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

3,537 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 - $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 - $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 - $600Ks
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 - $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 - $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 - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Pelican Bay Daytona Beach
$100Ks - $400Ks
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 - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $700Ks
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
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
$200Ks - $600Ks
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
$300Ks - $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 - $400Ks
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
Breakaway Trails
$400Ks - $800Ks
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
$100Ks - $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
Pine Run Estates
$100Ks - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
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
Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Sun City Center 906 HACIENDA DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$258,000

2 beds

|

1 baths

|

1,344 sq ft

|

House

906 HACIENDA DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Harbor Hills Country Club 39911 BAYVIEW DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$449,900

3 beds

|

2 baths

|

2,120 sq ft

|

House

39911 BAYVIEW DR, LADY LAKE, FL, 32159
On Top of the World 8364 SW 79TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$315,000

3 beds

|

2 baths

|

2,032 sq ft

|

House

8364 SW 79TH CIR, OCALA, FL, 34476
Community: On Top of the World
Tampa Bay Golf and Country Club 11116 JENKINS CT, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$299,900

3 beds

|

2 baths

|

1,564 sq ft

|

House

11116 JENKINS CT, SAN ANTONIO, FL, 33576
Lake Ashton 1069 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$375,000

2 beds

|

2 baths

|

1,688 sq ft

|

House

1069 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Harbor Hills Country Club 5435 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$410,000

3 beds

|

2 baths

|

1,821 sq ft

|

House

5435 GROVE MNR, LADY LAKE, FL, 32159
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...
The Villages® 2866 JUDAH ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$314,000

2 beds

|

2 baths

|

1,257 sq ft

|

House

2866 JUDAH ST, THE VILLAGES, FL, 32163
Community: The Villages®
Spruce Creek Country Club 9588 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$339,000

2 beds

|

2 baths

|

1,979 sq ft

|

House

9588 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Traditions at Lake Ruby 3365 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$285,000

2 beds

|

2 baths

|

1,295 sq ft

|

House

3365 RALEIGH DR, WINTER HAVEN, FL, 33884
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 9878 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481
$330,000

2 beds

|

2 baths

|

1,911 sq ft

|

House

9878 SW 97TH LN, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8785 SW 91ST ST B, OCALA, FL, 34481, Ocala, FL 34481
$148,500

2 beds

|

2 baths

|

1,204 sq ft

|

Villa

8785 SW 91ST ST B, OCALA, FL, 34481
Community: On Top of the World
Trilogy® Orlando 537 NARROW VIEW LN, GROVELAND, FL, 34736, Groveland, FL 34736
$424,900

3 beds

|

2 baths

|

1,905 sq ft

|

House

537 NARROW VIEW LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Solivita 543 VIA VITALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$439,000

2 beds

|

3 baths

|

2,235 sq ft

|

House

543 VIA VITALE CT, KISSIMMEE, FL, 34759
Community: Solivita
Sun City Center 627 FORT DUQUESNA DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$360,000

3 beds

|

2 baths

|

1,971 sq ft

|

House

627 FORT DUQUESNA DR, SUN CITY CENTER, F...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1738 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$749,999

4 beds

|

3 baths

|

2,959 sq ft

|

House

1738 AUGUSTINE DR, THE VILLAGES, FL, 321...
Community: The Villages®
Sun City Center 2309 LYNDHURST DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$409,900

3 beds

|

3 baths

|

2,342 sq ft

|

House

2309 LYNDHURST DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Highlands Ridge 3003 OAKHILL DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$314,900

3 beds

|

2 baths

|

1,836 sq ft

|

House

3003 OAKHILL DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Palms at Serenoa 17418 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$415,000

3 beds

|

2 baths

|

1,621 sq ft

|

House

17418 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Latitude Margaritaville 856 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$559,900

2 beds

|

2 baths

|

1,862 sq ft

|

House

856 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.
Sun City Center 382 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$184,990

2 beds

|

2 baths

|

1,516 sq ft

|

Condo

382 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Solivita 525 GENOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$449,000

3 beds

|

3 baths

|

2,325 sq ft

|

House

525 GENOA DR, KISSIMMEE, FL, 34759
Community: Solivita
Oak Run 11653 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476
$269,000

3 beds

|

2 baths

|

1,495 sq ft

|

House

11653 SW 72ND CIR, OCALA, FL, 34476
Community: Oak Run
Pelican Bay Daytona Beach 114 BLUE HERON DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$180,000

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

114 BLUE HERON DR D, DAYTONA BEACH, FL, ...
Summer Trees 129 DUSK MEADOW TRL, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$289,900

2 beds

|

2 baths

|

1,414 sq ft

|

House

129 DUSK MEADOW TRL, PORT ORANGE, FL, 32...
Community: Summer Trees
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 9979 SW 88TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$339,900

2 beds

|

2 baths

|

1,845 sq ft

|

House

9979 SW 88TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Marion Landing 6490 SW 84TH ST, OCALA, FL, 34476, Ocala, FL 34476
$258,000

2 beds

|

2 baths

|

1,758 sq ft

|

House

6490 SW 84TH ST, OCALA, FL, 34476
Community: Marion Landing
Sun City Center 321 SIENA VISTA PL, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$375,000

3 beds

|

2 baths

|

2,021 sq ft

|

House

321 SIENA VISTA PL, SUN CITY CENTER, FL,...
Community: Sun City Center
Stone Creek 6683 SW 97TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$469,900

3 beds

|

2 baths

|

1,958 sq ft

|

House

6683 SW 97TH TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
Ocala Preserve 5235 NW 33RD PL, OCALA, FL, 34482, Ocala, FL 34482
$230,000

2 beds

|

2 baths

|

1,318 sq ft

|

House

5235 NW 33RD PL, OCALA, FL, 34482
Community: Ocala Preserve
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.
Oak Run 10967 SW 81ST AVE, OCALA, FL, 34481, Ocala, FL 34481
$180,000

2 beds

|

2 baths

|

1,224 sq ft

|

House

10967 SW 81ST AVE, OCALA, FL, 34481
Community: Oak Run
Twin Lakes 2632 MEADOWEDGE LP LP, ST. CLOUD, FL, 34..., St. Cloud, FL 34772
$539,999

3 beds

|

3 baths

|

2,335 sq ft

|

House

2632 MEADOWEDGE LP LP, ST. CLOUD, FL, 34...
Community: Twin Lakes
Ocala Preserve 5670 NW 39TH LN, OCALA, FL, 34482, Ocala, FL 34482
$385,000

3 beds

|

2 baths

|

1,854 sq ft

|

House

5670 NW 39TH LN, OCALA, FL, 34482
Community: Ocala Preserve
Solivita 461 TREVISO DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$454,900

3 beds

|

3 baths

|

2,266 sq ft

|

House

461 TREVISO DR, POINCIANA, FL, 34759
Community: Solivita
Majestic Oaks Ocala 5659 SW 89TH PL, OCALA, FL, 34476, Ocala, FL 34476
$399,000

4 beds

|

3 baths

|

2,574 sq ft

|

House

5659 SW 89TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Marco Polo Village 5024 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$529,000

3 beds

|

3 baths

|

2,652 sq ft

|

House

5024 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Marco Polo Village
Solivita 128 RIALTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$319,000

2 beds

|

2 baths

|

1,398 sq ft

|

House

128 RIALTO RD, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 2572 BERRINGTON LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162
$324,900

3 beds

|

2 baths

|

1,483 sq ft

|

House

2572 BERRINGTON LOOP, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 2294 TRAILWINDS TER, THE VILLAGES, FL, 3..., The Villages, FL 32162
$339,900

3 beds

|

2 baths

|

1,398 sq ft

|

Villa

2294 TRAILWINDS TER, THE VILLAGES, FL, 3...
Community: The Villages®
Valencia Lakes 4938 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$309,000

2 beds

|

2 baths

|

1,486 sq ft

|

House

4938 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes

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3,537 homes near Winter Garden
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