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241 N Dillard Street, Winter Garden
$1,499,999
4 Beds ⋅ 3 Baths ⋅ J L Dillard Sub 3 SubDv. ⋅ 34787 Zip Code
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.

241 N Dillard Street, Winter Garden
330 Southern Pecan Circle Unit 208, Winter Garden
$298,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
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!!

330 Southern Pecan Circle Unit 208, Winter Garden
15695 Grove Resort Avenue Unit 4417, Winter Garden
$150,000
1 Baths ⋅ Grove Resort & Spa Hotel Condo Iv SubDv. ⋅ 34787 Zip Code
Enjoy this Beautiful Studio Condo within The Terraces at the Grove Resort & Water Park, the property has enough amenities that you wouldn't have to leave BUT Disney World is minutes away. The property boast a private retreat with Boutique/Hotel accommodations. As an Owner or a Guest you will enjoy the SURFING WATER PARK, WAVE POOL, FITNESS STUDIO, MIMI MARKET, SECLUDED INFINITY POOL with a Poolside Bar for Cocktails and/or Light Bites. AND IF THAT ISN'T ENOUGH YOU HAVE A FITNESS CENTER, PARK PLAYGROUND, RACQUET BALL, TENNIS COURTS .FISHING, PRIVATE BOAT RAMP. Also minutes from Shopping, Restaurants, Golfing. As a Vacation Resort for yourself or a vacation rental, it is all stress free.

15695 Grove Resort Avenue Unit 4417, Winter Garden
14501 Grove Resort Avenue Unit 2334, Winter Garden
$274,900
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium 2 SubDv. ⋅ 34787 Zip Code
Escape to your own luxurious, fully furnished condo-hotel residence at the prestigious Grove Resort & Water Park—just minutes from Walt Disney World. Designed for both personal enjoyment and investment, this exceptional unit offers the perfect combination of a turnkey vacation retreat and high-performing income asset. Located on the third floor of Condominium II, the sought-after Jasmine floor plan boasts an open-concept living area filled with natural light, a modern kitchen with stainless steel appliances, sleek countertops, and the convenience of in-unit laundry. Step out onto the extended screened balcony to enjoy tranquil resort and conservation views—an ideal space for morning coffee or evening relaxation. As an owner, you and your guests will experience resort living at its finest. The Surfari Water Park features a thrilling lazy river, water slides, and the FlowRider surf simulator. Multiple heated pools, hot tubs, and private cabanas create endless opportunities for relaxation, while children will love the splash zones, game arcade, and dedicated play areas. Beyond the water attractions, the resort offers on-site restaurants and bars, a grocery café, full-service spa, fitness center, mini-golf, boat rentals, and 24-hour concierge services—all within a secure, award-winning community. This unit is part of the professionally managed hotel rental program, offering truly hands-free ownership. With full-service management covering marketing, bookings, housekeeping, and maintenance, owners can enjoy strong cash-flow potential while eliminating the stress of day-to-day operations. Whether you’re looking for a private getaway near Orlando’s top attractions or a proven income-producing property, this Grove Resort condo presents an unmatched opportunity. Experience luxury, convenience, and investment potential in one of Central Florida’s premier resort communities. Schedule your private tour today!

14501 Grove Resort Avenue Unit 2334, Winter Garden
10007 Little Alcove Loop, Winter Garden
$960,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Stunning Emerald serie house, Selden model built in 2018 well maintained, featuring 4 bedrooms, 3.5 bathrooms, and approximately 2,920 sq ft of living space. Situated on a premium corner lot of about 10,585 sq ft, this home offers a 3-car tandem garage, spacious backyard, private wooded views, and a screen-enclosed private pool—perfect for year-round Florida living. The open-concept design includes a formal dining room, elegant foyer with wrought-iron staircase, and a gourmet kitchen with a large island, 42” cabinets with crown molding, granite countertops, stainless steel appliances, and a convenient drop zone from the garage. The owner’s suite boasts a tray ceiling, a spa-like en-suite bathroom with dual sinks, a garden tub, and a spacious walk-in closet. Additional features include a durable concrete tile roof, dual A/C units, and numerous upgrades: exterior lighting, sealed paver driveway and porch, landscape lighting, decorative stonework, epoxy-finished garage floor, and professional landscaping. Lawn care is included with HOA fee. Located in the highly sought-after Waterleigh community in Winter Garden, residents enjoy resort-style amenities: two community clubhouses, 4 resort-style pools, 2 fitness center, beach volleyball, 2 tennis courts, mini-golf, community garden, dog park, fishing pier, and scenic walking/biking trails. The neighborhood is beautifully landscaped with lakes, green spaces, and planned community events. Conveniently located just minutes from Historic Downtown Winter Garden, Winter Garden Village, and easy access to SR-429 for a quick commute to Orlando and Walt Disney World. Zoned for top-rated schools: Atwater bay Elementary, Water Spring Middle, and Horizon High School.

10007 Little Alcove Loop, Winter Garden
13377 Lake Butler Boulevard, Winter Garden
$5,995,000
5 Beds ⋅ 6 Baths ⋅ 34787 Zip Code
Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural zoning designation). Very quiet. Very private. No HOA and close to Winter Garden and Windermere amenities as well as all theme parks.

13377 Lake Butler Boulevard, Winter Garden
9493 Emerald Berry Drive, Winter Garden
$989,000
4 Beds ⋅ 4 Baths ⋅ Summerlake Reserve SubDv. ⋅ 34787 Zip Code
We present an impeccable, newly built home in brand-new condition, ready to welcome you and your family with comfort, modernity, and style. Located in the sought-after Summerlake Reserve community in Horizon West, this home surprises with every detail. Upon arrival, the charming porch with its well-kept garden gives you a taste of what lies ahead. Upon entering, the integrated living, dining, and kitchen areas create a feeling of spaciousness and warmth, perfect for those who value open, well-lit spaces. Large sliding doors allow for abundant natural light and connect the interior with the exterior. With high ceilings of almost 3 meters, the home exudes elegance and sophistication. The kitchen is a true highlight: equipped with modern appliances, high-end wood cabinetry, a large central island, and a spacious pantry—ideal for those who love cooking and entertaining. The four bedrooms are spacious, well-appointed, and designed to offer maximum comfort. There are three and a half bathrooms, all with quality finishes and tasteful furnishings. The laundry room offers a functional space and is already equipped to make daily life easier. The garage accommodates three cars and has an automatic gate, ensuring convenience and security. All this in a prime location, close to schools, shops, restaurants, and all the amenities that make Horizon West one of the most valued areas in Florida. If you're looking for a new, modern home in a complete community, this is the perfect opportunity. Schedule your visit and come see for yourself!

9493 Emerald Berry Drive, Winter Garden
14501 Grove Resort Avenue Unit 2129, Winter Garden
$359,000
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel SubDv. ⋅ 34787 Zip Code
HUGE PRICE REDUCTION! Don’t miss this rare opportunity to own a fully furnished, turn-key 3-bedroom, 2-bath resort condo at the world-famous Grove Resort & Water Park, just minutes from Disney. Located in Building 2, Unit #2129 offers tranquil conservation views from your private balcony and quick access to the resort’s incredible amenities. Whether you’re seeking a personal vacation retreat or a hands-free income-producing property, this condo delivers both. With a proven rental history and participation in the professionally managed short-term rental program, you can generate income seamlessly when you’re not here. Guests can enjoy the Surfari Water Park, multiple pools, spa, fitness center, restaurants, lakefront pier, and more—completely worry-free. Act quickly—this unit is a guest favorite, showings are limited, and opportunities like this don’t last.

14501 Grove Resort Avenue Unit 2129, Winter Garden
9940 Black Bear Lane, Winter Garden
$2,050,000
4 Beds ⋅ 5 Baths ⋅ Acreage & Unrec SubDv. ⋅ 34787 Zip Code
Pre-Construction. To be built. This Custom Single-Story Modern Farmhouse by Lionshead Homes is a showstopper! Set on a serene 5-acre private oasis. Plenty of space for farm animals or just enjoy the open space and tranquil surroundings. Lionshead Homes has recently built custom homes near this property. So Buyers may view a recently completed home to get an idea of fit and finish and our quality craftmanship. Located in the Avalon Rural Settlement, you'll enjoy the country lifestyle without sacrificing proximity to shopping, entertainment and the suburban lifestyle of Hamlin and Winter Garden. Call for more information or to schedule a viewing appointment.

9940 Black Bear Lane, Winter Garden
11162 Hanlon Terrace Alley, Winter Garden
$445,000
3 Beds ⋅ 3 Baths ⋅ K Hovnanian Winding Bay Preserve SubDv. ⋅ 34787 Zip Code
**Stunning Home in Winding Bay Preserve with Resort-Style Amenities** Discover your dream home in the sought-after Winding Bay Preserve! This immaculate residence offers resort-style living with a wealth of community amenities, including a sparkling pool, oversized cabana, tot lot, dog park, and fitness park—ensuring year-round fun for everyone. The home's open floor plan is bathed in natural light, creating a warm and inviting space that's perfect for entertaining. The kitchen is a chef's delight, featuring stainless-steel appliances, quartz countertops, and elegant light cabinetry. Conveniently located just 10 minutes south of the Hamlin area, you'll enjoy easy access to premier shopping, dining, and a state-of-the-art movie theater. Experience luxury, comfort, and convenience—all in one place!

11162 Hanlon Terrace Alley, Winter Garden
18 & 20 E Plant Street, Winter Garden
$2,999,000
Fries Winter Garden SubDv. ⋅ 34787 Zip Code
COMMERCIAL property in downtown WINTER GARDEN! Located directly on PLANT STREET in the Historic District Overlay this property offers great exposure. It is currently zoned C-1 and has many permitted uses such as retail establishments, eating and drinking establishments, office & studios, financial institutions, private club, personal service, church and more. Permitted use list available upon request. Total property consist of over 3300 square feet and almost 2700 square feet of interior space. Property is split up unit two units. The first unit is approximately 1050 interior space offering a main retail area measuring 25x22, an office 9x14 and additional room 18x8. There is additional walkway space and two restrooms. The second unit is approximately 2050 interior space offering a 31x14 retail space, and additional spaces measuring 6x14, 8x12,10x17,18x24 and 7x15. There is additional walkway space and one restroom plus rear entrance/exit ability. ENJOY the downtown Winter Garden life.

18 & 20 E Plant Street, Winter Garden
18339 Oliver Twist Way, Winter Garden
$650,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code
Short Sale. *Motivated Seller* This 2023 built home has only had One-owner, highly upgraded luxury 4-bedroom, 3-bathroom home with 2-car garage, fenced-in oversized yard, and overhead storage in the highly desirable Waterleigh community—just minutes from Walt Disney World in the Top-Rated School zone. No lawn mower needed - the HOA maintains all lawn care in this beautiful community! This home is constructed Block on Block - top and bottom unlike many other builders who build wood frame on the second floor. Don't wait for a newly constructed home and pay more for a similar home... this one is ready now. This well-appointed home features a downstairs guest suite, upgraded wood-look tile (no carpet on the first floor), and a gourmet kitchen with 42” cabinets, quartz countertops, custom backsplash, large island, under-cabinet lighting, and premium LG stainless steel appliances, including a French door refrigerator with craft ice and Instaview. Additional features include an EV charging station, smart switches, custom lighting and fans throughout, and a covered lanai overlooking a spacious backyard. Upstairs offers a generous loft, two secondary bedrooms with walk-in closets, a full bathroom with dual sinks, a laundry room with LG washer and dryer on pedestals, and a luxurious primary suite with a tray ceiling, a spa-style bath, a frameless glass shower, a soaking tub, and an oversized walk-in closet. Oversized yard has plenty of space to build your own pool or you could enjoy the Waterleigh resort-style amenities with 3 pools, clubhouses, fitness centers, tennis courts, dog parks, playgrounds, putt-putt golf, fishing pier, walking trails, rock climbing, pickleball ball and a full calendar of social events. Just a couple of streets away, the 4th pool is under construction and will be completed shortly. Zoned for top-rated schools and offering convenient access to 429, 417, and 408. Many homeowners enjoy golf cart living in this community, where you can enjoy an abundance of amenities, social events, drop your little ones off at school, or do your grocery shopping; there's a daycare, elementary, and middle school, and a Publix located inside the community. This is a rare opportunity to own a move-in-ready, upgraded home in one of Winter Garden’s most popular neighborhoods!

18339 Oliver Twist Way, Winter Garden
120 S Dillard Street, Winter Garden
$160,000
. SubDv. ⋅ 34787 Zip Code
Business for Sale Only - Exceptional opportunity to own a well-established beauty Salon in the heart of Winter Garden. Great Located. This Beauty Salon offers unbeatable visibility and foot traffic, making it a high-demand business with strong revenue potential. Key Features: Turnkey Operation: Fully equipped with modern chairs, mirrors, workstations, and a reception area. High-traffic, constant flow of customers. Established Clientele: has built a solid reputation and loyal customer base. This business is perfect for an owner-operator or an investor looking to step into a thriving market with significant foot traffic. With its prime location and steady clientele, this is poised for continued growth. Call to set an appointment.

120 S Dillard Street, Winter Garden
14501 Grove Resort Avenue Unit 3205, Winter Garden
$325,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel SubDv. ⋅ 34787 Zip Code
Luxury vacation rental within The Grove Resort and Spa. Beautifully furnished with modern furniture and fixtures that make for a one-of-a-kind vacation property, this fully furnished 2-bedroom, 2-bath unit can sleep up to 8 people (room with1 king bed, room with 2 full beds and queen sleeper sofa) and has a gourmet kitchen with stainless steel appliances and quartz counters. The Grove Resort and Spa offers concierge service and has several bars, restaurants, multiple pools and spas, a lazy river, water park, surfing simulator with an instructor, day spa, fishing dock, and paddle boats on Lake Austin. The resort is within several minutes of Disney World with shuttle services to the parks. This is one of Orlando's most luxurious vacation rental resorts.

14501 Grove Resort Avenue Unit 3205, Winter Garden
14501 Grove Resort Avenue Unit 1318, Winter Garden
$399,900
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
OWN this full POOL-VIEW condominium in the MAIN building!!! As you enter this 3rd floor two bedroom, two bathroom unit, an unobstructed view to the Springs Pool welcomes you in the Premier Tower or Building One. What an amazing view!!! In the evenings, you may enjoy Disney's fireworks from your balcony or bedrooms!!! The unit is located in Tower One, where you find the lobby, concierge, restaurant, bar, lounge, fitness center, spa, and market an shop. It overlooks the Spring Pools just outside your building where three pools, splash pool, oversized hot tub and cabanas are awaiting you. You may park your car on the same level as your unit in the garage. The highlight of the resort is the Safari Waterpark. The FlowRider Double surf simulator can be challenging, but professionals help and teach you. Sunbathe while floating down the almost 700-foot lazy river. There are also the two-story, double slides, waiting for you. Everything you deserve as a place to relax and enjoy with your family and loved ones.

14501 Grove Resort Avenue Unit 1318, Winter Garden