Homes for Sale in Winter Garden, FL | Real Estate

Active
54 photos
$589,000
3 bd, 2 ba, 2,035 Sq Ft
1631 Charlemagne CourtWinter Garden, FL 34787#O6442789
Single Family Residence1 day
Active
69 photos
$2,495,000
6 bd, 6 ba, 5,036 Sq Ft
907 Celadon StreetWinter Garden, FL 34787#O6420982
Single Family Residence3 days
Active
26 photos
$790,000
5 bd, 4 ba, 3,381 Sq Ft
2242 Wintermere Pointe DriveWinter Garden, FL 34787#G5117774
Single Family Residence4 days
Active
36 photos
$460,000
4 bd, 2 ba, 2,009 Sq Ft
1118 Maidenmoor RoadWinter Garden, FL 34787#O6440167
Single Family Residence2 days
Active
12 photos
$230,000
3 bd, 3 ba, 1,216 Sq Ft
988 Stucki TerraceWinter Garden, FL 34787#TB8539994
Townhouse8 days
Active
34 photos
$925,000
5 bd, 4 ba, 3,202 Sq Ft
285 Crystal Wood DriveWinter Garden, FL 34787#O6440648
Single Family Residence8 days
Active
24 photos
$375,000
3 bd, 3 ba, 1,845 Sq Ft
15279 Harrowgate WayWinter Garden, FL 34787#O6440200
Single Family Residence9 days
Active
64 photos
$839,000
6 bd, 4 ba, 4,181 Sq Ft
1707 Fullers Oak LoopWinter Garden, FL 34787#S5157229
Single Family Residence9 days
Active
30 photos
$415,000
3 bd, 3 ba, 1,369 Sq Ft
1415 Sherbourne StreetWinter Garden, FL 34787#O6439948
Single Family Residence10 days
Active
91 photos
$750,000
6 bd, 4 ba, 4,204 Sq Ft
1523 Juniper Hammock StreetWinter Garden, FL 34787#O6439797
Single Family Residence4 days
Active
49 photos
$899,900
$803,482/acre
1.12 acres, Zoned A-1/CITRUS
144 Tildenville School RoadWinter Garden, FL 34787#O6439913
Land10 days
Active
13 photos
$209,900
2 bd, 2 ba, 918 Sq Ft
109 Windtree Lane NWinter Garden, FL 34787#O6438852
Condominium6 days
Active
44 photos
$749,999
4 bd, 5 ba, 3,543 Sq Ft
809 Burch AvenueWinter Garden, FL 34787#O6440306
Single Family Residence9 days
Active
35 photos
$284,995
3 bd, 2 ba, 1,340 Sq Ft
431 Southern Pecan Circle 101Winter Garden, FL 34787#O6439215
Condominium10 days
Active
47 photos
$619,900
3 bd, 2 ba, 1,572 Sq Ft
2420 Balforn Tower WayWinter Garden, FL 34787#O6438016
Single Family Residence8 days
Active
48 photos
$724,999
4 bd, 4 ba, 2,958 Sq Ft
16924 Tradewind PointWinter Garden, FL 34787#O6439183
Single Family Residence9 days
Active
38 photos
$719,500
4 bd, 3 ba, 3,009 Sq Ft
502 Palm DriveWinter Garden, FL 34787#O6436846
Single Family Residence12 days
Active
18 photos
$540,000
3 bd, 3 ba, 1,915 Sq Ft
760 Walkers Grove LaneWinter Garden, FL 34787#S5156624
Townhouse2 weeks
Active
12 photos
$417,000
3 bd, 3 ba, 1,857 Sq Ft
2017 Portcastle CircleWinter Garden, FL 34787#O6437283
Single Family Residence3 weeks
Active
55 photos
$1,350,000
6 bd, 5 ba, 4,451 Sq Ft
16730 Rusty Anchor RoadWinter Garden, FL 34787#S5156404
Single Family Residence8 days
Active
47 photos
$639,900
3 bd, 2 ba, 2,123 Sq Ft
17307 Bal Harbour DriveWinter Garden, FL 34787#O6436527
Single Family Residence3 weeks
Active
37 photos
$795,000
5 bd, 4 ba, 3,197 Sq Ft
2157 Wintermere Pointe DriveWinter Garden, FL 34787#TB8532509
Single Family Residence4 weeks
Active
1 photos
$435,000
8 bd, 3 ba, 1,750 Sq Ft
208 3rd StreetWinter Garden, FL 34787#O6435284
Single Family Residence4 weeks
Active
2 photos
$435,000
$1,977,273/acre
0.22 acres, Zoned R-2
208 3rd StreetWinter Garden, FL 34787#O6435263
Land4 weeks

Market Overview — WINTER GARDEN, FL

Showing WINTER GARDEN, FL

Property type

ResidentialCommercial

Transaction

For SaleFor Lease

Area Average

Median over the active for-sale listings

$569,951
Median Listing Price: 79
Median Days on EXIT Realty: 2,115
Median Sq Ft: $256
Median Price per Sq Ft

Compare

Compare WINTER GARDEN, FL to another area

Median price, days on market and size comparison by area
Area	Median Listing Price	Median Days on EXIT Realty	Median Sq Ft	Median Price per Sq Ft	Actions
WINTER GARDEN, FL	$569,951	79	2,115	$256

Market Composition

What's on the market

76%Residential653 active
19%For Lease161 active
3%Land27 active
1%Commercial Lease10 active
<1%Commercial4 active
<1%Business3 active
<1%Multi-Family2 active

Active listings by price

Under $200K3% · 18
$200K-$400K21% · 137
$400K-$600K31% · 203
$600K-$800K19% · 124
$800K-$1M15% · 100
Over $1M11% · 73

Median Price Trend

Aug 2026: $1,392,500 -59.5%Sep 2026: $563,500

Thinking of selling?

EXIT Realty’s WINTER GARDEN agents know these numbers street by street — and bring the insight and negotiating experience to turn them into your sale price.

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Nearby Schools

Elementary 8

Dillard Street Elementary School
Winter Garden, FL · 0.5 mi away
Montessori of Winter Garden
Winter Garden, FL · 0.8 mi away
William S Maxey Elementary
Winter Garden, FL · 0.9 mi away
Ucp West Orange Campus
Winter Garden, FL · 1.3 mi away
Tildenville Elementary
Winter Garden, FL · 1.3 mi away
Ucp West Orange Charter
Winter Garden, FL · 1.5 mi away
Sunridge Elementary School
Winter Garden, FL · 2.1 mi away
Sunridge Elementary School
Winter Garden, FL · 2.1 mi away

Secondary 5

Lakeview Middle School
Winter Garden, FL · 0.9 mi away
Westside Tech
Winter Garden, FL · 1.0 mi away
St Lillie V High School
Winter Garden, FL · 1.3 mi away
West Orange High School
Winter Garden, FL · 2.1 mi away
Sunridge Middle School
Winter Garden, FL · 2.1 mi away

Other schools 7

Foundation Academy
Winter Garden, FL · 0.3 mi away
Calvary Baptist Church
Winter Garden, FL · 0.6 mi away
Classes4contractors
Winter Garden, FL · 1.1 mi away
Lakeview Middle School - Ocps
Winter Garden, FL · 1.3 mi away
Hope Charter School
Winter Garden, FL · 1.3 mi away
Starchild Academy Winter Garden
Winter Garden, FL · 1.6 mi away
Athletic Fields
Winter Garden, FL · 2.0 mi away

Winter Garden, FL Real Estate Listings

Winter Garden, FL Real Estate Listings

1631 Charlemagne CourtWinter Garden, FL 34787#O6442789

907 Celadon StreetWinter Garden, FL 34787#O6420982

2242 Wintermere Pointe DriveWinter Garden, FL 34787#G5117774

1118 Maidenmoor RoadWinter Garden, FL 34787#O6440167

988 Stucki TerraceWinter Garden, FL 34787#TB8539994

285 Crystal Wood DriveWinter Garden, FL 34787#O6440648

15279 Harrowgate WayWinter Garden, FL 34787#O6440200

1707 Fullers Oak LoopWinter Garden, FL 34787#S5157229

1415 Sherbourne StreetWinter Garden, FL 34787#O6439948

1523 Juniper Hammock StreetWinter Garden, FL 34787#O6439797

144 Tildenville School RoadWinter Garden, FL 34787#O6439913

109 Windtree Lane NWinter Garden, FL 34787#O6438852

809 Burch AvenueWinter Garden, FL 34787#O6440306

431 Southern Pecan Circle 101Winter Garden, FL 34787#O6439215

2420 Balforn Tower WayWinter Garden, FL 34787#O6438016

16924 Tradewind PointWinter Garden, FL 34787#O6439183

502 Palm DriveWinter Garden, FL 34787#O6436846

760 Walkers Grove LaneWinter Garden, FL 34787#S5156624

2017 Portcastle CircleWinter Garden, FL 34787#O6437283

16730 Rusty Anchor RoadWinter Garden, FL 34787#S5156404

17307 Bal Harbour DriveWinter Garden, FL 34787#O6436527

2157 Wintermere Pointe DriveWinter Garden, FL 34787#TB8532509

208 3rd StreetWinter Garden, FL 34787#O6435284

208 3rd StreetWinter Garden, FL 34787#O6435263

1631 Charlemagne CourtWinter Garden, FL 34787#O6442789

907 Celadon StreetWinter Garden, FL 34787#O6420982

2242 Wintermere Pointe DriveWinter Garden, FL 34787#G5117774

1118 Maidenmoor RoadWinter Garden, FL 34787#O6440167

988 Stucki TerraceWinter Garden, FL 34787#TB8539994

285 Crystal Wood DriveWinter Garden, FL 34787#O6440648

15279 Harrowgate WayWinter Garden, FL 34787#O6440200

1707 Fullers Oak LoopWinter Garden, FL 34787#S5157229

1415 Sherbourne StreetWinter Garden, FL 34787#O6439948

1523 Juniper Hammock StreetWinter Garden, FL 34787#O6439797

144 Tildenville School RoadWinter Garden, FL 34787#O6439913

109 Windtree Lane NWinter Garden, FL 34787#O6438852

809 Burch AvenueWinter Garden, FL 34787#O6440306

431 Southern Pecan Circle 101Winter Garden, FL 34787#O6439215

2420 Balforn Tower WayWinter Garden, FL 34787#O6438016

16924 Tradewind PointWinter Garden, FL 34787#O6439183

502 Palm DriveWinter Garden, FL 34787#O6436846

760 Walkers Grove LaneWinter Garden, FL 34787#S5156624

2017 Portcastle CircleWinter Garden, FL 34787#O6437283

16730 Rusty Anchor RoadWinter Garden, FL 34787#S5156404

17307 Bal Harbour DriveWinter Garden, FL 34787#O6436527

2157 Wintermere Pointe DriveWinter Garden, FL 34787#TB8532509

208 3rd StreetWinter Garden, FL 34787#O6435284

208 3rd StreetWinter Garden, FL 34787#O6435263

1631 Charlemagne CourtWinter Garden, FL 34787#O6442789

907 Celadon StreetWinter Garden, FL 34787#O6420982

2242 Wintermere Pointe DriveWinter Garden, FL 34787#G5117774

1118 Maidenmoor RoadWinter Garden, FL 34787#O6440167

988 Stucki TerraceWinter Garden, FL 34787#TB8539994

285 Crystal Wood DriveWinter Garden, FL 34787#O6440648

15279 Harrowgate WayWinter Garden, FL 34787#O6440200

1707 Fullers Oak LoopWinter Garden, FL 34787#S5157229

1415 Sherbourne StreetWinter Garden, FL 34787#O6439948

1523 Juniper Hammock StreetWinter Garden, FL 34787#O6439797

144 Tildenville School RoadWinter Garden, FL 34787#O6439913

109 Windtree Lane NWinter Garden, FL 34787#O6438852

809 Burch AvenueWinter Garden, FL 34787#O6440306

431 Southern Pecan Circle 101Winter Garden, FL 34787#O6439215

2420 Balforn Tower WayWinter Garden, FL 34787#O6438016

16924 Tradewind PointWinter Garden, FL 34787#O6439183

502 Palm DriveWinter Garden, FL 34787#O6436846

760 Walkers Grove LaneWinter Garden, FL 34787#S5156624

2017 Portcastle CircleWinter Garden, FL 34787#O6437283

16730 Rusty Anchor RoadWinter Garden, FL 34787#S5156404

17307 Bal Harbour DriveWinter Garden, FL 34787#O6436527

2157 Wintermere Pointe DriveWinter Garden, FL 34787#TB8532509

208 3rd StreetWinter Garden, FL 34787#O6435284

208 3rd StreetWinter Garden, FL 34787#O6435263

Market Overview — WINTER GARDEN, FL

Area Average

Compare

Market Composition

What's on the market

Active listings by price