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226 Charlotte Street, Winter Garden
$449,999
3 Beds ⋅ 2 Baths ⋅ East Garden Manor Rep SubDv. ⋅ 34787 Zip Code
UNIQUE PROPERTY OPPORTUNITY!! Nearly of an 1/4 ACRE with NO HOA!! Welcome to this charming 3-bedroom, 2-bathroom home in the heart of Winter Garden! Situated on an oversized lot, this property offers added space and flexibility rarely found in many communities. Inside, enjoy a cozy fireplace, a unique wood accent wall, and an updated kitchen featuring custom cabinetry and convenient hidden storage. Ceramic tile and bamboo flooring, double-pane windows, and a screened front porch add to the home's appeal. The spacious backyard offers two storage sheds, offering plenty of room for outdoor enjoyment, hobbies, and additional storage. Hot water tank 2 years old. Conveniently located walking distance to Downtown Winter Garden, the West Orange Trail. This home combines charm, functionality, and the freedom of homeownership without HOA restrictions!

226 Charlotte Street, Winter Garden
427 Lake Amberleigh Drive, Winter Garden
$550,000
4 Beds ⋅ 2 Baths ⋅ Amberleigh SubDv. ⋅ 34787 Zip Code
Welcome to 427 Lake Amberleigh Dr, a beautifully maintained, one-story home tucked inside the gated Amberleigh community of Winter Garden! Offering 4 bedrooms, 2 bathrooms, and 2,158 square feet of thoughtfully designed living space, this home combines timeless details with meaningful updates throughout. Step inside to high ceilings, crown molding, and wood look plank tile that flows throughout the home. Just off the entry, the formal dining room offers a welcoming space for gatherings, while the spacious living room makes a statement with an entire wall of custom white built-in shelving and sliding glass doors leading to the covered patio. The remodeled kitchen, completed in 2019, features soft gray shaker cabinetry, white countertops and backsplash, a breakfast bar with seating, and stainless steel appliances. Recent 2026 upgrades include a new double-oven range, dishwasher, and microwave. The kitchen opens seamlessly to a bright, inviting family room surrounded by windows, creating a comfortable space for everyday living and entertaining. The spacious primary suite features a tray ceiling and a beautifully remodeled ensuite bath with a freestanding soaking tub, frameless glass walk-in shower, and dual vanities. Three additional bedrooms offer flexibility for guests, family, or a home office, while the interior laundry room adds everyday convenience. The home has also seen several important improvements, including a roof and AC replacement in 2019, interior and exterior paint, and a whole-home water filtration and softener system. Additional 2026 upgrades include a new exterior electrical panel with whole-home surge protection, a 220V outlet in the two-car garage, and a new garage door opener. Outside, enjoy the fully fenced backyard with mature shade trees and an extended patio, offering plenty of room to relax, entertain, or enjoy the Florida sunshine.

427 Lake Amberleigh Drive, Winter Garden
730 Magnolia Street, Winter Garden
$850,000
5 Beds ⋅ 3 Baths ⋅ Winter Gdn Manor SubDv. ⋅ 34787 Zip Code
Virtually Staged. ***NEW CONSTRUCTION LUXURY HOME*** 5 bedrooms / 2.5 bathrooms ***Two-car garage ***Two-story home ***Luxurious glass entry doors ***Grand foyer featuring a beautiful, elegant chandelier ***Staircase with a wrought-iron railing ***Foyer accented with custom decorative wall paneling ***Open-concept layout: integrated living room, dining area, and kitchen ***Large quartz kitchen island ***High-end KitchenAid appliances ***Custom kitchen range hood ***Walk-in pantry ***Indoor laundry room ***Primary suite located on the ground floor ***Bedrooms 2, 3, 4, and 5 located upstairs, alongside a spacious loft area—perfect as a family living space ***Elegant 6- panel doors with detailed trim ***8-inch baseboards and crown molding ***Foam insulation for enhanced energy efficiency ***Large covered rear patio ***No Homeowners Association (HOA) fees ***Generous lot size (50x150 feet), VINYL FENCED for privacy with ample space to add a private pool or a detached workshop ***Located in a non-flood zone ***North-facing orientation*** Prime location: just minutes from downtown Winter Garden, Winter Garden Village, the Winter Garden Trail, and Disney World. Easy access to the Florida Turnpike and toll roads 408 and 429, offering a convenient commute to the airport and downtown Orlando.

730 Magnolia Street, Winter Garden
740 Magnolia Street, Winter Garden
$850,000
5 Beds ⋅ 3 Baths ⋅ Winter Garden Manor SubDv. ⋅ 34787 Zip Code
Virtually Staged. ***NEW CONSTRUCTION LUXURY HOME*** 5 bedrooms / 2.5 bathrooms ***Two-car garage ***Two-story home ***Luxurious glass entry doors ***Grand foyer featuring a beautiful, elegant chandelier ***Staircase with a wrought-iron railing ***Foyer accented with custom decorative wall paneling ***Open-concept layout: integrated living room, dining area, and kitchen ***Large quartz kitchen island ***High-end KitchenAid appliances ***Custom kitchen range hood ***Walk-in pantry ***Indoor laundry room ***Primary suite located on the ground floor ***Bedrooms 2, 3, 4, and 5 located upstairs, alongside a spacious loft area—perfect as a family living space ***Elegant 8-panel doors with detailed trim ***8-inch baseboards and crown molding ***Foam insulation for enhanced energy efficiency ***Large covered rear patio ***No Homeowners Association (HOA) fees ***Generous lot size (50x150 feet), VINYL FENCED for privacy with ample space to add a private pool or a detached workshop ***Located in a non-flood zone ***North-facing orientation*** Prime location: just minutes from downtown Winter Garden, Winter Garden Village, the Winter Garden Trail, and Disney World. Easy access to the Florida Turnpike and toll roads 408 and 429, offering a convenient commute to the airport and downtown Orlando.

740 Magnolia Street, Winter Garden
1444 Kenny Court, Winter Garden
$350,000
3 Beds ⋅ 2 Baths ⋅ Kenny Court SubDv. ⋅ 34787 Zip Code
Welcome to this inviting 3-Bedroom, 2-Bath single-story home in a DESIRABLE LOCATION near Winter Garden, offering a spacious CORNER LOT, NO HOA and plenty of room to make the most of Florida living! Set on NEARLY A QUARTER ACRE, the property features MATURE SHADE TREES, a large driveway with ample parking and a welcoming setting. Inside, BEAUTIFUL LVP FLOORING and NEW LEVELOR BLINDS throughout, create a fresh, cohesive look, while NEW AC (2026) and a ROOF REPLACED IN 2022 add peace of mind. The OPEN FLOOR PLAN allows the Living Room, Dining Room and Kitchen to flow together seamlessly, creating a comfortable setting, while NATURAL LIGHT fills the space, enhancing the bright and airy feel. The Kitchen offers plenty of SOLID WOOD WHITE CABINETRY, solid-surface countertops and a center island with breakfast bar seating. A RECENTLY UPDATED TILE BACKSPLASH adds a stylish finishing touch, while STAINLESS STEEL APPLIANCES—including a GAS STOVE—make meal preparation a pleasure. A window above the sink brings in NATURAL LIGHT and provides a view of the backyard, and a CONVENIENT LAUNDRY ROOM is located just off the Kitchen. Down the hallway, you’ll find THREE BEDROOMS, each featuring a STYLISH CEILING FAN and WALK-IN CLOSET for comfortable living and convenient storage. The Primary Suite presents a private retreat with its own en suite Bath, complete with a MODERN VANITY AND TILED WALK-IN SHOWER. A SECOND FULL BATH with a modern vanity and tub/shower combination, is conveniently located near the additional Bedrooms.The Kitchen provides access to the backyard, where there's an OPPORTUNITY to create an outdoor space that reflects your own style, whether you envision a GARDEN, entertaining area or a place to relax under the Florida sunshine. With its GENEROUS CORNER LOT, mature shade trees and NO HOA, there’s room to make this property your own. Enjoy a GREAT LOCATION, just 2 miles from the charm and character of HISTORIC DOWNTOWN WINTER GARDEN, where you can explore local shops and restaurants, browse the popular PLANT STREET MARKET, visit the SATURDAY FARMERS MARKET or catch a show at the GARDEN THEATRE. Outdoor enthusiasts will appreciate the nearby WEST ORANGE TRAIL, ideal for biking, jogging and leisurely strolls, and with CONVENIENT ACCESS to Florida's Turnpike and SR-429, you can easily reach Orlando’s WORLD-FAMOUS THEME PARKS. Families will appreciate the nearby GREAT SCHOOLS including, A-RATED William Maxey Elementary and West Orange High School, adding to the appeal. With its thoughtful updates, GENEROUS LOT and convenient access to everything WINTER GARDEN has to offer, this home is FULL OF POTENTIAL and ready for its next chapter. Call and schedule your private tour today!

1444 Kenny Court, Winter Garden
1539 Hawkesbury Court, Winter Garden
$560,000
3 Beds ⋅ 2 Baths ⋅ Tuscany SubDv. ⋅ 34787 Zip Code
Welcome to 1539 Hawkesbury Court, located in the desirable Winter Garden area of Central Florida! This single-family home offers an excellent opportunity to enjoy the convenience, amenities, and lifestyle that make Winter Garden a sought-after place to call home. Conveniently located near shopping centers, restaurants, grocery stores, parks, and everyday essentials, residents can enjoy easy access to a variety of local conveniences. Explore the charm of historic Downtown Winter Garden, known for its unique shops, local restaurants, cafés, and welcoming atmosphere. The popular West Orange Trail is nearby, offering miles of scenic paths for walking, jogging, and cycling. Winter Garden Village provides an array of retail stores, dining options, and entertainment for added convenience. The property's location also offers access to major roadways, including Florida's Turnpike and State Road 429, making travel throughout the greater Orlando area convenient. Enjoy proximity to recreational opportunities, golf courses, and outdoor activities, while remaining within reach of Orlando's employment centers, attractions, and entertainment destinations. Whether you're looking for a place to call home or exploring real estate opportunities in the growing Central Florida market, this property presents an opportunity to enjoy the many benefits of the Winter Garden lifestyle.

1539 Hawkesbury Court, Winter Garden
225 1st Street, Winter Garden
$288,000
3 Beds ⋅ 1 Baths ⋅ Twin City Dev Co Sub SubDv. ⋅ 34787 Zip Code
Charming 3-bedroom, 1-bath home in Winter Garden offering 1,020 sq. ft. of comfortable living space. This inviting home features a welcoming front porch, spacious living and dining areas, LVP flooring throughout the main living areas, and carpeted bedrooms. The kitchen is equipped with stainless steel appliances, including a refrigerator, range, and microwave. The upgraded bathroom adds a modern touch. Enjoy additional outdoor storage, a rear patio, and a large, fully fenced backyard—perfect for relaxing or entertaining. Conveniently located just minutes from Downtown Winter Garden, with its shops, restaurants, and entertainment. Close to West Oaks Mall and West Colonial Drive, providing easy access to shopping, dining, and major roadways.

225 1st Street, Winter Garden
231 E Lafayette Street, Winter Garden
$479,900
4 Beds ⋅ 3 Baths ⋅ M C Britt Sub 1 SubDv. ⋅ 34787 Zip Code
Seller its offering $7,000 for a buyer closing costs. Brand-New Construction in Winter Garden! Welcome to 231 E Lafayette Street, a beautifully designed 4-bedroom, 3-bathroom new construction home offering modern luxury, thoughtful craftsmanship, and exceptional functionality. From the moment you arrive, the striking contemporary exterior, covered front entry, and attached garage create an inviting first impression. Inside, the open-concept floor plan features luxury vinyl plank flooring throughout, soaring ceilings, recessed lighting, and an abundance of natural light. The stunning chef's kitchen is the centerpiece of the home, showcasing custom cabinetry, elegant quartz countertops, a large center island with breakfast bar, designer backsplash, stainless steel appliances, and a statement gold-finished faucet. The spacious island provides the perfect gathering space for entertaining or everyday living. The generously sized living area has a dramatic custom built-in feature wall with integrated shelving and a modern electric fireplace, creating a focal point. Large windows overlook the backyard and bring the outdoors in, while the contemporary ceiling fan and designer lighting add to the home's polished aesthetic. The primary suite provides a private retreat with ample space and a beautifully appointed en-suite bathroom, while three additional bedrooms, flexibility for family, guests, a home office, or media space. The home's three full bathrooms are finished with modern fixtures and elevated designer details. Outside, the property has a private fenced backyard with plenty of room to create your own outdoor oasis. The attached one-car garage and extended driveway provide convenient parking and storage. Ideally located in Winter Garden, this exceptional new construction home combines modern luxury with the charm and convenience of one of Central Florida's most desirable communities. Enjoy easy access to downtown Winter Garden, shopping, dining, parks, major roadways, and everything the area.. New construction. Modern design. Premium finishes. Prime Winter Garden location. This is a home you don't want to miss.

231 E Lafayette Street, Winter Garden
93 Windtree Lane Unit 102, Winter Garden
$188,000
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens SubDv. ⋅ 34787 Zip Code
Virtually Staged. BACK ON THE MARKET WITH BRAND NEW CARPET & FRESH PAINT! Welcome to this beautifully refreshed first-floor condo in the heart of Winter Garden! Offering 2 bedrooms and 2 bathrooms, this home presents an excellent opportunity for homeowners, first time buyers, or investors looking for convenience and value. Enjoy the ease of ground floor living with a private screened-in patio, perfect for sipping your morning coffee, enjoying the Florida weather, or relaxing at the end of the day. Inside, the functional layout has been refreshed with brand new carpet and fresh interior paint, giving the home a clean, move-in ready feel while providing the perfect opportunity to make it your own. The condo also includes a washer and dryer, making everyday living even more convenient. Two designated parking spaces are included, adding to the ease of ownership. Residents can take advantage of a variety of community amenities, including a swimming pool, basketball court, clubhouse, and community mailbox. Conveniently located near shopping, dining, entertainment, and major roadways, this condo combines affordability, comfort, and convenience in a desirable Winter Garden location. Whether you're looking for a place to call home or a smart investment opportunity, this one is ready for its next owner!

93 Windtree Lane Unit 102, Winter Garden
420 E Cypress Street, Winter Garden
$400,000
3 Beds ⋅ 2 Baths ⋅ Overstreet Crate SubDv. ⋅ 34787 Zip Code
Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.

420 E Cypress Street, Winter Garden
483 Pennsylvania Avenue, Winter Garden
$334,000
2 Beds ⋅ 2 Baths ⋅ East Garden Manor Add 03 SubDv. ⋅ 34787 Zip Code
Seller its offering $6,000 for buyers closing costs. Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roof, new plumbing, close to major roads, schools, minutes to Winter Garden dawn town.

483 Pennsylvania Avenue, Winter Garden
92 Windtree Lane Unit 201, Winter Garden
$218,000
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 03 SubDv. ⋅ 34787 Zip Code
Don’t miss this great investment opportunity in the heart of Winter Garden. This 2-bedroom, 2-bath condo offers laminated floors and is already rented, generating income from day one. Home features updated plumbing with a complete repipe. Located just minutes from Downtown Winter Garden, with easy access to restaurants, shops, parks, and major highways. Not a gated community, offering easy access and low-maintenance living. Perfect for investors seeking a stable, income-producing property.

92 Windtree Lane Unit 201, Winter Garden

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