Winter Garden

Community Info

  • Price Range:
    $277,000-$3,327,429

ABOUT WINTER GARDEN LUXURY HOMES & REAL ESTATE

The winter wonderland in Florida is a place for people to escape from their busy lives. When you live here, there are many things at your fingertips - all within walking distance or easy driving distance! Whether it's shopping and dining on one side of town with everything else imaginable just waiting outside its borders; enjoying movies under stars while feeling like they're worlds away because nothing can touch them anywhere around these parts- no matter how far sound carries over water surfaces during nighttime hours either way---you'll find what makes this little community so special right before closing up tight every night. Winter Garden is a suburb of Orlando with a population of 45,978. Winter Garden is in Orange County and is one of the best places to live in Florida. Living in Winter Garden offers residents a sparse suburban feel and most residents own their homes.

What is it like to live in Winter Garden?

Winter Garden is a great place to live if you love being outdoors and around nature. While the city welcomes new neighborhoods and businesses, some of the nature preserves are protected. This ensures that the natural beauty will be around for wildlife to thrive and us to enjoy.

What is the demographic of winter garden?

The 5 largest ethnic groups in Winter Garden, FL are White (Non-Hispanic) (48%), White (Hispanic) (17.4%), Black or African American (Non-Hispanic) (13.4%), Asian (Non-Hispanic) (7.44%), and Two+ (Non-Hispanic) (4.63%).

Reasons You Should Buy a Luxury Home in Winter Garden, FL

Location of Winter Garden, FL

Winter Garden gets major brownie points for being in the perfect location! It’s tucked far enough away from the craziness of the theme parks for comfort, but close enough to take advantage of Central Florida’s attractions on a whim. Winter Garden combines stunning real estate, a rich history and a community of locals who live life on purpose. It’s no secret that Winter Garden is the new spot for both busy professionals and growing families.

Community – Living in Winter Garden, FL

Central Florida is known for its theme parks which attract millions of visitors each year. Everyone wants to visit Central Florida for the excitement, warm weather, and Mickey Mouse. Here in Winter Garden, we have a different vibe, we have that small-town feel. The gorgeous real estate, locally owned businesses, beautiful parks, and community events take you away from the hustle and bustle and touristy feel. Here you’ll get to know your neighbors and really build a community. Although Winter Garden became a city in 1908 it doesn’t make a difference if you were born here or have recently moved here. Our little city has been growing over the past decade. Over 10,000 people have moved to Winter Garden since 2010, this is a growth of 37.16%, making it a diverse city for anyone to call home. Here neighbors become friends, kids grow up together, and people wave as they pass by. It’s a place where members value community, inclusion, involvement, and look for opportunities to connect with others.

Education – Schools in Winter Garden, FL

Winter Garden is an extremely family-focused community. People move here because it’s a safe place to raise kids, make friends and enjoy life. It’s a huge plus for families that there are EXCELLENT schools. We’re not just talking about public schools, here, there are a variety of options to fit your family’s needs. Many of the public schools have received awards and are A-rated. Looking for an alternative to the public-school setting? Innovation Montessori is a quickly expanding public charter school in Winter Garden, and families also love Hope Charter and Legacy High School. There are also faith-based private schools like The Foundation Academy. Some Winter Garden families homeschool, some do virtual school. At the end of the day, Winter Garden gives parents the freedom to choose the best educational setting for their child to set them up for success. Winter Garden is also very close to Orlando’s colleges, many of them are only about a 30 min drive. This is great for those with older kids who want to continue their education while saving some money by continuing to live at home. Some of the colleges are Central University of Florida, Rollins College, Florida Technical College, and more.

Neighborhoods – New Developments

New developments are popping up throughout the community. Renowned builders like Ryan Homes and CalAtlantic Homes are making their mark in new neighborhoods, building high-end homes close to Downtown, the trail, and expanding Winter Garden. Neighborhoods give residents upscale options in real estate, offering spacious residences full of upgrades, resort-style amenities, and the security of a gated community. Families who score one of these brand-new homes can enjoy the quiet of the suburbs with the convenience and excitement of being close to downtown. Homes for sale in neighborhoods like Hickory Hammock and Cypress Reserve range anywhere from $300K-$700K and put residents smack in the middle of everything Winter Garden has to offer.

Weather in Winter Garden, FL

Weather is something to keep in mind when deciding where to call home. Lots of people from up north move to Winter Garden to escape the freezing winters. Some have two homes so they can enjoy the warmer winters here and still go back north to avoid the hot and humid summers we have here. Although we do have hot and humid summers here, we frequently have afternoon showers to cool things down. All in all, the weather is nice all year round. Just don’t forget about hurricane season. Winter Garden is centrally located in the state so we avoid most of the damage, but there’s still a change we will have some.

Retire in Winter Garden, FL

You’ve lived a good long life and have worked hard, now it’s time for you to RETIRE! Winter Garden is the perfect place to retire. In fact, the Downtown Winter Garden is as good as it gets. With great weather, beautiful nature, and diverse local restaurants and businesses you’ll always have something to do.

Winter Garden Luxury Homes for Sale by Orlando Best Real Estate

Call Orlando Best Real Estate @ 407.961.8412 for Winter Garden Luxury Homes for Sale. We Have all the MLS Listings for Winter Garden Luxury Homes & the entire Orlando Area.

Orlando Luxury Homes and Communities

7 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
14241 COLONIAL POINTE DRIVE
 $1,390,000 7 / 5
 5,001sf N / Y
15327 HERON HIDEAWAY CIRCLE
 $980,000 7 / 4
 4,267sf N / Y

6 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
14168 LARKSPUR LAKE DRIVE
 $3,327,429 6 / 6
 6,442sf Y / N
16826 BROADWATER AVENUE
 $1,590,000 6 / 5
 4,451sf N / N
10067 AUSTRINA OAK LOOP
 $1,170,000 6 / 5
 4,305sf N / N

5 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
17737 DEER ISLE CIRCLE
 $2,950,000 5 / 3
 4,886sf Y / Y
9014 MORGANA COURT
 $2,350,000 5 / 4
 4,436sf Y / Y
15532 AVENUE OF THE ARBORS
 $2,075,000 5 / 4
 3,837sf Y / Y
7766 MINUTEMEN LOOP
 $1,824,888 5 / 4
 4,716sf Y / N
15606 SHOREBIRD LANE
 $1,699,000 5 / 4
 4,300sf N / Y
16768 SANCTUARY DRIVE
 $1,610,000 5 / 4
 4,258sf Y / Y
10291 ATWATER BAY DRIVE
 $1,299,500 5 / 3
 3,910sf Y / N
16689 TOCCOA ROW
 $1,290,000 5 / 5
 3,458sf N / Y
17850 HITHER HILLS CIRCLE
 $1,199,000 5 / 5
 3,416sf N / N
15625 SYLVESTER PALM DRIVE
 $1,120,000 5 / 4
 3,886sf N / Y
8759 SONOMA COAST DRIVE
 $1,080,000 5 / 5
 3,416sf N / N
8768 SONOMA COAST DRIVE
 $1,025,000 5 / 5
 3,416sf N / N
9207 BUSACO PARK WAY
 $1,000,000 5 / 4
 3,291sf Y / N
9319 BRADLEIGH DRIVE
 $995,000 5 / 4
 3,602sf N / N
9849 LOST CREEK DRIVE
 $990,000 5 / 3
 3,910sf Y / N
14553 DRIFTWOOD COURT
 $945,000 5 / 3
 4,744sf N / Y
13900 LANYARD WAY
 $844,900 5 / 4
 3,687sf N / N
18041 CIDER MILL LANE
 $833,191 5 / 4
 3,225sf N / N
11223 HOLLOW BAY DRIVE
 $829,736 5 / 4
 2,866sf N / N
8807 SONOMA COAST
 $819,000 5 / 4
 2,840sf Y / N
11187 HOLLOW BAY DRIVE
 $814,566 5 / 4
 2,866sf N / N
11229 HOLLOW BAY DRIVE
 $807,201 5 / 4
 3,225sf N / N
14416 TRAVOIS WAY
 $799,000 5 / 4
 3,324sf N / N
13722 FOX GLOVE STREET
 $769,990 5 / 3
 3,082sf N / Y
15583 HAMLIN BLOSSOM AVENUE
 $749,000 5 / 3
 2,817sf N / N
15061 VALVERSE ALLEY
 $720,000 5 / 3
 2,934sf N / N
6151 GLORY BOWER DRIVE
 $689,000 5 / 3
 2,872sf N / N
1209 CASTLEPORT ROAD
 $674,990 5 / 3
 2,812sf Y / N
13900 FOX GLOVE STREET
 $669,000 5 / 3
 3,887sf N / N
12731 GROVEHURST AVENUE
 $660,000 5 / 3
 3,474sf N / N
15143 KIRSTY ALLEY
 $659,000 5 / 3
 2,934sf N / N
14494 BREAKWATER WAY
 $649,000 5 / 3
 3,638sf N / N
14464 WHITTRIDGE DRIVE
 $640,000 5 / 3
 2,835sf N / N
915 WESTCLIFFE DRIVE
 $630,000 5 / 3
 2,868sf N / N
813 MARSH REED DRIVE
 $609,000 5 / 3
 3,148sf N / N

4 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
720 LAKE BRIM DRIVE
 $1,899,000 4 / 4
 3,781sf N / Y
15594 SHOREBIRD LANE
 $1,350,000 4 / 3
 3,022sf Y / N
11714 FLYNN COURT
 $1,349,000 4 / 3
 4,370sf N / Y
15686 PANTHER LAKE DRIVE
 $1,300,000 4 / 3
 3,094sf N / Y
205 SURPRISE DRIVE
 $1,200,000 4 / 2
 2,171sf N / Y
10007 LITTLE ALCOVE LOOP
 $999,990 4 / 3
 2,921sf N / Y
744 LAKE BRIM DRIVE
 $995,000 4 / 3
 2,667sf N / N
8708 SONOMA COAST DRIVE
 $995,000 4 / 3
 2,758sf N / N
9218 HOLLISTON CREEK PLACE
 $980,000 4 / 3
 3,087sf N / Y
15391 LEBEAU LOOP
 $975,000 4 / 3
 3,042sf N / Y
11145 HOLLOW BAY DRIVE
 $899,990 4 / 3
 3,327sf N / N
14645 SCOTT KEY DRIVE
 $890,000 4 / 3
 3,427sf N / Y
931 KYLEE ALLEY
 $875,000 4 / 4
 2,831sf N / N
15372 GILLIGAN COURT
 $870,000 4 / 3
 2,781sf N / Y
14711 WINTER STAY DRIVE
 $849,999 4 / 3
 2,662sf N / Y
11193 HOLLOW BAY DRIVE
 $845,651 4 / 3
 3,327sf N / N
11112 HOLLOW BAY DRIVE
 $799,990 4 / 3
 2,113sf N / N
14931 LEBEAU LOOP
 $799,000 4 / 3
 2,832sf N / Y
9611 LOST CREEK DRIVE
 $795,000 4 / 3
 2,909sf N / N
16555 WINGSPREAD LOOP
 $791,000 4 / 3
 3,093sf N / N
9062 SONOMA COAST DRIVE
 $785,000 4 / 3
 2,909sf N / N
14602 WINTER STAY DRIVE
 $780,000 4 / 3
 3,433sf N / N
15309 HONEYBELL DRIVE
 $775,000 4 / 3
 3,094sf N / N
18344 OLIVER TWIST WAY
 $758,990 4 / 3
 2,924sf N / N
14046 FOX GLOVE STREET
 $755,000 4 / 3
 2,970sf N / Y
15537 MANGO ISLE STREET
 $745,000 4 / 3
 2,909sf N / N
18029 CIDER MILL LANE
 $731,866 4 / 3
 2,113sf N / N
16012 MICELLI DRIVE
 $719,999 4 / 3
 2,428sf N / N
5966 CYPRESS HILL ROAD
 $719,000 4 / 3
 2,839sf N / N
14627 MASTHEAD LANDING CIRCLE
 $699,000 4 / 2
 2,452sf N / Y
9605 LOST CREEK DRIVE
 $699,000 4 / 3
 2,117sf N / Y
8256 BAYVIEW CROSSING DRIVE
 $675,000 4 / 3
 2,557sf N / Y
503 MINNOW CREEK COURT
 $674,990 4 / 3
 2,663sf N / Y
9723 LOST CREEK DRIVE
 $669,000 4 / 3
 2,117sf N / N
16256 MISTY HILLS AVENUE
 $665,000 4 / 3
 2,240sf N / Y
14925 LEBEAU LOOP
 $665,000 4 / 3
 2,116sf N / N
13184 DENDY WAY
 $664,000 4 / 2
 2,211sf N / N
14517 BLACK LAKE PRESERVE STRE
 $660,000 4 / 2
 2,569sf N / N
14902 ARRENA ROAD
 $649,000 4 / 2
 3,392sf Y / N
16827 HOBE SOUND COURT
 $648,075 4 / 3
 2,489sf N / N
6226 MANUSCRIPT STREET
 $642,500 4 / 3
 2,849sf N / N
16136 WIND VIEW LANE
 $624,900 4 / 3
 2,291sf N / N
11864 SHINE VIEW LANE
 $619,990 4 / 3
 2,489sf N / N
4624 PRAIRIE CREEK STREET
 $619,900 4 / 3
 2,459sf N / N
1923 JEAN MARIE DRIVE
 $610,000 4 / 3
 2,916sf N / N
16098 MANGROVE ROAD
 $595,000 4 / 3
 2,472sf N / N
15878 MOONLIGHT BAY STREET
 $595,000 4 / 3
 2,472sf N / N
16137 WIND VIEW LANE
 $589,000 4 / 3
 2,477sf N / N
15929 MOONLIGHT BAY STREET
 $588,000 4 / 3
 2,290sf N / N
113 W DIVISION STREET
 $584,900 4 / 2
 1,487sf N / N
15444 LEBEAU LOOP
 $580,000 4 / 3
 2,415sf N / N
15408 LEBEAU LOOP
 $580,000 4 / 2
 2,415sf N / N
12112 ENCORE AT OVATION WAY
 $570,000 4 / 3
 2,801sf N / N
8220 BAYVIEW CROSSING DRIVE
 $569,999 4 / 3
 2,477sf N / N
15306 LEBEAU LOOP
 $568,000 4 / 2
 2,482sf N / N
2230 ROMANUM DRIVE
 $565,000 4 / 4
 2,562sf N / N
16140 HARBOR MIST ALLEY
 $565,000 4 / 3
 2,477sf N / N
2247 BLACK LAKE BOULEVARD
 $564,990 4 / 2
 2,024sf N / N
503 FIRST CAPE CORAL DRIVE
 $564,000 4 / 2
 2,365sf N / N
8906 DODDINGTON WAY
 $550,000 4 / 3
 2,352sf N / N
2543 BALFORN TOWER WAY
 $550,000 4 / 2
 1,980sf N / N
14571 BAHAMA SWALLOW BOULEVARD
 $534,900 4 / 2
 2,063sf N / N
14954 GUAVA BAY DRIVE
 $525,000 4 / 2
 2,204sf N / N
14030 FRASIER STREET
 $499,900 4 / 2
 2,011sf N / N
680 DUNBAR AVENUE
 $465,000 4 / 2
 1,713sf N / N
9338 TYRELLA PINE TRAIL
 $449,000 4 / 2
 1,696sf N / N

3 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
2827 SANCTUARY LANE
 $2,750,000 3 / 2
 2,178sf N / N
9354 LAKE HICKORY NUT DRIVE
 $1,099,000 3 / 3
 2,278sf Y / N
13037 SANDCASTLE DRIVE
 $994,295 3 / 3
 2,902sf N / Y
15084 CANOPY COVER DRIVE
 $969,000 3 / 2
 2,270sf N / N
13343 SUNNY RETREAT LANE
 $899,900 3 / 2
 2,214sf N / N
9008 SONOMA COAST DRIVE
 $824,950 3 / 2
 2,348sf Y / N
15010 SAWGRASS BLUFF DRIVE
 $699,000 3 / 2
 1,673sf N / Y
15456 GILLIGAN COURT
 $625,000 3 / 3
 2,571sf N / N
15196 NEWTONIA STREET
 $615,000 3 / 3
 2,326sf N / N
16461 OLIVE HILL DRIVE
 $594,990 3 / 2
 2,008sf N / N
16840 HOBE SOUND COURT
 $590,700 3 / 2
 2,027sf N / N
413 COUNTRY COTTAGE LANE
 $589,900 3 / 2
 2,550sf N / N
16809 HOBE SOUND COURT
 $587,795 3 / 2
 2,216sf N / N
13360 SUNNY RETREAT LANE
 $585,000 3 / 2
 2,000sf N / N
16833 HOBE SOUND COURT
 $581,190 3 / 2
 2,216sf N / N
13861 LANYARD WAY
 $579,990 3 / 2
 2,341sf N / N
16845 HOBE SOUND COURT
 $572,555 3 / 2
 2,027sf N / N
16821 HOBE SOUND COURT
 $570,950 3 / 2
 2,027sf N / N
16330 BRISK BREEZE ALLEY
 $567,500 3 / 2
 2,170sf N / N
16857 HOBE SOUBND COURT
 $564,990 3 / 2
 2,216sf N / N
7500 LAKE HANCOCK BOULEVARD
 $560,000 3 / 2
 2,270sf N / N
4122 SHEPPERDS HOLLOW ALLEY
 $559,990 3 / 3
 2,459sf N / N
9972 PALLIDA HICKORY WAY
 $559,900 3 / 2
 2,082sf N / N
11858 SHINE VIEW LANE
 $549,990 3 / 2
 2,027sf N / N
15231 HONEYBELL DRIVE
 $539,900 3 / 2
 2,083sf N / N
6421 NEW INDEPENDENCE PARKWAY
 $539,900 3 / 2
 1,863sf N / N
7935 WINTER WREN STREET
 $535,000 3 / 2
 1,850sf N / N
16242 OUTLOOK SHORE ALLEY
 $515,000 3 / 2
 2,014sf N / N
16149 WIND VIEW LANE
 $505,000 3 / 2
 2,036sf N / N
13837 LANYARD WAY
 $500,000 3 / 2
 1,994sf N / N
8118 SURF BIRD STREET
 $499,000 3 / 2
 1,864sf N / N
15533 MURCOTT BLOSSOM BOULEVAR
 $495,900 3 / 2
 1,765sf N / N
16125 AZURE KEY STREET
 $490,000 3 / 2
 1,685sf N / N
6072 GLORY BOWER DRIVE
 $479,000 3 / 2
 2,128sf N / N
12140 BRACCO STREET
 $474,900 3 / 2
 1,788sf N / N
18185 CIDER MILL LANE
 $470,500 3 / 2
 1,817sf N / N
6108 LEWIS AND CLARK AVENUE
 $460,000 3 / 2
 1,690sf N / N
14446 WHITTRIDGE DRIVE
 $450,000 3 / 2
 1,650sf N / N
12055 BRACCO STREET
 $440,000 3 / 2
 1,668sf N / N
8197 LAKEVIEW CROSSING DRIVE
 $439,900 3 / 2
 1,685sf N / N
15693 SIGNATURE DRIVE
 $438,000 3 / 2
 1,720sf N / N
750 S PARK AVENUE
 $415,000 3 / 1
 1,086sf N / N
14804 COSCESTER STREET
 $409,999 3 / 2
 1,456sf N / N
711 BURCH AVENUE
 $400,000 3 / 2
 1,154sf N / N
15831 GEM VIEW STREET
 $399,590 3 / 2
 1,579sf N / N
823 MAGNOLIA AVENUE
 $339,000 3 / 2
 1,210sf N / N
375 REGAL DOWNS CIRCLE
 $334,900 3 / 2
 1,464sf N / N
515 9TH STREET
 $287,900 3 / 2
 770sf N / N
838 BETHUNE AVENUE
 $277,000 3 / 2
 985sf N / N

2 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
15837 GEM VIEW STREET
 $404,010 2 / 2
 1,579sf N / N
15825 GEM VIEW STREET
 $397,580 2 / 2
 1,579sf N / N

Property Location

Community Info

  • Winter Garden
  • Price Range:
    $277,000-$3,327,429

© 2026 John Hernandez, Realtor ® - All Rights Reserved - Trademarks and Brands are the Property of their Respective Owners