Homes for Sale Near West Orange High in Winter Garden - 161 homes

Remarks: 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: Experience elevated living perfectly situated on a private conservation homesite with no rear neighbors in the gated community of Lake Roberts Landing in Winter Garden. This fully renovated luxury pool home offers an exceptional blend of privacy, elegance, and convenience in the heart of Winter Garden. Spanning over 4,200 square feet, this move-in-ready home features 6 bedrooms, 4 bathrooms, a 3-car tandem garage, dedicated theater room, expansive upstairs loft and a resort-style backyard with an outdoor kitchen designed for year-round Florida living. Every major finish has been thoughtfully updated, including new flooring throughout, fresh interior and exterior paint, a completely renovated chef’s kitchen with upgraded countertops, appliances, lighting, and beautifully updated bathrooms that create a modern yet timeless aesthetic. The versatile floor plan includes two bedrooms and a full bathroom on the main level, providing the perfect setup for guests, multigenerational living, a home office, gym, or flex space, while also serving as a convenient pool bath. Heading upstairs, you’ll immediately notice the updated wrought iron spindles, luxury vinyl plank flooring, and abundant natural light that fills the space. The expansive loft serves as the ultimate entertainment hub, complete with a spacious sitting area, custom bar, bar refrigerator, mounted TV, and designer lighting, creating the perfect space for hosting family and friends or enjoying the big game. A dedicated theater room provides the ideal setting for movie nights and elevated at-home entertainment. The luxurious primary suite serves as a private retreat featuring a fully renovated spa-inspired bathroom with dual vanities, makeup vanity, freestanding soaking tub, oversized walk-in shower with multiple shower heads and rain shower, stunning designer tile work, and an oversized walk-in closet. Three additional bedrooms, two fully updated bathrooms, and an oversized laundry room complete the second floor. Designed for both relaxation and entertaining, the backyard is a true showpiece featuring a newer pool with newer pool equipment a gas-heated pool and spa, outdoor kitchen with built-in grill, beverage refrigerator, TV, bar seating, ambient lighting, covered lanai, expansive paver patio, fully fenced, with redesigned landscaping and tranquil conservation views that provide a level of privacy rarely found in Central Florida. Significant recent improvements include a new tile roof installed in 2024, a new HVAC Unit (2025), two new water heaters and newer pool & equipment offering both peace of mind and long-term value. Lake Roberts Landing features a community pier/dock onto Lake Roberts to enjoy the beautiful lake and fishing. Perfectly located just minutes from Winter Garden Village, Downtown Winter Garden, Windermere, Hamlin, A-rated schools (Lake Whitney Elementary, SunRidge Middle and West Orange High), premier shopping, dining, entertainment, SR-429, and Florida’s Turnpike, this exceptional residence offers the luxury lifestyle today’s buyers are searching for in one of Winter Garden’s most sought-after gated communities. A rare opportunity to own a fully updated luxury home with a private conservation lot, no rear neighbors, resort-style outdoor living, and an unbeatable Winter Garden location.

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

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

Remarks: BUY THIS HOME WITH 100% FINANCING! LOCATION, LOCATION, LOCATION! Welcome to Your Trailside Oasis in Historic Oakland/Winter Garden! Nestled directly along the scenic West Orange Trail, this meticulously maintained, lightly lived-in bungalow offers the ultimate Florida lifestyle. Cycle straight into vibrant, historic downtown Winter Garden, or retreat to your own peaceful haven under the towering Live Oaks of Oakland Trails. Sophisticated Design Meets Modern Comfort...From the moment you arrive, the extended paver driveway and charming, shaded front porch welcome you home. Step inside to an airy, open-concept living area adorned with gleaming ceramic tile floors, quartz countertops, and upgraded builder finishes. Thoughtful, highly functional details elevate the main floor, including a stylish drop zone by the two-car garage, an under-stair coat closet, and a convenient powder room. High-end custom shades, luxury ceiling fans, and designer light fixtures make this residence completely turn-key and move-in ready. The second level opens into a versatile loft perfect for a media room, home office, or play space. The primary suite serves as a true sanctuary, boasting a grand double-door entrance, two spacious walk-in closets, and an ensuite bath with elegant quarts countertops. Two additional bright bedrooms and a dedicated upstairs laundry room complete this flawlessly designed upper level. Equipped with modern exterior lighting and a security camera system, this home offers total peace of mind. Outside your door, the vibrant Oakland Trails community features a resort-style pool, playground, dog park, and endless walking trails. Abundant dedicated street parking makes hosting family and friends effortless. Positioned perfectly between Clermont and Orlando, you will enjoy rapid access to the Florida Turnpike, 429, 408, and Highway 50. With Killarney Station right outside the neighborhood and the breathtaking Oakland Nature Preserve on the shores of Lake Apopka less than five minutes away, this is a dream destination for outdoor enthusiasts. Don't miss the chance to own this pristine, upgraded gem in one of Central Florida's most desirable trailside communities! Offering a lender credit towards costs or interest rate buy-down, when the client uses the preferred lender ACE Lending Group, ASK HOW.

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

Listing Agent: Ariel Vargas (407-558-5161)

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: Experience the quintessential Winter Garden lifestyle in this exceptional 3 bedroom/2.5 bathroom home, perfectly positioned within the highly sought-after Golf Cart District. This residence offers a rare park-side setting, providing picturesque views of majestic oaks with green space. For those who enjoy active community life, you are just steps away from the neighborhood pool and playground. Just a few minutes away from Downtown Winter Garden!  Exceptional Curb Appeal & Interior Elegance: from the moment you arrive, the covered front porch welcomes you with outdoor column lights, coach lights, landscaping and a framed transom over the front door. The first-floor features stylish Bahama shutters, formal living room with a double paddle ceiling fan, spacious dining area, a family room that features a gas fireplace, with tile flooring, engineered wood floors and LVP throughout the first floor. Chef-Inspired Kitchen : The heart of the home is the kitchen, which has been upgraded from an electric to a gas stove and features a redesigned pantry to maximize storage. You will also find under-cabinet lighting and modern lighting. Primary suite: The 1st floor Primary Bedroom suite serves as a private sanctuary with new flooring throughout the bedroom, closet, and bathroom, as well as a completely remodeled primary bathroom.   The second story split floor plan: The transition to the second floor is highlighted by a staircase and balcony where traditional wood newels have been replaced with elegant rod iron. The second story features 2 spacious bedrooms , a full sized guest bathroom and at center stage of the upstairs landing is a bonus area for additional lounging area/home office or play area. Outdoor Oasis: Step outside to your private retreat: a rear enclosed screened-in room that perfectly encompasses the lanai and soaker pool area. The outdoor space is further enhanced by: An extended patio deck around the pool, a new fan on the lanai for year-round comfort, a rebuilt pool pump with pool equipment housing, a new fence with a leveled concrete retaining wall base, accented by fence and landscape lighting.  Systems & StorageSolutions: This home offers incredible peace of mind with a new roof (installed 11/2020) and a brand-new AC system (3 weeks old) with a transferable warranty. Storage is a priority here, with a garage featuring built-in file cabinets, recessed ceiling lights, shelves, appliance storage, and overhead shelving, plus additional attic storage. Functional extras include a built-in wall safe, a generator pad, and a security camera at the rear of the home.  Schedule your private showing today!

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

Listing Agent: Lorie Gullian (407-928-8078)

Remarks: Welcome to 14252 Creekbed Circle, a spacious and beautifully designed home located in the heart of Winter Garden, in Bradford Creek, one of Central Florida's most sought-after communities. Perfectly situated near Downtown Winter Garden, you'll enjoy convenient access to popular restaurants, boutique shopping, farmers markets, community events, walking trails, and entertainment year-round. This expansive 4-bedroom, 3.5-bath residence offers plenty of room for everyone with a versatile floor plan designed for modern living. The oversized bonus room provides endless possibilities and can be used as a home office, game room, media room, playroom, fitness area, or additional living space to fit your needs. The spacious layout features generous living and dining areas, creating the perfect setting for entertaining guests or enjoying everyday life. The large kitchen with a center island for entertaining and an abundance of cabinets for all of your cooking needs. The private owner's suite offers a relaxing retreat, while the additional bedrooms provide comfort and flexibility for family and visitors. With abundant living space, a desirable location, and easy access to everything Winter Garden has to offer, this home combines convenience, functionality, and lifestyle in one exceptional package. Near Winter Garden Village, Disney and Advent Health in Winter Garden with easy access to 429/408 and the Turnpike. Don't miss the opportunity to make this your next home. Garage equipped with Tesla Charger, Upstairs HVAC replaced 8/2025, Downstairs HVAC replaced 1/2026, Dishwasher replaced 12/2024, Luxury Vinyl Plank flooring installed 12/2025 and new interior paint 5/2026.

Listing is courtesy of: WATSON REALTY CORP (407-323-3200)

Listing Agent: Carla Robles (407-462-2347)

Remarks: ***Seller to offer up to $19,000 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: 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: 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)

Remarks: Expansive and Inviting! Welcome home to 14790 Tullamore Loop. Location says it all! Convenient to restaurants, shopping, highways, theme parks, and more, this gated community remains one of the most popular communities in the area. This family-oriented neighborhood with a community pool is sure to please. With an oversized lot and plenty of room to roam, the open floor plan of this 4-bedroom / 2.5-bath home awaits to impress. Large formal living and formal dining rooms are the perfect venue for family gatherings. An elegant, open kitchen, overlooking the dinette into the family room, offers granite counters, 42” cabinets, double built-in ovens, a large breakfast bar, and a huge walk-in pantry allowing space for everyone to help the cook. When the day is done, retire to the oversized second-floor primary suite, which offers a spacious bath with a double-sink vanity, shower, garden tub, and a walk-in closet, completing this special and intimate space. Anchoring 3 large secondary bedrooms, this home beckons to an active family, offering the space you need. Enjoy your morning coffee or an evening barbecue, while enjoying the peace of your private pool, a HUGE private backyard! Complete with fruit trees (recovering from the freeze), including mango, sugar apple, sapodilla, guava, loquat, pear, jackfruit, fig, lemon, orange, neem, and banana, gives an instant farm-to-table experience. While certainly offering plenty of space for everyone to claim their own piece of paradise, you’ll find peace of mind that your investment is in a location that can’t be beat! Highlights include: Roof replaced in 2020. AC replaced in 2018. Appliances replaced in 2022. All blinds replaced 2022. Whole Home water filtration and softener system. Be sure to click the link for an interactive 3D Virtual Tour and floor plan!

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Rita Phillips (407-928-0573)

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: Experience luxury living in one of Winter Garden’s most desirable areas. This beautifully upgraded single-family home offers 4 spacious bedrooms and 2.5 elegant bathrooms, blending modern comfort with timeless sophistication. From the moment you step inside, you are welcomed by an open-concept design filled with natural light, enhanced by high-quality porcelain tile flooring throughout, adding elegance, durability, and a sleek modern finish to the entire home. The gourmet-style kitchen, fully renovated in June 2024, showcases contemporary finishes, modern design, and exceptional functionality for even the most discerning buyer. The outdoor space features a spacious covered patio, perfect for extending your living area, ideal for entertaining, enjoying Florida’s year-round weather, or relaxing in privacy. A 2-car garage adds convenience and everyday practicality. Recent upgrades provide lasting value and peace of mind, including a newer roof (2021) and an energy-efficient A/C system (2017), ensuring comfort and reliability for years to come. Located in a highly sought-after Winter Garden community, this home places you just minutes from upscale dining, boutique shopping, parks, and the vibrant lifestyle that makes this area so desirable. A rare opportunity to own a move-in-ready home that perfectly combines luxury, style, and location. Schedule your private showing today and experience elevated living at its finest.

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

Listing Agent: Esperanza Valencia (407-242-3799)

Remarks: Positioned on a premium homesite with an expansive manicured common area along one side, this property offers added privacy and open space, along with sweeping views of John’s Lake from the front of the home. Inside, the home opens to a formal dining area accented by wood beam ceilings, while custom wall details in the foyer and along the staircase add a refined, designer touch. The main living area features soaring ceilings, abundant natural light, wood beam ceiling accents, and a striking floor-to-ceiling accent wall, creating a dramatic yet inviting focal point that flows seamlessly into the dinette and open kitchen. Designed for both everyday living and entertaining, the kitchen includes a large island with seating, sleek cabinetry, stainless steel appliances, a gas cooktop, built-in oven, and generous pantry space. Just off the pantry, a connecting space between the kitchen and dining room offers the perfect opportunity for a coffee station or butler’s pantry. The main level also offers a spacious primary suite with a well-appointed bath and a custom walk-in closet featuring built-in drawers, cabinetry, and shelving, along with a secondary bedroom and full bath, ideal for guests or multigenerational living. Upstairs, you will find three additional bedrooms, including one with a private bath, while the remaining two share a full bath, plus a generous loft overlooking the living area that provides flexible space for a secondary living area, home office, or play space. The outdoor living space is designed for true Florida living, featuring a saltwater pool and spa added in 2021 with full automation, expansive Travertine tile decking, and a lanai with a motorized screen that extends your living space year-round. The patio is also pre-plumbed for a future outdoor kitchen, offering even more potential for entertaining. Additional highlights include a split three car garage configuration with a separate side entry one car bay and a 2 car garage equipped with an EV charging outlet. Waterside on John’s Landing offers a clubhouse, fitness center, resort-style pool, playground, covered dock, and pavilion on John’s Lake, all conveniently located near Horizon West, Hamlin, shopping, dining, and major roadways.

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

Listing Agent: Alex Vastardis (407-947-6264)

Remarks: You found it with this Location! The family will love this beautiful, Former Model home in Traditions! Blocks away from Downtown Winter Garden! Golf carts welcome! This 3/2 split plan has wood laminate flooring in living room & the master bedroom. Kitchen is open, Ceramic tile & eat-in space overlooking backyard. Master Bedroom is spacious with Walk-in shower and separate tub. Private / separate laundry room. Separate office or workshop in garage is UNDER AIR UNDER & perfect for the handyman! The backyard is fully fenced. Enjoy the restaurants, famer's market & shops all in walking distance or use a golf cart! Separate Workshop room. AC 2019. Easy access to the turnpike, 429, 408 to downtown Orlando or OIA! Great Schools! Solar panels will be paid off at closing!

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

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

Remarks: Experience elevated living in this exceptional custom home by J&J Building, perfectly positioned in one of Winter Garden’s most desirable locations directly across from the iconic West Orange Trail. Offering over 5,000 square feet of thoughtfully designed luxury, 811 Civitas Way blends sophisticated style, flexible living spaces, and impressive functionality rarely found in today’s market. Designed for both everyday comfort and unforgettable entertaining, the home features a truly jaw-dropping media room that delivers the ultimate cinematic experience. Multiple office and flex space options provide incredible versatility for remote work, creative pursuits, fitness, or multigenerational living. With bedrooms thoughtfully positioned on both the first and second floors, the layout offers ideal privacy and convenience for guests and family alike. Luxury details and custom upgrades are showcased throughout, including a whole-home generator, a one-year-old Sub-Zero refrigerator, two stunning crystal chandeliers installed last year, and elegant solid brass door hardware throughout the home. You'll fall in love with the large island in the garage that even includes a built-in gift wrapping station! Every space reflects exceptional craftsmanship and thoughtful design, with countless additional custom touches that elevate the home’s overall sophistication and character. One of the property’s standout features is its exceptionally rare amount of parking for 7 cars plus a golf cart— a coveted luxury that sets this home apart. Combined with its prime location near Downtown Winter Garden, scenic trail access, dining, shopping, and commuter routes, this residence offers a lifestyle that is as refined as it is practical. **There is room to add a pool and ADU on this lot, as well! Artist renderings with the pool included in the photos.

Listing is courtesy of: OAK AVENUE REAL ESTATE LLC (407-720-5000)

Listing Agent: Tracey Mcfadden (321-217-7808)

Remarks: Under contract-accepting backup offers. Freshly painted 1-bedroom, 1 bath. Ready to move-in. Laminate floors in the dining area, living room, and bedroom. Kitchen and Bath have ceramic tiles. Southern Pines has many amenities, like in door basketball court, a Racketball court, tennis, Volleyball, a car wash, a dog park, playground. Fully equipped Gym and theatre, Pool table in the clubhouse, BBQ Grills and a kitchen area with only a small refrigerator and sink, Great counter space with tables and chairs for small partiescual. Owner financing available, call for details. NEW PRICE!!!!

Listing is courtesy of: HOMESMART (407-476-0451)

Listing Agent: Maria Lloret (407-929-1994)

Remarks: Nestled within the intimate Garden West enclave — just 11 exclusive homesites — this 4-bedroom, 3-bathroom J&J Building masterpiece spans 2,698 square feet of meticulously curated living space and sits directly on the West Orange Trail. Lace up your sneakers and you're seconds from one of Florida's premier multi-use trails, stretching 22 scenic miles through the heart of West Orange County. Located in the heart of Winter Garden's beloved Golf Cart District, Downtown Winter Garden's vibrant Plant Street is just a half mile away — putting award-winning restaurants, the beloved Saturday farmers market, boutique shops, and year-round community events right at your doorstep. From the moment you arrive, the Florida-inspired architecture, lush professionally re-landscaped grounds with low-voltage landscape lighting, and inviting covered front porch signal that every detail has been considered. Inside, the owners have transformed this already exceptional home into something truly turnkey. Two stunning shiplap feature walls anchor the main living spaces, while all-new designer lighting fixtures — inside and out — have been upgraded throughout and are fully programmable via the Leviton app, so you can set the perfect ambiance from anywhere. The chef's kitchen remains the heart of the home, featuring a Dacor 36" gas range, Samsung Pro dark stainless appliances, quartz countertops, subway tile backsplash, and ceiling-height cabinets beneath a one-of-a-kind shiplap vented hood. A reverse osmosis water filtration system at the kitchen sink adds a thoughtful, health-forward touch. Natural oak hardwood floors, crown molding, and custom woven wood window treatments on the first floor carry sophistication from room to room, while cordless blinds keep the second floor clean and effortless. The main floor offers an open living area with a guest bedroom and full bath — ideal for visitors or multigenerational living. The living room features a mounted, tilt-and-extend TV (included) paired with a Sonos sound system, controlled seamlessly by app for both the living room and lanai. Upstairs, the primary suite, two additional bedrooms, and a versatile loft provide space to spread out. Step outside and the screened lanai — enclosed with premium no-see-um screen material — becomes a true outdoor living room. Backyard café string lights, a mounted TV (included), Sonos audio, a natural gas BBQ stub-out, a retractable privacy blind, and no rear neighbors make this the ultimate Florida entertaining space. Additional outdoor power outlets and thoughtfully designed landscape lighting round out the backyard experience. Built for efficiency and peace of mind, the home features spray foam insulated block walls, energy-efficient double-pane windows, a radiant roof barrier, and a tankless gas water heater. Programable keyless entry locks secure all exterior doors, including the garage. The detached two-car garage — complete with a dedicated golf cart bay and overhead SafeRack storage — connects to the main house via a covered breezeway, a nod to the community's lifestyle-first design. This is more than a home. It's a lifestyle — trail, town, golf cart community, and turnkey luxury all in one.

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

Listing Agent: Alexis Anderson (561-670-5901)

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: PRICE IMPROVEMENT! Refined Waterfront Living in Winter Garden’s Coveted Golf Cart District! Set within one of Downtown Winter Garden’s most desirable gated enclaves, this exceptional waterfront residence offers a rare blend of sophistication, privacy, and effortless Florida living—perfectly positioned in the highly sought-after golf cart district. Designed to maximize light and livability, the interiors are bright and inviting. Recent enhancements include new exterior paint (2026), a tankless water heater (2026), and a added ensuite bathroom (2026) making two primary suites on the second floor. Generous storage is thoughtfully integrated with expansive closet space, while a whole-home water softener and purification system, including an under-sink filter, ensures elevated everyday comfort. At the heart of the home, the gourmet kitchen is both functional and beautifully appointed, featuring dual sinks, a dedicated prep island, and upgraded soft-close cabinetry. The oversized three-car garage provides ample room for vehicles, storage, or recreational needs. Outdoors, the lifestyle truly unfolds. A recently resurfaced covered boat dock—complete with lift, lighting, fan, and sink—offers direct access to one of Florida’s largest spring-fed lakes, part of the Harris Chain and extending to the St. Johns River and Atlantic Ocean. The expansive grounds are enriched by mature, fruit-bearing trees including mango, avocado, star fruit, and citrus, creating a lush, private retreat. Surrounded by natural beauty, the property attracts an impressive array of wildlife. Unforgettable sunrises and sunsets can be enjoyed from multiple vantage points, including the living spaces, patio, dock, and three north-facing bedrooms with water views. This is a home that seamlessly balances elegance and ease—offering a rare opportunity to experience serene waterfront living in one of Winter Garden’s most iconic settings.

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

Listing Agent: Alexis Anderson (561-670-5901)