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.

Filter Results

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... Read More

View Details

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

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

View Details

Courtesy of Property Investment Brokers
  • $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... Read More

View Details

Courtesy of Premier Sothebys Int'l Realty
  • $2,950,000
  • Single Family Home
  • 1
  • 1,152
  • 2
  • 1,718
  • 1963
  • O5535452

Welcome To Your Private Little Compound Nestled On Over 8.4+/- Acres With 131' Of Frontage On Lake Lartigue. Surround Yourself With Nature Creating Your Custom Lakefront Estate Home, While Still... Read More

View Details

Courtesy of Premier Realty Partners Inc
  • $2,950,000
  • Residential Development
  • O5525027

Welcome To Horizon West Village F Phenomenal Growth With 6 New Communities Surrounding Lake Cypress Nursery Bordering Lake Lartigue. Current Zoning Allows Townhomes, Single Family Homes, Prep/charter... Read More

View Details

Courtesy of Premier Realty Partners Inc
  • $2,650,000
  • 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,... Read More

View Details

Courtesy of Keller Williams Classic Iii Re
  • $1,600,000
  • Single Family Home
  • 6
  • 5,548
  • 5
  • 8,614
  • 2007
  • Signature Lakes Prcl 01c
  • O5487567

The Most Incredible Home I Have Ever Seen In This Price Range - Every Luxury And Upgrade Available Has Been Used To Create This Masterpiece - You Must See It To Really Appreciate The Quality And Lake... Read More

View Details

Courtesy of Vintage Realty Group Llc
  • $1,553,180
  • 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... Read More

View Details

Courtesy of Standard Pacific Of Tampa
  • $1,495,000
  • 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... Read More

View Details

Courtesy of Stockworth Realty Group
  • $1,350,000
  • Single Family Home
  • 6
  • 5,572
  • 5
  • 7,442
  • 2017
  • Summerlake
  • O5517132

Builder’s Display Model Home Is Now For Sale Fully Upgraded. Directly On Lake Hancock With Its Own Boat Dock. This Is A 2-story Home. Open, Two-story Family Room For Relaxing And Entertaining;... Read More

View Details

Courtesy of K Co
  • $1,350,000
  • Single Family Home
  • 5
  • 4,316
  • 4
  • 6,040
  • 2017
  • Signature Lakes Ph 02 A B H I J
  • O5537210

*****pre Construction To Be Built***** Davila Homes Offers This Modern, Brand-new Waterfront Creation On Lake Hancock. This Stunning One-story, Custom-built Home Boasts An Open Floor Plan, Volume... Read More

View Details

Courtesy of Premier Sothebys Int'l Realty
  • $1,350,000
  • Single Family Home
  • 7
  • 5,168
  • 5
  • 6,489
  • 2017
  • Signature Lakes Ph 02 A B H I J
  • O5531121

***under Construction, Expected Completion Date Is 8/30/2017*** Introducing This Brand New Unique Waterfront Estate On Lake Hancock. This Masterpiece Estate Offers Open Floor Plan With Volume... Read More

View Details

Courtesy of Premier Sothebys Int'l Realty
  • $1,333,220
  • Single Family Home
  • 4
  • 4,468
  • 5
  • 2014
  • Hickory Hammock
  • T2825745

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, Master Bedroom With Balcony Overlooking Johns... Read More

View Details

Courtesy of Standard Pacific Of Tampa
  • $1,299,000
  • Single Family Home
  • 5
  • 4,613
  • 5
  • 5,997
  • 2004
  • Stoneybrook West Unit 02 46/55
  • O5542427

This Elegant Lakefront European Architectural Style Custom Home Has Been Completely Remodeled. The Home Is Run Almost Entirely On Solar Energy And Is Beautifully Sited For With Lovely Water Views. ... Read More

View Details

Courtesy of Premier Realty Partners Inc
  • $1,249,000
  • Single Family Home
  • 5
  • 4,929
  • 5
  • 6,720
  • 2015
  • Overlook At Hamlin/west Lake Hancock Estates
  • O5546092

This Amazing Lakefront Home On Lake Hancock Has Direct Water Access To Hamlin's Future Town Center. This Spectacular Home Features Five Bedrooms, Four-and-a-half Baths, A Theater Room, Game Room,... Read More

View Details

Courtesy of Premier Sothebys Int'l Realty
  • $1,200,000
  • 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... Read More

View Details

Courtesy of Century 21 Professional Group Inc
  • $1,200,000
  • 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... Read More

View Details

Courtesy of Century 21 Professional Group Inc
  • $1,190,000
  • Single Family Home
  • 6
  • 4,977
  • 6
  • 6,578
  • 2014
  • Signature Lks-pcl 01d Ph 02
  • O5508068

Welcome To Your Luxury Dream Home! From The Moment You Approach The Driveway You'll Be Thoroughly Impressed By The Grand Stature Of This Magnificent Property. Located On An Oversized Lot With Private... Read More

View Details

Courtesy of Engel & Volkers Clermont
  • $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... Read More

View Details

Courtesy of Standard Pacific Of Tampa
  • $1,100,000
  • Single Family Home
  • 4
  • 4,373
  • 5
  • 5,621
  • 2006
  • Johns Cove 43/104
  • O5538568

Here Is Your Opportunity To Own Your Piece Of Paradise. Located In The Custom Home Community Of Johns Cove. This Lakefront Home On Johns Lake Is Ideal For Entertaining Inside And Out And Will Be A... Read More

View Details

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

Pre-construction. To Be Built - Available December 2018! 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.... Read More

View Details

Courtesy of Orlando Tbi Realty Llc
  • $1,099,990
  • Single Family Home
  • 4
  • 5,174
  • 7
  • 6,363
  • 2011
  • Lake Roberts Lndg E
  • O5540141

Wow, What A View In The Heart Of Winter Garden! Enjoy This 6 Bedroom (2 Master Suites), 4 Bathroom, Bonus, Theater, Saltwater Pool,heated Spa And Summer Kitchen Area, Lake Front Home With Dock... Read More

View Details

Courtesy of Re/max 200 Realty
  • $1,099,000
  • Single Family Home
  • 7
  • 4,914
  • 6
  • 7,163
  • 2013
  • Signature Lks-pcl 01d Ph 02
  • O5543207

Lakefront Home!!!! An Elevated Living Experience Awaits In One Of Florida's Most Prominent Locations. Featuring An Exquisitely Appointed Living Space, Set On Over 1 Acre With Panoramic Views Of Famed... Read More

View Details

Courtesy of Adepta Realty
  • $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... Read More

View Details

Courtesy of Stockworth Realty Group
  • $1,066,520
  • 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”... Read More

View Details

Courtesy of Standard Pacific Of Tampa
  • $1,065,000
  • Single Family Home
  • 5
  • 4,163
  • 4
  • 5,364
  • 2015
  • Hickory Hammock Phase 1
  • O5512442

Seller Motivated...lakefront! This Lexington Plan Which Boasts A Majestic View Of Johns Lake, Located In The Community Of Hickory Hammock Community. Your Day Begins To Melt Away As You Drive Through... Read More

View Details

Courtesy of Keller Williams At The Lakes
  • $1,044,547
  • Single Family Home
  • 6
  • 4,468
  • 5
  • 2017
  • Hickory Hammock Emerald Pointe
  • T2901476

Under Construction. To Be Built. Brand New Lakefront Home On John's Lake. This Home Sits On An Oversized Corner Homesite. Oversized Kitchen With Double Islands, 42 In Upgraded Light Cabinets,... Read More

View Details

Courtesy of Standard Pacific Of Tampa
  • $1,026,544
  • 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... Read More

View Details

Courtesy of Standard Pacific Of Tampa
  • $999,990
  • Single Family Home
  • 4
  • 3,847
  • 5
  • 6,202
  • 2015
  • Hickory Hammock
  • O5510947

Gorgeous Lake Front Model Home Filled With Amazing Upgrades Throughout! This Open Concept Plan Home Has Many Great Layout Features Including Formal Dining Space, Private 1st Floor Guest Room With... Read More

View Details

Courtesy of Keller Williams Advantage Rlty
  • $999,950
  • Single Family Home
  • 6
  • 5,345
  • 5
  • 2016
  • Overlook At Hamlin
  • O5514085

Live The Lake Life With This Beautiful Lake Front Home That Sits On Lake Hancock! Enjoy Boating, Skiing, Fishing Or Just Enjoying The View. Next To The Future Town Center In Horizons West. Builder... Read More

View Details

Courtesy of Taylor Morrison Realty Of Fl Inc

Ask Orlando Home Direct

Got Questions? Ask Our Real Estate Experts!

Please complete the form below to ask a question. We'll be glad to email you back with the answer or leave your telephone number in the message box and we'll call you back. We look forward to talking with you!

Back To Top