Winter Garden , $500,000 - $600,000

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Active 16137 Hampton Crossing Dr, WINTER GARDEN

$600,000

WATERLEIGH PH 1C

16137 Hampton Crossing Dr, WINTER GARDEN

3 Beds 3 Baths 2,040 SqFt Residential Single Family Residence MLS® # G5117862
Active 11036 Robert Frost Dr, WINTER GARDEN

$599,990

▼ $15,000 STOREY GROVE PH 3

11036 Robert Frost Dr, WINTER GARDEN

4 Beds 3 Baths 2,136 SqFt Residential Single Family Residence MLS® # O6410350
Active 8060 Bowery Dr, WINTER GARDEN

$599,900

▼ $10,100 LAKE HANCOCK PRESERVE

8060 Bowery Dr, WINTER GARDEN

5 Beds 3 Baths 3,013 SqFt Residential Single Family Residence MLS® # O6421395
Active 13518 Parkfield Way, WINTER GARDEN

$599,000

▼ $39,000 ENCORE/OVATION PH 2

13518 Parkfield Way, WINTER GARDEN

3 Beds 2 Baths 1,860 SqFt Residential Single Family Residence MLS® # O6430236
Open House
Active 7278 Twilight Bay Dr, WINTER GARDEN

$599,000

LAKEVIEW POINTE/HORIZON WEST PH

7278 Twilight Bay Dr, WINTER GARDEN

4 Beds 2 Baths 2,014 SqFt Residential
Sun, Oct 4th, 2026 @ 1pm - 3pm
Single Family Residence MLS® # O6436600
Active 393 Lake Amberleigh Dr, WINTER GARDEN

$599,000

▼ $1,000 AMBERLEIGH

393 Lake Amberleigh Dr, WINTER GARDEN

3 Beds 3 Baths 2,684 SqFt Residential Single Family Residence MLS® # O6436549
Active 14699 Magnolia Ridge Loop, WINTER GARDEN

$598,000

▼ $10,000 ORCHARD HILLS PH 3

14699 Magnolia Ridge Loop, WINTER GARDEN

3 Beds 3 Baths 2,466 SqFt Residential Single Family Residence MLS® # O6430180
Active 8111 Pacific Loon St, WINTER GARDEN

$595,000

▼ $15,000 SUMMERLAKE PD PH 1B

8111 Pacific Loon St, WINTER GARDEN

5 Beds 3 Baths 2,668 SqFt Residential Single Family Residence MLS® # O6433324
Active 13360 Sunny Retreat Ln, WINTER GARDEN

$595,000

DEL WEBB OASIS

13360 Sunny Retreat Ln, WINTER GARDEN

3 Beds 2 Baths 2,000 SqFt Residential Single Family Residence MLS® # S5156584
Active 12525 Scarlett Sage Ct, WINTER GARDEN

$595,000

CAMBRIDGE CROSSING PH 1A

12525 Scarlett Sage Ct, WINTER GARDEN

4 Beds 3 Baths 2,529 SqFt Residential Single Family Residence MLS® # O6444687
Active 16031 Scarpetta St, WINTER GARDEN

$595,000

▼ $10,500 WATERLEIGH PH 4B & 4C

16031 Scarpetta St, WINTER GARDEN

4 Beds 4 Baths 2,474 SqFt Residential Single Family Residence MLS® # O6373345
Active 14354 Orchard Hills Blvd, WINTER GARDEN

$595,000

ORCHARD HILLS PHASE 2

14354 Orchard Hills Blvd, WINTER GARDEN

4 Beds 3 Baths 2,496 SqFt Residential Single Family Residence MLS® # TB8547558
Active 13235 Spring Grove Way, WINTER GARDEN

$595,000

ENCORE/OVATION PH 2

13235 Spring Grove Way, WINTER GARDEN

3 Beds 2 Baths 1,916 SqFt Residential Single Family Residence MLS® # O6437214
Active 7608 Summerlake Groves St, WINTER GARDEN

$590,000

PANTHER VIEW

7608 Summerlake Groves St, WINTER GARDEN

5 Beds 3 Baths 2,461 SqFt Residential Single Family Residence MLS® # O6438685
Active 14180 Title Way, WINTER GARDEN

$589,990

STOREY GROVE PH 2

14180 Title Way, WINTER GARDEN

4 Beds 4 Baths 2,481 SqFt Residential Single Family Residence MLS® # O6444490
New Open House
Active 517 Garden Heights Dr, WINTER GARDEN

$589,900

GARDEN HEIGHTS

517 Garden Heights Dr, WINTER GARDEN

4 Beds 2 Baths 1,960 SqFt Residential
Sun, Oct 4th, 2026 @ 1pm - 3pm
Single Family Residence MLS® # O6446560
Active 16614 Wingspread Loop, WINTER GARDEN

$589,000

▼ $10,000 HAWKSMOOR-PH 1

16614 Wingspread Loop, WINTER GARDEN

3 Beds 3 Baths 2,372 SqFt Residential Single Family Residence MLS® # O6441370
Active 1631 Charlemagne Ct, WINTER GARDEN

$589,000

TUSCANY

1631 Charlemagne Ct, WINTER GARDEN

3 Beds 2 Baths 2,035 SqFt Residential Single Family Residence MLS® # O6442789
New
Active 1442 Coluso Dr, WINTER GARDEN

$585,000

MAGNOLIA WOOD FIFTH ADD

1442 Coluso Dr, WINTER GARDEN

3 Beds 2 Baths 2,133 SqFt Residential Single Family Residence MLS® # V4951594
Active 14902 Arrena Rd, WINTER GARDEN

$585,000

▼ $14,000 ARROWHEAD LAKES

14902 Arrena Rd, WINTER GARDEN

4 Beds 3 Baths 3,392 SqFt Residential Single Family Residence MLS® # O6248982
Active 325 W Newell St, WINTER GARDEN

$585,000

▲ $10,000 N/A

325 W Newell St, WINTER GARDEN

2 Beds 2 Baths 1,051 SqFt Residential Single Family Residence MLS® # O6441955
Active 8091 Bowery Dr, WINTER GARDEN

$585,000

▼ $35,000 LAKE HANCOCK PRESERVE

8091 Bowery Dr, WINTER GARDEN

4 Beds 3 Baths 2,095 SqFt Residential Single Family Residence MLS® # S5157882
Active 6316 Manuscript St, WINTER GARDEN

$585,000

▼ $14,000 SIGNATURE LAKES PH 02 A B H I J

6316 Manuscript St, WINTER GARDEN

4 Beds 3 Baths 2,608 SqFt Residential Single Family Residence MLS® # O6409661
Active 15043 Pigeon Plum Ln, WINTER GARDEN

$584,900

▼ $9,100 SUMMERLAKE PD PH 2C 2D 2E

15043 Pigeon Plum Ln, WINTER GARDEN

4 Beds 4 Baths 2,695 SqFt Residential Single Family Residence MLS® # S5143009
Active 13014 Sunset Garden Ln, WINTER GARDEN

$584,000

▼ $3,000 WESTHAVEN AT OVATION

13014 Sunset Garden Ln, WINTER GARDEN

4 Beds 3 Baths 2,143 SqFt Residential Single Family Residence MLS® # O6398349
Open House
Active 12706 Grovehurst Ave, WINTER GARDEN

$584,000

▼ $6,000 GROVEHURST A-D

12706 Grovehurst Ave, WINTER GARDEN

5 Beds 3 Baths 3,382 SqFt Residential
Sun, Oct 4th, 2026 @ 9am - 7pm
Single Family Residence MLS® # O6424010
Active 13026 Sunset Garden Ln, WINTER GARDEN

$583,000

▲ $35,840 WESTHAVEN AT OVATION

13026 Sunset Garden Ln, WINTER GARDEN

3 Beds 3 Baths 1,908 SqFt Residential Single Family Residence MLS® # O6400188
Active 12792 Sunset Walk Dr, WINTER GARDEN

$580,000

▲ $74,000 WESTHAVEN AT OVATION

12792 Sunset Walk Dr, WINTER GARDEN

4 Beds 3 Baths 1,930 SqFt Residential Townhouse MLS® # O6414001
New
Active 204 Harbor Dr, WINTER GARDEN

$579,000

THE HARBOR

204 Harbor Dr, WINTER GARDEN

3 Beds 2 Baths 1,522 SqFt Residential Single Family Residence MLS® # O6445377
Active 12776 Sunset Walk Dr, WINTER GARDEN

$579,000

▼ $81,000 WESTHAVEN AT OVATION

12776 Sunset Walk Dr, WINTER GARDEN

4 Beds 4 Baths 2,593 SqFt Residential Townhouse MLS® # O6429992
Active 10625 Atwater Bay Dr, WINTER GARDEN

$575,000

▼ $15,000 WATERLEIGH PH 2D

10625 Atwater Bay Dr, WINTER GARDEN

4 Beds 3 Baths 2,477 SqFt Residential Single Family Residence MLS® # O6439501
Active 8937 Lakeshore Pointe Dr, WINTER GARDEN

$575,000

▼ $10,000 LAKESHORE PRESERVE PH 1

8937 Lakeshore Pointe Dr, WINTER GARDEN

3 Beds 3 Baths 2,052 SqFt Residential Townhouse MLS® # O6420679
Active 13212 Social Ln, WINTER GARDEN

$575,000

▼ $20,000 REGENCY OAKS F

13212 Social Ln, WINTER GARDEN

4 Beds 3 Baths 2,526 SqFt Residential Single Family Residence MLS® # O6398708
New
Active 995 Sadie Ln, WINTER GARDEN

$575,000

ISLAND POINTE SUB

995 Sadie Ln, WINTER GARDEN

4 Beds 2 Baths 2,005 SqFt Residential Single Family Residence MLS® # O6445793
Active 14542 Black Cherry Tr, WINTER GARDEN

$575,000

▼ $14,900 SIGNATURE LKS-PCL 01D PH 01

14542 Black Cherry Tr, WINTER GARDEN

4 Beds 3 Baths 2,234 SqFt Residential Single Family Residence MLS® # O6410574
Active 17070 Water Spring Blvd, WINTER GARDEN

$575,000

WATERLEIGH

17070 Water Spring Blvd, WINTER GARDEN

3 Beds 3 Baths 2,215 SqFt Residential Single Family Residence MLS® # O6424329
Active 12566 Westhaven Oak Dr, WINTER GARDEN

$574,999

▼ $17,001 OSPREY RANCH-PH 1

12566 Westhaven Oak Dr, WINTER GARDEN

4 Beds 3 Baths 2,420 SqFt Residential Single Family Residence MLS® # O6389532
Active 16968 Hamlin Oasis Loop, WINTER GARDEN

$570,000

HAMLIN POINTE

16968 Hamlin Oasis Loop, WINTER GARDEN

4 Beds 3 Baths 2,088 SqFt Residential Single Family Residence MLS® # O6427350
Active 8807 Fountain Palm Aly, WINTER GARDEN

$570,000

▼ $19,999 LAKESHORE PRESERVE PH 1

8807 Fountain Palm Aly, WINTER GARDEN

4 Beds 4 Baths 2,581 SqFt Residential Townhouse MLS® # O6400597
New
Active 4780 Terrace Bluff St, WINTER GARDEN

$569,900

ENCLAVE/HAMLIN

4780 Terrace Bluff St, WINTER GARDEN

4 Beds 4 Baths 2,342 SqFt Residential Single Family Residence MLS® # O6446681
Active 4981 Coral Bean Alley, WINTER GARDEN

$569,900

▼ $5,000 SILVERLEAF RESERVE/HAMLIN PH 2

4981 Coral Bean Alley, WINTER GARDEN

4 Beds 3 Baths 2,114 SqFt Residential Single Family Residence MLS® # O6430193
Active 1630 Chandelle Ln, WINTER GARDEN

$569,900

BELLE MEADE-PH I B D & G

1630 Chandelle Ln, WINTER GARDEN

4 Beds 4 Baths 2,623 SqFt Residential Single Family Residence MLS® # O6442689
Active 16495 Point Rock Dr, WINTER GARDEN

$567,900

▲ $8,000 WATERLEIGH PH 4B & 4C

16495 Point Rock Dr, WINTER GARDEN

4 Beds 3 Baths 2,216 SqFt Residential Single Family Residence MLS® # S5155132
Active 8932 Bismarck Palm Dr, WINTER GARDEN

$565,000

LAKESHORE PRESERVE PH 1

8932 Bismarck Palm Dr, WINTER GARDEN

3 Beds 3 Baths 2,052 SqFt Residential Townhouse MLS® # O6428241
Active 16273 Taliesin St, WINTER GARDEN

$565,000

HAWKSMOOR-PH 1

16273 Taliesin St, WINTER GARDEN

3 Beds 3 Baths 1,836 SqFt Residential Single Family Residence MLS® # S5156149
Active 15929 Moonlight Bay St, WINTER GARDEN

$565,000

▼ $4,000 WATERLEIGH PH 3B 3C & 3D

15929 Moonlight Bay St, WINTER GARDEN

4 Beds 4 Baths 2,290 SqFt Residential Single Family Residence MLS® # S5153663
Active 8873 Fountain Palm Alley, WINTER GARDEN

$565,000

LAKESHORE PRESERVE

8873 Fountain Palm Alley, WINTER GARDEN

3 Beds 3 Baths 2,162 SqFt Residential Townhouse MLS® # O6423477
Active 16461 Olive Hill Dr, WINTER GARDEN

$564,900

▼ $5,000 HAWKSMOOR-PH 1

16461 Olive Hill Dr, WINTER GARDEN

3 Beds 3 Baths 2,008 SqFt Residential Single Family Residence MLS® # O6379181