a gathering or enjoying a quiet evening in, a two-story home in Winter Garden offers the perfect setting for every occasion.

In addition to the lovely homes, Winter Garden boasts a vibrant downtown area with boutique shops, delicious restaurants, and community events. Residents can enjoy the West Orange Trail for outdoor activities or explore the historic downtown district for a taste of the city's rich heritage.

With its picturesque surroundings and welcoming atmosphere, Winter Garden is the ideal place to call home. Discover the beauty and charm of this city and find your perfect two-story home in Winter Garden, Florida.

Newest Winter Garden Homes with Two Story Property Description

6123 Flowering Cherry Bend, Winter Garden
$844,073
6 Beds ⋅ 5 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
Under Construction. Discover the Anna Maria with Bonus in Avalon Woods! This two-story home offers 6 bedrooms, 4 full bathrooms, 1 half bathroom, and approximately 3,412 square feet of living space. The main level features a spacious great room, dining area, kitchen, and a private primary suite with a walk-in closet and bath. Upstairs, enjoy a versatile bonus room and additional bedrooms and bathrooms. A two-car garage adds everyday convenience. Community amenities include a park, playground, and trails. Conveniently located near shopping, dining, and major roadways in Winter Garden. Pricing, features, and availability are subject to change; confirm details with the builder.

6123 Flowering Cherry Bend, Winter Garden
12542 Encore At Ovation Way, Winter Garden
$669,000
4 Beds ⋅ 4 Baths ⋅ Encore/Ovation Ph 3 SubDv. ⋅ 34787 Zip Code
Fall in love with this 4-bedroom, 3.5-bath, 2,781 square foot home with 2-car ally-load garage. This versatile plan will wow you the minute you enter, with its impressive 2-story foyer. A bedroom with its own full bath is located up front, creating the perfect spot for guest, in-laws, or perhaps a home office. The chef of the home won’t feel ostracized in this kitchen; the family room, kitchen, and dining room are all open to each other, creating a perfect spot for family hangouts or weekend entertaining, keeping everyone in the mix. Enjoy a covered lanai located on the side of the home through the oversized sliding glass door. Head upstairs to find three more bedrooms and a loft. The loft is the perfect space for movie night, game day, or just a second hangout. It separates the owner’s suite in the back of the home from the secondary bedrooms, giving everyone the privacy, they deserve. The owner’s suite features two very impressive sized walk-in closets and a bathroom to match. You’ll be happy this Horizon West new home is built with features that meet the Energy Star® 3.1 home building requirements, saving you on the cost of ownership. It’s also backed by M/I Homes' industry leading 10-Year Transferable Warranty. Contact us today before it’s gone!

12542 Encore At Ovation Way, Winter Garden
665 Canopy Estates Drive, Winter Garden
$1,499,900
5 Beds ⋅ 5 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code
Virtually Staged. EXCEPTIONAL LUXURY IN THE HEART OF WINTER GARDEN! Welcome to this stunning 5-bedroom, 4.5-bathroom pool home nestled within Canopy Oaks, an exclusive, Parade of Homes award-winning gated community featuring just 49 residences. This beautifully upgraded Lockhart II model delivers an exceptional blend of elegance, comfort, and sophistication, featuring TWO luxurious primary suites, one on each floor, a 3-car garage, and private front and rear balconies. Step through the magnificent arched double doors into a breathtaking two-story foyer, where timeless architectural details and modern finishes set the tone. The thoughtfully designed interior showcases a versatile office or flex space, an exquisite wine cellar with authentic Chicago brick flooring, and a gourmet kitchen featuring a 5-burner natural gas cooktop and oversized island. A beautiful wooden staircase with custom forged-iron railings leads upstairs to generously sized bedrooms, a spacious primary suite with an impressive walk-in closet, and a dedicated home theater complete with a movie projector. RECENT UPGRADES includes 2025 A/C system, contemporary light fixtures, updated countertops, fresh interior paint, new downstairs flooring, custom closets, and a beautifully remodeled backyard. Step outside into your private retreat, featuring a sparkling pool and an inviting setting for entertaining or unwinding. LOCATION IS EVERYTHING! Just minutes from Winter Garden Village and Historic Downtown Winter Garden, enjoy convenient access to premier shopping, exceptional dining, and entertainment. With easy connections to Florida’s Turnpike, SR 429, SR 408, and Highway 50, the best of Central Florida is within easy reach. Luxury, exclusivity, and an unbeatable location come together in one extraordinary home. Schedule your private showing today!

665 Canopy Estates Drive, Winter Garden
14347 Braemar Street, Winter Garden
$493,000
4 Beds ⋅ 3 Baths ⋅ Highland Ridge SubDv. ⋅ 34787 Zip Code
Built in 2024 by Meritage Homes, this pristine 4-bedroom, 2.5-bathroom bungalow in Horizon West’s Highland Ridge delivers energy-efficient modern living at its finest. The open-concept first floor boasts high ceilings, durable tile flooring, and a chef’s kitchen equipped with a large prep island, solid-surface counters, 42” cabinetry, and stainless steel appliances. All 4 bedrooms and the laundry room are conveniently located upstairs, headlined by a primary retreat with an oversized walk-in closet and dual-sink ensuite bath. Built with advanced spray-foam insulation, high-performance windows, and smart features for peak comfort and utility savings. Enjoy community pool access, cabana, and tot lot, with immediate proximity to SR-429, Flamingo Crossings shopping and dining, top-rated schools, and Walt Disney World.

14347 Braemar Street, Winter Garden
10067 Austrina Oak Loop, Winter Garden
$1,150,000
6 Beds ⋅ 5 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code
Welcome home this beautifully renovated 6-bedroom, 5-bathroom home offering 4,305 sq. ft. of stylish living in a desirable Winter Garden community. Features include elegant first-floor porcelain tile, an updated kitchen with quartz countertops, a smart cooktop, and decorative glass cabinetry. The spacious primary suite boasts a custom-built walk-in closet. Enjoy Florida living in the outdoor oasis featuring a gazebo and built-in fire pit seating area. A three-car split garage provides ample parking and storage. Residents enjoy two community pools and a playground. Freshly updated and move-in ready, this exceptional home offers comfort, style, and space for the whole family!

10067 Austrina Oak Loop, Winter Garden
8877 Lakeshore Pointe Drive, Winter Garden
$650,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to this stunning, completely remodeled home in beautiful Winter Garden! Offering 4 spacious bedrooms, 3.5 luxurious bathrooms, and a separate guest house. This exceptional property combines elegance, comfort, and versatility. The home features a gorgeous interior courtyard, creating a beautiful private setting perfect for relaxing or entertaining. Inside, you’ll find soaring ceilings throughout, an elegant and inviting living space, and a chef-inspired kitchen equipped with state-of-the-art appliances and exquisite finishes. The spacious bedrooms include comfort and privacy, while the luxurious primary suite features a spa-inspired bathroom with a beautiful soaking tub, an elegant walk-in shower, and generous closet space. Every detail has been thoughtfully designed to create an elegant yet welcoming atmosphere. With its complete renovation, stunning architectural features, private courtyard, and separate guest residence, this extraordinary Winter Garden home offers a truly special living experience.

8877 Lakeshore Pointe Drive, Winter Garden
15633 Panther Lake Drive, Winter Garden
$2,395,000
4 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
**Organic Modern Design. Intelligently Connected. Effortlessly Luxurious.** Discover extraordinary lakefront living in Winter Garden's Lakeshore Preserve community. Reimagined with nearly $1 million in renovations, this stunning residence blends sophisticated design, intelligent technology, and five-star resort-inspired living. Featured in *The Local Magazine's 2026 Home Issue*, the home showcases organic modern design with European and Mediterranean influences. Limewash walls, graceful archways, wide-plank flooring, custom millwork, and designer lighting create a warm, sophisticated atmosphere. A sculptural staircase with sweeping curved walls and a dramatic cascading chandelier makes an unforgettable statement. The beautifully appointed kitchen features custom cabinetry, premium JennAir appliances, a double-stacked quartz island, quartz backsplash, and beverage refrigeration. A walk-in pantry and drop zone add functionality. The primary suite offers a spa-inspired bath with a freestanding soaking tub, programmable shower, and custom California Closets. Additional highlights include a designer laundry room, upstairs entertainment loft, and equipped home gym with sauna. What truly sets this home apart is its seamless integration of technology. Control4 automation connects customizable Philips Hue lighting, Sonos audio, motorized shades, smart thermostats, security, and other features, making everyday luxury feel effortless. Outdoors, an infinity-edge pool with cascading waterfall overlooks Panther Lake. A two-level pool deck, covered entertaining areas, outdoor fireplace, integrated speakers, and motorized lanai screens create a private resort experience. Architectural lighting and a mosquito misting system add comfort and ambiance. Additional features include a whole-house generator, climate-controlled garages, EV charging, extensive security, and a professional smart-home technology transfer service for the new owner. Lakeshore Preserve offers included lawn care and a convenient location near Walt Disney World and SR 429

15633 Panther Lake Drive, Winter Garden
16549 Parable Way, Winter Garden
$545,000
4 Beds ⋅ 4 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code
Virtually Staged. 2023 build new house! Highly desirable Storey Grove community! NO CDD.Low HOA fee! Beautifully maintained 4-bedroom, 3.5-bath home in the highly desirable Storey Grove community! Featuring a thoughtfully designed floor plan with TWO Primary suites—one conveniently located on the FIRST floor and the other upstairs—this home offers exceptional flexibility for multi-generational living, extended family, or hosting guests. The functional and versatile layout provides comfortable living spaces ideal for both everyday living and entertaining. Enjoy the convenience of living in a family-friendly community with a community swimming pool and the added benefit of having elementary and middle schools right within the neighborhood—making daily school commutes easier for busy families. one of Storey Grove's most attractive features is its convenient location near Walt Disney World, offering easy access to world-famous theme parks, shopping, dining, and entertainment. With convenient access to major highways and everyday essentials, this home combines a desirable location with comfortable Florida living. Easy Access to Major Highways, Shopping, Dining, and Entertainment Don't miss this wonderful opportunity to enjoy comfort, flexibility, and convenience in the sought-after Storey Grove community, just minutes from the magic of Disney!

16549 Parable Way, Winter Garden
14503 Avenue Of The Rushes, Winter Garden
$850,000
4 Beds ⋅ 4 Baths ⋅ Signature Lakes SubDv. ⋅ 34787 Zip Code
Pro Pics Coming Soon - 1st time on the market * Welcome to this beautiful and incredibly maintained home offering 4 bedrooms, 3.5 bathrooms, and approximately 3,315 square feet of living space in the desirable Signature Lakes community of Independence * Built in 2007, this spacious two-story home offers an inviting blend of comfort, style, and room to entertain * Attractive curb appeal, a welcoming covered entry, paver driveway, and tropical landscaping create a memorable first impression * Inside, the generous floor plan provides flexibility for everyday living, entertaining guests, and enjoying the Florida lifestyle * Step outside to the private screened pool area and create your own backyard retreat, perfect for relaxing and enjoying the sunshine year-round * Conveniently located near shopping, dining, major roadways, and the many amenities of Winter Garden, this property offers an excellent opportunity to enjoy the Central Florida lifestyle, with community recreation and outdoor activities. Community amenities include a clubhouse, 2 resort-style swimming pools, fitness facilities, tennis and basketball courts, playgrounds, parks, and community boat ramps and docks providing access to Lake Hancock.

14503 Avenue Of The Rushes, Winter Garden
14492 Sunbridge Circle, Winter Garden
$1,060,000
5 Beds ⋅ 4 Baths ⋅ Bradford Crk-Ph Ii SubDv. ⋅ 34787 Zip Code
Welcome to the gated community of Bradford Creek in Winter Garden. This luxurious home has 5 bedrooms, 4 bathrooms and a 3-car garage. The kitchen features an over extended island, walk in pantry, 5-burner gas cooktop, top of the line appliances. Enjoy the oversized covered patio with friends and family. Great for entertaining. There are two ensuite bedrooms, one downstairs, and one upstairs, perfect for mother-in-law and/or guests. The downstairs ensuite is hidden behind a custom built secrete door with its private access to the backyard. The master bedroom is huge with 2 walk-in closets and a bathroom features dual rain shower heads. This home is top of the line with all modern accessories like Cat 6 Ethernet, tankless gas water heater, ring camera at front door and smart lights and much more. Come see for yourself.

14492 Sunbridge Circle, Winter Garden
15102 Stuttgart Alley, Winter Garden
$525,000
4 Beds ⋅ 3 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code
Amazing 4 bedroom 2.5 bath home in the Watermark community near the heart of Hamlin off 429. Built in 2020 with 2204sf, this home offers an open floor plan with great style, architecture, and tasteful decor. The open-concept with kitchen, dining, living room, and cute side cubby combined is great for entertaining. Spacious living areas, contemporary fixtures, and vinyl flooring through out the first floor. The open kitchen is well designed and very pleasing to view with white upgraded cabinets, crown molding, accented with all stainless-steel appliances, quartz countertops, tiled backsplash, and a walk-in pantry. Second floor has a nice size loft, and enter into the large primary bedroom with double doors with huge primary bath. Two separated large vanities, large walk-in shower, large closet, linen closet and toilet room. The washer and dryer have a large laundry room and the other bedrooms share the hall bath with large counter and dual sinks. The back driveway has pavers up to the house and the front of the house looks over a huge, dry retention field. The neighborhood has two community pools, a deluxe resort-style pool and splash pad equipped with cabanas, a nearby gym, and a cool Fire pit overlooking a small pond lined up for viewing of the Disney fireworks! Located perfectly near the heart of Hamlin off Seidel Rd and 429 with convenience just minutes away from brand-new restaurants, shopping, healthcare facilities.

15102 Stuttgart Alley, Winter Garden
14026 Frasier Street, Winter Garden
$464,900
3 Beds ⋅ 3 Baths ⋅ Highland Ridge SubDv. ⋅ 34787 Zip Code
SELLER OFFERING $10,000 TOWARDS BUYER CLOSING COST WITH AN ACCEPTABLE OFFER!! Welcome to this beautiful 2023-built home in the desirable Highland Ridge community of Winter Garden! Featuring 3 bedrooms, 2.5 bathrooms, and 1,985 square feet of thoughtfully designed living space, this home offers the perfect combination of modern comfort, functionality, and energy efficiency. Step inside and discover a bright, spacious open-concept main floor, ideal for everyday living and entertaining. The inviting covered front porch adds charm and provides a wonderful place to relax and enjoy the Florida lifestyle. Upstairs, you’ll find a versatile loft perfect for gathering and relaxation, along with a private primary suite offering comfort and privacy. The additional bedrooms provide flexibility for family members or guests. Built by Meritage Homes, known for its innovative energy-efficient features, this property is designed with comfort and potential energy savings in mind. Additional highlights include a two-car garage and access to the community pool. Location is another outstanding feature! Just a short walk from the new Ovation Elementary School and the Flamingo Crossings shopping center, offering a variety of restaurants, fast-casual dining options, grocery stores, a fitness center, and convenience stores, making everyday living exceptionally convenient. The property also provides easy access to major roadways and Orlando’s world-famous attractions. Don’t miss your chance to own a nearly new home in one of the Orlando area’s most desirable locations. Schedule your private showing today!

14026 Frasier Street, Winter Garden
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