Homes for Sale Near West Orange High in Winter Garden - 102 homes

Remarks: One or more photo(s) has been virtually staged. Welcome to 15558 Sandfield Loop, a refreshed residence offering a turn-key lifestyle within one of Winter Garden’s most exclusive and hard-to-find GATED community. This house has been freshly updated from top to bottom, including new interior and exterior paint that makes the whole place feel brand new. The first thing you'll notice when you walk in is the massive, two-story high ceiling in the living area—it brings in tons of natural light and gives the home a great, airy feel. The kitchen has been fully redone with modern two-tone cabinets and beautiful quartz countertops. Throughout the home, you will find fresh paint and new flooring that perfectly complement the contemporary aesthetic. Situated within a highly-rated school zone, this MOVE IN READY property combines the security of a premier gated community with grand architectural features and stylish updates.

Listing is courtesy of: ORLANDO HIGHLAND REALTY LLC (561-385-7610)

Listing Agent: Xiaoli Lin (561-385-7610)

Remarks: Welcome to this fully renovated 3-bedroom, 2-bath home on an oversized 0.20-acre lot in one of Winter Garden’s growing corridors. This move-in ready property offers immediate livability with long-term upside. Recent upgrades include a new AC system and water heater (2026) and a roof replaced in 2019, minimizing near-term capital expenses. The home features updated interiors and a functional layout suited for both owner-occupants and investors. The large lot provides flexibility for outdoor use and potential future enhancements. Zoned R-4, the property may provide additional possibilities for expansion or income-producing use. Buyer to verify all zoning and development options with the city. Located just minutes from major highways, shopping, and ongoing development, this property is well-positioned for both convenience and future growth.

Listing is courtesy of: LIVE MVRK LLC (407-756-4563)

Listing Agent: Gabriel Flete (407-341-9663)

Remarks: Welcome to your opportunity to own in one of the most desirable locations near downtown Winter Garden—just off iconic Plant Street. This beautiful 3-bedroom, 2.5-bath home offers nearly 1,700 square feet of thoughtfully designed living space in an unbeatable setting. Step inside to an expansive great room featuring stylish wood-look tile and an open-concept layout that seamlessly connects the living, dining, and kitchen areas—perfect for entertaining. The kitchen is designed for both function and style, offering abundant stylish cabinetry, gorgeous backsplash, elegant gold hardware, granite countertops, gas stove and generous prep space. A screened courtyard with pavers creates a more private/secure outdoor retreat between the home and the detached 2-car garage. Whether you envision an outdoor lounge, garden oasis, or entertainment space, the possibilities are endless. Upstairs you will find upgraded- low maintenance flooring through out and your own private owner’s retreat. The spacious primary suite features a walk-in closet and an impressive ensuite bath designed to impress. Two additional bedrooms share a full bathroom, offering flexibility for guests, family, or a home office setup. A convenient half bath is located downstairs for visitors. Enjoy your summer months cooling off in the community which is located just a couple of minutes from your front door. This community is ideally positioned between the West Orange Trail Park and the Winter Garden Branch Library, and just minutes from the 429 for easy commuting. If you like to run or bike this home is the perfect place for you since it is located along the West Orange Trail. Walk—or hop on your golf cart—to downtown Winter Garden where you’ll enjoy the vibrant atmosphere of Plant Street Market, known for its local food vendors, craft brews, artisan goods, and year-round community events. Located close to the community pool and surrounded by everything that makes Winter Garden special, this home truly offers the lifestyle buyers are searching for. Lower utility bills since it's an inside unit, double pane windows and a tankless water heater. Schedule your private showing today and experience why this location is so highly sought after.

Listing is courtesy of: CORCORAN CONNECT LLC (407-953-9118)

Listing Agent: Milinda Knollinger (321-624-7384)

Remarks: Under contract-accepting backup offers. *Video Tour Available!* Experience the best of Florida living in the heart of Stoneybrook West, where resort-style amenities and a true sense of community come together. Behind 24-HOUR GUARD GATED ENTRANCE, you’ll find everything you need to live like you’re on vacation year-round—an Olympic-sized swimming POOL, splash zone, FITNESS CENTER, playground, tennis, basketball and pickleball courts, a fishing pier, plus a PRIVATE BOAT RAMP on Black Lake. Even better, the quarterly HOA INCLUDES SPECTRUM INTERNET AND CABLE, making life here as convenient as it is enjoyable. Tucked away on a quiet CUL-DE-SAC STREET with no through traffic, this home offers both privacy and charm from the moment you arrive. Warm curb appeal welcomes you inside to rich WOOD FLOORS and soaring ceilings that create a light, airy Florida feel. At the front of the home, the FORMAL LIVING AND DINING ROOMS provide flexible space for entertaining or working from home, highlighted by a welcoming staircase. Designed for gathering, the OPEN FLOOR PLAN seamlessly connects the family room and eat-in kitchen. The kitchen features abundant QUARTZ COUNTERTOPS, upgraded cabinetry, and a pantry to keep everything organized. Double sliding doors from both the kitchen and family room open to a SCREENED PATIO OVERLOOKING A PEACEFUL POND—no rear neighbors, just tranquil views and evening sunsets. Upstairs, you’ll find the bedrooms along with a convenient laundry room. The primary suite is spacious with wood floors, double sinks, quartz countertops, a water closet, and WALK-IN CLOSET. The RENOVATED SECOND BATHROOM offers a beautifully tiled shower and tub with a built-in shampoo niche. Generously sized secondary bedrooms feature deep closets for all your storage needs. Additional upgrades include a NEWER ROOF (2021), NEWER WATER HEATER (2024), ceiling fans throughout the home and patio, a convenient half bath downstairs, new irrigation panel, updated faucets and shower head in the primary bath, newer microwave and refrigerator, window blinds and exceptional storage throughout. This is more than a home—it’s your opportunity to embrace the Florida lifestyle, where sunny days, waterfront adventures, and a vibrant community are all right outside your door.

Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)

Listing Agent: Tennille Biggers (850-628-4455)

Remarks: QUICK MOVE IN!!! NEWLY BUILT Highly Desirable Community and Location!! Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from Historic Downtown Winter Garden. This Gated New Community features single-family homes on large homesites without a CDD. Step into the Coral Grand by Pulte Homes, where Luxury and Convenience seamlessly combine to create a Truly Elevated Living Experience. This Remarkable 4-Bedroom 3-Bathroom 1-Flex Room Home, Offers an Oversized Driveway and Corner Lot. The Chef-Inspired Kitchen Features Upgraded Dana White Cabinetry (Soft Close), Oversized Quarts Countertops, Undercabinet Lighting, and Whirlpool Stainless Steel Appliances with Exhaust Fan Exterior, Making Cooking a True Pleasure. The Kitchen seamlessly connects to the Café and Extended Gathering room, where a Sliding Glass Door opens to the Covered Lanai, Enhancing the flow of Indoor-Outdoor Living. The Loft area provides the perfect space to unwind, with two additional bedrooms and one bathroom complete the upper level. This Elegant Home is Equipped with a Smart Nest Thermostat, Smart Google Doorbell, ensuring your home is as connected as it is Beautiful. This home offers the perfect combination of Luxury, Convenience, and Modern Design—an ideal place to live and relax. This Split Floorplan Design of the Home and Laundry Room maximizes Privacy, Useful Space, and Peace. Residents also enjoy all the proximity to Shopping Plazas, Restaurants, Parks, and Entertainment this area is known for. Call NOW and Schedule a tour today!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Raymond Tong (954-940-1628)

Remarks: Perfectly positioned fronting one of Oakland Park’s picturesque green spaces, this exceptional home offers a rare opportunity to enjoy PARK-SIDE living in one of Winter Garden’s most celebrated communities. Oakland Park, a PARADE of HOMES award-winning neighborhood, is admired for its timeless architecture & inviting outdoor spaces that create a true sense of community. This beautifully designed Seaside floorplan blends classic charm with modern livability, offering 4 bedrooms, 3.5 baths, a STUDY, dining area, spacious loft, oversized garage, & FENCED yard. The primary suite is conveniently located on the main level, creating a peaceful retreat complete with a generous walk-in closet, a separate linen closet, & direct access to the laundry room, which has been enhanced with custom cabinetry for optimal storage & organization. Upstairs, the loft provides a versatile secondary living area—ideal for a media room or play space—accompanied by three additional bedrooms & two full baths, including one private en-suite. At the center of the home, the expansive kitchen is designed for both everyday living & effortless entertaining, enhanced with under cabinet lighting & tile backsplash. Abundant cabinetry & extensive counter space provide exceptional functionality, while the large island offers ample seating, making it the natural gathering place for family & guests alike. The adjoining dining area is equally impressive, featuring a dedicated buffet—perfect for hosting celebrations, holidays, or casual dinners. The home showcases rich WOOD flooring throughout the main living areas, adding warmth and sophistication, while soft carpeting in the bedrooms enhances comfort & tranquility. One of the home’s most captivating features is the inviting wraparound front porch, where French doors open to sweeping views of the beautifully maintained park. The home’s outdoor living continues in the screened rear porch, thoughtfully designed with retractable screens to maximize comfort & flexibility throughout the seasons. Beyond the porch, the backyard has been carefully curated as a private entertainment retreat. A paver patio anchors the space, complemented by a cozy FIRE-PIT, additional seating areas, & an outdoor kitchen featuring a built-in grill, mini fridge, & sink. Pet lovers will appreciate the dedicated dog area finished with low-maintenance artificial turf, creating a convenient & attractive space for four-legged family members. With its prime park-front location, versatile living spaces, & thoughtfully designed indoor-outdoor lifestyle, this home offers an exceptional blend of elegance, comfort, & community. Just a short GOLF CART ride away, you’ll find the charm and vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails, including access to the 22 mile long WEST ORANGE TRAIL. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Ashley Boyd (321-209-5540)

Remarks: Welcome to Southern Pines in the heart of Winter Garden! This clean and well-maintained 1-bedroom, 1-bath upstairs condo offers bright, open living with a rare combination of features you won’t often find in the community. Positioned on the upper level, the home enjoys enhanced privacy and abundant natural light with windows on both sides of the building, creating an airy and inviting atmosphere throughout the open-concept living and dining area. The kitchen flows seamlessly into the main living space and features granite countertops, ample storage, and all appliances convey with the sale — making this home truly move-in ready. Enjoy peaceful views overlooking the community tennis courts and resort-style pool. Downstairs, the attached 1-car garage and generous under-stair storage closet provide exceptional storage space — a true rarity within the neighborhood. Enjoy maintenance-free living, with HOA fees covering lawn care, cable, internet and water. Spend your weekends exploring Winter Garden Village, just 1.5 miles away, or immerse yourself in the charm of historic Downtown Winter Garden, filled with cozy cafés, boutique shops, farmers markets, and more. Outdoor enthusiasts will appreciate easy access to the West Orange Trail, perfect for biking, jogging, or leisurely strolls. Commuting is effortless with quick connections to the Florida Turnpike, SR 408, and SR 429. The gated Southern Pines community offers impressive amenities, with the pool, hot tub, and clubhouse located across the street. Additional features include a covered playground, movie theater, game room, office space, outdoor kitchen with grills, tennis court, indoor basketball and racquetball courts, sand volleyball, and even a car wash station. Don’t miss your opportunity to own in one of Winter Garden’s most convenient and amenity-rich communities. Schedule your showing today.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Anna Gay Hunter (407-446-9878)

Remarks: Motivated seller – bring your offers! Location, Location, Location! Don't miss the opportunity to own this beautiful and cozy 4-bedroom, 4-bath home featuring thoughtfully designed living spaces that combine comfort, functionality, and inviting charm. The main floor features all four bedrooms, offering convenience and privacy for everyday living. Upstairs, you’ll find a spacious bonus room with a full bathroom, perfect for a media room, game room, home office, or additional living space. This is the only area of the home with carpet, creating a comfortable and cozy environment for relaxation or entertainment. Throughout the main living areas, the home features luxury vinyl flooring, providing durability and a modern look while enhancing the overall warmth of the home. The kitchen opens beautifully to the main living area, creating a welcoming space for gathering with family and friends. The kitchen cabinets were recently refinished and painted, giving the kitchen a refreshed and updated appearance. Step outside and enjoy the screen-enclosed patio, offering a comfortable outdoor space where you can relax and enjoy Florida living with added protection from insects. The home also features attractive landscaping and brick pavers on the driveway and entrance, creating great curb appeal and a welcoming first impression. Additionally, the property includes solar panels, contributing to improved energy efficiency. This home offers a warm and inviting atmosphere with well-distributed spaces that make it perfect for both everyday living and entertaining. Schedule your private showing today and come experience the comfort and charm this home has to offer in a perfect location!

Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)

Listing Agent: Marcelle Da Silva Sampaio (407-369-3621)

Remarks: **NOW FHA AVAILABLE** DISCOVER THE SERENE BEAUTY OF THIS STUNNING HOME! GORGEOUS 3-BEDROOM, 1-BATHROOM, 1-CARPORT HOME boasting a SPACIOUS FLOOR PLAN that effortlessly blends functionality with modern style. From the moment you step inside, you’ll be greeted by an OPEN-CONCEPT LIVING AREA filled with NATURAL LIGHT, creating a warm and inviting atmosphere. Cook like a pro in the NEWER KITCHEN featuring NEW QUARTZ COUNTERTOPS and SLEEK STAINLESS STEEL APPLIANCES—perfect for culinary enthusiasts. This home is LOADED WITH UPGRADES, including: New Roof with 30-Year Shingles, New HVAC System, New Laminate Flooring Throughout, Renovated Bathrooms, Fresh Interior & Exterior Paint, New Light Fixtures, Faucets, Toilets, Interior Doors, and Closet Doors. CONVENIENTLY LOCATED near all major highways, shopping, restaurants, and entertainment—this move-in-ready home truly has it all! All measurements are approximate and should be verified by the buyer for accuracy. Virtual Staging was added to some of the pictures.

Listing is courtesy of: IHOME REALTY FL LLC (407-730-9971)

Listing Agent: Karen Sweat (407-730-9971)

Remarks: COMPLETELY REMODELED WATERFRONT HOUSE WITH PRIVATE DOCK AND BOAT LIFT ON THE LAGERST LAKE IN CENTRAL FLORIDA!!! MOTIVATED SELLER! Experience the ultimate in LAKEFRONT living with this stunning, turnkey home on Lake Apopka in Winter Garden, in the heart of a highly desirable GOLF CART DISTRICT. Boasting over 3,700 sq. ft. of beautifully remodeled living space, this 4-bedroom, 3.5-bathroom residence combines modern luxury with waterfront charm, offering breathtaking sunrise and sunset views every day. Every inch of this home has been meticulously upgraded with nearly $450,000 invested in 2024 renovations, creating a move-in-ready oasis with high ceilings, spacious open-concept living, and designer finishes throughout. Gorgeous porcelain tile and hardwood floors flow seamlessly across two stories, complemented by abundant natural light from all-new, upgraded windows. The gourmet kitchen is a chef’s dream, featuring quartz countertops, a large island with built-in cabinetry, stainless steel appliances, a backlit quartz bar, and a modern backsplash. Entertain effortlessly in the expansive dining room and living room, framing incredible LAKE APOPKA VIEWS, GORGEOUS SUNRISES AND BREATHTAKING SUNSETS! The master suite is a serene retreat with two walk-in closets, an oversized Jacuzzi bathroom, and stunning water vistas. Each bedroom boasts lake views, while a second-floor guest bedroom offers privacy, a separate bathroom, and noise-reducing flooring—perfect for another master bedroom, home theater or office. A dedicated office/den at the entrance is ideal for remote work or study. Outdoor living is exceptional with two enclosed and screened patios on the first and second floors, providing panoramic lake views. Boaters will love the expansive deep-water dock with a boat lift and the fun Margaritaville-themed bar. The backyard features a newly resurfaced saltwater pool with a new pump, new pool filter, a fully fenced private yard, fruit trees and mature, landscaped greenery creating a private oasis. Additional highlights include new windows, new HVAC, new SOLAR PANELS (keeping the monthly ELECTRIC BILL BELOW $50), smart thermostat, upgraded irrigation, and a two-car garage with built-ins. Located in a quiet, family-friendly gated community with golf-cart-friendly streets and direct access to the scenic West Orange Trail. Enjoy Winter Garden’s historic downtown just minutes away, with A-rated schools, shopping, dining, and the famous weekend farmers market. Only 20 minutes to Downtown Orlando and close to Disney, Universal, and major highways without the traffic. There are six highly rated Golf Clubs within a 5-mile radius. This is more than a home—it’s a boater’s and fisherman’s paradise, a lakefront retreat, and a perfect family haven all in one. Don’t miss this rare opportunity to own a completely remodeled luxury waterfront home with unmatched views and lifestyle amenities on Lake Apopka, offering over 30,000 acres of endless water fun! Price can be reduced by $40,000 if the buyer is willing to assume a solar panel loan at 3.49%!

Listing is courtesy of: KELLER WILLIAMS EAGLE REALTY (305-757-1700)

Listing Agent: Marina Kostic (240-421-6466)

Remarks: BOM. Buyer decided against stairs. There is a specific kind of silence that exists only within the gated sanctuary of Canopy Oaks. It is the sound of ancient oak leaves stirring in a gentle breeze & the distant, rhythmic splash of a stone fountain. Here, the recipient of the Parade of Homes Grand Award stands as a magnificent testament to what happens when timeless Italian architecture is reimagined for a modern lifestyle. This is not merely a residence. It is a legacy of vertical liberation, a home that breathes with you, scales with your ambitions, and cradles your quietest moments in an embrace of stone and iron. Your journey begins at the threshold of 8-foot, solid double-entry doors. As they swing open, the frantic pace of Central Florida fades, replaced by a two-story foyer that commands immediate respect. A hand forged iron staircase sweeps upward in a graceful arc, mirrored by the delicate charm of a Juliette balcony that suggests a life lived with a touch of Mediterranean flair. Every inch of this grand entrance is a curated experience, designed to transition you into a realm of meticulously crafted prestige where every shadow and light well has been considered. For those who view cooking as a performance art, the professional-grade kitchen is your stage. High-end Kitchen Aid appliances and a natural gas cooktop meet the warmth of artisanal design. The 42-inch upper cabinetry and a hidden walk-in pantry ensure the visual continuity remains unbroken. At the center sits a massive prep island with integrated beverage refrigeration, designed specifically for the art of hosting. Here, the boundary between chef & guest is delightfully blurred. Nearby, the home reveals its most enchanting secret, the drop-down wine cellar. Behind a hand-forged iron gate lies a space that transports you directly to a cobblestone alleyway in Tuscany. With label-forward shelving casting a museum-quality glow & a quaint bistro table within, it evokes the feeling of a private corner in a centuries-old Italian eatery. It is the ultimate setting for an evening pour, a space where time slows down & the modern world feels a thousand miles away. The first-floor owner’s suite is a masterclass in personal seclusion. By design, this space serves as a dedicated haven of quietude, featuring soaring tray ceilings & an atmosphere of total stillness. The spa-inspired bath, featuring a frameless glass walk-through shower & a free-standing soaking tub, offers a daily ritual of total restoration. As you ascend, the lifestyle shifts toward entertainment. The dedicated theater room stands ready for premiere nights, offering a dark, immersive escape. Adjacent, the versatile gathering room opens onto a private balcony overlooking the shimmering resort-style pool & the vast, permanent conservation area. With no rear neighbors, your view is an unbroken tapestry of natural beauty. The outdoor living area features a resort-style pool & spa framed by water/fire bowls & a rainfall pergola. With a full summer kitchen & a backyard that merges into conservation, your privacy is absolute. Enjoy the nightly glow of nearby fireworks from your peaceful terrace, surrounded by the scent of night-blooming jasmine. Strategically along the medical corridor, you are minutes from AdventHealth, Orlando Health & the soul of Winter Garden. Backed by a whole-house natural gas generator & water purification, this home offers security & beauty. Welcome home. Check out the video tour!

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)

Listing Agent: Sean Spencer (407-383-0707)

Remarks: *Seller is willing to contribute up to $5,000 towards interest rate buy down or closing costs*. Experience refined Florida living in this beautifully upgraded Winter Garden residence in the highly sought after gated Bradford Creek community. Thoughtfully designed for both everyday comfort and elevated entertaining, your new home has a rare and highly desirable floor plan with all 4 bedrooms on the main level, combining convenience with timeless style. The spacious primary suite serves as a private retreat with a luxurious ensuite bath featuring a soaking tub and waterfall shower. Two secondary bedrooms with private ensuite baths including one second master bedroom ideal for guests, multigenerational living, or private office space. Upstairs, the expansive bonus room/loft offers endless flexibility for a media room, game room, fitness studio with a large closet that can be converted to a 5th bathroom. Step outside to your own resort-inspired escape with all the bells and whistles to create exceptional setting for relaxing or entertaining year-round. High-end upgrades include the screened travertine lanai, saltwater gas-heated pool, oversized custom saltwater spa, and fully equipped outdoor kitchen with built-in grill and Big Green Egg. Elegant architectural details include crown molding, wainscoting, coffered ceilings, and designer wood-look ceramic tile creating a polished and sophisticated feel. The extended gourmet kitchen is a standout feature, appointed with white shaker cabinetry, granite countertops, double ovens, pot filler, and a premium gas cooktop, making it as functional as it is beautiful. Set on a .30-acre lot with an extended paved driveway conveniently located near Downtown Winter Garden, The Grove, SR-429, Florida’s Turnpike, and Highway 50, this is an opportunity to own a truly distinctive home in one of Central Florida’s most desirable areas. For added modern convenience, the home also includes an EMA outlet for electric car charging, seamlessly supporting today’s lifestyle. Schedule your appointment today and bring your offers.

Listing is courtesy of: COLDWELL BANKER REALTY (813-253-2444)

Listing Agent: Gislene Moorman (407-694-2246)

Remarks: Under contract-accepting backup offers. Located in the Rare Lake Avalon Rural Settlement where oversized lots and protected rural zoning create one of Winter Garden’s last truly rare, low-density communities. Welcome to this fully remodeled, modern lakefront retreat on the shores of Lake Avalon, offering the perfect balance of sophistication, privacy, and convenience. Situated on almost 1.5 acres of fenced, irrigated land, this stunning single-story home features 3 bedrooms, 3.5 baths, and approximately 2,400 sq. ft. of living space with an attached 2-car garage—all meticulously updated with high-end finishes throughout. Step inside to an open, airy floor plan filled with natural light and luxury vinyl wood flooring that flows seamlessly from room to room. The gourmet kitchen is the heart of the home, featuring a dramatic quartz waterfall island, soft-close cabinetry, elegant gold accent hardware, and premium GE Cafe Matte white kitchen appliances, all included, along with washer and dryer. The kitchen overlooks a spacious dining area and family room, perfect for entertaining or relaxing by the wood-burning fireplace while taking in serene views of the backyard and lake beyond. The primary suite is a luxurious private retreat with two walk-in closets, direct access to the back porch, and a spa-style bathroom featuring double vanities, a beautifully tiled walk-in shower, and a freestanding soaking tub. The two additional bedrooms each have their own custom; modern bathrooms designed with premium tile and fixtures. Outside, the possibilities are endless. Enjoy the peaceful setting surrounded by mature trees, a large fire pit area, and a private pathway leading to your own dock—perfect for skiing, fishing, kayaking, or simply watching the sunset over Lake Avalon. Lake Avalon is a freshwater lake of about 184 acres in size and the lake supports fish species including largemouth bass and blue catfish. The property offers ample space for a boat, RV, or multiple vehicles along the extended paved driveway, with no HOA restrictions, allowing you the freedom to add a guest house, barn, or workshop if desired. Major updates include: Roof (2021), A/C (2021), Plumbing (2019), Water Heater (2020), Windows (2019), Septic (2019 and clean out 2025), Well Pump (2025), Water Softener & Purification System (2021). The home operates on well and septic, ensuring low utility costs and self-sufficiency. Located just minutes from Historic Downtown Winter Garden, Fowler’s Grove, and Hamlin Town Center, you’ll enjoy the best of both worlds—city conveniences with a peaceful, country feel. This home truly has it all: acreage, lake access, privacy, and luxurious modern design—all move-in ready for the holidays. There’s simply nothing else like it on the market. Come experience lakefront living at its finest in one of Central Florida’s most desirable locations. Call for your private tour today!

Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)

Listing Agent: Denise Gregorie (407-463-0080)

Remarks: One or more photo(s) has been virtually staged. Ideally located in the heart of Winter Garden, this home offers 3,474 sq. ft. of living space and exceptional walkability just steps from Winter Garden Village’s shopping, dining, and everyday conveniences. Recent updates include new carpet and fresh interior and exterior paint. The flexible floor plan features five bedrooms, three full bathrooms, and a kitchen with 42-inch upper cabinets, granite countertops, and an open layout to the family room with a large eat-in area. Stone Crest community amenities include a clubhouse, pool, tennis/pickleball courts, playground, and a scenic walking trail around a tranquil pond. With close proximity to AdventHealth, major highways, historic downtown Winter Garden, the West Orange Trail, and top-rated schools, this property provides excellent convenience and connectivity.

Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)

Listing Agent: Joseph Doher (407-203-0007)

Remarks: One or more photo(s) has been virtually staged. NEW ROOF (2025) ~ TWO NEW A/C UNITS (2024) ~ and a NEW WATER HEATER (2024) headline this exceptional LAKEFRONT ESTATE on Black Lake, where recent RENOVATIONS and thoughtful design have transformed the home into a must see retreat designed to impress! Ideally situated behind the gates of Bay Isle in Winter Garden, this remarkable home is the cherry on top of 6.44 ACRES surrounded by lush mature trees and sweeping LAKE VIEWS, creating a peaceful personal oasis just minutes from everything. A paver driveway and COURTYARD ENTRANCE invite you into the residence, complemented by a split 3-car garage and beautiful architectural details that set the tone for what awaits inside. Spanning OVER 4,000 SQ FT of curated living space, the home blends timeless craftsmanship with a fresh, modern edge. Sleek PORCELAIN TILE and rich WOOD FLOORS flow throughout, while intricate DESIGN WORK and CUSTOM BUILT-INS add character and sophistication from floor to ceiling. Designed with both everyday living and entertaining in mind, the layout offers MULTIPLE LIVING AREAS & FLEX SPACES, and formal living and dining rooms, all positioned to maximize NATURAL LIGHT and capture the home’s breathtaking water views. Walls of windows pull the outdoors in, creating a light-filled atmosphere that highlights the beauty of the surrounding landscape! At the heart of the home, the GOURMET KITCHEN delivers everything a home chef could want and more. Outfitted with a gas range, gas oven, waterfall island, dual pantries for abundant storage, and a rare Doyon Etuve Proofer, the space is as functional as it is impressive, easily supporting everything from quiet dinners to large gatherings. Your MAIN FLOOR OWNER’S SUITE is a true retreat with tranquil views of Black Lake, a sitting area, a dedicated dressing space, and a beautifully designed modern en-suite bath that feels straight out of a home magazine. Throughout the rest of the home, additional bedrooms and flexible spaces offer endless possibilities for guests, offices, hobbies, or creative pursuits. Step outside and the lake lifestyle truly comes to life. MULTIPLE OUTDOOR LIVING SPACES invite you to relax, entertain, or simply take in the scenery, while the PRIVATE DOCK on Black Lake makes it easy to bring your boat and enjoy everything lakefront living has to offer. Despite the sense of seclusion, this home remains incredibly convenient to daily life. Shopping, dining, and major roadways including SR-429 are just minutes away, placing you close to Winter Garden’s vibrant charm, area attractions, and world-famous theme parks. Elegance personified, this extraordinary home delivers the privacy, style, and space you have been searching for. Bring your boat, embrace the lake life, and discover the lifestyle waiting for you in Bay Isle!

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. One or more photos have been Virtually Staged. I'm excited to share details about a well-appointed executive home in the highly sought-after Deerfield Place Subdivision. This rare and spacious residence features 5 bedrooms and 4 bathrooms, encompassing over 3,400 square feet. The downstairs area includes a bedroom and full bath, a formal dining room, a formal sitting room, and a generous family area. The home also boasts beautiful wood laminate flooring throughout, an oversized kitchen, and a huge upstairs bonus room. The private, expansive master suite offers a comfortable sitting area and an oversized, spa-like bath, providing ample space for relaxation. Recent upgrades to the home include a new roof in 2020, a new refrigerator, and new laminate flooring in both the dining room and formal living area. The location is truly exceptional, offering convenient access to the Winter Garden Village Shopping District and the charming Winter Garden Downtown area. Please note that room sizes are approximate. This is truly a wonderful area to call home.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Barry Stephens (407-547-6500)

Remarks: Gorgeous pool home in Cypress Reserve featuring a private office, loft/game room, theater room, and over 4,100 sq ft with a 3-car garage. This stunning 4-bedroom, 3.5-bath residence offers thoughtfully designed living space that blends elegance, comfort, and functionality—delivering an exceptional lifestyle in one of Winter Garden’s most sought-after communities. From the moment you enter, soaring 20-foot ceilings, expansive windows, and an abundance of natural light greet you. A grand staircase and balcony create a striking focal point, anchoring the open-concept living area. The entry features formal living and dining spaces, along with a private office with French doors—ideal for working from home. At the heart of the home is a beautifully appointed gourmet kitchen, designed for both everyday living and entertaining. Highlights include a gas cooktop, built-in convection oven and microwave, pot filler, elegant backsplash, oversized center island, and extended cabinetry with ample storage—all overlooking the main living area and pool. The spacious primary suite is conveniently located on the main floor and features tray ceilings and a versatile sitting area—ideal for a secondary office, fitness space, or private retreat. The oversized custom walk-in closet is a standout, while the luxurious primary bath offers a large walk-in shower with a rain shower head, dual vanities, a soaking tub, and abundant cabinetry. Upstairs, you’ll find a generous loft, a dedicated media/theater room, and three additional bedrooms, including a Jack-and-Jill layout with walk-in closets. The flexible floor plan offers endless possibilities, with the loft or media room easily convertible into an additional bedroom. Step outside to your backyard retreat featuring a screened-in, heated saltwater pool with sun shelf, an expansive paver patio, and plenty of space for outdoor entertaining or relaxing in the Florida sunshine. With HOA green space behind the home, you’ll enjoy a more open feel and peaceful views. Additional highlights include 8-foot doors and high ceilings throughout, a tankless water heater, a spacious laundry room with utility sink and storage, oversized under-stair storage, and beautiful curb appeal with low-maintenance landscaping. Ideally located within walking distance to highly rated SunRidge Elementary and Middle School, and just minutes from downtown Winter Garden, Winter Garden Village, SR 429, Florida’s Turnpike, I-4, Downtown Orlando, Orlando International Airport, and nearby attractions including Walt Disney World. Outdoor enthusiasts will love the proximity to the West Orange Trail and Tucker Ranch Recreation and Nature Complex, offering over 300 acres of scenic trails, green space, and outdoor recreation. Residents of Cypress Reserve also enjoy a community pool and playground with a low HOA. This exceptional home truly has it all—luxury, space, versatility, and an unbeatable location. Schedule your private showing today!

Listing is courtesy of: INFINITY REALTY GROUP LLC (407-234-2256)

Listing Agent: Deb Schroeder (407-234-2256)

Remarks: You'll fall in love with this ONE STORY, Beautiful and Comfortable Winter Garden POOL home Featuring 4 Bedrooms, 2.5 Bathrooms, and Approximately 2200 Sf of Living Space! The saltwater pool is fairly new, added in 2020, with Pebbletech surface and screen enclosure, just off the covered Lanai. Inside the fenced back yard is also a large pavers area for relaxing at your firepit. The home has amazing amenities: 18" Ceramic tile floors in the living areas, Laminate Wood flooring in all bedrooms, Mosaic Inlays, and French Doors to the Formal Dining Room (currently used as an office) and also to the Formal Living room or Den. The Gourmet Kitchen is a focal point that includes Custom Fans, Pendant Lighting, and Volume Ceilings and comes complete with All Stainless Steel Appliances (Smart Refrigerator, Under Counter Microwave), a Gas Range, Wall-mount pot filler, Granite Countertops, 42" Wood Cabinets, Huge Center Island, Decorative Backsplash, and Large Eat-in area with Bench Seating. The Family Room open to the Kitchen is accented with Natural Stacked Stone, Wall Sconces, A Napoleon Wall electric Fireplace and more. AT&T is currently installing Fiber in the neighborhood, i.e., bandwidth to get 1G will be low priced and provide amazing internet connections! This great home is located less than a mile from West Orange High School and walking distance to YMCA. Enjoy the nearby Winter Garden Village shopping and restaurants. Easy commute via the Turnpike and Toll Roads to Downtown Orlando, Disney, Universal, and Orlando airport. Call to see it today!

Listing is courtesy of: WATSON REALTY CORP (407-298-8800)

Listing Agent: Lois Ann Cox, Pa (407-666-8452)

Remarks: Welcome to beautiful Winter Garden. Check out this exceptional 5-bedroom, 3-bathroom home is located in a gated community that blends comfort with a friendly neighborhood atmosphere. Thoughtfully designed, the home features four bedrooms upstairs and a flexible downstairs bedroom ideal for guests or a home office. The spacious primary suite serves as a private escape, complete with a soaking tub, separate shower, and ample room to relax. Upstairs, two expansive loft areas provide endless possibilities—perfect for a home gym, media room, play space, or additional living area. The main level boasts formal living and dining rooms, along with a large family room that opens through sliding doors to a private pool retreat with two paved seating areas, ideal for entertaining or unwinding. An open floor plan, elegant dual-entry wooden staircase, and stainless steel appliances add to the home’s appeal. Offering generous space, charming details, and a peaceful yet convenient location, this home captures the best of Florida living—schedule your showing before it’s gone.

Listing is courtesy of: HP GLOBAL REALTY LLC (407-925-6780)

Listing Agent: Heron Patel (407-925-6780)

Remarks: One Photo has been virtually staged with furniture. You found it!! Beauty in Winter Garden! Sought after location near downtown Winter Garden! This Windtree 2/2 condo on the 2nd floor has been totally & BEAUTIFULLY REMODELED in 2026 as follows! BRAND New Wood laminate flooring in living room & bedrooms. Kitchen has BRAND NEW farmhouse porcelain sink with floating butcher block shelves, shaker moss cabinets with brushed gold handles and faucet & exquisite quartz counter tops with marble herringbone backsplash. BRAND NEW Frigidaire stainless steel appliances. 3k in upgrades for recessed lighting. BRAND NEW Frigidaire Stackable washer & dryer with convenient according door being installed as well! Unit has own private storage under stairs (approx. 4X9 perfect for bicycles etc.) Community Pool & basketball court. Easy access to 408,429, FL. Turnpike, Disney, Universal and downtown Orlando.

Listing is courtesy of: WATSON REALTY CORP (407-298-8800)

Listing Agent: Rick Evans, Ii (407-538-9295)