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Winter Garden HOMES FOR SALE

City:  Celebration | ChampionsGate | Clermont | Davenport | Haines City | Kissimmee | Lake Buena Vista | Orlando | Reunion |  Windermere | Winter Garden

Winter Garden Resorts: The Grove Resort Orlando

Orlando vacation home buyers who appreciate luxury living, an abundance of water activities, and close proximity to area theme parks often find themselves choosing property in Winter Garden. The southwest Orange County town is just minutes from Walt Disney World and features some of the most sought-after real estate in Central Florida.

Check out the available Winter Garden vacation real estate listings below, or continue reading to learn more about the many wonderful holiday communities found in the city!

Winter Garden

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New FEATURED
Active 14145 Creekbed Cir, WINTER GARDEN

$739,000

BRADFORD CREEK

14145 Creekbed Cir, WINTER GARDEN

4 Beds 4 Baths 2,823 SqFt Residential Single Family Residence MLS® # S5156892
FEATURED
Active 14501 Grove Resort Ave 3215, WINTER GARDEN

$199,000

GROVE RESORT

14501 Grove Resort Ave 3215, WINTER GARDEN

2 Beds 2 Baths 1,265 SqFt Residential Condo - Hotel MLS® # S5155653
Active 17802 Old Ymca Rd, WINTER GARDEN

$16,000,000

17802 Old Ymca Rd, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land Land MLS® # O5968921
Active 17999 Old Ymca Rd, WINTER GARDEN

$7,500,000

17999 Old Ymca Rd, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6202825
Active 13377 Lake Butler Blvd, WINTER GARDEN

$5,995,000

NONE

13377 Lake Butler Blvd, WINTER GARDEN

5 Beds 6 Baths 6,000 SqFt Residential Single Family Residence MLS® # O6325350
Active 13542 Sunset Lakes Cir, WINTER GARDEN

$3,799,000

SUNSET LAKES

13542 Sunset Lakes Cir, WINTER GARDEN

5 Beds 6 Baths 5,450 SqFt Residential Single Family Residence MLS® # O6402896
Active 14168 Larkspur Lake Dr, WINTER GARDEN

$2,985,000

SHOREFRONT COVE AT HORIZON WEST

14168 Larkspur Lake Dr, WINTER GARDEN

6 Beds 8 Baths 6,442 SqFt Residential Single Family Residence MLS® # O6430797
Active 4004 Rex Dr, WINTER GARDEN

$2,790,000

▼ $110,000 LAKE AVALON GROVES REP

4004 Rex Dr, WINTER GARDEN

4 Beds 2 Baths 1,804 SqFt Residential Single Family Residence MLS® # O6395737
Active 15522 Shorebird Ln, WINTER GARDEN

$2,700,000

▼ $150,000 LAKESHORE PRESERVE PH 4

15522 Shorebird Ln, WINTER GARDEN

7 Beds 7 Baths 6,400 SqFt Residential Single Family Residence MLS® # O6402632
Active 17902 Seidner Rd, WINTER GARDEN

$2,700,000

▼ $297,000 LAKE AVALON GROVES REP

17902 Seidner Rd, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6316521
Active 7693 Green Mountain Way, WINTER GARDEN

$2,600,000

SUMMERLAKE PD PH 3A

7693 Green Mountain Way, WINTER GARDEN

6 Beds 6 Baths 5,115 SqFt Residential Single Family Residence MLS® # O6432738
Active 7301 Wild Blackberry Tr, WINTER GARDEN

$2,600,000

▼ $260,000 SIGNATURE LKS-PCL 01D PH 02 - INDEPENDENCE

7301 Wild Blackberry Tr, WINTER GARDEN

6 Beds 6 Baths 5,403 SqFt Residential Single Family Residence MLS® # O6430097
Active 17144 Phil C Peters Rd, WINTER GARDEN

$2,550,000

▼ $49,000 LAKE AVALON GROVES REP

17144 Phil C Peters Rd, WINTER GARDEN

4 Beds 5 Baths 4,633 SqFt Residential Single Family Residence MLS® # O6260561
Active 13377 Lake Butler Blvd, WINTER GARDEN

$2,500,000

NONE

13377 Lake Butler Blvd, WINTER GARDEN

4 Beds 5 Baths 4,961 SqFt Residential Single Family Residence MLS® # O6303366
Active 13377 Lake Butler Blvd, WINTER GARDEN

$2,500,000

13377 Lake Butler Blvd, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6304334
Active 15505 Shorebird Ln, WINTER GARDEN

$2,500,000

LAKESHORE PRESERVE PH 4

15505 Shorebird Ln, WINTER GARDEN

6 Beds 7 Baths 5,287 SqFt Residential Single Family Residence MLS® # O6410839
New
Active 880 W Plant St, WINTER GARDEN

$2,500,000

880 W Plant St, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6423134
New
Active 15675 Panther Lake Dr, WINTER GARDEN

$2,399,000

LAKESHORE PRESERVE PH 2

15675 Panther Lake Dr, WINTER GARDEN

5 Beds 5 Baths 4,213 SqFt Residential Single Family Residence MLS® # O6433000
Active 15217 Farm Stand Ct, WINTER GARDEN

$2,325,000

OAKLAND HILLS

15217 Farm Stand Ct, WINTER GARDEN

4 Beds 5 Baths 4,219 SqFt Residential Single Family Residence MLS® # O6422464
Active 16870 Sanctuary Dr, WINTER GARDEN

$2,250,000

SANCTUARY/TWIN WATERS

16870 Sanctuary Dr, WINTER GARDEN

5 Beds 5 Baths 4,132 SqFt Residential Single Family Residence MLS® # O6437883
Open House
Active 15475 Shorebird Ln, WINTER GARDEN

$2,190,000

▼ $59,000 LAKESHORE PRESERVE PH 4

15475 Shorebird Ln, WINTER GARDEN

5 Beds 6 Baths 4,253 SqFt Residential Single Family Residence MLS® # O6433381
Open House
Active 811 Civitas Way, WINTER GARDEN

$2,175,000

▼ $24,000 OAKLAND PARK UN # 2A

811 Civitas Way, WINTER GARDEN

4 Beds 5 Baths 5,138 SqFt Residential Single Family Residence MLS® # O6403760
Active 7701 Summerlake Pointe Blvd, WINTER GARDEN

$2,150,000

▼ $100,000 SUMMERLAKE PD PH 2A & 2B

7701 Summerlake Pointe Blvd, WINTER GARDEN

5 Beds 5 Baths 4,072 SqFt Residential Single Family Residence MLS® # O6391690
Active 16038 Johns Lake Overlook Dr, WINTER GARDEN

$2,099,000

▼ $26,000 HICKORY HAMMOCK PH 1D

16038 Johns Lake Overlook Dr, WINTER GARDEN

5 Beds 5 Baths 4,139 SqFt Residential Single Family Residence MLS® # O6426648
Active 9940 Black Bear Ln, WINTER GARDEN

$2,050,000

▲ $100,000 ACREAGE & UNREC

9940 Black Bear Ln, WINTER GARDEN

4 Beds 5 Baths 3,110 SqFt Residential Single Family Residence MLS® # O6309917
Active 9056 Morgana Ct, WINTER GARDEN

$2,050,000

AVALON COVE

9056 Morgana Ct, WINTER GARDEN

5 Beds 5 Baths 4,832 SqFt Residential Single Family Residence MLS® # O6432897
Active 9110 Morgana Ct, WINTER GARDEN

$1,999,000

▼ $100,000 AVALON COVE

9110 Morgana Ct, WINTER GARDEN

5 Beds 5 Baths 4,661 SqFt Residential Single Family Residence MLS® # O6409413
Active 16077 Barkly Ridge Ct, WINTER GARDEN

$1,999,000

AVALON RIDGE

16077 Barkly Ridge Ct, WINTER GARDEN

6 Beds 7 Baths 5,248 SqFt Residential Single Family Residence MLS® # O6429381
Active 15680 Panther Lake Dr, WINTER GARDEN

$1,950,000

LAKESHORE PRESERVE PH 2

15680 Panther Lake Dr, WINTER GARDEN

5 Beds 6 Baths 4,329 SqFt Residential Single Family Residence MLS® # O6438584
Active 1211 E Maple St, WINTER GARDEN

$1,800,000

OVERSTREET CRATE

1211 E Maple St, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6153590
Active 17224 Old Country Ln, WINTER GARDEN

$1,775,000

LAKE AVALON GROVES REP

17224 Old Country Ln, WINTER GARDEN

6 Beds 4 Baths 3,629 SqFt Residential Single Family Residence MLS® # O6384075
Active 7573 Green Mountain Way, WINTER GARDEN

$1,750,000

WEST LAKE HANCOCK ESTATES

7573 Green Mountain Way, WINTER GARDEN

4 Beds 4 Baths 3,388 SqFt Residential Single Family Residence MLS® # O6429288
Active 906 Allendale Ln, WINTER GARDEN

$1,725,000

▼ $40,000 OAKLAND PARK B-2

906 Allendale Ln, WINTER GARDEN

5 Beds 4 Baths 3,784 SqFt Residential Single Family Residence MLS® # G5107489
Active 8750 Bayview Crossing Dr, WINTER GARDEN

$1,724,500

▼ $75,400 WATERLEIGH PH 1

8750 Bayview Crossing Dr, WINTER GARDEN

5 Beds 6 Baths 4,641 SqFt Residential Single Family Residence MLS® # O6416046
Active 279 Zachary Wade St, WINTER GARDEN

$1,675,000

LAKEVIEW RESERVE

279 Zachary Wade St, WINTER GARDEN

5 Beds 4 Baths 4,473 SqFt Residential Single Family Residence MLS® # O6408014
Active 1101 Eagles Pass Way, WINTER GARDEN

$1,644,999

▼ $5,000 OAKLAND PARK

1101 Eagles Pass Way, WINTER GARDEN

6 Beds 5 Baths 4,104 SqFt Residential Single Family Residence MLS® # O6408835
Open House
Active 17372 Glossy Pomelo Way, WINTER GARDEN

$1,639,900

▼ $9,000 LAKE STAR/OVATION PH 1B

17372 Glossy Pomelo Way, WINTER GARDEN

5 Beds 6 Baths 4,977 SqFt Residential
Sat, Sep 19th, 2026 @ 2pm - 5pm
Single Family Residence MLS® # O6406639
Open House
Active 2450 Dahlgren Way, WINTER GARDEN

$1,625,000

▼ $75,000 BRONSONS LNDGS F & M

2450 Dahlgren Way, WINTER GARDEN

5 Beds 5 Baths 4,365 SqFt Residential Single Family Residence MLS® # TB8481106
Active 325 Crystal Wood Dr, WINTER GARDEN

$1,600,000

WINTER GRV

325 Crystal Wood Dr, WINTER GARDEN

5 Beds 5 Baths 4,442 SqFt Residential Single Family Residence MLS® # O6408089
Active 16788 Muskgrass Dr, WINTER GARDEN

$1,550,000

▼ $50,000 LAKE STAR AT OVATION PHASE 1B

16788 Muskgrass Dr, WINTER GARDEN

4 Beds 5 Baths 4,733 SqFt Residential Single Family Residence MLS® # O6388174
Active 2010 Boss Hewett St, WINTER GARDEN

$1,500,000

HULL ISLAND/OAKLAND PH 2

2010 Boss Hewett St, WINTER GARDEN

5 Beds 4 Baths 3,781 SqFt Residential Single Family Residence MLS® # O6423216
Active 241 N Dillard St, WINTER GARDEN

$1,499,999

J L DILLARD SUB 3

241 N Dillard St, WINTER GARDEN

4 Beds 3 Baths 3,507 SqFt Residential Single Family Residence MLS® # O6353975
Active 412 N Boyd St, WINTER GARDEN

$1,465,000

▼ $30,000 WINTER GARDEN SHORES 2ND ADD

412 N Boyd St, WINTER GARDEN

4 Beds 5 Baths 2,834 SqFt Residential Single Family Residence MLS® # S5154749
New
Active 1720 Lake Roberts Landing Dr, WINTER GARDEN

$1,399,999

LAKE ROBERTS LNDG E

1720 Lake Roberts Landing Dr, WINTER GARDEN

5 Beds 5 Baths 4,919 SqFt Residential Single Family Residence MLS® # O6436608
Active 16614 Harbor Sail Way, WINTER GARDEN

$1,399,000

▼ $51,000 WATERSIDE/JOHNS LAKE PH 1

16614 Harbor Sail Way, WINTER GARDEN

6 Beds 6 Baths 4,882 SqFt Residential Single Family Residence MLS® # O6414639
Active 9103 Morgana Ct, WINTER GARDEN

$1,389,000

▼ $90,000 AVALON COVE

9103 Morgana Ct, WINTER GARDEN

5 Beds 5 Baths 4,376 SqFt Residential Single Family Residence MLS® # O6409652
New
Active 16730 Rusty Anchor Rd, WINTER GARDEN

$1,350,000

WATERSIDE/JOHNS LK-PH 1

16730 Rusty Anchor Rd, WINTER GARDEN

6 Beds 5 Baths 4,451 SqFt Residential Single Family Residence MLS® # S5156404
Active 1698 Juniper Hammock St, WINTER GARDEN

$1,349,000

▼ $50,000 MCALLISTER LNDG

1698 Juniper Hammock St, WINTER GARDEN

7 Beds 4 Baths 4,700 SqFt Residential Single Family Residence MLS® # V4948569

Communities in Winter Garden, Florida


If you’d like more information about purchasing a second home in Windermere, contact a Team Donovan agent at 407-704-2616 or or visit us online.

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