Winter Garden Homes with City View

Winter Garden Homes with City View

Winter Garden is a charming city located in Orange County, Florida. Known for its picturesque landscapes, friendly community, and vibrant downtown area, Winter Garden is a highly sought-after destination for both residents and visitors.

Situated in the heart of the Sunshine State, Winter Garden offers a perfect blend of small-town charm and modern amenities. With its close proximity to Orlando, residents can enjoy the best of both worlds – a peaceful suburban lifestyle with easy access to the bustling city.

One of the highlights of living in Winter Garden is the stunning city views that many homes offer. Whether you're looking for a cozy bungalow or a spacious modern mansion, there are plenty of options available that provide breathtaking vistas of the city skyline. Imagine waking up to the sight of twinkling city lights or enjoying a beautiful sunset from the comfort of your own home.

Not only does Winter Garden offer beautiful homes with city views, but it also boasts a range of recreational activities and attractions. From the West Orange Trail, a popular biking and walking path, to the Winter Garden Farmers Market, where you can find fresh produce and local crafts, there is always something to do and explore in this vibrant city.

If you're looking for a place to call home that combines natural beauty, a close-knit community, and the convenience of city living, Winter Garden might just be the perfect fit. With its true homes with city views, this city offers a unique opportunity to enjoy the best of both worlds.

Newest Winter Garden Homes with City View

$850,000
6 Beds ⋅ 6 Baths ⋅ East Garden Manor Add 03 Rep SubDv. ⋅ 34787 Zip Code
Coming back to market soon after SIGNIFIGANT PRICE REDUCTION- SELLER IS MOTIVATED! RARE DUAL-RESIDENCE PROPERTY | NO HOA | MINUTES TO DOWNTOWN WINTER GARDEN Built in 2021 on a prime corner lot, this custom property features two complete attached residences under one roof. Designed for maximum privacy, each home faces a separate street, featuring its own street address, private covered front porch, and dedicated 2-car garage (4 garage spaces total). Ideal for house-hacking, multi-generational living, or long-term dual-rental income. --- KEY PROPERTY SPECS: Total Living Space: 2,876 heated sq ft Total Bed / Bath: 6 Bedrooms | 4 Full Baths | 2 Half Baths Layout: Identical two-story layouts (3 Beds / 2.5 Baths per side) Parking: 4 total garage bays (2 attached 2-car garages) + separate driveways Year Built: 2021 (Block construction, double-pane windows, zoned HVAC) HOA: None — no monthly fees, no restrictive rental caps --- THE RESIDENCES: Wilson Street Unit: Upgraded with luxury vinyl plank flooring, open-concept living, and an upgraded kitchen featuring stone countertops, gas cooking, and French doors leading out to patio space. Upstairs holds a primary suite with walk-in closet and private bath, plus two guest bedrooms and a second full bath. Maple Street Unit: Turnkey and low-maintenance with clean tile and durable laminate flooring. Features an open living/dining layout, powder bath on the main floor, and 3 bedrooms with 2 full baths upstairs. --- THE LOCATION: Minutes to Historic Downtown Winter Garden, Plant Street dining, breweries, and the award-winning Farmers Market Direct proximity to the West Orange Trail Quick access to SR-50, the 429, and Florida’s Turnpike for easy Central Florida commutes Live in one side and offset your mortgage with the other, keep extended family next door, or rent both for strong cash flow. Contact us today to schedule your private tour!

402 E Maple Street, Winter Garden
$220,000
3 Beds ⋅ 2 Baths ⋅ Palisades SubDv. ⋅ 34787 Zip Code
Discover your next investment or dream home! This spacious 3-bedroom, 2-bathroom condo offers 1288 sqft of well-designed living space in a highly desirable Winter Garden location. Perfect for investors, this unit is ideal for both long-term rentals and lucrative short-term rental opportunities, capitalizing on the area's strong rental demand. Enjoy access to community amenities, including a refreshing pool, and benefit from convenient maintenance services. Don't miss out on this exceptional property with immense potential in a thriving community!

14200 Avalon Road Unit 406, Winter Garden
$520,000
4 Beds ⋅ 3 Baths ⋅ John Lake Pointe SubDv. ⋅ 34787 Zip Code
Motivated seller! Huge price reduction!!! Located in the community of Johns Lake Pointe, this beautifully designed 4-bedroom, 2.5-bath home offers a desirable split floor plan and a spacious 2-car garage. A welcoming front porch sets the tone for this inviting residence. The living room overlooks the private fenced backyard, creating the perfect setting for relaxing or entertaining. The kitchen features chestnut cabinetry, stainless steel appliances, a center island with a sit-in bar, and a separate dining area ideal for gatherings. The primary suite includes a well-appointed primary bathroom with dual sinks, a garden tub, and a walk-in shower. The back porch is protected by a screen. With a recent price improvement, this home presents outstanding value, flexibility, and the opportunity to personalize to your taste. Ideally located less than 20 minutes from Disney, Johns Lake Pointe is a beautifully maintained community offering resort-style amenities, including a clubhouse with a pool and kitchen, fitness center, yoga room, tennis courts, and playground. Enjoy an exceptional lifestyle in a prime location, priced to allow the next owner to create a private oasis. Don’t miss the opportunity to make this remarkable house your home!

745 Marsh Reed Drive W, Winter Garden
$335,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort And Spa Hotel Condominium 3 SubDv. ⋅ 34787 Zip Code
Welcome to Unit 3701 at The Grove Resort & Water Park, a fully furnished seventh-floor condo offering 3 bedrooms, 3 bathrooms, and 1,544 square feet of spacious resort-style living just minutes from Walt Disney World. Designed for comfort and convenience, the residence features an open living and dining area, a fully equipped kitchen with stainless steel appliances and quartz countertops, a full-size washer and dryer, and a private screened balcony—perfect for relaxing after a day at the parks. Owners and guests enjoy an impressive collection of resort amenities, including Surfari Water Park with a FlowRider® Double surf simulator, dual water slides, a 695-foot lazy river, and a zero-entry pool. The resort also offers multiple swimming pools, private cabanas, a fitness center, full-service spa, on-site restaurants and bars, the Flip Flop’s Family Fun Center, and recreational activities on scenic Lake Austin. When not enjoying the residence, owners may participate in the professionally managed hotel rental program, subject to applicable terms and restrictions. The Grove is zoned as a condo-hotel, with owner occupancy limited to 179 days calendar year. This turnkey property combines a desirable location, exceptional amenities, and effortless vacation ownership in one of Central Florida’s most popular resort destinations.

14501 Grove Resort Ave, Winter Garden
$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
$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
Start Your Search