Homes for Sale Near West Orange High in Winter Garden - 163 homes

Remarks: Welcome to 13822 Jomatt Loop! This stunning home offers 4 spacious bedrooms, 3 full bathrooms, a bonus loft space, private office and a 3 car garage off of an expansive driveway, all perfectly situated on an OVERSIZED FULLY FENCED LOT. Designed for both comfort and entertaining, the open-concept floor plan features generous living and dining spaces filled with natural light, and was just freshly painted throughout. The primary bedroom is located on the first floor and features his and hers walk in closets with CUSTOM BUILT INS, dual vanity spaces, a free-standing soaker tub, and spa like shower. Located on the second level is a large bonus room that's perfect for kids to play, a movie room, game room, and so much more. Step back outside to your personal backyard oasis where you can enjoy year-round Florida living with a heated sparkling pool and spa that's peacefully nestled between lush landscaping and a fully fenced yard. The expansive covered lanai is enhanced by a stunning outdoor kitchen by Paradise Grills, ideal for hosting gatherings, weekend barbecues, or simply unwinding at sunset. Additional upgrades include GAS APPLIANCES, custom living room built in entertainment center, automated pool pump, and various other thoughtful finishes throughout that elevate both style and function. This home is zoned for A-rated schools including Sunridge Elementary School and Sunridge Middle School, making it an exceptional choice for families seeking top-tier education options. Schedule your showing today! With its rare oversized conservation lot, luxury outdoor living, and prime location, this home truly checks every box. Schedule your private showing today and experience the lifestyle you’ve been waiting for.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Jenna Palmero (407-697-8727)

Remarks: Under contract-accepting backup offers. PRICE IMPROVEMENT!! Set within a gated community, Black Lake Park, just moments from Winter Garden Village - This beautifully maintained corner-lot residence offers a rare blend of everyday convenience and true lake-life access. A standout feature of the community is the PRIVATE BOAT RAMP and dedicated boat parking, providing direct entry to Black Lake — an exceptional amenity seldom found so close to town. The home itself has been thoughtfully cared for and updated, featuring a 2022 roof, fully fenced backyard, and an open, airy floor plan designed for both comfort and entertaining. High ceilings enhance the sense of space, while the primary suite serves as a private retreat with two walk-in closets and generous proportions throughout. Ideally located near top local restaurants, shopping, and entertainment, this home is just a five-minute drive to historic Plant Street in downtown Winter Garden and offers easy access to major highways for a seamless commute. Whether enjoying waterfront weekends, dining out nearby, or relaxing at home, this property delivers a lifestyle that is as convenient as it is distinctive.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Heather Spirazza (407-757-6022)

Remarks: ***Seller to offer up to $17,000 toward buyer's closing cost & or rate buy down.*** There is a distinct rhythm to life in Oakland Park that cannot be replicated anywhere else in Central Florida. It is a refined balance of Old Florida charm and modern luxury, where tree-lined streets, curated green spaces, and intentional design create a true sense of place. As you enter the community, everything feels elevated and thoughtfully composed, with the 22-mile West Orange Trail serving as the heartbeat that connects residents to both nature and one another. At 931 Kylee Alley, this lifestyle is fully realized. Positioned on a prominent corner lot, this David Weekley Stoneybrook residence showcases timeless architecture with a clean, sophisticated presence. One of the greatest luxuries here is the ease of ownership. The homeowners' association provides full landscaping maintenance, allowing the property to remain in pristine condition without demanding your time. Your weekends are yours to enjoy, not manage. Inside, the home immediately impresses with intentional sightlines and natural light. Built in 2022, the design feels both current and enduring. Soaring ceilings and expansive windows, complemented by custom plantation shutters, create a bright yet grounded atmosphere. The gourmet kitchen anchors the home, featuring an oversized island with sleek, solid surface countertops that serve as the perfect setting for gathering, entertaining, or everyday living. The floor plan is designed for both connection and privacy. The main level offers a flexible and refined space that can function as a guest suite or executive-style home office. Upstairs, the private quarters provide a peaceful retreat. The primary suite is expansive and serene, complete with a spa-inspired bath designed for relaxation at the end of the day. Living here means immediate access to the West Orange Trail and the best of Winter Garden. Bike to Plant Street, enjoy the Saturday Farmers Market, or simply take in the charm of one of Central Florida’s most sought-after destinations. Within Oakland Park, residents enjoy resort-style amenities, including multiple pools, a clubhouse, and a dog park, all contributing to a true lock-and-leave lifestyle. From an investment perspective, this property stands out. It offers an exceptional price per square foot for Oakland Park, with pricing thoughtfully adjusted to reflect the opportunity for upstairs flooring customization. In a community where demand continues to outpace supply, especially for newer construction on premium corner lots, this home represents both immediate value and long-term upside. 931 Kylee Alley is more than a home. It is a strategic acquisition within one of Winter Garden’s most desirable communities.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Matthew Mckee (407-948-0658)

Remarks: Located in the highly desirable gated community of Glynwood in Winter Garden, this spacious 5-bedroom, 4-bath pool home offers over 3,500 square feet of living space on a private cul-de-sac lot. The versatile floor plan features a first-floor owner's suite, dedicated office/den, formal and casual living areas, and an upstairs bonus/media room with an additional bedroom and bath—ideal for guests, multi-generational living, or a home theater. The screened pool and spa create a private backyard retreat, while the 3-car garage (AC by Modern Wall Unit and Upgraded Garage Floor Coating) provides ample storage and parking. Residents enjoy access to community amenities including a pool, tennis courts, playground, and gated entry. Conveniently located near Winter Garden Village, historic downtown Winter Garden, major highways, shopping, dining, and area attractions.

Listing is courtesy of: CHOICEPOINTE REALTY, INC. (888-246-5758)

Listing Agent: Mary Dees (407-468-8285)

Remarks: Virtually Staged. One or more photos are virtually staged. Location. Luxury. Architectural character. Welcome to The Sanibel, affectionately known as “The Castle,” an award-winning home just minutes from the charm and energy of Historic Downtown Winter Garden. This stunning residence blends timeless Italian-inspired architecture with modern comforts, creating a home that feels both elegant and inviting. From the moment you arrive, the home makes a memorable first impression with its arched wood double doors, custom soffit lighting, and classic concrete tile roof. Step inside and you’re greeted by soaring ceilings, detailed beams, and crown molding that add warmth and sophistication to the open-concept living spaces—perfect for both everyday living and entertaining. The gourmet kitchen is designed to impress, featuring premium KitchenAid appliances, a natural gas cooktop, built-in refrigerator, 42” custom cabinetry, a hidden walk-in pantry, and a reverse osmosis water system. Whether hosting guests or enjoying a quiet night at home, this kitchen is the heart of it all. The first floor offers exceptional flexibility with a private office and a Junior Owner’s Suite—ideal for guests or multi-generational living. Upstairs, the primary suite becomes your personal retreat with a unique round spa-inspired bathroom, oversized walk-in closet, wet bar, and access to a private balcony. Two additional en-suite bedrooms, a loft, and an upstairs laundry room complete the second level. Step outside and enjoy multiple spaces designed for relaxing and entertaining, including Trex-decked balconies, a summer kitchen, and a peaceful fountain feature. Additional highlights include surround sound wiring, a whole-home generator, and thoughtful upgrades throughout the home. Beyond the property itself, the location truly sets this home apart. You’re just minutes from Downtown Winter Garden’s award-winning farmers market, vibrant restaurants, charming boutiques, scenic parks, and top-rated schools—with easy access to major highways for commuting throughout Central Florida. Recognized as Florida’s Best Model Home by the SEBC Excel Awards, The Sanibel offers a rare opportunity to own a home that combines architectural distinction, luxury features, and an unbeatable Winter Garden lifestyle. Note: One image includes a virtually added pool to illustrate potential backyard possibilities.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)

Remarks: Don't miss this opportunity to own a well-maintained townhome in the sought-after gated community of Tucker Oaks. Featuring 3 bedrooms, 2.5 bathrooms, a 2-car garage, this home offers the perfect blend of comfort, convenience, and value. The open floor plan provides spacious living and dining areas, ideal for both everyday living and entertaining. A major recent improvement includes a roof installed in 2025, offering added peace of mind for years to come. Residents enjoy an array of community amenities, including a clubhouse, community pool, park, and playground. Ideally located just minutes from Historic Downtown Winter Garden, the West Orange Trail, shopping, dining, and major commuter routes including SR 429 and the Florida Turnpike, this home offers low-maintenance living with convenient access to everything Winter Garden has to offer.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Amy Moline (407-506-7447)

Remarks: Under contract-accepting backup offers. Welcome to your opportunity to own in one of the most desirable locations near downtown Winter Garden—just off iconic Heritage at Plant Street in the GOLF CART DISTRICT. 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, NEW Refrigerator, NEW microwave, NEW dishwasher, 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 POOL 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 Instant Hot Gas 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: Welcome to a life beautifully lived. Situated on a premier corner lot in Oakland Park, Winter Garden's golf cart community, this exceptional residence blends thoughtful design, effortless indoor-outdoor living, & a private tropical retreat. Freshly redesigned professional landscaping with premium weed barrier, smart irrigation, app control, & a mature Medjool date palm creates stunning curb appeal. A custom front door opens to a partially screened wraparound front porch, perfect for morning coffee or evening chats. Inside, rich hardwood floors span the main level, complemented by abundant natural light, crown molding, plantation shutters, designer lighting, brass floor outlets in the living room & office, and ceiling fans throughout. The kitchen features granite countertops, a farmhouse sink, stainless steel appliances, tile backsplash, under-cabinet lighting, a beverage refrigerator, & a new Bosch dishwasher and microwave (2023). Open to the living & dining areas, it overlooks the front porch & connects seamlessly to outdoor living through French doors. A flexible front room serves as an office, study, or playroom. A powder room serves guests. The first-floor owner's suite overlooks the pool & offers dual granite vanities, a spa-style walk-in shower, linen storage, custom California Closets, & direct laundry room access. Upstairs, hardwood flooring continues throughout 3 spacious bedrooms, including one en-suite, plus two full baths and a generous loft ideal for theater, fitness, playroom, or guest retreat. A whole-home Generac natural gas generator keeps lights, air conditioning, & appliances running during outages. Step outside to one of Oakland Park's rare full-size Jandy-iAqualink-controlled saltwater pool & spa. The pool measures approximately 12' x 30' with depths from 3' to 5' & features an 8' x 12' sun shelf with bubbling fountain and umbrella sleeve. The approximately 6' x 8' spa includes four therapy jets and heats in 20-30 minutes. Equipment includes a 2.7 HP Jandy Variable-Speed Energy-Efficient Pump & Jandy 400,000 BTU natural gas heater. A travertine pool deck, oversized covered rear porch, vinyl-fenced yard with dual gates, & three-car garage with built-in storage racks complete the outdoor experience. Oakland Park offers a waterfront, golf-cart-approved lifestyle with two resort-style pools, a clubhouse, dog park, playgrounds, parks, & spectacular sunsets. Two blocks from the waterfront trail, minutes from the 22-mile West Orange Trail, & near multiple parks. Historic downtown Winter Garden is a golf cart ride away, offering Crooked Can Brewery, rooftop dining, boutique shopping, splash park, Farmers Market, live theater, golf cart parades, 5Ks, book clubs, poker nights, and more. Convenient access to major interstates, premier golf courses, shopping, & Central Florida theme parks. Additional features: fresh interior/exterior paint (2021), Apple HomeKit-compatible door locks, thermostats & ceiling fans, Apple Secure Video cameras at the doorbell, front entry, pool area & indoor locations, new remote-controlled high-velocity fans on both porches, Apple HomeKit-controlled owner's bath fan, outlets inside primary bath cabinetry, 2, 85-inch Samsung Frame TVs that convey, & a state-of-the-art termite detection and control system with full warranty. Lovingly maintained & thoughtfully enhanced throughout, this one-of-a-kind Oakland Park pool & spa home is a special opportunity. Your oasis is waiting. Make it yours.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Matthew Mckee (407-948-0658)

Remarks: Under contract-accepting backup offers. Commanding striking curb appeal with its elegant stone exterior, this magnificent 2,952-square-foot Winter Garden estate offers the ultimate in turn-key luxury with four bedrooms, an office - flex space and three full bathrooms. Inside, soaring ceilings and elegant wood-look tile flooring guide you through a luminous, open-concept layout, while designer ceiling fans and plush carpeting elevate each of the four bedrooms. At the heart of the home, the upgraded epicurean kitchen shines with premium quartz countertops and stainless steel appliances, perfectly complemented by a thoughtful split-floor plan that ensures total privacy for the primary sanctuary. Unrivaled peace of mind is built directly into the property, boasting a brand-new roof (2025), a high-efficiency AC (2019), a tankless water heater (2019), and a dedicated interior laundry room. The interior transitions effortlessly to a spectacular outdoor oasis designed for world-class al fresco entertaining. The fully screened lanai showcases a striking custom ceiling and a premium outdoor kitchen, ideal for hosting unforgettable sunset soirées. Beyond the screen, a massive custom concrete patio extends into the beautifully manicured, privacy-fenced backyard, featuring a high-end retractable canopy for seamless indoor-outdoor living. Minutes from the fine dining and boutiques of historic downtown Winter Garden, this pristine residence perfectly balances refined style with unparalleled modern convenience. Cypress Reserve offers a community pool, playground and you are conveniently located near the new Tucker Ranch development, which will bring additional community amenities.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Jessica Otero, Pa (407-780-1663)

Remarks: Welcome home to this tastefully renovated 2/2 second floor condo located in the sweet spot of bustling Winter Garden Florida USA. Just about everything was updated in 2024 to include the kitchen with beautiful stainless appliances, granite countertops, cabinetry & lighting. Fresh paint throughout. New laminate flooring & baseboards in 2025, there is no carpet. The split bedroom layout is perfect for privacy while the primary bedroom is spacious with a walk in closet and ensuite bathroom. The 2nd bedroom includes a custom built closet and shelving providing ample storage options. The 2nd bathroom is adjacent to the 2nd bedroom. The washer and dryer hookups are located just off the kitchen providing easy access. This unit is conveniently located near the center of the community, just steps from the clubhouse, pool and mail areas. It also includes 2 designated parking spots just outside the unit. Windtree Gardens is situated in a fabulous area of Winter Garden providing quick access to all major roadways including the turnpike, 408 and 429. It is also just minutes from Historic Downtown Winter Garden including all that Plant Street has available, boutique shops, outdoor dining, Award Winning Farmer's Market, the very popular West Orange Trail and splashpad for the little ones. Bonus..there is a Starbucks near the entrance to the community. This unit is ideal for a starter home, a second home or an investment property. Schedule your showing soon as this one is sure to fly off the shelf.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Jeff Dodds (407-937-9521)

Remarks: Welcome to 17314 Bal Harbour Drive, a beautifully upgraded pool home in the sought-after Waterside community in Winter Garden, where luxury finishes, smart-home technology, and breathtaking water views come together in one exceptional property. From the moment you arrive, the home’s elegant curb appeal, fully fenced backyard, and impressive architectural details set the tone for what awaits inside. Step through the front entry into a bright and inviting foyer featuring ceramic tile plank flooring, tray ceilings throughout, and thoughtfully designed living spaces filled with upscale finishes. At the front of the home, Bedroom 2 offers a custom California walk-in closet, making it ideal for guests or multigenerational living. Nearby, Bathroom 2 features a stylish stand-alone shower, tile backsplash, and upgraded vanity. The flex room is perfect for a home office, media room, or playroom and showcases decorative shiplap accents, double-pane windows, custom-made glass double doors, and window treatments that complement the space. Continue into the heart of the home, where the gourmet kitchen is designed to impress with quartz countertops, stainless steel appliances, under-cabinet lighting, a convection oven, spacious pantry, pendant lighting with dimmers, and two coffee bars. The adjacent formal dining room is ideal for entertaining and includes designer lighting, shades, and curtains that convey with the home. The expansive great room is perfect for everyday living and gatherings, featuring built-in surround sound and beautiful views of the outdoor living area. Privately situated on the main floor, the primary suite offers tray ceilings, can lighting, a decorative light fixture, and elegant window treatments. The spa-inspired primary bathroom includes dual quartz vanities, a tiled walk-in shower with twin shower heads, a water closet, linen closet, and an oversized California walk-in closet. Upstairs, engineered hardwood stairs lead to a spacious loft area and Bedrooms 3, 4, and 5. Bedroom 3 features French closet doors, Bedroom 4 includes a walk-in closet and ceiling fan, and Bedroom 5 offers French doors, making it ideal as a bedroom, office, or hobby room. Bathroom 3 is appointed with dual sinks, granite countertops, and a tub/shower combination. Step outside to your private backyard retreat. The covered lanai overlooks a stunning saltwater pool with a 5-foot deep end, sundeck, and serene views of Avalon Lake. Entertain with ease using the outdoor kitchen featuring a gas grill, sink, and mini fridge while enjoying the Florida lifestyle. Additional upgrades include Ecobee smart thermostats, a Lutron lighting system with dimmers, Alexa voice-controlled lighting, motion-activated closet lights, reverse osmosis system, water softener, washer and dryer, and Simply Safe doorbell and security cameras. For added peace of mind, the home also features a brand-new AC system with a 10-year warranty. Residents of Waterside enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, dock, and pavilion. Don’t miss this opportunity to own a move-in-ready luxury home with premium upgrades, exceptional outdoor living, and stunning water views in one of Winter Garden’s most desirable communities.

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

Listing Agent: Regina Cruz (352-988-7488)

Remarks: Under contract-accepting backup offers. Welcome to 15336 Firelight Drive, located in the highly desirable gated community of Belle Meade in Winter Garden. Situated directly across from the lake, this beautifully maintained 4-bedroom, 3-bathroom home with a 3-car garage offers a spacious split-bedroom floor plan designed for both comfort and privacy. Inside, you'll find wood flooring, elegant architectural details, and a well-appointed kitchen featuring granite countertops, solid wood cabinetry, stainless steel appliances, a pantry, and a breakfast nook. The spacious primary suite includes dual walk-in closets, French doors leading to the screened lanai, and a spa-inspired bathroom with a garden tub, separate shower, and dual vanities. Major updates include a NEW ROOF installed in 2023 and a BRAND NEW HVAC system installed in June 2026, providing valuable peace of mind for the next owner. Conveniently located just minutes from Winter Garden Village, Highway 429, shopping, dining, and top-rated schools, this home offers the perfect combination of location, functionality, and lifestyle. Schedule your private showing today.

Listing is courtesy of: BRAZA HOMES (352-978-6993)

Listing Agent: Lucas Barbosa Santos (352-978-6993)

Remarks: Under contract-accepting backup offers. Experience the perfect blend of modern updates, resort-style amenities, and Disney-area convenience in this beautifully renovated townhouse located in the highly desirable Independence community. Thoughtfully updated throughout, the home features stylish new flooring, fresh interior paint, modern lighting fixtures, and a brand-new roof—providing a truly move-in-ready experience. The inviting living area enjoys peaceful, unobstructed views with no front-facing neighbors, creating the perfect backdrop to enjoy the Magic Kingdom’s dazzling nightly fireworks. Ample guest parking is conveniently located directly in front of the home, adding to the everyday convenience. Step outside to a spacious backyard and enjoy the covered walkway leading to the two-car garage—an ideal combination of comfort and functionality. Residents of Independence enjoy access to two resort-style clubhouses featuring pools, state-of-the-art fitness centers, tennis and basketball courts, and playgrounds, offering endless opportunities for recreation and relaxation. The HOA includes internet, cable, exterior maintenance, grounds maintenance, and pest control, making this property an excellent choice as a primary residence, vacation home, or investment opportunity.

Listing is courtesy of: RE/MAX TOWN CENTRE (407-996-3200)

Listing Agent: Fernando Barragan (407-325-1085)

Remarks: Under contract-accepting backup offers. The Gateway to Winter Garden Elegance. Welcome to a life of unparalleled charm and exclusivity in the heart of historic Downtown Winter Garden. Tucked away within Lake Cove Pointe—the downtown Winter Garden's sole gated enclave featuring dual access—this exquisite residence sits gracefully on a sprawling, fully fenced corner lot. Here, the coveted, golf-cart-friendly lifestyle of Central Florida's most sought-after destination isn't just an amenity; it is your new everyday reality. Step through the front doors and let the narrative of luxury unfold. You are immediately greeted by expansive vaulted ceilings that establish a grand, airy tone, while flawless, modern engineered wood floors guide you seamlessly through the home's sunlit living spaces. At the heart of the main level lies an open and spacious kitchen, intuitively designed for both quiet mornings and lavish entertaining. It is beautifully appointed with sweeping granite countertops, classic 42-inch white shaker cabinetry, and premium stainless steel appliances—all elegantly anchored by a vent hood and a modern flat cooktop. The dual pantries will serve you well. A guest retreat and full bath finishes out the main living area. Making your way to the stairs to discover a second level thoughtfully designed for both personal retreat and family connection. A versatile loft space offers the perfect canvas for a multi-media hub, creative lounge, or playroom. The crowning jewel of the home is the luxurious owner's retreat—a true sanctuary of elegance and comfort. It features an unparalleled, custom-scale walk-in closet that is simply second to none. Three additional, generously proportioned guest bedrooms and a conveniently located upstairs laundry room complete this refined upper level. The story of this home extends effortlessly outdoors to a spacious screened patio, offering a tranquil haven for evening relaxation or intimate weekend gatherings. Practical luxury is evident throughout the property, highlighted by the peace of mind of a pristine new roof installed in 2024, and an expansive three-car garage that effortlessly accommodates vehicles, your community golf cart, and all organizational needs. Beyond the gates, the quintessential Winter Garden experience awaits. Enjoy immediate access to the scenic West Orange Trail, take a leisurely stroll or bike ride to the vibrant boutiques and dining of Plant Street, and immerse yourself in the local culture at the famed Saturday Farmers Market. This is more than a magnificent home; it is your invitation to an enchanted lifestyle.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Matthew Mckee (407-948-0658)

Remarks: MOVE-IN READY | CONSERVATION LOT with SERENE LAKE BURNETT INLET VIEWS | GATED COMMUNITY | Welcome to this beautifully upgraded 4-bedroom, 2.5-bath home offering nearly 3,000 square feet of living space on a **PREMIUM CONSERVATION LOT** in the highly sought-after GATED COMMUNITY of HICKORY HAMMOCK. Perfectly positioned across from a PARK WITH SITTING BENCHES and sidewalk and next to a LUSH GREEN SPACE ON THE RIGHT side. Enjoy the tranquil scenery from the screened lanai of the Lake Burnett Inlet, framed by majestic oak trees draped in spanish moss. This property delivers PRIVACY, NATURE, AND EXCEPTIONAL CURB APPEAL Inside, you’ll find a bright **OPEN-CONCEPT LAYOUT featuring tile flooring throughout the first floor and luxury vinyl plank flooring on the second floor. This home boasts **CROWN MOLDING, **CUSTOM WINDOW CASINGS, **CUSTOM FEATURE WALL in the dining room and designer touches throughout. The spacious kitchen is the heart of the home with 42” cabinetry, stainless steel appliances, pantry, dry island, and a seamless flow into the great room and dining areas, perfect for entertaining and everyday living. A dedicated office/flex room on the first floor, offers the ideal work-from-home setup or bonus living space. Upstairs you will find additional living space in the oversized game room. The spacious primary suite features a cozy window bench seat, LARGE WALK-IN CLOSET, DUAL VANITIES, SOAKING TUB, WALK-IN SHOWER and private water closet. GENEROUSLY SIZED SECONDARY BEDROOMS, with two offering walk-in closets. Step outside to the screened lanai and enjoy peaceful water and conservation views from the FULLY FENCED BACKYARD with aluminum fencing, featuring dual side gates. Additional upgrades include **FRESH EXTERIOR PAINT, **NEW WATER HEATER** **NEW DISHWASHER** **NEWER WASHER AND DRYER** **GUTTERS WITH PREMIUM LEAF PROTECTION** **PRE-WIRING FOR A SECURITY SYSTEM. Residents of Hickory Hammock enjoy **RESORT-STYLE AMENITIES** including a Clubhouse, Resort Style Pool, Fitness Center, Tennis Courts, Sand Volleyball Courts, Fishing Pier, Playground, Walking Trails, Community Parks and Golf Cart Friendly Streets. Conveniently located near top-rated schools, shopping, dining, and major roadways. Only a short 10 minute drive to the Winter Garden Village or Downtown Winter Garden where you can enjoy a variety of restaurants, boutiques, Plant Street Market, coffee shops as well as the Farmer's Market on Saturday mornings. This is the Florida lifestyle Buyers have been waiting for. Schedule your private showing today.

Listing is courtesy of: CARIS REALTY AND INVESTMENTS INC (407-595-0009)

Listing Agent: Janelle Conway (407-595-0009)

Remarks: Virtually Staged. Welcome home to 921 Bending Oak Trail in highly sought-after, downtown, golf cart district of Winter Garden! This spacious 4-bedroom, 2.5-bath home is perfectly situated on a private oversized corner lot with serene pond views, offering both privacy and a peaceful backdrop. The thoughtfully designed layout features a first-floor primary suite and convenient downstairs laundry room. The main living areas showcase updated modern, stone-like tile flooring, while the kitchen offers a large walk-in pantry that extends under the staircase for exceptional storage. The spacious Living Room and covered patio are wired for a surround sound system and have beautiful water views from the windows and paver patio. Upstairs, you’ll find generously sized secondary bedrooms, including one with an oversized walk-in closet, along with a large loft ideal for a home office, playroom, or flex space, all featuring engineered hardwood flooring. Enjoy outdoor living with a spacious entertaining area and the added benefit of a rear-entry garage accessed through a private, owners-only alleyway where you can also enter the home without climbing any stairs. Major updates include a roof replacement in 2025, making this home as practical as it is beautiful. Lastly, the location is incredible, the neighborhood is extremely well maintained, offering a tranquil walking community around Brandy Lake and duck filled ponds, a sparkling community pool, entertaining pavilion, community greenspace, and perfect playground for the little ones.

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

Listing Agent: Claire Sims Llc (203-767-8109)

Remarks: Virtually Staged. SOLAR SYSTEM WILL BE PAID OFF BY THE SELLER AT CLOSING, $65,000 VALUE! Seller offering RATE BUY-DOWN so Buyer will enjoy lower monthly payments! Nestled on this beautifully remodeled and RECENTLY PAINTED home located on a premier OVERSIZED CORNER LOT within the guard-gated enclave of STONEYBROOK WEST, this stunning 5-bedroom, 3-bathroom residence offers the ultimate Winter Garden lifestyle. The home has been meticulously enhanced with MODERN UPDATES, ensuring a MOVE-IN-READY experience for today’s discerning buyer. SAVE ON UTILITY BILLS WITH THE WHOLE HOUSE SOLAR SYSTEM AND ELECTRIC CAR CHARGER. Inside, the open-concept layout is anchored by a SPACIOUS KITCHEN featuring quartz countertops, a central island, and HIGH-END STAINLESS STEEL APPLIANCES, all flowing into a spacious family room warmed by a classic fireplace. High-volume ceilings—reaching 9.25 feet on the main floor and an impressive 10.50 feet in the massive upstairs bonus room—create an airy, grand atmosphere throughout. The well-appointed laundry room includes a GE ULTRA WASHER AND DRYER, along with a STAINLESS STEEL UTILITY SINK for added convenience. The garage is equally impressive, featuring a heavy-duty Husky organizational system that provides exceptional storage and functionality. Retreat to the primary suite, where tray ceilings and a private walk-out balcony offer a peaceful vantage point overlooking the championship golf course. The lifestyle here extends far beyond the front door. Stoneybrook West is a premier “live-play” community boasting 24-hour staffed security and a spectacular waterfront clubhouse perched on the shores of Black Lake. For the outdoor enthusiast, the amenities are unmatched: enjoy private lake access via a community boat ramp and the rare convenience of an on-site boat storage lot. Whether you are hitting the links on the championship golf course, working out in the fitness center, or relaxing at the resort-style pool, every day feels like a vacation. Perfectly positioned for convenience, you are just 6 minutes from Winter Garden Village, 18 minutes from Walt Disney World, and only 30 minutes from Orlando International Airport. This home combines the security of a gated community, the luxury of recent high-end improvements, and the rare perk of Florida lake living. Call today to schedule your private showing!

Listing is courtesy of: EXP REALTY LLC (407-706-5000)

Listing Agent: Daniel Betancourt (407-375-9142)

Remarks: Welcome to this beautifully designed 2022-built home freshly painted, move in ready and located in the highly sought-after Waterside at Johns Lake community in Winter Garden! Offering 4 bedrooms, 3 full bathrooms, and over 2,030 square feet of thoughtfully designed living space, this move-in ready home combines modern style, functionality, and an unbeatable location. Step inside to an open-concept floorplan featuring a spacious great room, abundant natural light, ceramic tile flooring in the main living areas, and seamless flow between the kitchen, dining, and living spaces — ideal for entertaining and everyday living. The kitchen features solid surface countertops, modern appliances, ample cabinetry, and overlooks the main gathering areas for easy living and hosting. The flexible layout includes a desirable first-floor bedroom and full bath perfect for guests, multigenerational living, or a private home office. Upstairs, the spacious primary suite offers a walk-in closet and relaxing retreat feel, while additional bedrooms provide generous space and versatility. Additional features include central air, public utilities, inside laundry, ceiling fans, walk-in closets, split-bedroom design, and modern finishes throughout. Located in Waterside on Johns Lake, residents enjoy resort-style community amenities including a community pool, playground, walking trails, green spaces, and scenic surroundings. Conveniently located near Downtown Winter Garden, Horizon West, Hamlin, Winter Garden Village, SR-429, Florida Turnpike, Disney, shopping, dining, hospitals, golf, and top-rated schools. Enjoy easy access to everything Central Florida has to offer while living in one of Winter Garden’s fastest-growing and most desirable communities.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Cassie Lamoureux (407-432-9180)

Remarks: Located in the GATED community of Wintermere Pointe in Winter Garden, FL, this spacious .25 acre, 5-bedroom, 3-bath pool home for sale in Winter Garden offers nearly 3,750 square feet of well-designed living space just minutes from Winter Garden Village, Windermere, Walt Disney World, AdventHealth Winter Garden, SR 429, and the Florida Turnpike. Designed for both everyday living and entertaining, the home features an open-concept layout with formal living and dining rooms, a large family room, and a centrally located kitchen that flows seamlessly into the main living areas. A DOWNSTAIRS BEDROOM and full bath provide flexibility for guests, multi-generational living, or a private home office, while upstairs, the expansive primary suite offers a true retreat with a soaking tub , separate shower, dual vanities, and two walk-in closets. Additional bedrooms are generously sized, and both a LOFT and a large BONUS ROOM create endless possibilities for a media room, game room, home gym, or additional living space. High ceilings and natural light enhance the open feel throughout the home, while the layout offers both functionality and comfort. Step outside to a screened-in PRIVATE POOL, covered lanai and extended paver patio, perfect for enjoying Florida living in Winter Garden year-round, all set on a .25 ACRE LOT with mature landscaping and a FULLY FENCED backyard for added privacy. Wintermere Pointe is a well-established gated community in Winter Garden, Florida offering tennis courts, a playground, and a LOW HOA, and is zoned for Lake Whitney Elementary, SunRidge Middle, and West Orange High. If you’re searching for homes for sale in Winter Garden FL with a pool, gated community, and flexible layout, this home offers space, location, and lifestyle in one of Central Florida’s most desirable areas.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Alexis Bress (407-900-0771)

Remarks: PARADE of HOMES-OAKLAND PARK! Experience refined Florida living in the heart of Winter Garden, where timeless architecture, thoughtful design, & an unbeatable location come together in this exceptional custom-built residence. Situated on an expansive corner lot (~1/4 acre) overlooking one of the community’s most beloved PARKS, this four-bedroom (w/ room for a 5th & office), four-bath luxury HEATED POOL home offers privacy, space, & picturesque views. You’re moments from stunning sunsets, a walk by the LAKE, multiple parks & playgrounds, the community clubhouse, & direct access to the scenic WEST ORANGE TRAIL— a 22-mile paved trail ideal for biking, jogging, & casual strolls. From the moment you arrive, the stunning brick-accented front porch sets the tone, offering a welcoming space to relax while enjoying tranquil park views. Inside, rich wood flooring flows throughout the main living areas, complementing the home’s elevated finishes, such as crown molding, wainscoting, trim work, & custom built-ins. The chef’s kitchen is a true showpiece. Outfitted with premium Thermador & JennAir appliances, QUARTZITE counters, custom cabinetry, designer fixtures, a walk-in pantry, & spacious gathering space, this kitchen was designed for both everyday living & elegant entertaining. The adjacent dining & living areas are bathed in natural light, enhanced by multiple French doors that frame panoramic views of the pool and backyard retreat. The indoor-outdoor connection is simply spectacular. Step outside to your private oasis featuring a sparkling resort-style pool (runs with an ozonator) with travertine decking, generous covered lanai, & an outdoor kitchen equipped with a mini fridge & 48 inch griddle. Each of the four bedrooms is generously sized, offering comfort & versatility for family & guests. One generously sized bedroom is downstairs, which has access to the pool & park through French doors. The primary suite serves as a luxurious retreat with a spa-like bath & dual closets, while all four baths (three en-suite) are thoughtfully designed with quality finishes (marble upstairs, quartzite downstairs). Need an elevator? There's space for the addition! A well-appointed MUDROOM adds everyday convenience & organization, seamlessly blending practicality with style. Additional FEATURES: whole house water filtration system, in-ceiling speakers in the living room, the lanai by the pool, & front porch, tankless water heaters, hard wired cameras inside/out, ample storage, landscape lighting, Cat 6 wiring w/ WiFi access points, & an OVERSIZED garage (~2 1/2). Just a short GOLF CART ride away, you’ll find the charm & 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, community 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. 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. Custom built POOL homes are RARE to market in Oakland Park. Make this DREAM home your reality today!

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

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