4 Beds ⋅ 2 Baths ⋅ Deerfield Place A-G SubDv. ⋅ 34787 Zip Code

Imagine coming home to a place where comfort, convenience, and community come together perfectly. Nestled in the highly desirable Deerfield Place neighborhood, this beautiful 4-bedroom, 2-bath home offers the space, style, and location today's buyers are searching for. From the moment you step inside, you'll appreciate the bright, open layout designed for making memories. The heart of the home is the spacious kitchen, featuring upgraded cabinetry, stainless steel appliances, and plenty of room to gather with family and friends. Whether you're hosting holiday celebrations, enjoying a quiet morning coffee, or helping with homework while preparing dinner, this home was designed for the moments that matter most. The private owner's retreat provides a peaceful escape at the end of the day, while the additional bedrooms offer flexibility for family, guests, a home office, or a fitness space. Step outside to your fully fenced backyard, perfect for weekend barbecues, pets, playtime, or simply relaxing under the Florida sunshine. What truly sets this home apart is its incredible Winter Garden location. Just minutes from Historic Downtown Winter Garden, the award-winning West Orange Trail, Winter Garden Village, top-rated schools, dining, shopping, and entertainment, you'll enjoy the best of Central Florida living right outside your door.

231 Doe Run Drive, Winter Garden

$600,000

5 Beds ⋅ 3 Baths ⋅ Lakeview Reserve SubDv. ⋅ 34787 Zip Code

Virtually Staged. Experience elevated living in the gated WATERFRONT community of Lakeview Reserve, ideally situated in the heart of historic downtown Winter Garden in the GOLF CART DISTRICT with LOW HOA. This impressive FIVE-bedroom, THREE-bath residence with dining space and LOFT offers an exceptional combination of space, comfort, and versatility, thoughtfully designed to accommodate both everyday living and grand-scale entertaining. Boasting a generous floor plan with expansive living areas and well-proportioned bedrooms, the home provides ample room for growing families, multigenerational living, or those seeking dedicated spaces for a home office, fitness room, or media retreat. Situated on a premium homesite spanning nearly one-quarter of an acre (.19), the property presents endless possibilities for outdoor enjoyment. Whether you envision creating a private backyard oasis, adding a custom pool, designing an outdoor kitchen, or simply enjoying the abundance of open green space, this oversized lot offers the flexibility to bring your vision to life while still providing plenty of room for recreation and relaxation. Upon entering, you are welcomed by a thoughtfully designed open-concept floor plan enhanced by new flooring and a freshly painted interior (2023-2024), creating a bright and inviting atmosphere throughout. The beautifully appointed and newly UPDATED gourmet kitchen serves as the heart of the home, featuring stainless-steel appliances, quartz countertops, shaker style cabinets, and two pantries. The living area is adjacent to the kitchen and presents a great opportunity to expand into the outdoor space creating an indoor-outdoor vibe. Designed with flexibility and comfort in mind, the main level offers a generously sized guest bedroom and a full bathroom, ideal for visitors, a home office, or multigenerational living. The laundry room and dining space are also located on the main level. Upstairs, the spacious primary suite provides a private retreat, while three additional bedrooms, full bath, and loft offer abundant space for family and guests. The primary suite includes a garden tub with separate shower, vanity, linen closet, and walk-in closet. Enjoy picturesque views of Lake Apopka from multiple vantage points throughout the home, creating a serene backdrop for everyday living. ADDITIONAL UPDATES: roof (2018), water heater (2025), downstairs AC (2024-2025), Just moments away, residents enjoy exclusive access to a private community dock overlooking the lake—an idyllic setting for morning coffee, fishing, or taking in spectacular sunset views. Located within the golf-cart district, this remarkable home places you just minutes from the charming boutiques, acclaimed dining, farmers market, and year-round events that make downtown Winter Garden one of Central Florida’s most sought-after destinations. Convenient access to major highways (Turnpike, 429, East-West Expressway) further enhances the lifestyle, placing world-renowned attractions such as Walt Disney World, Universal, and downtown Orlando within easy reach. You can access the 22 mile long WEST ORANGE Trail just footsteps outside of the community to take in cycling and exercising. Move-in ready, this exceptional residence offers a rare opportunity to enjoy luxury, convenience, and a true sense of community in one of Winter Garden’s sought after gated neighborhoods. Measurements are approximate. Buyer is responsible for verifying information.

181 Zachary Wade Street, Winter Garden

$730,000

5 Beds ⋅ 4 Baths ⋅ Osprey Ranch Ph 1 SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully upgraded home in Winter Garden, where style, comfort, and thoughtful design come together seamlessly. From the moment you step inside, you’re greeted by an open, bright, and airy layout, enhanced by elegant farmhouse-inspired finishes and abundant natural light throughout. The main home features no carpet, creating a clean and modern aesthetic, while stunning custom built-in cabinetry in the kitchen, living room, and bedrooms adds both sophistication and functionality. At the center of the home, the spacious kitchen is designed to impress, featuring a large island perfect for entertaining, elegant finishes, and seamless flow into the living and dining spaces. Every detail has been thoughtfully selected, and with tons of upgrades throughout, this home feels elevated at every turn. One of the standout features is the private studio above the garage, ideal for guests, extended family, a home office. Located in the desirable Osprey Ranch community, this home is just minutes from Walt Disney World and everyday conveniences. Even better, you are just steps from the resort style amenities, including the community pool, splash pad, cabana, and playground, offering the perfect blend of lifestyle, convenience, and community living.

15591 Gentle Rain Drive, Winter Garden

$1,049,000

5 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Located in the highly desirable Westhaven at Ovation, this exceptional five bedroom, four bathroom home sits on one of the largest lots in the community with an impressive 0.28 acres, offering extra privacy, space, and an unbeatable setting. With no front or rear neighbors and peaceful pond views behind the home, this property delivers a rare combination of comfort and tranquility. Designed with both elegance and functionality in mind, the home features a spacious open layout with a large loft, an oversized covered lanai perfect for entertaining, and a charming front porch that creates a warm welcome. The gourmet kitchen is equipped with premium KitchenAid appliances and an LG InstaView Door-in-Door refrigerator, combining luxury and modern convenience. Thoughtful upgrades can be found throughout the home, including elegant open rail stairs with luxury vinyl flooring, floor-to-ceiling tile in the bathrooms, and custom-designed spaces in the primary suite closet, laundry room, and pantry for maximum organization and style. The laundry room also includes a utility sink, adding extra practicality for everyday living. The spacious primary suite and well-distributed floor plan provide comfort for the entire family, while the proximity to the community clubhouse adds even more convenience and lifestyle appeal. With a two car garage, exceptional finishes, and one of the best locations in the neighborhood, this home is truly a standout opportunity in Winter Garden.

13181 Toolcross Way, Winter Garden

$885,000

5 Beds ⋅ 4 Baths ⋅ Encore/Ovation-Ph 3 SubDv. ⋅ 34787 Zip Code

Experience elevated Florida living in the highly sought-after resort-style community of Encore at Ovation, just minutes from Walt Disney World and Central Florida’s premier attractions. This exceptional 5 bedroom, 4 bath residence offers 3,687 square feet of thoughtfully designed living space with tranquil conservation views, blending luxury, comfort and functionality in every detail. From the moment you enter, you’ll appreciate the home’s refined finishes, expansive layout and seamless indoor-outdoor flow designed for both everyday living and effortless entertaining. Upgraded tile flooring spans the entire main level, while engineered hardwood flooring enhances the staircase. At the heart of the home, the gourmet kitchen is beautifully appointed with upgraded cabinetry, premium countertops, an exterior-vented range hood and a redesigned oversized center island strategically positioned to maximize prep and cooking space — an ideal setup for both casual meals and culinary enthusiasts. A large walk-in pantry provides abundant storage, while the formal dining room offers the perfect setting for hosting family dinners and special occasions. The main floor also features a private guest bedroom and full bath with direct outdoor access, creating the perfect space for visitors, multigenerational living or a dedicated home office. Upstairs, an elegant open-rail staircase leads to a bright and versatile loft area, ideal for a media room, workspace or additional lounge space. The luxurious primary suite serves as a true retreat, complete with a spa-inspired en-suite bath featuring dual vanities, a semi-frameless glass shower, an expansive walk-in closet and a private balcony perfect for enjoying Florida’s year-round sunshine. Three additional generously sized bedrooms and another spacious loft complete the upper level. Additional upgrades include a well-designed laundry room with a built-in utility sink for added convenience. A spacious three-car tandem garage offers ample room for vehicles, storage and hobbies. Step outside to the fenced expansive backyard overlooking peaceful conservation views, with plenty of room to design your dream outdoor oasis. Residents of Encore at Ovation enjoy access to outstanding community amenities including a resort-style pool, clubhouse, fitness center and lawn maintenance services. Ideally located near world-class shopping, dining, entertainment and major highways, this move-in-ready home offers the perfect blend of luxury, lifestyle and convenience. Don’t miss the opportunity to make this stunning property your next home.

13978 Lanyard Way, Winter Garden

$1,020,000

3 Beds ⋅ 2 Baths ⋅ Lake Avalon Groves Rep SubDv. ⋅ 34787 Zip Code

Rare opportunity to own nearly 5 acres in the coveted Lake Avalon Rural Settlement—where horses, heritage oaks, and peaceful country living meet the convenience of Winter Garden. Escape the hustle and discover one of Winter Garden's last remaining rural neighborhoods. Set on 4.85 fully fenced acres, this picturesque property offers expansive green pastures, majestic oak and heritage trees, and the quiet, open spaces that have become increasingly difficult to find. Bring your horses, livestock, and four-legged companions. The property features a barn with tack room, two stalls with run-outs, multiple pasture areas, and plenty of room to enjoy the outdoor lifestyle Lake Avalon Rural is known for. A long driveway leads to a comfortable 3-bedroom, 2-bath home, perfectly positioned to take advantage of the property's natural beauty and peaceful surroundings. Located within the highly desirable Lake Avalon Rural Settlement, residents enjoy a unique blend of country charm and modern convenience. This close-knit community is known for its' equestrian lifestyle, small farms, wide-open spaces, and commitment to preserving the area agricultural heritage and country character. Despite its tranquil setting, you're only minutes from Historic Downtown Winter Garden, Fowler Grove, Hamlin Town Center, major highways, area attractions, shopping, dining, and top-rated schools. Whether you're dreaming of a horse property, hobby farm, or simply a private retreat beneath the shade of towering oaks, this exceptional property offers the space, freedom, and lifestyle you've been searching for. Experience the peace of country living without sacrificing the convenience of city amenities.

16104 Sandhill Road, Winter Garden

$632,990

3 Beds ⋅ 3 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code

Under Construction. .

12537 Grape Chardonnay Alley, Winter Garden

$610,000

5 Beds ⋅ 3 Baths ⋅ Panther View 40 SubDv. ⋅ 34787 Zip Code

Nestled in the sought-after Innovation at Panther View community of Horizon West, this 5-bedroom, two-story home delivers the space, style, and flexibility today's buyers are looking for, with solar and a Tesla EV charger already in place to keep your monthly energy costs working in your favor. Step inside to rich wood-look tile flooring that flows throughout the entire first floor, setting a warm yet sophisticated tone. The heart of the home is a show-stopping gourmet kitchen featuring white shaker cabinets, quartz countertops, a dramatic shiplap island with seating for four, subway tile backsplash, stainless appliances, and statement black pendant lighting. It opens seamlessly to the dining area and living spaces, making it a true chef's dream and the natural gathering point of the home. A formal sitting room with beadboard wainscoting and a gorgeous chandelier adds an elegant touch perfect for entertaining. This home gives you more than just 5 bedrooms. A flexible den on the first floor works beautifully as a home office, a study, or a playroom, and the first-floor guest bedroom is ideal for multigenerational living or visiting family. Upstairs, a spacious loft with custom board-and-batten accent walls offers a true second living space, perfect as a media room, kids' hangout, or upstairs lounge. Retreat to the grand primary suite with a tray ceiling, custom wainscoting wall, and a en-suite bath complete with a garden soaking tub, dual vanities, and a walk-in glass shower. Three additional bedrooms with thoughtful character round out the upper level. Step outside to the screened lanai and enjoy easy, low-maintenance Florida living year-round. Innovation at Panther View is a boutique 152-home community wrapped by the Panther Lake golf course, with amenities including a playground, dog park, outdoor amphitheater, covered BBQ pavilion, and walking trails. Just minutes from SR-429, Hamlin Town Center, top-rated Orange County schools, and Walt Disney World, with the new Horizon West Regional Park.

7542 Summerlake Groves Street, Winter Garden

$610,000

4 Beds ⋅ 4 Baths ⋅ Harvest/Ovation Ph 2 SubDv. ⋅ 34787 Zip Code

Move right into one of the most sought-after floor plans in Harvest at Ovation. This just-completed Taylor Morrison Baldwin model offers the rare opportunity to skip the build timeline and step into a never fully lived-in home loaded with designer upgrades and timeless style. Originally purchased as a long-term move, the sellers had a change of plans, creating an incredible opportunity for the next owner. With soaring 20-foot ceilings in the main living area, this home makes an immediate impression the moment you walk through the door. Natural light pours into the open-concept layout, highlighting the upgraded flooring, custom window treatments, and carefully curated finishes throughout. The kitchen was designed to be the centerpiece of the home, featuring white and chrome GE Café appliances, a gas cooktop, oversized island, designer lighting, and striking blue cabinetry that brings warmth and character to the space. It flows seamlessly into the dining and living areas, making it ideal for entertaining or everyday living. The first-floor ensuite bedroom with a walk-in closet offers flexibility for guests, multigenerational living, or a private office setup. Upstairs, the spacious primary suite feels like a retreat with a spa-inspired bath and elevated design selections, while the additional bedrooms and bathrooms continue the same high-end aesthetic throughout the home. Additional upgrades include an epoxy-coated garage floor, elevated bathroom finishes throughout, covered lanai, and premium design selections that would be costly and time-consuming to recreate in a new build today. Located in the highly desirable Harvest at Ovation community, residents enjoy resort-style amenities including a pool, playground, walking trails, and green spaces, all just minutes from Flamingo Crossings, Walt Disney World, Horizon West dining, shopping, and major roadways. Why wait months for construction when this designer-finished Baldwin is available now?

16186 Honey Harvest Street, Winter Garden

$889,000

5 Beds ⋅ 4 Baths ⋅ Ests/Lakeview Preserve SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. Welcome to your dream home in the highly sought-after Lakeview Preserve Estates, where modern luxury meets refined living. This exceptional designer-furnished residence offers 5 bedrooms, 4 bathrooms, over 4,000 square feet of thoughtfully curated living space, and a spacious 3-car garage, all situated on an oversized homesite with ample room to create your own private outdoor oasis and custom pool retreat. Designed with sophistication in mind, this turnkey home showcases soaring ceilings, abundant natural light, luxury wood-look tile flooring throughout the main level, and an expansive open-concept floor plan ideal for both grand entertaining and everyday comfort. At the heart of the home is the gourmet chef’s kitchen, featuring quartz countertops, 42-inch shaker-style cabinetry, an oversized center island, designer finishes, and a massive walk-in pantry that seamlessly flows into the spacious living and dining areas. The first floor offers an incredibly desirable layout with three bedrooms, including two private primary suites. The main owner’s retreat serves as a luxurious sanctuary featuring a spa-inspired bathroom with dual vanities, an oversized walk-in shower, and custom walk-in closets. A second primary suite with its own full bathroom provides the perfect setup for multi-generational living, long-term guests, or added privacy. An additional bedroom and full bathroom are also conveniently located on the main level. Upstairs, you’ll find generously sized secondary bedrooms, a large bonus/game room, and an additional living area perfectly suited for entertaining, a media room, home office, or flexible multi-generational living space. Located within the exclusive gated community of Lakeview Preserve near Johns Lake, residents enjoy resort-style amenities including a luxury clubhouse, state-of-the-art fitness center, zero-entry pool, splash pad, playground, scenic lakeside trails, and private kayak launch access. Ideally positioned just minutes from SR-429, Walt Disney World, Winter Garden Village, Downtown Winter Garden, Clermont, and top-rated schools, this impeccably maintained home delivers the perfect blend of luxury, lifestyle, and convenience. Schedule your private showing today and experience the elegance and comfort of Lakeview Preserve living.

3286 Mainsail Court, Winter Garden

$2,500,000

6 Beds ⋅ 7 Baths ⋅ Lakeshore Preserve Ph 4 SubDv. ⋅ 34787 Zip Code

This extraordinary lake-view residence redefines luxury, comfort, and sophistication in the heart of Winter Garden. Located in the highly sought-after Lakeshore Preserve community, this stunning home impresses from the moment you arrive with an elegant paved driveway, beautifully manicured landscaping, and grand double entry doors leading into a dramatic two-story foyer with soaring ceilings and an unforgettable first impression. Designed for exceptional living and entertaining, the home features a sophisticated open-concept floor plan filled with abundant natural light and breathtaking lake views that create a serene and picturesque atmosphere throughout the property. The elegant dining area showcases stunning views of the pool and lake, creating the perfect setting for memorable gatherings with family and friends. The gourmet kitchen is truly a chef’s dream, featuring granite countertops, a spacious center island with seating, stainless steel appliances, designer tile backsplash, and a large walk-in pantry with custom built-in shelving. Overlooking the expansive living room, the space is enhanced by tray ceiling details and elegant recessed lighting, offering both warmth and sophistication. Sliding glass doors seamlessly connect the indoor and outdoor living spaces, opening to a spectacular pool deck and outdoor gourmet area designed for the ultimate Florida lifestyle. Relax while enjoying peaceful water views from your private backyard oasis — the perfect place to entertain, unwind, and enjoy Florida sunsets over the lake. The luxurious primary suite serves as a private retreat, featuring a spa-inspired bathroom with modern square sinks, a soaking tub, and a spacious walk-in rain shower. A separate laundry room provides ample cabinetry and additional storage for convenience and organization. Residents of Lakeshore Preserve enjoy outstanding resort-style amenities, including a clubhouse, resort-style swimming pool, fitness center, yoga room, playgrounds, dog park, sand volleyball court, fishing pier, and community canoes and kayaks. The HOA also maintains the community common areas, allowing for a truly low-maintenance lifestyle. Ideally located just minutes from Orange County National Golf Center, Walt Disney World Resort, premier shopping, dining, top-rated schools, and major highways, this impeccably maintained lakefront-inspired home offers the perfect combination of luxury, convenience, and lifestyle. A rare opportunity to own an exceptional lake-view home in one of Winter Garden’s most desirable communities.

15505 Shorebird Lane, Winter Garden

$825,000

5 Beds ⋅ 4 Baths ⋅ Verde Park Ph 1 SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. Price improved and ready for its next owner, this beautifully maintained pool home in the sought-after Verde Park community offers more than 4,240 square feet of thoughtfully designed living space on a beautiful 0.26-acre corner lot in one of Winter Garden’s most beloved communities. With 5 bedrooms and 4 bathrooms, the home delivers an exceptional combination of space, comfort, and Florida outdoor living with a flexible layout designed for everyday living and entertaining. Inside, elegant formal living and dining rooms, architectural archways, and generous gathering spaces create a warm and welcoming first impression. The expansive family room connects seamlessly to a gourmet kitchen complete with granite countertops, stainless steel appliances, a cooktop, built-in wall oven, and a sunny breakfast nook overlooking the outdoor living area - the kind of space where mornings feel easy and gatherings happen naturally. The versatile floor plan offers room for a variety of needs, including a downstairs Murphy bed office that is perfect for guests or working from home, plus an additional downstairs bonus room with exciting potential as a next-generation living space ideal for multigenerational families or extended stays. Upstairs, the primary suite wraps you in comfort with a large bedroom, spa-like bath, garden tub, dual vanity, separate walk-in shower, and a custom oversized walk-in closet with built-in storage. The second floor also features a large open loft with a convenient kitchenette and a dedicated media room, creating the perfect setup for movie nights or entertainment. Outdoors, enjoy a private screened pool and lanai, covered patio, and summer kitchen designed for year-round enjoyment. The home is also EV charging ready, adding modern convenience for today’s lifestyle. When you’re ready to explore, everything is right at your doorstep. Enjoy walkable access to the West Orange Trail, perfect for morning bike rides, jogging, or evening strolls. Major shopping, including Costco, popular retail, and everyday conveniences, is just minutes away, charming downtown Winter Garden, with its vibrant farmers market, local dining, and boutique shops, is a short drive from home. Add easy access to Montverde Academy and the Florida Turnpike, and this location truly checks every box. Some photos are virtually staged. Aerial property lines are approximate and should be verified by buyer. *Aerial photo property lines are an estimate and to be verified by buyer, some photos are virtually staged

14001 Rugby Street, Oakland

Recently Sold Listings in Winter Garden, FL

All Sold Homes for Sale in Winter Garden, FL

The Nest Group

Search

Resources

About