Winter Garden Real Estate

Winter Garden Real Estate

Welcome to Winter Garden, Florida—a charming city that beautifully blends small-town warmth with modern conveniences. Nestled just west of Orlando, Winter Garden is a hidden gem that offers a delightful escape from the hustle and bustle of city life while still keeping you close to all the attractions that Central Florida has to offer.

Known for its picturesque downtown area, Winter Garden boasts a vibrant mix of historic charm and contemporary flair. Stroll along Plant Street, where you’ll find a delightful array of boutiques, cafes, and restaurants, all set against a backdrop of beautifully preserved historic buildings. The weekly farmers market is a local favorite, showcasing fresh produce, artisanal goods, and a sense of community that’s hard to resist.

Nature lovers will find their paradise in Winter Garden, with access to the scenic West Orange Trail—a 22-mile-long trail perfect for biking, walking, and jogging. The lush parks and serene lakes offer ample opportunities for outdoor activities, picnics, and enjoying the stunning Florida sunshine.

Families will appreciate Winter Garden's top-rated schools and family-friendly atmosphere, making it an ideal place to raise children. The city also hosts various events throughout the year, from holiday parades to music festivals, ensuring there’s always something exciting happening.

With its rich history, vibrant community, and convenient location, Winter Garden is more than just a place to live; it's a lifestyle. Whether you’re looking to buy your first home, expand your investment portfolio, or simply explore a new area, Winter Garden welcomes you with open arms and endless possibilities. Come discover the magic of Winter Garden, where every day feels like a vacation!

Newest Listings in Winter Garden

3 Beds ⋅ 3 Baths ⋅ Osprey Ranch Ph 1 SubDv. ⋅ 34787 Zip Code

Excellent opportunity for homeowners or investors in the highly desirable Winter Garden area! This bright corner-unit townhome in Osprey Ranch offers 3 bedrooms, 2.5 bathrooms and 1,536 sq ft of comfortable living space, with added privacy and abundant natural light. The open-concept main floor features tile flooring, a spacious living and dining area, and a kitchen with granite countertops, clear cabinetry, stainless steel appliances and a large island. Decorative details include a custom TV accent wall and a stone-look accent panel on the kitchen island. Upstairs, all three bedrooms provide privacy, along with a versatile landing area that can be used as a home office or study space. Residents enjoy Osprey Ranch amenities including a resort-style community pool, splash pad, playground and dog park. Ideally located near Hamlin, SR-429, shopping, dining, top-rated schools and Walt Disney World, with convenient access throughout Horizon West and the Orlando area. An exceptionally well-priced opportunity for homeowners or investors looking to own in one of Winter Garden’s growing communities.

15056 Windflower Alley, Winter Garden

4 Beds ⋅ 2 Baths ⋅ Covington Chase Ph 2b SubDv. ⋅ 34787 Zip Code

Virtually Staged. This is not your typical "fully upgraded" listing - this home has been thoughtfully and extensively renovated throughout. Featuring 4 bedrooms, 2 bathrooms, a dedicated office and an additional flex/formal space, it offers exceptional versatility for modern living. The completely remodeled kitchen showcases custom oversized upper cabinetry, upgraded finishes, as a wine/beverage fridge and a rare oversized walk-in pantry not found in the original Ryan Homes floor plan. Both bathrooms have been fully transformed into spa-inspired retreats with luxury bidet features and a full-body shower system, delivering a true at-home spa experience. Even the light switches have been updated, reflecting the level of detail throughout the home. The main living area includes a custom built-in entertainment center, creating a refined focal point ideal for entertaining or everyday relaxation. Step outside to an oversized, fully fenced back yard offering endless potential for a future pool, outdoor kitchen, firepit, garden or custom outdoor living space. Ideally located just minutes from historic Downtown Winter Garden and Plant Street, residents enjoy easy access to dining, shopping, breweries, farmers markets and community events. The West Orange Trail funs through the neighborhood providing direct access to walking, biking, and outdoor recreation. Convenient proximity to major highways ensures quick access to Orlando and surrounding Central Florida destinations. A truly move-in-ready Winter Garden home combining extensive upgrades, flexible living spaces and an unbeatable location, this is a home designed to be lived in, not just listed.

527 Copperdale Avenue, Winter Garden

4 Beds ⋅ 3 Baths ⋅ John Lake Pointe SubDv. ⋅ 34787 Zip Code

Motivated seller! Located in the community of Johns Lake Pointe, this beautifully designed 4-bedroom, 2.5-bath home offers a desirable split floor plan and a spacious 2-car garage. A welcoming front porch sets the tone for this inviting residence. The living room overlooks the private fenced backyard, creating the perfect setting for relaxing or entertaining. The kitchen features chestnut cabinetry, stainless steel appliances, a center island with a sit-in bar, and a separate dining area ideal for gatherings. The primary suite includes a well-appointed primary bathroom with dual sinks, a garden tub, and a walk-in shower. The back porch is protected by a screen. With a recent price improvement, this home presents outstanding value, flexibility, and the opportunity to personalize to your taste. Ideally located less than 20 minutes from Disney, Johns Lake Pointe is a beautifully maintained community offering resort-style amenities, including a clubhouse with a pool and kitchen, fitness center, yoga room, tennis courts, and playground. Enjoy an exceptional lifestyle in a prime location, priced to allow the next owner to create a private oasis. Don’t miss the opportunity to make this remarkable house your home!

745 Marsh Reed Drive W, Winter Garden

2 Beds ⋅ 3 Baths ⋅ Orchard A1-A26 B1 B2 C D1-D4 SubDv. ⋅ 34787 Zip Code

Welcome to this beautiful Winter Garden townhome located in a desirable gated community with a community pool. This bright 2-bedroom, 2.5-bath end-unit townhome features a dedicated office that could easily be converted into a third bedroom, offering added flexibility for guests or a home workspace. An upstairs loft provides additional living space, perfect for a second living area, media room, playroom, or flex space. Interior features include tile flooring, tray ceilings, granite countertops, stainless steel appliances, plantation shutters, and newer wood-look laminate flooring upstairs. A new energy-efficient A/C system with warranty provides added comfort, efficiency, and peace of mind, while the newer roof adds even more value. The townhome also features a two-car rear-entry garage and is ideally located close to top-rated schools, shopping, dining, and Central Florida's world-famous attractions. With its desirable Winter Garden location, gated setting, community amenities, and versatile floor plan, this townhome is a must-see!

13855 Golden Russet Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Crown Point Spgs SubDv. ⋅ 34787 Zip Code

New photos coming soon. Seller offering up to $20,395 toward buyer closing costs, prepaid expenses, and/or an interest rate buydown. Conditions apply. Move-in ready 3-bedroom, 2-bath POOL home in Winter Garden's established Crown Point Springs community with the big-ticket items already handled: new HVAC (2026), new water heater (2026), and a brand new roof already approved, with materials on site for installation. A just-completed professional refresh adds a renovated kitchen with new white shaker cabinetry, quartz countertops, and stainless steel appliances including a Whirlpool glass-top range and dishwasher, along with updated hardware, lighting, and a new Moen pull-out faucet. Both bathrooms feature updated vanities, quartz countertops, and new faucets, mirrors, and fixtures. Additional improvements include fresh interior paint throughout, new LED lighting and fixtures, updated interior doors and hardware, a new front entry door, a freshly painted garage, and refreshed landscaping with fresh mulch. The functional floor plan offers spacious living and dining areas with a fireplace, a primary suite with a walk-in closet, two additional bedrooms, and an attached 2-car garage. Out back, the screen-enclosed private pool and patio provide year-round Florida living. Low $150 semi-annual HOA and no CDD. Conveniently located near Historic Downtown Winter Garden, Plant Street, the West Orange Trail, shopping, dining, parks, and major roadways. Buyer credit available with use of Seller's preferred lender. Schedule your showing today.

1097 Depot Court, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Stoneybrook West I SubDv. ⋅ 34787 Zip Code

Welcome to this charming and beautifully maintained home located in the desirable Winter Garden community! Featuring an open and functional floor plan, this property offers bright living spaces, a spacious kitchen perfect for everyday cooking and entertaining, and comfortable bedrooms designed for relaxation. Enjoy a private backyard space ideal for outdoor activities and quiet evenings. Conveniently situated near top-rated local schools, shopping centers, dining options, and major highways for an easy commute. Schedule your private showing today and discover everything this wonderful home!

1221 Priory Circle, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Osprey Ranch Ph 1 SubDv. ⋅ 34787 Zip Code

Discover an inviting 3-bedroom, 2.5-bath home in Winter Garden, offering a comfortable layout designed for both everyday living and entertaining. The main living areas create an open and welcoming environment, with natural light enhancing the sense of space and connecting the living, dining, and kitchen areas. Upstairs, the bedrooms are thoughtfully separated from the main gathering spaces, providing added privacy and a comfortable retreat at the end of the day. The primary suite offers its own private bath, while the additional bedrooms provide flexibility for family, guests, a home office, or whatever best fits your lifestyle. Beyond the home itself, the location puts you close to everything that makes the Winter Garden area so desirable. Enjoy convenient access to shopping, restaurants, schools, recreation, and major roadways, making it easy to explore Horizon West, greater Orlando, and the many attractions Central Florida has to offer. Whether you're searching for your next home or an investment opportunity in a growing area, this property delivers a combination of location, functionality, and Florida living that is hard to overlook. Schedule your private showing and come see the possibilities for yourself.

15038 Windflower Alley, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code

Welcome to Stoneybrook West—a one-of-a-kind community in Winter Garden! This premier neighborhood offers 24-hour guarded entry, a massive town center, and resort-style amenities including an Olympic-sized pool with a splash zone, state-of-the-art fitness center, playground, tennis, basketball, and pickleball courts. Enjoy lakeside living with a fishing/viewing pier and private boat ramp, plus a full calendar of community events. Best of all, your HOA fees cover both internet and cable! Set on a tranquil pond with no rear neighbors, this home boasts irresistible curb appeal from the moment you arrive. Inside, the thoughtfully designed floor plan balances elegance and ease. The front of the home features formal living and dining areas—perfect for hosting—while the rear opens to a bright, open-concept kitchen and family room ideal for everyday living. The kitchen is a chef's delight with ample counter space, a walk-in pantry, stainless steel appliances, stylish tile backsplash, and a breakfast bar. Step through the sliding doors to a screened patio and fully fenced backyard—a private oasis for pets, play, or peaceful pond gazing. Need space for guests or extended family? A main-floor bedroom with a full bath offers flexibility and privacy. Upstairs, a generous loft awaits—use it as a media room, playroom, or second living area. Both the loft and the primary suite open to a screened balcony with serene views. The primary retreat itself is a showstopper, featuring a garden tub, separate walk-in shower, dual vanities with a makeup station, and an enormous walk-in closet. Convenience continues with an upstairs laundry room equipped with cabinets and a utility sink. Fresh new flooring has been installed throughout the entire upper level, and the home has been treated to a brand-new coat of paint, giving it a clean, modern feel throughout. Recent upgrades also include a new roof (2023), new water heater (2023), and AC (2019). You'll also appreciate surround sound pre-wiring in the family room and loft, ceiling fans throughout, and abundant storage. Located just steps from the resident gate, Balforn Tower Way places you minutes from the community town center, golf clubhouse, top-rated schools, dining, shopping, medical facilities, and entertainment. This is more than a home—it's a lifestyle.

2549 Balforn Tower Way, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code

Welcome to this beautiful 2024 Taylor Morrison home in Harvest at Ovation. Offering 4 bedrooms, 3.5 bathrooms, and 2,332 square feet, this residence features a bright open-concept layout and modern finishes throughout. A standout feature is the covered front porch overlooking a beautiful community green space, with no residence directly in front, providing an open view and added privacy. The kitchen offers quartz countertops, a large island, and contemporary cabinetry. A first-floor bedroom with a full bathroom provides flexible space for guests or a home office. Additional highlights include a covered lanai, laundry room, natural gas, and a two-car garage. Residents enjoy a community pool with cabana, butterfly garden, nature play space, dog park, and walking trails. Conveniently located near shopping, dining, SR 429, and Central Florida attractions. The area also features the newly opened Ovation Elementary and the recently built Water Spring Middle campus. Buyers should independently verify school zoning.

15154 Alder Chase Alley, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 01 SubDv. ⋅ 34787 Zip Code

Welcome home to this bright, beautifully maintained and thoughtfully updated first-floor condo in the heart of Winter Garden. This 2-bedroom, 2-bath residence offers 918 square feet of comfortable living space with tasteful improvements and smart use of space throughout. Step inside to an inviting, open living and dining area featuring wood-look luxury vinyl flooring throughout, recessed lighting and an abundance of natural light. Recently replaced windows are an especially valuable improvement, enhancing the home’s fresh, updated feel while offering an upgrade buyers will appreciate for years to come. The kitchen has been tastefully refreshed with granite countertops, a stylish tile backsplash, breakfast bar and thoughtful cabinetry updates, creating a functional space that opens naturally to the dining and living areas. A standout feature is the custom reconfigured laundry and pantry area, thoughtfully redesigned to make the most of the available space. The stackable washer and dryer provides convenient laundry access while allowing for additional organized pantry and cabinet storage—an incredibly functional upgrade that you won’t find in every unit. Both bedrooms are comfortably sized, and the continuous wood-look flooring creates a clean, cohesive feel throughout the home. Additional improvements include a tankless water heater, updated lighting and numerous thoughtful touches throughout. Enjoy your own large covered and screened front porch, offering additional space to relax and enjoy the Florida weather. Combined with convenient first-floor living and a well-maintained community setting, this home offers an easy, comfortable lifestyle in a desirable Winter Garden location. Bright, clean, thoughtfully updated and truly move-in ready—this is a condo that stands out from the rest.

27 Windtree Lane Unit 102, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code

Under Construction. .

12331 Silk Mimosa Alley, Winter Garden

Johns Cove 43/104 SubDv. ⋅ 34787 Zip Code

Don't miss this rare opportunity to own over half an acre of waterfront property on beautiful Johns Lake! This is the last available lot in Johns Cove, an exclusive gated community of just 69 custom homes. Build your dream home and private boat dock and enjoy everything lakefront living has to offer-fishing, boating, jet-skiing, water skiing, and incredible sunrises from your backyard. Johns Cove is ideally located near charming Historic Downtown Winter Garden, the West Orange Trail, A-rated schools, world-famous theme parks, major shopping, dining, and Orlando international Airport. A true gem offering space, privacy, and lifestyle. Schedule your private viewing today- an opportunity like this won't last long!

906 Johns Point Drive, Oakland

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