Winter Garden , $400,000 - $500,000

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Active 217 Harbor Dr, WINTER GARDEN

$499,900

▼ $15,100 HARBOR

217 Harbor Dr, WINTER GARDEN

3 Beds 2 Baths 1,737 SqFt Residential Single Family Residence MLS® # O6437038
New
Active 13953 Easdale Alley, WINTER GARDEN

$499,900

WESTHAVEN/OVATION

13953 Easdale Alley, WINTER GARDEN

3 Beds 3 Baths 1,770 SqFt Residential Townhouse MLS® # O6439346
Active 15101 Purple Martin St, WINTER GARDEN

$499,900

▼ $20,000 SUMMERLAKE PD PH 3B

15101 Purple Martin St, WINTER GARDEN

3 Beds 3 Baths 1,998 SqFt Residential Single Family Residence MLS® # O6425221
Active 6355 Argent Wood Dr, WINTER GARDEN

$499,690

SILVERLEAF OAKS

6355 Argent Wood Dr, WINTER GARDEN

3 Beds 3 Baths 1,652 SqFt Residential Townhouse MLS® # O6427512
Active 14280 Braemar St, WINTER GARDEN

$499,000

▼ $40,000 HIGHLAND RDG

14280 Braemar St, WINTER GARDEN

3 Beds 3 Baths 1,964 SqFt Residential Single Family Residence MLS® # TB8500322
Active 12253 S Bracco St, WINTER GARDEN

$499,000

HIGHLAND RDG PH 2

12253 S Bracco St, WINTER GARDEN

3 Beds 3 Baths 1,788 SqFt Residential Single Family Residence MLS® # S5150840
Active 13861 Easdale Alley, WINTER GARDEN

$499,000

▼ $40,000 WESTHAVEN AT OVATION

13861 Easdale Alley, WINTER GARDEN

4 Beds 3 Baths 2,031 SqFt Residential Townhouse MLS® # O6413534
Active 16105 Water Spring Blvd, WINTER GARDEN

$497,000

▼ $2,000 STOREY GROVE PH 2

16105 Water Spring Blvd, WINTER GARDEN

4 Beds 3 Baths 2,042 SqFt Residential Single Family Residence MLS® # O6348822
Open House
Active 516 S Highland Ave, WINTER GARDEN

$495,000

▼ $5,000 REP PT PLEASANT PARK SUB

516 S Highland Ave, WINTER GARDEN

3 Beds 2 Baths 1,716 SqFt Residential
Tue, Sep 15th, 2026 @ 11am - 1pm
Single Family Residence MLS® # O6409675
Active 14543 Golden Harbor Ln, WINTER GARDEN

$495,000

▼ $4,999 WATERMARK

14543 Golden Harbor Ln, WINTER GARDEN

3 Beds 3 Baths 2,039 SqFt Residential Single Family Residence MLS® # O6433451
Active 9231 Grand Island Way, WINTER GARDEN

$495,000

WATERMARK PHASE 2C

9231 Grand Island Way, WINTER GARDEN

4 Beds 3 Baths 2,060 SqFt Residential Single Family Residence MLS® # O6405710
Active 15159 Groveside Rd, WINTER GARDEN

$494,890

PARKVIEW AT HAMLIN

15159 Groveside Rd, WINTER GARDEN

3 Beds 3 Baths 1,881 SqFt Residential Townhouse MLS® # O6428217
Open House
Active 15877 Tollington Alley, WINTER GARDEN

$493,500

ENCORE/OVATION PH 4B

15877 Tollington Alley, WINTER GARDEN

3 Beds 3 Baths 1,835 SqFt Residential Townhouse MLS® # O6427665
Active 15075 Groveside Rd, WINTER GARDEN

$491,080

PARKVIEW AT HAMLIN

15075 Groveside Rd, WINTER GARDEN

3 Beds 3 Baths 1,881 SqFt Residential Townhouse MLS® # O6422529
New
Active 14075 Lochend Way, WINTER GARDEN

$490,000

WESTHAVEN/OVATION

14075 Lochend Way, WINTER GARDEN

4 Beds 3 Baths 2,197 SqFt Residential Townhouse MLS® # O6439835
Active 15165 Groveside Rd, WINTER GARDEN

$489,890

PARKVIEW AT HAMLIN

15165 Groveside Rd, WINTER GARDEN

4 Beds 4 Baths 1,846 SqFt Residential Townhouse MLS® # O6423895
Active 502 First Cape Coral Dr, WINTER GARDEN

$489,000

BLACK LAKE PARK PH 01

502 First Cape Coral Dr, WINTER GARDEN

3 Beds 2 Baths 1,929 SqFt Residential Single Family Residence MLS® # O6436101
Active 9357 Jaywood Rd, WINTER GARDEN

$489,000

WATERLEIGH PH 3B 3C & 3D

9357 Jaywood Rd, WINTER GARDEN

3 Beds 2 Baths 1,685 SqFt Residential Single Family Residence MLS® # S5156518
Active 735 Hurley Dr, WINTER GARDEN

$489,000

ORANGE COVE

735 Hurley Dr, WINTER GARDEN

3 Beds 2 Baths 1,767 SqFt Residential Single Family Residence MLS® # TB8544631
Active 5413 New Independence Pkwy, WINTER GARDEN

$488,000

SIGNATURE LAKES PH 02 A B H I J

5413 New Independence Pkwy, WINTER GARDEN

4 Beds 3 Baths 2,131 SqFt Residential Townhouse MLS® # S5146601
Active 12086 Shine View Ln, WINTER GARDEN

$487,500

WATERLEIGH

12086 Shine View Ln, WINTER GARDEN

3 Beds 3 Baths 1,817 SqFt Residential Townhouse MLS® # O6436174
Active 11117 Bostwick Alley, WINTER GARDEN

$485,000

▼ $22,000 WATERLEIGH PH 4A

11117 Bostwick Alley, WINTER GARDEN

3 Beds 2 Baths 1,685 SqFt Residential Single Family Residence MLS® # O6407552
Active 16802 Oakboro St, WINTER GARDEN

$485,000

▼ $10,000 WATERLEIGH PH 3B 3C & 3D

16802 Oakboro St, WINTER GARDEN

3 Beds 2 Baths 1,705 SqFt Residential Single Family Residence MLS® # O6425489
Active 7272 Windy Willow St, WINTER GARDEN

$483,258

HAMLIN MEADOWS

7272 Windy Willow St, WINTER GARDEN

3 Beds 3 Baths 1,697 SqFt Residential Townhouse MLS® # G5115861
Active 15213 Groveside Rd, WINTER GARDEN

$480,085

PARKVIEW AT HAMLIN

15213 Groveside Rd, WINTER GARDEN

3 Beds 3 Baths 1,846 SqFt Residential Townhouse MLS® # O6433072
Active 14501 Grove Resort Ave 3425, WINTER GARDEN

$480,000

GROVA RESIDENCE & SPA HOTEL CONDO 3

14501 Grove Resort Ave 3425, WINTER GARDEN

2 Beds 2 Baths 1,265 SqFt Residential Condo - Hotel MLS® # O6414956
Active 231 E Lafayette St, WINTER GARDEN

$479,900

M C BRITT SUB 1

231 E Lafayette St, WINTER GARDEN

4 Beds 3 Baths 1,608 SqFt Residential Single Family Residence MLS® # O6425940
Active 14230 Murcott Blossom Blvd, WINTER GARDEN

$479,000

▼ $1,000 LAKEVIEW POINTE/HORIZON WEST P

14230 Murcott Blossom Blvd, WINTER GARDEN

3 Beds 3 Baths 1,950 SqFt Residential Single Family Residence MLS® # O6421836
Open House
Active 8012 Bluejack Oak Dr, WINTER GARDEN

$479,000

▼ $20,000 SUMMERLAKE PD PH 2C 2D 2E

8012 Bluejack Oak Dr, WINTER GARDEN

4 Beds 4 Baths 2,222 SqFt Residential Townhouse MLS® # FC317938
New Open House
Active 1553 Spring Ridge Cir, WINTER GARDEN

$475,000

CROWN POINT SPRINGS

1553 Spring Ridge Cir, WINTER GARDEN

3 Beds 2 Baths 1,729 SqFt Residential Single Family Residence MLS® # S5156629
Active 1009 Spring Loop Way, WINTER GARDEN

$475,000

CROWN POINT SPGS

1009 Spring Loop Way, WINTER GARDEN

3 Beds 2 Baths 1,497 SqFt Residential Single Family Residence MLS® # O6434327
Active 5754 Surprise Lily Dr, WINTER GARDEN

$475,000

▼ $5,000 HAMILTON GARDENS PH 2A 2B

5754 Surprise Lily Dr, WINTER GARDEN

4 Beds 3 Baths 2,128 SqFt Residential Single Family Residence MLS® # S5151845
Active 6982 Twilight Bay Dr, WINTER GARDEN

$475,000

MEZZANO

6982 Twilight Bay Dr, WINTER GARDEN

4 Beds 3 Baths 1,860 SqFt Residential Townhouse MLS® # O6436292
Active 1815 Americus Minor Dr, WINTER GARDEN

$474,990

▼ $10,000 FULLERS CROSSING PH 02 49 31

1815 Americus Minor Dr, WINTER GARDEN

4 Beds 2 Baths 2,199 SqFt Residential Single Family Residence MLS® # O6425157
Active 12830 Sunset Walk Dr, WINTER GARDEN

$471,000

WESTHAVEN AT OVATION

12830 Sunset Walk Dr, WINTER GARDEN

3 Beds 3 Baths 1,857 SqFt Residential Townhouse MLS® # O6415339
Active 113 W Division St, WINTER GARDEN

$469,900

WINTER GARDEN SHORES REP

113 W Division St, WINTER GARDEN

4 Beds 2 Baths 1,487 SqFt Residential Single Family Residence MLS® # S5156876
New
Active 9456 Komika Ln, WINTER GARDEN

$469,500

WATERLEIGH PH 3A

9456 Komika Ln, WINTER GARDEN

3 Beds 2 Baths 1,705 SqFt Residential Single Family Residence MLS® # S5156916
Active 7030 Twilight Bay Dr, WINTER GARDEN

$469,000

MEZZANO

7030 Twilight Bay Dr, WINTER GARDEN

4 Beds 4 Baths 1,920 SqFt Residential Townhouse MLS® # O6410364
Active 14099 Lochend Way, WINTER GARDEN

$468,000

▼ $11,900 WESTHAVEN/OVATION

14099 Lochend Way, WINTER GARDEN

3 Beds 3 Baths 1,720 SqFt Residential Townhouse MLS® # O6404015
Active 10089 Salt Point Dr, WINTER GARDEN

$465,000

▼ $10,000 WATERLEIGH PH 2E

10089 Salt Point Dr, WINTER GARDEN

3 Beds 3 Baths 1,654 SqFt Residential Townhouse MLS® # O6392385
Active 680 Dunbar Ave, WINTER GARDEN

$465,000

OVERSTREET CRATE

680 Dunbar Ave, WINTER GARDEN

4 Beds 2 Baths 1,713 SqFt Residential Single Family Residence MLS® # O6389210
Open House
Active 15806 Gem View St, WINTER GARDEN

$465,000

▼ $30,000 DEL WEBB OASIS PH 3

15806 Gem View St, WINTER GARDEN

2 Beds 2 Baths 1,574 SqFt Residential Villa MLS® # C7526682
Active 16396 Prairie School Dr, WINTER GARDEN

$464,990

▼ $5,000 HAWKSMOOR PH 3

16396 Prairie School Dr, WINTER GARDEN

3 Beds 3 Baths 2,070 SqFt Residential Townhouse MLS® # O6396532
Active 16534 Barbours Creek Way, WINTER GARDEN

$464,990

WATERLEIGH

16534 Barbours Creek Way, WINTER GARDEN

3 Beds 3 Baths 1,817 SqFt Residential Townhouse MLS® # O6433686
Active 14501 Grove Resort Ave 2101, WINTER GARDEN

$460,000

GROVE RESORT AND SPA HOTEL CONDO 1

14501 Grove Resort Ave 2101, WINTER GARDEN

3 Beds 3 Baths 1,544 SqFt Residential Condo - Hotel MLS® # O6353080
Active 411 Millwood Pl, WINTER GARDEN

$459,000

COVINGTON CHASE PH 2A

411 Millwood Pl, WINTER GARDEN

3 Beds 2 Baths 1,696 SqFt Residential Single Family Residence MLS® # TB8518055
Active 12597 Encore At Ovation Way, WINTER GARDEN

$459,000

▼ $6,000 ENCORE AT OVATION

12597 Encore At Ovation Way, WINTER GARDEN

3 Beds 3 Baths 2,322 SqFt Residential Single Family Residence MLS® # O6407413
Active 7276 Windy Willow St, WINTER GARDEN

$456,213

HAMLIN MEADOWS

7276 Windy Willow St, WINTER GARDEN

3 Beds 3 Baths 1,764 SqFt Residential Townhouse MLS® # G5115862