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Winter Garden, FL 55+ active adult communities & homes for sale

3,631 homes near Winter Garden

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5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $1Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
4.1 rating (55 reviews) On Top of the World
$100Ks - $600Ks
On Top of the World, Ocala, FL
New and Resale | 55+ age-restricted | Built 1981 - present | 10,000 homes
3.8 rating (14 reviews) Sun City Center
<$100k - $600Ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$100Ks - $700Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
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3.6 rating (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $700Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.1 rating (29 reviews) Oak Run
$100Ks - $300Ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
4.5 rating (11 reviews) Spruce Creek Country Club
$200Ks - $500Ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes
5 rating (2 reviews) Plantation at Leesburg
$100Ks - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
5 rating (3 reviews) Stonecrest
$200Ks - $500Ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
5 rating (7 reviews) Kings Ridge
$200Ks - $400Ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
5 rating (3 reviews) Twin Lakes
$200Ks - $900Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
$100Ks - $500Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.6 rating (5 reviews) Ocala Preserve
$200Ks - $600Ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $300Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $900Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$200Ks - $2Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
3.8 rating (6 reviews) Trilogy® Orlando
$300Ks - $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
3.8 rating (6 reviews) Tampa Bay Golf and Countr...
$200Ks - $400Ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$200Ks - $300Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
3.6 rating (5 reviews) Heritage Hills
$200Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Ocala Palms
$100Ks - $500Ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300Ks - $600Ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
5 rating (5 reviews) SummerGlen
$200Ks - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (1 reviews) Legacy of Leesburg
$200Ks - $400Ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes
No reviews yet Breakaway Trails
$400Ks - $1Ms
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$400Ks - $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4 rating (2 reviews) Harbor Hills Country Club
$200Ks - $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.8 rating (6 reviews) Highland Lakes
$200Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$300Ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 homes
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Spruce Creek Country Club 13544 SE 89TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$429,000

3 beds

|

2 baths

|

1,958 sq ft

|

House

13544 SE 89TH TERRACE RD, SUMMERFIELD, F...
Sun City Center 823 FOX HILLS DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$287,000

2 beds

|

2 baths

|

1,852 sq ft

|

House

823 FOX HILLS DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Latitude Margaritaville 913 BAMA BREEZE DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$489,500

2 beds

|

2 baths

|

1,558 sq ft

|

House

913 BAMA BREEZE DR, DAYTONA BEACH, FL, 3...
VillageWalk at Lake Nona 11920 KAJETAN LN, ORLANDO, FL, 32827, Orlando, FL 32827
$458,000

2 beds

|

2 baths

|

1,708 sq ft

|

Halfplex

11920 KAJETAN LN, ORLANDO, FL, 32827
Del Webb Orlando 672 CORDOBA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$389,900

2 beds

|

2 baths

|

1,956 sq ft

|

House

672 CORDOBA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
VillageWalk at Lake Nona 12048 TALITHA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$480,000

3 beds

|

3 baths

|

1,830 sq ft

|

Townhouse

12048 TALITHA LN, ORLANDO, FL, 32827
The Villages® 516 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$429,000

3 beds

|

2 baths

|

1,642 sq ft

|

House

516 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Spruce Creek Country Club 12855 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$363,900

2 beds

|

2 baths

|

1,995 sq ft

|

House

12855 SE 92ND COURT RD, SUMMERFIELD, FL,...
Spruce Creek Country Club 12947 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$410,000

3 beds

|

2 baths

|

2,126 sq ft

|

House

12947 SE 97TH TERRACE RD, SUMMERFIELD, F...
Cherrywood 9958 SW 59TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$210,000

3 beds

|

2 baths

|

1,363 sq ft

|

House

9958 SW 59TH CIR, OCALA, FL, 34476
Community: Cherrywood
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Enclave at VillageWalk 10819 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827
$1,525,000

5 beds

|

6 baths

|

5,437 sq ft

|

House

10819 SAVONA WAY, ORLANDO, FL, 32827
Lakeside Landings 5373 COMPASS PT # 1, OXFORD, FL, 34484, Oxford, FL 34484
$213,000

3 beds

|

2 baths

|

1,291 sq ft

|

Condo

5373 COMPASS PT # 1, OXFORD, FL, 34484
Community: Lakeside Landings
The Villages® 8690 SE 173RD WISTERIA ST, THE VILLAGES,..., The Villages, FL 32162
$699,000

3 beds

|

3 baths

|

2,478 sq ft

|

House

8690 SE 173RD WISTERIA ST, THE VILLAGES,...
Community: The Villages®
Lakeside Landings 5375 COMPASS PT # 04, OXFORD, FL, 34484, Oxford, FL 34484
$225,000

2 beds

|

2 baths

|

1,281 sq ft

|

Condo

5375 COMPASS PT # 04, OXFORD, FL, 34484
Community: Lakeside Landings
The Country Club of Mount Dora 9081 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757
$310,000

3 beds

|

2 baths

|

1,582 sq ft

|

House

9081 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 9894 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$429,000

3 beds

|

2 baths

|

2,267 sq ft

|

House

9894 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Summer Trees 120 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$294,501

2 beds

|

2 baths

|

1,245 sq ft

|

House

120 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Spruce Creek Country Club 12592 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$475,000

3 beds

|

2 baths

|

2,413 sq ft

|

House

12592 SE 97TH TERRACE RD, SUMMERFIELD, F...
Highlands Ridge 2765 E WATERVIEW DR, AVON PARK, FL, 3382..., Avon Park, FL 33825
$119,900

2 beds

|

2 baths

|

1,400 sq ft

|

Mobile Home

2765 E WATERVIEW DR, AVON PARK, FL, 3382...
Community: Highlands Ridge
Solivita 724 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$319,500

2 beds

|

3 baths

|

1,938 sq ft

|

House

724 VILLA PARK RD, KISSIMMEE, FL, 34759
Community: Solivita
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Ocala Palms 4677 NW 51ST CT, OCALA, FL, 34482, Ocala, FL 34482
$429,990

4 beds

|

3 baths

|

2,345 sq ft

|

House

4677 NW 51ST CT, OCALA, FL, 34482
Community: Ocala Palms
Solivita 531 BARCELONA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$369,900

3 beds

|

2 baths

|

1,966 sq ft

|

House

531 BARCELONA DR, POINCIANA, FL, 34759
Community: Solivita
The Villages® 2467 ROGERS RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$414,900

3 beds

|

2 baths

|

1,647 sq ft

|

Villa

2467 ROGERS RD, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 845 VASQUEZ AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$489,000

3 beds

|

2 baths

|

1,652 sq ft

|

House

845 VASQUEZ AVE, THE VILLAGES, FL, 32163
Community: The Villages®
Spruce Creek Country Club 9333 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$425,000

2 beds

|

2 baths

|

2,148 sq ft

|

House

9333 SE 124TH PL, SUMMERFIELD, FL, 34491
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 615 ALLEGHENY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$289,000

3 beds

|

2 baths

|

1,550 sq ft

|

House

615 ALLEGHENY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Spruce Creek North 6473 SW 108TH ST, OCALA, FL, 34476, Ocala, FL 34476
$169,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

6473 SW 108TH ST, OCALA, FL, 34476
Community: Spruce Creek North
The Villages® 1819 ZIRCON PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$748,900

4 beds

|

2 baths

|

2,534 sq ft

|

House

1819 ZIRCON PL, THE VILLAGES, FL, 32163
Community: The Villages®
Spruce Creek Country Club 9343 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$469,000

3 beds

|

3 baths

|

2,324 sq ft

|

House

9343 SE 124TH PL, SUMMERFIELD, FL, 34491
Venetian Bay 2820 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$479,500

3 beds

|

3 baths

|

2,203 sq ft

|

Townhouse

2820 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Villages® 1731 MOUNT CARMEL TER, THE VILLAGES, FL,..., The Villages, FL 32162
$383,500

3 beds

|

2 baths

|

1,655 sq ft

|

Villa

1731 MOUNT CARMEL TER, THE VILLAGES, FL,...
Community: The Villages®
Huntington at Hunter's Ridge 23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$425,000

3 beds

|

3 baths

|

1,853 sq ft

|

House

23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Sun City Center 1123 SIGNATURE DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$539,900

3 beds

|

2 baths

|

2,191 sq ft

|

House

1123 SIGNATURE DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Del Webb Orlando 280 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$494,900

3 beds

|

2 baths

|

2,365 sq ft

|

House

280 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Southshore Bay 17554 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$336,900

2 beds

|

3 baths

|

1,737 sq ft

|

Villa

17554 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 500 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$284,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

500 GRAND CANAL DR, POINCIANA, FL, 34759
Community: Solivita
Royal Highlands 5826 PRINCESS CAROLINE PL, LEESBURG, FL,..., Leesburg, FL 34748
$255,000

2 beds

|

2 baths

|

1,448 sq ft

|

House

5826 PRINCESS CAROLINE PL, LEESBURG, FL,...
Community: Royal Highlands
The Villages® 1390 VIOLA CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$299,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1390 VIOLA CT, THE VILLAGES, FL, 32163
Community: The Villages®
Venetian Bay 3611 CASELLO DR, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$295,000

2 beds

|

3 baths

|

1,669 sq ft

|

Townhouse

3611 CASELLO DR, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
The Villages® 4908 NE 123RD LN, OXFORD, FL, 34484, Oxford, FL 34484
$299,900

4 beds

|

4 baths

|

1,912 sq ft

|

House

4908 NE 123RD LN, OXFORD, FL, 34484
Community: The Villages®

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3,631 homes near Winter Garden
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