Homes for Sale Near Lakeview Middle in Winter Garden - 59 homes

Remarks: Beautifully updated POOL home in the desirable Tuscany community! Major updates include a new water heater (2020), whole house re-plumed (2021), new saltwater pool/spa with panoramic screen (2022), and new HVAC (2024). Pool features include Heat pump/chiller combo, iAquaLink (an intelligent pool control-turn on filter, lights, spa through app), auto fill/auto drain, bubbler, and Eco pool feature (circulation). Kitchen features quartz counters, 42” cabinets, stone backsplash, and stainless appliances, opening to a cozy family room with fireplace and French doors to the pool. Enjoy a private primary suite with pool access and a luxurious bath. Additional highlights include crown molding, 10-ft ceilings, bamboo/slate/travertine flooring, smart thermostat, and a fully fenced backyard. Excellent location near the West Orange Trail, downtown Winter Garden, and SR 429. This home truly shines!

Listing is courtesy of: RE/MAX DOWNTOWN (407-770-2050)

Listing Agent: Marlon Vega (407-791-0572)

Remarks: Under contract-accepting backup offers. Welcome to 1550 Coluso Dr, a beautifully updated 3 bedroom, 2.5 bathroom home offering 1,997 square feet of comfortable living space on just over a 1/3 acre lot, all within the city limits of Winter Garden and only about 2 miles from the charm, dining, and entertainment of downtown Winter Garden. This home features a spacious open layout designed for both everyday living and entertaining. The main living areas are finished with bamboo flooring installed in 2022, creating a warm and modern feel throughout. The kitchen has been fully remodeled with solid wood cabinetry, quartz countertops, and stainless steel appliances, making it both stylish and functional. A brand new Bosch stainless steel dishwasher was added in 2025, and updated pantry shelving provides added storage and organization. The primary suite offers a true retreat with a completely remodeled bathroom completed in 2025, featuring dual sinks and a large dual shower setup. Additional upgrades throughout the home include new carpet in the bedrooms (2021), updated lighting fixtures and blinds (2023), and ceiling retexturing (2021). Step outside to enjoy a screened in covered patio overlooking a spacious backyard with young fruit trees planted in 2024, perfect for relaxing or entertaining. The courtyard was refreshed in 2023, and a backyard shed provides extra storage. Major system updates include a brand new HVAC system installed in 2025, giving peace of mind for years to come. With its oversized lot, thoughtful upgrades, and prime location near one of Central Florida’s most desirable downtown areas, this home offers the perfect blend of comfort, style, and convenience.

Listing is courtesy of: HOME ON YOUR OWN REALTY (407-461-0127)

Listing Agent: Dustin Thibeault (407-461-0127)

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: Welcome to one of Winter Garden's most coveted addresses — nestled in the heart of the Golf Cart District, this beautifully appointed Oakland Park home delivers the Florida lifestyle you've been waiting for. With 4 bedrooms, 3.5 bathrooms, and 3,012 square feet of thoughtfully designed living space, this 2013-built corner lot residence blends everyday comfort with elevated finishes at every turn. Step inside to soaring vaulted ceilings in the family room that create an immediate sense of volume and light. Rich wood flooring flows through the downstairs living areas, complemented by clean ceramic tile and plush carpet in the bedrooms — a seamless combination of warmth and function. The open layout is designed for real living, whether it's a quiet evening in or hosting the people you love most. Outside, brick pavers set the tone for an outdoor living experience that's genuinely special. A large covered back patio creates the perfect setting for morning coffee or evening entertaining, while a classic breezeway connects the home to the garage with both style and practicality. But it's the location that truly sets this home apart. Oakland Park is one of Central Florida's most sought-after communities — complete with two resort-style pools, a beautifully appointed clubhouse, and a dedicated dog park. Step outside your door and hop on your golf cart to access the iconic West Orange Trail, or cruise just minutes into the heart of Downtown Winter Garden, where Plant Street Market, award-winning restaurants, rooftop bars, and a thriving local food scene await. This is the rare home where community, convenience, and character all converge.

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

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

Remarks: Under contract-accepting backup offers. Rare opportunity in Winter Garden! This property sits on approximately one acre with no HOA, offering exceptional space, flexibility, and privacy in a highly desirable location. Conveniently located just minutes from Downtown Winter Garden), with easy access to major roadways, shopping, dining, and top-rated schools—and even the option to ride your golf cart into downtown to enjoy everything the area has. The expansive lot provides ample room for RVs, boats, recreational vehicles, and more, making it ideal for those seeking additional space and versatility. The home features generous living areas and a functional layout with great potential for customization or renovation. Outdoor amenities include a private pool, hot tub, and an extended driveway with plenty of parking space. Located approximately 2 miles from Lake Apopka and about 3 miles from Downtown Winter Garden. Properties with this amount of land and no HOA in this area are rare—schedule your showing today!

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

Listing Agent: Estefania Ortega (305-905-7670)

Remarks: Welcome to your opportunity to own in one of the most desirable locations near downtown Winter Garden—just off iconic Heritage at Plant Street in GOLF CART DISTRICT. This beautiful 3-bedroom, 2.5-bath home offers nearly 1,700 square feet of thoughtfully designed living space in an unbeatable setting. Step inside to an expansive great room featuring stylish wood-look tile and an open-concept layout that seamlessly connects the living, dining, and kitchen areas—perfect for entertaining. The kitchen is designed for both function and style, offering abundant stylish cabinetry, gorgeous backsplash, elegant gold hardware, granite countertops, NEW Refrigerator, NEW microwave, NEW dishwasher, GAS stove and generous prep space. A screened courtyard with pavers creates a more private/secure outdoor retreat between the home and the detached 2-car garage. Whether you envision an outdoor lounge, garden oasis, or entertainment space, the possibilities are endless. Upstairs you will find upgraded- low maintenance flooring through out and your own private owner’s retreat. The spacious primary suite features a walk-in closet and an impressive ensuite bath designed to impress. Two additional bedrooms share a full bathroom, offering flexibility for guests, family, or a home office setup. A convenient half bath is located downstairs for visitors. Enjoy your summer months cooling off in the COMMUNITY POOL which is located just a couple of minutes from your front door. This community is ideally positioned between the West Orange Trail Park and the Winter Garden Branch Library, and just minutes from the 429 for easy commuting. If you like to run or bike this home is the perfect place for you since it is located along the West Orange Trail. Walk—or hop on your golf cart—to downtown Winter Garden where you’ll enjoy the vibrant atmosphere of Plant Street Market, known for its local food vendors, craft brews, artisan goods, and year-round community events. Located close to the community pool and surrounded by everything that makes Winter Garden special, this home truly offers the lifestyle buyers are searching for. Lower utility bills since it's an inside unit, double pane windows and a Instant Hot Gas Water Heater. Schedule your private showing today and experience why this location is so highly sought after.

Listing is courtesy of: CORCORAN CONNECT LLC (407-953-9118)

Listing Agent: Milinda Knollinger (321-624-7384)

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: Experience refined Florida living in the heart of Winter Garden, where timeless architecture, thoughtful design, & an unbeatable location come together in this exceptional custom-built residence. Situated on an expansive corner lot (~1/4 of an acre) overlooking one of the community’s most beloved PARKS, this four-bedroom (w/ room for a 5th & office), four-bath luxury HEATED POOL home offers privacy, space, & picturesque views. You’re moments from stunning sunsets, a walk by the LAKE, multiple parks & playgrounds, the community clubhouse, & direct access to the scenic WEST ORANGE TRAIL— a 22-mile paved trail ideal for biking, jogging, & casual strolls. From the moment you arrive, the stunning brick-accented front porch sets the tone, offering a welcoming space to relax while enjoying tranquil park views. Inside, rich wood flooring flows throughout the main living areas, complementing the home’s elevated finishes, such as crown molding, wainscoting, trim work, & custom built-ins. At the heart of the home, the chef’s kitchen is a true showpiece. Outfitted with premium Thermador & JennAir appliances, QUARTZITE counters, custom cabinetry, designer fixtures, a walk-in pantry, & spacious gathering space, this kitchen was designed for both everyday living & elegant entertaining. The adjacent dining & living areas are bathed in natural light, enhanced by multiple French doors that frame panoramic views of the pool and backyard retreat. The indoor-outdoor connection is simply spectacular. Step outside to your private oasis featuring a sparkling resort-style pool (runs with an ozonator) with travertine decking, generous covered lanai, & an outdoor kitchen equipped with a mini fridge & 48 inch griddle. Each of the four bedrooms is generously sized, offering comfort & versatility for family & guests. One generously sized bedroom is downstairs, which has access to the pool & park through French doors. The primary suite serves as a luxurious retreat with a spa-like bath & dual closets, while all four baths (three en-suite) are thoughtfully designed with quality finishes (marble upstairs, quartzite downstairs). Need an elevator? There's space for the addition! A well-appointed MUDROOM adds everyday convenience & organization, seamlessly blending practicality with style. Additional FEATURES: whole house water filtration system, in-ceiling speakers in the living room, the lanai by the pool, & front porch, tankless water heaters, hard wired cameras inside/out, ample storage, landscape lighting, Cat 6 wiring w/ WiFi access points, & an OVERSIZED garage (~2 1/2). Just a short GOLF CART ride away, you’ll find the charm & 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, community 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. 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. Custom built POOL homes are RARE to market in Oakland Park. Make this DREAM home your reality today!

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

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

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)

Remarks: Under contract-accepting backup offers. Welcome to this charming and beautifully updated 3-bedroom, 2-bath bungalow located minutes from the heart of highly desirable Winter Garden! This move-in ready home offers the perfect blend of character, comfort, and modern upgrades—including a brand-new roof for peace of mind. Step inside to discover a warm and inviting layout with stylish updates throughout, creating a light and airy feel that’s perfect for both everyday living and entertaining. The cozy bungalow design offers functionality and charm, making it an ideal primary residence, second home, or investment opportunity. Living in Winter Garden means enjoying one of Central Florida’s most sought-after communities, known for its historic downtown, vibrant lifestyle, and strong sense of community. Just minutes away, you’ll find the award-winning Winter Garden Farmers Market, held every Saturday and featuring over 100 vendors, live music, and a lively, family-friendly atmosphere . Stroll along the charming brick-lined streets of downtown, filled with boutique shops, local dining, and cultural attractions. Don’t miss your opportunity to own this adorable, updated bungalow in one of Central Florida’s most beloved communities—schedule your private showing today!

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

Listing Agent: Tara Heard (407-637-4634)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautiful and spacious 4-bedroom, 2-bath home located in the desirable Fullers Crossing Community in charming Winter Garden. This well-maintained residence has over 2,500 square feet of comfortable living space, perfect for families and those who love to entertain. Step inside to discover a bright open floor plan featuring generous living and dining areas, a large kitchen with plenty of cabinet space, and a welcoming family room that flows seamlessly for everyday living. Conveniently located just minutes from shopping, dining, major highways, and the historic downtown district of Winter Garden, known for its popular farmers market, scenic trails and vibrant community events. You couldn't miss this incredible opportunity to own a beautiful home in one of the Central Florida's most sought-after areas. Contact agent to request your showing today! Some photos have been virtually staged.

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

Listing Agent: Dulce Moise (407-697-4754)

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: Welcome to your new dream home! Located in the gated community of Tucker Oaks, this 2-story townhome offers 3 bedrooms, 2.5 bathrooms, and 1,544 square feet of comfortable, thoughtfully designed living space. As a corner unit backing to a peaceful conservation area, you’ll enjoy added privacy and tranquil views with no rear neighbors! Step inside to an open-concept first floor where high ceilings, recessed lighting, and natural light create a warm and inviting atmosphere. The layout is ideal for both everyday living and entertaining, with a seamless flow between the living, dining, and kitchen spaces. A conveniently located half bath downstairs adds ease and privacy when hosting guests. The kitchen is designed for functionality and style, featuring stainless steel appliances, crown-molded cabinetry, ample counter space, and a breakfast bar that’s perfect for quick meals or morning coffee. Upstairs, all bedrooms and full bathrooms are tucked away for optimal privacy. The primary suite offers a spacious retreat with a large closet and a private en suite bath complete with a generous vanity and a roomy shower, making it perfect for starting your day or winding down in the evening. Additional bedrooms provide comfortable space for family, guests, or a home office setup. Beyond the home, Tucker Oaks offers amenities including a community pool, playground, dog park, and sidewalks for enjoying the outdoors. The location places you just minutes from major highways, making commuting simple, while also being close to downtown Winter Garden where you can explore local farmers markets, community events, and boutique shopping. The nearby West Orange Trail offers even more ways to stay active and enjoy the Florida sunshine. With theme parks like Walt Disney World and Universal Studios just 25 minutes away, this home combines convenience, comfort, and lifestyle all in one. Don't wait on this amazing opportunity, schedule your private showing TODAY!!!

Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)

Listing Agent: Daniel Deluca (407-916-9780)

Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. 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: This stunning home is waiting just for you! Nestled in the gated community of Brandy Creek, this beautifully maintained 3 bedroom, 2 bathroom home offers a seamless blend of inviting living spaces and everyday functionality. A manicured front lawn, spacious driveway, and covered front patio set the tone for the warm welcome waiting inside. Step through the entry and you’re greeted by soaring ceilings, abundant natural light, and an open layout that effortlessly connects each living space. To one side, a formal living area offers flexibility as a home office or quiet retreat, while the formal dining room on the opposite side creates the perfect setting for hosting dinners and celebrations. At the center of the home, the kitchen shines as both a gathering place and a functional workspace. Featuring a large island with breakfast bar seating, stainless steel appliances, and generous counter space, it’s designed to handle everything from quick mornings to full-scale entertaining. Overlooking the family room, the layout ensures you’re always part of the moment. Just beyond, a cozy dinette with a partial bay window offers a peaceful spot to enjoy your morning coffee while looking out over the backyard. The split floor plan provides privacy for everyone, with the primary suite tucked away on one side of the home. This spacious retreat features a large closet, a private en suite bath with dual vanities, a garden tub, and a separate shower, plus its own direct access to the backyard. Additional bedrooms are bright, well-sized, and versatile for family, guests, or hobbies. Outside, the fenced backyard offers a private escape with a covered patio perfect for al fresco dining, weekend barbecues, or simply soaking up the Florida sunshine. It’s a space designed for both relaxation and play, with room for everyone to enjoy. Living in Brandy Creek means more than just a beautiful home, it also means you’ll also have access to a scenic lake and a dock/fishing pier for quiet moments outdoors. Just minutes away, you can explore the charm of downtown Winter Garden with its farmers markets, live music, boutique shopping, and local dining. With easy access to the Turnpike and FL-429, getting around Central Florida is simple and convenient. Don't miss out on this gorgeous home, schedule a private showing TODAY!!

Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)

Listing Agent: Lindsay Grosshans (407-202-2954)

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: Price Improvement! Exceptional new value. Seller motivated. Welcome to this beautifully maintained 4-bedroom, 2-bathroom single-family home located in the highly desirable Garden Heights community of Winter Garden, offering a prime location with NO HOA. Recently improved in price, this home now presents an even stronger opportunity in today’s market, combining location, upgrades, and value in one of Winter Garden’s most sought-after areas.Thoughtfully designed with a functional split floor plan, this residence offers 1,700 sq ft of living space filled with natural light and two separate living areas that provide both comfort and flexibility. Sliding glass doors open to a brand-new screened patio (2025), creating the perfect indoor-outdoor lifestyle for relaxing or entertaining.The interior features a beautifully updated kitchen and bathrooms, luxury vinyl plank flooring throughout, and modern upgrades including a whole-house water filtration system.Set on an expansive 0.29-acre lot, the property offers city water and sewer, along with ample space to add a pool or design a custom outdoor retreat. Conveniently located just minutes from Downtown Winter Garden, Lake Apopka, the Historic Old Winter Garden Golf District, shopping, top-rated schools, and easy access to SR-429. Homes with this combination of location, updates, and improved pricing are rarely available. Seller motivated—don’t miss this opportunity.

Listing is courtesy of: MARCILLO REAL ESTATE LLC (954-297-3636)

Listing Agent: Maria Barrios Tovar (407-600-4040)

Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bathroom single-story home in highly desirable Winter Garden, Florida! This light and bright residence features an inviting open floor-plan with soaring high ceilings that create a spacious and airy feel throughout. The cozy wood-burning fireplace serves as a beautiful focal point in the main living area—perfect for relaxing evenings at home. The property sits on a spacious corner lot with a fully fenced backyard, offering privacy and plenty of room for outdoor entertaining, pets, or play. A large storage shed (10x16) designed to match the home provides excellent space for tools, hobbies, or additional storage. Located within Winter Garden’s popular golf-cart district, you’ll enjoy easy access to the vibrant historic downtown area. Cruise over to the shops, restaurants, and the beloved weekly farmers market, or take part in the many community festivals and events that make Winter Garden such a special place to live. With its desirable location, open layout, and charming features, this home offers the perfect blend of comfort, convenience, and small-town charm. Call today as these opportunities tend to go fast!

Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)

Listing Agent: Jim Kernohan (407-450-3861)

Remarks: Welcome to Golf Cart Life in Historic Downtown Winter Garden! Nestled within Stanton Estates — an exclusive enclave of just 45 luxury homes — this stunning contemporary masterpiece is perfectly positioned in Winter Garden's coveted Golf Cart District. Built in 2018, this one-story multigenerational estate delivers 3,170 square feet of refined living on a nearly 1/3-acre lot, just a short golf cart ride from Plant Street, the Crooked Can Brewery, the weekly farmer's market, and the West Orange Trail. Inside, soaring 12-foot ceilings and abundant natural light flow through an open, flexible floor plan with four bedrooms, four full bathrooms, and a large private office. The gourmet kitchen is the heart of the home — featuring solid wood cabinetry, quartz countertops, an oversized center island, walk-in pantry, and a full suite of KitchenAid Professional appliances with a natural gas cooktop. The primary suite impresses with a recessed ceiling, expansive custom walk-in closet, and a spa-inspired oversized bath. Step outside through fully retractable sliding glass doors to a covered lanai wrapped in mature, professionally designed landscaping and privacy fencing — your own Florida retreat. Premium finishes throughout include smart home technology, motorized shades, whole-home water filtration, 8-foot solid core interior doors, colonial-style trim, custom cabinetry, a three-car tandem garage with brick paver driveway, and a brand-new tankless gas water heater (2025). Minutes from Disney, Universal, and SeaWorld, with seamless access to SR-429, the Turnpike, and 408 — this is one of Central Florida's most desirable addresses. Opportunities like this in Stanton Estates are rare. Welcome home.

Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)

Listing Agent: Joe Thomas, Jr (813-724-1922)