Winter Garden Property Search

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Winter Garden is a city located in Orange County, Florida known for its historic downtown, recreational opportunities, and proximity to major theme parks. Modern history of Winter Garden dates back to the late 1800s when the area was primarily used for agriculture, primarily citrus farming. In the early 1900s, the city began to experience a population boom as more and more people moved to the area to take advantage of the nearby opportunities for employment and the fertile land for farming.


In the 1920s, the city's downtown area was developed, with the construction of many homes, businesses, and community amenities. Throughout the years, Winter Garden has been known for its tree-lined streets, historic architecture, and proximity to major highways and local amenities.


The real estate market in Winter Garden offers a variety of properties, including single-family homes, townhomes, and condominiums. Single-family homes are the most common type of real estate in Winter Garden, with prices ranging from the low hundreds of thousands to the high hundreds of thousands. These homes can be found in a variety of styles, including traditional, Mediterranean, and contemporary. Many of these homes are situated on large lots and have features such as swimming pools, private lakes, and mature landscaping.


Townhomes and condominiums are also available in Winter Garden, particularly in the gated communities. These properties offer a more maintenance-free lifestyle and are typically more affordable than single-family homes.


Winter Garden is also known for its abundance of recreational opportunities, including parks, lakes, and nature trails, as well as its proximity to major theme parks like Walt Disney World and Universal Studios. These factors, combined with its historic downtown and stable real estate market make Winter Garden a highly desirable place to live.


Our website features the best Winter Garden real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

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Hot Winter Garden Properties

5 Beds 4 Baths Johns Lake Pointe A & S SubDv. 34787 Zip Code
Looking for a cozy home that's conveniently located near all the attractions? Look no further! This charming house is situated just minutes away from downtown Winter Garden and only a short drive from Disney. Located on a desirable corner lot, almost a quarter of an acre, and fully fenced, in Johns Lake Pointe! This stunning property features a large heated pool perfect for relaxing and entertaining. With almost 4200 square feet of living space, this home offers 5 spacious bedrooms, an office downstairs, a loft, and a media room, providing plenty of room for the whole family to spread out. The solar panel system has been paid off, ensuring that you will enjoy energy savings for years to come. The 3 car tandem garage provides ample parking and storage space. Inside the home, you will find custom closet shelving in the primary bedrooms massive closet, in two of the secondary closets, and the kitchen pantry, providing optimal organization and storage solutions. This home is perfect for hosting guests or enjoying quiet nights in with family. The open concept living areas allow for easy flow and connectivity between the living room, dining room, and kitchen. The kitchen features modern appliances and ample countertop space, making meal prep and cooking a breeze. Upstairs, you will find 4 of the 5 spacious bedrooms, each with its own unique charm and character. Whether you're entertaining guests or just enjoying a quiet evening at home, the media room and loft offer the perfect space to unwind and have fun. And with new exterior paint, the home's curb appeal is sure to impress. This home is perfect for those who want the best of both worlds - the comfort and privacy of a large home, combined with the luxury and convenience of modern amenities. Don't miss out on the opportunity to make this corner lot home your own!

403 Egret Place Drive, Winter Garden

3 Beds 2.5 Baths Encore At Ovation SubDv. 34787 Zip Code
Fall in love with this stunning 3 bed, 2.5 bath home with alley access and two car garage. You will love the beautiful open floor plan and perfectly designed living space. The family room, kitchen, and dining room are all open to each other creating a perfect spot for family hangouts or weekend entertaining. Your inner chef will enjoy the impressively upgraded kitchen: Butler pantry, wine fridge, stainless steel appliances, natural gas stove, 42" cabinets with crown molding and under cabinet lights, quartz countertops, and tile backsplash. The first floor and all bathrooms feature luxury porcelain tile flooring - beautiful & durable! Upstairs you will find a generously sized loft - the perfect space for movie night, game day, or office space. It separates the master suite in the back of the home from the secondary bedrooms, giving everyone the privacy they deserve. The master suite features trey ceilings, a large walk-in closet, and a luxury-designed private bath - including a tiled frameless walk-in shower enclosure, a separate soaking tub, dual sinks, and raised countertops. Acrylic flooring placed in the garage (2023). Encore at Ovation HOA provides its homeowners with community amenities such as a park, playground, community pool, and fitness center. The location is around the corner from Disney and minutes to downtown Orlando. You'll enjoy trails and shopping nearby, and you're only about an hour to the beach! Come see everything this incredible home has to offer!

16053 Tollington Alley, Winter Garden

4 Beds 2 Baths Covington Park SubDv. 34787 Zip Code
Location ! Location ! This beautiful home with great curb appeal is in Covington Chase (formerly Covington Park) and has a BRAND NEW ROOF and gutters and is in the GOLF CART DISTRICT of desirable WINTER GARDEN featuring the Plant Street area with great shops, wonderful restaurants, Farmer's Market on Saturdays, festivals, and the Garden Theater ! You can drive your golf cart on the street or walk or bike on the West Orange Trail that runs right through the community or take a short drive to the charming Downtown area. You enter the large foyer and there is a bedroom to the right that would be perfect for a home office or study. Next to it is a room with double pocket doors that was used as a formal dining room. The combo kitchen/dinette/living room has French doors that open to the screened porch and patio with stone pavers and a motorized retractable screen that opens up between the porch and patio. Relax and enjoy outdoor living overlooking the private backyard with mature trees ! The kitchen features 42" cherrywood cabinets, granite counters, tile backsplash, breakfast bar, and stainless steel appliances. Washer & dryer included also. New water heater, dishwasher & dryer too ! Plank style neutral tile flooring throughout except for the master bathroom. There are 5 bedrooms plus the dining room which could even be a bedroom for a large family or guests. The master suite has a walk in closet, dual sinks, and separate tub & shower. There is a gated community pool and covered playground covered by low HOA fees of $185 per quarter. Easy access to 429, the Turnpike and W. Colonial DR/Hwy. 50 !

303 Millwood Place, Winter Garden

5 Beds 5.5 Baths Hamilton Gardens Ph 2a 2b SubDv. 34787 Zip Code
Must Read!! Everything you ever wanted, including all the Disney and Seaworld fireworks, every day! Let me not forget to mention the shuttle launches Space Coast can be seen from the backyard!What a spectacular five-bedroom 2021 home in the community of Hamilton Gardens. Winter Garden has it all. A large pie-shaped lot, a fenced-in yard, no rear neighbors, and an extensive number of solar panels, the seller gets a refund on their power bill. Generac generator ($25k value), Tankless gas water heater, Nest security system and cameras outside, outdoor kitchen, extended covered lanai with three ceiling fans. There's more! A water softener system and alkaline water faucet. A downstairs bedroom with an adjacent bathroom. Study/home office with french doors, large formal dining or living space as you walk in. Beautiful kitchen with an island that opens onto a large living and dining area with glass sliders onto the lanai. The fans, chandeliers, and pendant lighting throughout the house are unique—large format tiled floors on the first floor. The second floor has a loft with extensive views, a laundry room, and four more bedrooms, including the primary bedroom suite. This home comes with 5.5 bathrooms in total. The home has a covered front porch, a double garage, and nice landscaping. Great schools, restaurants, hospitals, and shopping are all close by. Please take a look at all the photos and 3d models. Fast close available.

Winter Garden

5 Beds 3 Baths Stoneybrook West - Masthead Landing SubDv. 34787 Zip Code
Seller is offering a closing cost credit of $10,000. Welcome to your dream home in Winter Garden, Florida! This stunning 5 bedroom, 3 bathroom pool home boasts luxury and comfort throughout its spacious floor plan. As you step through the front door, you are greeted by an elegant two story foyer that leads to a grand living room with soaring ceilings and beautiful natural light. The open concept layout seamlessly flows into the formal dining area and gourmet kitchen, which features Corian countertops, stainless steel appliances, and plenty of cabinet space. The main level also includes a cozy family room overlooking the beautiful pebble tech pool, a guest bedroom with built in murphy bed and cabinets, and a full bathroom. Upstairs, you will find four additional bedrooms, including the luxurious master suite complete with a walk-in closet, dual vanities, a soaking tub, and a separate shower. Step outside into your own private oasis, where you can relax and entertain in the screened-in pool area surrounded by lush tropical landscaping. This home also includes a 2-car garage and is situated on a spacious lot with ample room for outdoor activities with a fully fenced yard. Located in the desirable Stoneybrook West community of Winter Garden, this home is just minutes away from world-class shopping, dining, and entertainment. With easy access to major highways, theme parks, and beaches, this is the perfect place to call home. Don't miss your chance to own this breathtaking property – schedule your showing today!

14936 Masthead Landing Circle, Winter Garden

3 Beds 2 Baths Waterleigh Ph 1b SubDv. 34787 Zip Code
Welcome to this charming, well-maintained 3 bedroom 2 bath home in the highly sought-after community of Waterleigh in Winter Garden!! This SINGLE-story home offers a split floorplan with an open-concept living room/kitchen combo, drop-off zone at the rear, attached garage and so much more! As you enter through the front door, you walk right into the generously sized foyer. Hook a left, and you will find 2 nicely sized bedrooms and a full bathroom. Continuing to the "heart of the home", you'll find the open kitchen and family room combo flooded with natural light!! The height of the ceiling really makes this main area feel open and airy! In your kitchen, you'll be pleased with the 42" cabinets, granite island, stainless steel appliances, and walk-in pantry! The pleasantries don't stop there!! Your owner's suite is huge with an ensuite that has an oversized shower, dual sinks, AND plenty of space in the walk-in closet!! On your way to the rear of the home, you'll find a sliding glass door that leads you to your covered patio, laundry room, and an ATTACHED 2-car garage with a LONG paved driveway that will not disappoint! Bring your belongings and move right into this MAINTENANCE-FREE style of living. The HOA services your lawn, mulch, shrubs, etc. This community is something special! Get out and enjoy the MANY resort-style pools, beach volleyball court, walking trails, and playgrounds...I could go on and on, but come and check it out yourself!!!

8226 Bayview Crossing Drive, Winter Garden

4 Beds 3.5 Baths Heritage/Plant Street SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. Your search is over! Located in the golf cart district of Winter Garden and just minutes from the Historic Downtown Winter Garden this home offers a rare opportunity. Heritage at Plant is a lovely community that has wonderful amenities such as a delightful pool with covered seating at the pool house in close proximity to the home. The home is situated on a corner lot with a large driveway. As you walk up to this home you will appreciate the covered front porch. The white kitchen cabinets and stainless steel appliances make the home feel bright and airy. The owner's suite is conveniently located on the first level of the home and all other bedrooms are upstairs. This home is immaculate and the perfect opportunity for anyone wanting to live in the downtown area. The sliding doors have plantation shutters and the covered lanai with extended pavers is the perfect place to unwind after a long day. The backyard has been fenced in. Bring your golf cart over or take a lovely walk to Downtown Winter Garden less than half a mile away. Enjoy the local boutiques, and local craft brewery, and explore the Farmer's Market on a Saturday morning. With various fine dining options and local coffeehouses, it's no wonder everyone keeps on coming back to experience all this Historic Downtown has to offer. When you're finished with the shops and farmer's market check out the award-winning West Orange Trail. With close proximity to highways, airports, and attractions, there has never been a better moment to make it yours. Don't delay, schedule your showing today!

781 Orange Belt Loop, Winter Garden

5 Beds 4.5 Baths Lakeview Preserve SubDv. 34787 Zip Code
Under Construction. At Pulte, we build our homes with you in mind. Every inch was thoughtfully designed to best meet your family’s needs, making your life better, happier and easier. The new construction expansive Yorkshire home design is a master at utilizing space by providing ample closets in every bedroom, conveniently located storage and linen closets throughout the home, additional storage in the garage and a large open-concept entertaining space. Yorkshire enjoys a prime location near the amenity center, an oversized lot with an open green backyard, and features 5 bedrooms, 4 full bathrooms, a powder room, two flex rooms, a covered lanai, spacious loft and a 2-car garage. Upon entry, you'll find a guest bedroom featuring an en-suite bathroom with walk-in shower and walk-in closet. Moving toward the living area, you'll find an open flex space – perfect as an office or additional entertaining space, the powder room, defined café area, gathering room with upgraded sliding pocket doors letting in a ton of natural light, your gourmet open kitchen with built-in appliances, walk-in corner pantry, large island, 42” soft-close white Lillian cabinetry with black hardware, Gray Picket tile backsplash, gorgeous Pearl Jasmine quartz counters, coordinating wood canopy hood and pendant lighting pre-wiring - all showcasing the 22-foot covered lanai. There is also a secondary flex room on the first floor. The second floor features a spacious loft, upgraded laundry room, 3 bedrooms – one with an en suite bathroom and walk-in closet, the fourth bathroom, and your owner's suite - which boasts a large walk-in closet, linen closet and en suite bathroom featuring an extended dual-sink double Pearl Jasmine quartz-topped vanity with white Lillian cabinets and matte black hardware, private water closet, and super shower. Professionally curated designer finishes include 8-foot interior doors, white cabinets with quartz countertops and a utility sink in the laundry room, pocket sliding glass doors at the gathering room, upgraded 42" soft-close white Lillian cabinetry with black hardware and quartz countertops, tile accents in the kitchen and bathrooms, Forest Liana porcelain tile flooring in the bathrooms, laundry room and main first floor living areas, soft, stain-resistant Ornamental Gate carpet in the bedrooms and second floor living areas, outdoor kitchen pre-plumbing and so much more! This is one of the final opportunities to own your dream home in Lakeview Preserve so visit today! Lakeview Preserve in Winter Garden offers new homes in a gated location that can't be beaten, featuring fabulous community amenities such as a fitness center, resort style pool with splash pad and cabana, clubhouse, playground, picnic area, kayak launch to Johns Lake, no CDD fee, and all home designs are pre-wired for Smart Home Technology. Lakeview Preserve is only 5 miles to Downtown Winter Garden and 10 minutes from SR 429, which connects to all main thoroughfares, making your daily commute easier.

3275 Buoy Circle, Winter Garden