Winter Garden Homes with Two Story Property Description

Winter Garden Homes with Two Story Property Description

Welcome to Winter Garden, Florida—a vibrant city that beautifully blends small-town charm with modern amenities. Nestled just a short drive from Orlando, Winter Garden is known for its picturesque landscapes, rich history, and an array of outdoor activities. The historic downtown area is a delightful hub, featuring quaint shops, delightful eateries, and a lively farmers market that draws locals and visitors alike. With its scenic lakes and lush parks, Winter Garden offers the perfect backdrop for families and individuals seeking a serene yet dynamic lifestyle.

When it comes to housing, Winter Garden boasts an impressive selection of two-story homes that cater to a variety of tastes and lifestyles. These spacious properties are designed with family living in mind, featuring open floor plans that seamlessly connect living, dining, and kitchen areas—perfect for entertaining or cozy family gatherings. Many of these homes come equipped with modern amenities, including gourmet kitchens, luxurious master suites, and energy-efficient features that ensure comfort and convenience.

Imagine enjoying your morning coffee on a charming balcony or hosting summer barbecues in a beautifully landscaped backyard. The two-story homes in Winter Garden provide ample room for growth, whether you’re starting a family or simply seeking more space for your hobbies. With excellent schools, nearby shopping, and easy access to major highways, Winter Garden is not just a place to live; it’s a community where memories are made. Discover your dream two-story home in this enchanting city and embrace the lifestyle you’ve always desired!

Newest Winter Garden Homes with Two Story Property Description

5 Beds ⋅ 4 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code

If you’ve been searching for a spacious Winter Garden home with a private pool, peaceful conservation views and room for everyone, this former model may be exactly what you’ve been waiting for! With 5 bedrooms, 4 full bathrooms and the potential for a 6th bedroom, this home combines privacy, flexibility and Florida indoor-outdoor living in a way that’s increasingly difficult to find. Situated on a peaceful wooded conservation lot, the home has been thoughtfully updated with a renovated kitchen, LVP flooring throughout the first floor, and new carpet and paint upstairs. Generous living and dining areas provide plenty of room for everyday living and entertaining, while the family room features easy access to the screened pool and deck. The spacious primary suite includes a private sitting area and built-in shelving, creating a comfortable retreat. Upstairs, the oversized bonus room with its own adjoining full bathroom offers exceptional flexibility and could serve as a second primary suite, private guest quarters, media room or game room. Need even more space? The downstairs office could potentially be converted into a 6th bedroom, making this floor plan adaptable to a variety of needs. Step outside to one of the home's most appealing features—the screened-in pool and deck overlooking the wooded conservation area. With no immediate rear neighbor, it's a private setting for morning coffee, afternoons by the pool, entertaining friends or simply relaxing at the end of the day. Located in the beautiful gated Wintermere Pointe community, this home brings together the space, privacy and flexibility along with a private pool and conservation setting that can be difficult to find. Call and schedule your private showing today!

2242 Wintermere Pointe Drive, Winter Garden

6 Beds ⋅ 4 Baths ⋅ Mcallister Landing SubDv. ⋅ 34787 Zip Code

1523 Juniper Hammock Street welcomes you with a striking two-story façade, graceful architectural lines, and a beautifully composed exterior that creates an impressive sense of arrival. At the rear, the home opens to a lush, peaceful setting dominated by mature trees and natural greenery, offering a refreshing backdrop and a greater sense of privacy. A partial water view from the side adds another layer of beauty without taking away from the secluded, tree-lined atmosphere. Together, the elegant exterior and serene natural surroundings create a home that feels both distinguished and wonderfully connected to the outdoors.

1523 Juniper Hammock Street, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Amazing, 4 bedroom, 3.5 bath 3327sqft, WATERFRONT home in highly desirable Waterleigh west of Disney. This luxurious home has a large covered and paved front porch to watch the morning rise and day go by and a large covered back paved patio to enjoy those peaceful, colorful, sunsets over the water with about 50 feet of frontage. The foyer and front formal dining room have elegant arched hallways and coffered ceilings. Walk into the main living area through the main hall or through the Butlers pantry to the Gourmet kitchen. Next to the Butlers pantry is a large walk-in closet pantry for extra storage. The Gourmet kitchen has light, tiered, cabinets with crown molding, all stainless steel appliances, and accented by gorgeous Quartz counters. glass cooktop with separate built in microwave and oven. (French door fridge with bottom freezer will be installed.) The large sink island features the sink and breakfast bar overlooking the family and cafe area with plenty of windows and door for great neutral light and amazing views of the water and large back yard . The home has tall ceilings and tiled with wood plank type tile throughout the first floor except for the first floor Master bedroom. The Master also faces West overlooking the pond for great sunset views. Very large with coffered ceilings and lots of light. The cute double doors lead into the spacious master-bath with large separate vanities, double sinks, separate shower stall, separate toilet room, garden tub, linen closet, and Massive clothes closet. Back in the main great room is a hall filled with more cabinet storage space, leading to the large laundry room, garage, and stairs. The beautiful wood stairs and iron rail leads up to a spacious 20x18 loft/game room. All of the bedrooms have walk-in closets. One has a separate private bath, and the other two split bedrooms share a hall bath split with dual sinks and separate room for baths and toilet for maximum use. The home has modern decor styled raised panel doors throughout and plenty of storage space. This home has Smart technology for easy use and remote functionality. This amazing home is in the highly desirable community “Waterleigh.” Located just off the 429 west of Disney, This community amenities include a huge resort style pool, fitness gym, club house, dog park, huge sports fields, playground, beach volleyball, Tennis, lake view BBQ/picnic area, with sidewalks that wind around the scenic lakes, nature, and community for a relaxing and enjoyable lifestyle with periodic fitness stops if you choose. Fast and easy access anywhere. New Florida Hospital, restaurants and shopping are all close and many more are being built nearby. Great schools; Water Spring Elementary, Water Spring Middle, and Horizon Highschool.

8819 Sonoma Coast Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hawksmoor-Ph 1 SubDv. ⋅ 34787 Zip Code

Welcome home to Hawksmoor, a highly sought-after community in Horizon West and Winter Garden. This home is like new, as it was used primarily as a Vacation home. Just minutes from the theme parks and major highways. This spacious bungalow-style home offers 2,372 sq ft of contemporary design for today's lifestyle. The highlight of the home is the upgraded Gourmet Kitchen, complete with light cabinetry, a beautiful backsplash, etc. Just off the Kitchen is a wonderful space for entertaining friends and family. In addition, you have a private office on the first floor.. Dining room chandelier along with washer & Dryer do not convey Upstairs,you'll find an expansive loft that provides multiple options as a Media Room, playroom, game room, etc. Two additional bedrooms upstairs are a very generous size to be used as bedrooms or guest rooms.. The primary suite features a beautiful tray Ceiling,a luxurious en-suite bathroom, and abundant closet Space. A second-floor laundry is ideal for the entire family. A list of the multilpe amenties offered by this sought after community. Call to view this like new home before it is to late!

16614 Wingspread Loop, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to 15675 Panther Lake Drive, an exceptional lakefront residence within the prestigious Lakeshore Preserve community of Winter Garden, where refined interiors, expansive water views, and effortless Florida living come together in a beautifully curated setting. Offered fully furnished, this sophisticated five-bedroom, five-bathroom residence has been thoughtfully enhanced with custom millwork, elevated finishes, and carefully selected upgrades throughout. The heart of the home is an expansive open-concept living space, seamlessly connecting the family room, dining area, and kitchen while framing beautiful views of the lake. Designed equally for intimate everyday living and sophisticated entertaining, the main level also features a dedicated coffee station, generous pantry and storage spaces, laundry room, and a private primary suite offering the convenience of first-floor living. One of the three garage bays has been thoughtfully transformed into a fully equipped private fitness studio, creating a dedicated wellness space within the residence while offering the flexibility to be converted back to garage use if desired. Upstairs, four additional bedrooms are complemented by a spacious loft and private home office. Expansive windows throughout the upper level capture the lake views and bring an abundance of natural light into the home. Beyond its interiors, the property's waterfront setting creates a sense of openness and tranquility, offering a beautiful lake view and access, summer kitchen, Florida room, heated pool and a spa. It is a true oasis from morning through evening. Ideally positioned in Winter Garden, the residence provides the privacy and distinction of an upscale community while remaining conveniently connected to the area's exceptional dining, shopping, entertainment, and lifestyle destinations. 15675 Panther Lake Drive represents a rare opportunity to acquire a fully furnished*, beautifully appointed lakefront home where comfort, functionality, and the Florida lifestyle exist in perfect balance.

15675 Panther Lake Drive, Winter Garden

2 Beds ⋅ 3 Baths ⋅ Signature Lakes Parcel 1b SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained 2 bedroom, 2 bath townhome in the highly sought-after Independence community at Signature Lakes. This home offers a bright, open layout with comfortable living spaces perfect for both everyday living and entertaining. The kitchen flows seamlessly into the dining and living areas, creating a welcoming atmosphere filled with natural light. Both bedrooms are generously sized, offering privacy and flexibility for guests, a home office, or a cozy retreat. The attached 2-car garage provides secure parking and additional storage—an added convenience rarely found in townhome living. The HOA includes internet access, pest control, ground maintenance and access to the pool, clubhouse and fitness center. Independence is known for its peaceful surroundings, well-kept landscaping, and prime location near top Winter Garden attractions and highly rated schools. Enjoy easy access to major highways, shopping, dining, and the vibrant Hamlin and Horizon West areas. Whether you're relaxing at home or exploring everything the community has to offer, this townhome delivers comfort, convenience, and a true sense of home. Come experience the lifestyle waiting for you at Independence.

14766 Peekskill Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully designed 4-bedroom, 3.5-bath home offering stylish upgrades and exceptional indoor-outdoor living in the charming Town of Oakland. From the inviting covered entry and brick-paver driveway to the bright, open interior, every space has been thoughtfully designed for comfortable everyday living and effortless entertaining. The impressive kitchen features abundant cabinetry, expansive countertops, stainless-steel appliances, a natural gas cooktop, built-in oven and microwave, subway-tile backsplash, and an oversized center island with generous seating. Fabulous pantry features custom shelving and refrigerator. The kitchen flows seamlessly into the spacious living area, highlighted by a dramatic floor-to-ceiling accent wall with a sleek electric fireplace and built-in cabinetry. The formal dining room offers soaring ceilings, abundant natural light, and an elegant statement fixture. The spacious first-floor primary suite provides a peaceful retreat with a tray ceiling and a luxurious ensuite bathroom featuring a large glass-enclosed shower, separate soaking tub, dual-sink vanity, huge walk-in closet and distinctive designer finishes. Upstairs, you will find three additional bedrooms and a versatile bonus room—perfect for a home office, media room, playroom, or additional gathering space. One of the upstairs bedrooms includes a private ensuite bathroom, providing an ideal arrangement for guests. Sliding glass doors open to a private, screened outdoor oasis featuring an extended brick-paver patio, covered dining space, multiple conversation areas, and a relaxing 8-person spa—perfect for enjoying Florida living throughout the year. A privacy fence enhances the peaceful backyard setting. Residents of Hull Island enjoy access to a community pool, dog park, playground, and picnic area. The neighborhood also offers convenient access to the Oakland Nature Preserve, 22-mile West Orange Trail, and downtown Oakland. Enjoy the town’s Thursday farmers market, Arts and Heritage Center, local coffee shop, and Speer Park, with vibrant downtown Winter Garden just minutes away. Conveniently located near major highways, theme parks, downtown Orlando, Orlando International Airport, restaurants, shopping, and hospitals, this exceptional Oakland home combines contemporary style, thoughtful design, and an outstanding Central Florida lifestyle. You're only an hours' drive to some of Florida's finest beaches. Schedule your private showing today!

1016 Catori Road, Oakland

5 Beds ⋅ 4 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to this impressive 5-bedroom, 4-bath home with a 3-car garage in the highly desirable Hawksmoor community of Horizon West. Built in 2021, this beautifully designed two-story home offers an exceptionally flexible floor plan, generous indoor and outdoor living spaces, peaceful water and natural views, plus an outstanding energy feature a Tesla whole-home backup power system with solar.One of the home's most valuable upgrades is its Tesla backup battery and solar system designed to provide whole-home backup power. The sellers currently enjoy an electric bill of approximately $34 per month, and the entire solar and battery system will transfer to the new buyer at no additional cost, providing an exceptional combination of energy efficiency, backup power and long-term value.From the moment you arrive, the home makes a great first impression with attractive architectural details, mature landscaping, a paver driveway and three-car garage. Step inside to a welcoming foyer and a dedicated private office, providing an ideal space for working or studying from home.The heart of the home is the expansive open-concept living area, where the kitchen, dining and family rooms flow seamlessly together. The spacious kitchen features an oversized center island with abundant seating, extensive cabinetry and counter space, gas cooktop, built-in oven and microwave, stainless steel appliances and a separate walk-in pantry. Large sliding glass doors fill the living area with natural light and create a wonderful connection to the outdoor living space.The first floor also features a bedroom and full bath, offering excellent flexibility for overnight guests, extended family or multigenerational living.Upstairs, the oversized primary suite provides a relaxing retreat with a tray ceiling, multiple windows and beautiful views. The spacious primary bath features dual vanities, a soaking tub and separate walk-in shower. Additional bedrooms and baths provide plenty of room, while the conveniently located upstairs laundry room makes everyday living easier.An expansive upstairs loft/family room provides an entirely separate living area with endless possibilities as a media room, game room, playroom, fitness area or second family room.Outdoor living is another standout feature. Large sliding doors open to an extended covered lanai overlooking the spacious fenced backyard, water and natural green space beyond. Whether enjoying your morning coffee, entertaining friends or relaxing at the end of the day, this peaceful setting provides an inviting extension of the home with plenty of usable yard space.Beyond the property, Hawksmoor offers an amenity-rich lifestyle with a resort-style community pool, clubhouse, fitness center, playground and outdoor recreation. Located in Horizon West, the community provides convenient access to shopping, dining and entertainment at Hamlin, area parks and trails, SR-429, Walt Disney World and the many attractions of Central Florida. Historic Downtown Winter Garden, with its restaurants, shops, farmers market and West Orange Trail, is also within easy reach.

16773 Wingspread Loop, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Oakland Parkb-3 SubDv. ⋅ 34787 Zip Code

A rare opportunity in highly sought-after Oakland Park—this beautifully furnished, turnkey home offers **4 spacious bedrooms, 3 full bathrooms, including a first-floor bedroom and full bath ideal for guests, extended family, or an in-law arrangement**, plus the exceptional Winter Garden lifestyle buyers are looking for. Tall ceilings, 8-foot doors, elegant architectural details, high-end décor, and thoughtfully designed living spaces create an elevated yet comfortable feel throughout. (If the buyer prefers not to keep the furniture and furnishings, they can be excluded from the sale.) The showpiece kitchen is truly the heart of the home, featuring premium quartz countertops, a 5-burner gas range, stainless steel hood, striking designer backsplash, and spacious walk-in pantry. The spa-inspired primary suite offers an expansive private bathroom and generous walk-in closet, creating the perfect retreat. And for a little extra personality, the home even has its very own “Harry Potter” closet! Enjoy Florida living from the inviting screened front porch, complete with a porch swing perfect for morning coffee, an afternoon book, or relaxing at the end of the day. The back patio and fenced yard provide another comfortable setting for entertaining, outdoor dining, or simply enjoying the beautiful Florida weather. An expansive 3-car garage offers exceptional space and storage. Offered fully furnished with beautiful, high-end furnishings and décor, this home is truly turnkey—just bring your suitcase and start enjoying the lifestyle. Located near highly regarded schools and just moments from the West Orange Trail, walk, bike, take your golf cart, or drive to charming Downtown Winter Garden, the Farmers Market, restaurants, shopping, and entertainment. Move in before the holidays and experience everything this incredible community has to offer, including festive neighborhood traditions and upcoming celebrations such as the golf cart parade, fall festival, and more. An exceptional opportunity to own a remarkably equipped home in one of the area’s most desirable communities at an amazing value.

226 Hammock Preserve Loop, Oakland

3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2e SubDv. ⋅ 34787 Zip Code

This stylish townhome in one of Winter Garden’s most desirable resort-style communities, offers a blend of comfort, convenience, and everyday luxury. The home sits in a beautifully planned neighborhood known for its amenities,GainesvillecinfgainesLoo surroundings, and welcoming atmosphere—an ideal setting for anyone seeking a relaxed yet connected lifestyle. Its location is a major highlight. Winter Garden is home to some of Central Florida’s top-rated schools, making this property especially appealing for families who value strong educational options. You’re also just minutes from premier shopping and dining at places like Hamlin Town Center and Winter Garden Village, giving you easy access to everything from groceries to entertainment. And of course, the magic of Disney theme parks is right around the corner, making weekend outings effortless and adding a touch of excitement to everyday life. This townhome places you in a thriving, fast-growing area where convenience meets resort-style living. With beautiful community amenities, excellent schools, nearby shopping, and world-famous attractions close enough to enjoy anytime, it’s a standout opportunity in one of Winter Garden’s most sought-after.

10119 Salt Point Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lake Roberts Lndg E SubDv. ⋅ 34787 Zip Code

Your chance to own the FORMER MODEL for entire community. Set behind the GATED ENTRY of Lake Roberts Landing with community fishing pier to 116 acre Lake Roberts. THE IDEAL FLOOR PLAN you have been waiting for, 5 beds, office, movie theatre and bonus.. PLUS this rare gem... Primary bed and an additional En Suite on 1st floor !!! Incredible street presence and MASSIVE fenced back yard. Oversized covered lanai with summer kitchen provides the ideal place to relax and entertain. Screen enclosed pool and spa with paver deck competes the perfect back yard to embrace the Florida Lifestyle. Entering the home you are greeting with soaring ceilings of a foyer replicating a great hall feel. Formal dining and private office (on top of the 5 bedrooms) flank the entry, Both boasting amazing detail and carpentry that would be expected in the former model. Pass the wet bar for entertaining to the formal living room with same soaring ceiling height as the foyer itself. The heart of the home well appointed with timeless wood cabinets, lots of workspace and vented cook top too. The family room overlooks the pool, yard and lanai. DOWNSTAIRS MASTER is incredible and a RARE SECOND EN SUITE DOWNSTAIRS is perfect for guests or aging family members. Ascend the showstopping curved staircase to the equipped home theatre and additional BONUS ROOM. 2 large secondary bedrooms with jack and jill set up PLUS another EN SUITE/ 2nd primary bedroom on the 2nd floor. ALL beds have a walk-in closet too ! 3 car tandem garage, tile roof. Minutes to 429 expressway, countless shopping and dining options in literally every direction. Sought after K-12 school district plus Foundation Academy and Windermere Preparatory school campuses minutes away. Disney less than 15 away and 20 to Downtown Orlando. This is truly an amazing opportunity for one buyer. Move fast, this is one that is priced to sell.

1720 Lake Roberts Landing Drive, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to 5506 New Independence Pkwy, offering a flexible floor plan with 5 bedrooms, 3.5 bathrooms, and a dedicated office in the highly sought-after Independence community of Winter Garden. Step inside to a bright, refreshed interior featuring a renovated kitchen with white cabinetry, quartz countertops, an oversized island with seating, stainless steel appliances, and updated finishes. New luxury vinyl plank flooring adds a fresh, modern look throughout the primary and upstairs living areas, while tile flooring provides durability in the main living spaces. The versatile layout offers plenty of room to live, work, and entertain. The dedicated office provides a separate workspace, while the 5th bedroom upstairs can easily be converted back into an open loft to fit your needs. The primary suite features a spacious bath with dual sinks, granite countertops, a soaking tub, and separate shower. Outside, enjoy a covered rear patio, fenced backyard, and plenty of space to create your own outdoor retreat, including the potential to add a pool. A rear-entry garage and welcoming front porch complete the home. Located in Winter Garden's popular Independence community, this home combines flexible living space, thoughtful updates, and a backyard ready for your vision. Schedule your private showing today and see everything 5506 New Independence Pkwy has to offer!

5506 New Independence Parkway, Winter Garden

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