Winter Garden Homes with City View

Winter Garden Homes with City View

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County that perfectly blends small-town charm with modern amenities. Known for its picturesque landscapes and vibrant downtown area, Winter Garden is a hidden gem that offers a delightful lifestyle for families, retirees, and everyone in between.

One of the most captivating features of Winter Garden is its stunning homes that boast breathtaking city views. Imagine waking up each morning to panoramic vistas that showcase the beauty of the city against a backdrop of serene skies. These residences are designed to maximize natural light and provide an inviting atmosphere, making them perfect for relaxation and entertaining.

Winter Garden is not just about beautiful homes; it’s also a community rich in culture and recreation. The historic downtown area is lined with quaint shops, delightful restaurants, and lively farmers’ markets, creating a vibrant social scene. Outdoor enthusiasts will appreciate the numerous parks and trails, including the scenic West Orange Trail, perfect for biking, walking, or simply enjoying the Florida sunshine.

Families will find Winter Garden to be an ideal place to raise children, with top-rated schools and a plethora of community events throughout the year. From art festivals to holiday parades, there’s always something happening that brings the community together.

Whether you’re looking for your dream home with stunning city views or simply want to enjoy the warm, welcoming atmosphere of Winter Garden, this city offers a unique blend of comfort, convenience, and charm that’s hard to resist. Discover the magic of Winter Garden today!

Newest Winter Garden Homes with City View

$915,000
3 Beds ⋅ 4 Baths ⋅ Park Place At Winter Garden SubDv. ⋅ 34787 Zip Code
Experience luxury living in the heart of historic downtown Winter Garden! This beautifully designed corner-unit brownstone offers 3 bedrooms, 3.5 bathrooms, 2,242 square feet of thoughtfully crafted living space, and an unbeatable location just steps from everything that makes downtown so special. Situated right next to Plant Street Market and Crooked Can Brewing Company, you'll enjoy effortless access to the award-winning Saturday Farmers Market, local festivals, live entertainment, boutique shopping, and an incredible selection of restaurants and cafés, all just outside your front door. Step inside to discover a the first-floor layout featuring a private bedroom with its own en suite bathroom, creating the perfect retreat for overnight guests, extended family, or even a private home office. The second floor is the heart of the home, where an open-concept living, dining, and kitchen area creates an inviting atmosphere for both entertaining and everyday living. As a coveted corner unit, oversized windows fill the space with natural light, while crown molding adds an elegant finishing touch throughout. The gourmet kitchen is designed to impress, showcasing an oversized center island, stainless steel appliances, stylish finishes, generous counter space, and abundant cabinetry. A dedicated bar area nearby makes hosting gatherings even more effortless, while the adjoining living room features access to the covered balcony and large sliding doors, giving you the perfect place to enjoy fresh air or unwind after a day exploring downtown. Occupying the third floor, the spacious primary suite offers a peaceful escape with a large walk-in closet and a luxurious en suite bathroom complete with dual vanities and a stunning freestanding soaking tub. An additional upstairs bedroom provides generous closet space, abundant natural light, and comfortable accommodations for your loved ones. Additional highlights include a two-car garage and a location within Winter Garden's highly desirable golf cart district, making it easy to explore downtown's vibrant shops, restaurants, parks, and community events without ever needing your car. Convenient access to major highways places the rest of Central Florida within easy reach, while your everyday lifestyle is centered around one of the region's most sought-after downtown destinations. If you've been searching for luxurious low-maintenance living with unmatched walkability, this exceptional townhome is the opportunity you've been waiting for. Schedule your private showing TODAY!!!

484 W Plant Street, Winter Garden
$900,000
6 Beds ⋅ 6 Baths ⋅ East Garden Manor Add 03 Rep SubDv. ⋅ 34787 Zip Code
Rare opportunity to own a unique corner-lot property featuring two attached residences, each with its own street frontage, private entrance, covered front porch, two-car garage, no HOA, and identical floor plan. Unlike a traditional side-by-side duplex, each residence faces a different street, creating the appearance and feel of two individual homes while offering the convenience of a connected design. Designed for both comfort and flexibility, each home features a spacious living and dining area, a bright kitchen with French doors leading to the backyard, and a convenient first-floor guest powder bath. Upstairs, all bedrooms are thoughtfully positioned for added privacy. The primary suite includes a private ensuite bath, while the secondary bedrooms are generously sized and complemented by abundant storage throughout each residence. The Wilson Street residence has been thoughtfully upgraded with luxury vinyl flooring, an enhanced kitchen with stone counters and gas cooking, beautifully updated bathrooms, and an attractive staircase that adds character and style. The Maple Street residence has been a consistently popular rental and has been exceptionally maintained, offering a spotless interior that reflects pride of ownership. The location offers exceptional convenience with nearby access to Downtown Winter Garden, one of Central Florida’s most sought-after destinations. Enjoy a vibrant mix of locally owned restaurants, cafés, boutiques, specialty shops, the award-winning Winter Garden Farmers Market, seasonal festivals, live entertainment, and the renowned West Orange Trail. The property also provides convenient access to the Florida State Road 429, Florida State Road 408, and Florida’s Turnpike, making travel throughout Central Florida simple. Popular destinations, including Winter Garden Village, Walt Disney World Resort, major employment centers, shopping, dining, entertainment, parks, and everyday conveniences, are all nearby. Whether you’re seeking a property that offers exceptional flexibility for evolving lifestyle needs, the opportunity to generate rental income, or the convenience of two complete residences under one roof, this distinctive property delivers a rare combination of privacy, functionality, and long-term versatility. Opportunities like this are seldom available, especially with a layout that allows each residence to maintain its own identity while remaining connected.

402 E Maple Street, Winter Garden
$489,990
4 Beds ⋅ 2 Baths ⋅ Stoneybrook West 47/78 SubDv. ⋅ 34787 Zip Code
Selker motivated! Welcome to this beautifully maintained 4-bedroom, 2-bath home located in the highly desirable gated golf community of Stoneybrook West in Winter Garden. This move-in-ready residence features an open and spacious floor plan with separate living and dining areas, high ceilings, abundant natural light, and ceramic tile throughout. The upgraded kitchen offers granite countertops, ample cabinet space, and all appliances are included. The spacious primary suite features a large walk-in closet and an updated bathroom with skylights, dual vanities, a garden tub, and a separate shower. Enjoy outdoor living in the fully fenced backyard with a large patio, perfect for entertaining or relaxing. Recent updates and meticulous care make this home a true standout. Roof replaced in 2022. Property comes with solar panels. Residents enjoy resort-style amenities including a community pool, fitness center, tennis and basketball courts, playgrounds, lake access, fishing pier, boating, and 24-hour guarded gate security. Conveniently located near top-rated schools, shopping, dining, major highways, downtown Winter Garden, and Orlando's world-famous attractions. Don't miss this exceptional opportunity—schedule your private showing today!

2227 Oakington Street, Winter Garden
$800,000
4 Beds ⋅ 2 Baths ⋅ Fries Winter Garden SubDv. ⋅ 34787 Zip Code
Coming Soon! Awesome Opportunity to own in Historic Winter Garden. LOT parcels in the front are being sold seperate.

214 S Woodland Street, Winter Garden
$850,000
3 Beds ⋅ 4 Baths ⋅ Park Place At Winter Garden SubDv. ⋅ 34787 Zip Code
DOWNTOWN WINTER GARDEN LIVING-CORNER END UNIT JUST STEPS FROM PLANT STREET! Leave the car in the garage and walk to dinner, the Saturday Farmer's Market, Crooked Can, live music, community events and the West Orange Trail. This beautifully updated 2432 square foot townhome offers the rare combination of a true Downtown Winter Garden lifestyle, generous living space, three ensuite bedrooms and a two car garage. Inside, the home feels practically new, with fresh paint throughout and an exceptionally well-maintained interior that shows beautifully. The END-UNIT DESIGN brings in additional natural light and provides a more open, private feel than an interior townhome. Wood-look tile flooring, crisp white trim, crown molding, recessed lighting, modern door hardware, decorative wall trim, and a cohesive neutral palette create a bright, polished, move-in-ready interior. The open main living level is designed for everyday comfort and entertaining, with the kitchen, dining, and living areas flowing together in one spacious, connected layout. The kitchen features light cabinetry, stone countertops, subway tile backsplash, stainless steel appliances, a NATURAL GAS RANGE, vent hood, pendant lighting, and an oversized island with seating. The adjoining dining and living areas offer generous space, excellent natural light, balcony access, and plenty of room to gather without feeling crowded. The flexible three-level floor plan includes THREE ENSUITE BEDROOMS, giving every bedroom its own private bath and providing exceptional privacy for family and guests. The first-floor ensuite bedroom creates a private retreat for overnight visitors, extended family, work-from-home needs, hobbies, or multigenerational living. Upstairs, the spacious primary suite features a beautifully updated bath with dual vanities, new flooring, and a BRAND-NEW STEAM SHOWER with floor-to-ceiling tile, built-in bench, recessed niche, decorative tile accent, and a spa-inspired design. A third ensuite bedroom, upstairs laundry, generous closets, built-in storage, and additional storage throughout make the home as practical as it is attractive. An ELEVATOR-READY LAYOUT adds long-term flexibility and future convenience. Additional highlights include NATURAL GAS SERVICE, a tankless water heater, updated fixtures, balcony, landscaped courtyard setting, and a TWO-CAR GARAGE with valuable parking and storage in a location where both are especially desirable. Compared with many current Downtown Winter Garden townhome options, this home offers a compelling combination of END-UNIT POSITIONING, generous square footage, updated condition, three private bedroom suites, and a lower price than several smaller competing properties. Schedule your private showing today.

461 Geranium Park Way, Winter Garden
$1,349,000
7 Beds ⋅ 4 Baths ⋅ Mcallister Lndg SubDv. ⋅ 34787 Zip Code
Welcome to an extraordinary Winter Garden retreat where luxury, flexibility, and resort-style living come together in one remarkable residence. Situated on a premium corner lot, this expansive 7-bedroom, 4-bath home offers over-the-top living spaces designed for entertaining, multi-generational living, and creating unforgettable memories. Step inside to soaring ceilings, abundant natural light, and an open-concept floor plan that effortlessly blends elegance with everyday comfort. The chef-inspired kitchen serves as the heart of the home, featuring an oversized island, breakfast bar, abundant cabinetry, and seamless flow into the spacious family room and café dining area. The thoughtfully designed layout includes both the owner's suite and a guest bedroom on the main level, providing ideal accommodations for extended family or visitors. Upstairs, a sprawling game room, dedicated home theater, and additional bedrooms create the ultimate entertainment hub for family and guests alike. Outside, your private backyard oasis awaits. Relax by the sparkling in-ground pool, entertain under the covered lanai, or host gatherings in the fully equipped summer kitchen. The fully fenced yard provides privacy while maximizing enjoyment of Florida's year-round sunshine. Perfectly positioned just minutes from Historic Downtown Winter Garden, Orlando's world-famous attractions, premier dining, shopping, and entertainment, this exceptional home offers the lifestyle today's buyers are seeking—space to gather, room to grow, and amenities that make every day feel like a vacation.

1698 Juniper Hammock Street, Winter Garden
$1,095,000
4 Beds ⋅ 4 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code
Welcome to 30 North Park, an exceptional townhome located in the heart of Historic Downtown Winter Garden — directly on the West Orange Trail and just steps from Plant Street Market, Crooked Can Brewery, local dining, shopping, and the weekly Farmer’s Market. This modern farmhouse-style residence offers four spacious bedrooms, each with a private en-suite bathroom and custom-fitted closets, providing comfort, privacy, and flexibility for guests, multigenerational living, or work-from-home needs. A first-floor bedroom serves as an ideal guest retreat, office, or flex space. The second level features an open-concept living area anchored by a designer kitchen complete with Bosch natural gas appliances, a large island, quartz countertops, farmhouse sink, artisan tile backsplash, and floor-to-ceiling windows showcasing views toward downtown and the West Orange Trail. A secondary bedroom with dramatic custom windows adds abundant natural light. On the third floor, dual primary suites offer spacious layouts, oversized windows, powered blinds, spa-inspired walk-in showers, and quartz-finished baths. Thoughtful upgrades throughout include warm wood flooring, patterned tile accents, modern black lighting fixtures, and extensive storage. Built with an STC soundproofing rating of 69, the home provides a quiet interior environment while remaining in one of Central Florida’s most vibrant walkable districts. Enjoy balcony views overlooking the trail and experience low-maintenance living with unmatched proximity to Historic Winter Garden’s amenities. Experience refined, walkable living in the heart of Winter Garden — schedule your private showing today.

64 N Park Avenue, Winter Garden
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