Winter Garden Homes with West Orange High High school

Winter Garden Homes with West Orange High High school

Welcome to Winter Garden, Florida – a picturesque gem nestled in the heart of Orange County, where charming small-town vibes meet modern conveniences. With its rich history, vibrant community, and stunning natural beauty, Winter Garden is the perfect place to call home.

One of the standout features of this delightful city is its historic downtown area, where you can stroll along beautifully preserved streets lined with boutique shops, delectable eateries, and inviting cafes. The weekly farmers market is a local favorite, offering fresh produce, artisanal goods, and a warm sense of community.

For families considering a move to Winter Garden, the area is served by the highly regarded West Orange High School. Known for its commitment to academic excellence and a wide range of extracurricular activities, this school is a cornerstone of the community and a significant draw for families looking to settle down in the area.

The real estate market in Winter Garden boasts a diverse range of homes, from charming historic houses to modern developments, ensuring there’s something for everyone. Whether you're seeking a cozy bungalow or a spacious family home, you’ll find properties that cater to your lifestyle and budget.

With its lush parks, scenic lakes, and a plethora of recreational opportunities, Winter Garden is not just a place to live; it’s a place to thrive. Experience the warm hospitality and vibrant community spirit that makes Winter Garden a truly special place to call home. Explore the possibilities today and discover your perfect slice of paradise in this enchanting Florida city!

Newest Winter Garden Homes with West Orange High High school

RARE corner 2.5-acre homesite in Winter Garden's sought-after Lake Avalon. No HOA and A-1 zoning that welcomes a custom estate, ADU, extra garage, barn, horses, or RV and boat storage. High and dry with gentle slope, mature trees, and a mix of cleared and wooded ground already prepped for plans and permitting, this 333-by-327-foot parcel offers real, usable space and strong frontage just minutes from Hamlin Town Center, Horizon West amenities, and Disney's back entrance. Enjoy country privacy without giving up convenience or top-rated schools. Utilities and survey are available; bring your own builder or partner with a local custom firm that knows the area. Corner, no-HOA acreage this close to the growth corridor is increasingly scarce - an opportunity to design the property you've been waiting for rather than settle for a typical subdivision lot.

17206 Red Bird Road, Winter Garden

3 Beds ⋅ 4 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code

Downtown Winter Garden becomes part of everyday life at this one-of-nine residence at 30 North Park, where a covered balcony overlooks the West Orange Trail and Plant Street’s dining, shops, and gathering spots are only a short stroll away. Arranged across three thoughtfully designed levels, the home balances connected gathering spaces with room to work and unwind. The main level brings the kitchen, dining area, and living room together beneath tall ceilings. An oversized island anchors the kitchen, complemented by quartz countertops, tall two-tone cabinetry, stainless steel appliances, and natural-gas cooking. Decorative wood beams, built-ins, and a gas fireplace feature wall give the living room character, while sliding glass doors extend the space to the balcony. Each of the three bedroom suites includes a walk-in closet and private full bathroom. Two suites occupy the upper level, including the primary with fitted closet storage, dual sinks, a glass-enclosed shower, and a separate water closet, while the second-level suite is currently arranged as a window-lined office. A ground-level bonus room with an adjoining fourth full bath creates another adaptable space for media, fitness, hobbies, or guests. Engineered hardwood and designer tile keep the interior carpet-free, while upper-level laundry, a tankless water heater, zoned HVAC, spray-foam ceiling insulation, and an attached rear-entry two-car garage add practical convenience. From quiet time on the balcony to mornings on the trail and evenings along Plant Street, this home pairs polished, flexible interiors with a distinctly downtown Winter Garden lifestyle.

72 N Park Avenue Unit 8, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully designed 4-bedroom, 3.5-bath home offering stylish upgrades and exceptional indoor-outdoor living in the charming Town of Oakland. From the inviting covered entry and brick-paver driveway to the bright, open interior, every space has been thoughtfully designed for comfortable everyday living and effortless entertaining. The impressive kitchen features abundant cabinetry, expansive countertops, stainless-steel appliances, a natural gas cooktop, built-in oven and microwave, subway-tile backsplash, and an oversized center island with generous seating. Fabulous pantry features custom shelving and refrigerator. The kitchen flows seamlessly into the spacious living area, highlighted by a dramatic floor-to-ceiling accent wall with a sleek electric fireplace and built-in cabinetry. The formal dining room offers soaring ceilings, abundant natural light, and an elegant statement fixture. The spacious first-floor primary suite provides a peaceful retreat with a tray ceiling and a luxurious ensuite bathroom featuring a large glass-enclosed shower, separate soaking tub, dual-sink vanity, huge walk-in closet and distinctive designer finishes. Upstairs, you will find three additional bedrooms and a versatile bonus room—perfect for a home office, media room, playroom, or additional gathering space. One of the upstairs bedrooms includes a private ensuite bathroom, providing an ideal arrangement for guests. Sliding glass doors open to a private, screened outdoor oasis featuring an extended brick-paver patio, covered dining space, multiple conversation areas, and a relaxing 8-person spa—perfect for enjoying Florida living throughout the year. A privacy fence enhances the peaceful backyard setting. Residents of Hull Island enjoy access to a community pool, dog park, playground, and picnic area. The neighborhood also offers convenient access to the Oakland Nature Preserve, 22-mile West Orange Trail, and downtown Oakland. Enjoy the town’s Thursday farmers market, Arts and Heritage Center, local coffee shop, and Speer Park, with vibrant downtown Winter Garden just minutes away. Conveniently located near major highways, theme parks, downtown Orlando, Orlando International Airport, restaurants, shopping, and hospitals, this exceptional Oakland home combines contemporary style, thoughtful design, and an outstanding Central Florida lifestyle. You're only an hours' drive to some of Florida's finest beaches. Schedule your private showing today!

1016 Catori Road, Oakland

4 Beds ⋅ 3 Baths ⋅ Oakland Parkb-3 SubDv. ⋅ 34787 Zip Code

A rare opportunity in highly sought-after Oakland Park—this beautifully furnished, turnkey home offers **4 spacious bedrooms, 3 full bathrooms, including a first-floor bedroom and full bath ideal for guests, extended family, or an in-law arrangement**, plus the exceptional Winter Garden lifestyle buyers are looking for. Tall ceilings, 8-foot doors, elegant architectural details, high-end décor, and thoughtfully designed living spaces create an elevated yet comfortable feel throughout. (If the buyer prefers not to keep the furniture and furnishings, they can be excluded from the sale.) The showpiece kitchen is truly the heart of the home, featuring premium quartz countertops, a 5-burner gas range, stainless steel hood, striking designer backsplash, and spacious walk-in pantry. The spa-inspired primary suite offers an expansive private bathroom and generous walk-in closet, creating the perfect retreat. And for a little extra personality, the home even has its very own “Harry Potter” closet! Enjoy Florida living from the inviting screened front porch, complete with a porch swing perfect for morning coffee, an afternoon book, or relaxing at the end of the day. The back patio and fenced yard provide another comfortable setting for entertaining, outdoor dining, or simply enjoying the beautiful Florida weather. An expansive 3-car garage offers exceptional space and storage. Offered fully furnished with beautiful, high-end furnishings and décor, this home is truly turnkey—just bring your suitcase and start enjoying the lifestyle. Located near highly regarded schools and just moments from the West Orange Trail, walk, bike, take your golf cart, or drive to charming Downtown Winter Garden, the Farmers Market, restaurants, shopping, and entertainment. Move in before the holidays and experience everything this incredible community has to offer, including festive neighborhood traditions and upcoming celebrations such as the golf cart parade, fall festival, and more. An exceptional opportunity to own a remarkably equipped home in one of the area’s most desirable communities at an amazing value.

226 Hammock Preserve Loop, Oakland

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

3 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

Welcome home to a place where life feels just a little easier. Tucked inside the peaceful Westbrook community of Winter Garden, this beautifully maintained, move in ready townhome offers the perfect blend of comfort, style, and convenience. Step inside to discover an inviting open living and dining space that naturally brings everyone together. The heart of the home is the kitchen, thoughtfully designed with gleaming granite countertops, stainless steel appliances, a contemporary tile backsplash, and plenty of space to prepare everything from quick weekday breakfasts to weekend gatherings with friends. Stylish upgraded lighting throughout adds a fresh, modern touch to every room. Upstairs, all three bedrooms create a private retreat away from the main living areas. The spacious primary suite is designed for relaxation and features dual walk in closets, giving everyone room to stay organized. With two additional bedrooms and two and a half bathrooms, there's plenty of flexibility for family, guests, or a dedicated home office. Behind the scenes, a newer high efficiency HVAC system with a UV germicidal light provides year round comfort and added peace of mind. Outside your front door, you'll love being just minutes from Winter Garden Village, the award winning shops and restaurants of Historic Downtown Winter Garden, and the excitement of Disney Springs. Easy access to SR 429 puts Orlando, Tampa, and Central Florida's top attractions within easy reach, making both your daily commute and weekend adventures effortless. Beautiful, meticulously cared for, and ideally located, this is more than a townhome. It's the beginning of your next chapter. Schedule your private showing today.

1017 Priory Circle, Winter Garden

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

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

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

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

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

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

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