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

3,958 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 - $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
<$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
$200Ks - $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 - $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 - $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 - $600Ks
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 - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $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
$200Ks - $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 - $900Ks
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
$200Ks - $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) 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
$100Ks - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$100Ks - $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
$300Ks - $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 - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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 - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
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 - $800Ks
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
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$400Ks - $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 - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
The Villages® 164 PALERMO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$565,000

4 beds

|

3 baths

|

2,202 sq ft

|

House

164 PALERMO PL, THE VILLAGES, FL, 32159
Community: The Villages®
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
Southshore Bay 17319 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$332,000

2 beds

|

2 baths

|

1,614 sq ft

|

Villa

17319 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Stonecrest 10994 SE 168TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$579,000

3 beds

|

3 baths

|

2,742 sq ft

|

House

10994 SE 168TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
The Villages® 518 SAINT ANDREWS BLVD, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$249,900

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

518 SAINT ANDREWS BLVD, LADY LAKE, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lakeside Landings 4976 SANDPIPER DR, OXFORD, FL, 34484, Oxford, FL 34484
$524,900

4 beds

|

2 baths

|

2,696 sq ft

|

House

4976 SANDPIPER DR, OXFORD, FL, 34484
Community: Lakeside Landings
The Villages® 1486 OLYMPIA ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$319,900

2 beds

|

2 baths

|

1,163 sq ft

|

Villa

1486 OLYMPIA ST, THE VILLAGES, FL, 32163
Community: The Villages®
Latitude Margaritaville 484 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$405,000

2 beds

|

2 baths

|

1,464 sq ft

|

House

484 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 317 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$385,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

317 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
The Villages® 1329 GASTON LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$525,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

1329 GASTON LOOP, THE VILLAGES, FL, 3216...
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.
Latitude Margaritaville 324 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$468,900

2 beds

|

2 baths

|

1,563 sq ft

|

Villa

324 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 540 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$649,000

2 beds

|

2 baths

|

1,922 sq ft

|

House

540 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
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...
Lakeside Landings 10460 SILVER MAPLE AVE, OXFORD, FL, 3448..., Oxford, FL 34484
$340,000

3 beds

|

2 baths

|

1,832 sq ft

|

House

10460 SILVER MAPLE AVE, OXFORD, FL, 3448...
Community: Lakeside Landings
Del Webb Oasis 13732 FRESH IVY ST, WINTER GARDEN, FL, 3..., Winter Garden, FL 34787
$635,000

2 beds

|

2 baths

|

1,889 sq ft

|

House

13732 FRESH IVY ST, WINTER GARDEN, FL, 3...
Community: Del Webb Oasis
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Ashton 4313 HEATH LAND LN, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$359,900

3 beds

|

2 baths

|

1,838 sq ft

|

House

4313 HEATH LAND LN, LAKE WALES, FL, 3385...
Community: Lake Ashton
Oak Run 7157 SW 113TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$235,000

2 beds

|

2 baths

|

1,554 sq ft

|

House

7157 SW 113TH LOOP, OCALA, FL, 34476
Community: Oak Run
Latitude Margaritaville 1068 SEA SHELL CT, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$625,000

2 beds

|

2 baths

|

1,939 sq ft

|

House

1068 SEA SHELL CT, DAYTONA BEACH, FL, 32...
The Villages® 485 PIXIE LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,467 sq ft

|

House

485 PIXIE LN, THE VILLAGES, FL, 32162
Community: The Villages®
Latitude Margaritaville 243 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$519,000

2 beds

|

2 baths

|

1,771 sq ft

|

House

243 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
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.
Latitude Margaritaville 508 HIGH TIDE LN, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$379,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

508 HIGH TIDE LN, DAYTONA BEACH, FL, 321...
Arlington Ridge 26622 BULL RUN, LEESBURG, FL, 34748, Leesburg, FL 34748
$383,000

2 beds

|

2 baths

|

1,755 sq ft

|

House

26622 BULL RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
Stonecrest 17329 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$335,000

3 beds

|

2 baths

|

2,346 sq ft

|

House

17329 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
Latitude Margaritaville 306 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$499,999

2 beds

|

2 baths

|

1,509 sq ft

|

Villa

306 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
On Top of the World 9839 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481
$399,900

2 beds

|

2 baths

|

2,079 sq ft

|

House

9839 SW 90TH ST, 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 8465 SW 101ST AVE, OCALA, FL, 34481, Ocala, FL 34481
$460,000

2 beds

|

2 baths

|

2,145 sq ft

|

House

8465 SW 101ST AVE, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9350 SW 91ST COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$339,000

2 beds

|

2 baths

|

1,970 sq ft

|

House

9350 SW 91ST COURT RD, OCALA, FL, 34481
Community: On Top of the World
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
Stonecrest 11884 SE 179TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$438,900

3 beds

|

3 baths

|

2,306 sq ft

|

House

11884 SE 179TH ST, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Lake Ashton 4033 PHOENICIAN WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$409,900

3 beds

|

2 baths

|

2,095 sq ft

|

House

4033 PHOENICIAN WAY, WINTER HAVEN, FL, 3...
Community: Lake Ashton
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.
Pelican Bay Daytona Beach 905 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$399,900

3 beds

|

3 baths

|

2,484 sq ft

|

House

905 PELICAN BAY DR, DAYTONA BEACH, FL, 3...
Ocala Palms 5110 NW 19TH PL, OCALA, FL, 34482, Ocala, FL 34482
$194,999

2 beds

|

2 baths

|

1,177 sq ft

|

House

5110 NW 19TH PL, OCALA, FL, 34482
Community: Ocala Palms
Spruce Creek Country Club 8608 SE 141ST STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$249,900

2 beds

|

2 baths

|

1,356 sq ft

|

House

8608 SE 141ST STREET RD, SUMMERFIELD, FL...
The Villages® 1736 WATTS MILL WAY, THE VILLAGES, FL, 3..., The Villages, FL 32162
$295,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1736 WATTS MILL WAY, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 514 SAINT ANDREWS BLVD, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$237,900

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

514 SAINT ANDREWS BLVD, LADY LAKE, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 6223 ATKINSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$325,000

2 beds

|

2 baths

|

1,203 sq ft

|

House

6223 ATKINSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 8932 SE 168TH SEDGWICK PL, THE VILLAGES,..., The Villages, FL 32162
$279,900

3 beds

|

2 baths

|

1,483 sq ft

|

Villa

8932 SE 168TH SEDGWICK PL, THE VILLAGES,...
Community: The Villages®
The Villages® 733 PALMA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$400,000

3 beds

|

2 baths

|

1,936 sq ft

|

House

733 PALMA DR, THE VILLAGES, FL, 32159
Community: The Villages®
Lake Jovita Golf and Country Club 34516 HEAVENLY LN, DADE CITY, FL, 33525, Dade City, FL 33525
$750,000

4 beds

|

3 baths

|

2,376 sq ft

|

House

34516 HEAVENLY LN, DADE CITY, FL, 33525
Sun City Center 334 NORTHWAY DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$408,800

2 beds

|

2 baths

|

1,960 sq ft

|

House

334 NORTHWAY DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center

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3,958 homes near Winter Garden
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