Winter Garden Homes with Two Story Style

Welcome to a home where thoughtful design, elevated finishes, and effortless Florida living come together. This exceptional 5-bedroom, 3.5-bath residence offers an impressive blend of space, functionality, and custom detail, complete with a bonus room, private office, formal dining room, spacious living room, and a stunning great room that truly serves as the heart of the home. Primary bedroom is located on the first floor offering a split floor plan and privacy. This is a smoke free, pet free home. Interior laundry room with utility sink. The great room seamlessly opens to the expansive kitchen, featuring generous cabinetry, abundant storage, and a comfortable eat-in space designed for everyday gatherings. Custom built-ins, an electric fireplace surrounded by beautiful stone, and ceiling speakers create an inviting atmosphere for both relaxing and entertaining. Throughout the home, Pottery Barn curtain rods, crown molding, upgraded lighting, and an abundance of closet and storage space showcase the attention to detail. Fresh interior paint adds a crisp, move-in-ready feel, while the custom-built office provides an ideal space for working from home. Upstairs, an upgraded wrought-iron staircase creates a striking architectural focal point while adding a sophisticated touch to the home's aesthetic. The versatile bonus room offers additional space for a media room, playroom, fitness area, or second living space—the possibilities are endless. Step outside through the double-sided sliders to your own private retreat. The screened and covered lanai overlooks a sparkling saltwater pool with a sheer-fall water feature, creating the perfect setting for Florida afternoons and beautiful sunsets to top off the evening entertaining possibilities. The outdoor living area is thoughtfully pre-wired for television and equipped for speaker connectivity, making it easy to create the ultimate outdoor entertainment space. The home also delivers an impressive list of functional upgrades, including a kitchen faucet reverse osmosis system, water softener, whole-house surge protector, newer water heater (2024) ,new exterior paint (2026) new windows (2022-23), and a new HVAC (1/26) system with a damper system and remote-control capability thermostat. A spacious 3-car garage and elegant paver driveway provide both convenience and curb appeal. A transferable termite bond (Massey) adds another layer of confidence for the next homeowner. Located within a gated community, residents enjoy added peace of mind along with an outstanding selection of amenities, including a playground, tennis and pickleball courts, soccer field, and picnic area. Beyond the community, Winter Garden offers an exceptional lifestyle with an abundance of dining, shopping, entertainment, and recreation options. Convenient access to 429, the Florida Turnpike, OIA 33 miles, and 535 makes commuting throughout Central Florida a breeze.

2202 Redmark Lane, Winter Garden

$675,000

3 Beds ⋅ 3 Baths ⋅ O6428431 MLS

Seller may consider buyer concessions if made in an offer ~ LIKE-NEW LIVING in one of Winter Garden’s most sought-after communities! Just four years old, this beautiful DAVID WEEKLEY SUMMERTON MODEL is located in McKinnon Square within award-winning Oakland Park – and the GOLF CART IS INCLUDED! High ceilings, abundant natural light and an OPEN CONCEPT design create a bright, welcoming interior made for everyday living and entertaining. At the heart of the home, the GOURMET CHEF’S KITCHEN flows seamlessly into the main living and dining spaces, while the inviting FRONT PORCH adds to the neighborhood feel Oakland Park is known for. All of the bedrooms are upstairs along with a versatile BONUS/LOFT offering endless possibilities as a home office, playroom, media space or second living area. Life here extends well beyond the front door – Oakland Park is a GOLF CART-FRIENDLY COMMUNITY offering a clubhouse, COMMUNITY POOLS, parks, playgrounds, a dog park and recreational amenities, plus easy access to the WEST ORANGE TRAIL and LAKE APOPKA. Cruise by golf cart to HISTORIC DOWNTOWN WINTER GARDEN for award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, seasonal festivals and the popular Winter Garden Farmers Market. Everyday convenience is equally impressive, with the elementary school approximately .5 miles away, middle school 1.1 miles, high school 3 miles and Orlando Health Hospital approximately 1.8 miles away. Hamlin Town Center, SR-429, SR-50 and Florida’s Turnpike are easily accessible, with shopping, dining, Disney and Central Florida attractions within reach. MOVE-IN READY, nearly new and complete with a golf cart, this Oakland Park home delivers the lifestyle that makes Winter Garden such a desirable place to call HOME!

923 Colie Alley, Winter Garden

$1,085,669

5 Beds ⋅ 4 Baths ⋅ O6435672 MLS

Under Construction. .

12528 Gold Honeysuckle Street, Winter Garden

$475,000

3 Beds ⋅ 3 Baths ⋅ O6435567 MLS ⋅ 00 BLDG.

Virtually Staged. Welcome Home to 15163 Orange Harvest Drive! YOUR oportunity to live in this incredible neighborhood, is HERE! Move-in ready and beautifully maintained, this townhome offers 3 bedrooms, 2.5 baths, and a bright, open layout perfect for modern living. A paver driveway and charming stucco exterior with mature landscaping set the tone before you even step inside. The main level features a spacious open-concept living and dining area with tile flooring throughout. Sliding glass doors lead out to a private patio, offering a peaceful spot to unwind while overlooking green common space. The kitchen is a standout, showcasing rich espresso cabinetry, gleaming granite countertops, a designer mosaic tile backsplash, stainless steel appliances, and a large island with pendant lighting — ideal for entertaining or casual family meals. Upstairs, the generously sized primary suite includes plush carpet and an en-suite bath with dual sinks, a walk-in shower, and a linen closet. A second full bath serves the additional bedrooms with a dual-sink vanity and a tub/shower combo, and a convenient half bath is located on the main level for guests. As part of a sought-after community, residents enjoy resort-style amenities including a sparkling community pool, tennis courts, a playground, and scenic lakefront views — all just minutes from Winter Garden's shops, dining, and amazing schools. Don't miss your chance to own this stylish, low-maintenance townhome in one of Winter Garden's most desirable communities!

15613 Orange Harvest Loop, Winter Garden

$424,990

3 Beds ⋅ 3 Baths ⋅ O6435583 MLS ⋅ 0659 BLDG.

Under Construction. Waterleigh presents the Ibis. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with an open concept a spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage and powder room at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As you head up to the second floor you are greeted with all 3 bedrooms and 2 bathrooms. The bedroom one suite impresses with double bowl vanity, walk in closet and spacious shower space. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Ibis includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16516 Barbours Creek Way, Winter Garden

$447,500

3 Beds ⋅ 3 Baths ⋅ O6435580 MLS ⋅ 0658 BLDG.

Under Construction. Waterleigh presents the Ibis. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with an open concept a spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage and powder room at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As you head up to the second floor you are greeted with all 3 bedrooms and 2 bathrooms. The bedroom one suite impresses with double bowl vanity, walk in closet and spacious shower space. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Ibis includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16510 Barbours Creek Way, Winter Garden

$359,999

3 Beds ⋅ 3 Baths ⋅ O6434246 MLS

Some photos are Virtually Staged. WELCOME to a HOME that truly stands out in THE ORCHARD, a desirable GATED COMMUNITY in WINTER GARDEN! This beautifully updated 3-BEDROOM, 2.5-BATHROOM TOWNHOME is perfectly positioned with NO REAR NEIGHBORS and a BEAUTIFUL OPEN GREEN SPACE BEHIND THE HOME, offering a peaceful and private setting. From the moment you arrive, the inviting PRIVATE ENTRYWAY and spacious ATTACHED 2-CAR GARAGE set the tone for the comfort and convenience this home offers. Step inside to discover NO CARPET ON THE FIRST FLOOR, UPDATED LAMINATE FLOORING, and numerous recent updates throughout. The home features NEW LIGHT FIXTURES AND CEILING FANS (2026), NEW FAUCETS (2026), and NEW CARPET UPSTAIRS (2026). Major systems have also been thoughtfully updated, including a NEW HVAC SYSTEM (2025) and ROOF (2020). The WASHER AND DRYER (2024) add even more value and convenience. The open-concept main living area seamlessly connects the living room, dining area, and kitchen, creating a warm and welcoming space for both everyday living and entertaining. The kitchen features GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, ABUNDANT CABINETRY, a LARGE WALK-IN PANTRY, and a BREAKFAST BAR WITH PENDANT LIGHTING. A versatile FLEX ROOM just off the main living area provides endless possibilities and can easily serve as a HOME OFFICE, PLAYROOM, EXERCISE ROOM, OR ADDITIONAL SITTING AREA. A convenient HALF BATH WITH UPDATED FIXTURES, large storage closet, and direct access to the garage complete the first floor. A DEDICATED LAUNDRY AREA adds even more convenience to the home’s thoughtful design. From the dining area, sliding glass doors open to the PEACEFUL BACKYARD SETTING, where you can relax and enjoy the expansive green space and the added privacy of NO REAR NEIGHBORS. Upstairs, the NEW CARPET INSTALLED IN 2026 continues into the spacious loft, currently used as an office and complemented by additional cabinetry. The generous PRIMARY SUITE features a MASSIVE WALK-IN CLOSET WITH A WINDOW and a private ensuite bathroom offering DUAL SINKS, a STANDING SHOWER, SEPARATE JETTED SOAKING TUB, and PRIVATE WATER CLOSET. Two additional bedrooms are thoughtfully located on the opposite side of the primary suite and share a full bathroom featuring a TUB AND SHOWER COMBINATION. The HOA COVERS THE EXTERIOR OF THE HOME, LAWN MAINTENANCE, AND COMMON AREAS, providing added convenience and peace of mind. Residents of THE ORCHARD enjoy GATED SECURITY, a TRANQUIL COMMUNITY POOL, and PLAYGROUND, all in a prime WINTER GARDEN LOCATION just minutes from shopping, dining, top-rated schools, and the charm of DOWNTOWN WINTER GARDEN. TASTEFULLY UPDATED, WELL-MAINTAINED, AND MOVE-IN READY, this townhome offers an exceptional combination of STYLE, COMFORT, PRIVACY, AND CONVENIENCE, with many of the major updates already completed for you. Come see why you will love calling THE ORCHARD HOME!

242 Winter Nellis Circle, Winter Garden

$514,900

4 Beds ⋅ 3 Baths ⋅ O6434740 MLS

Virtually Staged. ~Seller may consider buyer concessions if made in an offer~Perfectly situated in sought-after Summerlake Groves of Winter Garden, this BEAUTIFULLY MAINTAINED 4-bedroom, 2.5-bath two-story home offers a light and bright OPEN CONCEPT floor plan, over 2,000 SQUARE FEET of living space, a convenient rear-entry garage and the peace of mind that comes with a home built in 2018. MOVE-IN READY and thoughtfully designed for comfortable family living, this home combines everyday functionality with the lifestyle that makes Winter Garden such a desirable place to call HOME. Step inside to find easy-care CERAMIC TILE FLOORS throughout the main living areas and an inviting flow from the spacious Living Room into the Kitchen and Dining area. An abundance of windows fills the Living Room with NATURAL LIGHT, while the open sight lines make gathering with family or entertaining friends effortless. At the heart of the home, the Kitchen overlooks the living space and features GRANITE COUNTERTOPS, stainless steel appliances, a closet pantry and a generous ISLAND with BREAKFAST BAR SEATING and room for counter-height stools. Just beyond, the bright Dining area offers sliding glass door access to the COVERED BRICK-PAVER PATIO, creating an easy transition for morning coffee, weekend cookouts or relaxing outdoors. Upstairs, the PLUSH CARPETED BEDROOMS provide a comfortable retreat away from the main living spaces. The spacious Primary Suite features a decorative TRAY CEILING, DUAL WALK-IN CLOSETS and a private en-suite bath with dual sinks, STEP-IN SHOWER and private WATER CLOSET. Three additional Bedrooms offer plenty of room for family, guests, a home office or hobbies, with some Bedrooms featuring their own WALK-IN CLOSETS. A second Full Bath has been recently retiled, and the conveniently located second-floor Laundry Room comes with a UTILITY TUB and includes the WASHER and DRYER. Outside, the BRICK-PAVER DRIVEWAY and REAR-ENTRY GARAGE add curb appeal while keeping the front of the home welcoming and attractive. Summerlake Groves offers a wonderful FAMILY-FRIENDLY atmosphere with a LOW HOA and amenities designed for enjoying the Florida lifestyle, including a clubhouse, RESORT-STYLE POOL, playground, dog park and TENNIS COURTS. Community events and SEASONAL FESTIVITIES create even more opportunities to get to know your neighbors and enjoy where you live.The Winter Garden location is hard to beat, with DISNEY WORLD just minutes away and HAMLIN TOWN CENTER nearby for shopping, dining and everyday conveniences. Spend the weekend exploring local parks, enjoying the WEST ORANGE TRAIL, grabbing dinner in Hamlin or heading to the nearby attractions. Zoned for EXCELLENT SCHOOLS and surrounded by the shopping, dining, recreation and entertainment that make Winter Garden so popular, this home provides the ideal combination of comfort, community and convenience. Well maintained, MOVE-IN READY, NEWER CONSTRUCTION and perfectly positioned in one of Winter Garden’s most sought-after areas — this is the one you’ve been waiting for! Call today to schedule your private showing and make Summerlake Groves your next HOME.

8016 Sweet Orange Avenue, Winter Garden

$2,600,000

6 Beds ⋅ 6 Baths ⋅ O6432738 MLS

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 7693 Green Mountain Way in Winter Garden, an impressive two-story lakefront home offering 6 bedrooms, 6 bathrooms, dual primary suites, a spacious loft, balcony, and multiple indoor and outdoor living areas. Designed to accommodate both everyday living and large-scale entertaining, this expansive residence combines flexible living spaces with standout waterfront amenities and scenic lake views. The interior provides an abundance of space across two levels, highlighted by two primary bedrooms that offer added flexibility for multigenerational households, extended guests, or those who simply prefer multiple private retreats. Four additional bedrooms and six full bathrooms provide generous accommodations throughout the home. A large loft adds another dedicated living area that can easily function as a media room, game room, secondary family room, or entertainment space. The balcony extends the living area outdoors and provides another inviting place to unwind while taking in the surrounding views. Multiple gathering areas throughout the home allow plenty of room for entertaining while still providing separation and privacy when desired. The outdoor spaces are designed to make the most of the home's scenic lakefront setting. A welcoming front porch adds curb appeal, while the rear of the home opens to a covered patio, spacious deck, and outdoor kitchen, creating a well-equipped setting for dining, grilling, and entertaining. The centerpiece is the in-ground infinity pool and spa overlooking the lake, where the water's edge blends beautifully with the waterfront backdrop. With dedicated areas for cooking, lounging, swimming, and gathering, the combination of the outdoor kitchen, covered patio, deck, infinity pool, spa, and expansive lake views creates a resort-inspired outdoor retreat ideal for both everyday relaxation and entertaining. Situated in Winter Garden, the property offers access to a vibrant Central Florida community known for its parks, recreational opportunities, shopping, dining, and convenient connections to major roadways and Orlando-area destinations. With six bedrooms, dual primary suites, six bathrooms, a loft, balcony, expansive outdoor living areas, and a lakefront infinity pool and spa, 7693 Green Mountain Way delivers exceptional space, flexibility, and waterfront living in one impressive property

7693 Green Mountain Way, Winter Garden

$435,000

8 Beds ⋅ 3 Baths ⋅ O6435284 MLS

8 bedrooms. 3 full baths. Approximately 1,750 SF. Just blocks from Plant Street. Space and location set this property apart. Offering 8 bedrooms and 3 full baths across approximately 1,750 SF, the home sits on a 9,431 SF fully fenced lot—a combination of interior space and land increasingly difficult to find this close to Historic Downtown Winter Garden. Built in 1925 and sold as-is, the home presents an opportunity to update and personalize to your own vision. The flexible room count provides options for bedrooms, guest space, home offices, or additional living needs, while the generous 75' x 125' lot leaves plenty of outdoor space to create a garden, entertaining area, or backyard retreat. No HOA, city utilities, and R-2 zoning add to the property's flexibility and long-term appeal. Location is the part that cannot be renovated. Enjoy being just blocks from Plant Street, the Saturday farmers market, restaurants, cafés, shops, entertainment, and the West Orange Trail, with Lake Apopka, SR-429, and Florida's Turnpike conveniently nearby. Currently income producing, the property offers the flexibility to maintain its existing rental use or be delivered vacant upon request. 8 Bedrooms. 3 Full Baths. Approx. 1,750 SF. 0.22 Acres. 9,431 SF Lot. 75' x 125'. No HOA. Bring your vision and make the space your own in a location that's increasingly difficult to replicate. Schedule your private showing today.

208 3rd Street, Winter Garden

$795,000

5 Beds ⋅ 4 Baths ⋅ TB8532509 MLS

Welcome to this beautifully renovated residence offering an additional den, approximately 3,197 square feet of comfortable living space, and a two-car garage. Set on an oversized 0.29-acre lot in the gated Wintermere Pointe community, this home blends generous living areas with thoughtful, contemporary upgrades. Inside, you’re greeted by a bright, open layout finished with fresh neutral colors, crown molding, updated lighting, and attractive flooring throughout the main living areas. The floor plan provides multiple spaces for entertaining, dining, working from home, or simply relaxing. The completely redesigned kitchen serves as the heart of the home, featuring:Extensive shaker-style cabinetry, Dramatic stone countertops, Classic subway-tile backsplash, Under-cabinet lighting, Stainless-steel appliances, Double wall ovens, Contemporary range hood, Oversized waterfall island with abundant workspace and storage, built-in window seat with additional cabinetry, Separate beverage area with wine storage and beverage refrigerators. The kitchen opens naturally to the expansive living and dining areas, creating an inviting atmosphere for everyday living and gatherings. Large windows and sliding glass doors bring in natural light and offer easy access to the outdoor living space and spacious backyard. The first-floor den provides a versatile area that can serve as a home office, study, media room, or guest retreat. With five bedrooms and four bathrooms, the home offers comfortable accommodations and a layout designed for both privacy and flexibility. The upstairs layout includes a spacious bonus area that can easily be converted into a movie theater room. With existing built-in cabinetry and space for a refrigerator or beverage center, it’s an ideal setup for a private entertainment space, gaming room, or family media lounge. This home is located in one of Winter Garden’s highly regarded school zones, serving: Lake Whitney Elementary School, SunRidge Middle School, West Orange High School. Families appreciate the strong academic reputation and convenient proximity to these schools. This area is Prime Winter Garden Location. Just minutes from Winter Garden Village, shopping, dining, entertainment, and major roadways—including SR 429, Florida’s Turnpike, and SR 408—this move-in-ready home offers space, style, and accessibility in one of Winter Garden’s established gated communities. Schedule Your Private Showing Come experience the comfort, upgrades, and welcoming atmosphere of this beautifully updated Winter Garden home.

2157 Wintermere Pointe Drive, Winter Garden

$749,000

5 Beds ⋅ 4 Baths ⋅ O6434615 MLS

Welcome to 2027 Rickover Place, located in the highly desirable gated community of Bronson’s Landing in Winter Garden! This beautiful home offers a spacious and versatile floor plan designed for both comfortable everyday living and entertaining. The home features split living spaces, providing flexibility and plenty of room to spread out. Upstairs, you'll find a spacious loft that can easily be transformed into a home office, media room, game room, playroom, or additional living area—the possibilities are endless. A three-car garage provides ample space for vehicles, storage, or hobbies. Bronson’s Landing offers an inviting, well-maintained neighborhood setting with a welcoming community atmosphere, creating a wonderful place to enjoy all that Winter Garden has to offer. Enjoy the convenience of being just minutes from Winter Garden Village, with an abundance of shopping, dining, and entertainment nearby. Easy access to SR-429 makes traveling throughout Central Florida convenient, while the home’s location near area schools adds to its appeal. With its gated community, flexible living spaces, three-car garage, and fantastic Winter Garden location, this home has so much to offer. Schedule your private showing today!

2027 Rickover Place, Winter Garden

Winter Garden Homes with Two Story Style

Newest Winter Garden Homes with Two Story Style

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