4 Beds ⋅ 5 Baths ⋅ Winter Garden Shores 2nd Add SubDv. ⋅ 34787 Zip Code

Discover elevated living and the Winter Garden lifestyle in downtown's newest custom residence! Ideally positioned off the shores of Lake Apopka and within the beloved golf cart district, this exceptional home offers effortless access to Plant Street’s charming shops, restaurants, Farmers Market, Brewery numerous parks & the West Orange Trail. Thoughtfully designed by locals with a deep appreciation for the character of this historic city, this exquisite 4 bedroom, 4.5-bath home blends timeless charm with refined modern finishes throughout. Majestic oaks beautifully frame the home’s craftsman-inspired architecture, while the expansive front porch invites relaxation. Inside, an open-concept design and modern kitchen are curated for both everyday comfort and endless entertaining. Inviting living spaces are complemented by elevated finishes, a wine bar, custom built-ins, a butler’s pantry & outdoor kitchen. Creatively designed to include a drop zone with a one-of-a-kind dog wash station. All bedrooms feature ensuites and custom closets. Refined outdoor living abounds on the back porch with a custom summer kitchen. Don't miss this one-of-a-kind opportunity. Schedule your private showing today!

412 N Boyd Street, Winter Garden

$1,250,000

4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 1 & 6 SubDv. ⋅ 34787 Zip Code

Designed to impress and crafted for everyday living, 5513 Thomas Square Drive is a beautifully upgraded pool home in one of Hamlin's most sought-after communities. Offering 4 bedrooms, 3.5 bathrooms, a private office, an oversized loft, a versatile flex room, and a saltwater pool, this exceptional residence seamlessly blends timeless design with modern comfort. From the moment you arrive, the stone-accented elevation, oversized driveway, and manicured landscaping create unforgettable curb appeal. Inside, soaring ceilings, abundant natural light, crown molding, custom trim work, 8-foot doors, and wood-look tile flooring establish an elegant yet welcoming atmosphere. The dramatic two-story great room is the undeniable centerpiece of the home, showcasing a custom floor-to-ceiling built-in with cabinetry, open shelving, and a heat-producing electric fireplace, beautifully complemented by decorative wood ceiling beams that add warmth and architectural character. The open-concept kitchen is equally impressive, featuring white cabinetry, granite countertops, an oversized center island, stainless steel appliances, a gas cooktop, walk-in pantry, expansive butler's pantry, and a dedicated breakfast nook overlooking the backyard. Privately tucked away on the first floor, the primary suite offers engineered hardwood flooring, dual walk-in closets with custom shelving, and a spa-inspired bath with separate vanities, a soaking tub, and an oversized walk-in shower. A private office with matching engineered hardwood flooring, formal dining room, laundry room, and powder bath complete the main level. Upstairs, three spacious bedrooms, two full bathrooms, an oversized loft, and a flexible bonus room provide endless possibilities for a media room, fitness space, playroom, or potential fifth bedroom. Step outside to your own private retreat featuring a saltwater pool with water features, covered lanai, fenced backyard, and the added privacy of no rear neighbors. Thoughtful enhancements throughout the home include the custom family room built-in with electric fireplace, decorative ceiling beams, engineered hardwood flooring in the primary suite and office, permanent exterior architectural trim lighting, a whole-home security camera system, overhead garage storage, newer kitchen appliances, a new microwave, a newer pool pump, and spray foam insulation for enhanced energy efficiency. Residents enjoy resort-style amenities including a clubhouse, community pool, playground, and dog park, all just minutes from Hamlin Town Center, top-rated schools, shopping, dining, major highways, and Walt Disney World. Blending timeless design, quality craftsmanship, and an unbeatable location, 5513 Thomas Square Drive is a rare opportunity to own a truly move-in-ready home in the heart of Winter Garden.

5513 Thomas Square Drive, Winter Garden

$1,390,000

5 Beds ⋅ 4 Baths ⋅ Hillcrest SubDv. ⋅ 34787 Zip Code

A truly rare find in beautiful Downtown Winter Garden's highly coveted Golf Cart District, with NO HOA this exceptional 5-bedroom, 3.5-bath residence offers a once-in-a-lifetime opportunity to own a home where luxury, character, and location come together beautifully. Thoughtfully renovated from top to bottom, this one-of-a kind property combines timeless craftsmanship with modern elegance and resort-style outdoor living. Every inch of this home has been meticulously updated with high-end finished , including a stunning chef's kitchen featuring quartz countertops, a large center island, custom cabinetry with panel-ready appliances, double ovens, a wine refrigerator, a walk-in pantry, and gorgeous copper accents including a double farmhouse sink, matching range hood, pot filler, and faucet. The inviting living spaces showcase custom craftsman trim, elegant wainscoting, oversized baseboards, shiplap ceilings, a beautiful fireplace with a custom stone entertainment wall, a built-in library, designer lighting, and travertine flooring in the kitchen and bathrooms. Step outside into your own private backyard oasis where you'll find a heated, newly resurfaced pool and above-ground spa, a spacious paver pool deck, screened lanai, pergola with a fire pit, raised garden beds, and professionally designed landscaping surrounded by mature hedges, picket fencing, majestic oak trees, crepe myrtles, gardenias, and rose bushes, creating exceptional beauty and privacy. The expansive property also features a detached workshop, and an extra-long spacious driveway with abundant parking for all your toys!!This home offers peace of mind with countless recent upgrades, including a NEW ROOF with metal porch roofing, two NEW HVAC systems a NEW HOTWATER HEATER, NEW POOL PUMP, Ecobee smart thermostats, digital entry, a new pool bath, Centricon termite protection, and in-wall pest control tubing. Perfectly located just a short golf cart ride from Winter Garden's award-winning restaurants, charming boutiques, the famous Farmers Market, and the West Orange Trail, this is more than just a home—it's a lifestyle. Homes of this caliber, with this level of craftsmanship, outdoor amenities, and an unbeatable Downtown Winter Garden location, and NO HOA rarely come to market. Schedule your private showing today to experience everything this extraordinary property offers. If you are lucky enought to purchase this home you are not just getting a home, you're getting a rare opportunity in one of Central Florida's most desirable communities.

1324 Vic Kay Court, Winter Garden

$1,500,000

5 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to this stunning, like-new home that perfectly blends luxury, comfort, and modern design in the highly desirable community of Hull Island. Boasting five spacious bedrooms and four full bathrooms, this thoughtfully designed residence offers an ideal layout for both everyday living and entertaining. This home offers two spacious owner’s suites, one conveniently located on the first floor and another upstairs, making it ideal for multigenerational living, extended guests, or added privacy. Step inside to soaring high ceilings and an open-concept floor plan filled with natural light. The heart of the home is the gourmet gas kitchen, featuring 42-inch cabinetry, elegant quartz countertops, a large center island, built-in convection oven, stainless steel appliances and premium finishes throughout. A dedicated beverage station with a separate bar refrigerator provides the perfect space for entertaining guests. Upstairs, you'll find an expansive loft that offers endless possibilities as a media room, game room, home office, or additional living space. Outside, enjoy your own private backyard retreat complete with a sparkling pool, ideal for relaxing or hosting family and friends year-round. The garage is equipped with overhead storage shelving, providing ample space to keep seasonal items and equipment neatly organized. With its spacious layout, upscale finishes, abundant storage, and exceptional amenities, this beautifully maintained home is truly move-in ready and offers the perfect combination of elegance, functionality, and Florida living at its finest. This community features a pool pool, nature trails, playground, dog park, and private dock. Conveniently located near shopping, dining, main highway and more.

2010 Boss Hewett Street, Winter Garden

$1,450,000

4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 4 SubDv. ⋅ 34787 Zip Code

Captivating water and golf course views set the stage for a chic and distinguished single-story residence in Lakeshore Preserve. This better-than-new home boasts a great room floorplan with split bedroom layout, sliding pocket doors, an exceptional screened pool patio area with hybrid saltwater and chlorine pool with sun shelf and water features, plus tranquil lake beyond. Elegant white on white kitchen with stainless appliances, gas cooktop with hood, waterfall quartz island, and an abundance of cabinetry including a few lighted glass showplace cubicles with doors. Graced with wood-look tile flooring and transitional neutral grays and whites throughout this home offers a clean-look elegant canvas. Landscape lighting creates an elegant ambiance at night. Enjoy a nearly carefree lifestyle with exterior yard maintenance included in your monthly HOA fee. 1-gig high-speed internet is also included. Community features resort-style amenities including a waterfront community pool, cabanas, walking trails, and access to Lake Panther via a community ramp for canoes, kayaks, and other non-motorized watercraft. There’s also a community clubhouse with fitness center and activity spaces. Top-rated Panther Lake Elementary is located within the neighborhood and Horizon High School is across the street. Orange County National Golf Center is just minutes away. Enjoy nightly fireworks from the Magic Kingdom at Walt Disney World and easy access to the SR-429 to connect to downtown Orlando. Welcome to Horizon West’s best address for lifestyle, luxury, and livability.

15619 Giant Foxtail Court, Winter Garden

$1,359,999

4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 2 & 5 SubDv. ⋅ 34787 Zip Code

*** NEW PRICE! *** Welcome to this spacious 4-bedroom, 3.5-bath pool home offering 4,000 square feet in the highly sought-after Overlook at Hamlin community in Horizon West. Showcasing Lake Hancock views throughout the home and Disney fireworks in the distance, this property combines generous living space, impressive architecture, and an unbeatable location in one of Winter Garden's most desirable communities. From the moment you arrive, you'll appreciate the paver driveway, fresh landscaping, side-entry two-car garage, and curb appeal. Step inside to find a formal dining room and home office. Continue into the heart of the home where soaring ceilings and a dramatic two-story design create a bright, open atmosphere. The expansive family room showcases picturesque pool and lake views, while the open-concept layout flows seamlessly into the kitchen and casual dining area, making it ideal for everyday living and entertaining. The kitchen features granite countertops, light cabinetry, two oversized islands, abundant prep space, a walk-in pantry, and a butler's pantry ideal for a coffee station. Stainless steel appliances include a Monogram built-in oven and microwave, Monogram dishwasher, and a Monogram five-burner natural gas cooktop. The first-floor primary suite offers a private retreat with pool views, two walk-in closets, and an ensuite bath complete with dual vanities, a garden tub, and a large glass-enclosed shower. An impressive staircase with decorative iron balusters leads to the second floor, where an open overlook adds to the home's spacious feel. Upstairs you'll find three additional bedrooms, all with walk-in closets, two full bathrooms, a large loft perfect for a media room or secondary living area, and a versatile flex room that can serve as a home gym, study, playroom, hobby room, or potential fifth bedroom. Combined with the dedicated first-floor office, these flexible spaces provide exceptional versatility for remote work, multi-generational living, or growing households. Two upstairs bedrooms enjoy Lake Hancock views. Step outside to the expansive screened lanai with space for outdoor dining, relaxing, and entertaining. The saltwater pool and Lake Hancock views create an exceptional outdoor setting. Residents of Overlook at Hamlin enjoy access to a clubhouse, fitness center, resort-style pool, playgrounds, golf cart-friendly streets, and community lake access. Located just minutes from Hamlin Town Center, you'll enjoy convenient access to shopping, dining, waterfront restaurants, grocery stores, PopStroke, Cinépolis Luxury Cinemas, Urban Air, and everyday conveniences. A rare opportunity to own a spacious pool home with Lake Hancock views in the heart of Horizon West and Winter Garden's thriving Hamlin area.

15264 Shonan Gold Drive, Winter Garden

$1,335,000

4 Beds ⋅ 4 Baths ⋅ West Lake Hancock Estates SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully upgraded luxury home in Hamlin, offering 4 bedrooms, a dedicated theater room, bonus room, resort-style pool and spa, summer kitchen, and putting green. Built in 2016 and meticulously maintained, this exceptional residence sits on one of Overlook at Hamlin’s most desirable homesites, featuring rare elevated conservation and water views that provide privacy and a setting unlike the typical flat Florida lot. Inside, soaring ceilings, abundant natural light, and an open-concept layout create the perfect balance of comfort and sophistication. The fully remodeled chef’s kitchen features quartz countertops, brand-new appliances, an oversized island, built-in microwave, wine refrigerator, and a stunning custom Venetian plaster hood. The spacious primary suite offers custom walk-in closets and a spa-inspired bath with luxury designer touches. Additional highlights include a dedicated movie theater with tiered seating, a large bonus room, custom laundry room, camera security system, designer lighting, and premium finishes throughout. Step outside to your own private backyard retreat featuring a screened-in pool and spa, summer kitchen with fire feature, covered outdoor living space, putting green, and breathtaking conservation views. Living in Overlook at Hamlin means enjoying some of the best amenities in the area, including a clubhouse, fitness center, resort-style pool, playgrounds, golf cart-friendly streets, and private lake access. Just minutes from Hamlin Town Center, you’re surrounded by great restaurants, shopping, and entertainment. With amazing sunsets and a prime location in the heart of Horizon West, this is a rare opportunity to own a luxury pool home in one of Winter Garden’s most sought-after communities.

14591 Black Quill Drive, Winter Garden

$1,299,000

5 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code

Virtually Staged. Wake up to WATERFRONT SUNRISES, unwind beside your RESORT-STYLE POOL & SPA, and enjoy DISNEY FIREWORKS from your backyard every night. Situated on an OVERSIZED LAKEFRONT LOT spanning more than 1/3 ACRE with over 250 FEET OF DEPTH, this stunning 5 BEDROOM, 3.5 BATHROOM home offers the perfect blend of luxury, privacy, and lifestyle. The highly desirable NORTH HAVEN FLOOR PLAN features WOOD-LOOK TILE FLOORING, WROUGHT IRON STAIR RAILINGS, SMART HOME TECHNOLOGY, and a spacious OPEN-CONCEPT DESIGN. The GOURMET KITCHEN is appointed with QUARTZ COUNTERTOPS, UPGRADED CABINETRY WITH CROWN MOLDING, STAINLESS STEEL APPLIANCES, SUBWAY TILE BACKSPLASH, WALK-IN PANTRY, and a LARGE CENTER ISLAND perfect for entertaining. The PRIMARY SUITE is a private retreat featuring FRENCH DOORS TO THE LANAI, an OVERSIZED WALK-IN CLOSET, and beautiful WATER VIEWS. Upstairs, the expansive LOFT provides flexible space for a MEDIA ROOM, GAME ROOM, or HOME OFFICE. Step outside to your private backyard oasis featuring a HEATED POOL, OVERSIZED SPA, WATERFALLS, SUN SHELF, SALTWATER SYSTEM, PANORAMIC SCREEN ENCLOSURE, EXTENDED PAVER DECK, and PROFESSIONAL LANDSCAPING. Additional upgrades include FULLY PAID SOLAR PANELS, NEW AC COILS, SMART LIGHTING, LEVEL 2 EV CHARGER, and a 3-CAR GARAGE. As an added bonus, HOA guidelines allow for the ability to BUILD A PRIVATE DOCK, creating a rare opportunity to further enhance your LAKEFRONT LIFESTYLE. Located directly across from the future 5-acre community park, planned to feature playgrounds, basketball courts, walking trails, picnic pavilions, open green space, and recreational amenities, this home offers an exciting lifestyle enhancement just steps away. Another unique benefit is that all school pickup and drop-off traffic is routed through Atwater Bay Drive rather than directly in front of the home, helping maintain a quieter, more peaceful streetscape during school hours. Conveniently located near TOP-RATED SCHOOLS, SHOPPING, DINING, DISNEY, and major highways, this exceptional home offers luxury living at its finest.

9969 Lost Creek Drive, Winter Garden

$1,495,000

6 Beds ⋅ 6 Baths ⋅ Waterside/Johns Lake Ph 1 SubDv. ⋅ 34787 Zip Code

An Irreplaceable Gated Estate: Unmatched Scale, Double-Lot Privacy, & Private Oasis Behind the gates of the highly coveted Waterside community, 16614 Harbor Sail Way breaks the mold of standard luxury builds. This is not a high-density, cookie-cutter residence; it is an established, substantial family estate defined by an extraordinary sense of space, meticulous craftsmanship, and structural authority. Positioned beautifully on an expansive, premium lot that nearly doubles the community average, this rare property offers a refined lifestyle designed for those who value space to breathe, long-term permanence, and effortless entertaining. While typical Mansfield floor plans in the neighborhood occupy a standard lot, this home’s visionary owners secured the adjacent parcel, resulting in a commanding 14,973-square-foot footprint. This unique layout introduces a majestic private turning circle with dedicated parking for an additional six vehicles (bringing total driveway capacity to ten)—ideal for hosting executive gatherings or multi-generational families. Beyond the striking courtyard entry, the residence spans an impressive 4,882 square feet of meticulously maintained living space, delivering structural scale that effortlessly handles the demands of modern family life. The heart of the home centers on a dramatic great room bathed in natural light, seamlessly connecting to a gourmet kitchen equipped with premium finishes and gas cooking. Every corner of the main level emphasizes functional luxury, including a private home office, formal dining room, a secluded guest suite, and a magnificent primary sanctuary. Ascending to the second level reveals a sprawling, open flex room suspended over the main living area that opens to a fully enclosed, private balcony, creating an incredible architectural anchor. This level features four additional large bedrooms and media room, offering families the chance to spend time together, or unwind in complete peace. For ultimate daily convenience, a built-in central vacuum system services the ground floor of the home. While neighboring homes may provide "room for a future pool," this estate delivers the ultimate outdoor lifestyle immediately. The west-facing backyard is a private, sun-drenched sanctuary featuring a spectacular custom salt-water pool and integrated spa. Surrounded by extended paver decking and lush, manicured grassed areas made possible by the expanded double-lot footprint, this outdoor space offers complete privacy with no direct rear neighbors—perfect for enjoying vibrant Central Florida sunsets. Living in Waterside means enjoying a resort-style lifestyle with access to a premier clubhouse, fitness center and community pool. You are uniquely positioned just minutes from Horizon West’s top-rated schools (Hamlin Elementary/Middle), West Orange (High), the charm of downtown Winter Garden, major executive corridors (SR-429, Turnpike), and premier dining and shopping. This is more than a home; it is a strategic asset of scarcity, privacy, and generational quality. Schedule your private tour to experience it firsthand.

16614 Harbor Sail Way, Winter Garden

$1,375,000

4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 1a SubDv. ⋅ 34787 Zip Code

Now offered at $1,375,000 following a $124,000 price adjustment. This luxury residence presents an exceptional opportunity to own a beautifully designed home at its newly adjusted price. Rare opportunity to own an exceptional lakefront residence with a private dock and breathtaking panoramic water views in one of Winter Garden's premier resort-style communities. Offering approximately 4,663 square feet of living space, this impressive home features 4 bedrooms, 4 bathrooms, and a 3-car garage on a spectacular direct lakefront homesite. Designed to maximize the stunning waterfront setting, the home showcases soaring ceilings, elegant architectural details, expansive living spaces, and abundant natural light throughout. The gourmet kitchen features an oversized island, double ovens, walk-in pantry, and seamless flow into the main living areas, all positioned to capture beautiful lake views. The luxurious primary suite serves as a private retreat with direct access to a covered second-floor balcony overlooking the water. Additional indoor and outdoor living spaces, including a covered lanai, provide the perfect setting for entertaining or simply enjoying Florida's year-round lifestyle. Residents enjoy access to resort-style amenities including pools, clubhouse, fitness center, walking trails, and playgrounds. Conveniently located near shopping, dining, entertainment, and major roadways, this remarkable waterfront property offers luxury, privacy, and an unparalleled lakefront lifestyle.

8530 Bayview Crossing Drive, Winter Garden

$1,300,000

4 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code

Welcome to an exceptional residence where luxury, lifestyle, and location converge in one of Winter Garden’s most desirable communities. Situated on a hard to find oversized premium corner lot, this stunning 4-bedroom, 4-full bath home offers 3,424 square feet of thoughtfully designed living space, perfectly positioned to capture serene park views in the front and tranquil pond vistas in the rear. From the moment you arrive, the home’s elevated presence and expansive setting set the tone. Inside, you are greeted by a light-filled, open-concept layout designed for both elegant entertaining and everyday comfort. The spacious floor plan flows seamlessly, enhanced by refined finishes and generous living areas. At the heart of the home, the kitchen and great room spaces connect effortlessly to the outdoors, where your private resort-style retreat awaits, outdoor living at its finest! Step outside to your private POOL (built in 2022)—a true showpiece designed for relaxation and entertaining. The fully fenced backyard with a sleek metallic fence offers both privacy and unobstructed views, creating the perfect balance of security and openness. Whether hosting gatherings or enjoying a quiet evening, the backdrop of the pond and open skies delivers an unparalleled sense of tranquility. And as the sun sets, prepare for a truly magical experience—nightly views of the MAGIC KINGDOM FIREWORKS right from your backyard create a one-of-a-kind ambiance that elevates everyday living into something extraordinary. INTERIOR HIGHLIGHTS: 4 Bedrooms | 4 Full Bathrooms. A spacious DEN located in the first floor is currently set as a guest room, with the convenience of a full bathroom in the first floor with access to the pool. A spacious BONUS ROOM located on the second floor– ideal for a media room, office, or playroom. Expansive GREAT ROOM and entertaining areas including a STUDY SPACE off of the kitchen and a DINETTE SPACE. A thoughtfully designed layout with functional flow! Recent Update:A/C UNIT REPLACED in late 2025, offering peace of mind and energy efficiency for years to come. Park views from the front – providing openness and privacy. Pond views from the rear – creating a serene and picturesque backdrop. Oversized corner lot enhances curb appeal and outdoor space. This is more than just a home—it’s a lifestyle property that blends natural beauty, luxury amenities, and a prime location. From quiet mornings overlooking the pond to evenings watching Disney fireworks, every day here feels elevated.

9189 Busaco Park Way, Winter Garden

$1,299,000

5 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code

Welcome to 15554 Panther Lake Dr, a beautifully maintained residence located in the highly desirable Winter Garden community of Lakeshore Preserve. This spacious two-story 4345 sq ft home offers 5 bedrooms and 4.5 bathrooms with a thoughtfully designed layout that combines comfort, functionality, and style. One of the home’s standout features is the presence of two primary suites; one conveniently located on the first floor and another upstairs, providing exceptional flexibility for multigenerational living, guests, or private retreats.This exceptional home is being offered fully furnished, providing a truly move-in-ready opportunity. The open-concept living spaces are filled with natural light and designed for both everyday living and entertaining. With the kitchen connecting seamlessly to the dining and great room areas, this charming layout is perfect for hosting friends and family. After dinner, step outside to your own private backyard retreat, where the pool, fountains, fire pit, and outdoor entertaining areas create the perfect setting to enjoy Florida living year-round. Adding to the home’s appeal, it is equipped with a radiant barrier designed to help improve energy efficiency and reduce cooling costs, a valuable feature for enhanced comfort and long-term savings in the Florida climate. The home also brandishes spacious secondary bedrooms, abundant storage, a 2-car garage, and a meticulously maintained interior that reflects true pride of ownership throughout. One of this home's greatest features is its unbeatable location for families. Panther Lake Elementary School, a highly rated A school, is just behind the home, while Horizon High School is directly across the street. It's a rare opportunity to enjoy the convenience of top-rated schools just steps from your front door. Ideally situated just minutes from shopping and dining at Hamlin Town Center, major highways, and Walt Disney World Resort, this home offers both convenience and an exceptional lifestyle. Residents of Lakeshore Preserve enjoy resort-style amenities including a community pool, clubhouse, fitness center, playground, and scenic access to Panther Lake. A rare opportunity to own a spacious pool home with a flexible floor plan in one of Winter Garden’s most sought-after communities.

15554 Panther Lake Drive, Winter Garden

Homes for Sale in Winter Garden, FL Between $1,250,000 to $1,500,000

All Winter Garden, FL Homes for Sale Between $1,250,000 to $1,500,000

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