Winter Garden/Oakland Homes with 2 Car Garage Garage Description

Winter Garden/Oakland Homes with 2 Car Garage Garage Description

Welcome to the enchanting region of Winter Garden and Oakland, Florida, where picturesque landscapes meet a vibrant community atmosphere. Nestled in the heart of Orange County, this charming area is renowned for its rich history, lush parks, and a plethora of recreational activities that cater to all ages. With its close-knit neighborhoods and a strong sense of community, Winter Garden and Oakland offer a perfect blend of suburban tranquility and urban convenience.

One of the standout features of homes in this region is the availability of properties with true 2-car garages. These spacious garages not only provide ample room for your vehicles but also offer additional storage space for tools, outdoor gear, or even a workshop for DIY enthusiasts. Imagine coming home to a beautifully designed residence that complements your lifestyle, complete with a garage that meets all your needs.

The homes in Winter Garden and Oakland are characterized by their diverse architectural styles, from charming bungalows to modern family homes, all set against the backdrop of stunning Florida landscapes. With easy access to top-rated schools, shopping, and dining options, residents enjoy the convenience of having everything they need just a stone's throw away.

Whether you're looking to settle down in a family-friendly neighborhood or seeking a vibrant community filled with activities and events, Winter Garden and Oakland have it all. Discover the joy of living in a region that perfectly balances comfort, convenience, and a true sense of belonging. Your dream home with a 2-car garage awaits you in this delightful corner of Florida!

Newest Winter Garden/Oakland Homes with 2 Car Garage Garage Description

$580,000
4 Beds ⋅ 2 Baths ⋅ Covington Park A B D E F G & J SubDv. ⋅ 34787 Zip Code
Welcome to 618 Bainbridge Loop, where thoughtful updates, flexible living space, and the Winter Garden lifestyle come together. This 4-bedroom, 2-bath home PLUS a dedicated office features a desirable split-bedroom floor plan, while maintaining an open-concept layout that’s perfect for entertaining and everyday living. The renovated kitchen serves as the heart of the home, while the updated guest bathroom and renovated patio add even more move-in-ready appeal. The office features brand-new flooring, creating the perfect space for working from home, a playroom, or additional flex space. Major updates have already been taken care of with a 2023 roof, 2022 A/C, 2025 water heater, and 2024 appliances. Step outside to the refreshed patio, ready for morning coffee, weekend gatherings, or unwinding at the end of the day. Located within the Winter Garden golf cart district and near highly regarded local schools, this home offers a location that’s just as appealing as the home itself. With its combination of updates, functional layout, and sought-after Winter Garden lifestyle, 618 Bainbridge Loop is ready to welcome you home.

618 Bainbridge Loop, Winter Garden
$369,500
3 Beds ⋅ 3 Baths ⋅ Stoneybrook West Unit 8 SubDv. ⋅ 34787 Zip Code
Welcome to Westbrook at Stoneybrook West, a well-established townhome community in the heart of Winter Garden! This spacious 3-bedroom, 2.5-bath townhome offers 1,650 square feet of comfortable living space along with an attached 2-car garage. The main level features an open living and dining area, while all three bedrooms are conveniently located upstairs, including a spacious primary suite with a private bath and walk-in closet. A covered outdoor patio provides additional space to relax and enjoy the Florida weather. The home is currently being refreshed with new interior paint and new flooring throughout, allowing the next owner to move in and enjoy a clean, updated space from day one. Westbrook offers residents a community pool, playground, sidewalks, and plenty of guest parking, all in a location that puts everyday conveniences close by. Publix, Walgreens, restaurants, and shopping are just minutes away, with Winter Garden Village and Historic Downtown Winter Garden also within easy reach. Spend the weekend exploring the brick-lined streets of Plant Street, visiting the Saturday Farmers Market, or enjoying miles of biking and walking along the West Orange Trail. With convenient access to SR-429, SR-50, and Florida’s Turnpike, commuting throughout Central Florida, Downtown Orlando, the airport, and the theme parks is a breeze. Enjoy low-maintenance townhome living in one of Winter Garden’s most convenient locations — schedule your private showing today!

1327 Priory Circle Unit 1327, Winter Garden
$350,000
2 Beds ⋅ 3 Baths ⋅ Signature Lks-Pcl 01a SubDv. ⋅ 34787 Zip Code
Welcome to this charming and spacious 2-bedroom, 2.5-bath town-home located in the highly sought-after Signature Lakes / Independence Community. This beautifully designed town-home features an open-concept floor plan that seamlessly connects the kitchen and family room, creating a bright and inviting living space. Upstairs, both bedrooms feature en-suite bathrooms for maximum privacy, with the oversized owner’s suite boasting a luxurious bath and a walk-in closet. The exterior of the home features a fenced paver patio in the backyard, providing a private outdoor retreat that connects to the detached two-car garage. Residents of Signature Lakes enjoy access to exceptional amenities, including two clubhouses with resort-style pools, fitness centers, tennis courts, basketball courts, and playgrounds. The community also offers boat ramps, scenic parks, nature trails, a business center, a community room, and well-maintained green spaces, creating the perfect setting for an active and vibrant lifestyle. Beyond its impressive amenities, Independence is known for its dynamic community atmosphere, enhanced by dedicated community event organizers who plan a variety of immersive events throughout the year. Residents enjoy seasonal festivals, fireworks displays, and food truck gatherings, fostering a true sense of connection and entertainment. Located just minutes from Walt Disney World, Universal Studios, and other major attractions, this town-home offers a unique blend of comfort, convenience, and resort-style living. Schedule your showing today!

14448 Pleach Street, Winter Garden
$419,999
3 Beds ⋅ 3 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code
Storey Grove ** 2023 built ** Open floorplan **BACKS TO GREENSPACE!!** Beautiful wood ceramic tile entire 1st floor ** Attractive tv wall wood accent inlay in the family room ** White kitchen cabinetry with quartz counters and large cooking island ** All bedrooms are on the 2nd floor ** Nice size +/-16x20 brick paver patio area and 2 car detached garage ** Great RING security system, RING cameras, doorbell and door and window sensors ** Tesla EV power outlet is already in place in the garage ** Overhead storage racks in the garage are included ** Storey Grove community amenities include a huge resort style community pool, fitness center, basketball courts, children's playground and green space area. Room measurements are from builder floor plan. Buyers to verify all room measurements.

10648 Words Drive, Winter Garden
$560,000
4 Beds ⋅ 4 Baths ⋅ Storey Grove Ph 1b-3 SubDv. ⋅ 34787 Zip Code
This beautiful 4 bedroom, 3 1/2 bath home features an open layout with designer finishes that are light and bright throughout. There are 2 master bedroom one on the first floor and in the second floor Perfect for families. Large great room downstairs, bonus room/loft upstairs with vaulted ceiling and a beautiful backyard. Upgraded just like the model. Quartz counter top throughout, upgraded light cabinets, wood plank, tile floor. Upgraded GE Profile appliances and complete Smart Home Package with smart thermostats, smart switches Wireless range extenders built in Alexa smart home controls. Storey Grove is beautiful picturesque community with pool, fitness center, parks, playgrounds and more. It's a perfect location just minutes from Disney, Shopping, Dining, New Hamlin retail and theaters, Easy Access to 429 Expressway, and zoned for A rated schools . Come and check personally .

15163 Book Club Road, Winter Garden
$450,000
3 Beds ⋅ 2 Baths ⋅ Corsino Place SubDv. ⋅ 34787 Zip Code
Set on a quiet cul-de-sac near the heart of Winter Garden, this updated single-story home pairs an easy, open layout with an unusually spacious backyard. Inside, 3 bedrooms and 2 bathrooms are arranged across 1,307 square feet, with vaulted ceilings and ceramic tile connecting the kitchen, dining area, and living room. The refreshed kitchen features white cabinetry, quartz countertops, a glossy subway-style backsplash, a deep undermount sink with a pull-down faucet, modern lighting, and a peninsula with breakfast-bar seating. Sliding glass doors extend the living space directly to the backyard. The primary suite offers tile flooring, a feature wall, private patio access, an en-suite bath, and a true walk-in closet. Two additional bedrooms and a second full bath provide flexible space for guests, an office, or everyday living. Fresh interior paint, updated light fixtures, ceiling fans, and a functional split-bedroom design complete the interior. Outside, the fully fenced 0.23-acre lot is a standout. A roofed pergola creates a generous shaded patio and room for outdoor dining and lounging. Beyond it, the broad lawn leads to a defined circular firepit area and a 10-by-20 storage shed, with ample open space for recreation, gardening, and outdoor hobbies. Aerial views highlight the depth and usability of the yard, while the attached two-car garage adds everyday storage and convenience. With no HOA and no CDD, the property offers flexibility in an established neighborhood close to the West Orange Trail, local parks, Lake Apopka, and the shops, dining, Plant Street Market, and brewery district of downtown Winter Garden. Enjoy an evening downtown, a weekend bike ride, or a relaxed night around the backyard firepit, all from a well-located home with room to make it your own.

1312 Corsino St, Winter Garden
$635,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated community of Stoneybrook West. Offering over 2,800 square feet of living space, this home combines a spacious and flexible floor plan with a fantastic setting overlooking the 6th hole and no rear neighbors. Recent improvements include a newer roof and A/C, fresh exterior and interior paint, renovated kitchen, bathrooms, and flooring. The main level offers multiple living and dining spaces, while the kitchen features stone countertops, stainless steel appliances and abundant cabinetry. Upstairs, the spacious primary suite includes a tray ceiling, walk-in closet and private bath with dual vanities and a beautifully remodeled walk-in shower. The oversized loft provides plenty of flexibility for a second living area, media room, playroom or home office. Step outside to a large backyard with expansive golf course views and plenty of room to enjoy the outdoor living. Stoneybrook West offers an impressive collection of amenities, including a community pool, golf, clubhouse, tennis and basketball courts, playgrounds and walking paths. Ideally located near Winter Garden Village, historic Downtown Winter Garden, shopping, dining and major roadways, this home offers a great combination of space, improvements, amenities and community.

15081 Masthead Landing Circle, Winter Garden
$825,000
4 Beds ⋅ 3 Baths ⋅ Overlook At Hamlin SubDv. ⋅ 34787 Zip Code
Welcome to 5743 Thomas Square Drive, an exceptional single-story pool home located in the lakefront community of The Cove at Hamlin in Winter Garden. Built in 2018, this beautifully upgraded Jamestown model offers 4 bedrooms, 2.5 bathrooms, 2,917 square feet, and a thoughtfully designed split floor plan that combines comfort, style, and effortless Florida living. Inside, engineered hardwood floors, custom archways, high ceilings, and abundant natural light lead into an expansive open-concept living space. The kitchen serves as the heart of the home with quartz countertops, stainless steel appliances, generous cabinetry, and seamless flow into the dining and living areas. One of the home's most impressive features is the massive owner's suite. Offering an exceptional amount of space rarely found in homes of this size, the suite easily accommodates a full bedroom setup with room for a sitting area, additional furnishings, or a private retreat within the room. A spacious owner's bath and generous custom closet complete the suite, while three additional bedrooms provide flexibility for family, guests, or a home office. Step outside to an extended screened lanai overlooking the private saltwater pool and beautifully landscaped fenced backyard. Solar and natural gas pool heating, built-in lighting, a fire pit, and a gas connection for an outdoor grill create a backyard designed for entertaining and enjoying the Florida lifestyle year-round. Lake views complete the setting, along with the opportunity to enjoy nightly Disney fireworks from home. Beyond the home, one of the biggest draws is the incredible Hamlin lifestyle just minutes from your front door. Spend an evening putting at PopStroke, catch a movie from a luxury recliner at Cinépolis, grab dinner at Ford's Garage or Agave Bandido, meet friends at Home State Brewing Co., or start the morning with coffee and breakfast at Toastique. Hamlin continues to offer an exciting mix of restaurants, entertainment, shopping, fitness, community events, and everyday conveniences, making it easy to enjoy a night out without traveling far from home. The Cove at Hamlin offers its own impressive collection of amenities, including a resort-style community pool, clubhouse, fitness center, splash pad, playgrounds, dog park, walking trails, outdoor gathering spaces, and private access to Lake Hancock with a community boat ramp and dock. With easy access to SR 429, Walt Disney World, Hamlin Town Center, and everything Horizon West has to offer, 5743 Thomas Square Drive is more than a beautiful pool home. It offers the opportunity to live in the heart of one of Central Florida's most exciting and rapidly growing communities.

5743 Thomas Square Drive, Winter Garden
$499,999
3 Beds ⋅ 3 Baths ⋅ Watermark SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained home in the highly sought after Watermark at Horizon West community! This spacious two story residence offers 3 bedrooms, 2.5 bathrooms, and over 2,000 square feet of thoughtfully designed living space. The open concept floor plan is perfect for both everyday living and entertaining, featuring wood tile flooring throughout the main level, abundant natural light, and a modern kitchen complete with built in appliances, ample cabinetry, generous counter space, and a large island overlooking the living and dining areas. Upstairs, you'll find a versatile loft that makes an ideal home office, media room, or play area, along with a spacious primary suite featuring a walk in closet and an en-suite bath. Two additional bedrooms, a full bath, and an upstairs laundry room complete the second floor. Enjoy Florida living from the welcoming front porch while taking advantage of the home's rear entry two car garage and low maintenance yard. Residents of Watermark enjoy resort style amenities including a community pool, fitness center, tennis courts, playground, parks, walking trails, and beautifully maintained common areas. You’re also within close distance to restaurants and just a short drive to Disney, shopping, and everything Winter Garden and Horizon West have to offer. If you’re looking for a clean, move in ready home in a great location with a strong lifestyle, this one checks all the boxes!

14543 Golden Harbor Lane, Winter Garden
$415,000
3 Beds ⋅ 3 Baths ⋅ Hawksmoor SubDv. ⋅ 34787 Zip Code
Priced to sell! Great location and highly desired community! Located in the highly sought-after Hawksmoor community in Winter Garden, this beautifully maintained townhome offers exceptional value and an incredible lifestyle. The location is unbeatable, close to top-rated schools, major highways, shopping, dining, and world-class theme parks. Situated just minutes from Hamlin, you’ll enjoy easy access to one of Central Florida’s most dynamic and fast-growing areas, with a wide variety of shopping, dining, and entertainment options, including Publix, Cinépolis Luxury Cinemas, and popular restaurants. Hawksmoor offers an impressive selection of top-tier amenities, including a resort-style zero-entry pool, splash pad, shaded pavilion, clubhouse with outdoor kitchen, fitness center, scenic walking trails, yoga lawn, and multiple playgrounds and parks. The community also provides quick access to the 429 expressway, making commutes to Downtown Orlando, Walt Disney World, and other major attractions convenient and easy. The property is currently tenant occupied, with the tenant in place since October 2025, making this an excellent opportunity for investors looking for a property in a highly desirable and growing area. Priced to sell! Don’t miss the opportunity to own a townhome in one of Winter Garden’s most desirable communities. This is more than a home—it’s a lifestyle!

16306 Prairie School Drive, Winter Garden
$610,000
5 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 1b SubDv. ⋅ 34787 Zip Code
Beautiful 4 bedroom 2 1/2 bath home with a 2 car garage. Features a formal living area, combo family and formal dining area off the kitchen, the patio has been enclosed and has air conditioning, a loft area on the second floor. tile floors on the first floor and hardwood floors on the second floor. Located in Summerlake – a LIFESTYLE COMMUNITY with Pool, Clubhouse, Fitness Center, Playground, Zip Line, Dog park, Tennis and Basketball Courts. RELAX. All this close to DISNEY, ORANGE COUNTY GOLF COURSE, LUXURY CINEMAS, SUPERMARKET, SHOPPING and RESTAURANTS. Plus zoned for Summerlake Elementary, Hamlin Middle and Horizon High School! Easy Access to 429 and 408!

8111 Pacific Loon Street, Winter Garden
$659,310
4 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12325 Silk Mimosa Alley, Winter Garden
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