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

3,573 homes near Winter Garden

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No reviews yet Del Webb Oasis
$400Ks - $1Ms
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $2Ms
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
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3.6 rating (46 reviews) Latitude Margaritaville
$300Ks - $700Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $800Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.1 rating (29 reviews) Oak Run
$100Ks - $500Ks
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 - $400Ks
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
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $500Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$200Ks - $1Ms
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 - $600Ks
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 - $900Ks
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
$100Ks - $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 - $400Ks
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 - $400Ks
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
$300Ks - $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
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $400Ks
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
Venetian Bay 214 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$400,000

3 beds

|

2 baths

|

1,649 sq ft

|

House

214 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Sun City Center 1535 COUNCIL DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$199,999

2 beds

|

2 baths

|

1,343 sq ft

|

House

1535 COUNCIL DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Sun City Center 2122 HEREFORD DR # 511, SUN CITY CENTER,..., Sun City Center, FL 33573
$199,500

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

2122 HEREFORD DR # 511, SUN CITY CENTER,...
Community: Sun City Center
Ocala Palms 5858 NW 27TH PL, OCALA, FL, 34482, Ocala, FL 34482
$350,000

3 beds

|

2 baths

|

2,382 sq ft

|

House

5858 NW 27TH PL, OCALA, FL, 34482
Community: Ocala Palms
On Top of the World 8327 SW 79TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$274,000

3 beds

|

2 baths

|

1,576 sq ft

|

House

8327 SW 79TH CIR, OCALA, FL, 34476
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
The Villages® 2788 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$255,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

2788 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 2509 LOCKSLEY ST # 237, SUN CITY CENTER,..., Sun City Center, FL 33573
$280,000

2 beds

|

2 baths

|

1,878 sq ft

|

Condo

2509 LOCKSLEY ST # 237, SUN CITY CENTER,...
Community: Sun City Center
Solivita 726 IRVINE RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$489,000

3 beds

|

3 baths

|

2,427 sq ft

|

House

726 IRVINE RANCH RD, KISSIMMEE, FL, 3475...
Community: Solivita
Marion Landing 6241 SW 84TH PL, OCALA, FL, 34476, Ocala, FL 34476
$260,000

3 beds

|

2 baths

|

1,808 sq ft

|

House

6241 SW 84TH PL, OCALA, FL, 34476
Community: Marion Landing
Sun City Center 1110 JASMINE CREEK CT, SUN CITY CENTER, ..., Sun City Center, FL 33573
$399,000

2 beds

|

2 baths

|

1,956 sq ft

|

House

1110 JASMINE CREEK CT, SUN CITY CENTER, ...
Community: Sun City Center
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.
Legacy of Leesburg 5300 TREASURE VIEW WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$320,000

3 beds

|

2 baths

|

1,711 sq ft

|

House

5300 TREASURE VIEW WAY, LEESBURG, FL, 34...
Community: Legacy of Leesburg
Plantation at Leesburg 4638 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$350,000

3 beds

|

2 baths

|

2,058 sq ft

|

House

4638 RIVER RIDGE DR, LEESBURG, FL, 34748
Sun City Center 1902 ANDOVER ST 198, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$149,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

1902 ANDOVER ST 198, SUN CITY CENTER, FL...
Community: Sun City Center
Spruce Creek South 9461 SE 173RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$239,900

3 beds

|

2 baths

|

1,677 sq ft

|

House

9461 SE 173RD LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Lake Jovita Golf and Country Club 13247 PALMILLA CIR, DADE CITY, FL, 33525, Dade City, FL 33525
$525,000

4 beds

|

3 baths

|

2,231 sq ft

|

House

13247 PALMILLA CIR, DADE CITY, FL, 33525
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek South 9645 SE 173RD PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$319,000

3 beds

|

2 baths

|

1,450 sq ft

|

House

9645 SE 173RD PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Ocala Palms 2260 NW 51ST TER, OCALA, FL, 34482, Ocala, FL 34482
$380,000

3 beds

|

2 baths

|

1,950 sq ft

|

House

2260 NW 51ST TER, OCALA, FL, 34482
Community: Ocala Palms
Royal Palm 5408 DAYLILLY ST, PORT ORANGE, FL, 32128, Port Orange, FL 32128
$399,900

4 beds

|

2 baths

|

1,871 sq ft

|

House

5408 DAYLILLY ST, PORT ORANGE, FL, 32128
Community: Royal Palm
Sun City Center 2202 CLUBHOUSE DR 174, SUN CITY CENTER, ..., Sun City Center, FL 33573
$130,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

2202 CLUBHOUSE DR 174, SUN CITY CENTER, ...
Community: Sun City Center
The Villages® 903 SANTA ANNA LN, THE VILLAGES, FL, 321..., The Villages, FL 32159
$549,000

2 beds

|

2 baths

|

1,693 sq ft

|

Villa

903 SANTA ANNA LN, THE VILLAGES, FL, 321...
Community: The Villages®
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.
On Top of the World 9686 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$272,000

2 beds

|

2 baths

|

1,515 sq ft

|

House

9686 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8336 SW 77TH CT, OCALA, FL, 34476, Ocala, FL 34476
$345,000

3 beds

|

2 baths

|

1,947 sq ft

|

House

8336 SW 77TH CT, OCALA, FL, 34476
Community: On Top of the World
Sun City Center 443 NOBLE FAIRE DR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$368,900

2 beds

|

2 baths

|

1,970 sq ft

|

House

443 NOBLE FAIRE DR, SUN CITY CENTER, FL,...
Community: Sun City Center
Summit Greens 1124 HIDDEN BLF, CLERMONT, FL, 34711, Clermont, FL 34711
$429,000

2 beds

|

2 baths

|

2,055 sq ft

|

House

1124 HIDDEN BLF, CLERMONT, FL, 34711
Community: Summit Greens
The Villages® 3362 SEBASTION AVE, THE VILLAGES, FL, 32..., The Villages, FL 32163
$385,000

3 beds

|

2 baths

|

1,357 sq ft

|

Villa

3362 SEBASTION AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3425 DIXON LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$353,999

3 beds

|

2 baths

|

2,044 sq ft

|

House

3425 DIXON LN, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 9801 SW 88TH TER B, OCALA, FL, 34481, Ocala, FL 34481
$149,900

2 beds

|

2 baths

|

1,249 sq ft

|

Villa

9801 SW 88TH TER B, OCALA, FL, 34481
Community: On Top of the World
Del Webb Minneola 2797 TOP HILL CT, MINNEOLA, FL, 34715, Minneola, FL 34715
$575,000

3 beds

|

2 baths

|

2,056 sq ft

|

House

2797 TOP HILL CT, MINNEOLA, FL, 34715
Community: Del Webb Minneola
On Top of the World 8801 SW 92ND ST B, OCALA, FL, 34481, Ocala, FL 34481
$179,500

2 beds

|

2 baths

|

1,530 sq ft

|

Villa

8801 SW 92ND ST B, OCALA, FL, 34481
Community: On Top of the World
Venetian Bay 3592 GRANDE TUSCANY WAY, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$1,650,000

4 beds

|

4 baths

|

4,632 sq ft

|

House

3592 GRANDE TUSCANY WAY, NEW SMYRNA BEAC...
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.
Valencia Lakes 16261 AMETHYST KEY DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$265,000

2 beds

|

2 baths

|

1,291 sq ft

|

Villa

16261 AMETHYST KEY DR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
Solivita 1390 HARBOR RIDGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$325,990

2 beds

|

2 baths

|

1,703 sq ft

|

House

1390 HARBOR RIDGE DR, KISSIMMEE, FL, 347...
Community: Solivita
VillageWalk at Lake Nona 12064 NAVALE LN, ORLANDO, FL, 32827, Orlando, FL 32827
$850,000

4 beds

|

4 baths

|

2,514 sq ft

|

House

12064 NAVALE LN, ORLANDO, FL, 32827
On Top of the World 9235 SW 96TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$258,500

2 beds

|

2 baths

|

1,664 sq ft

|

House

9235 SW 96TH COURT RD, OCALA, FL, 34481
Community: On Top of the World
Foxwood Lake Estates 5027 FOREST CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$203,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

5027 FOREST CREST DR, LAKELAND, FL, 3381...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek South 17890 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$219,900

2 beds

|

2 baths

|

1,008 sq ft

|

House

17890 SE 96TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Spruce Creek South 17915 SE 102ND TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$269,900

3 beds

|

2 baths

|

1,726 sq ft

|

House

17915 SE 102ND TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Stone Creek 8491 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$355,750

3 beds

|

2 baths

|

1,697 sq ft

|

House

8491 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
Ocala Palms 5891 NW 26TH ST, OCALA, FL, 34482, Ocala, FL 34482
$329,900

3 beds

|

3 baths

|

1,781 sq ft

|

House

5891 NW 26TH ST, OCALA, FL, 34482
Community: Ocala Palms
Lake Jovita Golf and Country Club 13302 TRAILING MOSS DR, DADE CITY, FL, 3..., Dade City, FL 33525
$875,000

4 beds

|

3 baths

|

2,632 sq ft

|

House

13302 TRAILING MOSS DR, DADE CITY, FL, 3...

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3,573 homes near Winter Garden
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