Start your Winter Garden Home Search

Winter Garden is a bustling urban town with over 38,000 residents. It is almost the home of several schools, like Lake Whitney Elementary School, Bridgewater Middle School, and West Orange High School. Only 30 minutes out of Orlando, the town is the perfect distance from the city for commuters.

Community and Events

Winter Garden bolsters its sense of community with a plethora of events, especially around the holidays. For example, in December, they proudly present a number of activities for families to attend: light shows, hayrides, movie nights, a parade, musical performances, and some Santa Clause sightings of course! Some year-round events include live performances every Friday at the Plaza in Downtown Winter Garden and their weekly Farmers Market. If you're looking for things to do inside, Winter Garden provides several options. Their Heritage Museum delves into the town's past with over 5,000 artifacts to look through. The Central Florida Railroad Museum explores the role of the railroad in Florida's past -- a fun history lesson for people of all ages. The Winter Garden's Art Association's community center offers a neat gallery with exhibits and workshops for all. When you need to check out a book, make sure to visit the Winter Garden Branch of the Orange County Library System. Go to the Garden Theatre for a wonderful performance for a night out.

See more Winter Garden Events on their website!

Brand Winter Garden Listings

$230,000
3 Beds ⋅ 3 Baths ⋅ Westside Townhomes Phase 2 19/100 Lot 5 Blk 11 SubDv. ⋅ 34787 Zip Code
Beautiful Family-Oriented Townhouse in a Great Location! Well-maintained and move-in ready, this home offers low-maintenance living with a low HOA fee. Conveniently located approximately 10–17 miles from Walt Disney World, Disney Springs, and many of Orlando’s top entertainment destinations. Easy access to major highways makes commuting and exploring the area convenient. A wonderful opportunity for a family, second home, or investment property. More photos coming soon!

988 Stucki Terrace, Winter Garden
$749,000
4 Beds ⋅ 3 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code
Welcome home to this stunning pool home with a beautiful water view in desirable Westfield Lakes! Offering 2,335 square feet in a triple-split design, this home features a screened pool overlooking the water and an impressive list of recent improvements, including roof (2023), AC (2019), water heater (2023), whole-home repipe (2021), pool resurfacing and new tile (2020), repainted kitchen cabinets (2026) and fully remodeled bathrooms. Enjoy the Florida lifestyle from your screened pool and lanai, whether starting the day with coffee by the water, taking an afternoon swim or entertaining family and friends. Westfield Lakes is known for its mature tree-lined streets, beautifully landscaped entrances and welcoming neighborhood atmosphere. Residents enjoy Lake Beulah with two fishing docks, scenic ponds with lighted fountains, tennis and pickleball courts, and two playgrounds. The neighborhood is also home to abundant wildlife, including sandhill cranes, herons, egrets, bald eagles and owls. With the Roper YMCA, Southwest Aquatics and two dog parks nearby, this home offers a wonderful combination of space, recreation and convenience. A screened pool, peaceful water view, major updates and plenty of space all in beautiful Westfield Lakes.

12021 Windstone Street, Winter Garden
$925,000
5 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code
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 intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 5 bedrooms, 4 full bathrooms, a loft, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and a refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. Three additional first-floor bedrooms and two bathrooms provide comfort and privacy for everyone. Upstairs, enjoy an additional 709 square feet of flexible living space, complete with a generous loft, private fifth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

285 Crystal Wood Drive, Winter Garden
$724,999
4 Beds ⋅ 4 Baths ⋅ Waterside/Johns Lk-Ph 2a SubDv. ⋅ 34787 Zip Code
FORMER BUILDER MODEL HOME - and it shows. When a builder builds their own model, they hold nothing back, and this 4-bedroom, 3.5-bath, 2,958 sq ft home in Waterside on John's Lake is the proof: Upgrades everywhere! Gourmet kitchen with stacked cabinets, 8-foot doors throughout, recessed lighting, wood panel on ceiling, a whole-home speaker system, plus so much more! A finish package that is nearly impossible to replicate today. The open kitchen-living-dining space was designed to entertain. The kitchen is finished wall to wall with stacked upper cabinets plus crown molding, lighted glass-front uppers, quartz countertop, double built-in ovens, gas cooktop, decorative tile backsplash and an oversized island with seating. A butler's pantry and a fully built-out walk-in pantry with its own seating area keep everything in place, and the laundry room is also finished with custom cabinetry, a sink and extra countertop space. Across the room, a floor-to-ceiling stacked-stone wall anchors the living area, with an electric fireplace and the TV and entertainment system built right in, framed by lighted shelving and cabinets. A dedicated study sits off the dining room with its own work island, wall-to-wall shelving and a wood-planked ceiling. A first-floor bedroom with an en-suite bath makes an ideal guest or in-law suite, plus a powder bath for visitors. Upstairs, the primary suite features a wood beam ceiling and a walk-in closet outfitted with a custom shelving system. The primary bath is built around an oversized walk-in glass shower spanning an entire wall, with dual vanities opposite. Two additional bedrooms, a full bath, and a generous loft with a built-in media center complete the second level. Bidets in the baths. Engineered hardwood in the loft and primary bedroom, wood-look tile downstairs. Outside, a screened lanai with a tongue-and-groove wood ceiling opens to a private paver courtyard. The 2-car garage is already fitted with a NEMA 14-50 EV charging outlet, providing extra storage and parking for your Tesla or other electric car. Best of all: NO FRONT NEIGHBORS. The community pool and amenity center sit directly across the street with plenty of guest parking, and there are water views of John's Lake from the front of the home. Waterside on John's Lake offers something most communities do not: a true lap pool with lane markers for training and distance swimming, plus a separate leisure pool. Add a playground, fitness center, clubhouse and oak-canopied trails with picnic and grill areas leading to a lakefront pier for an evening walk or a little fishing. Minutes from Winter Garden Village, Hamlin and SR-429, with downtown Winter Garden's Plant Street, farmers market and the West Orange Trail just up the road - and Disney a short drive away. Model homes are built to sell a neighborhood. Here is your chance to own one - schedule your private showing today.

16924 Tradewind Point, Winter Garden
$520,000
3 Beds ⋅ 2 Baths ⋅ Waterleigh Phase 4a SubDv. ⋅ 34787 Zip Code
WELCOME TO WATERLEIGH – RESORT-STYLE LIVING IN WINTER GARDEN! “TENANT-OCCUPIED – START GENERATING RENTAL INCOME FROM DAY ONE” Discover this beautiful 3-bedroom, 2-bathroom single-family home located at 16704 Point Rock Drive in the highly desirable Waterleigh community of Winter Garden. This well-designed home features a bright OPEN-CONCEPT FLOOR PLAN that seamlessly connects the living, dining and kitchen areas, creating a comfortable space for everyday living and entertaining. The home also offers a 2-CAR GARAGE and a functional single-story layout. What truly sets this property apart is the WATERLEIGH LIFESTYLE. Residents enjoy access to an impressive collection of resort-style amenities, including multiple community pools and amenity centers, fitness centers, playgrounds, sports fields, mini-golf, beach volleyball, community garden, walking and nature trails, scenic lakes and ponds, and beautiful outdoor spaces throughout the community. Waterleigh offers the perfect combination of residential comfort and resort-style living in one of Winter Garden's most desirable areas. Conveniently located near shopping, dining, schools, entertainment and Central Florida's world-famous attractions, with easy access to major roadways connecting you to the greater Orlando area. Whether you're looking for your primary residence or a home where you can enjoy the Florida lifestyle every day, this property offers much more than a house—it's an opportunity to become part of the Waterleigh lifestyle. Schedule your private showing today!

16704 Point Rock Drive, Winter Garden
$749,999
4 Beds ⋅ 5 Baths ⋅ Burchshire SubDv. ⋅ 34787 Zip Code
Experience luxury and versatility in this exceptional CUSTOM 2025-BUILT RESIDENCE, where thoughtful design, impressive scale, and high-end finishes come together to create a truly one-of-a-kind home. Featuring 4 BEDROOMS AND 5 PRIVATE ENSUITE BATHROOMS, WITH EVERY BEDROOM FEATURING ITS OWN ENSUITE, this home offers an extraordinary level of comfort, privacy, and flexibility rarely found in Winter Garden. Designed with luxury in mind, the home showcases 12-FOOT CEILINGS THROUGHOUT, including the impressive 2-CAR GARAGE, elegant PORCELAIN TILE FLOORING, and CUSTOM MATCHING QUARTZ COUNTERTOPS THROUGHOUT THE KITCHEN AND FURNITURE TOPS. Each ensuite bathroom features its own UNIQUE CUSTOM DESIGN, with spacious layouts, luxurious finishes, and distinctive details that give every bathroom its own character. The expansive open-concept living areas create an incredible atmosphere for both everyday living and entertaining, while the ENCLOSED FRONT LANAI, REAR LANAI, AND PAVED PERGOLA extend the living space outdoors and provide multiple areas to gather, relax, and enjoy the Florida lifestyle. The home's flexible design offers even more potential. Two bedrooms are currently separated by a drywall partition originally incorporated for an Airbnb concept, which can easily be removed to create a more open configuration or customized to suit your needs. Whether you're looking for an impressive primary residence, a multigenerational home, private guest accommodations, or an investment opportunity, this property offers flexibility that is hard to find. Opportunities like this are rare. Located just minutes from Downtown Winter Garden and within the coveted Golf Cart District, residents can enjoy easy access to Plant Street, the weekly farmers market, local dining, boutiques, breweries, parks, community events, and the West Orange Trail. Zoned for “A-RATED” Tildenville Elementary and West Orange High School, this home brings together everything today's buyer is looking for — custom construction, exceptional space, luxury finishes, versatility, and an unbeatable location. This isn't simply a new home — it's a custom-built opportunity designed to stand out.

809 Burch Avenue, Winter Garden
$795,000
5 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Luxury living in the ENZO Model townhome located in Lakeshore Preserve, a Toll Brothers community surrounded by million-dollar homes in Winter Garden. This spacious executive style townhome offers 5 bedrooms, 4 bathrooms, and over 3,100 square feet of living space, including a private 1-bedroom apartment with kitchenette above the garage and its own private entrance perfect for guests, multigenerational living, or a student retreat. Built in 2017, this home features an open concept layout, Wolf gas cooktop, two gas tankless water heaters, whole home water softener, and two A/C systems with Nest thermostats. Recent updates include luxury vinyl flooring throughout the downstairs, all new carpet installed upstairs and in all bedrooms, and plantation shutters, adding both style and functionality. The home has also been upgraded with over $20,000 in custom closet systems, providing exceptional storage, organization, and convenience throughout. Enjoy the extended wrap around front porch, private courtyard, and even views of Disney fireworks and space launches from the front of the home. Lakeshore Preserve offers resort style amenities including a lakefront clubhouse, fitness center, pool, lake access, kayak launch, volleyball court, firepit, and dog park. Conveniently located near Disney, Hamlin shopping and dining, Flamingo Crossings, Orlando Health, and top rated schools. HOA includes exterior maintenance, cable, internet, and community amenities. A rare opportunity to own a luxury townhome in one of Winter Garden’s most desirable communities.

8866 Bismarck Palm Drive, Winter Garden
$839,000
6 Beds ⋅ 4 Baths ⋅ Fullers Oak SubDv. ⋅ 34787 Zip Code
Come view this beautiful new Meritage UPGRADE home in FULLERS OAKS at the corner lot and big back yard you can build your dream pool . Perfect opportunity for you to own and enjoy a beautiful energy-efficient home all year long. This home is a SIX -bedroom, four-bath, three-car garage p with lots of natural lighting.a The floor plan includes a gourmet kitchen, granite countertops, a huge walk-in pantry, The beautiful kitchen also includes stainless steel appliances and 42-inch designer cabinetry with crown molding. Also, on the first floor, you will find an oversized office/bonus room and a guest bedroom with a separate full bath. You will love the huge master suite located on the second floor, featuring granite vanities, a glass walk-in shower, garden tub, separate toilet room and a huge walk-in closet. On the second floor, you will love the other three bedrooms, each with huge walk-in closets, two large walk-in closets in the hallway, which gives you plenty of space for everything you own and a huge media room that will be great for family movie night. The possibilities in this home are endless, something you will not want to miss.cAllister Landing is Located just a few minutes from the shops, restaurants and entertainment in Historic Downtown Winter Garden, McAllister Landing offers lakeside living in large, beautiful homes. Community amenities will include a dock on Lake Apopka, parks and walking trails. it is short drive to winter garden village and 5 min to turnpike , at winter garden but without winter garden rush hour traffic 25 min from downtown , 20 min from Maitland come see it yourself

1707 Fullers Oak Loop, Winter Garden
$375,000
3 Beds ⋅ 3 Baths ⋅ Stone Crk SubDv. ⋅ 34787 Zip Code
PRICED TO SELL! STONE CREEK -Sought After Community in Winter Garden, Great Open Floor Plan "The Cypress" with 1846 sq ft under air, Kitchen has newer stainless-steel appliances, washer and dryer also included. Practical floor plan with large loft area perfect for remote workers or additional living space. Double car garage, large fenced in yard big enough to add a pool! Nice walkable community with spacious park/playground, benches and walking areas. Excellent Location in Central Florida- Approximately 10 minutes to downtown Winter Garden shops, restaurants and entertainment. 5 Minutes to the 429 Expressway!!! 20 Minutes to Downtown Orlando, 30 minutes to Disney and attractions. Looking for a Cash Buyer!

15279 Harrowgate Way, Winter Garden
$1,349,000
4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 2 & 5 SubDv. ⋅ 34787 Zip Code
Ideally located in the highly sought-after Hamlin area of Winter Garden, this beautifully maintained pool home offers the perfect combination of comfort, convenience, and Florida living with beautiful lake Hancock views. Enjoy easy access to shopping, dining, entertainment, major roadways, outdoor recreation, and the many attractions and amenities throughout Winter Garden and Horizon West. Designed for effortless everyday living and entertaining, the residence features bright, spacious interiors that flow seamlessly into the outdoor living area. The private saltwater pool can be heated using either solar energy or gas, providing flexibility and year-round enjoyment. Fully paid-off solar panels offer an exceptional advantage, with no solar lease or financing obligation for the new owner. Additional improvements include one brand-new air-conditioning system, a second A/C system replaced less than three years ago, and a whole-home water softener and filtration system with reverse osmosis for drinking water. Fresh landscaping enhances the home’s curb appeal and creates a welcoming first impression. With its energy-efficient features, valuable recent upgrades, resort-style outdoor space, and desirable location, this move-in-ready property presents an exceptional opportunity to enjoy the best of the Winter Garden lifestyle.

15240 Shonan Gold Drive, Winter Garden
$675,900
4 Beds ⋅ 3 Baths ⋅ Johns Landing SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful and impeccably maintained 4-bedroom, 2.5-bath home in the desirable Johns Landing community of Oakland! This exceptional family home offers space, comfort, flexibility, and all the features buyers are looking for. The spacious floor plan includes a large bonus room and an additional room currently being used as an office, which can easily be converted back to a bedroom to suit your family's needs. The heart of the home is the generously sized kitchen, complete with a convenient kitchen nook—perfect for everyday meals, morning coffee, and family gatherings. Wood and carpet flooring add warmth and character throughout the home. Step outside and prepare to be impressed by the enclosed patio, featuring a spectacular built-in bar and entertaining area that truly sets this home apart. It is the perfect place to relax, entertain family and friends, watch the big game, or create unforgettable memories year-round. This home has been lovingly cared for and is immaculate inside and out. The roof is approximately three years old, the water heater is approximately three years old, and the air-conditioning system was recently serviced approximately three months ago. Located in the gated Johns Landing community, residents enjoy an array of amenities and recreational opportunities. This is more than a house—it is a beautiful place to call home, with the space, features, and flexibility today's buyers desire. Come see it for yourself—you'll immediately appreciate the pride of ownership and everything this special home exemplifies. Schedule your private showing today; this one is truly worth seeing!

239 Largovista Drive, Oakland
$770,000
4 Beds ⋅ 3 Baths ⋅ Panther View SubDv. ⋅ 34787 Zip Code
Welcome to 14975 Winter Stay Drive, where the work has already been done and the upgrades go far beyond builder basics. Thoughtfully improved inside and out, this Horizon West home pairs a warm, finished feel with the kind of practical upgrades you will appreciate for years to come. At the heart of the home, the kitchen features KitchenAid appliances installed in 2024. LVP flooring was added in 2025 and flows throughout the bedrooms. Plantation shutters, installed in 2026, add a polished finishing touch. Even the laundry room has been elevated with built-in cabinetry, granite countertops and additional storage. Outside is where this home really sets itself apart. The custom gunite pool, completed in 2024, features a swim shelf, heater AND chiller, upgraded screen enclosure and child safety fence, making it just as enjoyable in the heat of summer as it is on a cool Florida evening. The covered lanai was transformed into an outdoor living space with a fireplace, TV accent wall and recessed lighting, creating a true extension of the home for entertaining or relaxing year-round. The upgrades continue behind the scenes with a fully paid 15kW solar system, generator back-feed hookup, French drains along the east-facing gutters and downspouts, and overhead garage storage racks. Located in Winter Garden's sought-after Horizon West area, this is a home that has been intentionally upgraded, carefully maintained and designed to be lived in. Skip the projects and start enjoying the pool, the outdoor living space and everything this home has to offer from day one.

14975 Winter Stay Drive, Winter Garden
$569,500
4 Beds ⋅ 4 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
Welcome to resort-style living in the highly desirable Waterleigh community! This beautifully maintained home combines comfort, thoughtful upgrades, and an incredible Horizon West location just minutes from Walt Disney World. Upon entering, you’ll find a private first-floor bedroom complete with a walk-in closet and its own full bathroom, creating an ideal space for guests, extended family, or a private home office. Continue into the open-concept living and dining areas, where the spacious layout provides the perfect setting for everyday living and entertaining. The interior was professionally painted and enhanced with upgraded Hunter ceiling fans throughout, updated vanity and lighting fixtures, a new entry pendant light, and a beautiful dining room chandelier! Upstairs, the spacious primary suite features a large walk-in closet and private en-suite bathroom. Two additional generously sized bedrooms provide plenty of space for family, guests, or a home office. The upstairs loft adds valuable flexible living space and is just steps from your private screened-in balcony, complete with an exterior ceiling fan, creating the perfect place to relax and enjoy the Florida evenings! Step outside to the screened-in lanai featuring FLORIDA GLASS for additional privacy and comfort, overlooking a FULLY FENCED backyard. Additional improvements include RAIN GUTTERS, a newer washing machine, a transferable Massey Total Coverage Termite Protection Plan with the most recent renewal completed in August 2026, and an HVAC Platinum Plus Maintenance Plan with preventative maintenance most recently completed in May 2026! One of the best benefits of living in Waterleigh is the low-maintenance lifestyle, with HOA-INCLUDED LAWN MAINTENANCE allowing you to spend more time enjoying the incredible RESORT-STYLE AMENITIES, beautiful community spaces, golf cart-friendly streets, and year-round community events. Enjoy being just minutes from Disney and even catching views of the Disney fireworks from within the community. The location is hard to beat, with convenient access to shopping, dining, Publix, and everything Horizon West has to enjoy. Even more is coming to the area, including the NEW HORIZON WEST LIBRARY and HORIZON WEST REGIONAL PARK, along with a new county park featuring basketball and pickleball courts COMING SOON to the community! Families will also appreciate being zoned for highly rated local schools, including ATWATER BAY ELEMENTARY. This is more than a home, it’s the Waterleigh lifestyle. Enjoy resort-style amenities, HOA-included lawn maintenance, highly rated schools, nearby shopping and recreation, and the magic of Disney just minutes away. Schedule your private showing today and discover everything 16644 Point Rock Drive has waiting for you!

16644 Point Rock Drive, Winter Garden
$850,000
4 Beds ⋅ 4 Baths ⋅ Oakland Parkb-3 SubDv. ⋅ 34787 Zip Code
Under Construction. Rare opportunity to finish a custom AR Homes "Carrabelle" build exactly the way you want it - priced to reflect its current stage. 166 Hammock Preserve Loop is roughly three-quarters complete: framing, block construction, roof, windows, and drywall are in, and the home is currently paused at that stage. What's left is the fun part - flooring, cabinetry, fixtures, paint, and finishes - which means the next owner gets to select every surface in a 3,186-square-foot, four-bedroom, four-bath custom home instead of settling for someone else's choices. The Carrabelle plan delivers a two-story, open-concept layout on a 6,914-square-foot corner homesite in Oakland Park: a first-floor guest suite and flex room, a dramatic 21-foot foyer, an open kitchen and great room with decorative beams, a covered lanai and cabana with an open-air courtyard and fireplace, and a second-floor primary suite with a spa-style bath and walk-in closet. A three-car garage and an optional suite above it round out the plan. Full floor plan available on request. Sold AS IS. The original building permit has expired and is disclosed; a buyer will need to re-permit to resume construction. AR Homes has provided an itemized estimate to complete the home - available to serious buyers - along with the original plan set and specifications, so you're not guessing at scope. This is a straightforward, priced-to-reflect-its-stage opportunity for a buyer (or a buyer working with their own GC) who wants a real custom home in Oakland Park without paying new-construction-complete pricing for it. Located in the sought-after Oakland Park community, with tree-lined streets, walking trails, and community events, close to downtown Winter Garden's shops and dining. Cash, conventional, or construction/renovation financing. Buyer and buyer's agent to verify all information including HOA details, permit status, and completion costs. Seller makes no representations or warranties regarding the condition or completeness of existing work.

166 Hammock Preserve Loop, Oakland
$899,900
34787 Zip Code
The real story of 144 Tildenville School Road is the land. Opportunities to own over an acre this close to Historic Downtown Winter Garden are becoming increasingly hard to find. Beneath a canopy of beautiful mature trees, this property offers something that cannot easily be recreated: space, privacy, character, and a location within Winter Garden’s golf cart district. The existing 3 bedroom home offers nearly 1,500 square feet of living space, but step into the backyard and you quickly understand what makes this property special. This is land meant to be enjoyed. Picture evenings beneath the trees with string lights glowing overhead, friends gathered around the custom built pizza oven, dinner being prepared in the summer kitchen, music playing, and plenty of room for everyone to spread out. For the next owner, the possibilities are just as compelling as the lifestyle already here. Enjoy the property as it is, create your own private retreat, expand upon the existing outdoor spaces, or simply appreciate the increasingly rare luxury of having over an acre of land near the heart of Winter Garden. And despite the privacy, you are still connected to the lifestyle that makes this area so desirable. Being within Winter Garden’s golf cart district means trips toward Historic Downtown Winter Garden can become part of the routine. Spend Saturday mornings at the Farmers Market, enjoy dinner along Plant Street, explore local shops and restaurants, or spend an afternoon on the West Orange Trail before heading home to your own piece of Winter Garden. Homes can be renovated. Kitchens can be changed. Finishes can be replaced. But you cannot manufacture another acre of mature, established land in a location like this. That is what makes 144 Tildenville School Road different. It is not simply a home for sale. It is an opportunity to own a substantial piece of Winter Garden, with the space to enjoy today and the possibilities to make it something entirely your own tomorrow.

144 Tildenville School Road, Winter Garden
$415,000
3 Beds ⋅ 3 Baths ⋅ Stone Creek 48 140 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully updated 3 bedroom, 2.5 bath home in the heart of Winter Garden, perfectly positioned for convenience, comfort, and everyday living. Enjoy being just 5 minutes from Winter Garden Village, 10 minutes from Downtown Winter Garden and Plant Street Market, and walking distance to top-rated Whispering Oak Elementary. Thoughtfully updated and move-in ready, this home offers a turnkey experience with major upgrades including a Brand New Water Heater (2026), New HVAC (2022 serviced bi-annually, most recent service in August 2026), New Roof (2019), New Vinyl Fence (2022), New Kitchen Appliances (2022), Upgraded Bathrooms (2022), and an Updated Kitchen (2022). Inside, the open concept floor plan is enhanced by high ceilings and a spacious living area that overlooks the remodeled kitchen. The kitchen features a large island, quartz countertops, subway tile backsplash, ample storage, and stainless steel appliances. The adjacent dining area seamlessly opens to a screened-in patio creating an inviting space for relaxing and enjoying indoor/outdoor living. The fully fenced backyard provides shade and plenty of room for outdoor activities. Upstairs, the spacious owner’s suite features a walk-in closet and a fully remodeled ensuite bath with double vanities, tiled floors, and a glass-enclosed shower. Two additional bedrooms share an updated bathroom featuring new tile, a new vanity, and a tub. Residents also enjoy neighborhood amenities including a newer playground with sunshades and turf, along with a nearby path leading to open green space with basketball courts, baseball and soccer fields—all en route to Whispering Oak Elementary. With thoughtful updates, desirable community amenities, and an exceptional Winter Garden location, this home is ready to welcome its next owner. Schedule your tour today!

1415 Sherbourne Street, Winter Garden
$180,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort & Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
Own your piece of the Orlando vacation market at The Grove Resort & Water Park! Located on the 4th floor of Building 3, near the water park, this fully furnished 2-bedroom, 2-bath condo offers the perfect combination of a personal vacation retreat and investment opportunity. The Grove is a Walt Disney World Good Neighbor Hotel located just minutes from the parks, with complimentary shuttle service to Walt Disney World. Owners and guests enjoy resort-style amenities including Surfari Water Park with a lazy river, water slides and FlowRider surf simulator, multiple pools, spa, fitness center, mini golf, arcade, and on-site restaurants and bars. With an on-site rental management program and a prime location near Central Florida’s top attractions, this turnkey condo offers an easy, hands-off ownership opportunity while giving you your own place to enjoy when visiting Orlando.

14501 Grove Resort Avenue Unit 3403, Winter Garden
$775,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Under Construction. Step into the Mystique, a single-story new construction home situated just a short walk away from the community amenities offering 2 spacious bedrooms, 2 beautifully appointed bathrooms, an enclosed flex room—perfect for a home office or quiet retreat, and a 2-car garage with additional tandem storage space. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where 42” soft-close cabinetry meets luxurious quartz countertops and a decorative tile backsplash. The Whirlpool stainless steel appliances—including a built-in natural gas cooktop and a refrigerator—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a zero-corner sliding glass door leads to the extended covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with a spacious walk-in closet and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a rain shower head and a built-in bench, an enclosed toilet, and a linen closet complete the tranquil space. The additional spare bedroom and bathroom, along with the enclosed flex room, provide ample space for everyone. The upgraded laundry room with built-in cabinetry, quartz countertop, utility sink, and a Whirlpool washer and dryer make daily tasks a breeze. Designer-curated finishes elevate every corner of this home, including wood-look tile flooring throughout, pendant light pre-wire and under cabinet lighting in the kitchen, 2” faux wood blinds, and brushed nickel hardware and plumbing fixtures. The 2-car garage offers extra tandem storage space with an epoxy finish on the floor, ensuring that every part of your home is both beautiful and practical. With its stunning design and thoughtful touches, the Mystique home provides the perfect blend of luxury and functionality for today’s lifestyle.

13056 Sandcastle Drive, Winter Garden
$879,999
4 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to Waterleigh! This beautiful 2023-built, 4-bedroom, 3-bath home sits on a spacious lot with a peaceful natural lake view from the backyard. Featuring an open-concept layout, modern kitchen, versatile loft, and private owner’s suite. Enjoy resort-style pools, clubhouses, fitness centers, tennis courts, trails, and playgrounds. Publix is conveniently located at the community entrance, with schools, shopping, dining, SR-429, and Walt Disney World nearby. Enjoy space, views, convenience, and the best of the Horizon West lifestyle

17882 Adrift Road, Winter Garden
$490,000
4 Beds ⋅ 3 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code
Almost New & Move-In Ready! Built in 2024, this beautifully maintained corner-unit townhome offers the perfect combination of modern style, comfort, and functionality. Featuring 4 full bedrooms and 3 full bathrooms, the thoughtfully designed floor plan includes a convenient first-floor bedroom, ideal for a home office, guest suite, or private bedroom. The home showcases upgraded tile flooring throughout the main living areas and stylish granite countertops, creating a clean and contemporary feel. The spacious kitchen comes fully equipped with stainless steel appliances, including refrigerator, microwave, and dishwasher, plus a washer and dryer for added convenience. Enjoy Florida living from the screened-in back porch, perfect for relaxing or entertaining while enjoying the outdoors. A private 2-car garage located at the rear of the home provides secure parking and additional storage. Residents enjoy an impressive selection of community amenities, including a resort-style pool, fitness center, gathering area, playground, and community mailbox. With its desirable corner-unit location, modern finishes, flexible first-floor bedroom, and excellent amenities, this almost-new townhome is an exceptional opportunity for both homeowners and investors. Come see why this beautiful 2024 townhome is the perfect place to call home!

14075 Lochend Way, Winter Garden
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