Winter Garden/Oakland Homes with Two Story Property Description

Winter Garden/Oakland Homes with Two Story Property Description

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant area is renowned for its charming historic downtown, lush landscapes, and a strong sense of community. With its picturesque streets lined with oak trees and delightful shops, residents enjoy a blend of small-town charm and modern conveniences. The area boasts a variety of outdoor recreational opportunities, including the scenic West Orange Trail and the beautiful lakes that dot the landscape, perfect for weekend picnics, biking, or leisurely strolls.

When it comes to finding your dream home, Winter Garden and Oakland offer a remarkable selection of two-story properties that cater to diverse lifestyles. These homes are designed with spacious layouts, providing ample room for families to grow and thrive. The two-story designs often feature open-concept living areas, modern kitchens, and inviting outdoor spaces, making them ideal for entertaining guests or enjoying quiet family evenings.

Imagine waking up in a beautifully appointed master suite, with sunlight streaming through large windows, and enjoying your morning coffee on a cozy balcony. Many of these homes also come equipped with energy-efficient features, ensuring comfort and sustainability.

With excellent schools, a variety of local dining options, and a strong sense of community, Winter Garden and Oakland are not just places to live; they are places to call home. Explore the possibilities of two-story living in this idyllic region and discover the perfect blend of comfort, style, and community spirit that awaits you.

Newest Winter Garden/Oakland Homes with Two Story Property Description

4 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Toll Brothers new construction in Winter Garden, Horizon West. Estimated completion in 2027. The Montpelier bungalow offers a thoughtfully designed layout with a covered entry leading to a spacious foyer and a private guest suite. The main living area features an open-concept design with a dining area, breakfast bar, great room, and access to the courtyard, creating a comfortable space for everyday living and entertaining. The second floor includes two secondary bedrooms and a private primary suite featuring a large walk-in closet and a well-appointed bath with dual vanities, separate shower, and private water closet. Additional highlights include the functional bungalow design, inviting courtyard space, and the opportunity to personalize select design features based on the stage of construction

13020 Sunset Garden Lane, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Toll Brothers new construction. The Autumn townhome offers 2,593 square feet of thoughtfully designed living space with 4 bedrooms and 4 bathrooms. An inviting foyer leads to a first-floor bedroom, ideal for guests, a home office, or flexible living. The open-concept floor plan seamlessly connects the kitchen, casual dining area, and great room, creating an ideal space for everyday living and entertaining. The kitchen features designer cabinetry, upgraded countertops, and a decorative tile backsplash. Upstairs, the private primary suite includes a spacious walk-in closet and en-suite bath, while two secondary bedrooms share a full bathroom. Additional highlights include a private rear courtyard, a detached 2-car garage with a versatile loft above that provides additional flexible living space for a home office, media room, fitness area, or playroom, and professionally selected finishes throughout. Residents enjoy access to resort-style community amenities.

12776 Sunset Walk Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to this beautifully designed new construction bungalow by Toll Brothers in the desirable Winter Garden/Horizon West area, with estimated completion in April 2027. A covered front entry welcomes you into a spacious foyer that opens to a versatile flex space, ideal for a home office or additional living area. The open-concept floor plan features a well-appointed kitchen with a breakfast bar overlooking the dining area and a great expansive room, creating the perfect setting for everyday living and entertaining. Enjoy seamless indoor-outdoor living with access to the private courtyard. The spacious primary suite offers a large walk-in closet and a luxurious bath complete with dual vanities, a separate shower, and a private water closet. Experience thoughtfully designed living in one of Central Florida's most sought-after communities.

13056 Sunset Garden Lane, Winter Garden

3 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to the Crowley townhome by Toll Brothers, located in the desirable Winter Garden/Horizon West area. This thoughtfully designed new construction home features a covered front entry that opens to a spacious, open-concept living area, seamlessly connecting the great room, kitchen, and dining space. Enjoy outdoor living in the private courtyard with convenient access to the detached 2-car garage. Above the garage, a finished loft with a full bathroom adds approximately 550 square feet of flexible living space, perfect for a guest suite, home office, fitness room, media room, or hobby space. The spacious primary suite offers a large walk-in closet and a well-appointed bath featuring dual vanities and a separate shower. Experience low-maintenance living with exceptional design in one of Central Florida's most sought-after communities.

12800 Sunset Walk Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to this stunning new construction home by Toll Brothers in the highly sought-after Winter Garden/Horizon West area, with estimated completion in April 2027. Designed with both everyday living and entertainment in mind, this thoughtfully crafted floor plan offers an open-concept great room, kitchen, and dining area that seamlessly flow together. A covered front entry welcomes you inside, while the covered lanai and spacious private courtyard create the perfect outdoor retreat with convenient access to the detached 2-car garage. The luxurious primary suite features a generous walk-in closet and a spa-inspired bath with dual vanities, a separate shower, and a private water closet. Don't miss this opportunity to own a beautifully designed new home in one of Central Florida's most desirable communities.

13038 Sunset Garden Lane, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code

Experience refined living in this exceptional 5-bedroom, 3-full and 2-half bath residence nestled in one of Winter Garden's most desirable communities. Thoughtfully designed with an open-concept floor plan, the expansive great room seamlessly connects to the gourmet kitchen, creating an inviting space for both everyday living and elegant entertaining. The first-floor primary suite offers a private retreat, complete with a spacious layout and spa-inspired bathroom. The primary bath connects to your California style closet and laundry room. Throughout the home, you'll appreciate upscale finishes, including designer lighting, elegant flooring, stone countertops, stainless steel appliances, and architectural details that elevate every space. New carpets and a new Kitchen Aid refrigerator installed in July 2026. Large windows fill the home with natural light, enhancing the bright and airy atmosphere. Four additional bedrooms located upstairs with jack and jill style bathrooms. This home has two bonus areas for maximum entertaining potential, comfort and functionality. This home is also equipped with a whole house water softener, Tesla charger and Govee lights. The backyard is set for entertainment with your summer kitchen, firepit and turf grass. Ideally located near premier shopping, dining, entertainment, parks, and top-rated schools, this home combines luxury, convenience, and timeless style in the heart of Winter Garden. A rare opportunity to own a beautifully appointed turn-key ready home in an exceptional location.

1664 Holcomb Creek St., Winter Garden

5 Beds ⋅ 5 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code

Stunning two-story house with a permanent lake view. Be enchanted by this magnificent lakefront residence, which combines sophistication, comfort, and a privileged location. It features 5 bedrooms, 4 full bathrooms, and 1 powder room, distributed in a smart and functional layout. The social area impresses with high ceilings in the living room and sliding doors that open onto a large covered veranda, integrated with a heated pool with a safety net, ideal for leisure and entertainment throughout the year. The living room is integrated with the dining room and the spacious and elegant gourmet kitchen, equipped with a generous central island, appliances, and wooden cabinets, perfect for those who enjoy entertaining. The master suite on the ground floor offers complete privacy, as well as relaxing views of the lake and green area, and a full bathroom on the same level. On the second floor, the house also features a versatile loft, ideal for an office, TV room, or social space. The space originally intended for a garage has been carefully adapted into a private gym, and can easily be converted back to suit the new owner's needs. Located in the desirable Hawksmoor community, the property offers complete infrastructure, including a community pool, gym, clubhouse, and walking paths. All this in a strategic location, close to markets, restaurants, shops, a theater, major highways, and Disney parks. A unique opportunity to live or invest. Schedule your visit and be amazed!

16394 Taliesin Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Porter floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Porter floor plan offers modern living tailored to meet everyday needs with style and functionality.

7276 Windy Willow Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or family gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Harbor floor plan offers modern living tailored to meet everyday needs with style and functionality.

7272 Windy Willow Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Encore/Ovation Ph 3 SubDv. ⋅ 34787 Zip Code

A Rare Opportunity in Encore at Ovation! This beautifully upgraded Jensen model is back on the market! Located just off Disney's Western Way, this exceptional home offers timeless designer finishes, an open-concept floor plan, and an unbeatable location just minutes from Walt Disney World. The stunning kitchen features 42-inch shaker cabinets, quartz countertops, an oversized island, dovetail drawers, and upgraded lighting. Waterproof wood-look flooring flows throughout the main level, while extra-height baseboards add a custom touch. The spacious primary suite includes a tray ceiling and a luxurious bath with a designer-tiled walk-in shower and semi-frameless glass enclosure. Bathrooms feature granite countertops and slate-look porcelain tile, with plush carpeting upstairs. A standout feature is the private backyard exclusive to this floor plan creating the perfect space to relax or entertain. Walt Disney World and Margaritaville Resort Orlando are both nearby, as well as premier shopping, dining, and entertainment. Don't miss this opportunity to own one of Encore at Ovation's most desirable homes. Schedule your private showing today!

13879 Lanyard Way, Winter Garden

6 Beds ⋅ 5 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Anna Maria with Bonus with 6 Bedrooms floorplan is a thoughtfully designed home featuring four bedrooms and two and a half bathrooms on the 1st floor and 2 additional bedrooms and 2 baths on the 2nd floor, along with a bonus room perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large walk-in closet. Additionally, the home includes a covered patio for outdoor enjoyment and a convenient two-car garage

17320 Wild Daisy Drive, Winter Garden

6 Beds ⋅ 5 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code

Virtually Staged. Pre-Construction. To be built. Anna Maria with Bonus Room: Welcome to this spacious, thoughtfully designed 6-bedroom, 4.5-bath home, offering the perfect blend of comfort and functionality. The heart of the home is the expansive kitchen, featuring a large center island that's ideal for cooking, entertaining, and gathering with friends. The private primary suite is conveniently located on the first floor, providing a peaceful retreat with added privacy. Upstairs, you'll find two generously sized bedrooms, each with access to it's own bathroom, along with a spacious game room that's perfect for movie nights, a play area, or a second living space.

17314 Wild Daisy Drive, Winter Garden

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