Winter Garden/Oakland Homes with 2 Car Garage Garage Description

Winter Garden/Oakland Homes with 2 Car Garage Garage Description

Welcome to the charming communities of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This picturesque region is renowned for its vibrant downtown area, rich history, and stunning natural landscapes. With its lush greenery, scenic parks, and beautiful lakes, Winter Garden offers a delightful blend of suburban tranquility and urban convenience, making it an ideal place for families and professionals alike.

One of the standout features of homes in this area is the availability of properties with two-car garages. These spacious garages provide ample room for vehicles, recreational equipment, and additional storage, catering to the needs of today’s busy households. Imagine returning home after a long day, pulling into your driveway, and parking your car in a secure, spacious garage that not only protects your vehicle from the elements but also offers the convenience of direct access to your home.

The homes in Winter Garden and Oakland are designed with modern living in mind. Many feature open floor plans, contemporary finishes, and outdoor spaces perfect for entertaining or relaxing with family. The nearby historic downtown Winter Garden is brimming with charming shops, delightful eateries, and a vibrant farmers’ market, creating a welcoming atmosphere that fosters community spirit.

Whether you’re seeking a cozy family home or a stylish retreat, the homes with two-car garages in Winter Garden and Oakland are sure to meet your needs. Experience the perfect blend of comfort, convenience, and community in this beautiful corner of Florida. Embrace the lifestyle you’ve always dreamed of in Winter Garden and Oakland!

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

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

3 Beds ⋅ 3 Baths ⋅ Deer Island SubDv. ⋅ 34787 Zip Code

Welcome home! This turnkey, exquisite custom home enables you to wake up to shimmering water views of Johns Lake and step into the lakefront lifestyle you’ve been dreaming of. On an acre in a gated community, sellers spared no expense on a complete renovation— exterior to interior and down to the studs. New windows, high end finishes, and designer details in every room rival new construction. Upon entering, you’ll be captivated by an abundance of natural light, soaring ceilings and panoramic water views. The foyer leads to the spacious living/office/flex space and dining room with stunning dry bar and 180+ bottle wine fridge. The large family room with fireplace feature wall and bay window adjoins the true gourmet kitchen for open concept living, overlooking the lake and community pond with lighted fountain. A chef’s kitchen features tall kitchen cabinets for extra storage, massive center island, large sink, Fisher and Paykel double-drawer dishwasher, Scotsman pellet icemaker. The all Viking appliance pkg includes a 36” refrigerator with 30” freezer, dbl ovens, warming drawer, 6 burner induction stove top. A plumbed, built-in Miele espresso machine provides your favorite morning coffee, hot water, and more. A reverse osmosis water filtration system feeds the kitchen sink, icemakers, coffee machine. The sunroom boasts two walls of new Pella hurricane rated slider doors that flood the home with natural light and frame the stunning waterfront scenery and provides a seamless connection between indoor and outdoor living opening onto the sandstone lanai with oversized resort style sparkling saltwater pool, spa and waterfall. The lanai roof structure is unique in that the vaulted roof and screening provides all weather protection to the pool, built in bar and overflow patio area allowing for entertaining in any weather or watching the Disney fireworks or rocket launches. The lanai is outfitted with 3 large DC ceiling fans and integrated watering system. Spacious primary bedroom with lanai access overlooks the lake and boasts a spa-like bathroom with dual vanities, frameless zero entry shower, free-standing tub and large walk-in closet. The split bedroom plan allows for maximum privacy. Secondary bedrooms are spacious with oversized closets. The exterior, with its professional landscape design and lighting, is designed for play, relaxation and beauty. Enjoy direct access to Johns Lake and spend your days boating, jet skiing, kayaking, paddle boarding, fishing or simply relaxing. A paver walkway from the house leads to the expansive back yard, beachfront, and large fire pit area, perfect for play and entertaining. Private dock with remote boat lift and double jet ski lift allows for lake enjoyment with effortless access. Dock is equipped with running water, lights and no/low maintenance composite decking and handrails. The deep garage is oversized with storage racks and an additional air-conditioned bonus space to be used as a craft/exercise room/home office or air-conditioned storage. Neighborhood amenities include community dock, boat ramp, tennis/pickleball court, basketball court, cable/internet. Conveniently and centrally located with easy access to the Turnpike, 429, 408, downtown Winter Garden and Orlando, the airport, Disney, Universal and area attractions. Minutes to restaurants, shops, hospitals, West Orange Trail. Link to interactive floor plan: https://www.zillow.com/view-imx/6a573be4-fd0d-4649-9df8-88349b2426f6?initialViewType=pano

263 Deer Isle Drive, 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

3 Beds ⋅ 3 Baths ⋅ Winding Bay SubDv. ⋅ 34787 Zip Code

Located in the desirable Winding Bay community in Horizon West, this impeccably maintained home offers 3 spacious bedrooms, 2.5 bathrooms and a versatile flex room that can easily serve as a home office, playroom or potential 4th bedroom. Luxury tile flooring, upgraded in 2025, flows throughout the entire home for a clean and consistent look that is stylish, durable and easy to maintain. The kitchen serves as the centerpiece of the main living space, featuring an oversized island, custom range hood, upgraded cabinetry with crown molding, hard-wired under-cabinet lighting and abundant counter and storage space. Crown molding, oversized baseboards, decorative columns, and custom finishes bring an elevated feel and distinctive detail to the interior. The spacious owner’s suite features plantation shutters and a beautiful en-suite bathroom, fully upgraded in 2026 with floor-to-ceiling tile, modern finishes and a large walk-in closet. The two secondary bedrooms share a convenient Jack-and-Jill bathroom. Double sliding doors lead to the screened lanai with sun shades, overlooking the fully fenced backyard with iron fencing. In the evening, relax outdoors and enjoy views of the Disney fireworks in the distance, adding a special touch to the Florida lifestyle. Additional features include an extended driveway with pavers, gutters, whole-home security camera system, whole-home water softener, reverse osmosis filtration in the kitchen and a dedicated garage outlet for an additional refrigerator or freezer. Solar panels provide an added energy-efficiency benefit, with electric bills averaging approximately $34 during the hot summer months. With no carpet, extensive upgraded tile flooring, flexible living space, a renovated owner’s bathroom, solar panels, and numerous thoughtful upgrades, this Horizon West home is truly move-in ready. This home offers convenient access to shopping, dining, schools, major roadways, and the many amenities throughout Winter Garden and West Orange County. Schedule your showing today!

10750 Petrillo Way, Winter Garden

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

Situated in the sought-after Waterleigh community, one of the most popular communities in Horizon West/Winter Garden this stunning 3-bedroom, 2-bathroom home offers the perfect blend of comfort, style, and convenience. This home is perfect for those seeking a tranquil and inviting living environment. Upon entering, you'll be greeted by a warm and inviting atmosphere that flows throughout the entire home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a space that is perfect for both everyday living and entertaining. The kitchen features modern appliances, ample counter space, and a great circulation area. You will love cooking in the well-appointed kitchen with stainless steel appliances, a walk-in pantry, and an ample island w/ bar top seating that is perfect for gatherings. The kitchen has a WATER FILTRATION SYSTEM; system running to the fridge and a separate water faucet on the island. Whether you're preparing a quick meal or hosting a dinner party, this kitchen is sure to impress. The adjacent dining area is spacious and offers a lovely backdrop for enjoying meals with family and friends. The master suite offers privacy as it is separate from the other rooms located in the home, complete with a spacious bedroom, a walk-in closet, and an In-suite bathroom. The additional bedrooms are well-appointed, providing comfort and convenience for family members or guests. The home offers a large laundry room and a drop zone area situated next to the two-car garage perfect for your keys, tools, shoes…etc…. Located just minutes from DISNEY, in a family-friendly, GOLF CART FRIENDLY community, The owners of this home have access to a range of RESORT STYLE amenities, including 2 clubhouses with 2 beautiful large pools, a splash pad, 2 fitness centers with play area, miniature golf, beach volleyball, tennis, lake view BBQ/picnic area, dog-park, community dock, water-view walking trails. Location benefits include conveniently at the entrance of the community a new Publix shopping center, near Highway 429, and Highway 192, restaurants, and shopping at Flamingo Crossings, Hamlin, and Winter Garden Village. All lawn maintenance is provided through the community..... THE HOUSE HAS SOLAR PANELS. The seller will pay on the day of closing the debt he currently has with the solar panel financier. In this way, the Buyer has an ADDITIONAL DISCOUNT on the purchase of the property.

9456 Komika Lane, Winter Garden

3 Beds ⋅ 4 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code

Downtown Winter Garden becomes part of everyday life at this one-of-nine residence at 30 North Park, where a covered balcony overlooks the West Orange Trail and Plant Street’s dining, shops, and gathering spots are only a short stroll away. Arranged across three thoughtfully designed levels, the home balances connected gathering spaces with room to work and unwind. The main level brings the kitchen, dining area, and living room together beneath tall ceilings. An oversized island anchors the kitchen, complemented by quartz countertops, tall two-tone cabinetry, stainless steel appliances, and natural-gas cooking. Decorative wood beams, built-ins, and a gas fireplace feature wall give the living room character, while sliding glass doors extend the space to the balcony. Each of the three bedroom suites includes a walk-in closet and private full bathroom. Two suites occupy the upper level, including the primary with fitted closet storage, dual sinks, a glass-enclosed shower, and a separate water closet, while the second-level suite is currently arranged as a window-lined office. A ground-level bonus room with an adjoining fourth full bath creates another adaptable space for media, fitness, hobbies, or guests. Engineered hardwood and designer tile keep the interior carpet-free, while upper-level laundry, a tankless water heater, zoned HVAC, spray-foam ceiling insulation, and an attached rear-entry two-car garage add practical convenience. From quiet time on the balcony to mornings on the trail and evenings along Plant Street, this home pairs polished, flexible interiors with a distinctly downtown Winter Garden lifestyle.

72 N Park Avenue Unit 8, 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

4 Beds ⋅ 3 Baths ⋅ Horizon Isle SubDv. ⋅ 34787 Zip Code

WALK ON IN AND CALL IT HOME! Welcome to this beautiful, almost-new K. Hovnanian home, where thoughtful design, spacious living, and stylish upgrades come together beautifully. As you enter, you’re greeted by a welcoming foyer. To the right are two generously sized bedrooms and a full bathroom. Continue down the hall and discover a functional nook that’s perfect for a home office, study area, or homework station. With its own charming barn door, this space can easily be closed off for added privacy. Just to the right, French barn doors open to a versatile flex space that can be used as an office, formal dining room, or even a fourth bedroom—whatever best suits your lifestyle. Step into the spacious great room and prepare to be impressed! Gorgeous exposed beams create a warm and inviting atmosphere, while the chef-inspired kitchen is the true centerpiece. Featuring ample counter space, a beautiful white farmhouse sink, built-in oven, freestanding oven, stylish range hood, and stunning backsplash, this kitchen is both functional and beautifully appointed. The oversized primary suite offers a peaceful retreat, with a spacious bedroom and a luxurious ensuite bathroom designed with comfort in mind. Enjoy a large walk-in shower, freestanding soaking tub, dual vanities, and an enormous walk-in closet. This thoughtfully designed home also features a generously sized laundry room and mudroom, an oversized garage, and a beautiful lot with a fully fenced backyard—perfect for entertaining, relaxing, or enjoying time outdoors. And the location is just as impressive! Zoned for highly desirable schools and conveniently located near the 429, Turnpike, and 408, with easy access to Disney, shopping, dining, and so much more. With its spacious layout, beautiful finishes, and fantastic location, this home is sure to impress. Schedule your private showing today before this one is SOLD!

13184 Dendy Way, 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

3 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

Welcome home to a place where life feels just a little easier. Tucked inside the peaceful Westbrook community of Winter Garden, this beautifully maintained, move in ready townhome offers the perfect blend of comfort, style, and convenience. Step inside to discover an inviting open living and dining space that naturally brings everyone together. The heart of the home is the kitchen, thoughtfully designed with gleaming granite countertops, stainless steel appliances, a contemporary tile backsplash, and plenty of space to prepare everything from quick weekday breakfasts to weekend gatherings with friends. Stylish upgraded lighting throughout adds a fresh, modern touch to every room. Upstairs, all three bedrooms create a private retreat away from the main living areas. The spacious primary suite is designed for relaxation and features dual walk in closets, giving everyone room to stay organized. With two additional bedrooms and two and a half bathrooms, there's plenty of flexibility for family, guests, or a dedicated home office. Behind the scenes, a newer high efficiency HVAC system with a UV germicidal light provides year round comfort and added peace of mind. Outside your front door, you'll love being just minutes from Winter Garden Village, the award winning shops and restaurants of Historic Downtown Winter Garden, and the excitement of Disney Springs. Easy access to SR 429 puts Orlando, Tampa, and Central Florida's top attractions within easy reach, making both your daily commute and weekend adventures effortless. Beautiful, meticulously cared for, and ideally located, this is more than a townhome. It's the beginning of your next chapter. Schedule your private showing today.

1017 Priory Circle, Winter Garden

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