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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
<$100k - $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.
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) Trilogy® Orlando
$300Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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 - $900Ks
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
$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
The Lakes at Harmony 7651 FIVE OAKS DR, HARMONY, FL, 34773, Harmony, FL 34773
$510,000

3 beds

|

3 baths

|

2,355 sq ft

|

House

7651 FIVE OAKS DR, HARMONY, FL, 34773
Royal Highlands 21523 QUEEN ANNE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,000

3 beds

|

2 baths

|

1,671 sq ft

|

House

21523 QUEEN ANNE CT, LEESBURG, FL, 34748
Community: Royal Highlands
Highlands Ridge 3929 PUMA DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$370,000

2 beds

|

2 baths

|

1,964 sq ft

|

House

3929 PUMA DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Mirada 31396 CABANA RYE AVE, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$350,000

2 beds

|

3 baths

|

1,747 sq ft

|

Townhouse

31396 CABANA RYE AVE, SAN ANTONIO, FL, 3...
Community: Mirada
Latitude Margaritaville 798 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$659,000

3 beds

|

3 baths

|

2,067 sq ft

|

House

798 JOLLYMON WAY, DAYTONA BEACH, FL, 321...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake James 7770 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$508,000

2 beds

|

2 baths

|

1,990 sq ft

|

House

7770 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Venetian Bay 3049 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$327,000

3 beds

|

3 baths

|

1,614 sq ft

|

House

3049 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Lake James 8160 LAKE JAMES DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$414,900

2 beds

|

2 baths

|

2,002 sq ft

|

House

8160 LAKE JAMES DR, LAKELAND, FL, 33810
Community: Lake James
Oak Run 11298 SW 73RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$335,000

2 beds

|

2 baths

|

1,540 sq ft

|

House

11298 SW 73RD CIR, OCALA, FL, 34476
Community: Oak Run
On Top of the World 9726 SW 94TH TER C, OCALA, FL, 34481, Ocala, FL 34481
$184,900

2 beds

|

2 baths

|

1,412 sq ft

|

Villa

9726 SW 94TH TER C, 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.
Twin Lakes 5075 TWIN LAKES BLVD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$679,900

4 beds

|

4 baths

|

2,870 sq ft

|

House

5075 TWIN LAKES BLVD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Lake Ashton 1124 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$414,900

3 beds

|

2 baths

|

2,113 sq ft

|

House

1124 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Lakeside Landings 10173 JULIA ISLES AVE, OXFORD, FL, 34484, Oxford, FL 34484
$398,900

3 beds

|

2 baths

|

1,970 sq ft

|

House

10173 JULIA ISLES AVE, OXFORD, FL, 34484
Community: Lakeside Landings
On Top of the World 10075 SW 91ST PL, OCALA, FL, 34481, Ocala, FL 34481
$279,900

2 beds

|

2 baths

|

1,766 sq ft

|

House

10075 SW 91ST PL, 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pennbrooke Fairways 651 TIMBERCREST DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$259,900

2 beds

|

2 baths

|

1,468 sq ft

|

House

651 TIMBERCREST DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Del Webb Oasis 12037 BRACCO ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$530,000

3 beds

|

3 baths

|

1,678 sq ft

|

House

12037 BRACCO ST, WINTER GARDEN, FL, 3478...
Community: Del Webb Oasis
Oak Run 10824 SW 90TH TER, OCALA, FL, 34481, Ocala, FL 34481
$184,900

2 beds

|

2 baths

|

960 sq ft

|

House

10824 SW 90TH TER, OCALA, FL, 34481
Community: Oak Run
On Top of the World 8034 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$269,900

3 beds

|

2 baths

|

1,516 sq ft

|

House

8034 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Royal Harbor 5305 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778
$348,500

3 beds

|

2 baths

|

1,824 sq ft

|

House

5305 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
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.
JB Ranch 9238 SW 60TH COURT RD, OCALA, FL, 34476, Ocala, FL 34476
$440,000

3 beds

|

3 baths

|

2,619 sq ft

|

House

9238 SW 60TH COURT RD, OCALA, FL, 34476
Community: JB Ranch
Traditions at Lake Ruby 3136 LANGDON LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$360,000

3 beds

|

2 baths

|

1,999 sq ft

|

House

3136 LANGDON LN, WINTER HAVEN, FL, 33884
On Top of the World 8881 SW 94TH ST E, OCALA, FL, 34481, Ocala, FL 34481
$199,900

2 beds

|

2 baths

|

1,541 sq ft

|

Villa

8881 SW 94TH ST E, OCALA, FL, 34481
Community: On Top of the World
Solivita 657 SHOREHAVEN DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$324,500

2 beds

|

2 baths

|

1,732 sq ft

|

House

657 SHOREHAVEN DR, KISSIMMEE, FL, 34759
Community: Solivita
SummerGlen 16026 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$279,654

3 beds

|

2 baths

|

1,800 sq ft

|

House

16026 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8955 SW 86TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$385,000

3 beds

|

2 baths

|

2,127 sq ft

|

House

8955 SW 86TH LOOP, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9085 SW 96TH LN B, OCALA, FL, 34481, Ocala, FL 34481
$199,500

2 beds

|

2 baths

|

1,709 sq ft

|

Villa

9085 SW 96TH LN B, OCALA, FL, 34481
Community: On Top of the World
The Villages® 1628 BAY MEADOWS LN, THE VILLAGES, FL, 3..., The Villages, FL 32159
$149,995

2 beds

|

2 baths

|

936 sq ft

|

Manufactured Home

1628 BAY MEADOWS LN, THE VILLAGES, FL, 3...
Community: The Villages®
On Top of the World 7935 SW 89TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$294,900

2 beds

|

2 baths

|

1,344 sq ft

|

House

7935 SW 89TH LOOP, OCALA, FL, 34476
Community: On Top of the World
On Top of the World 7987 SW 89TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$349,900

3 beds

|

2 baths

|

1,874 sq ft

|

House

7987 SW 89TH 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.
Stonecrest 12255 SE 177TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$359,900

3 beds

|

2 baths

|

1,768 sq ft

|

House

12255 SE 177TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
On Top of the World 9288 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$308,900

3 beds

|

2 baths

|

1,910 sq ft

|

House

9288 SW 93RD CIR, OCALA, FL, 34481
Community: On Top of the World
Highlands Ridge 4032 CARTER CREEK DR, AVON PARK, FL, 338..., Avon Park, FL 33825
$479,000

3 beds

|

3 baths

|

2,808 sq ft

|

House

4032 CARTER CREEK DR, AVON PARK, FL, 338...
Community: Highlands Ridge
On Top of the World 7834 SW 89TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$319,900

2 beds

|

2 baths

|

1,469 sq ft

|

House

7834 SW 89TH CIR, OCALA, FL, 34481
Community: On Top of the World
Highland Fairways 3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810
$240,000

2 beds

|

2 baths

|

1,529 sq ft

|

House

3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1011 OTTER MILL WAY, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$289,900

2 beds

|

3 baths

|

2,105 sq ft

|

Condo

1011 OTTER MILL WAY, SUN CITY CENTER, FL...
Community: Sun City Center
Four Seasons at Orlando 1987 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$370,000

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1987 KEY BAY TRL, KISSIMMEE, FL, 34747
The Villages® 529 DEL MAR DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$299,900

3 beds

|

2 baths

|

1,539 sq ft

|

House

529 DEL MAR DR, LADY LAKE, FL, 32159
Community: The Villages®
Heritage Hills 3677 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$389,899

3 beds

|

2 baths

|

1,672 sq ft

|

House

3677 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Stone Creek 5576 SW 88TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$304,900

2 beds

|

2 baths

|

1,406 sq ft

|

House

5576 SW 88TH AVE, OCALA, FL, 34481
Community: Stone Creek

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3,573 homes near Winter Garden
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