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

3,648 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 - $600Ks
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) VillageWalk at Lake Nona
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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
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
Southshore Bay 16840 WHISPER ELM ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$395,000

2 beds

|

2 baths

|

1,951 sq ft

|

House

16840 WHISPER ELM ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Sun City Center 123 GLENDOWER CIR # 123, SUN CITY CENTER..., Sun City Center, FL 33573
$180,000

2 beds

|

2 baths

|

1,008 sq ft

|

Condo

123 GLENDOWER CIR # 123, SUN CITY CENTER...
Community: Sun City Center
Sun City Center 718 DESERT HILLS WAY, SUN CITY CENTER, F..., Sun City Center, FL 33573
$439,900

3 beds

|

2 baths

|

1,775 sq ft

|

House

718 DESERT HILLS WAY, SUN CITY CENTER, F...
Community: Sun City Center
Pennbrooke Fairways 651 TIMBERCREST DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$230,000

2 beds

|

2 baths

|

1,468 sq ft

|

House

651 TIMBERCREST DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Sun City Center 1205 HACIENDA DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$285,000

2 beds

|

2 baths

|

1,533 sq ft

|

House

1205 HACIENDA DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stonecrest 12135 SE 172ND LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$450,000

3 beds

|

2 baths

|

2,031 sq ft

|

House

12135 SE 172ND LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Spruce Creek South 10442 SE 179TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$289,900

3 beds

|

2 baths

|

1,652 sq ft

|

House

10442 SE 179TH PL, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
On Top of the World 9441 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481
$300,000

3 beds

|

2 baths

|

2,164 sq ft

|

House

9441 SW 90TH ST, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9070 SW 106TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$389,983

2 beds

|

2 baths

|

1,983 sq ft

|

House

9070 SW 106TH AVE, OCALA, FL, 34481
Community: On Top of the World
The Villages® 3141 MANSFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$749,000

3 beds

|

2 baths

|

2,340 sq ft

|

House

3141 MANSFIELD ST, 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.
Oak Run 11631 SW 71ST CIR, OCALA, FL, 34476, Ocala, FL 34476
$204,900

2 beds

|

2 baths

|

1,218 sq ft

|

House

11631 SW 71ST CIR, OCALA, FL, 34476
Community: Oak Run
Summit Greens 890 SUMMIT GREENS BLVD, CLERMONT, FL, 34..., Clermont, FL 34711
$358,500

3 beds

|

2 baths

|

1,556 sq ft

|

House

890 SUMMIT GREENS BLVD, CLERMONT, FL, 34...
Community: Summit Greens
On Top of the World 9734 SW 96TH ST, OCALA, FL, 34481, Ocala, FL 34481
$189,000

2 beds

|

2 baths

|

1,352 sq ft

|

House

9734 SW 96TH ST, OCALA, FL, 34481
Community: On Top of the World
Lake Jovita Golf and Country Club 13353 CARNOUSTIE CIR, DADE CITY, FL, 335..., Dade City, FL 33525
$1,395,000

6 beds

|

4 baths

|

4,572 sq ft

|

House

13353 CARNOUSTIE CIR, DADE CITY, FL, 335...
On Top of the World 8552 SW 92ND LN D, OCALA, FL, 34481, Ocala, FL 34481
$175,000

2 beds

|

2 baths

|

1,687 sq ft

|

Villa

8552 SW 92ND LN D, 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
On Top of the World 9222 SW 97TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$365,000

2 beds

|

2 baths

|

1,716 sq ft

|

House

9222 SW 97TH CIR, OCALA, FL, 34481
Community: On Top of the World
Heritage Hills 3210 SONESTA CT B, CLERMONT, FL, 34711, Clermont, FL 34711
$312,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3210 SONESTA CT B, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 862 BOWDEN RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$514,000

3 beds

|

2 baths

|

1,950 sq ft

|

House

862 BOWDEN RD, THE VILLAGES, FL, 32163
Community: The Villages®
On Top of the World 9085 SW 96TH LN B, OCALA, FL, 34481, Ocala, FL 34481
$189,900

2 beds

|

2 baths

|

1,709 sq ft

|

Villa

9085 SW 96TH LN B, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8737 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$419,000

3 beds

|

2 baths

|

2,280 sq ft

|

House

8737 SW 83RD CIR, 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.
Sun City Center 1904 CANTERBURY LN 18, SUN CITY CENTER, ..., Sun City Center, FL 33573
$119,900

2 beds

|

2 baths

|

984 sq ft

|

Condo

1904 CANTERBURY LN 18, SUN CITY CENTER, ...
Community: Sun City Center
On Top of the World 9607 SW 79TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$615,000

3 beds

|

3 baths

|

2,893 sq ft

|

House

9607 SW 79TH LANE RD, OCALA, FL, 34481
Community: On Top of the World
The Country Club of Mount Dora 1861 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$1,099,999

4 beds

|

5 baths

|

4,733 sq ft

|

House

1861 EDGEWATER DR, MOUNT DORA, FL, 32757
On Top of the World 8925 SW 76TH ST, OCALA, FL, 34481, Ocala, FL 34481
$295,000

3 beds

|

2 baths

|

1,469 sq ft

|

House

8925 SW 76TH ST, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9663 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$264,500

2 beds

|

2 baths

|

1,689 sq ft

|

House

9663 SW 92ND PLACE RD, 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 2158 NW 50TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$199,999

2 beds

|

2 baths

|

990 sq ft

|

House

2158 NW 50TH AVE, OCALA, FL, 34482
Community: Ocala Palms
The Villages® 1787 FOLIAGE LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$309,900

2 beds

|

2 baths

|

1,132 sq ft

|

Villa

1787 FOLIAGE LN, THE VILLAGES, FL, 32162
Community: The Villages®
Stonecrest 17471 SE 110TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$374,000

2 beds

|

2 baths

|

2,020 sq ft

|

House

17471 SE 110TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
On Top of the World 9121 SW 83RD CT C, OCALA, FL, 34481, Ocala, FL 34481
$149,900

2 beds

|

2 baths

|

1,249 sq ft

|

Villa

9121 SW 83RD CT C, OCALA, FL, 34481
Community: On Top of the World
VillageWalk at Lake Nona 11846 NAUTICA DR, ORLANDO, FL, 32827, Orlando, FL 32827
$425,000

3 beds

|

3 baths

|

1,680 sq ft

|

Townhouse

11846 NAUTICA DR, ORLANDO, FL, 32827
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 10557 SW 98TH LN, OCALA, FL, 34481, Ocala, FL 34481
$423,000

3 beds

|

3 baths

|

2,536 sq ft

|

House

10557 SW 98TH LN, OCALA, FL, 34481
Community: On Top of the World
Ocala Palms 5137 NW 20TH PL, OCALA, FL, 34482, Ocala, FL 34482
$299,999

2 beds

|

2 baths

|

1,569 sq ft

|

House

5137 NW 20TH PL, OCALA, FL, 34482
Community: Ocala Palms
Alhambra Villas Condominiums 201 N HILL AVE 150, DELAND, FL, 32724, Deland, FL 32724
$199,900

2 beds

|

2 baths

|

1,090 sq ft

|

Condo

201 N HILL AVE 150, DELAND, FL, 32724
On Top of the World 8678 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$323,000

3 beds

|

2 baths

|

1,695 sq ft

|

House

8678 SW 83RD CIR, OCALA, FL, 34481
Community: On Top of the World
Alhambra Villas Condominiums 217 N HILL AVE 20, DELAND, FL, 32724, Deland, FL 32724
$234,900

2 beds

|

2 baths

|

1,066 sq ft

|

Condo

217 N HILL AVE 20, DELAND, FL, 32724
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Twin Lakes 5081 TWIN LAKES BLVD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$474,500

3 beds

|

3 baths

|

2,208 sq ft

|

House

5081 TWIN LAKES BLVD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Harbor Hills Country Club 6048 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$324,900

3 beds

|

2 baths

|

2,028 sq ft

|

House

6048 TOPSAIL RD, LADY LAKE, FL, 32159
Stone Creek 9425 SW 76TH ST, OCALA, FL, 34481, Ocala, FL 34481
$243,888

2 beds

|

2 baths

|

1,289 sq ft

|

House

9425 SW 76TH ST, OCALA, FL, 34481
Community: Stone Creek
Royal Harbor 5305 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778
$339,900

3 beds

|

2 baths

|

1,824 sq ft

|

House

5305 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
Valencia Lakes 16113 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$494,900

4 beds

|

3 baths

|

2,467 sq ft

|

House

16113 CAPE CORAL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes

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3,648 homes near Winter Garden
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