Homes for Sale Near West Orange High in Winter Garden - 147 homes

Remarks: Welcome to 1209 Castleport Rd — your next chapter in Stoneybrooke West, a gorgeous golf-course community where everyday feels like a getaway. From the moment you arrive you’ll love the manicured fairways, peaceful walking paths, and neighborhood pride that make this community stand out. Step inside and imagine family mornings and movie nights in the bright, open living spaces. This home offers 5 spacious bedrooms and 3 full bathrooms — plenty of room for guests, a home office, or a hobby room. Thoughtful finishes and flexible room spaces make entertaining effortless and daily life comfortable. Location is everything: you’re minutes from theme parks, with fast highway connections for stress-free commutes and weekend escapes, plus easy access to shopping, dining, and services. Whether you’re teeing off on the greens, grabbing dinner nearby, or heading out for a day at the parks, 1209 Castleport Rd combines comfort, convenience, and that warm, community feel you’ve been looking for.

Listing is courtesy of: THE PROPERTY STOP LLC (407-744-5557)

Listing Agent: Angela Magac (407-744-5557)

Remarks: BOM. Buyer decided against stairs. There is a specific kind of silence that exists only within the gated sanctuary of Canopy Oaks. It is the sound of ancient oak leaves stirring in a gentle breeze & the distant, rhythmic splash of a stone fountain. Here, the recipient of the Parade of Homes Grand Award stands as a magnificent testament to what happens when timeless Italian architecture is reimagined for a modern lifestyle. This is not merely a residence. It is a legacy of vertical liberation, a home that breathes with you, scales with your ambitions, and cradles your quietest moments in an embrace of stone and iron. Your journey begins at the threshold of 8-foot, solid double-entry doors. As they swing open, the frantic pace of Central Florida fades, replaced by a two-story foyer that commands immediate respect. A hand forged iron staircase sweeps upward in a graceful arc, mirrored by the delicate charm of a Juliette balcony that suggests a life lived with a touch of Mediterranean flair. Every inch of this grand entrance is a curated experience, designed to transition you into a realm of meticulously crafted prestige where every shadow and light well has been considered. For those who view cooking as a performance art, the professional-grade kitchen is your stage. High-end Kitchen Aid appliances and a natural gas cooktop meet the warmth of artisanal design. The 42-inch upper cabinetry and a hidden walk-in pantry ensure the visual continuity remains unbroken. At the center sits a massive prep island with integrated beverage refrigeration, designed specifically for the art of hosting. Here, the boundary between chef & guest is delightfully blurred. Nearby, the home reveals its most enchanting secret, the drop-down wine cellar. Behind a hand-forged iron gate lies a space that transports you directly to a cobblestone alleyway in Tuscany. With label-forward shelving casting a museum-quality glow & a quaint bistro table within, it evokes the feeling of a private corner in a centuries-old Italian eatery. It is the ultimate setting for an evening pour, a space where time slows down & the modern world feels a thousand miles away. The first-floor owner’s suite is a masterclass in personal seclusion. By design, this space serves as a dedicated haven of quietude, featuring soaring tray ceilings & an atmosphere of total stillness. The spa-inspired bath, featuring a frameless glass walk-through shower & a free-standing soaking tub, offers a daily ritual of total restoration. As you ascend, the lifestyle shifts toward entertainment. The dedicated theater room stands ready for premiere nights, offering a dark, immersive escape. Adjacent, the versatile gathering room opens onto a private balcony overlooking the shimmering resort-style pool & the vast, permanent conservation area. With no rear neighbors, your view is an unbroken tapestry of natural beauty. The outdoor living area features a resort-style pool & spa framed by water/fire bowls & a rainfall pergola. With a full summer kitchen & a backyard that merges into conservation, your privacy is absolute. Enjoy the nightly glow of nearby fireworks from your peaceful terrace, surrounded by the scent of night-blooming jasmine. Strategically along the medical corridor, you are minutes from AdventHealth, Orlando Health & the soul of Winter Garden. Backed by a whole-house natural gas generator & water purification, this home offers security & beauty. Welcome home. Check out the video tour!

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)

Listing Agent: Sean Spencer (407-383-0707)

Remarks: Gorgeous pool home in Cypress Reserve featuring a private office, loft/game room, theater room, and over 4,100 sq ft with a 3-car garage. This stunning 4-bedroom, 3.5-bath residence offers thoughtfully designed living space that blends elegance, comfort, and functionality—delivering an exceptional lifestyle in one of Winter Garden’s most sought-after communities. From the moment you enter, soaring 20-foot ceilings, expansive windows, and an abundance of natural light greet you. A grand staircase and balcony create a striking focal point, anchoring the open-concept living area. The entry features formal living and dining spaces, along with a private office with French doors—ideal for working from home. At the heart of the home is a beautifully appointed gourmet kitchen, designed for both everyday living and entertaining. Highlights include a gas cooktop, built-in convection oven and microwave, pot filler, elegant backsplash, oversized center island, and extended cabinetry with ample storage—all overlooking the main living area and pool. The spacious primary suite is conveniently located on the main floor and features tray ceilings and a versatile sitting area—ideal for a secondary office, fitness space, or private retreat. The oversized custom walk-in closet is a standout, while the luxurious primary bath offers a large walk-in shower with a rain shower head, dual vanities, a soaking tub, and abundant cabinetry. Upstairs, you’ll find a generous loft, a dedicated media/theater room, and three additional bedrooms, including a Jack-and-Jill layout with walk-in closets. The flexible floor plan offers endless possibilities, with the loft or media room easily convertible into an additional bedroom. Step outside to your backyard retreat featuring a screened-in, heated saltwater pool with sun shelf, an expansive paver patio, and plenty of space for outdoor entertaining or relaxing in the Florida sunshine. With HOA green space behind the home, you’ll enjoy a more open feel and peaceful views. Additional highlights include 8-foot doors and high ceilings throughout, a tankless water heater, a spacious laundry room with utility sink and storage, oversized under-stair storage, and beautiful curb appeal with low-maintenance landscaping. Ideally located within walking distance to highly rated SunRidge Elementary and Middle School, and just minutes from downtown Winter Garden, Winter Garden Village, SR 429, Florida’s Turnpike, I-4, Downtown Orlando, Orlando International Airport, and nearby attractions including Walt Disney World. Outdoor enthusiasts will love the proximity to the West Orange Trail and Tucker Ranch Recreation and Nature Complex, offering over 300 acres of scenic trails, green space, and outdoor recreation. Residents of Cypress Reserve also enjoy a community pool and playground with a low HOA. This exceptional home truly has it all—luxury, space, versatility, and an unbeatable location. Schedule your private showing today!

Listing is courtesy of: INFINITY REALTY GROUP LLC (407-234-2256)

Listing Agent: Deb Schroeder (407-234-2256)

Remarks: Welcome to beautiful Winter Garden. Check out this exceptional 5-bedroom, 3-bathroom home is located in a gated community that blends comfort with a friendly neighborhood atmosphere. Thoughtfully designed, the home features four bedrooms upstairs and a flexible downstairs bedroom ideal for guests or a home office. The spacious primary suite serves as a private escape, complete with a soaking tub, separate shower, and ample room to relax. Upstairs, two expansive loft areas provide endless possibilities—perfect for a home gym, media room, play space, or additional living area. The main level boasts formal living and dining rooms, along with a large family room that opens through sliding doors to a private pool retreat with two paved seating areas, ideal for entertaining or unwinding. An open floor plan, elegant dual-entry wooden staircase, and stainless steel appliances add to the home’s appeal. Offering generous space, charming details, and a peaceful yet convenient location, this home captures the best of Florida living—schedule your showing before it’s gone.

Listing is courtesy of: HP GLOBAL REALTY LLC (407-925-6780)

Listing Agent: Heron Patel (407-925-6780)

Remarks: Enchanting newly built home in Avalon Ridge with a private pool, located in one of the most desirable areas of Winter Garden. This beautiful residence has been thoughtfully designed and features 4 bedrooms with carpet flooring, 3 full bathrooms, and a perfect blend of modern space, functionality, and elegant finishes. The living area features sliding glass doors that open to the outdoor space and private pool, creating the perfect setting for entertainment and relaxation. The spacious living room flows seamlessly into a large kitchen equipped with modern cabinetry, stainless steel appliances, elegant countertops, and a generous center island. The primary suite offers a spacious bathroom with dual sinks, a large walk-in closet, and a comfortable walk-in shower. The three additional bedrooms provide plenty of space for family members or guests. The three-car garage offers ample room for vehicles, storage, or even a workspace. Ideally located in a rapidly growing area, just minutes from major highways, shopping centers, restaurants, and top-rated schools. Don't miss this opportunity—schedule your showing today!

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Jennifer Olmeda (407-547-9242)

Remarks: PRIME Winter Garden location off Hardwood Marsh and Avalon! It’s not often a home hugs you when you walk through the door, the hint of warmth through the window and the enveloping feeling of home. A true place of stillness that is so hard to find nowadays. The Hawthorne model is really the perfect floor plan! With space for everyone still managing to embody an inviting coziness with over 3,500 sq ft of living space for you, your family…an unexpected guest! A quaint entry with 2 areas for an office, formal living opens up to a 2-story ceiling in the family room with adjacent kitchen! A large island has seating and room for a full size dining table in the breakfast nook! An abundance of windows and sliding glass doors reveal a lovely view of the tropical foliage. Enjoy cooking while watching movies keeping everyone together! The thoughtful design gives ample prep space and tons of cabinet storage! This perfect entertaining area spills into the oversized screened lanai that can be enjoyed year round with an array of fruit trees and a natural privacy from the mature landscape. The primary suite is on the first floor ensuring you can enjoy this home even into your golden years! A relaxing escape with back yard views, ensuite bath with large soaking tub, shower, dual vanities and 2 walk-in closets! Again, storage is not an issue in this home! On the second floor, stairs lead to a huge loft/bonus room that peers over the family room with a half wall that aids in noise reduction. Want a more open feel? Check out Etsy’s decorative railings to personalize your loft! Built-in character ensures many creative ways to utilize the space! This upstairs is “cart wheel” worthy and the options are endless! The bedrooms are spread apart giving every occupant their own area! A centrally located study/art nook even has an opening to the downstairs so you never miss the words "dinner's ready"! This fantastic layout allows you to fulfill your every wish for not only a beautiful, but organized space! No more trying to make things work, because it all fits! They say #1 rule in buying real estate is LOCATION & this community of well manicured lawns ensures your biggest investment is a good one! You can still find that hometown feel you see in movies, with the weekly Farmer's Market in Historic Downtown, soccer and baseball fields bustling on Saturday mornings! Monthly and seasonal events are also abundant and so fun! Pop over to Epic or Disney for the afternoon or enjoy delicacies from around the world at Epcot! All just a short drive from home! The house across the street recently sold for 870k!

Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)

Listing Agent: Autumn Makin (352-455-0044)

Remarks: Presenting this exquisite modern residence standing alone without neighbors in either side or rear in a neighborhood of almost 150 homes showcasing souring ceilings, designer finishes, and an open-concept living space bathed in natural light. A gourmet kitchen that anchors the home, while expansive glass doors reveal a resort-style screened pool and outdoor lounge. Architecture, luxurious details inside all bathrooms and kitchen, and seamless indoor-outdoor living create an exceptional retreat for refined entertaining. An amazingly fancy electric chimney gives the living room area warmth and elegance. AC units are of high efficiency with hotel fragrance throughout the entire home. COME AND SEE IT SOON! AC units is 3 years. New roof to be installed.

Listing is courtesy of: PAULINO GLOBAL REAL ESTATE (407-455-1981)

Listing Agent: Andrea Paulino (813-753-6110)