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$996,975
3 Beds ⋅ 3 Baths ⋅ Country Lakes SubDv. ⋅ 34787 Zip Code
Virtually Staged. Rarely does a property offer over an acre of land in the heart of Winter Garden. Tucked away in an intimate lake-access community, this beautifully refreshed pool home combines privacy, mature trees, and an unbeatable location just minutes from everything Central Florida has to offer. Set on a beautifully landscaped 1.1-acre lot with no rear neighbors, this stunning residence offers a rare opportunity to enjoy space, serenity, and flexibility in one of Winter Garden's most desirable locations. Designed for both everyday living and effortless entertaining, the home features fresh interior paint, new luxury vinyl plank flooring throughout the main living areas and bedrooms, a newer roof, new water heater, oven, range, custom woodwork, and a beautiful wood-burning brick fireplace that anchors the living space. The expansive covered lanai, refinished screened-in pool with a new pump, and spa create a true indoor-outdoor lifestyle, with multiple access points from the home and a kitchen pass-through window that opens directly to the entertaining area. Privately situated on the opposite side of the main 3 bedrooms, the light-filled bonus room features two closets, French doors, its own exterior entrance, and tranquil views of the mature landscaping. Paired with the adjacent full bath, it offers exceptional flexibility as a potential 4th bedroom, private guest suite, in-law suite, home office, or creative space. The 3rd full bath also serves as a convenient pool bath with direct outdoor access to the lanai. Outside, enjoy beautifully maintained gardens, mature trees, a fully fenced backyard, abundant outdoor living space, and a large detached storage building with electricity. Residents also enjoy private access to Black Lake and Lake Tilden, complete with a boat ramp, tennis court, pavilion, and the peaceful charm of one of Winter Garden's hidden-gem communities. Just minutes from Winter Garden Village, historic Downtown Winter Garden, major highways, area hospitals, and world-famous attractions including Disney World, Universal Orlando, and SeaWorld, this property delivers a combination of land, location, and lifestyle that is rare to find.

14140 Country Estate Drive, Winter Garden
$560,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3a SubDv. ⋅ 34787 Zip Code
Waterleigh! In this master planned community lies this beautiful two story, with all new exterior paint, three bedroom, two and a half bathroom, with a second floor den/flex space, which is perfect for a home office or kids space.! The spacious kitchen features stainless steel appliances, stone countertops, new backsplash and a large island/breakfast bar. This open plan has a large living room/dining room combo with crown molding and a sliding glass door which opens up to the covered lanai area. The master bedroom is on the first floor and has a new tile floor. The owners bath features a walk in shower, double sinks and stone counter top, as well as a walk in closet and a separate linen closet for convenience and extra storage. The laundry area is located on the first floor. Upstairs, you will find two additional bedrooms, a full bath and flex area. This home features an attached rear 2 car garage entrance with convenient drop zone with lots of cabinets for extra storage and granite counter top. Residents have access to four incredible amenity centers with resort-style pools, offering 2 stunning clubhouses with fitness centers, putt putt golf, beach volleyball, tennis, pickleball, BBQ/picnic areas, playground, & dog park. Even better, LANDSCAPING IS INCLUDED in the HOA, allowing you to spend less time on yard work and more time enjoying the community. This property is conveniently located nearby to shopping, grocery stores, restaurants, and hospitals, alongside being close to Walt Disney World, which makes it a magical place to live! Home available to view no appointment needed come take a look .

16933 Oakboro Street, Winter Garden
$565,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hamlin SubDv. ⋅ 34787 Zip Code
Live in the heart of Hamlin! Welcome to this beautifully upgraded 3 bedroom, 2.5 bath home with a versatile first floor flex room that can easily serve as a fourth bedroom, home office, playroom, or guest space. Built in 2021, this move in ready home offers over 2,100 square feet of thoughtfully designed living space, modern finishes, smart upgrades, and an exceptional location in one of Winter Garden's most sought after communities. Inside, you'll find an open concept floor plan filled with natural light, fresh interior paint, upgraded flooring, and stylish lighting throughout. The kitchen is the centerpiece of the home, featuring Level 5 quartz countertops, a large island wrapped in custom porcelain tile, stainless steel appliances, and abundant cabinet space, making it ideal for everyday living and entertaining. Upstairs, the spacious primary suite features a custom walk in closet and an upgraded en suite bathroom with quartz countertops. Two additional bedrooms, a full bathroom, and an updated laundry room complete the second floor. This home also includes valuable upgrades rarely found at this price point, including a whole home water filtration and softener system, an APCO X Ultra air purification system, five Arlo security cameras that convey, and prewiring for additional smart home connectivity. Outside, enjoy the privacy of a rear entry two car garage and a low maintenance yard, giving you more time to enjoy everything this vibrant community has to offer. Located just minutes from Hamlin Town Center, you'll enjoy waterfront dining, shopping, coffee shops, fitness studios, entertainment, Publix, Cinépolis Luxury Cinemas, top rated schools, and convenient access to State Road 429, making it easy to reach Walt Disney World, downtown Orlando, and Orlando International Airport. Homes offering this combination of flexible living space, thoughtful upgrades, modern finishes, and an unbeatable location are hard to find. Schedule your private showing today and discover why so many buyers are choosing to call this community home.

4642 Prairie Creek Street, Winter Garden
$1,095,000
4 Beds ⋅ 4 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code
Welcome to 30 North Park, an exceptional townhome located in the heart of Historic Downtown Winter Garden — directly on the West Orange Trail and just steps from Plant Street Market, Crooked Can Brewery, local dining, shopping, and the weekly Farmer’s Market. This modern farmhouse-style residence offers four spacious bedrooms, each with a private en-suite bathroom and custom-fitted closets, providing comfort, privacy, and flexibility for guests, multigenerational living, or work-from-home needs. A first-floor bedroom serves as an ideal guest retreat, office, or flex space. The second level features an open-concept living area anchored by a designer kitchen complete with Bosch natural gas appliances, a large island, quartz countertops, farmhouse sink, artisan tile backsplash, and floor-to-ceiling windows showcasing views toward downtown and the West Orange Trail. A secondary bedroom with dramatic custom windows adds abundant natural light. On the third floor, dual primary suites offer spacious layouts, oversized windows, powered blinds, spa-inspired walk-in showers, and quartz-finished baths. Thoughtful upgrades throughout include warm wood flooring, patterned tile accents, modern black lighting fixtures, and extensive storage. Built with an STC soundproofing rating of 69, the home provides a quiet interior environment while remaining in one of Central Florida’s most vibrant walkable districts. Enjoy balcony views overlooking the trail and experience low-maintenance living with unmatched proximity to Historic Winter Garden’s amenities. Experience refined, walkable living in the heart of Winter Garden — schedule your private showing today.

64 N Park Avenue, Winter Garden
$849,900
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Exceptional New Price! Experience Refined Florida Living in the Lowest Priced Pool Home in Lakeshore Preserve. Distinguished by its Tuscan elevation, stone accents, and Barrel Tile Roof, this 4-bedroom, 3.5-bath Toll Brothers built home offers timeless curb appeal and thoughtfully designed living spaces. Inside, soaring ceilings, crown molding, and upscale finishes create an inviting yet sophisticated atmosphere. Designed for seamless entertaining, the open-concept kitchen, living, and dining areas are filled with natural light and enhanced by six oversized sliding glass doors that extend the living space outdoors. The gourmet kitchen is the heart of the home, featuring an impressive 14’ center island, upgraded KitchenAid appliances, abundant cabinetry, walk-in pantry, and a built-in storage/mudroom. Outdoors, enjoy a 39’ x 8’ covered lanai overlooking a saltwater pool added in 2021, complemented by extensive paver decking and an expansive screened enclosure—creating a refined outdoor living space ideal for alfresco dining and entertaining. Enjoy the soothing sounds provided by the waterfall pool feature! The first floor includes a flexible bedroom currently used as an office with an adjacent powder room. Upstairs, a spacious bonus loft provides separation and privacy, leading to the luxurious owner’s suite with dual walk-in closets and a spa-inspired bath offering double vanities, soaking tub, frameless glass shower, and private water closet. Two additional bedrooms—one with ensuite bath—along with a full laundry room complete the upper level. Energy-efficient features include double-pane Low-E windows, gas cooktop and dryer, and a tankless water heater. Community fees include lawn care, internet, cable, and access to resort-style amenities such as a clubhouse, pool, fitness center, playgrounds, dog park, firepit and kayak launch. Ideally located in Horizon West, close to shopping, dining, hospitals, schools, and major highways—with Disney parks just minutes away—this home offers the perfect balance of luxury, lifestyle, and convenience.

15672 Shorebird Lane, Winter Garden
$834,000
3 Beds ⋅ 4 Baths ⋅ Park Place/Winter Garden SubDv. ⋅ 34787 Zip Code
131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable Park Place community in the heart of historic Winter Garden, Florida. This beautifully designed three-story home offers 3 bedrooms, 3.5 bathrooms, and 1,906 square feet of heated living space. Each bedroom features its own en-suite bathroom, providing privacy and comfort for all. This home includes an elevator that conveniently connects the first and second floors along with an oversized rear-entry two-car garage, a small balcony, and a convenient in-unit laundry closet. Inside, the open-concept main level boasts a gourmet kitchen with stainless steel appliances, a large island, and ample cabinetry. Premium finishes throughout include wood-look tile flooring, crown molding, and plantation shutters. The primary suite offers generous closet space and a spa-inspired bath with dual vanities, a soaker tub, and a walk-in shower. Thoughtful design and quality craftsmanship combine with a prime location just steps from downtown Winter Garden’s restaurants, shops, and the Plant Street Market, making this property an exceptional opportunity to enjoy upscale living in one of the area’s most sought-after neighborhoods.

131 Oak Laurel Drive, Winter Garden
$1,150,000
6 Beds ⋅ 5 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code
Seller Motivated , Welcome Home! This beautifully renovated 4,305 sq. ft. single-family residence offers the perfect blend of modern upgrades and inviting comfort, located in one of Winter Garden’s well sought-after communities. Discover elegant porcelain tile flooring throughout the first floor, leading to a spacious, updated kitchen featuring quartz countertops, a smart cooktop, and decorative glass cabinetry, ideal for both everyday living and entertaining. The gorgeous master suite includes a custom built-in walk-in closet, providing both style and functionality. With 6BR/5BA, there’s plenty of space for family and guests alike. Enjoy Florida living at its finest in your outdoor oasis, complete with a gazebo and a built-in fire pit seating area, perfect for relaxing evenings or weekend gatherings. The three-car split garage adds convenience and ample storage.Recently renovated and freshly painted, this home is truly move-in ready. Located in a wonderful community offering two sparkling pools and a playground, you’ll love the nearby amenities that make Winter Garden such a special place to live. Tour Today!

10067 Austrina Oak Loop, 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
$2,999,990
6 Beds ⋅ 8 Baths ⋅ Shorefront Cove SubDv. ⋅ 34787 Zip Code
Exquisite Luxury Estate in Shorefront Cove at Horizon West. Presenting a rare opportunity to own a premier residence in the sought-after Shorefront Cove community of Winter Garden’s Horizon West. This elegant two-story estate offers 6,442 square feet of impeccably designed living space, showcasing refined luxury, modern convenience, and breathtaking views of Huckleberry Lake. Boasting 6 spacious bedrooms, 6 full bathrooms, and 2 half baths, this home features dual primary suites, one on the main level and one on the upper level, bonus room, wet bar, theater, large lanai, and 4-car garage offering ample storage and convenience. This residence provides easy access to major highways, premier shopping, dining, entertainment, and top-rated schools, all within one of Central Florida's most desirable communities.

14168 Larkspur Lake Drive, Winter Garden
$635,000
4 Beds ⋅ 3 Baths ⋅ Silverleaf Reserve At Hamlin SubDv. ⋅ 34787 Zip Code
JUST REDUCED - SELLER MOTIVATED! Step right into the highly sought-after Winter Garden lifestyle with this beautiful 4-bedroom, 3-bathroom home in the premier Silverleaf Reserve community. Designed to impress, the expansive open floor plan boasts soaring high ceilings and an abundance of natural light, creating a seamless flow for entertaining and daily living. The modern kitchen is equipped with sleek stainless steel appliances and opens directly into the spacious main living areas. Retreat to your primary suite, a true sanctuary featuring a massive walk-in closet and a luxurious spa-like bathroom designed for ultimate relaxation. Outside, enjoy the beautiful Florida weather year-round on your covered lanai, which overlooks a private, landscaped backyard. Location is everything, and this property delivers unparalleled convenience—you are just a few blocks away from highly rated Hamlin Elementary and Middle Schools, the vibrant dining, shopping, and entertainment at Hamlin Town Center, and major highways for a quick, stress-free commute throughout the Orlando area. This home offers the perfect blend of modern comfort, space, and prime accessibility. Turnkey properties in this neighborhood are in high demand and move fast. Call today to schedule your private showing before this exceptional opportunity is gone!

16271 Silver Grove Blvd, Winter Garden