Winter Garden Properties

None other than former U.S. President Chester A. Arthur quipped that Winter Garden was the most beautiful city in the Sunshine State. That certainly says a lot, considering the state is home to miles of scenic coastlines.

However, the former president was certainly on to something. Winter Garden is beautiful, thanks in part to a richly historic downtown district. Arts, culture and dining are right on your doorstep, making it a vibrant place to reside.

The Facts on Winter Garden, Florida

Winter Garden is located west of Orlando, and it is found in Orange County. The total population of Winter Garden is approximately 35,000. However, it also falls within the Orlando-Kissimmee-Sanford Metropolitan Statistical Area, where the total population is a staggering 2.3 million.

Winter Garden has a warm and subtropical climate, making it a desirable place to live for those who enjoy sunny skies and an absence of extreme cold, even in the winter. Although Winter Garden grew as a direct result of the citrus industry, it is know better known for its downtown, its shops, its historic architecture and its ideal location.

Winter Garden and the Local School System

The city of Winter Garden falls within the Orange County Public School System, one of the best in the state. The city offers six public elementary schools to its youngest residents, and these are Dillard Street Elementary, Lake Whitney Elementary, Maxey Elementary, Tildenville Elementary, Whispering Oak Elementary and Sunridge Elementary.

The three public middle schools are Sunridge Middle, Bridgewater Middle and Lakeview Middle. One of the two public high schools is West Orange High, and the other is Westside Tech, where students can take technology classes as electives. You'll also find charter schools, private schools and special needs schools to ensure that all students are properly catered to.

What Makes Winter Garden Such a Special Place to Live?

One of the best things about living in this remarkable city is having Downtown Winter Haven right on your doorstep. You can tour art museums or admire outdoor sculpture gardens, or you might stroll along the sidewalks and take in the historic architecture.

Winter Garden also boasts miles of public trails where you can hike or ride a bike and enjoy the wonderful weather of the region. Winter Garden Village is an enormous shopping area with eateries, boutiques and department stores, ensuring you have access to all your everyday needs and more. If you ever crave city life and amenities, they are just a 20-minute drive away from home.

Winter Garden, Florida, is a lakeside city with a historic background and a charming downtown. Whatever your age or your background, you'll fall in love with this delightful destination beloved by its many residents.

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Properties For SaleSold Properties
  • $6,500,000
  • Villa
  • 1
  • 1,088
  • 1
  • 1,088
  • 2009
  • Lake Reedy
  • O5545793

Thinking About Getting Away From The City? Then Envision Yourself Owning Over 155+/- Pristine Acres In The Heart Of Booming Orlando. Rare Opportunity To Own A Piece Of Private Lake Frontage Within The Back Gates Of Walt Disney World. Home To The #1 Tourist Destination Of The World, Walt Disney World Is Your Neighbor While Being Secluded From Everyday Life. Surround Yourself With Mother Nature As... Read More

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Courtesy of Premier Realty Partners Inc
  • $5,000,000
  • Residential Development
  • O5486295

Property Located In :village 1" Of Horizon W Est Master Development Plan.

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Courtesy of Property Investment Brokers
  • $4,395,900
  • Single Family Home
  • 9
  • 11,696
  • 6
  • 23,202
  • 2010
  • Deer Island
  • O5563198

Perfectly Sited On A 1.75 Acre Peninsula With Panoramic Lake Views And Over 700 Feet Of Frontage This Lakefront Estate Presents Classic European Elegance. The Pavered Drive Leads To An Impressive Estate Built With The Finest Materials And Finishes. At The Entry, The Focus Is On Symmetry Of Design From The Stone Flooring To The Custom Made Marble Staircase With Wrought Iron Detail. A Series Of... Read More

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Courtesy of Premier Realty Partners Inc
  • $2,995,000
  • Single Family Home
  • 6
  • 6,493
  • 5
  • 14,500
  • 2016
  • Savannah Ridge Sub
  • O5515802

A Paver Drive Leads To This Stunning French Chateau-style Home Nestled In A Gated Community. As You Enter The Estate You Are Greeted By A Gorgeous Double Staircase And Spanish Marble Floors That Span Throughout The Home. Exquisite Details And Quality Features Touch Every Inch Of This Estate. Featuring Five Bedrooms, Six Bathrooms, An Upstairs And Downstairs Living Room, A Formal Room, An Office,... Read More

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Courtesy of Premier Sothebys Int'l Realty
  • $2,500,000
  • Single Family Home
  • 5
  • 8,398
  • 5
  • 12,610
  • 2002
  • Deer Island
  • G4845955

Welcome To Casa Sul Lago, A 1.05 Ac Lakefront Paradise On Deer Island, Featuring Breathtaking Sunsets, Towering Italian Cypress, And An 8400 Sqft Custom Home With A Colossal Multilevel Pool Veranda, 3-car Garage, Detached Guest House, Boathouse And Beachfront. A Circular Driveway And Private Courtyard Entrance Welcomes You To This Home. Inside You Will Find Custom Finishes Such As Crown Molding,... Read More

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Courtesy of Keller Williams Classic Iii Re
  • $1,700,000
  • Single Family Home
  • 6
  • 4,664
  • 5
  • 6,133
  • 2016
  • Lakeshore Preserve
  • O5560459

Toll Brothers Model Home Available Now! The Maranello Model Will Not Disappoint. This Award Winning Home Sits On A Waterfront Lot With A Stunning Infinity Edge Pool To Complement Your Lake View. The Elegant Foyer Opens To The Expansive Great Room. The Living Space Is Beautifully Finished And Includes A Well-designed Kitchen With A Large Center Island And A Walk-in Pantry. Your Kitchen Overlooks... Read More

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Courtesy of Orlando Tbi Realty Llc
  • $1,590,000
  • Single Family Home
  • 4
  • 4,978
  • 6
  • 7,256
  • 2015
  • Signature Lks-pcl 01d Ph 02
  • O5569198

This Immaculate Lakefront, Mediterranean Style 2-story Home With A Contemporary Flare Comes Fully Equipped With A Rear Private Covered Lanai, Cabana, And Summer Kitchen That Allows Endless Entertainment And Exudes Modern Elegance. With 6 Bedrooms, 4 Baths, A Game Room, A Private Office With A Closet, A Theater Room, Generous Living Space, Stylish Finishes, And Spectacular Lake Views And Sunsets... Read More

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Courtesy of Charles Rutenberg Rlty Orlando
  • $1,569,750
  • Single Family Home
  • 4
  • 4,177
  • 4
  • 2016
  • Waterside
  • T2843783

Brand New Single Story Lakefront Home In Beautiful Waterside Community Overlooking Johns Lake, In Winter Garden!! Upgrades And Features Include: Hardwood Floors Throughout Main Living Areas, Gourmet Kitchen With Stainless Steel Appliances, Home Theatre, Wet Bar, Fireplace In Great Room, Pool Bath, Tray Ceilings, Pre-wire For Pool And Summer Kitchen. Waterside Is Situated On John’s Lake, Less... Read More

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Courtesy of Standard Pacific Of Tampa
  • $1,499,000
  • Single Family Home
  • 5
  • 4,880
  • 5
  • 6,493
  • 2000
  • Isles Lake Hancock
  • O5555992

Market Adjustment! Newly Remodeled With A Fresh, Contemporary Look Inside And Out. This Home Is Model Perfect And The Lakefront Lot Is One Of The Largest In The Community. Showcasing Detailed Finishes Throughout, Including Granite Countertops, Crown Molding And Hardwood Floors, The Functional Floor Plan Balances Customary Architecture With A Very Open Plan Ideal For Family Living. The Kitchen,... Read More

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Courtesy of Premier Sothebys Int'l Realty
  • $1,345,000
  • Single Family Home
  • 5
  • 5,212
  • Independence
  • 7
  • 7,932
  • 2012
  • Signature Lks-pcl 01d Ph 02
  • O5566042

Retreat To Your Own Lakefront Resort Complete With Nightly Disney Fireworks And Tranquil Sunsets On The Shores Of Beautiful Lake Hancock, Soon To Be One Of A Very Few Lakes In Central Florida Where You Can Boat To Boardwalk Boutiques, Dine At A Luxury Movie Theater Or Fine Waterfront Restaurant. This Custom 7-bedroom, 5 Bath Home Boasts A Spacious Gourmet Kitchen Complete With Ge Monogram... Read More

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Courtesy of Waypoint Real Estate Group Inc
  • $1,250,000
  • Single Family Home
  • 4
  • 3,578
  • Preserve At Avalon
  • 4
  • 5,510
  • 2019
  • Preserve At Avalon
  • O5561795

Pre-construction. To Be Built. *home Shown Is For Informational Purposes Only* This 4 Bd/3.5ba Retreat Is Situated Among Beautiful Rolling Hills In The Horizon's West Area. The Preserve At Avalon Boasts A Beautiful, Mature Pine Forest, Perfect For Those Seeking An Upscale Home With Plenty Of Privacy. Imagine Entering A Spacious Foyer Opening To Your Private Gallery And Wine Cellar To Your... Read More

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Courtesy of Waypoint Real Estate Group Inc
  • $1,246,000
  • Single Family Home
  • 4
  • 4,408
  • 5
  • 6,274
  • 1989
  • None
  • O5508996

Perfectly And Privately Situated On Spring Fed Lake Roper, One Of The Sport's Most Sought After Waterski Lakes In The Nation, This Rare Lakefront Compound Boasts Over 1000 Ft Of Wrap Around Lake Frontage And Spans Over 2.5 Acres Of High And Dry Land. Custom Built By Master Custom Builder Scott Green, This One Story 3-way Split Floorplan Sprawls Across 4408 Sf With 5 Bedrooms, 3.5 Bathrooms And A... Read More

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Courtesy of Stockworth Realty Group
  • $1,200,000
  • Single Family Use
  • Acreage & Unrec
  • O5493908

Opportunity Knocks! Ten Acres With 4/3 Home, 3/2 Mobile Home And Pole Barn; Featuring A Tranquil Private Fishing Pond And Views Of A Ski-friendly Lake. Located Just 10 Minutes From Local Hot Spot Downtown Winter Garden, Walk To Sunridge Elementary And Middle Schools. This Beautiful Property Is Adjacent To The Tucker Ranch Conversion Into A Park And Working Farm Preserving A Piece Of Old... Read More

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Courtesy of Mainframe Real Estate
  • $1,200,000
  • Single Family Home
  • 6
  • 4,498
  • Hickory Hammock
  • 5
  • 6,323
  • 2015
  • Hickory Hammock Ph 1d
  • O5567623

Lake, Lake And More Lake! This House Is Built To Appreciate The Full Lake Frontage It Occupies. Upon Entry, You Will Be Wowed By The Stunning View. But Stop, And First Take In The Expansive Double Foyer, The Huge Separate Formal Dining Room, Downstairs Powder, Balusters And Wooden Flooring. Moving Into The Open Great Room With Triple Sliders, You Will Then Find A Large Kitchen With Double Island,... Read More

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Courtesy of Era Grizzard Real Estate
  • $1,139,492
  • Single Family Home
  • 3
  • 3,362
  • 4
  • 2014
  • Isle Of Lake Hancock
  • T2901556

This One Of A Kind Model Home Is A Must See! Located On A Peninsula That Sits Between Two Ski Lakes, It Is Literally Surrounded By Water On All Sides. This Popular Open Floor Plan Is The Perfect Home For Entertaining! The Outdoor Pool Area Is Complete With Swim Up Bar, Hot Tub, And Recessed Fire Pit. The Outdoor Kitchen Has Views To Not One But Two Lakes. This Spacious Home Is Part Of An... Read More

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Courtesy of Standard Pacific Of Tampa
  • $1,125,000
  • Single Family Home
  • 7
  • 4,896
  • 6
  • 7,184
  • 2016
  • Summerlake Pd Ph 3a
  • O5571866

Gorgeous Like New 6 Bedroom 6.5 Bath Pool Home On Lake Hancock. Separate Formal Living And Dining Rooms Just As You Walk Inside, Then Your Huge Family Room Over Looks The Infinity Pool And Beautiful Lake Outback. Magnificent Chef's Kitchen Opens Up Into The Family Room Making This Home Perfect For Entertaining. Breakfast Nook In The Kitchen Also With Fabulous Lake And Pool Views. One Master... Read More

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Courtesy of Homevest Realty
  • $1,099,995
  • Single Family Home
  • 7
  • 5,368
  • 6
  • 2017
  • Lakeshore Preserve
  • O5490596

Pre-construction. To Be Built - Available Early 2019! Brand New Santa Bella Estate Home By Toll Brothers At Lakeshore. Warm Barrel Tile Roof And Stone Set The Mood For This Tuscan Inspired Home. An Enchanting Two-story Foyer Welcomes You Upon Arrival To This Beautiful Home And Showcases An Eye-catching Staircase With A Clear Line Of Sight Into The Formal Dining Room And Beyond. The Well-designed... Read More

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Courtesy of Orlando Tbi Realty Llc
  • $1,099,000
  • Single Family Home
  • 4
  • 4,766
  • 4
  • 6,450
  • 2014
  • Hickory Hammock Ph 1a
  • O5516180

Stunning, High End Home On One Of The Best Lakefront Lots In Hickory Hammock With No Front Or Rear Neighbors! Incredible Views Of The 2,600 Acre Johns Lake, Where You Can Truly Enjoy The Florida Lifestyle To The Fullest, Be It Boating, Fishing, Water Skiing Or Just Relaxing On Your Covered Lanai Enjoying The Stunning Sunsets Over The Lake. This Certified Energy Efficient Home Which Has Never... Read More

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Courtesy of Bhhs Florida Realty
  • $1,095,000
  • Ranchland
  • Lake Avalon Groves Rep
  • O5563895

This 27.76 Acre Property Is Located In The High Demand Horizon West Area Of Winter Garden; Just Minutes To Downtown Orlando, Disney World, & Universal Studios; 1 Mile North Of The New Town Center; *build Your Dream Compound And Have Your Privacy Too*

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Courtesy of Bar Invest Realty Llc
  • $1,079,000
  • Single Family Home
  • 7
  • 5,412
  • 6
  • 8,388
  • 1999
  • Deer Island
  • G4851539

Price Reduced Below Market Value. Welcome Home To This 1 Acre Lakefront Estate In Secluded Gated Community Of Deer Island. This 5412 Sft Home Sits On 101 Ft Of Direct Johns Lake Frontage And Features 6 Bedrooms, 5 Baths, 2 Half Baths, 4-car Oversize Garage, Private Pool, And A Covered Boat Dock Equipped With 2 Boatlifts, Party Deck, Water & Electricity. Stepping Through The Front Doors You Will... Read More

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Courtesy of Keller Williams Classic Iii Re
  • $1,000,000
  • Residential Development
  • Lake Avalon
  • O5532924

Just Shy Of 10 Acres, Mostly Cleared With A Bonus Two Story Farmhouse Is An Excellent Opportunity For A Homeowner Looking For Acreage. Agricultural Status Is On 7.6 Acres Along With Homestead On The Remainder. The Property Is Perfect For The Builder Looking To Establish A New Community. The Property Does Offer Electric Utility Service Along With A Deeded 30 Ft Easement. The Farmhouse Offers A... Read More

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Courtesy of Century 21 Professional Group Inc
  • $1,000,000
  • Single Family Home
  • 1
  • 1,224
  • 2
  • 1,544
  • 2000
  • Lake Avalon Groves Rep
  • O5532925

Just Shy Of 10 Acres, Mostly Cleared With A Bonus Two Story Farm House Is A Great Opportunity For A Builder Looking For Acreage. Agricultural Status Is On 7.6 Acres Along With Homestead On The Remainder. The Property Is Perfect For A Homeowner Looking To Expand On The Property With No Hoa. The Property Does Offer Electric Utility Service Along With A Deeded 30 Ft Easement. The Farm House... Read More

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Courtesy of Century 21 Professional Group Inc
  • $999,990
  • Single Family Home
  • 4
  • 3,764
  • Preserve At Avalon
  • 4
  • 5,058
  • 2019
  • Preserve At Avalon
  • O5562206

Pre-construction. To Be Built. *home Shown Is For Informational Purposes Only* This 4 Bd/3.5ba Retreat Is Situated Among Beautiful Rolling Hills In The Horizon's West Area. The Preserve At Avalon Boasts A Beautiful, Mature Pine Forest, Perfect For Those Seeking An Upscale Home With Plenty Of Privacy. Imagine Entering A Spacious Foyer Opening To Your Formal Dining Area To Your Right, And... Read More

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Courtesy of Waypoint Real Estate Group Inc
  • $990,000
  • Single Family Home
  • 3
  • 3,359
  • 4
  • 4,647
  • 2017
  • Isles/lk Hancock Ph Iii
  • O5566389

A Stunning Home In An Extraordinary Peninsula Between Two Ski Lakes. This Beautiful Four Bedroom, Three Bath Home Is Located In The Exclusive Gated Million Dollar Community, Isles Of Lake Hancock. (see "virtual Tour" Under "other Interior Features"). This Community Is Famous For Hosting The Annual Worldwide Ski Tournament. A New House With A Contemporary Clean Look Inside. The Community Has... Read More

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Courtesy of Citarelli Realty Group Llc
  • $979,995
  • Single Family Home
  • 5
  • 4,213
  • 4
  • 2016
  • Lakeshore Preserve
  • O5509949

Pre-construction. To Be Built - Available February 2019. Brand New Bramante Tuscan Estate Home By Toll Brothers At Lakeshore. Warm Barrel Tile Roof And Stone Set The Mood For This Tuscan Inspired Home. From The Inviting Covered Front Entry Your Guests Are Welcomed Into A Distinctive Foyer That Opens Up To The Great Room And Adjacent Kitchen. This Open Concept Floor Plans Showcases A Well Light... Read More

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Courtesy of Orlando Tbi Realty Llc
  • $972,000
  • Single Family Home
  • 5
  • 4,475
  • 5
  • 5,618
  • 2015
  • Hickory Hammock Ph 1d
  • O5568879

Why Wait To Build When You Can Have A Beautiful New Waterfront Home With All The Upgrades. This San Marino Model Has 4,475 Square Feet Of Living Area And Is Located On Beautiful Lake Johns. From The Moment You Walk Into The Home, You Notice The Openness Of The Floor Plan Creating The Perfect Environment For Family Gatherings. Elegant Wood Floors Travel Throughout The Interior, From The... Read More

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Courtesy of Realty Executives Central Fl
  • $950,270
  • Single Family Home
  • 6
  • 3,546
  • 4
  • 2014
  • Hickory Hammock
  • T2822929

Builder’s Display Model Home Is Now For Sale. Tons Of Upgrades. Directly On John’s Lake So You Can Build You Own Boat Dock. This Is A Single Story Home With A Bonus Room Upstairs. 42” Espresso Cabinets Throughout The House, Granite Kitchen Countertops, Silestone Bathroom Countertops, Dark Wood Floors Throughout All Common Areas Of Homes. Gourmet Kitchen That Includes Double Ovens And A... Read More

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Courtesy of Standard Pacific Of Tampa
  • $948,000
  • Single Family Home
  • 4
  • 5,996
  • 5
  • 7,586
  • 1974
  • Edgewater Beach Rep 02
  • O5530447

Lovely Secluded, Yet Just Minutes From Historic Downtown Winter Garden, Montverde Academy, Clermont's National Training Center And A Quick 20 Minute Commute To Downtown Orlando! This Vintage Charmer Has 5 Bedrooms And 4 Baths With A Nostalgic Wood Burning Fireplace And A Centrally Located Kitchen With Island And Pass Through To The Amazing 2 Story Entertaining Room With Billiard Table, Library,... Read More

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Courtesy of Premier Realty Partners Inc
  • $929,044
  • Single Family Home
  • 4
  • 3,514
  • 5
  • 2014
  • Hickory Hammock
  • T2822953

Builder’s Display Model Home Is Now For Sale. Tons Of Upgrades. Directly On John’s Lake So You Can Build You Own Boat Dock. This Is A 2-story Home With A Giant Master Bedroom Overlooking Johns Lake., Game Room And 3 Other Bedrooms Upstairs And One Guest Room And Full Bath Downstairs. 42” Maple Cream Kitchen Cabinets With A Hazelnut Glaze. Silestone Kitchen And Bathroom Countertops,... Read More

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Courtesy of Standard Pacific Of Tampa
  • $929,000
  • Single Family Home
  • 7
  • 4,388
  • 5
  • 5,567
  • 2017
  • Canopy Oaks Ph1
  • O5557722

Under Construction -this Home Won The Highest Award In The 2017 Parade Of Homes! Beating All Entries! French Country Architecture And Luxury Appointments Make This 5 Br, 5 Bath, 2 Half Bath, 3-car Garage Delray Pool Home Special And Unique. The Soaring 2-story Foyer With Its Charming Juliette Balcony Provide A Hint Of The Excitement Of This Home's Design. Enter Into The Great Room And Enjoy The... Read More

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Courtesy of Windermere Realty Company Llc

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