Homes for Sale Near West Orange High in Winter Garden - 148 homes

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: Located in the GATED community of Wintermere Pointe in Winter Garden, FL, this spacious .25 acre, 5-bedroom, 3-bath pool home for sale in Winter Garden offers nearly 3,750 square feet of well-designed living space just minutes from Winter Garden Village, Windermere, Walt Disney World, AdventHealth Winter Garden, SR 429, and the Florida Turnpike. Designed for both everyday living and entertaining, the home features an open-concept layout with formal living and dining rooms, a large family room, and a centrally located kitchen that flows seamlessly into the main living areas. A DOWNSTAIRS BEDROOM and full bath provide flexibility for guests, multi-generational living, or a private home office, while upstairs, the expansive primary suite offers a true retreat with a soaking tub , separate shower, dual vanities, and two walk-in closets. Additional bedrooms are generously sized, and both a LOFT and a large BONUS ROOM create endless possibilities for a media room, game room, home gym, or additional living space. High ceilings and natural light enhance the open feel throughout the home, while the layout offers both functionality and comfort. Step outside to a screened-in PRIVATE POOL, covered lanai and extended paver patio, perfect for enjoying Florida living in Winter Garden year-round, all set on a .25 ACRE LOT with mature landscaping and a FULLY FENCED backyard for added privacy. Wintermere Pointe is a well-established gated community in Winter Garden, Florida offering tennis courts, a playground, and a LOW HOA, and is zoned for Lake Whitney Elementary, SunRidge Middle, and West Orange High. If you’re searching for homes for sale in Winter Garden FL with a pool, gated community, and flexible layout, this home offers space, location, and lifestyle in one of Central Florida’s most desirable areas.

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

Listing Agent: Alexis Bress (407-900-0771)

Remarks: UPDATED THREE-STORY TOWNHOME IN THE HEART OF DOWNTOWN WINTER GARDEN! Welcome to 461 Geranium Place, where modern finishes, natural gas features, and one of Winter Garden’s most loved locations come together beautifully. This is the kind of home that changes your day-to-day rhythm — coffee, dinner, craft beer, the trail, live music, community events, and the SATURDAY FARMERS MARKET are all right outside your door. Located next door to Crooked Can and Plant Street Market, this stylish townhome offers a truly connected Downtown Winter Garden lifestyle. Inside, the home feels bright, polished, and easy to live in, with wood-look tile flooring, crisp white trim, crown molding, recessed lighting, modern door hardware, and decorative wall trim that adds a custom, finished feel. The three-story layout provides flexibility and function, while the ELEVATOR-READY design offers a valuable option for future convenience. The main living level is made for gathering. The kitchen, dining, and living areas flow together in one open, connected space, creating an easy setting for casual dinners, game nights, or hosting friends before walking next door to Plant Street Market. The kitchen features light cabinetry, quartz-style countertops, subway tile backsplash, stainless steel appliances, a NATURAL GAS RANGE, vent hood, pendant lighting, and an oversized island with seating. The dining and living areas offer generous space, abundant natural light, balcony access, and a comfortable layout that feels open without losing warmth. Decorative wall trim, tall windows, neutral finishes, and a modern stair railing add to the clean, contemporary presentation throughout the home. The primary bath features new flooring and a BRAND NEW STEAM SHOWER, recently replaced with floor-to-ceiling tile, a built-in bench, recessed niche, decorative tile accent, and a clean, spa-inspired feel. The separate vanity area offers excellent counter space and storage, while the overall bath layout provides comfort and function. Additional highlights include NATURAL GAS SERVICE, including a gas water heater, updated fixtures, excellent storage, and a cohesive neutral design palette throughout. With its updated interior, open main living level, flexible three-story design, and unmatched Downtown Winter Garden location, 461 Geranium Place offers a rare blend of comfort, convenience, and everyday enjoyment. This is the home where your weekends get easier, your evenings get more fun, and Downtown Winter Garden becomes part of your everyday life. Spend Saturday mornings at the farmers market, meet friends for dinner on Plant Street, enjoy craft beer next door at Crooked Can, hop on the West Orange Trail, and come home to a beautifully updated space that feels easy, stylish, and welcoming. Come see how well this home lives in person — schedule your private showing today.

Listing is courtesy of: THE ROSENBLOOM TEAM (407-376-4454)

Listing Agent: Cindy Rosenbloom (407-876-9175)

Remarks: There is a distinct rhythm to life in Oakland Park that cannot be replicated anywhere else in Central Florida. It is a refined balance of Old Florida charm and modern luxury, where tree-lined streets, curated green spaces, and intentional design create a true sense of place. As you enter the community, everything feels elevated and thoughtfully composed, with the 22-mile West Orange Trail serving as the heartbeat that connects residents to both nature and one another. At 931 Kylee Alley, this lifestyle is fully realized. Positioned on a prominent corner lot, this David Weekley Stoneybrook residence showcases timeless architecture with a clean, sophisticated presence. One of the greatest luxuries here is the ease of ownership. The homeowners' association provides full landscaping maintenance, allowing the property to remain in pristine condition without demanding your time. Your weekends are yours to enjoy, not manage. Inside, the home immediately impresses with intentional sightlines and natural light. Built in 2022, the design feels both current and enduring. Soaring ceilings and expansive windows, complemented by custom plantation shutters, create a bright yet grounded atmosphere. The gourmet kitchen anchors the home, featuring an oversized island with sleek, solid surface countertops that serve as the perfect setting for gathering, entertaining, or everyday living. The floor plan is designed for both connection and privacy. The main level offers a flexible and refined space that can function as a guest suite or executive-style home office. Upstairs, the private quarters provide a peaceful retreat. The primary suite is expansive and serene, complete with a spa-inspired bath designed for relaxation at the end of the day. Living here means immediate access to the West Orange Trail and the best of Winter Garden. Bike to Plant Street, enjoy the Saturday Farmers Market, or simply take in the charm of one of Central Florida’s most sought-after destinations. Within Oakland Park, residents enjoy resort-style amenities, including multiple pools, a clubhouse, and a dog park, all contributing to a true lock-and-leave lifestyle. From an investment perspective, this property stands out. It offers an exceptional price per square foot for Oakland Park, with pricing thoughtfully adjusted to reflect the opportunity for upstairs flooring customization. In a community where demand continues to outpace supply, especially for newer construction on premium corner lots, this home represents both immediate value and long-term upside. 931 Kylee Alley is more than a home. It is a strategic acquisition within one of Winter Garden’s most desirable communities.

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

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

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: Welcome to 15183 Sunrise Grove Court, a beautiful townhome located in the highly sought-after Hickory Hammock community in Winter Garden, Florida, where comfort, lifestyle, and an excellent location come together perfectly. Offering 1,844 square feet of living space and 2,393 total square feet, this property features 3 bedrooms, 2 full bathrooms, and 1 half bath, providing the layout and space today’s families truly value. From the moment you enter, you are welcomed by a bright, open design filled with natural light that creates a sense of spaciousness and warmth. The seamless connection between the living room, dining area, and kitchen creates the perfect environment for family gatherings, entertaining guests, or simply enjoying everyday life in comfort. The kitchen becomes the heart of the home, strategically connected to the main living areas so you can always stay part of every moment. Whether hosting special gatherings or enjoying quiet evenings at home, this space easily adapts to your lifestyle. On the second level, the primary suite offers a private retreat ideal for rest and relaxation. Spacious and thoughtfully designed, it provides both comfort and privacy. The additional bedrooms are versatile and can easily be used as family bedrooms, guest rooms, or a home office. Hickory Hammock is more than just a community—it’s a lifestyle. Residents enjoy resort-style amenities including a clubhouse, pool, fitness center, playground, and scenic walking trails surrounded by beautifully maintained green spaces. It’s a place where neighbors connect, families spend time together, and the atmosphere is peaceful and welcoming. Strategically located in Winter Garden near Horizon West, the property offers convenient access to highly rated schools, shopping centers, restaurants, major roadways, and the charm of Historic Downtown Winter Garden. It is also just a short drive from Orlando’s major employment centers and the area’s most popular attractions. Homes in this community are highly sought after and do not stay on the market for long. If you are looking for a home that combines space, comfort, and a true sense of belonging, 15183 Sunrise Grove Court may be exactly what you have been waiting for. Schedule your private showing today and come experience it in person.

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

Listing Agent: Natsue Siqueira (407-722-0850)

Remarks: Some properties check a box. This one opens a door. This 3-bed, 2-bath home in the heart of Winter Garden is more than a place to live. It's a wealth-building opportunity sitting in plain sight. The floor plan sets up beautifully for a duplex conversion: a 1/1 in the front and a 2/1 in the back. Live in one side and let your tenant cover the mortgage, or rent both and start building cash flow from day one. At approximately 1,184 sq ft, the footprint is manageable, the concept is proven, and the location makes it work. You're minutes from historic downtown Winter Garden, major shopping corridors, top dining, and highway access. The kind of address that attracts reliable tenants and holds long-term value in one of Orange County's strongest markets. House hacking, buy-and-hold, or straight investment play. However you run the numbers, this one makes sense. ROOF is 2020, WATER HEATER 2021 and HVAC 2016

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

Listing Agent: Phat Nguyen (407-452-8751)

Remarks: Under contract-accepting backup offers. Tucked away on a Private Street within a quiet cul-de-sac in the highly sought-after Gated community of Hickory Hammock, this exceptional 5 Bedroom, 4 Bathroom residence offers 3,908 sqft of thoughtfully designed living space with captivating views of Lake Burnett. Perfectly positioned to capture both Lake and Conservation Vistas, this home delivers the rare combination of Privacy, Comfort, and an Elevated Lifestyle in one of Winter Garden’s Most Desirable Neighborhoods. From the moment you enter, soaring 20-foot Ceilings in the foyer create a grand sense of arrival, complemented by a Formal Dining Room and immediate Sightlines to the Sparkling Pool and Tranquil Lake beyond, an unforgettable first impression that sets the tone for the entire home. Designed for both everyday living and entertaining, the first floor features Wood Plank tile throughout and an open, functional layout. The kitchen serves as the heart of the home, appointed with New Quartz Countertops, Stainless Steel Appliances, a Double Oven, abundant cabinetry, and an expansive Walk-in Pantry just off the Butler’s Pantry, complete with a JennAir Beverage and Wine Fridge. Thoughtful Lighting throughout enhances the warmth and livability of each space. Step outside to your Private Outdoor Retreat, where a Covered and Screened Lanai frames Peaceful Lake and Conservation Views. The Saltwater Pool with a Baja Shelf and Heated (electric) Spa invites year-round enjoyment, while the Spacious Backyard offers Plenty of Room for Kids or Pets to play, all while enjoying Stunning SUNSET VIEWS each evening over Lake Burnett and the Johns Lake Conservation area. A First-Floor Bedroom with a Full Bath provides flexibility for guests or multi-generational living. Upstairs, a generous Bonus Room offers endless possibilities for a media room, playroom, or additional living space. The Primary Suite is a true retreat, featuring Double Tray Ceilings and a Private Screened Balcony overlooking Lake Burnett, offering the perfect setting to take in breathtaking Sunset Views each evening. Secondary Bedrooms are well-appointed with Walk-in Closets, including one bedroom with an Ensuite Bathroom, while the remaining 2 Bedrooms share a well-designed bath. The tandem 3-Car Garage provides ample space for vehicles and storage, complemented by a spacious first-floor Laundry Room featuring New Quartz Countertops, a Sink, ample Cabinetry, and a Walk-in Closet. Residents of Hickory Hammock enjoy an impressive array of amenities including a Clubhouse, Fitness Center, Resort-style Pool, Fishing Pier, Tennis Courts, Sand Volleyball Courts, Dog Park, Playground, Walking Trails, and Golf-Cart-friendly streets. Conveniently located near Downtown Winter Garden, Winter Garden Village, major highways, Top-Rated Schools, and approximately 20 miles to Orlando International Airport. This home offers the Perfect Blend of Space, Functionality, and Desirable Water View Living - schedule your private showing TODAY.

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

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

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: Rare LAKEFRONT Gem in Highly Sought-After Westfield Lakes! This is your chance to own a stunning Taylor Morrison built LAKEFRONT pool home in the desirable Westfield Lakes community! Beautifully maintained and tastefully updated, this spacious 4-bedroom, 3-bath home also features an upstairs bonus room—perfect for a home office, media room, or guest retreat. From the moment you arrive, you’ll be captivated by the lush landscaping, brick paver driveway, and three-car garage. Step through the elegant stained glass double entry doors into a light-filled, split floor plan with luxury light wood vinyl plank flooring and plantation shutters throughout. The formal living and dining rooms offer sophisticated spaces for entertaining, while the heart of the home—the gourmet kitchen—was completely updated in 2018 and boasts double ovens, electric cooktop, microwave, designer pendant lighting, custom backsplash, and an oversized Cambria granite island that comfortably seats 8. The kitchen opens to a bright and inviting family room featuring a custom built-in entertainment center and electric fireplace. Enjoy peaceful lake views from the extended master suite, complete with tray ceiling and private seating area. The fully remodeled spa-like master bath (2023) offers a Roman tub, gorgeous walk-in shower, and dual sinks. The thoughtfully designed layout ensures privacy, with the second bedroom featuring an ensuite bath and pocket door, while bedrooms 3 and 4 are located at the rear of the home and share a third full bath. Bedroom 4, with double doors and lake views, is ideal for guests or a home office. Upstairs, the bonus room with double windows overlooking the lake provides even more flexibility. Step outside through French doors to your private lakefront oasis—a solar-heated pool and spa surrounded by an expansive brick paver patio, ideal for dining, relaxing, and entertaining. Located on Lake Beulah, an 18-acre natural spring-fed lake, this home offers tranquil views, non-motorized water activities, and an abundance of natural wildlife. Westfield Lakes features two community fishing docks, tennis courts, and two playgrounds. Additional highlights include: • New roof (2021) • New A/C units (2020) • Numerous updates throughout including new fans, designer lighting, and fixtures Prime location—just minutes to Winter Garden Village, charming downtown Winter Garden, top-rated schools (West Orange High School across the street), and with easy access to all major highways, theme parks, and Central Florida attractions. ? This is a true must-see lakefront paradise—schedule your private tour today!

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

Listing Agent: Mark Hide (407-832-7332)

Remarks: Nestled within the intimate Garden West enclave — just 11 exclusive homesites — this 4-bedroom, 3-bathroom J&J Building masterpiece spans 2,698 square feet of meticulously curated living space and sits directly on the West Orange Trail. Lace up your sneakers and you're seconds from one of Florida's premier multi-use trails, stretching 22 scenic miles through the heart of West Orange County. Located in the heart of Winter Garden's beloved Golf Cart District, Downtown Winter Garden's vibrant Plant Street is just a half mile away — putting award-winning restaurants, the beloved Saturday farmers market, boutique shops, and year-round community events right at your doorstep. From the moment you arrive, the Florida-inspired architecture, lush professionally re-landscaped grounds with low-voltage landscape lighting, and inviting covered front porch signal that every detail has been considered. Inside, the owners have transformed this already exceptional home into something truly turnkey. Two stunning shiplap feature walls anchor the main living spaces, while all-new designer lighting fixtures — inside and out — have been upgraded throughout and are fully programmable via the Leviton app, so you can set the perfect ambiance from anywhere. The chef's kitchen remains the heart of the home, featuring a Dacor 36" gas range, Samsung Pro dark stainless appliances, quartz countertops, subway tile backsplash, and ceiling-height cabinets beneath a one-of-a-kind shiplap vented hood. A reverse osmosis water filtration system at the kitchen sink adds a thoughtful, health-forward touch. Natural oak hardwood floors, crown molding, and custom woven wood window treatments on the first floor carry sophistication from room to room, while cordless blinds keep the second floor clean and effortless. The main floor offers an open living area with a guest bedroom and full bath — ideal for visitors or multigenerational living. The living room features a mounted, tilt-and-extend TV (included) paired with a Sonos sound system, controlled seamlessly by app for both the living room and lanai. Upstairs, the primary suite, two additional bedrooms, and a versatile loft provide space to spread out. Step outside and the screened lanai — enclosed with premium no-see-um screen material — becomes a true outdoor living room. Backyard café string lights, a mounted TV (included), Sonos audio, a natural gas BBQ stub-out, a retractable privacy blind, and no rear neighbors make this the ultimate Florida entertaining space. Additional outdoor power outlets and thoughtfully designed landscape lighting round out the backyard experience. Built for efficiency and peace of mind, the home features spray foam insulated block walls, energy-efficient double-pane windows, a radiant roof barrier, and a tankless gas water heater. Programable keyless entry locks secure all exterior doors, including the garage. The detached two-car garage — complete with a dedicated golf cart bay and overhead SafeRack storage — connects to the main house via a covered breezeway, a nod to the community's lifestyle-first design. This is more than a home. It's a lifestyle — trail, town, golf cart community, and turnkey luxury all in one.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Alexis Anderson (561-670-5901)

Remarks: A rare opportunity for a completely renovated home in rural Avalon Groves and no HOA. Situated on 2.5 private acres, this beautifully remodeled farmhouse inspired estate offers peaceful country living with modern comfort and thoughtful design throughout. This spacious home features 6 bedrooms and 3.5 bathrooms and has been extensively updated within the last year. New septic tank added (now making 2 septic tanks in 2026). New roof. Tankless hot water heater. Brand new gates and fencing. The interior offers open living spaces filled with natural light, high quality finishes, and top of the line appliances throughout. Every detail has been carefully selected to create a warm and welcoming atmosphere while maintaining functionality for everyday living. The primary suite serves as a private retreat, highlighted by an expansive bathroom that is comparable in size to a bedroom. Designed for comfort and relaxation, this space offers both luxury and privacy. Outdoors, the property continues to impress with a private pool and generous acreage providing flexibility for a variety of uses. Dedicated boat and RV storage offers added convenience for those who enjoy an active lifestyle. Two separate private gated entrances provide enhanced accessibility and privacy. This property presents a rare opportunity to enjoy acreage living while still benefiting from modern updates and refined finishes in the Rural Avalon Groves area, while being only 5 minutes away from all your shopping, restaurants and groceries.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Kerstin Crow (615-428-7046)

Remarks: Under contract-accepting backup offers. Welcome to this stunning architectural masterpiece nestled in the heart of Twinwaters, one of Winter Garden’s most sought-after communities. This elegant two-story home seamlessly blends sophistication and comfort, offering over 3,600 square feet of beautifully designed living space. Step through the grand entryway to find soaring ceilings, expansive windows that fill the home with natural light, and designer finishes that exude contemporary luxury. The gourmet chef’s kitchen is a true showpiece—featuring 42” custom cabinetry, gleaming quartz countertops, a massive entertainment island, stainless steel appliances, and a walk-in pantry, perfect for culinary enthusiasts and family gatherings alike. The open-concept great room flows effortlessly into a spacious dining area and covered lanai, ideal for both indoor and outdoor entertaining. Upstairs, the luxurious primary suite offers a serene retreat with a spacious walk-in closets, a spa-inspired bathroom with a deep soaking tub, frameless glass shower, and dual vanities. A versatile loft provides additional space for a home theater, gym, or play area, while the first-floor guest suite ensures comfort and privacy for visitors. The private backyard invites you to create your own oasis—whether adding a pool, summer kitchen, or lush garden escape. Enjoy resort-style amenities including a community pool, playground, and picturesque walking trails, all surrounded by pristine lakes and lush landscaping. Twinwaters is ideally situated near Horizon West, top-rated schools, fine dining, boutique shopping, and major highways for an easy commute to downtown Orlando and world-famous attractions. This home truly embodies the ultimate blend of luxury, location, and lifestyle—a rare opportunity to live beautifully in one of Central Florida’s premier communities.

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

Listing Agent: Jay Winston (407-497-1112)

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: Under contract-accepting backup offers. 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: Short Sale. SHORT SALE APPROVED READY TO CLOSE AND MOVE-IN READY and quietly positioned within a well-established Winter Garden community, this updated 2-bedroom, 2-bath condo offers a NEW ROOF, and an easy, comfortable lifestyle in one of Central Florida’s most desirable areas. Approaching the home, you’ll appreciate the tucked-away cul-de-sac location with paved private streets and sidewalks that create a calm, residential feel. Step inside through the front entrance and you’re immediately welcomed into a bright, open living space where natural light enhances the clean layout and efficient use of square footage. The living room feels inviting and functional, offering enough space to relax, entertain, or simply enjoy a quiet evening at home. Continuing through the home, the upgraded kitchen with GRANITE counter tops, anchors the main living area with modern appliances, ample cabinetry, and practical counter space. Its open connection to the living room allows for easy conversation while cooking, hosting, or enjoying everyday routines, making the space feel connected and intentional. The primary bedroom is set apart as a comfortable retreat, featuring brand-new carpeting and a private en-suite bathroom. The bathroom has been thoughtfully renovated with updated finishes that feel fresh and clean without excess. The secondary bedroom is well-sized and flexible, ideal for guests, a home office, or additional living space, with a second fully updated bathroom conveniently nearby. Throughout the condo, the layout flows efficiently from room to room, offering smart storage, comfortable proportions, and a low-maintenance design well suited for full-time living or long-term ownership. Assigned parking adds convenience, while the community’s shared amenities—including a COMMUNITY POOL—enhance the overall lifestyle. Located just minutes from downtown Winter Garden, residents enjoy close proximity to local shops, dining, farmers markets, and the West Orange Trail. Easy access to major highways makes commuting throughout Central Florida simple, whether heading toward downtown Orlando, major employment centers, or nearby attractions. This location is ideal for buyers exploring Orlando homes for sale or those planning an Orlando relocation home in a walkable, community-oriented area. While not intended as a short-term rental investment, this Winter Garden property represents a strong opportunity within the Central Florida real estate market for buyers seeking comfort, location, and value. Contact us today for a private tour or more details on this exceptional opportunity.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Simi Lakhani (407-408-7393)

Remarks: Perfectly positioned fronting one of Oakland Park’s picturesque green spaces, this exceptional home offers a rare opportunity to enjoy PARK-SIDE living in one of Winter Garden’s most celebrated communities. Oakland Park, a PARADE of HOMES award-winning neighborhood, is admired for its timeless architecture & inviting outdoor spaces that create a true sense of community. This beautifully designed Seaside floorplan blends classic charm with modern livability, offering 4 bedrooms, 3.5 baths, a STUDY, dining area, spacious loft, oversized garage, & FENCED yard. The primary suite is conveniently located on the main level, creating a peaceful retreat complete with a generous walk-in closet, a separate linen closet, & direct access to the laundry room, which has been enhanced with custom cabinetry for optimal storage & organization. Upstairs, the loft provides a versatile secondary living area—ideal for a media room or play space—accompanied by three additional bedrooms & two full baths, including one private en-suite. At the center of the home, the expansive kitchen is designed for both everyday living & effortless entertaining, enhanced with under cabinet lighting & tile backsplash. Abundant cabinetry & extensive counter space provide exceptional functionality, while the large island offers ample seating, making it the natural gathering place for family & guests alike. The adjoining dining area is equally impressive, featuring a dedicated buffet—perfect for hosting celebrations, holidays, or casual dinners. The home showcases rich WOOD flooring throughout the main living areas, adding warmth and sophistication, while soft carpeting in the bedrooms enhances comfort & tranquility. One of the home’s most captivating features is the inviting wraparound front porch, where French doors open to sweeping views of the beautifully maintained park. The home’s outdoor living continues in the screened rear porch, thoughtfully designed with retractable screens to maximize comfort & flexibility throughout the seasons. Beyond the porch, the backyard has been carefully curated as a private entertainment retreat. A paver patio anchors the space, complemented by a cozy FIRE-PIT, additional seating areas, & an outdoor kitchen featuring a built-in grill, mini fridge, & sink. Pet lovers will appreciate the dedicated dog area finished with low-maintenance artificial turf, creating a convenient & attractive space for four-legged family members. With its prime park-front location, versatile living spaces, & thoughtfully designed indoor-outdoor lifestyle, this home offers an exceptional blend of elegance, comfort, & community. Just a short GOLF CART ride away, you’ll find the charm and vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails, including access to the 22 mile long WEST ORANGE TRAIL. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Ashley Boyd (321-209-5540)

Remarks: Welcome to 13728 Fox Glove St, a MOVE-IN READY luxury home on the 14th hole in the guard-gated golf community of Stoneybrook West in Winter Garden. This 5-bedroom, 3.5-bath home offers nearly 3,400 sq ft with soaring ceilings, abundant natural light, and an open-concept layout perfect for living and entertaining. Neutral tones create a bright, timeless feel throughout. Enjoy seamless indoor-outdoor living with dual sliding doors leading to an oversized covered lanai, screened pool, and stunning golf course views. Major updates include a NEW ROOF (2025), NEW UPSTAIRS AC (2025), and DOWNSTAIRS AC (2022). Community amenities include 24-hour security, golf, clubhouse, fitness center, resort-style pool, sports courts, playground, fishing pier, and Black Lake access with boat ramp. Convenient to Winter Garden Village, SR-429, and downtown Winter Garden. TOP RATED SCHOOLS! Call today!

Listing is courtesy of: CRYSTAL CLEAR REALTY LLC (904-716-1927)

Listing Agent: Crystal Duckworth (904-716-1927)

Remarks: Pre-Construction. To be built. Welcome to one of the most anticipated new builds at Grove at the Harvest District — the Sunburst Plan by Davila Homes, a luxury new construction masterpiece designed for those who prioritize space, style, and lifestyle. Spanning 4,204 livable square feet with 5,665 total square feet, this stunning 5-bedroom, 5.5-bath estate is thoughtfully designed from the ground up to blend elevated living with effortless entertaining. Every inch reflects Davila Homes' signature commitment to superior craftsmanship, custom finishes, and exceptional attention to detail. Step inside and discover a floor plan built for the way you actually live — an executive office for focused work, a versatile loft for flexible living, and a gracious layout that flows naturally from the heart of the home to the outdoors. The second-floor covered terrace invites year-round relaxation with a front-row view of your private retreat below, where a custom pool and fully equipped summer kitchen set the stage for unforgettable gatherings. The three-car garage rounds out a home that delivers on every level — from daily functionality to that rare feeling of arriving somewhere truly special. Located within the coveted Grove at the Harvest District, this is more than a home — it's a legacy address in one of Central Florida's new communities.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Alexis Anderson (561-670-5901)

Remarks: Refined Waterfront Living in Winter Garden’s Coveted Golf Cart District! Set within one of Downtown Winter Garden’s most desirable gated enclaves, this exceptional waterfront residence offers a rare blend of sophistication, privacy, and effortless Florida living—perfectly positioned in the highly sought-after golf cart district. Designed to maximize light and livability, the interiors are bright and inviting. Recent enhancements include new exterior paint (2026), a tankless water heater (2026), and a added ensuite bathroom (2026) making two primary suites on the second floor. Generous storage is thoughtfully integrated with expansive closet space, while a whole-home water softener and purification system, including an under-sink filter, ensures elevated everyday comfort. At the heart of the home, the gourmet kitchen is both functional and beautifully appointed, featuring dual sinks, a dedicated prep island, and upgraded soft-close cabinetry. The oversized three-car garage provides ample room for vehicles, storage, or recreational needs. Outdoors, the lifestyle truly unfolds. A recently resurfaced covered boat dock—complete with lift, lighting, fan, and sink—offers direct access to one of Florida’s largest spring-fed lakes, part of the Harris Chain and extending to the St. Johns River and Atlantic Ocean. The expansive grounds are enriched by mature, fruit-bearing trees including mango, avocado, star fruit, and citrus, creating a lush, private retreat. Surrounded by natural beauty, the property attracts an impressive array of wildlife. Unforgettable sunrises and sunsets can be enjoyed from multiple vantage points, including the living spaces, patio, dock, and three north-facing bedrooms with water views. This is a home that seamlessly balances elegance and ease—offering a rare opportunity to experience serene waterfront living in one of Winter Garden’s most iconic settings.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Alexis Anderson (561-670-5901)