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

3,703 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 - $500Ks
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
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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
<$100k - $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
$300Ks - $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 - $500Ks
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
Valencia Lakes 15908 COBBLE MILL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$324,900

3 beds

|

2 baths

|

1,859 sq ft

|

House

15908 COBBLE MILL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
On Top of the World 9365 SW 94TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$345,000

3 beds

|

2 baths

|

2,063 sq ft

|

House

9365 SW 94TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Heritage Hills 3606 SOLANA CIR, CLERMONT, FL, 34711, Clermont, FL 34711
$424,900

3 beds

|

3 baths

|

2,006 sq ft

|

House

3606 SOLANA CIR, CLERMONT, FL, 34711
Community: Heritage Hills
On Top of the World 7891 SW 89TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$384,000

3 beds

|

2 baths

|

1,874 sq ft

|

House

7891 SW 89TH CIR, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8890 SW 104TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$330,000

3 beds

|

2 baths

|

1,651 sq ft

|

House

8890 SW 104TH CIR, OCALA, FL, 34481
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pennbrooke Fairways 32676 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$270,000

3 beds

|

2 baths

|

1,709 sq ft

|

House

32676 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
The Villages® 16979 SE 81ST CHARLESFORT AVE, THE VILLA..., The Villages, FL 32162
$264,000

2 beds

|

2 baths

|

1,175 sq ft

|

Villa

16979 SE 81ST CHARLESFORT AVE, THE VILLA...
Community: The Villages®
Harbor Hills Country Club 6042 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$364,900

3 beds

|

2 baths

|

2,190 sq ft

|

House

6042 TOPSAIL RD, LADY LAKE, FL, 32159
Sun City Center 1201 BLUEWATER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$285,000

2 beds

|

2 baths

|

1,756 sq ft

|

House

1201 BLUEWATER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Latitude Margaritaville 944 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$456,789

2 beds

|

2 baths

|

1,558 sq ft

|

House

944 MARGARITAVILLE AVE, DAYTONA BEACH, F...
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.
Marion Landing 8732 SW 60TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$239,000

3 beds

|

2 baths

|

1,521 sq ft

|

House

8732 SW 60TH CIR, OCALA, FL, 34476
Community: Marion Landing
Stone Creek 5806 SW 87TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$320,900

3 beds

|

2 baths

|

1,469 sq ft

|

House

5806 SW 87TH AVE, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 10377 SW 106TH CT, OCALA, FL, 34481, Ocala, FL 34481
$345,000

2 beds

|

2 baths

|

1,767 sq ft

|

House

10377 SW 106TH CT, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 10390 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481
$385,000

2 beds

|

2 baths

|

2,019 sq ft

|

House

10390 SW 105TH CT, OCALA, FL, 34481
Community: On Top of the World
Latitude Margaritaville 885 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$459,999

2 beds

|

2 baths

|

1,558 sq ft

|

House

885 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 227 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$499,900

2 beds

|

2 baths

|

1,786 sq ft

|

House

227 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Oak Run 10821 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481
$248,900

2 beds

|

2 baths

|

1,392 sq ft

|

House

10821 SW 87TH TER, OCALA, FL, 34481
Community: Oak Run
Pennbrooke Fairways 33236 GRAND CYPRESS WAY, LEESBURG, FL, 3..., Leesburg, FL 34748
$299,247

3 beds

|

2 baths

|

1,598 sq ft

|

House

33236 GRAND CYPRESS WAY, LEESBURG, FL, 3...
Community: Pennbrooke Fairways
Pennbrooke Fairways 910 EAGLES LNDG, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,247

3 beds

|

2 baths

|

1,807 sq ft

|

House

910 EAGLES LNDG, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Ocala Palms 5915 NW 18TH PL, OCALA, FL, 34482, Ocala, FL 34482
$304,900

2 beds

|

2 baths

|

1,650 sq ft

|

House

5915 NW 18TH PL, OCALA, FL, 34482
Community: Ocala Palms
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® 421 ALDAMA AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$374,247

3 beds

|

2 baths

|

1,392 sq ft

|

House

421 ALDAMA AVE, THE VILLAGES, FL, 32159
Community: The Villages®
Ocala Palms 5500 NW 23RD PL, OCALA, FL, 34482, Ocala, FL 34482
$265,000

3 beds

|

2 baths

|

1,837 sq ft

|

House

5500 NW 23RD PL, OCALA, FL, 34482
Community: Ocala Palms
Sun City Center 301 CALOOSA PALMS CT, SUN CITY CENTER, F..., Sun City Center, FL 33573
$339,999

2 beds

|

2 baths

|

1,528 sq ft

|

House

301 CALOOSA PALMS CT, SUN CITY CENTER, F...
Community: Sun City Center
Del Webb Sunbridge 6375 TRAILBLAZE BND, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$745,000

4 beds

|

4 baths

|

2,781 sq ft

|

House

6375 TRAILBLAZE BND, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
Del Webb Sunbridge 2793 NATURE VIEW RD, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$679,000

4 beds

|

3 baths

|

2,761 sq ft

|

House

2793 NATURE VIEW RD, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Valencia del Sol 4836 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598
$485,000

3 beds

|

2 baths

|

1,890 sq ft

|

House

4836 SEVILLA SHORES DR, WIMAUMA, FL, 335...
Community: Valencia del Sol
Highland Fairways 2234 SEA ISLAND CIR, LAKELAND, FL, 33810, Lakeland, FL 33810
$215,000

2 beds

|

2 baths

|

1,166 sq ft

|

House

2234 SEA ISLAND CIR, LAKELAND, FL, 33810
Community: Highland Fairways
Esplanade at Wiregrass Ranch 4831 ROSATTI RD, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$675,000

3 beds

|

3 baths

|

2,296 sq ft

|

House

4831 ROSATTI RD, WESLEY CHAPEL, FL, 3354...
Pennbrooke Fairways 32622 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$234,247

3 beds

|

2 baths

|

1,611 sq ft

|

House

32622 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Marion Landing 8554 SW 63RD CT, OCALA, FL, 34476, Ocala, FL 34476
$249,900

3 beds

|

2 baths

|

1,829 sq ft

|

House

8554 SW 63RD CT, OCALA, FL, 34476
Community: Marion Landing
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.
Cherrywood 10141 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$179,900

2 beds

|

2 baths

|

1,396 sq ft

|

House

10141 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
Royal Harbor 5502 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778
$356,400

3 beds

|

2 baths

|

1,901 sq ft

|

House

5502 BOUNTY CIR, TAVARES, FL, 32778
Community: Royal Harbor
VillageWalk at Lake Nona 8430 LEATHERLEAF LN, ORLANDO, FL, 32827, Orlando, FL 32827
$415,000

3 beds

|

3 baths

|

1,810 sq ft

|

Townhouse

8430 LEATHERLEAF LN, ORLANDO, FL, 32827
Stone Creek 9685 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$249,500

2 beds

|

2 baths

|

1,305 sq ft

|

House

9685 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
Solivita 2448 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$314,900

3 beds

|

2 baths

|

1,539 sq ft

|

Villa

2448 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 9175 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$279,900

2 beds

|

2 baths

|

1,488 sq ft

|

House

9175 SE 118TH LOOP, SUMMERFIELD, FL, 344...
Cresswind at Victoria Gardens 107 WETHERSFIELD CT, DELAND, FL, 32724, Deland, FL 32724
$330,000

3 beds

|

2 baths

|

1,773 sq ft

|

House

107 WETHERSFIELD CT, DELAND, FL, 32724
The Villages® 21204 SANDALWOOD DR # 21-204, WILDWOOD, ..., Wildwood, FL 34785
$135,000

2 beds

|

2 baths

|

1,110 sq ft

|

Condo

21204 SANDALWOOD DR # 21-204, WILDWOOD, ...
Community: The Villages®
On Top of the World 8580 SW 97TH LANE RD B, OCALA, FL, 34481, Ocala, FL 34481
$199,900

2 beds

|

2 baths

|

1,278 sq ft

|

Villa

8580 SW 97TH LANE RD B, OCALA, FL, 34481
Community: On Top of the World
The Villages® 8333 COUNTY ROAD 109A-1, LADY LAKE, FL, ..., Lady Lake, FL 32159
$339,900

3 beds

|

2 baths

|

1,904 sq ft

|

Manufactured Home

8333 COUNTY ROAD 109A-1, LADY LAKE, FL, ...
Community: The Villages®

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3,703 homes near Winter Garden
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