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Orlando Luxury Homes for Sale By Gary Berkson, RealtorOrlando Luxury Homes for Sale By Gary Berkson, Realtor

GARY BERKSON, REALTOR® | (407) 920-0206 | Email Me

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Winter Garden, FL Homes for Sale

Just Listed Homes for Sale in Winter Garden


Click on the homes below to see the newest homes for sale in Winter Garden listed in the last 7 days.

This beautiful remodeled home in downtown Winter Garden is waiting just for you! Experience the perfect combination of convenience, charm, and peace of mind in this wonderfully maintained 2-bedroom, 1-bath home, offering 836 sq. ft. of thoughtfully designed living space, just a 10-minute walk to vibrant downtown. Step inside to find an updated kitchen featuring granite countertops, stainless steel appliances, and ample cabinetry, perfect for everyday meals or entertaining friends. The bright and inviting interior is complemented by an enclosed back porch, ideal for morning coffee or relaxing with a good book. The fully fenced backyard with lighting creates the perfect setting for evening gatherings, weekend barbecues, or quiet outdoor enjoyment. Outside, the freshly painted exterior and new landscaping add exceptional curb appeal. A garage with electric and a refrigerator, plus a covered parking spot, ensures both convenience and extra storage. This home isn’t just move-in ready, it’s worry-free! The roof, plumbing, and electrical systems were professionally inspected in July 2025 and are all in great condition, and a termite bond with Massey adds even more security. Additional updates like central air and new windows (2010) make this home efficient and comfortable year-round. Best of all, you’re just steps away from downtown’s farmers markets, community festivals, live music events, and local dining. Spend your weekends exploring boutique shops, enjoying outdoor markets, or connecting with neighbors at one of the many community events, all within a short walk from your front door. Located close to amazing schools, major highways and less than 30 minutes from Central Florida's top attractions like Disney World and Universal Studios, you can enjoy that small town charm while being close to all the fun Central Florida has to provide. If you’ve been searching for a home that offers modern upgrades, low-maintenance living, and an unbeatable location, this is the one. Don't wait on this gorgeous home, schedule your private showing TODAY!!! $289,000 Active

215 Pennsylvania Avenue Winter Garden, Florida

2 Beds 1 Baths 836 SqFt 0.16 Acres

Charming 3 Bedroom, 2 Bath Home with Modern Upgrades & Prime Location.
Step into this beautifully updated home featuring 3 spacious bedrooms and 2 full bathrooms. The open floor plan is enhanced by soaring volume ceilings and stylish luxury vinyl plank flooring, with brand new carpet in the bedrooms for added comfort. The heart of the home is the open-concept kitchen, seamlessly connected to the living and dining areas- perfect for entertaining guests or enjoying family time. Enjoy peaceful backyard views with no rear neighbors, offering extra privacy and tranquility. Relax on the back porch and unwind after a long day in your own private retreat. Located in a low HOA community, this home is just minutes from Winter Garden Village, top-rated schools, restaurants, shopping, and more, combining convenience with comfort. Don't miss this opportunity to own a move-in ready home in one of the area's most desirable locations! Schedule your private showing today! $379,000 Active

13108 Social Lane Winter Garden, Florida

3 Beds 2 Baths 1,318 SqFt 0.16 Acres

Under Construction. Waterleigh presents the Bellmore. This amazing one-story home has an elevated designed with elegant exteriors and high-end features. This spacious all concrete block construction single-family home features 4 bedrooms and 3 baths with 2,113 square feet.

 A beautiful front patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a large pantry for extra storage. This gourmet kitchen features quartz countertops, stainless steel appliances and crown molding cabinetry.

Bedroom one, located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with double bowl vanity, and spacious shower/tub space as well as a walk-in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall a drop zone welcomes you from the garage where you will find a fourth bedroom and full bathroom.

This home features living areas fit all your needs. Like all homes in Waterleigh, the Bellmore includes smart home technology which allows you to control your home with your smart device while near or away. 


*Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.* $830,711 Active

11069 Hollow Bay Drive Winter Garden, Florida

4 Beds 3 Baths 2,113 SqFt 0.29 Acres



Quick Facts

Population (2019): 43,648
Zip Codes: 34778, 34787
Median Listing Price: $500,600
Median Closing Price: $484,000
County: Orange County
School District: Orange County Public Schools

Travel & Commute Times

Lake Mary: 42 mins
Lake Nona: 34 mins
Longwood: 38 mins

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Winter Garden FL Real Estate Market Data

Pricing your property to sell right in today’s market is an important process. Our market analysis includes data on recent sales and current market trends as well as local demographics. Click the full report to get the full details on Winter Garden and sign up for a monthly report to be delivered to right to your email inbox.


Virtual Open Houses in Winter Garden

Explore upcoming Virtual Open Houses in Winter Garden by clicking the images below.


About Winter Garden, FL

Winter Garden, just 14 miles outside of Downtown Orlando, used to be called Beulah – but it’s come a long way since its founding in 1857. This beautiful community, on the south end of Lake Apopka, is known as the commercial and cultural capital of West Orange County. It’s teeming with amenities, including the Garden Theatre, the SoBo Gallery and Art Center, numerous museums and all the shopping and dining experiences you need. Known for its “old Florida” charm and its historic downtown area, this community is a wonderful place to live.

Commute Time to Orlando and Nearby Cities

Winter Garden is 15 miles west of Orlando, and it’s 25 miles northwest of the Orlando International Airport. It’s also close to a number of other communities, including:

  • 7 miles from Windermere
  • 22 miles from Mount Dora
  • 26 miles from Longwood
  • 29 miles from Lake Nona
  • 30 miles from Lake Mary
  • 37 miles from Sanford

Winter Garden Homes for Sale

Explore the newest Winter Garden homes for sale by clicking on the images below.

This beautiful remodeled home in downtown Winter Garden is waiting just for you! Experience the perfect combination of convenience, charm, and peace of mind in this wonderfully maintained 2-bedroom, 1-bath home, offering 836 sq. ft. of thoughtfully designed living space, just a 10-minute walk to vibrant downtown. Step inside to find an updated kitchen featuring granite countertops, stainless steel appliances, and ample cabinetry, perfect for everyday meals or entertaining friends. The bright and inviting interior is complemented by an enclosed back porch, ideal for morning coffee or relaxing with a good book. The fully fenced backyard with lighting creates the perfect setting for evening gatherings, weekend barbecues, or quiet outdoor enjoyment. Outside, the freshly painted exterior and new landscaping add exceptional curb appeal. A garage with electric and a refrigerator, plus a covered parking spot, ensures both convenience and extra storage. This home isn’t just move-in ready, it’s worry-free! The roof, plumbing, and electrical systems were professionally inspected in July 2025 and are all in great condition, and a termite bond with Massey adds even more security. Additional updates like central air and new windows (2010) make this home efficient and comfortable year-round. Best of all, you’re just steps away from downtown’s farmers markets, community festivals, live music events, and local dining. Spend your weekends exploring boutique shops, enjoying outdoor markets, or connecting with neighbors at one of the many community events, all within a short walk from your front door. Located close to amazing schools, major highways and less than 30 minutes from Central Florida's top attractions like Disney World and Universal Studios, you can enjoy that small town charm while being close to all the fun Central Florida has to provide. If you’ve been searching for a home that offers modern upgrades, low-maintenance living, and an unbeatable location, this is the one. Don't wait on this gorgeous home, schedule your private showing TODAY!!! $289,000 Active

215 Pennsylvania Avenue Winter Garden, Florida

2 Beds 1 Baths 836 SqFt 0.16 Acres

Charming 3 Bedroom, 2 Bath Home with Modern Upgrades & Prime Location.
Step into this beautifully updated home featuring 3 spacious bedrooms and 2 full bathrooms. The open floor plan is enhanced by soaring volume ceilings and stylish luxury vinyl plank flooring, with brand new carpet in the bedrooms for added comfort. The heart of the home is the open-concept kitchen, seamlessly connected to the living and dining areas- perfect for entertaining guests or enjoying family time. Enjoy peaceful backyard views with no rear neighbors, offering extra privacy and tranquility. Relax on the back porch and unwind after a long day in your own private retreat. Located in a low HOA community, this home is just minutes from Winter Garden Village, top-rated schools, restaurants, shopping, and more, combining convenience with comfort. Don't miss this opportunity to own a move-in ready home in one of the area's most desirable locations! Schedule your private showing today! $379,000 Active

13108 Social Lane Winter Garden, Florida

3 Beds 2 Baths 1,318 SqFt 0.16 Acres

Under Construction. Waterleigh presents the Bellmore. This amazing one-story home has an elevated designed with elegant exteriors and high-end features. This spacious all concrete block construction single-family home features 4 bedrooms and 3 baths with 2,113 square feet.

 A beautiful front patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a large pantry for extra storage. This gourmet kitchen features quartz countertops, stainless steel appliances and crown molding cabinetry.

Bedroom one, located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with double bowl vanity, and spacious shower/tub space as well as a walk-in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall a drop zone welcomes you from the garage where you will find a fourth bedroom and full bathroom.

This home features living areas fit all your needs. Like all homes in Waterleigh, the Bellmore includes smart home technology which allows you to control your home with your smart device while near or away. 


*Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.* $830,711 Active

11069 Hollow Bay Drive Winter Garden, Florida

4 Beds 3 Baths 2,113 SqFt 0.29 Acres

You can also search all Winter Garden homes for sale.

Find Winter Garden New Construction Homes for Sale

Explore Winter Garden new construction homes by scrolling through the images below.

Under Construction. Waterleigh presents the Bellmore. This amazing one-story home has an elevated designed with elegant exteriors and high-end features. This spacious all concrete block construction single-family home features 4 bedrooms and 3 baths with 2,113 square feet.

 A beautiful front patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a large pantry for extra storage. This gourmet kitchen features quartz countertops, stainless steel appliances and crown molding cabinetry.

Bedroom one, located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with double bowl vanity, and spacious shower/tub space as well as a walk-in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall a drop zone welcomes you from the garage where you will find a fourth bedroom and full bathroom.

This home features living areas fit all your needs. Like all homes in Waterleigh, the Bellmore includes smart home technology which allows you to control your home with your smart device while near or away. 


*Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.* $830,711 Active

11069 Hollow Bay Drive Winter Garden, Florida

4 Beds 3 Baths 2,113 SqFt 0.29 Acres

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. $5,995,000 Active

13377 Lake Butler Boulevard Winter Garden, Florida

5 Beds 6 Baths 6,000 SqFt 12.42 Acres

Under Construction. Waterleigh presents the Cordale. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the home you’ll find a downstairs powder room and laundry room complete with doors for privacy. The well-appointed kitchen overlooks the family room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one-bathroom impresses with double bowl vanities, toilet room with privacy door, shower/tub space, and spacious walk in closet. As we head up to the second floor, we are greeted with a loft area and two additional bedrooms. The upstairs bedrooms share a bathroom and linen closet for extra storage. This home features a two-car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterleigh, the Cordale includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. 

*Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.* $568,950 Active

11834 Shine View Lane Winter Garden, Florida

3 Beds 3 Baths 2,027 SqFt 0.12 Acres

Winter Garden Condos for Sale

Check out Winter Garden condos for sale by clicking on the images below.

Easy to show!! Come One, Come All! This is perfect for a family or anyone looking to use as an investment home. This beautiful home comes FULLY FURNISHED with really thought-out details to make you feel right at home. The Community also offers TONS of recreational items to choose from: You can choose from relaxing at the spa, working out in one or both of the two fitness centers provided. 3 swimming pools with food and drink service, mini golf, a lazy river, and a variety of much more. Come take a look at this one before its gone! $320,000 Active

14501 Grove Resort 3708 Winter Garden, Florida

3 Beds 2 Baths 1,396 SqFt 0.3 Acres

One or more photo(s) has been virtually staged. --$100K Renovation just completed, Winter Garden Gem, unlike any other condo in the community!  Welcome to your dream condo in the charming Townhomes of Winter Garden—where everything is brand new, from the floor joists & spray insulation to the ceiling!  This fully renovated single-story end-unit is tucked away at the end of a quaint cul-de-sac and has never been lived in since the transformation was completed.  Step inside and be wowed by the thoughtful redesign and modern upgrades throughout.  What’s new?  Just about everything!  Enjoy new flooring, new roof, new plumbing, new electrical, fresh new walls, new textured ceilings with recessed lighting & a sleek ceiling fan, and energy-efficient windows.  The brand new split HVAC system and updated electrical panel provide year-round comfort and peace of mind.  The kitchen is a standout feature, redesigned with all-new stylish cabinetry featuring soft-close drawers and doors, new stone counters, a new black and stainless steel dishwasher, a deep sink, and a new range installed in late 2024.  The black refrigerator, just a few years old, completes the modern look with a coordinated and functional design, perfect for everyday living and entertaining.  The bathroom has been beautifully reimagined with a spacious walk-in tiled shower, stone-topped vanity, and contemporary finishes.  Additional upgrades include a new laundry area with a washer and dryer replaced just a few years ago, a bonus storage closet, new exterior stucco, a new front door with an electronic lock, and more.  Enjoy assigned parking and relax at the community pool, all just minutes from everything downtown Winter Garden has to offer—including Crooked Can Brewery, local dining, boutique shopping, farmers markets, and live entertainment.  This is your chance to own a completely turnkey, never-lived-in condo in one of Central Florida’s most sought-after communities! $137,500 Active

416 Eron Way 30 Winter Garden, Florida

1 Beds 1 Baths 420 SqFt 0.01 Acres

This beautiful 4-bedroom, 3-bathroom townhouse in Winter Garden's Summerlake community is move-in ready and spans 1,853 square feet. The home features high ceilings throughout and an open great room concept that seamlessly connects the dining and family rooms to a gourmet kitchen.

The kitchen is a real highlight with 42-inch cabinets topped with crown molding, Level 4 quartz counters, and a wainscot kitchen island wall. You'll love the built-in refrigerator panels, pendant lighting, under cabinet tape lighting, and stainless steel appliances that make cooking a pleasure.

The primary bedroom suite bathroom offers quartz counters and an oversized separate shower with frameless glass for a spa-like experience. Step outside to your spacious and private fenced rear brick courtyard and green space, perfect for relaxing or entertaining. The property includes a detached 2-car garage with epoxy finish and keyless entry.

Living in Summerlake means enjoying 29 acres of parks where you can fish off the deck. The community clubhouse features a gym and rec room, plus there's tennis and basketball courts, a zip line, walking paths, and a resort-style pool with zero entry splash pad. Kids will love the playground, and pets can enjoy the dog park.

Your HOA fee covers lawn care, exterior building maintenance, and pest prevention. The location is incredibly convenient, with easy access to SR429, Publix, Starbucks, OC National Golf Center, Cineopolis, and numerous restaurants including Bosphorous, French Cafe, and the Great Greek. $455,000 Active

15420 Blackbead Street Winter Garden, Florida

4 Beds 3 Baths 1,853 SqFt 0.1 Acres


Schools in Winter Garden

Kids living in Winter Garden are part of Orange County Public Schools. There are charter and private schools in the community, as well as in nearby communities, for families that want to pursue those routes.


Winter Garden Elementary Schools

  • Cavalry Christian School (private)
  • Cranium Academy (private)
  • Dillard Street Elementary
  • Family Christian School (private)
  • Foundation Academy (private)
  • Independence Elementary
  • Lake Whitney Elementary
  • Sunridge Elementary
  • Tildenville Elementary
  • UCP West Orange Charter
  • Whispering Oak Elementary
  • William S. Maxey Elementary

Winter Garden Elementary Schools

  • Cavalry Christian School (private)
  • Cranium Academy (private)
  • Dillard Street Elementary
  • Family Christian School (private)
  • Foundation Academy (private)
  • Independence Elementary
  • Lake Whitney Elementary
  • Sunridge Elementary
  • Tildenville Elementary
  • UCP West Orange Charter
  • Whispering Oak Elementary
  • William S. Maxey Elementary

Winter Garden High Schools

  • Calvary Christian School (private)
  • Esteem Academy
  • Foundation Academy (private)
  • Orange Technical College Westside Campus
  • Lillie V High School (private)
  • Vision Educational Learning Center (private)
  • West Orange High School

Dining, Shopping, and Entertainment in Winter Garden

You’ll find a handful of great restaurants in Winter Garden ranging from big chains to locally owned eateries. Whether you’re looking for a farm-fresh restaurant with classic American fare or international cuisine, there are several restaurants along West Colonial Drive, just off the turnpike, and along Plant Street. There are a number of great restaurants along the Daniel Webster Western Beltway, as well.

There are indoor and outdoor shopping malls in Winter Garden that carry all the big-name brands, including Winter Garden Village. You’ll also find Target, Walmart and Publix, as well as other major retailers, alongside locally owned stores and specialty boutiques. The farmers market convenes every Saturday morning, enabling you to buy locally grown produce, honey and a variety of homemade items as well.

The Cinéopolis Luxury Cinema, museums, libraries, and a number of other attractions are also located in Winter Garden. The community also holds several events throughout the year, including 4th of July festivities, parades and holiday celebrations during winter. In addition to indoor attractions, the area is teeming with outdoor recreational opportunities on and off Lake Apopka.


Restaurants in Winter Garden


Things to do in Winter Garden



Golf in Winter Garden

The West Orange Country Club and the Orange County National Golf Center and Lodge are located right in Winter Garden. There are several other noteworthy facilities, courses and clubs in the area, as well, including:

  • Sik Golf
  • Orange County National Driving Range
  • Forest Lake Golf Club
  • Isleworth Golf and Country Club
  • Golden Bear Club


Find Winter Garden Homes for Sale With an Area Expert Today

If you’re looking for a home for sale in Winter Garden, call us at 407-920-0206 or contact us online. We update our online listings every hour, as well, so please feel free to explore our site to look for your dream home. We’re here to help you find the perfect place to live in Winter Garden, so call us or reach out to us online today so we can start searching!

Contact Me Now

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(407) 920-0206
grberkson@gmail.com

Lake Mary, FL 32746

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