Winter Garden/Oakland Homes with City View

Winter Garden/Oakland Homes with City View

Welcome to Winter Garden and Oakland, two charming communities nestled in the heart of Orange County, Florida. Known for their rich history, vibrant culture, and stunning natural beauty, these areas offer a unique blend of small-town charm and modern conveniences, making them an ideal place to call home.

Winter Garden is famous for its picturesque downtown area, where historic buildings house delightful shops, restaurants, and cafes. The weekly farmers market is a local favorite, drawing residents and visitors alike to enjoy fresh produce, artisanal goods, and live entertainment. Meanwhile, the nearby Oakland community boasts serene landscapes, lush parks, and a close-knit atmosphere that fosters a sense of belonging.

One of the most appealing features of homes in this region is the breathtaking city view. Picture yourself unwinding after a long day, sipping your favorite beverage on a spacious balcony while taking in the stunning vistas of the Orlando skyline. Many properties in Winter Garden and Oakland are designed to maximize these views, with expansive windows and thoughtfully landscaped outdoor spaces that seamlessly blend indoor and outdoor living.

Whether you're seeking a cozy bungalow or a modern estate, the real estate options in Winter Garden and Oakland cater to a variety of tastes and budgets. With the area's excellent schools, proximity to major highways, and abundant recreational opportunities, it's no wonder that families and professionals are flocking to this thriving region. Embrace the charm and beauty of Winter Garden and Oakland—your dream home awaits!

Newest Winter Garden/Oakland Homes with City View

$560,000
4 Beds ⋅ 3 Baths ⋅ John Lake Pointe SubDv. ⋅ 34787 Zip Code
Motivated seller! 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
$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
$1,799,000
4 Beds ⋅ 5 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code
Experience the ultimate in luxury urban living at 68 N Park Ave, a stunning 3-story townhome with rooftop deck located in the heart of Historic Downtown Winter Garden. This sophisticated 4-bedroom, 4.5-bathroom residence offers over 3,500 sq. ft. of meticulously designed space, seamlessly blending modern elegance with the charm of the historic district. The open-concept main level features soaring 11-foot ceilings, expansive industrial-style windows, and a chef’s dream kitchen equipped with an oversized quartz island, natural gas appliances, and custom artisan cabinetry. Accessibility is effortless with your own private elevator serving all floors. Retreat to the third-floor master suite, featuring a spa-inspired bath and massive walk-in closet, or host guests in the versatile first-floor bedroom suite. The "wow factor" continues on the 1,200 sq. ft. private rooftop terrace, offering panoramic views of the city skyline—the perfect spot for evening cocktails or watching local fireworks.Location is everything. Leave your car in the 2-car garage and embrace the golf-cart-friendly lifestyle. You are just steps away from: The award-winning Winter Garden Farmers Market, The vibrant Plant Street Market and Crooked Can Brewing Co, The world-class West Orange Trail for biking and running, Boutique shopping, fine dining, and the historic Garden Theatre. Don’t miss this rare opportunity to own a piece of downtown luxury. Schedule your private showing today!

68 N Park Avenue, 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