Homes for Sale Near West Orange High in Winter Garden - 135 homes

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: 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: 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. Ideally located in the heart of Winter Garden, this home offers 3,474 sq. ft. of living space and exceptional walkability just steps from Winter Garden Village’s shopping, dining, and everyday conveniences. Recent updates include new carpet and fresh interior and exterior paint. The flexible floor plan features five bedrooms, three full bathrooms, and a kitchen with 42-inch upper cabinets, granite countertops, and an open layout to the family room with a large eat-in area. Stone Crest community amenities include a clubhouse, pool, tennis/pickleball courts, playground, and a scenic walking trail around a tranquil pond. With close proximity to AdventHealth, major highways, historic downtown Winter Garden, the West Orange Trail, and top-rated schools, this property provides excellent convenience and connectivity.

Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)

Listing Agent: Joseph Doher (407-203-0007)

Remarks: An exceptional expression of refined living, this luxury estate is nestled within the exclusive gated enclave of Waterside at Johns Lake in Winter Garden. Boasting 5 bedrooms and 5.5 baths, this impeccably designed residence showcases a seamless blend of sophistication and comfort. The expansive open-concept layout is enhanced by elegant wood plank tile flooring throughout the main level and anchored by a chef-inspired gourmet kitchen, thoughtfully appointed for both everyday living and upscale entertaining. The lavish primary suite serves as a private sanctuary, featuring a spa-caliber bath and an oversized walk-in closet designed to impress. Step outside to your own resort-style retreat, where a screened-in pool and spa create the perfect setting for relaxation, complete with a dedicated pool bath for added convenience. The upper level offers a versatile bonus room along with a private guest suite, providing ideal accommodations for visitors or multigenerational living. Distinguished features include a 3-car garage, stately slate tile roof, charming courtyard entry, and a fully integrated irrigation system—every detail curated for both elegance and ease. Residents enjoy access to an array of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, fishing dock, scenic walking paths, parks, and playgrounds. Perfectly positioned just minutes from the charm of Historic Downtown Winter Garden, Winter Garden Village, Hamlin, and Horizon West, with convenient access to major thoroughfares and Central Florida’s premier attractions

Listing is courtesy of: SIERRA REALTY GROUP LLC (407-557-3119)

Listing Agent: Sylvester Harding (407-557-3119)

Remarks: WELCOME to this stunning 4-bedroom, 2.5-bathroom home offering 2,931 square feet of thoughtfully designed living space, perfectly situated on a premium conservation lot across the street from a park, with a green space on the right and overlooking a peaceful and picturesque inlet off Lake Burnett. Framed by majestic oak trees draped in Spanish moss, the setting provides both privacy and breathtaking natural beauty. As you enter, you are greeted by an elegant dining room featuring a custom accent wall, setting the tone for the home’s stylish design. Double doors to the left open into a versatile office or flex space, ideal for working from home or creating a quiet retreat. The entire first floor showcases tile flooring, combining durability with a clean, polished look. Toward the back of the home, the kitchen and great room are perfectly positioned to capture serene views of the screened lanai, the beautifully landscaped yard, tranquil inlet and majestic oak trees. The spacious kitchen features 42-inch cabinets, a large kitchen island, and stainless steel appliances, creating a functional and inviting space ideal for both everyday living and entertaining. The seamless flow into the great room enhances the open-concept design, making it the true heart of the home. Natural light pours in through numerous windows, each enhanced with custom window casings, while crown molding throughout the home adds a refined architectural touch. As you make your way upstairs, you’ll notice decorative wall niches accented with molding that beautifully matches the window casings, adding character and architectural interest to the space. Upstairs, luxury vinyl plank flooring extends seamlessly through the game room as well as all of the bedrooms and closets, offering both style and functionality. The spacious primary suite is a true retreat, complete with a charming bench window seat. The en suite bathroom features a walk-in shower, double vanities, soaking tub, and a generously sized walk-in closet. The additional bedrooms are impressively sized, with two offering walk-in closets, providing ample storage for family and guests. Step outside to enjoy Florida living at its finest on the screened lanai, overlooking the serene inlet and lush landscape. The fully fenced yard features an aluminum fence with gates on both sides, blending security with unobstructed views of the natural surroundings. The exterior has been freshly painted, and the home includes a new water heater, gutters with premium LeafGuard protection, and is pre-wired for a security system for added peace of mind. Located in the highly desirable gated community of Hickory Hammock, residents enjoy resort-style amenities including a swimming pool, sand volleyball court, playground, tennis courts, a 3,600-square-foot clubhouse with catering kitchen and meeting spaces, as well as a community park. This home beautifully combines elegant style, comfort, and a one-of-a-kind setting. Don’t miss the opportunity to make 15665 Citrus Harvest your HOME!

Listing is courtesy of: CARIS REALTY AND INVESTMENTS INC (407-595-0009)

Listing Agent: Janelle Conway (407-595-0009)

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 the 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: 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: Under contract-accepting backup offers. GORGEOUS LAKEFRONT POOL HOME BEING OFFERED IN THE TRANQUIL LAKE COMMUNITY, SANCTUARY AT TWIN WATERS! The home sits on a HALF-ACRE LOT on LAKE AVALON! This 5-bedroom, 4 and 1/2 bath, 4 car garage home has 4,258 heated square feet and 5,916 total square feet. The plan is perfect for MULTIGENERATIONAL LIVING with a guest (in-law) bedroom and ensuite bathroom downstairs; and upstairs the back bedroom has its own ensuite full bathroom. The GOURMET KITCHEN will delight the most avid chef with generous upgraded light gray shaker cabinets including modern hardware and stacked pot drawers for all those cooking gadgets! Sparkling white quartz countertops, meet high-end stainless-steel appliances including a 5-burner gas cooktop, double oven, microwave, refrigerator, and dishwasher. Need lots of organized space in your pantry? No problem-this pantry comes with a professional organizer system including pullouts. You will love gathering around the large coordinating island complete with contrasting navy shaker cabinets, white quartz countertops, stainless farmhouse sink, and counter bar area! The rest of the downstairs living areas (great room, breakfast room, and formal dining room) flow open from the kitchen offering spectacular views of the lake. A pool half bath rests behind the kitchen for easy guest access. You will absolutely love the dedicated and professionally organized laundry room with sink, cabinets, and plenty of folding/hanging areas. Did I mention that the WHOLE HOUSE HAS PLANTATION SHUTTERS and EVERY CLOSET HAS “CALIFORNIA” PROFESSIONAL ORGANIZERS!!! The downstairs living area is covered with light gray, easy to maintain wood looking tile, and soft carpet around the great room TV area. The expansive downstairs primary suite features an extended flex room perfect for an office area, sitting room, or workout area. BOTH primary suite ROOMS LOOK OUT OVER THE salt chlorinated and screened POOL with SPA. Step right out your French doors into the heated spa as you watch the sun set over the lake! You will absolutely love the light, airy primary bathroom complete with free standing soaker tub, huge shower with frameless glass enclosure, and gorgeous white marble-looking porcelain tile covering the floor and shower walls. Light gray cabinets meet medium gray quartz countertops creating a true work of art! Look at the huge, organized closet perfect for all your clothes and accessories! All the bedrooms have a plush carpet for comfort. The upstairs features the bedroom with ensuite bathroom, two other bedrooms that share a bathroom, and a huge bonus room just perfect for game night, movie night, or just chilling as you look out at the lake! The new owner can build a dock on Lake Avalon. Enjoy the pool amenity and Lake Park area just inside the main entrance to the community. Sanctuary at Twin Waters is a convenient location just out from the hustle and bustle, but convenient to all that Winter Garden has to offer including Disney, the charming Downtown Winter Garden with the 20 mile West Orange trail network, Winter Garden Village with its shops and restaurants, and so many other fantastic activities which make this one of the top Central Florida areas to live in. Great local public schools as well as private schools surround the area adding to a great quality of life.

Listing is courtesy of: GALLOWAY REAL ESTATE (407-421-9990)

Listing Agent: Sidney Galloway (407-421-9990)

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)

Remarks: One or more photo(s) has been virtually staged. Paid-off whole-house Solar System! Seller offering RATE BUY-DOWN so Buyer will enjoy lower monthly payments! Closing-Cost Assistance! Nestled on this beautifully remodeled and RECENTLY PAINTED home located on a premier OVERSIZED CORNER LOT within the guard-gated enclave of STONEYBROOK WEST, this stunning 5-bedroom, 3-bathroom residence offers the ultimate Winter Garden lifestyle. The home has been meticulously enhanced with MODERN UPDATES, ensuring a MOVE-IN-READY experience for today’s discerning buyer. SAVE ON UTILITY BILLS WITH THE WHOLE HOUSE SOLAR SYSTEM AND ELECTRIC CAR CHARGER. Inside, the open-concept layout is anchored by a SPACIOUS KITCHEN featuring quartz countertops, a central island, and HIGH-END STAINLESS STEEL APPLIANCES, all flowing into a spacious family room warmed by a classic fireplace. High-volume ceilings—reaching 9.25 feet on the main floor and an impressive 10.50 feet in the massive upstairs bonus room—create an airy, grand atmosphere throughout. The well-appointed laundry room includes a GE ULTRA WASHER AND DRYER, along with a STAINLESS STEEL UTILITY SINK for added convenience. The garage is equally impressive, featuring a heavy-duty Husky organizational system that provides exceptional storage and functionality. Retreat to the primary suite, where tray ceilings and a private walk-out balcony offer a peaceful vantage point overlooking the championship golf course. The lifestyle here extends far beyond the front door. Stoneybrook West is a premier “live-play” community boasting 24-hour staffed security and a spectacular waterfront clubhouse perched on the shores of Black Lake. For the outdoor enthusiast, the amenities are unmatched: enjoy private lake access via a community boat ramp and the rare convenience of an on-site boat storage lot. Whether you are hitting the links on the championship golf course, working out in the fitness center, or relaxing at the resort-style pool, every day feels like a vacation. Perfectly positioned for convenience, you are just 6 minutes from Winter Garden Village, 18 minutes from Walt Disney World, and only 30 minutes from Orlando International Airport. This home combines the security of a gated community, the luxury of recent high-end improvements, and the rare perk of Florida lake living. Call today to schedule your private showing!

Listing is courtesy of: EXP REALTY LLC (407-706-5000)

Listing Agent: Daniel Betancourt (407-375-9142)

Remarks: Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Introducing the exquisite Roseland former model home! This stunning 5-bedroom, 5-bathroom, 2-car garage masterpiece boasts a homesite neighboring a pond and a luxury pool, spa, and outdoor kitchen. As you step through the double entry glass doors, you are immediately greeted by a striking foyer that rises to the second floor, setting the tone for the entire home. To one side, an enclosed flex room offers versatility, while the formal dining room invites effortless entertaining. As you travel further into the Roseland you are greeted by a grand staircase, featuring engineered hard wood plank treads and wrought iron balusters with an oak handrail. Tucked just under the staircase is a wine lover’s dream, a wine cave with built-in cabinets, quartz countertops, and stylish tile backsplash. From there, you enter the heart of the home—the open concept kitchen and living area. Equipped with built-in Whirlpool stainless steel appliances, including a beverage cooler, double oven, and built-in cooktop, the kitchen is a dream for culinary enthusiasts. Two-tone soft-close cabinetry is paired with exquisite quartz countertops, creating a timeless and sophisticated look, while a spacious walk-in pantry ensures ample storage. The open-concept design effortlessly connects the kitchen to the gathering room and cafe, where soaring ceilings create an airy, light-filled space, perfect for both intimate gatherings and larger celebrations. Step outside to the covered lanai and enjoy your backyard oasis complete with an inground pool and spa, as well as an outdoor kitchen. Also located on the first floor, is a “Multi-Gen Suite” offering a spacious bedroom with its own linen closet, walk-in closet, and attached bathroom complete with a frameless glass enclosed shower and quartz countertops. Upstairs, the private owner’s suite spans one side of the home, creating a peaceful retreat. The owner’s retreat area, ideal for reading or unwinding, leads into the spa-inspired owner’s bath, where luxury knows no bounds. A free-standing bathtub, frameless glass-enclosed shower, enclosed toilet, and double walk-in closets create a sanctuary of relaxation. The second floor also offers two additional spacious bedrooms connected by a Jack and Jill bathroom, ensuring both privacy and convenience, while a third bedroom enjoys its own en suite bath, providing an added level of comfort and luxury. The upstairs laundry room, with a utility sink trimmed in quartz and cabinets, makes daily tasks a breeze. With an intelligently designed layout and meticulously curated finishes, this home offers the perfect balance of form, function, and style. It's the epitome of luxury living in a highly sought-after location, blending convenience, sophistication, and thoughtful design into a living experience like no other. Schedule a tour today!

Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)

Listing Agent: Adrienne Escott (407-250-9131)

Remarks: Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Step into the Imperial, where luxury and convenience seamlessly combine to create a truly elevated living experience. This remarkable 5-bedroom, 3.5-bathroom former model home with a 2-car garage situated on a conservation view homesite offers unparalleled craftsmanship and thoughtful design throughout. The open-concept layout flows effortlessly, creating an expansive, airy feel that exudes both sophistication and comfort. On the first floor, discover a private en suite bedroom with a walk-in closet and elegant quartz countertops—a perfect retreat for guests. At the heart of the home, the chef-inspired kitchen is a true masterpiece, featuring Winstead Quill cabinetry, striking quartz countertops and a decorative tile backsplash. Built-in Whirlpool stainless steel appliances, including a refrigerator and natural gas cooktop, make cooking a pleasure. The kitchen seamlessly connects to the café and gathering room, where a sliding glass door opens to the covered lanai, featuring an outdoor kitchen that enhances indoor-outdoor living. Beyond the covered lanai, the backyard offers a relaxing fireplace with a waterfall feature on either side, all overlooking tranquil conservation views. The first floor also offers a convenient powder room, perfect for guests, as well as a bedroom with an attached bathroom. Upstairs, the luxurious owner’s suite is a private sanctuary, featuring a spacious walk-in closet (in a built-in closet system) and a spa-like en suite bathroom with quartz-topped dual vanity sinks and a frameless glass enclosed shower. The loft area provides the perfect space to unwind, while three additional bedrooms and another bathroom complete the upper level. For added convenience, a thoughtfully located upstairs laundry room simplifies everyday tasks. Beautiful wood-look tile flooring is found throughout the first floor, laundry room, and bathrooms, while plush, stain-resistant carpet complements the loft and bedrooms. Designer-curated finishes elevate every corner of this home, including thoughtfully placed rain gutters, matte black plumbing fixtures and hardware, built-in drop zone, comfort height toilets, Whirlpool washer and dryer, and wood-look luxury vinyl plank treads and risers at the staircase. This home is equipped with a smart thermostat, video doorbell, LED down lights, digital IP camera pre-wire, surround sound pre-wire, smart irrigation control, and smart door lock and garage door opener ensuring your home is as connected as it is beautiful. This home offers the perfect combination of luxury, convenience, and modern design—an ideal place to live and relax. Schedule a tour today!

Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)

Listing Agent: Adrienne Escott (407-250-9131)

Remarks: Under contract-accepting backup offers. Stunning lake-view home in Waterside at Johns Lake, overlooking Lake Avalon in Winter Garden! This spacious 5-bedroom, 3-bath residence offers 3,196 sq ft of open-concept living with a desirable downstairs primary suite featuring a spacious, well-appointed bathroom along with a customized walk-in closet. A second downstairs bedroom is paired with a beautifully RECENTLY renovated full bath showcasing a newly upgraded walk-in shower—ideal for guests or multi-generational living. Step inside to a welcoming entry that opens to a versatile sitting area—perfect for a home office or library—leading into a large family room, dining area, and well-appointed kitchen with natural gas range—perfect for entertaining. Enjoy the clean, modern feel of a completely carpet-free interior with durable vinyl flooring throughout the main living areas. The highlight of this home is the oversized screened lanai, perfectly positioned to capture serene Lake Avalon views—an ideal space for morning coffee, outdoor dining, or relaxing sunset evenings. Upstairs features a versatile loft, three additional bedrooms, and a full bath. Residents of Waterside at Johns Lake enjoy resort-style amenities including a lakeside pool, clubhouse, fitness center, scenic walking trails, playground, and community dock. Conveniently located just minutes from Winter Garden Village with easy access to 429, Florida’s Turnpike, downtown Orlando, theme parks, and Orlando International Airport.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Rema Perras (802-233-5292)