Homes for Sale Near West Orange High in Winter Garden - 175 homes

Remarks: Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Palmetto floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open-concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, quartz countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.

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

Listing Agent: Tatiana Souza (407-467-9914)

Remarks: Under Construction. Under Construction. Welcome to Lakeview Village Estates, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Cypress floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open- concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, striking Calacatta countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.

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

Listing Agent: Tatiana Souza (407-467-9914)

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 a former model home, there is also an option to purchase the furniture separately. 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: BEAUTIFUL HOME… AMAZING OPPORTUNITY… THIS HOME IS A MUST SEE!!! Welcome to this stunning one-story residence offering 4 spacious bedrooms and 3 full baths, perfectly designed for both comfort and style. From the moment you step inside, you’ll be greeted by hardwood floors and soaring high ceilings throughout—with NO CARPET—creating a bright, open, and inviting atmosphere. The heart of the home is the grand open-concept living area, ideal for entertaining. The gourmet kitchen boasts a large island-style breakfast bar with beautiful granite countertops, a stylish modern backsplash, stainless steel appliances, a double oven, and a walk-in pantry. Seamlessly flowing into the family room and dining area, this space is perfect for hosting gatherings or enjoying cozy nights in. Step outside to your very own sparkling private backyard oasis, complete with a screened lanai—ideal for relaxing, dining al fresco, or enjoying Florida’s sunny lifestyle year-round. The luxurious owner’s suite features high ceilings, a spa-inspired bath with a soaker tub, his-and-hers vanities, an oversized walk-in shower, and an expansive walk-in closet that will exceed expectations. A front room with 15-foot ceilings offers flexibility as a bedroom, office, yoga or art studio, playroom, or game room—tailored to fit your lifestyle. Location, Location, Location! Just minutes from Winter Garden Village, you’ll enjoy premier shopping, dining, and year-round community events. Only a mile away is the vibrant Downtown Historic Winter Garden, home to the ever-popular Farmer’s Market, unique boutiques, and the scenic West Orange Trail for walking, biking, and jogging. Easy access to major commuter routes ensures convenience while preserving the charm of this highly desirable area. ? This home offers the perfect blend of luxury, functionality, and location. Don’t miss the chance to make it yours—schedule your private showing today!

Listing is courtesy of: LEGACY PLUS REALTY (407-992-2268)

Listing Agent: Solon Potenciano Silva (407-760-5141)

Remarks: This first-floor condo in the gated Southern Pines community offers 1,216 square feet of well-designed living space with an open floor plan, private outdoor area, and two full bathrooms. Making it a strong fit for first-time buyers, down-sizers, or investors. The layout connects the living area directly to the outdoor space, and both bedrooms provide solid closet storage. The kitchen offers ample counter space and cabinetry for everyday living. Southern Pines residents enjoy access to a pool and spa, fitness center, indoor basketball and racquetball courts, tennis and pickleball courts, a media room, billiards lounge, business center, BBQ area, car wash station, and playground. All within a secure, gated community. Located minutes from the West Orange Trail, Johns Lake, SR 408, and the Florida Turnpike, with top-rated Orange County schools nearby and Orlando International Airport 23 miles away. Winter Garden’s dining and retail corridors are within easy reach. Low-maintenance living with resort-style amenities in a location that works. Schedule your showing today.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Brendan Morales (407-881-4633)

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. Meticulously updated and move-in ready, this stunning residence is located in the highly sought-after gated community of Waterside in Winter Garden. Designed with both luxury and functionality in mind, the home features a desirable first-floor primary suite boasting an expansive en-suite bath with dual sinks and two custom-organized walk-in closets. The main level also includes a guest bedroom with its own full bath, a private office/den, and a convenient powder room. The second floor is an entertainer's dream, offering a massive loft, a Jack-and-Jill suite, and an additional bedroom with a private full bath. Significant upgrades abound, including new dual AC units (2024), rich hardwood flooring (2019), and a modern electric fireplace. Premium features include plantation shutters, custom shelving in the pantry and primary closets, a whole-house water purification system, and noise-blocking insulation for ultimate serenity. Outdoor and tech upgrades feature an extended driveway and an installed Tesla charger. Residents enjoy resort-style amenities including a community pool, fitness center, and clubhouse. Perfectly situated on a prime lot, you are minutes from Winter Garden Village, major highways, and premier shopping and dining. This could be your perfect dream home—schedule your private tour today!

Listing is courtesy of: ONE STOP SERVICE REALTY INC (407-739-3196)

Listing Agent: Ye Kang (321-279-1059)

Remarks: Under contract-accepting backup offers. Luxury At its Finest. This Beautiful Immaculate Open Concept 4 bedrooms, 4 baths residence featuring a spacious loft with a full bath. Loft on 2 nd Floor can potentially be used as a 5th bedroom. Ideal for guests retreat, home office, media lounge, media room or additional entertainment for the entire family. The Amazing Gourmet Chefs kitchen with under cabinet lighting Gas stove, double oven showcases an extra large extended island perfect for entertaining. Complemented by elegant finishes. Open concept living spaces and exceptional comfort throughout the home in its entirety. French Doors gives access to the resort style pool with 4 therapy jets, bubblers on the sun shelf, custom hand rail with multi led lights with a Wet Edge Pool Interior. Elegant Pavers. The Pool is 3 ft on the shallow end and 6 ft on the deep end and measures 15 x 31. This home is taken care with lots of Pride and Tender Loving care. This home sits on a corner Lot with lots of privacy for all entertainment and relaxation. Garage has overhead racks for extra storage. This is a very small community that is peaceful and tranquil for great evening walks. By Appointment Only. Thank You.

Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)

Listing Agent: Tracy Hampstead (407-803-3137)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath home located in the highly desirable gated golf community of Stoneybrook West in Winter Garden. This move-in-ready residence features an open and spacious floor plan with separate living and dining areas, high ceilings, abundant natural light, and ceramic tile throughout. The upgraded kitchen offers granite countertops, ample cabinet space, and all appliances are included. The spacious primary suite features a large walk-in closet and an updated bathroom with skylights, dual vanities, a garden tub, and a separate shower. Enjoy outdoor living in the fully fenced backyard with a large patio, perfect for entertaining or relaxing. Recent updates and meticulous care make this home a true standout. Roof replaced in 2021. Property comes with solar panels. Residents enjoy resort-style amenities including a community pool, fitness center, tennis and basketball courts, playgrounds, lake access, fishing pier, boating, and 24-hour guarded gate security. Conveniently located near top-rated schools, shopping, dining, major highways, downtown Winter Garden, and Orlando's world-famous attractions. Don't miss this exceptional opportunity—schedule your private showing today!

Listing is courtesy of: REALTY ONE GROUP EVOLUTION (786-477-4715)

Listing Agent: Milena Nunez (407-247-1814)

Remarks: An unparalleled lakefront opportunity in Downtown Winter Garden **Seize the rare chance to own a premier waterfront estate where the true value lies in the spectacular lot, private dock, and an enviable golf-cart lifestyle ** Launch your boat from your private lift for a scenic 30-minute cruise to Mt. Dora or take your golf cart just minutes away to the historic downtown Farmers’ Market and restaurants **Positioned within a private, gated enclave directly across from the West Orange Trail, this property offers the ultimate Florida resort lifestyle outside, featuring a heated saltwater pool, raised spa, and a fully fenced, expansive lakeside yard ** Inside, the home boasts a massive primary suite +/16x26’ with tray ceiling, fireplace and a balcony with lovely lake views and massive +/-23x25 bonus room including a wet bar and fireplace** The kitchen has a large cooking island w/sink plus a separate breakfast bar, stone counters, under cabinet lighting, a Jenn-Air double convection oven and lovely dining area overlooking the lake ** There's even an open wine closet/alcove with wine refrigerator off the kitchen ** First floor bedroom with an oversized walk in closet as a 5th bedroom or den (currently being used as a dining room) ** Other home upgrades include a newer roof +/-2022, 3 newer A/C units, a whole-home Katolight 40KW generator that runs +/- 90% of the home, crown molding throughout the home, ADT security system with cameras, boat house with new roof 2025, resurfaced pool +/-5 yrs ago & Aqualink pool/spa automation system and a 10’ seawall ** Relax on the covered screened patio with the Bose speaker system and prime outdoor living space including additional yard space beyond the pool and patio ** 2 car garage plus a 1 car garage with easy access to the back yard perfect for bringing your boat or lawn equipment through ** LOW HOA fees $200 quarterly ** All room measurements in MLS and on 3d floorplan are approximate. Buyer to verify. Tax record is incorrect - property has 5 bedrooms. Dock measurement is estimated. Buyer to verify. Solar panel lease to be transferred to buyer at closing.

Listing is courtesy of: INDEPENDENCE REALTY GROUP LLC (407-408-6662)

Listing Agent: Andrew Philippone (407-408-6662)

Remarks: Welcome to this amazing unit, nestled within the gated community of Southern Pines in the sought after area of Winter Garden , Florida; this beautiful 3 bedrooms 2 bathrooms condo is located in the second floor and has an open concept kitchen with a Dinning- living combo area, also an additional space for an office or a play area , the unit also has a split bedroom plan , with a spacious primary bedroom and an ensuite, also two additional bedroom at the other side of the unit, with an additional full bathroom . This incredible community has a so much in amenities; a real lifestyle for the residents , such as community pool and spa , a very well equipped fitness center, a club house with many areas for family entertainment, tennis court, playground, a car wash area and an indoor basketball / racquetball court. This condominium is located a short drive from the Winter Garden Village shopping area , as well as Downtown Winter garden, with easy access to all main Highways making the commute easier. The Disney World parks are just 9 miles away; this community is definitely a place where families will experience great enjoyment; don't miss the chance to call this unit your NEW HOME!!

Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)

Listing Agent: Libia Rodriguez (407-952-7069)

Remarks: One or more photo(s) has been virtually staged. SEVERAL PHOTOS HAVE BEEN VIRTUALLY STAGED !Welcome to this beautifully updated 4-bedroom, 2.5-bath home in the highly sought-after Regency Oaks community. Thoughtfully upgraded for long-term peace of mind, this residence features a newly replaced roof, a 2023 HVAC system (both indoor and outdoor units), and a 2023 water heater—major improvements that add exceptional value and confidence for the next owner. Step inside to discover a bright, open floor plan with luxury vinyl flooring throughout, offering durability, modern style, and easy maintenance. The remodeled kitchen showcases sleek modern cabinetry and quartz countertops, creating a fresh, contemporary space perfect for everyday living and entertaining. The spacious primary suite provides a comfortable retreat, complemented by three additional bedrooms ideal for family, guests, or a home office. With two full bathrooms and a convenient half bath, the layout is designed for both functionality and comfort. Enjoy Florida living at its best with a screen-enclosed patio and a fully paved backyard, offering a low-maintenance outdoor oasis perfect for gatherings, grilling, or quiet relaxation. Located just 15 minutes from Universal Studios and Disney Parks and less than a 2-minute walk to AdventHealth, this home is perfectly positioned for both families and professionals. Regency Oaks offers resort-style amenities including a sparkling pool, clubhouse, tennis courts, playground, and a scenic park—enhancing the lifestyle experience beyond your front door. This move-in-ready home combines modern upgrades, unbeatable convenience, and exceptional community features—an outstanding opportunity to enjoy the best of Winter Garden and Orlando living.

Listing is courtesy of: PMI PRIME HOME (407-218-7598)

Listing Agent: Jianlin Shi (407-988-5057)

Remarks: Under contract-accepting backup offers. Welcome to luxury lakefront living on the shores of sought-after Johns Lake. Perfectly positioned with breathtaking west-facing sunset views, this fully upgraded waterfront residence offers the ultimate blend of elegance, comfort, and resort-style outdoor living in one of Winter Garden’s most desirable communities. Featuring nearly 3,500 square feet on 1 floor of thoughtfully designed living space, this exceptional home showcases 4 bedrooms, 3.5 bathrooms, a 3-car garage, premium hardwood flooring, and a gourmet chef’s kitchen with high-end finishes, upgraded cabinetry, and expansive entertaining space. Designed to maximize the waterfront lifestyle, the home seamlessly transitions outdoors to a private backyard retreat complete with a sparkling pool, oversized spa, outdoor kitchen, and stunning panoramic lake views — the perfect setting for sunset entertaining year-round. Additional highlights include a newer roof and HVAC systems (approximately 3 and 5 years old), luxurious updated interiors, spacious living areas. This rare Johns Lake opportunity combines elevated style with effortless move-in-ready convenience. With premium designer furnishings negotiable. Making this a possible true turnkey opportunity. Located within the highly sought-after Johns Lake Pointe community, residents enjoy proximity to historic downtown Winter Garden, top-rated schools, shopping, dining, major highways, and Orlando’s world-class attractions. Experience the best of Central Florida lakefront living in a home where every evening ends with unforgettable sunsets over Johns Lake.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Carlos Facchinat (407-433-8109)

Remarks: Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Julie Bettosini, Pa (321-689-9594)

Remarks: Welcome home to this beautifully maintained 4-bedroom, 3 full bath, residence in sought-after Twinwaters. Featuring a designer kitchen with full-extension soft-close drawers and cabinets, 10-foot ceilings on the main level, 9-foot ceilings upstairs, crown molding, and central vacuum, this home offers both comfort and thoughtful upgrades throughout. Enjoy peaceful views of the expansive conservation area from your backyard with no rear neighbors, creating a private and relaxing setting. Professionally designed landscaping provides year-round color and fragrance, while local songbirds add to the natural charm. On clear evenings, catch a glimpse of Disney fireworks from home. Conveniently located just minutes from historic Downtown Winter Garden, shopping, dining, and premier golf destinations including Orange County National. Complete with a spacious 2-car garage, this warm and inviting home is ready for its next owner. Schedule your private showing today!

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

Listing Agent: Jennifer Dollar (407-252-3762)

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: 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: Experience the ultimate in luxury urban living at 68 N Park Ave, a stunning 3-story townhome with rooftop deck located in the heart of Historic Downtown Winter Garden. This sophisticated 4-bedroom, 4.5-bathroom residence offers over 3,500 sq. ft. of meticulously designed space, seamlessly blending modern elegance with the charm of the historic district. The open-concept main level features soaring 11-foot ceilings, expansive industrial-style windows, and a chef’s dream kitchen equipped with an oversized quartz island, natural gas appliances, and custom artisan cabinetry. Accessibility is effortless with your own private elevator serving all floors. Retreat to the third-floor master suite, featuring a spa-inspired bath and massive walk-in closet, or host guests in the versatile first-floor bedroom suite. The "wow factor" continues on the 1,200 sq. ft. private rooftop terrace, offering panoramic views of the city skyline—the perfect spot for evening cocktails or watching local fireworks.Location is everything. Leave your car in the 2-car garage and embrace the golf-cart-friendly lifestyle. You are just steps away from: The award-winning Winter Garden Farmers Market, The vibrant Plant Street Market and Crooked Can Brewing Co, The world-class West Orange Trail for biking and running, Boutique shopping, fine dining, and the historic Garden Theatre. Don’t miss this rare opportunity to own a piece of downtown luxury. Schedule your private showing today!

Listing is courtesy of: VISTA CAY REALTY COMPANY (407-996-4656)

Listing Agent: Mauro Costa (321-231-6800)

Remarks: Don’t miss this great investment opportunity in the heart of Winter Garden. This 2-bedroom, 2-bath condo offers laminated floors and is already rented, generating income from day one. Home features updated plumbing with a complete repipe. Located just minutes from Downtown Winter Garden, with easy access to restaurants, shops, parks, and major highways. Not a gated community, offering easy access and low-maintenance living. Perfect for investors seeking a stable, income-producing property.

Listing is courtesy of: ROMAN'S PRO REALTY LLC (407-610-1970)

Listing Agent: Maria Perez (407-496-2336)

Remarks: **We've just introduced a significant price reduction, creating an exceptional opportunity for new owners. ** **Welcome to Golf Cart Life in Historic Downtown Winter Garden** Nestled within Stanton Estates — an exclusive enclave of just 45 luxury homes — this contemporary masterpiece places you in the heart of **Winter Garden’s vibrant Golf Cart District**, where every day feels like a getaway. Built in 2018, this one-story multigenerational estate offers 3,170 sq ft of refined living on a nearly 1/3-acre lot, just a quick golf cart ride from **Plant Street’s award-winning restaurants, live music, boutique shops, the famous Saturday Farmer’s Market, the Crooked Can Brewery, and the scenic West Orange Trail**. Take a look at Virtual Tour Link 2 to see all the exciting and fun things available to you in the downtown and historic area of Winter Garden. Inside, soaring 12-ft ceilings and natural light flow through an open, flexible layout with four bedrooms, four full baths, and a private office. The gourmet kitchen anchors the home with solid wood cabinetry, quartz countertops, an oversized island, walk-in pantry, and a full suite of KitchenAid Professional appliances with natural gas. The primary suite features a recessed ceiling, expansive custom walk-in closet, and a spa-inspired bath. Fully retractable sliders open to a covered lanai surrounded by mature, professionally designed landscaping and privacy fencing — your own private Florida retreat after a day of exploring downtown. Premium upgrades include smart-home technology, motorized shades, whole-home water filtration, 8-ft solid core doors, custom cabinetry, a three-car tandem garage with brick paver driveway, and a brand-new tankless gas water heater (2025). Just minutes from Disney, Universal, and SeaWorld, with seamless access to SR-429, the Turnpike, and 408, this address blends luxury living with the unbeatable charm and excitement of Downtown Winter Garden. Opportunities like this in Stanton Estates are rare. **Welcome to the lifestyle everyone wants**

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

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