Winter Garden Real Estate

Winter Garden Real Estate

Welcome to Winter Garden, Florida—a charming city that perfectly blends small-town warmth with modern conveniences! Nestled in the heart of Orange County, Winter Garden boasts a rich history and a vibrant community spirit that beckons residents and visitors alike.

With its picturesque downtown area, Winter Garden is a delightful treasure trove of boutiques, cafes, and restaurants, all set against the backdrop of beautifully preserved historic buildings. The city’s commitment to maintaining its heritage is evident in the charming architecture and the lively events held throughout the year, including the popular Winter Garden Farmers Market, where local vendors showcase fresh produce and handmade goods.

Nature lovers will find a haven in Winter Garden, with numerous parks and recreational areas that encourage outdoor activities. The West Orange Trail, a scenic 22-mile-long path, winds through the city, inviting walkers, joggers, and cyclists to explore its stunning landscapes. Whether you’re enjoying a leisurely stroll by Lake Apopka or picnicking in one of the many parks, Winter Garden offers an abundance of natural beauty.

Families will appreciate the top-rated schools and friendly neighborhoods that make Winter Garden an ideal place to call home. The community is known for its strong sense of belonging, with residents often gathering for seasonal festivals, outdoor concerts, and community events that foster connections.

With its perfect blend of history, community, and natural beauty, Winter Garden is not just a place to live; it’s a place to thrive. Come discover the charm of Winter Garden, where every day feels like a warm embrace!

Newest Listings in Winter Garden

$945,000
4 Beds 4 Baths O6429007 MLS
Welcome to 14897 Ellingsworth Lane – A Spacious Retreat in Gated Oxford Chase Tucked away on a quiet cul-de-sac in the sought-after gated community of Oxford Chase, this stunning 4-bedroom, 3 1/2-bathroom home with a flex space ideal for a home office offers the perfect balance of elegance, function, and location. Built in 2018, the home features an open-concept layout, soaring ceilings, and a long list of upgrades designed for today’s modern lifestyle. From the moment you arrive, you’ll be drawn in by the lush landscaping, paver driveway, and welcoming covered front porch. Inside, enjoy dramatic two-story ceilings, abundant natural light, and designer fixtures—including crystal and chrome chandeliers in both the formal dining room and the second dining area off the kitchen. At the heart of the home, the spacious kitchen boasts shaker cabinetry, quartz countertops, a large island, walk-in pantry, stylish backsplash, natural gas stove, and stainless-steel appliances—all opening to the generous family room, perfect for entertaining or relaxing. The thoughtfully designed split floor plan features a serene primary suite on one side of the home, complete with a spacious bedroom, his-and-her walk-in closets, and a spa-like en-suite bath with dual vanities, soaking tub, and walk-in shower. A second en-suite bedroom on the opposite wing offers privacy for guests, in-laws or multigenerational living. Two additional downstairs bedrooms provide versatility, and one of them is currently used as a home office. Both larger bedrooms feature walk-in closets, while the stylish powder room adds convenience near the main living areas. Upstairs, a large open loft provides flexible space for a TV room, homework area, or playroom, alongside two more bedrooms—one with new carpet, the other with luxury vinyl plank flooring—and a full bath. Additional features include: Three-car garage (2-car plus separate 1-car currently used as a gym) Tile flooring throughout the main living areas Wide luxury vinyl plank flooring in most bedrooms Ceiling fans throughout Laundry room on the first floor with both gas and electric dryer hook-ups Optional water softening system Security system, window blinds, and natural gas connection Expansive backyard ready for outdoor entertaining Community playground and dog park The location is unbeatable— very close to A-rated Sun Ridge Elementary and Sun Ridge Middle School, so you’ll never sit in car lines again! You’re also just minutes from Tucker Ranch, Winter Garden Village, historic Downtown Winter Garden, and Oakland, with easy access to Avalon Road and major highways. With its prime location, spacious layout, and luxury finishes, this home truly has it all. Don’t miss the opportunity to make 14897 Ellingsworth Lane your next address.

14897 Ellingsworth Lane, Winter Garden

$859,000
4 Beds 3 Baths O6426625 MLS
RARE FIND! Experience resort-style living in this exceptional home on a rare OVERSIZED 0.15-acre homesite, ideally located JUST MINUTES from the vibrant HAMLIN Town Center in one of Winter Garden's most desirable areas. Featuring a stunning nearly NEW HEATED SALTWATER PRIVATE POOL, premium summer kitchen, expansive covered lanai, elegant travertine patio, and a fully fenced backyard, this property offers the Florida lifestyle today's buyers are looking for. Offering 2,990 square feet, 4 spacious bedrooms, and 2.5 bathrooms, this home perfectly blends luxury, comfort, energy efficiency, and everyday functionality. Designed with flexibility in mind, it also features a versatile flex room with the potential to serve as a future fifth bedroom, home office, or study, as well as a spacious upstairs bonus room ideal for a media room, playroom, or additional family living space. The primary suite is complemented by an oversized walk-in closet. The fully fenced backyard is a true private retreat designed for entertaining and relaxing year-round. The nearly new heated saltwater pool was built with all required permits, offering the confidence and peace of mind that come with a recently constructed, modern pool system. Outdoor living is completed by the covered lanai and travertine deck, a premium summer kitchen, and low-maintenance artificial turf. A convenient first-floor half bathroom with direct access to the backyard makes entertaining even more enjoyable. Beyond its outdoor living spaces, this home also delivers a remarkable financial advantage. The FULLY PAID-OFF SOLAR PANEL SYSTEM, valued at over $30,000, means no lease or loan to assume and helps keep the average monthly electric bill at approximately $80, even during Florida's summer months. That's hundreds of dollars in energy savings every month, providing exceptional long-term value and sustainability for the next homeowner. Additional upgrades include a beautifully remodeled upstairs bathroom with a frameless glass shower enclosure, custom closet systems, two independent HVAC systems for enhanced comfort and efficiency, professionally installed gutters, an epoxy-coated garage floor, and overhead garage storage racks. The location adds even more value: just minutes from Hamlin Town Center, with convenient access to top-rated schools, Publix, Walmart, restaurants, cafés, boutique shopping, Cinépolis Luxury Cinemas, PopStroke, Urban Air Adventure Park, and SR-429. As a resident of the highly desirable Summerlake community, you'll enjoy standout amenities, including a clubhouse, fitness center, community pool, tennis courts, playgrounds, walking trails, and lawn maintenance included through the HOA. Move-in ready and thoughtfully upgraded throughout, this home offers a rare combination of outdoor living, energy efficiency, and prime Winter Garden location. Schedule your private showing today! All information, including room dimensions, square footage, HOA fees, community amenities, and restrictions, is deemed reliable but not guaranteed and should be independently verified by the buyer and buyer’s agent.

7594 Lake Hancock Boulevard, Winter Garden

$778,000
5 Beds 4 Baths O6428748 MLS
****DREAM HOME ALERT**** PREMIUM LOT – WATER VIEW WITH BEAUTIFUL FOUNTAIN, NO REAR NEIGHBORS ** **PRIVACY BUSHES** **FIVE (5) PLUS BONUS/LOFT** **FIRST FLOOR BEDROOM & FULL BATHROOM **GOURMET KITCHEN** TONS OF UPGRADES**MAINTENANCE FREE COMMUNITY. Welcome to this beautiful spacious home located in Winter Garden’s highly coveted Waterleigh community which features beautiful homes, incredible amenities and lake views at every turn. This move-in ready Cresswell home is one of the builder’s most popular floor Plan. A beautiful porch welcomes you to this home, as you enter the foyer, to the left is a bedroom and full bath that can be used as an office or bedroom for an in-law or teenage/adult child offering much privacy from the rest of the home. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a SPACIOUS KITCHEN ISLAND and WALK-IN PANTRY for extra storage along with STAINLESS STEEL APPLIANCES. As we head up to the second floor, we are greeted with a HUGE LOFT AREA. You will also find the rest of the bedrooms and Master suite upstairs with a split plan for privacy. The Master has a VERY SPACIOUS WALK-IN CLOSET with CUSTOM BUILT-INS, as well as ensuite bathroom with double sinks, Walk-in Shower & separate SOAKING TUB and private toilet area with door. Down the hall from the master (split plan allowing privacy) we will find two additional bedrooms with large closet space that share a second upstairs bathroom with dual sinks and linen closet for extra storage. While a fourth bedroom is complete with a walk-in closet and ENSUITE BATHROOM. Your laundry room is also located on the second floor for convenience. Low HOA FEE of just $245 a month and INCLUDES ALL LAWN CARE CUTTING, FERTILIZATION, EXTERIOR PEST CONTROL & TRIMMING OF HEDGES/TREES of your LARGE lot...in addition to the community's incredible resort-style pools, clubhouses, fitness centers, parks, playgrounds, dog park, beach volleyball, tennis courts, putt-putt, fishing pier, walking trails…& MORE! This HOME IS THE PERFECT location with a PUBLIX SHOPPING CENTER just a short distance from home, located at the community entrance. That’s NOT ALL-WATERLEIGH is a GOLF CART FRIENDLY COMMUNITY that is conveniently located to all of the exciting shopping, dining & entertainment of Winter Garden’s Horizon West -- minutes from Walt Disney World & other area attractions -- minutes from HWY 429 access with easy direct connection to anywhere in Central Florida & beyond -- zoned for top-notch schools. WELCOME HOME! Some Post Builder UPGRADES and ADD-ONS include (see attachment for full list) Central Vac system, In-Ceiling Speakers, Internet Cable system, Upgraded Pendant lighting & tiled backsplash in Kitchen, High end Bosch Dishwasher installed 2024, Screened in porch, Extended paved deck and backyard firepit, Fully Fenced in backyard with 2 gates, Tall Privacy bushes installed on both sides of fence, GUTTERS, Epoxy floors in garage, Ultra quiet My Q controlled garage doors, Upgraded smart strand stain resistant carpet with upgraded padding for comfort and sound control, Master closet built-ins, Multiple Storage cabinets installed to laundry room and bathrooms, just to name a few.

16124 Azure Key Street, Winter Garden

$1,249,990
5 Beds 4 Baths O6427494 MLS Meritage BLDG.
Virtually Staged. Modern architecture. Total effortlessness. This five-bedroom residence is a masterclass in high-end finish designs, featuring high ceilings, iron-rod accents, and a dramatic, gallery-inspired aesthetic. At its heart, a chef-caliber kitchen serves as the ultimate hub for refined entertaining. Step into a home where luxury meets thoughtful innovation. This sprawling corner-lot property, crafted by the renowned Meritage Homes, is a rare find that perfectly balances grand proportions with everyday comfort. Boasting five spacious bedrooms, four full baths, and two half baths, the layout is designed for those who love to host and move freely through their space. The heart of the home is an expansive, sun-drenched open floor plan that flows effortlessly toward your own private oasis. Step outside to find a beautiful screened-in pool area, ideal for afternoon swims or evening gatherings without the worry of the elements. What truly sets this residence apart is the commitment to quality and efficiency. Protected by a timeless tile roof, the home features high-energy windows and spray-foam attic insulation, keeping the interior crisp and cool while keeping utility costs in check. The oversized three-car garage even comes equipped with a Tesla charger, ready for your electric vehicle. From the numerous high-end upgrades found throughout the interior to the curb appeal of its prominent corner position, every detail has been considered. This is more than just a house; it’s a modern, energy-efficient sanctuary built for a sophisticated lifestyle. The experience extends to a private pool house, complete with a game room and a theater-style loft. Outside, the pool anchors an at home retreat. This is luxury without the logistics. Your residency is entirely turnkey and ready for you to move in.

1734 Amsel Falls Park Terrace, Winter Garden

$915,000
3 Beds 4 Baths O6428419 MLS N/A BLDG.
Experience luxury living in the heart of historic downtown Winter Garden! This beautifully designed corner-unit brownstone offers 3 bedrooms, 3.5 bathrooms, 2,242 square feet of thoughtfully crafted living space, and an unbeatable location just steps from everything that makes downtown so special. Situated right next to Plant Street Market and Crooked Can Brewing Company, you'll enjoy effortless access to the award-winning Saturday Farmers Market, local festivals, live entertainment, boutique shopping, and an incredible selection of restaurants and cafés, all just outside your front door. Step inside to discover a the first-floor layout featuring a private bedroom with its own en suite bathroom, creating the perfect retreat for overnight guests, extended family, or even a private home office. The second floor is the heart of the home, where an open-concept living, dining, and kitchen area creates an inviting atmosphere for both entertaining and everyday living. As a coveted corner unit, oversized windows fill the space with natural light, while crown molding adds an elegant finishing touch throughout. The gourmet kitchen is designed to impress, showcasing an oversized center island, stainless steel appliances, stylish finishes, generous counter space, and abundant cabinetry. A dedicated bar area nearby makes hosting gatherings even more effortless, while the adjoining living room features access to two covered balconies, giving you the perfect place to enjoy fresh air or unwind after a day exploring downtown. Occupying the third floor, the spacious primary suite offers a peaceful escape with a large walk-in closet and a luxurious en suite bathroom complete with dual vanities and a stunning freestanding soaking tub. An additional upstairs bedroom provides generous closet space, abundant natural light, and comfortable accommodations for your loved ones. Additional highlights include a two-car garage and a location within Winter Garden's highly desirable golf cart district, making it easy to explore downtown's vibrant shops, restaurants, parks, and community events without ever needing your car. Convenient access to major highways places the rest of Central Florida within easy reach, while your everyday lifestyle is centered around one of the region's most sought-after downtown destinations. If you've been searching for luxurious low-maintenance living with unmatched walkability, this exceptional townhome is the opportunity you've been waiting for. Schedule your private showing TODAY!!!

484 W Plant Street, Winter Garden

$1,100,000
4 Beds 3 Baths O6428247 MLS
Move in ready home with remarkable sunsets, breathtaking panoramic views of Lake Apopka, and calming bird watching right from the backyard. Highlights of this home from outside to inside are wide paver driveway with parking pad, spacious 3 car garage, covered front and rear porches, fully fenced in backyard, extended rear concrete patio, large flex room, mother in law suite with private entrance and kitchenette, and incredible kitchen to love at the center of an open floorplan. Floorplan: Triple split layout puts the primary suite, the secondary bedrooms, and the mother in law suite each in their own private area of the home. The mother in law suite has its own private exterior entrance, kitchenette, bedroom, and full bath. Large flex room for a home gym, office, studio, gaming room, or playroom. Kitchen: Cabinets to the ceiling, stone counters, beveled subway tile, farmhouse sink, island with seating for four, built-in wall oven and microwave, stainless vented hood, pot filler above the cooktop, spacious pantry, open to the living and dining space. Interior: Tray ceilings in the dining room, living room, and primary suite, wood slat accent wall, crown molding, upgraded lighting, ceiling fans, window treatments installed. Primary suite with walk in closet, corner tub, double sinks, and glass shower. Ceramic tile in main living areas, carpet in secondary bedrooms, inside laundry room. Exterior: Wide paver driveway with large paved parking pad, spacious three car garage, covered front porch, covered rear porch, extended full width concrete patio, fully fenced backyard with gates on both sides, sprinkler system throughout, tile roof. Recreation: Killarney Station trailhead five minutes out with bike rentals, repairs, and supplies center. West Orange Trail runs 20 plus miles into historic downtown Winter Garden. Lake Apopka Wildlife Drive and Lake Louisa State Park both an easy drive. Convenience: Downtown Wintergarden 25 minutes, Costco 8 minutes, Disney 25 minutes, Downtown Orlando 30 minutes, MCO Airport 35 minutes.

17854 Hither Hills Circle, Winter Garden

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