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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!
Questions? Call us: (689) 407-5757
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
On Top of the World 9856 SW 100TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34481
$289,000

2 beds

|

2 baths

|

1,342 sq ft

|

House

9856 SW 100TH TERRACE RD, OCALA, FL, 344...
Community: On Top of the World
Venetian Bay 2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$350,000

3 beds

|

3 baths

|

1,754 sq ft

|

House

2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Lake Jovita Golf and Country Club 13235 LEGENDS TRL, DADE CITY, FL, 33525, Dade City, FL 33525
$598,000

4 beds

|

3 baths

|

1,945 sq ft

|

House

13235 LEGENDS TRL, DADE CITY, FL, 33525
Traditions at Lake Ruby 3844 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$359,999

4 beds

|

3 baths

|

1,919 sq ft

|

House

3844 BEDFORD AVE, WINTER HAVEN, FL, 3388...
On Top of the World 8851 SW 97TH ST A, OCALA, FL, 34481, Ocala, FL 34481
$197,000

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

8851 SW 97TH ST A, 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
Vienna Square 1620 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$245,000

2 beds

|

2 baths

|

1,329 sq ft

|

Villa

1620 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Oak Run 11631 SW 82ND TER, OCALA, FL, 34481, Ocala, FL 34481
$249,900

2 beds

|

2 baths

|

1,790 sq ft

|

House

11631 SW 82ND TER, OCALA, FL, 34481
Community: Oak Run
The Villages® 3203 ISLAWILD WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163
$394,500

3 beds

|

2 baths

|

1,542 sq ft

|

House

3203 ISLAWILD WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Ocala Palms 2158 NW 50TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$208,000

2 beds

|

2 baths

|

990 sq ft

|

House

2158 NW 50TH AVE, OCALA, FL, 34482
Community: Ocala Palms
Trilogy® Orlando 105 CUPANIA CT, GROVELAND, FL, 34736, Groveland, FL 34736
$348,500

2 beds

|

2 baths

|

1,469 sq ft

|

House

105 CUPANIA CT, GROVELAND, FL, 34736
Community: Trilogy® Orlando
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.
Trilogy® Orlando 112 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736
$318,000

2 beds

|

2 baths

|

1,556 sq ft

|

House

112 FLAME VINE WAY, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Spring Lake Towers 700 MIRROR TER 505, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$139,400

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

700 MIRROR TER 505, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
Latitude Margaritaville 867 BAMA BREEZE DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$499,000

2 beds

|

3 baths

|

1,748 sq ft

|

Villa

867 BAMA BREEZE DR, DAYTONA BEACH, FL, 3...
Sun City Center 635 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$324,000

2 beds

|

2 baths

|

1,493 sq ft

|

Villa

635 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
On Top of the World 8710 SW 91ST PL E, OCALA, FL, 34481, Ocala, FL 34481
$239,999

2 beds

|

2 baths

|

1,795 sq ft

|

Villa

8710 SW 91ST PL E, 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
Ocala Palms 2339 NW 55TH AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$249,900

3 beds

|

2 baths

|

1,514 sq ft

|

House

2339 NW 55TH AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
Del Webb Sunbridge 6501 CYRILS DR, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$450,000

3 beds

|

3 baths

|

1,738 sq ft

|

Townhouse

6501 CYRILS DR, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Pelican Bay Daytona Beach 100 BROWN PELICAN DR, DAYTONA BEACH, FL,..., Daytona Beach, FL 32119
$329,900

3 beds

|

3 baths

|

1,876 sq ft

|

Halfplex

100 BROWN PELICAN DR, DAYTONA BEACH, FL,...
On Top of the World 9661 SW 95TH CT B, OCALA, FL, 34481, Ocala, FL 34481
$215,000

2 beds

|

2 baths

|

1,412 sq ft

|

House

9661 SW 95TH CT B, OCALA, FL, 34481
Community: On Top of the World
Solivita 836 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$253,000

2 beds

|

2 baths

|

1,507 sq ft

|

House

836 GRAND CANAL DR, 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.
Royal Highlands 5533 SQUIRES DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$304,900

3 beds

|

2 baths

|

1,911 sq ft

|

House

5533 SQUIRES DR, LEESBURG, FL, 34748
Community: Royal Highlands
The Wellington 689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,..., Winter Haven, FL 33880
$130,000

2 beds

|

2 baths

|

1,050 sq ft

|

Townhouse

689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,...
Community: The Wellington
Stone Creek 8413 SW 54TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$327,500

2 beds

|

2 baths

|

1,433 sq ft

|

House

8413 SW 54TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Highlands Ridge 2886 S DOCKSIDE DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$79,500

2 beds

|

2 baths

|

1,120 sq ft

|

Mobile Home

2886 S DOCKSIDE DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Stone Creek 6701 SW 94TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$479,000

3 beds

|

3 baths

|

2,611 sq ft

|

House

6701 SW 94TH CIR, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Carlsberg Estates on Lake Suzanne 284 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$239,900

2 beds

|

2 baths

|

1,170 sq ft

|

House

284 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Pelican Bay Daytona Beach 136 GOLDEN EYE DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$229,000

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

136 GOLDEN EYE DR C, DAYTONA BEACH, FL, ...
On Top of the World 9120 SW 91ST TER, OCALA, FL, 34481, Ocala, FL 34481
$439,900

2 beds

|

2 baths

|

2,740 sq ft

|

House

9120 SW 91ST TER, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8546 SW 79TH AVE, OCALA, FL, 34476, Ocala, FL 34476
$287,500

2 beds

|

2 baths

|

1,497 sq ft

|

House

8546 SW 79TH AVE, OCALA, FL, 34476
Community: On Top of the World
On Top of the World 9400 SW 106TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$373,700

2 beds

|

2 baths

|

1,651 sq ft

|

House

9400 SW 106TH AVE, OCALA, FL, 34481
Community: On Top of the World
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 9617 SW 102ND TER, OCALA, FL, 34481, Ocala, FL 34481
$449,900

2 beds

|

2 baths

|

1,983 sq ft

|

House

9617 SW 102ND TER, OCALA, FL, 34481
Community: On Top of the World
Ocala Palms 2459 NW 55TH AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$255,000

3 beds

|

2 baths

|

1,514 sq ft

|

House

2459 NW 55TH AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
Highlands Ridge 2802 S MAINSAIL DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$89,900

2 beds

|

2 baths

|

1,008 sq ft

|

Mobile Home

2802 S MAINSAIL DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Carillon Lakes 3374 WATERLUTE WAY, LAKELAND, FL, 33811, Lakeland, FL 33811
$375,000

3 beds

|

3 baths

|

1,891 sq ft

|

House

3374 WATERLUTE WAY, LAKELAND, FL, 33811
Community: Carillon Lakes
Ocala Preserve 5333 NW 33RD PL, OCALA, FL, 34482, Ocala, FL 34482
$275,000

2 beds

|

2 baths

|

1,368 sq ft

|

Halfplex

5333 NW 33RD PL, OCALA, FL, 34482
Community: Ocala Preserve
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 126 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$385,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

126 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Plantation at Leesburg 4721 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

1,979 sq ft

|

House

4721 TARA VIEW RD, LEESBURG, FL, 34748
Highlands Ridge 2835 S MAINSAIL DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$119,000

2 beds

|

2 baths

|

1,200 sq ft

|

Mobile Home

2835 S MAINSAIL DR, AVON PARK, FL, 33825
Community: Highlands Ridge
SummerGlen 16417 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$330,000

3 beds

|

2 baths

|

2,279 sq ft

|

House

16417 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Ashley Oaks 2033 ASHLEY OAKS CIR, SEBRING, FL, 33870, Sebring, FL 33870
$249,500

3 beds

|

2 baths

|

1,396 sq ft

|

Villa

2033 ASHLEY OAKS CIR, SEBRING, FL, 33870
Community: Ashley Oaks

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3,573 homes near Winter Garden
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