Winter Garden Single Family Homes For Sale - 564 homes

Remarks: There is a specific frequency to life in Oakland Park that exists nowhere else in Central Florida. It is a rare, rhythmic harmony between the nostalgia of Old Florida and the crisp, clean lines of modern luxury. As you cross into the community, the atmosphere shifts. The air feels lighter, filtered through the canopy of ancient oaks and manicured greenery of a village designed for connection. This is not just a residential development. It is an intentional ecosystem where the 22-mile West Orange Trail serves as the community’s main artery, pumping vitality into every cul-de-sac and alleyway. At 931 Kylee Alley, this lifestyle reaches its peak. On a commanding corner lot, the David Weekley Stoneybrook residence stands as a testament to timeless architecture. One of the greatest luxuries of this exterior is what you do not have to do. In Oakland Park, your time is reclaimed. The homeowners association provides comprehensive landscaping maintenance and care, ensuring your estate remains in a perpetual state of magazine-ready perfection. Imagine the freedom of a Saturday morning where the scent of freshly cut grass is a sensory delight rather than a chore on a list. Going across the threshold, you are greeted by a masterclass in sightlines. Built in 2022, the home possesses a groundedness that only thoughtful design can provide. The soaring ceilings act as a canvas for the Florida sun, which pours through windows dressed in custom plantation shutters. The heart of the home is the gourmet kitchen. The oversized central island is topped with solid-surface counters that feel like cool silk to the touch. It serves as the natural gathering point for evening wine tastings or slow Sunday brunches. The floor plan is a brilliant response to the modern need for connection and solitude. On the main floor, the layout offers a sophisticated executive wing feel. Whether you utilize the first-floor bedroom as a guest en-suite or a high-powered home office, the separation of space ensures privacy. Ascending to the second level, you enter the private quarters. The primary owner’s retreat is a voluminous space anchored by a spa-inspired en suite where stresses of the day dissolve. Life here is defined by proximity to the West Orange Trail. This is your private gateway to the best of Winter Garden. Within minutes, you can cycle toward the historic charm of Plant Street or explore the renowned Saturday Farmers Market. Back within the gates, the amenities rival those of a five-star resort. Three sparkling swimming pools, a social clubhouse, and a dog park ensure every member of the family enjoys a sense of belonging. This is a lock-and-leave lifestyle in its purest form. The Investment Thesis. From an investment perspective, 931 Kylee Alley represents a blue-chip asset. Oakland Park is recognized as one of the stable and appreciating communities in the region. As Winter Garden evolves into a premier luxury destination, the scarcity of newer construction on premium corner lots creates a natural ceiling for appreciation. This is a strategic land-hold in a community where demand consistently outpaces supply. Check out the virtual tour video!

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

Listing Agent: Barbara Vance Pa (407-947-6236)

Remarks: Gorgeous Brand new 4-bedroom 3.5 bath home across the street from the pool and fitness center, Off Western Way on the west side of Disney. This home has a covered and paved front porch with direct views across the street to the community clubhouse, fitness center, pool and open park. When you want a little more privacy, you can sneak off to the small side covered patio. As you enter into the home, you are greeted by a wide foyer which opens to the main Great room, the stairs, and the first-floor spare 4th bedroom with full private bath. Walk past the partially open staircase with beautiful iron Rail, into the main Great room featuring Family, dining and kitchen. The family room is very large, over 18x16 feet and has a great storage closet under the stairs. The dining room has a window and large slider to the side covered patio and is completely open to the kitchen. The amazing Kitchen has tons of cabinets, counter space, huge pantry, Large flat island with Stone counter bar top, cabinet crowns, all SS appliances and Gas stove. Just past the kitchen is the half bath powder room and drop zone from when you enter into from the rear facing garage. First floor is tile throughout except for bedroom. Upstairs has carpet in all bedrooms and open loft. The Master Bedroom has 2 very large walk-in closets, and nice large bath with two separate vanities with extra cabinet space, a walk-in shower, and private toilet. The Master has more privacy split away from the other bedrooms by the laundry room. Laundry room has extra space for an ironing board, and laundry sink next to the provided washer and dryer. Bedrooms 2, 3 are separated by a full bath with double sinks and shower/tub. Tankless water heater saves in efficiency and constant hot water. This home is in a great and quite community just a few miles off the 429 west of Disney. While this home sits across from the clubhouse and pool area, the community offers other areas of interest to explore and enjoy. A short block away has a fenced dog park and a walking trail around a long pond with Activities such as Corn hole, Bocce Ball courts, and picnic tables. Further inside the community has more open park areas with trails by scenic ponds currently under construction along with the back park which the playground should soon be built. Just a few miles off the major interchange of 429 and Western, just outside Disney West provides fast and easy access anywhere. Hospitals, restaurants and shopping are all close and many more are being built nearby. The builder states; Water Spring Elementary, Bridgewater Middle, and Windermere Highschool.

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

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

Remarks: Set within one of Winter Garden’s most loved communities, this thoughtfully designed two-story home offers a lifestyle shaped by ease, connection, and everyday enjoyment in Winter Garden, Florida. Morning walks along sidewalks, friendly neighbors, nearby parks, and resort-style amenities create a rhythm that feels relaxed yet vibrant. With top-rated schools, convenient access to shopping and dining, and Walt Disney World Resort just minutes away, the location blends Central Florida convenience with the feeling of being tucked into something special. From the moment you step inside, the home invites you to slow down and take it all in. Natural light fills the space, drawing your eye through the open living area to peaceful pond views and the private pool. Beyond the pond, a wooded area owned by Disney provides a protected natural backdrop that will never be built on, preserving privacy and tranquility. Oversized white tile spans the first floor, creating an open, airy atmosphere that feels clean and welcoming. At the center of the home, the kitchen is designed for real life and real gatherings. White cabinetry, granite countertops, a double oven, and a statement range hood anchor a space that works effortlessly for weeknight dinners or hosting friends. A large walk-in pantry keeps everything organized and within reach. Just beyond, the family room feels warm and grounded, with a stone accent wall, electric fireplace, and custom shelving creating a comfortable place to relax. The first floor offers flexibility to suit your lifestyle. A dedicated den or home office provides a quiet place to focus, while a formal dining room invites shared meals and conversation. A drop zone near the garage keeps daily routines running smoothly. Toward the back of the home, a spacious downstairs bedroom with a full en suite bath offers privacy, ideal for guests or multi-generational living. Upstairs, an open loft serves as a central gathering space for movie nights or game days, enhanced by a stone wall and theater-style seating. The owner’s suite feels like a true retreat with a tray ceiling, spa-inspired bath featuring a rain shower, dual sinks, generous storage, and two oversized walk-in closets. A private balcony overlooks the pond and wooded preserve, offering a peaceful place to enjoy morning coffee or unwind. Three additional upstairs bedrooms provide ample space for family or guests. Two share a hall bath, while one enjoys its own en suite for added comfort and privacy. Outside, the backyard feels like a private Central Florida escape. A resort-style saltwater pool with a lounging platform and in-water loungers overlooks the serene pond, creating an inviting setting for relaxing afternoons or entertaining. The screened enclosure allows for year-round enjoyment, and the community dog park directly across the street adds everyday convenience for pet lovers. With fresh interior paint and plantation shutters throughout, this move-in ready single-family home is ready for its next chapter. Community amenities include a resort-style pool, oversized cabana, sports fields, playground, sidewalks, and a dog park. This is more than a house — it is a place to settle in, build memories, and truly feel at home in Winter Garden.

Listing is courtesy of: REAL ESTATE HOUSE FL INC (407-484-0005)

Listing Agent: Gretchen Carlson (407-484-0005)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGES !!!! The Berkley at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Berkley model. This impressive 2,102 sq. ft. residence features 4 bedrooms, 3 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 15' great room flows seamlessly into the gourmet kitchen and dining area. The kitchen is a chef's dream, anchored by a massive center island and a walk-in pantry. A rare and highly desirable feature is the first-floor bedroom with walk-in closet—perfect for visitors or a quiet home office. The primary Owner’s Suite offers a spa-like experience with a generous walk-in closet and luxurious bath. Hamlin Meadows is the newest jewel of Horizon West, offering a diverse mix of rear-load homes in a highly sought-after Winter Garden location. Enjoy being minutes away from the vibrant Hamlin Town Center and major expressways.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Under contract-accepting backup offers. Experience refined Florida living in this exceptional 7-BEDROOM POOL HOME located in the prestigious West Lake Hancock Estates, perfectly positioned on an OVERSIZED CORNER LOT. The light-filled interior showcases a modern, open-concept floor plan with expansive living and gathering spaces ideal for both everyday comfort and elevated entertaining. At the heart of the home is the gourmet DOUBLE-ISLAND kitchen, offering generous prep space, abundant cabinetry, and a layout designed to host with ease. A rare and highly desirable feature, this home offers TWO PRIMARY SUITES on the FIRST FLOOR, each complete with private en-suite bathrooms and spacious walk-in closets, providing exceptional flexibility for multi-generational living, extended guests, or a private home retreat. The additional bedrooms are generously sized and thoughtfully placed, offering versatility for guest accommodations, a home office, fitness room, or creative space. Step outside to your private backyard oasis, where a sparkling POOL and OUTDOOR KITCHEN create the ultimate setting for relaxing, entertaining, and enjoying Florida’s year-round sunshine. Whether hosting summer gatherings or quiet evenings at home, this outdoor space is designed for elevated living. Additional highlights include a 3-car attached garage, ample storage throughout, and a pet-friendly neighborhood. Residents of West Lake Hancock Estates enjoy access to resort-style amenities, including a stunning clubhouse overlooking Lake Hancock, community pool, fitness center, playground, amphitheater, scenic walking and biking trails, canoe access, and a full calendar of organized social activities. Ideally located just off SR-429, this home offers convenient access to downtown Orlando, major highways, shopping, dining, and entertainment—while still providing the tranquility of an upscale, lake-centered community.

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

Listing Agent: Jason Asa (407-337-7702)

Remarks: Under Construction. What's Special: Game Room | Dedicated Study | Covered Lanai | North Facing Lot. New Construction - August Completion! Built by America's Most Trusted Home Builder. Welcome to the Ashwood at 14788 Field Daisy Drive in Harvest at Ovation! This welcoming new home blends spacious living with thoughtful design, featuring a bright great room that flows seamlessly into a beautifully appointed kitchen with quartz countertops and designer kitchen cabinets. Luxury vinyl plank flooring runs throughout the main living area, creating a warm and cohesive feel that is easy to enjoy every day. Just off the kitchen, the lanai extends your living space outdoors, while a versatile flex room and convenient powder room sit near the foyer. Upstairs, the primary suite offers a comfortable retreat with an en-suite bath and a large walk-in closet, alongside two secondary bedrooms that share a full bathroom and an upstairs laundry room. The rear two-car detached garage includes stairs leading to a spacious game room complete with a wet bar, full bathroom, and walk-in closet, giving you even more room to live and entertain. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: Bedroom in place of loft, game room, wet bar at game room, full bathroom at game room, 8' interior doors, oak treads and painted risers. Photos are for representative purposes only. MLS#O6398754

Listing is courtesy of: TAYLOR MORRISON REALTY OF FLORIDA INC (407-756-5025)

Listing Agent: Michelle Campbell (407-756-5025)

Remarks: Stunning Corner Lot Home Welcome to this beautifully designed, home situated on a desirable corner lot in the sought-after Highland Ridge community in Winter Garden, FL. Built by Meritage Homes, this residence offers the perfect blend of modern style, comfort, and energy efficiency. The open-concept first floor features a spacious great room and dining area that flow seamlessly together, creating an ideal space for entertaining and everyday living. The gourmet kitchen is the heart of the home, complete with a large island overlooking the main living areas and patio—perfect for gatherings with family and friends. Upstairs, the private primary suite offers a relaxing retreat with an oversized walk-in closet, dual vanities, and a sleek walk-in shower. Thoughtfully designed throughout, the home showcases professionally curated finishes, including elegant granite or quartz countertops and stylish tile flooring. Additional highlights include a detached two-car garage, ample natural light, and smart, energy-efficient features designed to provide long-term savings, improved comfort, and healthier living. Located in a vibrant community with top-rated schools and convenient access to major employment centers, shopping, and dining, this home truly offers the best of modern Florida living. Furnishings may be negotiable, offering a convenient, move-in-ready opportunity for buyers.

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

Listing Agent: Vinny Apolinario (407-371-2227)

Remarks: Under contract-accepting backup offers. Nestled in the heart of Winter Garden’s beloved Golf Cart District, this oversized Seaside model by David Weekley invites you to embrace a lifestyle where luxury meets charm. Tucked within the picturesque Oakland Park Subdivision, this home offers not just a place to live but a way to experience the very best of this vibrant community. Step inside, and you’re greeted by the golden warmth of light wood laminate floors and streams of natural light pouring through every window. The gourmet kitchen, truly the soul of the home, is a chef’s haven with a gas stovetop, sleek finishes, and plenty of room to gather, cook, and connect. Just steps away, the main-floor master retreat becomes your personal sanctuary—offering peace, privacy, and every comfort you could wish for. The second floor is a haven in its own right, with three spacious bedrooms circling a versatile loft space. Whether it becomes a playroom, a cozy reading nook, or your dream work-from-home setup, the possibilities are endless. Outside, the rare 3-car garage, discreetly accessed via a quiet alley, adds both convenience and a touch of exclusivity. But the magic doesn’t stop at your doorstep. Imagine mornings strolling leafy trails, afternoons exploring Winter Garden's historic downtown, and evenings savoring craft beer or artisan treats at the nearby Plant Street Market—a true local gem just moments away. From farmers markets to boutique shops, this is a neighborhood where every day feels like a celebration. This isn’t just a home; it’s a gateway to the lifestyle you’ve been dreaming of. Don’t wait—schedule your private tour today and let this storybook setting become your reality.

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

Listing Agent: Matthew Mckee (407-948-0658)

Remarks: Welcome to this stunning corner-lot residence located within the exclusive Osprey Ranch community in Winter Garden, just minutes from Walt Disney World and surrounded by fine dining, premium shopping, upscale hotels, and top-rated schools. This beautifully appointed home offers 2,420 sqft of refined living space, featuring 4 spacious bedrooms and 3 full bathrooms, thoughtfully curated to deliver both comfort and sophistication. A standout feature of this residence is the first-floor bedroom with a full bathroom, ideal for multigenerational living, guests seeking privacy, or a flexible office space. Designed for a seamless indoor-outdoor lifestyle, this home showcases: • A fully private fenced backyard, offering both security and tranquility • Custom-designed window treatments, adding a refined designer touch • Expansive bedrooms filled with natural light and generous proportions • A charming private courtyard, perfect for outdoor dining, BBQs, and entertaining Positioned on a premium corner lot, this residence offers enhanced privacy, abundant natural light, and a distinguished presence within the community. Located within a top-rated school district and in one of Central Florida’s most desirable growth corridors, this property seamlessly blends luxury, functionality, and long-term value. An exceptional residence that blends sophistication, comfort, and an elevated way of living.

Listing is courtesy of: A & V FLORIDA REALTY GROUP LLC (786-641-7923)

Listing Agent: Edgar Brito (786-641-7923)

Remarks: Under contract-accepting backup offers. Welcome to refined Florida living in this pristine Lennar Executive Collection sprawling ranch home, ideally situated on an oversized, fully fenced home site, in the highly sought-after Summerlake community of Horizon West. Offering over 2,300 square feet of thoughtfully designed OPEN floorplan living, this four-bedroom, 2.5-bath residence with a three car garage(2 tandem with professionally installed overhead storage) has been used exclusively by the owners as their second home for vacation (never rented out) and feels nearly new, with several appliances never even used. At the heart of the home, the chef-inspired kitchen showcases a GAS RANGE, stainless steel appliances, granite countertops, a generous island with abundant seating, a walk-in pantry, and a dedicated dining area that easily accommodates both casual and formal dining.  Glass sliders open to the screened lanai, extending the living space outdoors and overlooking the oversized backyard with ample room to design a resort-style pool, outdoor kitchen, and/or a private oasis tailored to your vision. The kitchen flows seamlessly into the expansive great room, creating an ideal setting for entertaining and everyday living. Privately tucked away, the Primary Suite offers a serene retreat complete with crown molding, an en-suite bathroom with dual vanities showcasing granite countertops, a soaking tub, separate oversized walk-in shower, and a custom-designed boutique-style closet that enhances both elegance and organization. The light-filled split-bedroom floor plan features tile and luxury vinyl plank flooring throughout, creating a completely carpet-free interior with a clean, modern aesthetic. Three spacious secondary bedrooms and a full bath are privately positioned toward the front of the home. There is also a laundry room with a drop zone located off the garage entry.  Additional upgrades include a tankless water heater, water softener, newer A/C system, a wired security system that is also wired for outdoor cameras , crown molding throughout the primary living area, and an in-wall pest system.  Low HOA’s that includes but is not limited to lawn care, bush trimming, and mulch application allows for low-maintenance living.  Residents of Summerlake enjoy resort-style amenities including a community pool, clubhouse for social events, fitness center, basketball, tennis/pickleball courts, dog park, playgrounds, zip line ,walking paths, multiple ponds ,fishing dock, all conveniently located near shopping, dining, major highways and world renowned theme parks. You can enjoy Disney fireworks from the community viewing areas.  Also, the golfer in you will be happy to know that you are only a short drive away from the Orange County National Golf Course. This exceptional home offers the perfect blend of comfort, elegance, and lifestyle convenience in one of Horizon West’s most desirable communities. Summerlake,Hamlin and Horizon schools were all A rated for the 2024/2025 school year!! SEE DRONE TOUR OF INTERIOR , click on Tour#1

Listing is courtesy of: UPSIDE REAL ESTATE INC (407-308-5750)

Listing Agent: Ann Wargo (407-616-3041)

Remarks: Welcome to 14058 Frasier Street in the heart of Winter Garden, Florida—where modern comfort meets small-town charm! Located in one of Central Florida’s most sought-after communities, this beautifully maintained home offers the perfect blend of style, space, and convenience. Step inside to discover an inviting open-concept floor plan filled with natural light, high ceilings, and thoughtfully designed living spaces ideal for both everyday living and entertaining. The spacious kitchen serves as the centerpiece of the home, featuring ample cabinetry, generous counter space, and a seamless flow into the dining and living areas—perfect for hosting family and friends. The primary suite provides a private retreat with a well-appointed en-suite bath and generous closet space. Additional bedrooms are comfortably sized and versatile, ideal for guests, a home office, or a growing family. Every detail has been carefully maintained to create a move-in-ready opportunity. Enjoy Florida living year-round with a private backyard space perfect for relaxing evenings, weekend barbecues, or creating your own outdoor oasis. Whether you envision a garden, play area, or custom patio retreat, the possibilities are endless. If you’re looking for a home that offers comfort, location, and lifestyle all in one—14058 Frasier Street is ready to welcome you home. Schedule your private showing today!

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

Listing Agent: Ali Partovi (386-295-5115)

Remarks: Under contract-accepting backup offers. Winter Garden’s finest — a spacious 4-bedroom, 3.5-bathroom home with a 3-car garage, pool, outdoor kitchen, and breathtaking pond views. This exceptional home is filled with custom upgrades throughout, including custom beams, a striking stone entry wall, built-in dining seating, an expanded drop zone with additional cabinetry, and a custom bar area complete with a wine refrigerator. The gourmet kitchen features 42-inch white cabinets, stainless steel appliances, a large farmhouse sink, and an oversized pantry/storage area. A first-floor den/office offers the perfect flex space for work or relaxation. Upstairs, the primary suite is a true retreat with a custom-designed bath, wood-trimmed tray ceiling, private balcony overlooking the pond, and custom built-ins in the walk-in closet. The adjacent bedroom has been transformed into a dream walk-in closet with shoe storage and a lighted vanity, but can easily be converted back into a bedroom upon request. Two additional bedrooms complete the second floor, including one with its own private ensuite, while the open loft with custom beams creates the perfect setting for a cozy movie night. A second-floor laundry room adds everyday convenience. Step outside into your private resort-style oasis, featuring stunning pond views, a tongue-and-groove stained ceiling, built-in seating, and a fully equipped outdoor kitchen with sink, grill, pizza oven, refrigerator, and stainless hood. The heated UV-filtered pool, connected to the home’s water softener system, is enhanced by a beautiful stone waterfall. A sauna and cold plunge complete this extraordinary outdoor retreat — truly an at-home resort experience. Lush landscaping surrounds the patio and pool area, creating a tropical and private escape, complemented by thoughtfully added rock garden beds and light paver stone walkways along the side of the home that enhance both beauty and functionality. Beyond the pond, a wooded area owned by Disney provides a protected natural backdrop that will never be developed, preserving both privacy and tranquility. The 3-car garage is equally impressive with custom built-ins, overhead storage racks, and a metallic epoxy floor. New exterior painting is currently in progress. Life here extends beyond the home. Morning walks along tree-lined sidewalks, friendly neighbors, nearby parks, and resort-style community amenities create a rhythm that feels both relaxed and vibrant. Residents enjoy access to a resort-style pool, oversized cabana, sports fields, playground, sidewalks, and two dog parks. Located in an area known for top-rated schools, with convenient access to shopping and dining, and just minutes from Walt Disney World Resort, this home perfectly blends Central Florida convenience with the feeling of being tucked into something truly special. More than a house — this is a place to settle in, build memories, and truly feel at home in Winter Garden.

Listing is courtesy of: REAL ESTATE HOUSE FL INC (407-484-0005)

Listing Agent: Gretchen Carlson (407-484-0005)

Remarks: Stunning home located in the highly desirable Winter Garden area, offering a modern and spacious floor plan designed for comfortable living and entertaining. This beautifully maintained property features bright open living spaces, a stylish kitchen with ample cabinetry, and generously sized bedrooms. Enjoy a private outdoor area perfect for relaxing or hosting gatherings. Conveniently located near top-rated schools, shopping, dining, major highways, and just minutes from Downtown Winter Garden, Hamlin Town Center, and Disney attractions. An exceptional opportunity to enjoy luxury, location, and lifestyle in one of Central Florida’s most sought-after communities.

Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)

Listing Agent: Samir Naim (818-268-9917)

Remarks: **New landscaping in progress with pictures to follow, expected by April month end** Welcome to Waterleigh Phase 1 in Horizon West, Winter Garden, one of the most desirable communities in the area, known for resort-style amenities, scenic lakes, and top-rated schools. This rare one-story Arbor floor plan offers an open-concept layout with a highly sought after private fenced backyard - perfect for relaxing, entertaining, and enjoying Florida living at its best. This home features an extended screened-in lanai & patio upgrade, private backyard with a hot tub, cozy electric fireplace, dedicated home gym space, tandem 3-car garage, fresh exterior and interior paint. This home is move-in ready with thoughtful upgrades. Minutes from Hamlin Town Center, shopping, dining, and entertainment, plus quick access to Disney and major highways. Please schedule a showing to come view this rare opportunity to own a single-story home in Waterleigh Phase 1.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Timothy Shepard (727-204-9618)

Remarks: **** HEART OF DOWTOWN WINTER GARDEN **** CAN'T GET MUCH CLOSER TO ***HISTORIC DOWNTOWN WINTER GARDEN *** THAN THIS! SERIOUSLY! FRESH OWNER REDO WITH DISCERNING DESIGN CHOICES ON THIS SOLID & ADORABLE 3 BEDROOM/2 BATH FENCED YARD (SOLID CONCRETE BLOCK) CHARMER. *** NO HOA OR FEES*** HOOOORAY! & WITHIN STEPS TO DOWNTOWN PLANT STREET, TONY'S, HARLOW GROVE RESTAURANT, CHURCHES, FARMERS MARKET, CROOKED CAN FOOD HALL, JESSIE BROCK COMMUNITY PARK, PUBLIC BOAT RAMP AT NEWTON PARK, AND ALL THAT FAST GROWING DOWNTOWN HISTORIC WINTER GARDEN HAS TO OFFER!!! AMAZING CHANGES ARE ON THE HORIZON!!!----GET IN ON YOUR OWN LOCKED IN LOCATION NOW!!!----- (LOCATED WITHIN THE ZONED GOLF CART DISTRICT). WITHIN MINUTES TO HWY 50, FOWLER GROVES/LOWES/TARGET & 429 FREEWAY ENTRANCE, AS WELL AS FLORIDA TURNPIKE AND E-W EXPRESSWAY ENTRANCES BEING MERE MINUTES AWAY ON EAST PLANT STREET; OH SO CENTRALLY LOCATED DIRECTLY IN "TOWN PROPER" JUST A FEW LOTS UP FROM PLANT STREET; & JUST A LITTLE FURTHER DOWN MAIN STREET AND YOU ARE AT THE PUBLIC BOAT RAMP, NEWTON PARK AND THE FARNSWORTH CITY POOL!!! BEYOND EXCELLENT ACCESS TO MULTIPLE GROCERIES, TAILORS & SHOPPING OPTIONS AT HWY 50, PARK AVENUE, DILLARD STREET AND NEARBY OAKLAND! ALSO, THE WEST ORANGE TRAIL RUNS PERPENDICULAR TO MAIN STREET (YOUR STREET) & IS STEPS FROM YOUR HOME-----CONCRETE BLOCK CONSTRUCTION BUILT W/TERMITE BOND/MONTHLY PEST TREATMENT-ALL WITH MASSEY SENTRICON & TRANSFERABLE BOND TO THE NEW OWNER--- HOME HAS GROOMED MATURE OAKS WITH FENCED IN BACK YARD (WOOD PLANK AND VINYL) WITH ELEVATED WOOD DECK FOR FLIPPING OPEN THE BRAND NEW DOUBLE FRENCH DOORS AND ENJOYING FOR ENTERTAINING!!! ***EXCELLENT VALUE/EXCELLENT LOCATION/GOLF CART DISTRICT/NO HOA!***--WHY RENT WHEN YOU CAN (OWN) YOUR OWN PROPERTY FOR JUST A FEW BUCKS MORE PER MONTH? -----HOME WARRANTY OPTIONS AVAILABLE. WITHIN ZILLOW RANGE PRICING! GREAT DEAL. COME SEE FOR YOURSELF...........

Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)

Listing Agent: Jason Fulmer (321-303-6670)

Remarks: Under Construction. This stunning Plant II single-family home is located in the desirable Northlake at Ovation community. This popular one-story, open-concept layout features 4 bedrooms and 3 bathrooms, ideal for modern living. With finishes from the AW Collection Sapphire vibrant blues meet bright whites for a bold look. Enjoy a chef-inspired kitchen with 42" cabinets, quartz countertops, and large island overlooking the living and dining areas, perfect for entertaining. The home also includes luxury vinyl flooring, a private primary suite with walk-in closet, a covered lanai for outdoor living, and a spacious 2-car garage. Conveniently located in Winter Garden near shopping, dining, major roadways, and top-rated schools. Community amenities include pool, clubhouse, playground areas and dog park.

Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)

Listing Agent: Reed Williams (813-918-4491)

Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.

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

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

Remarks: Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion July 2026. Single family Bungalow. This home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a master suite is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet.

Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)

Listing Agent: Devahn Powell (571-234-7236)

Remarks: Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2 cars garage. The master bedroom is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet.

Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)

Listing Agent: Dayene Grubert (863-521-4474)

Remarks: One or more photo(s) has been virtually staged. Welcome to 15558 Sandfield Loop, a refreshed residence offering a turn-key lifestyle within one of Winter Garden’s most exclusive and hard-to-find GATED community. This house has been freshly updated from top to bottom, including new interior and exterior paint that makes the whole place feel brand new. The first thing you'll notice when you walk in is the massive, two-story high ceiling in the living area—it brings in tons of natural light and gives the home a great, airy feel. The kitchen has been fully redone with modern two-tone cabinets and beautiful quartz countertops. Throughout the home, you will find fresh paint and new flooring that perfectly complement the contemporary aesthetic. Situated within a highly-rated school zone, this MOVE IN READY property combines the security of a premier gated community with grand architectural features and stylish updates.

Listing is courtesy of: ORLANDO HIGHLAND REALTY LLC (561-385-7610)

Listing Agent: Xiaoli Lin (561-385-7610)