Homes for Sale Near West Orange High in Winter Garden - 120 homes

Remarks: Expansive and Inviting! Welcome home to 14790 Tullamore Loop. Location says it all! Convenient to restaurants, shopping, highways, theme parks, and more, this gated community remains one of the most popular communities in the area. This family-oriented neighborhood with a community pool is sure to please. With an oversized lot and plenty of room to roam, the open floor plan of this 4-bedroom / 2.5-bath home awaits to impress. Large formal living and formal dining rooms are the perfect venue for family gatherings. An elegant, open kitchen, overlooking the dinette into the family room, offers granite counters, 42” cabinets, double built-in ovens, a large breakfast bar, and a huge walk-in pantry allowing space for everyone to help the cook. When the day is done, retire to the oversized second-floor primary suite, which offers a spacious bath with a double-sink vanity, shower, garden tub, and a walk-in closet, completing this special and intimate space. Anchoring 3 large secondary bedrooms, this home beckons to an active family, offering the space you need. Enjoy your morning coffee or an evening barbecue, while enjoying the peace of your private pool, a HUGE private backyard! Complete with fruit trees (recovering from the freeze), including mango, sugar apple, sapodilla, guava, loquat, pear, jackfruit, fig, lemon, orange, neem, and banana, gives an instant farm-to-table experience. While certainly offering plenty of space for everyone to claim their own piece of paradise, you’ll find peace of mind that your investment is in a location that can’t be beat! Highlights include: Roof replaced in 2020. AC replaced in 2018. Appliances replaced in 2022. All blinds replaced 2022. Whole Home water filtration and softener system. Be sure to click the link for an interactive 3D Virtual Tour and floor plan!

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Rita Phillips (407-928-0573)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Significant Price Improvement! This spacious residence offers refined finishes and a thoughtfully designed layout, beginning with elegant porcelain tile in the main living areas and luxury vinyl plank flooring in all bedrooms and throughout the upper level. The chef-inspired kitchen serves as the heart of the home, featuring granite and quartz countertops, abundant cabinetry, and a generous walk-in pantry for exceptional storage and functionality. A versatile flex room on the main floor, accented with French doors, provides the ideal space for a guest suite, home office, or private den. The secluded owner’s retreat is a true sanctuary with a split-bedroom layout, expansive walk-in closet, dual granite vanities, and a relaxing garden tub. Upstairs, a spacious loft creates additional living or entertainment space, while a second suite impresses with dual vanities, granite counters, a separate shower and soaking tub, and two oversized walk-in closets. Two additional bedrooms, two full baths, and a conveniently located laundry room complete the upper level. Storage is abundant throughout, including a large under stair closet. Step outside to a serene backyard with tranquil water views from the screened, covered patio. Envision enhancing the space with a privacy fence and mature landscaping to create your own peaceful retreat. With a recent price improvement, this home presents outstanding value, flexibility, and the opportunity to personalize to your taste. Ideally located less than 20 minutes from Disney, Johns Lake Pointe is a beautifully maintained community offering resort-style amenities including a clubhouse with pool and kitchen, fitness center, yoga room, tennis courts, playground, and access to a public boat ramp on the 2,500-acre Johns Lake. Enjoy an exceptional lifestyle in a prime location, priced to allow the next owner to create a private oasis. Don’t miss the opportunity to make this remarkable home your own.

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)

Listing Agent: Carla Scherer (407-443-7482)

Remarks: One or more photo(s) has been virtually staged. One of the largest homes in the highly desirable Courtlea Oaks community, this spacious 5-bedroom, 4.5-bath pool home offers over 4,000 square feet of living space and an exceptional opportunity in the heart of Winter Garden’s golf cart district. The flexible floor plan includes a rare apartment above the garage connected to the main home, providing ideal space for guests, extended family, a private office, or additional living quarters. Important updates have already been completed by these original to the home owners, including a new roof and A/C systems installed just two years ago, offering peace of mind for the next owner. Step outside to enjoy a beautiful pool and a private setting backing to the West Orange Trail, perfect for biking, walking, and outdoor recreation right from your backyard. Located just minutes from historic downtown Winter Garden, residents enjoy boutique shopping, dining, breweries, and the award-winning Saturday Farmers Market, along with numerous festivals and community events throughout the year. With its generous square footage, versatile layout, and unbeatable location, homes like this rarely come available in Courtlea Oaks.

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

Listing Agent: Jennifer Coon (321-948-8056)

Remarks: Under contract-accepting backup offers. Welcome to this beautiful 3-bedroom, 2-bathroom home with a two-car garage in the heart of the Regal Pointe subdivision of Winter Garden. Upon entry, you are welcomed by the large kitchen overlooking the living room, embracing open-concept living. The kitchen features laminate countertops, a tile backsplash, a breakfast eating area, and stainless steel Whirlpool appliances. The primary bedroom offers a private retreat, situated on the opposite side of the house from the secondary bedrooms. The large, open living room provides sliding door access to a screened-in patio with a peaceful pond view, making it the perfect place to enjoy a morning coffee or evening drink. You’re conveniently located within 25 minutes of Orlando’s theme parks, the airport, and downtown Orlando. Schedule your showings today!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Discover Unmatched Elegance in the Coveted Twinwaters Subdivision! Welcome to your dream home, a breathtaking Winter Garden pool residence built in 2016, offering the perfect fusion of sophistication, luxury, and prime convenience. This property isn’t just a house – it’s your personal sanctuary. Grand Entrance That Stuns: Be greeted by an impressive 14-foot foyer adorned with a dazzling crystal chandelier. A beautifully crafted wooden staircase with iron balusters sets the tone for the home’s elevated style. From the moment you step inside, the open-concept layout invites you to explore spaces designed for both comfort and entertainment. Exquisite Interiors: Every detail exudes elegance. Stunning wood plank accent walls, gleaming 30-inch marble tiles, intricate tray ceilings, and granite countertops throughout create a refined yet warm atmosphere. Whether hosting friends or enjoying quiet family moments, this home is the ultimate setting. First Floor Features: Luxurious Master Suite: Tray ceiling, serene ambiance, and ample space for relaxation. Versatile Guest Suite: Ideal for guests or teens, offering privacy and comfort. Functional Spaces: A large and cozy family room, private office, formal living and dining areas, plus a service pantry with wine storage and a separate laundry room. Gourmet Kitchen: A chef’s paradise with a granite island and seating, deep basin sink, custom 50” solid wood cabinets with glass accents, glass tile backsplash, built-in oven and microwave, and a walk-in pantry. Second Floor Highlights: Expansive Upper Lounge: Large windows fill the space with natural light, making it perfect for relaxation. Bonus Room: Create your dream space—whether a music studio, movie theater, gym, or private office. Second Master Suite: Spacious and serene, with luxurious finishes. Four additional bedrooms, each offering comfort and versatility. Outdoor Oasis: Your backyard is a private paradise! A covered lanai overlooks lush landscaping, a pristine vinyl fence, and a sparkling pool. It’s the perfect retreat for relaxation or entertainment. Modern Conveniences: Solar-powered electricity for energy efficiency Whole-home water purification system Tankless water heater Crown molding throughout Tray ceilings and architectural enhancements that elevate the aesthetic Over 25k in Curtain Work Prime Location & Community Perks: Located in the sought-after Twinwaters community, enjoy access to a community pool and recreation area. Nearby, explore Winter Garden Village, Historic Downtown Winter Garden, Walt Disney World, and top-rated schools. Central Florida’s major highways, shopping, dining, and entertainment are all just minutes away. This home is truly one-of-a-kind.

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Tony Bardy Assis (407-796-7777)

Remarks: Welcome to The Orchard, a tidy gated community of townhomes in sought-after Winter Garden. This residence blends modern comfort with low-maintenance living, offering a bright, open layout that feels inviting from the moment you step inside. Thoughtful upgrades elevate every space—stylish flooring, fresh finishes, and a contemporary color palette create a clean, move-in-ready atmosphere. The kitchen serves as the heart of the home, featuring new appliances, fine cabinetry, sleek countertops, and a functional layout ideal for everyday living. The open-concept living and dining areas flow seamlessly to a private outdoor space, perfect for morning coffee or unwinding at the end of the day. Upstairs, spacious bedrooms provide comfort and flexibility, while the primary suite offers a peaceful retreat with generous closet space and an updated en-suite bath. A dedicated laundry area and attached garage add convenience to the home’s thoughtful design. Residents of The Orchard enjoy gated security, a tranquil pool area and playground, and a prime Winter Garden location just minutes from shopping, dining, top-rated schools, and the charm of downtown Winter Garden. Tastefully updated, well-maintained, and ideally located—this townhome is the perfect blend of style and convenience.

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

Listing Agent: Drew Ross (407-383-6497)

Remarks: Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes community in Winter Garden. This FULLY-REMODELED, 5-bedroom, 4-bath POOL/SPA home sits on a SERENE POND and offers 3,389 sq. ft. of beautifully designed living space on OVER HALF AN ACRE, complete with a three-car side entry garage. Four of the 5 bedrooms are conveniently located on the first floor (including the Primary Bedroom), with the 5th Bedroom, a full bath and a bonus loft located on the second level. Inside, the home features designer ENGINEERED HARDWOOD FLOORING throughout the main living areas and the downstairs primary suite. The CHEF'S KITCHEN is a showpiece, boasting THREE SLABS OF PERMIUM CALCUTTA QUARTZ, an ITALIAN MARBLE BACKSPLASH, 60-inch DOUBLE-STACKED ALL WOOD SHAKER CABINTRY, a handy FOOD PREP ISLAND, a BREAKFAST BAR and TOP-OF-THE-LINE SAMSUNG APPLIANCES! The family room features AUTOMATIC ROLLER SHADES and is open to the kitchen and features Cathedral ceilings, a huge picture window and French Doors to the inviting lanai and sparkling pool. The primary suite is a retreat of its own, offering a FULLY-RENOVATED, SPA-INSPIRED bathroom with floor to ceiling CALCUTTA TILE, a frameless glass shower, a freestanding soaking tub, tall custom cabinetry with WHITE EXOTIC CARERRA QUARTZ COUNTERS and a massive walk-in closet! Architectural details elevate every room, including Plantation Shutters, multiple sets of French Doors, tray ceilings, volume and cathedral ceilings, extensive crown molding, transom windows, recessed lighting, bead boarding and elegant custom millwork. Step outside to a stunning outdoor oasis. The completely remodeled pool and spa area is surrounded by 2100 sq. ft. of travertine decking that extends across the covered lanai and additional outside patio space—perfect for entertaining! The lanai ceiling is finished with tongue and groove wood planks, adding warmth and sophistication. Other major upgrades include NEW DOUBLE-PANE, THERMAL WINDOWS (2023), a 2019 ROOF a 2019 AC SYSTEM and rain gutters. The extended brick paver driveway and matching walkway enhance curb appeal, while the well-fed irrigation system coupled with the well water (filtered by the whole house WATER SOFTENER) help keep utility costs low. All of this is just 5 minutes from the 429, offering quick access to Orlando and surrounding areas. Downtown Winter Garden & Winter Garden Village are also nearby as well as numerous championship golf courses for all your shopping, dining and recreational needs! Nearby top-rated schools are just another plus! Call for your showing today if you want to be the lucky one to snag this one-of-a-kind home before someone else does!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Diane Sterling (407-761-0512)

Remarks: WOW!!! OVER $40,000 RECENT PRICE REDUCTION!! Experience refined Florida living in this beautifully enhanced home located within a highly desirable golf course community. Thoughtfully updated, the property offers both style and peace of mind with a roof replaced just five years ago and a recently sealed and painted exterior. Inside, the home is designed for both comfort and entertainment, featuring an immersive surround sound system throughout the main level and an impressive dedicated theater/bonus space. Every detail has been curated to elevate everyday living. Step outside to your own private retreat—an exceptional backyard showcasing a custom pool and spa with a striking grotto feature, creating the perfect setting for relaxing or entertaining guests year-round. Residents enjoy access to an array of resort-style amenities, including a clubhouse with dining, fitness center, tennis and basketball courts, beach volleyball, playgrounds, and an expansive community pool. Ideally situated just minutes from world-renowned attractions like Walt Disney World, with convenient access to major expressways and premier shopping and dining destinations nearby, this home offers the perfect balance of luxury, location, and lifestyle. One or more photo(s) have been virtually staged. PLEASE REMOVE SHOES BEFORE ENTERING THE HOME!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Juli Onorata (407-864-7701)

Remarks: Under contract-accepting backup offers. Welcome home to this immaculate and model-worthy SINGLE-STORY 4-bedroom, 3-bath home in the heart of Winter Garden. Situated on a FULLY FENCED private corner lot, this home offers a RARE 3-car garage and a true split floor plan with the primary suite privately separated from the secondary bedrooms—ideal for families, guests, or multi-generational living. The open-concept kitchen features a NATURAL GAS range, white cabinetry, granite countertops, glass display cabinets, built-in wine rack, and a large island with pendant lighting and seating. Wood-look tile flooring throughout (NO CARPET ANYWHERE!) adds style and durability to the homes seamless floor plan. The spacious primary suite includes a large walk-in closet and an ensuite bath with dual sinks, soaking tub, and separate walk-in shower. Three additional bedrooms are located on the opposite side of the home for added privacy. Enjoy outdoor living on the covered and EXTENDED LANAI, perfect for relaxing and entertaining. The privacy of the lot is the perfect spot for enjoying your morning coffee or a weekend afternoon with friends. Located in a desirable boutique community, of just 66 homes, the location offers easy access to all that Central Florida has to offer. You are just 10 minutes from Winter Garden Village and historic Downtown Winter Garden, home of arguably the largest and best farmers market in the country and every store, restaurant and coffee shop you can imagine. Orlando International Airport, Disney, Universal, Epic Universe, Sea World, and world class golf are all within 30 minutes. Call today for a private tour!

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Terri Schon (407-625-2670)

Remarks: Under contract-accepting backup offers. Exceptional Lakefront Pool Home in the Gated Community of Hickory Hammock in Winter Garden. Positioned on a quiet cul-de-sac overlooking Lake Claire and Johns Lake Conservation, this impeccably maintained 4-bedroom, 3-bath residence showcases 3,844 square feet of thoughtfully designed living space and a 3-car tandem garage, seamlessly blending luxury, comfort, and the Florida lakefront lifestyle. The private outdoor retreat is designed for unforgettable entertaining, featuring a resort-style saltwater pool and spa with sun shelf, pool heater (2017), fire bowls, and wireless controls for the pool, spa, lighting, and water bowl. A dramatic two-story screened enclosure frames the outdoor living space while preserving peaceful lake and conservation views, creating the perfect setting for relaxing or entertaining while enjoying the tranquil waterfront setting. Inside, the home blends elegance and functionality with tile flooring throughout the first floor and engineered hardwood on the stairs and bonus room. The expansive family room features a stacked stone fireplace with wood mantle, creating a warm focal point for gatherings. Crown molding, upgraded lighting, and thoughtful details are carried throughout. The chef’s kitchen is ideal for everyday living and entertaining, showcasing espresso cabinetry, a large quartz island, glass tile backsplash, and an updated butler’s pantry and bar area with quartz counters, custom shelving, and designer tile accents. The first floor includes a bedroom and full bath, ideal for guests or multi-generational living, and all secondary bathrooms throughout the home have been beautifully updated, creating a cohesive, move-in-ready feel. An oversized custom laundry room features a sink, folding station, walk-in storage, quartz counters, and negotiable washer and dryer. Upstairs, the primary suite offers a private balcony with sweeping views of Lake Claire, conservation, and the sparkling pool below. Step onto the private balcony and take in the serene views of the pool and Lake Claire, creating a peaceful retreat to start or end your day. The fully renovated spa-style primary bathroom includes dual vanities, a glass-enclosed tile shower with rain head, and a freestanding soaking tub. A custom primary closet and flex room perfect for an office or nursery, separated by a barn door, add versatility. Additional upgrades include smart heated toilets throughout, Sonos sound system with three zones, Trex garage flooring, a 50-amp EV charger, whole-house water softener and filtration system, new dishwasher (2025), and interior and exterior paint within the last four years. The solar panels will be paid off at closing, providing energy savings, and a termite bond is in place. Residents of Hickory Hammock enjoy resort-style amenities including a clubhouse, fitness center, community pool, fishing pier, tennis courts, volleyball courts, dog park, playground, walking trails, and golf-cart friendly streets. Conveniently located near downtown Winter Garden, Winter Garden Village, major highways, and approximately 20 miles to Orlando International Airport. A rare opportunity to enjoy private lakefront living in one of Winter Garden’s most desirable gated communities.

Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)

Listing Agent: Denise Gregorie (407-463-0080)

Remarks: One or more photo(s) has been virtually staged. Luxury living in one of Winter Garden’s premier gated communities. This stunning 5-bedroom, 4- bath estate offers 3,398 sq. ft. of thoughtfully designed living space, including a private office and upstairs bonus room—ideal for work, play, or entertaining. Enhanced with over $75,000 in designer upgrades, the home showcases expansive living areas, a gourmet kitchen with premium appliances, and elevated finishes throughout. The owner’s suite is a true retreat, featuring a custom walk-in closet and spa-inspired bathroom, while additional bedrooms provide comfort and privacy for family or guests. Perfectly located just minutes from Winter Garden Village, AdventHealth, top-rated schools, shopping, and dining, this home offers the ideal blend of elegance, convenience, and lifestyle. Seller concessions available. A rare opportunity to own a beautifully upgraded home in a highly sought-after community

Listing is courtesy of: EXP REALTY LLC (407-392-1800)

Listing Agent: Judith Enelus (407-722-4183)

Remarks: Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roff, new pluming, close to major roads, schools, minutes to Winter Garden dawn town.

Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)

Listing Agent: Rosa Rodriguez (407-832-1185)

Remarks: Under contract-accepting backup offers. Welcome to your new home in the heart of Winter Garden! Featuring a brand new roof and water heater 2026! This beautifully designed home offers the perfect blend of comfort, style, and modern amenities, making it an ideal choice for families and individuals alike. Step inside to discover a spacious interior featuring an open kitchen to the living space, providing ample storage and a contemporary feel. The kitchen is equipped with whirlpool matching appliances, granite countertops, also in all bathrooms. Large windows filling the space with natural light that add a touch of elegance. Step outside to your private fenced in backyard, where you can enjoy the Florida sunshine on your patio or host barbecues with friends and family. Residents have access to community amenities such as a swimming pool, playgrounds, and walking trails. Location is key, and this home does not disappoint! Situated in walking distance to downtown Winter Garden, you’ll have easy access to charming shops, renowned restaurants, and the vibrant farmers market held weekly. Plus, you are just a short drive away from all Central Florida attractions, including the beautiful beaches and major highways. With a low monthly HOA fee of just $63, which includes access to a community pool and yard maintenance, you can enjoy a worry-free lifestyle in this fantastic neighborhood. Don’t miss your chance to own this turn key home in one of the most desirable communities. THIS PROPERTY QUALIFIES FOR A $5,000 CREDIT WHEN USING FINANCING WITH PNC BANK LENDER! CERTAIN REQUIREMENTS DO APPLY! Schedule your private showing today and make 1261 Wintergreen Way your new home.

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Jason Lygren (407-756-9402)

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: 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: **** 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: 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: 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)

Remarks: Welcome to this fully renovated 3-bedroom, 2-bath home on an oversized 0.20-acre lot in one of Winter Garden’s growing corridors. This move-in ready property offers immediate livability with long-term upside. Recent upgrades include a new AC system and water heater (2026) and a roof replaced in 2019, minimizing near-term capital expenses. The home features updated interiors and a functional layout suited for both owner-occupants and investors. The large lot provides flexibility for outdoor use and potential future enhancements. Zoned R-4, the property may provide additional possibilities for expansion or income-producing use. Buyer to verify all zoning and development options with the city. Located just minutes from major highways, shopping, and ongoing development, this property is well-positioned for both convenience and future growth.

Listing is courtesy of: LIVE MVRK LLC (407-756-4563)

Listing Agent: Gabriel Flete (407-341-9663)

Remarks: Under contract-accepting backup offers. *Video Tour Available!* Experience the best of Florida living in the heart of Stoneybrook West, where resort-style amenities and a true sense of community come together. Behind 24-HOUR GUARD GATED ENTRANCE, you’ll find everything you need to live like you’re on vacation year-round—an Olympic-sized swimming POOL, splash zone, FITNESS CENTER, playground, tennis, basketball and pickleball courts, a fishing pier, plus a PRIVATE BOAT RAMP on Black Lake. Even better, the quarterly HOA INCLUDES SPECTRUM INTERNET AND CABLE, making life here as convenient as it is enjoyable. Tucked away on a quiet CUL-DE-SAC STREET with no through traffic, this home offers both privacy and charm from the moment you arrive. Warm curb appeal welcomes you inside to rich WOOD FLOORS and soaring ceilings that create a light, airy Florida feel. At the front of the home, the FORMAL LIVING AND DINING ROOMS provide flexible space for entertaining or working from home, highlighted by a welcoming staircase. Designed for gathering, the OPEN FLOOR PLAN seamlessly connects the family room and eat-in kitchen. The kitchen features abundant QUARTZ COUNTERTOPS, upgraded cabinetry, and a pantry to keep everything organized. Double sliding doors from both the kitchen and family room open to a SCREENED PATIO OVERLOOKING A PEACEFUL POND—no rear neighbors, just tranquil views and evening sunsets. Upstairs, you’ll find the bedrooms along with a convenient laundry room. The primary suite is spacious with wood floors, double sinks, quartz countertops, a water closet, and WALK-IN CLOSET. The RENOVATED SECOND BATHROOM offers a beautifully tiled shower and tub with a built-in shampoo niche. Generously sized secondary bedrooms feature deep closets for all your storage needs. Additional upgrades include a NEWER ROOF (2021), NEWER WATER HEATER (2024), ceiling fans throughout the home and patio, a convenient half bath downstairs, new irrigation panel, updated faucets and shower head in the primary bath, newer microwave and refrigerator, window blinds and exceptional storage throughout. This is more than a home—it’s your opportunity to embrace the Florida lifestyle, where sunny days, waterfront adventures, and a vibrant community are all right outside your door.

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

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