Homes for Sale Near West Orange High in Winter Garden - 174 homes

Remarks: Under contract-accepting backup offers. 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: You will find comfort, convenience and flexibility with this lovely well maintained 3 bedroom 2 1/2 bath townhome located in Stoneybrook West. With Ceramic tile in the kitchen and bathrooms, the owner replaced all carpet with laminate wood flooring. The en suite primary bathroom was beautifully updated in 2025 with attention to upgrades like a double vanity quartz countertop and soft closed drawers. The Primary suite has two walk in closets and new energy efficient windows. The second bedroom boasts a walk in closet as well. From the cozy screened back patio, it’s a quick walk to the community playground and pool. This quiet family friendly community is within walking distance of all your shopping needs and also just a short drive to Winter Garden Village and charming Historic Downtown Winter Garden. There you’ll find the West Orange Trail for biking, running or a simple stroll after dining at some of the area’s finest restaurants. Adding to your peace of mind, the roof was replaced in 2023 along with repainting of the exterior of the properties in the community. The HVAC was replaced in April 2021. The exterior was upgraded to a 3 ton in August 2019 and maintained annually. Schedule your showing and make this turnkey townhouse your home.

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

Listing Agent: Jodene Chase (407-616-5634)

Remarks: Price Reduction! Owner says SELL!! 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. The owner has spent in excess of $60,000 on these renovations. 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. Also just a short drive to Winter Garden Village at Fowler Grove with numerous dining and retail options. 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: SHOW STOPPER! Welcome to 15587 Hamlin Blossom - in the highly sought-after gated community of HICKORY HAMMOCK. A rare find, this Ashford model by M/I Homes is one of only six Ashford floor plans built in the community. Every detail of the 1860 sq. ft has been thoughtfully designed and meticulously cared-for, creating a TURNKEY experience unlike any other. Start off on your paver driveway and enjoy the handpicked lush new landscaping and welcoming porch-sitting area where you can immediately enjoy the outdoor Florida lifestyle. NEW EXTERIOR PAINT. Once inside you are greeted with perfection. NEW luxury vinyl flooring in each bedroom. NO CARPETS throughout the entire SINGLE STORY home. A foyer that immediately impresses with crafted lighting fixtures and perfectly placed decor. SPLIT FLOOR PLAN creates privacy for the two bedrooms and bath in the front of the home. Double vanity with UPGRADED lighting and hardware to elevate the bathroom space. The OPEN FLOORPLAN and dining room/living room combo is perfect for entertaining guests. Create the ideal ambiance with your ALEXA-enabled recessed lighting. A chef’s dream kitchen with BRAND NEW refrigerator, NEW dishwasher, and NEW garbage disposal. The primary suite is perfectly appointed with classic upgrades and reading nook. The HIGHLIGHT of the home is the wraparound paver patio with outdoor living/dining room space and OUTDOOR KITCHEN all under a screen enclosure overlooking a fully fenced, newly landscaped outdoor and garden area. Other upgrades include NEW washer/dryer, NEW HVAC components, NEW TESLA charging station. Hickory Hammock is a special enclave of Winter Garden that overlooks John’s Lake. Residents enjoy water views, private fishing pier, tennis courts, beach volleyball courts, nature trails, resort-sized swimming pool, fitness center, clubhouse, and nature trails. Located in the heart of Winter Garden and Horizon West, this home is approximately 5 minutes from SR 429, 10 minutes from Hamlin Town Center, 10 minutes from Downtown Winter Garden, and approximately 25 minutes from Walt Disney World. Residents enjoy convenient access to shopping, dining, entertainment, top-rated schools, major employment centers, and everything that makes Winter Garden one of Central Florida's most desirable places to live. Contact list agent for full list of upgrades AND seller’s complete maintenance schedule/records. Homes this well cared for do not come on the market often. See it for yourself today!

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Michelle Zimmerman (732-616-6019)

Remarks: Located within Winter Garden’s golf cart district and just minutes from Plant Street, this property offers a distinctive combination of current residential use, C-2 General Commercial zoning, and no HOA. The single-story, concrete-block home includes 2 bedrooms, 1 bathroom, 1,034 square feet of heated living space, an enclosed porch that provides additional flexible space, and a roof replaced in 2023. The interior is ready for renovation, allowing the next owner to update the property according to their intended use and vision. Situated on an approximately 0.19-acre homesite, the property also features mature shade trees, a concrete driveway, and fenced sections of the yard. Its central Winter Garden location provides convenient access to the restaurants, shops, farmers market, community events, and West Orange Trail surrounding downtown and Plant Street, while nearby golf-cart-friendly roadways offer another way to explore the area. Whether considered for continued residential use, a renovation project, or a future business opportunity, this property presents a range of possibilities in a well-connected location. Buyers should independently verify all intended uses, permitting requirements, and zoning regulations with the City of Winter Garden.

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

Listing Agent: Christopher Bessette (407-292-5400)

Remarks: Tucked inside a sought-after gated community, this beautifully designed 4-bedroom, 4-bath home offers the perfect blend of comfort, elegance, and everyday livability. From the moment you arrive, you’ll appreciate the sense of privacy, space, and thoughtful design that make this home truly special. With formal living and dining rooms, a private office/study, and a spacious bonus room with a full bath, there is room for everyone to live, work, gather, and unwind. At the heart of the home, the centrally located kitchen brings everything together, opening naturally to the main living areas and creating an ideal setting for both entertaining and daily life. Appointed with granite countertops, a center island, double ovens, and a pantry, it is as functional as it is inviting. Beautiful crown molding, decorative wall details, and tile flooring throughout the main living spaces add warmth and character, while the bedroom spaces offer comfort and privacy. The primary suite is a peaceful retreat, privately positioned and complete with two walk-in closets, dual vanities, a soaking tub, and a separate shower. Secondary bedrooms are thoughtfully arranged, including a Jack-and-Jill bath, while the bonus room provides flexible space for guests, a media room, a playroom, or multi-generational living. Step outside and enjoy your own private Florida oasis. The screened saltwater pool, convenient pool bath, and expansive paver deck with both covered and open-air areas create the perfect backdrop for quiet mornings, weekend gatherings, and year-round outdoor living. Backing to a green area, the setting feels peaceful and private, offering a rare sense of escape while still being close to everything. Located near Winter Garden Village, Highway 429, top-rated schools, shopping, and dining, this exceptional home offers not just a place to live, but a lifestyle to love. Make sure to check out the 3D tour and Virtual tours.

Listing is courtesy of: MARTI PURDY PROPERTIES INC (407-614-6177)

Listing Agent: Marti Purdy (407-761-0848)

Remarks: Looking for a move-in ready home in Winter Garden with modern upgrades, an ideal location, and a true sense of community? Welcome to this beautifully maintained 3-bedroom, 3-bathroom home in the highly desirable Oakland Park neighborhood. Designed for today's lifestyle, this home features a bright open-concept floor plan, abundant natural light, spacious living areas, and a functional layout that's perfect for both everyday living and entertaining. Premium upgrades include gas appliances, elegant plantation shutters, and stylish finishes throughout, offering a turnkey, low-maintenance home you can enjoy from day one. Located in one of Winter Garden's most sought-after golf cart communities, Oakland Park offers resort-style amenities, scenic trails, parks, green spaces, and top-rated schools, creating the perfect setting for an active, connected lifestyle. Just minutes from Historic Downtown Winter Garden, you'll have easy access to the nationally recognized farmers market, local restaurants, boutique shopping, coffee shops, seasonal festivals, live entertainment, and the West Orange Trail. Whether you're searching for a close knit neighborhood, a home near downtown Winter Garden, or a community with exceptional amenities, this property checks every box. Don't miss this opportunity to own a beautifully upgraded home in one of Central Florida's most desirable communities.

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

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

Remarks: Under contract-accepting backup offers. ***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: ~Seller may consider buyer concessions if made in an offer~Prepare to fall in love with this BEAUTIFULLY MAINTAINED 4-bedroom, 3.5 bath home in the highly sought-after Waterside at Johns Lake community, where timeless style, THOUGHTFUL UPGRADES, and an unbeatable location come together to create an exceptional place to call home. Offering over 2,900 SQUARE FEET, this 2019-built residence still FEELS LIKE NEW and sits proudly on a beautifully landscaped CORNER LOT within one of the area's most desirable neighborhoods featuring TOP-RATED SCHOOLS. From the moment you arrive, you'll be impressed by the home's outstanding CURB APPEAL highlighted by lush landscaping, FRESH EXTERIOR PAINT (2026), and an inviting brick paver walkway leading to the charming front porch. Step inside to discover an open floor plan where elegant CERAMIC TILE FLOORING, fresh interior paint (2021), and crown molding (2021) create a refined backdrop for everyday living. A VERSATILE first-floor Bedroom with its own EN SUITE BATH, make it an ideal guest suite, private office, or multi-generational living space. The spacious Living Room creates a stunning impression with its custom STACKED STONE ACCENT WALL with sleek electric fireplace, creating a warm yet contemporary gathering space. The GOURMET KITCHEN is designed to impress showcasing crisp white cabinetry, stone countertops, a classic subway tile backsplash, stainless steel appliances, a GAS COOKTOP, built-in ovens, a generous closet pantry, an oversized breakfast bar and butler pantry. NEW LIGHTING in both the Kitchen and Dining area adds the perfect finishing touch. Elegant ARCHED DOORWAYS in the Dining Room lead to a spacious Family Room, offering even more room to gather and relax. Sliding glass doors open to the covered, SCREENED BRICK-PAVER PATIO and fenced yard—the perfect setting for morning coffee, while the adjoining open-air patio provides an ideal space for grilling, dining under the stars, or soaking up the Florida sunshine. Upstairs, an EXPANSIVE LOFT creates the perfect flex space for a media room, game room, playroom, or home office. The luxurious Primary Suite is a peaceful retreat featuring an ELEGANT TRAY CEILING and French doors that open to a private balcony. The SPA-INSPIRED EN SUITE BATH offers dual vanities, a huge walk-in shower with built-in bench seating, a private water closet, and a generous walk-in closet. Two additional spacious bedrooms and another full bath provide comfortable accommodations for family and guests. Even better, this home is just a SHORT STROLL from the community's incredible RESORT-STYLE AMENITIES, including a spectacular pool, a clubhouse, state-of-the-art fitness center, and two playgrounds, all OVERLOOKING THE SCENIC BEAUTY of Johns Lake. Perfectly positioned in the heart of Winter Garden, you'll enjoy EASY ACCESS to the charm of Downtown Winter Garden, featuring award-winning restaurants, boutique shopping, weekly farmers markets, and year-round festivals. Outdoor enthusiasts will love the nearby WEST ORANGE TRAIL, while boating, fishing, and water recreation await on Johns Lake. You're also JUST MINUTES from Disney Springs, Walt Disney World Resort, Universal Orlando Resort, Winter Garden Village, and Hamlin Town Center. Combining LUXURY FINISHES, exceptional community amenities, and one of Central Florida's most desirable locations, this remarkable home offers the lifestyle you've been dreaming of. Don't miss your opportunity to make it yours!

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

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

Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 1950 Pantheon Drive, a charming 3-bedroom, 2-bath home located in the desirable Alexander Ridge community of Winter Garden. Offering 1,769 square feet of living space, this thoughtfully designed split-bedroom floor plan provides comfort, privacy, and easy everyday living. From the moment you arrive, the home makes a welcoming first impression with a bright exterior, paver driveway, covered entryway, mature landscaping, and a large front tree that adds shade and curb appeal. Inside, the open living, kitchen, and dining areas create a functional flow for relaxing, gathering, and entertaining. The living room features warm engineered wood flooring, neutral tones, and natural light from multiple windows, creating a bright and inviting main living space. The kitchen overlooks the living area and features granite countertops, warm wood cabinetry, stainless steel appliances, pendant lighting, recessed lighting, a breakfast bar, a center island, a deep kitchen sink, and a modern pull-down faucet.  Just beyond the kitchen, the dining area provides a dedicated space for meals while remaining connected to the heart of the home. The private primary suite offers neutral tones and direct access to the ensuite bathroom. The primary bath features dual sinks, granite countertops, warm wood cabinetry, upgraded lighting, a walk-in shower with a glass enclosure, a separate soaking tub, and direct access to the walk-in closet. The walk-in closet also includes convenient door access to the laundry room, adding a smart everyday function. Bedrooms 2 and 3 are located on the opposite side of the home and share a spacious second bathroom. Recent updates include HVAC replaced in August 2024, PAID OFF Solar Panels in 2018, ROOF installed in 2023. The solar system is paid off, helping create an energy-efficient home with low-cost utilities. Alexander Ridge offers inviting community amenities, including a resort-style pool with paver decking, lounge areas, a covered pavilion, playground, open green space, and beautifully maintained common areas surrounded by mature landscaping and palm trees. This Winter Garden home blends comfort, function, efficiency, and community living in one inviting package.

Listing is courtesy of: EXP REALTY LLC (407-641-2808)

Listing Agent: Todd Schroth, Pa (407-641-2808)

Remarks: Welcome to your own piece of Downtown Winter Garden paradise! This beautifully maintained 3-bedroom, 2.5-bathroom residence, built in 2019, offers the perfect blend of modern comfort, thoughtful design, and an unbeatable location just moments from one of Central Florida's most sought-after historic downtowns. Ideally situated just a short stroll from the award-winning Winter Garden Farmers Market, this exceptional home places you in the heart of one of Florida's most vibrant communities. Walk to the renowned Crooked Can Brewing Company, Garden Theatre, boutique shopping, charming cafés, and an outstanding selection of local restaurants, wine bars, and entertainment venues. Whether enjoying a weekend brunch, an evening out, or one of the many community events held throughout the year, everything Downtown Winter Garden has to give is just minutes from your front door. Inside, you'll immediately appreciate the bright, open-concept layout designed for comfortable everyday living and effortless entertaining. The spacious kitchen overlooks the living and dining areas, creating a warm, inviting atmosphere where family and guests naturally gather. Featuring modern finishes, generous cabinetry, quality appliances, and ample counter space, the kitchen is ideal for casual meals or hosting dinner parties. The highly desirable first-floor primary suite provides privacy and convenience with an en-suite bathroom and generous closet space. Also on the first floor are the laundry room, convenient half bath, and direct access to the attached two-car garage. Upstairs are two additional well-proportioned bedrooms and a full bathroom, creating the ideal setup for family, guests, or a dedicated home office. A standout feature is the dedicated surround-sound movie theatre, creating the ultimate in-home entertainment experience for movies, sporting events, and family movie nights. Step outside to your own peaceful retreat. The recently created butterfly garden provides a colorful outdoor sanctuary, thoughtfully landscaped to attract butterflies and pollinators while creating the perfect place to relax with your morning coffee or unwind after a busy day. Built in 2019, this home offers the advantages of modern construction, energy-efficient features, and low-maintenance living while combining timeless curb appeal with an exceptional floor plan. Opportunities to own a newer home within minutes of Historic Downtown Winter Garden are rare. Whether you're looking for a primary residence, a lock-and-leave lifestyle, or simply want to enjoy one of Central Florida's most desirable communities, this property delivers an exceptional combination of location, comfort, and lifestyle. Experience everything that makes Winter Garden one of Florida's most celebrated places to live—from its tree-lined streets and award-winning Farmers Market to the renowned West Orange Trail, live entertainment, breweries, dining, shopping, and year-round community events—all just a short walk from your front door. Agent is the Owner.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Lloyd Hart (855-450-0442)

Remarks: Commanding stunning views of Johns Lake, 16038 Johns Lake Overlook Dr rests in the desirable Hickory Hammock community of Winter Garden a lakefront enclave where natural beauty meets elevated, everyday luxury. This is more than a home; it's a lifestyle designed for those who appreciate space, comfort, and the calming presence of water just beyond their windows. Inside, 4,139 square feet unfold across a thoughtful, flexible layout with five bedrooms and five bathrooms. The main level anchors the home with two generous suites, including a refined primary and an oversized guest suite. Each offers serene water views, spa-inspired bathrooms, and a true sense of privacy that makes hosting effortless. Venture upstairs to discover a second secluded primary suite your personal sanctuary. Here, you can wake to panoramic lake views, relax in the garden bath, or step onto your private balcony to take in unforgettable sunsets over the water. The heart of the home is an open concept living area that flows seamlessly into a chef's dream kitchen. Premium appliances, gleaming granite countertops, and custom cabinetry create a space equally suited for quiet mornings and lively gatherings. When it's time to unwind, a dedicated theatre loft provides the perfect setting for movie nights and lazy weekend afternoons. Step outside, and the entertaining possibilities feel endless. The expansive outdoor living area boasts a full outdoor kitchen finished in Brazilian granite, a sparkling pool with an infinity edge hot tub, and multiple spaces for lounging and dining beneath the Florida sky. Just steps away, your covered private boat dock complete with boat and jet ski lifts opens the door to endless days of boating, fishing, and watersports on Johns Lake. For those who love to play, the backyard even includes a 5-hole putting green and a 2-hole chipping green, ideal for sharpening your short game without ever leaving home. Every detail here reflects a rare blend of craftsmanship, comfort, and connection to the water. Surrounded by natural beauty and premium amenities, this property delivers the kind of tranquil lakefront living that so many search for and so few ever find. Opportunities to own a home like this, in one of Winter Garden's most sought after communities, simply don't come along often. Come experience it for yourself, and imagine the life waiting here. Schedule your private showing today before this exceptional retreat is gone!

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

Listing Agent: Drew Belani (407-203-9441)

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. Welcome to 14779 McClane Road! Set behind the gates of Oxford Chase, this one of a kind Mattamy home stands apart from anything else in the community. Five bedrooms, four baths, and 3,118 square feet of genuinely upgraded living on a lot that simply cannot be replicated. At the heart of it is a custom designed kitchen any chef would love to call their own. A dramatic waterfall edge stone island seats four beneath designer glass pendants, surrounded by crisp white cabinetry, a deep stainless farmhouse apron sink, a gas cooktop beneath a vented stainless chimney hood, and a full stainless double wall oven. It opens directly into the great room and flows to a formal dining room crowned by a tray ceiling, bay window, and cascading crystal chandelier. Large stone look tile runs continuously through every common area with no transitions and no compromises. The attention to detail carries throughout. Every bathroom features tile taken floor to ceiling in the shower surrounds, accented by a custom glass mosaic inlay band. The first floor primary offers privacy and generous proportions, while a main floor laundry room adds a deep storage closet, the kind of everyday storage that makes a home genuinely functional. Upstairs is where this floor plan gets extremely special. A spacious loft paired with its own full bathroom creates a genuine second living quarters, not a bonus room with a powder bath down the hall. Aging parents get real independence. Young adults returning home get privacy and dignity. An au pair, a long term guest, or a live in caregiver has a complete suite of their own. It is the kind of true multi generational layout families search for and rarely find. An oversized 3 car garage with an extra deep bay handles the vehicles, the workshop, and everything in between. Step outside and the setting speaks for itself. An oversized covered lanai opens onto a wide, open lawn with no rear neighbors and no homes across the way. The protected retention area means that openness is permanent, not a temporary view waiting to be built out. The yard is already pre wired for a pool, so your private resort is ready whenever you are. A walking trail sits just a short stroll from your door. And nearly every night, you can finish dinner on the lanai and watch Disney's fireworks light up the sky, visible from multiple vantage points throughout the home. The location may be the quietest luxury of all. SunRidge Elementary and SunRidge Middle are an easy walk from your front door. AdventHealth Winter Garden sits roughly five minutes away. Minutes in the other direction, the new $31 million Tucker Ranch wellness complex is bringing a teaching farm, botanical gardens, retreat center, and fitness trail system, joining the existing 200 acre nature preserve on Johns Lake with its kayak launch and miles of trails. Plant Street's restaurants and award winning Farmers Market, Winter Garden Village, and quick access to the 429 are all close at hand, with Orlando International Airport about 30 minutes out. Homes in Oxford Chase rarely come available, and lots like this one almost never do. Seller offering a $1,000 paint allowance and a $500 cleaning allowance to buyer at closing. Schedule your private showing today!

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

Listing Agent: Ryan Persaud (646-404-3085)

Remarks: Under contract-accepting backup offers. Just remolded!!!Large 4-bedroom home + 2 large Bonus rooms. This 2782sf 7-year-old home is in the awesome community of Lakeside just west of the Winter Garden Village about 4 miles. The home has tons of space, humungous kitchen and Master bedroom downstairs along with bedroom #2 and 3, and with a full bath. The first floor is gorgeous tile from the front door throughout up to the bedrooms. Coffered details in high ceilings, arched openings and a back yard looking over a green retention area. This Hampshire plan has a split plan with 2 bedrooms and full bath near the front of the house first floor. Walking past the flex room that can be used for formal dining, office, etc to the main open living area with living, dining, and kitchen. The kitchen is large with TONS of tall 42 inch raised panel cabinetry and walk-in pantry. The beautiful light brown speckled granite is accented by medium Brown cabinets and all stainless-steel appliances with the stove fueled with gas. A walk-in pantry and Island sink with breakfast bar look out to the open living room and dinette. Dinette has large windows on 3 sides to embrace the outside nature. The main living area has a 3-panel slider door to open wide to the paved, covered Lania that overlooks a good-sized back yard with a large field retention area beyond. Past the living room through the arched entry into the large primary bedroom. Ceiling fan and high coffered detailed ceilings and a huge bath with a seated walk-in shower separating two individual vanities on large cabinets for lots of storage. Large walk-in closet, separate toilet room, and linen closet. Washer and dryer have their own room near the garage. Take a quick step upstairs to a HUGE open loft, 4th bedroom and 3rd full bath. full bath. This home has a 2 car garage and gas heated Tankless water heater. This home is located in the awesome community of Waterside at Johns lake, with an incredible huge pool lakeside, playground, dock, clubhouse, state-of-the-art fitness center

Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)

Listing Agent: Chun Cai (951-699-4983)

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: Virtually Staged. Lender Credit of 1% (of loan amount) toward closing costs or rate buy-down (inquire for more info). Welcome to CARRIAGE POINT, a GATED Winter Garden community offering an exceptional location and a thoughtfully designed floor plan. This two-story POOL home delivers the space today’s buyers crave, room for everyone, from dedicated home offices to flexible living and guest areas. With 3,435 square feet of living space, this home features five bedrooms, four full bathrooms, and a large bonus room. As you enter the home, you are welcomed by a spacious living room and dining room before continuing into the heart of the home. The open-concept kitchen features granite countertops, 42-inch cabinetry with crown molding, under-cabinet lighting, a gas range, an expanded pantry, and plenty of space for a breakfast table. The kitchen opens to the family room with sliding doors leading out to the SCREENED-IN POOL and FENCED backyard. The first floor features a desirable three-way split floor plan with four bedrooms and three full bathrooms. The spacious downstairs primary suite offers plenty of room to relax, along with a walk-in closet and private en-suite bathroom. Upstairs provides even more flexibility with a fifth bedroom, fourth full bathroom, and a large living area. Newer luxury vinyl plank flooring extends throughout the upstairs and staircase. The outdoor living space is a true highlight of this home with an expansive screened-in SALT WATER POOL ADDED IN 2021. Designed with both relaxation and fitness in mind, the pool features water jets giving a swim-against-the-current feature, creating the perfect space to enjoy a refreshing swim or get in a low-impact workout. Carriage Pointe offers residents a variety of community amenities including a tennis court, playground, soccer field, and walking path. For those who enjoy an active lifestyle, the area offers miles of scenic trails, including the West Orange Trail, along with parks and outdoor activities nearby. The location is ideal, with convenient access to State Road 429 and Highway 50, making travel throughout Central Florida easy. Enjoy being close to Winter Garden Village, the Hamlin area, restaurants, shopping, entertainment, and AdventHealth Winter Garden. Families will appreciate the HIGHLY RATED SCHOOLS, including Whispering Oak Elementary, Hamlin Middle School, and West Orange High School. Historic Downtown Winter Garden is less than five miles away and offers charming shops, local restaurants, the weekly farmers market, the West Orange Trail, and year-round community events. Additional features include a three-car garage, natural gas service through Lake Apopka Natural Gas District, gas washer and dryer, a 2020 water heater, updated electrical service, and added electrical for a built-in microwave. With its exceptional floor plan, private pool, flexible living spaces, and prime Winter Garden location, this Carriage Pointe home offers exceptional space, comfort, and convenience. Schedule your private tour today!

Listing is courtesy of: EXP REALTY LLC (407-305-4300)

Listing Agent: Justin Core (407-305-4300)

Remarks: *Walkthrough Video Available* Welcome to the gated Emerald Ridge neighborhood that is conveniently located near the 429, Turnpike, shopping and restaurants in Winter Garden, Horizon West and Windermere as well as the charming downtown Winter Garden Plant Street and all of the local activities it brings. Cool off in the COMMUNITY POOL and enjoy staying active on the sidewalks that run throughout the neighborhood. This home has an OPEN FLOOR PLAN that greets you as soon as you enter. The spacious living room has nice natural lighting and opens to the eat-in kitchen which was recently remodeled. You’ll find NEW CABINETRY with soft-close doors, a TILE BACKSPLASH and STAINLESS STEEL appliances. The WALK-IN PANTRY is a dream as it gives storage space for kitchen wares and laundry needs. Sliding doors open to the SCREENED PATIO so you can enjoy the evening breeze. There’s a SPACIOUS LOFT upstairs which makes for a fantastic 2nd living room, home office, play space, or home gym. The primary suite in this model is extra large giving room for a sitting area! The WALK-IN CLOSET offers plenty of space to keep your wardrobe organized and the en-suite bathroom has a garden tub and separate shower. The secondary bedrooms share a hall bathroom. The ROOF, AC, AND WATER HEATER WERE REPLACED IN 2018. Additional upgrades include CROWN MOLDING and canned lighting throughout the home.

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

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

Remarks: Welcome to established Regency Oaks subdivision in Stonecrest, in the heart of Winter Garden! Situated on a desirable corner lot, this screened-in POOL home offers an incredibly flexible floor plan designed to fit today's lifestyle. Listed as a 3-bedroom home, it also features a spacious flex room overlooking the pool and backyard, along with a separate oversized bonus room that can easily serve as an additional bedroom, home office, media room, playroom, fitness studio, guest retreat, or additional living space. The split-bedroom layout provides privacy, while the primary suite features a walk-in closet, garden tub, and separate shower. Fresh interior paint and updated laminate flooring enhance the home's inviting feel. Step outside to your private backyard oasis complete with a sparkling pool, mature shade trees, a side yard for gardening and a pool safety fence—creating the perfect setting for entertaining or relaxing while enjoying Florida's indoor-outdoor lifestyle. Recent improvements include a new roof (2023), 2017 air handler, 2018 A/C condenser, and a recently serviced irrigation system for added peace of mind. Residents of Regency Oaks enjoy low monthly HOA fees and outstanding community amenities including scenic walking trails around a picturesque pond with benches, a clubhouse, community pool, and two neighborhood parks/playgrounds. Ideally located walking distance of Winter Garden Village at The Grove and just minutes from Historic Downtown Winter Garden, the West Orange Trail, major highways, shopping, dining, entertainment, top rated schools and Central Florida's world-famous attractions. Orlando International Airport and Florida's east coast beaches are both approximately an hour away.

Listing is courtesy of: METRO CITY REALTY (407-237-3331)

Listing Agent: Beatrice Miranda (407-592-4448)

Remarks: Virtually Staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown shops and restaurants, this home beautifully blends modern luxury with small-town charm. Step inside to discover designer finishes and thoughtful craftsmanship throughout. The gourmet kitchen features top-end Monogram appliances, including a 36” dual-fuel range, warming oven, and a 48” side-by-side refrigerator and freezer. Upgraded quartz countertops, a brick backsplash and hearth with built-in electric fireplace, and engineered hardwood floors elevate the open-concept main living areas. Additional luxury touches include Brizo faucets, custom plantation shutters, and floating shelving systems in every bedroom closet. The owner’s suite offers a spa-inspired retreat with a 6-foot soaking tub, while the upgraded pantry with butcher block countertop, dimmer switches, and ceiling fans throughout enhance everyday comfort. An in-law suite featuring a full bath, family room, and a private staircase above the garage provides the perfect space for guests, extended family, or a private home office. Enjoy peaceful mornings and sunset evenings from the screened front and side porches, adding to the home’s charm and livability. Located in Oakland Park, residents enjoy resort-style amenities including two community pools, multiple parks and playgrounds, scenic walking and biking trails, a clubhouse, and direct access to the West Orange Trail. With tree-lined streets, lake views, and friendly front-porch living, this award-winning community captures the very best of Winter Garden living.

Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)

Listing Agent: Kevin Sullivan (321-663-3457)