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

3,952 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
$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
$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) 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 - $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
$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
$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
$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 - $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
On Top of the World 6565 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$242,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6565 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
On Top of the World 6571 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$242,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6571 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
On Top of the World 6573 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$252,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6573 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
On Top of the World 6559 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$252,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6559 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
On Top of the World 8650 SW 83RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$388,000

3 beds

|

2 baths

|

2,635 sq ft

|

House

8650 SW 83RD LOOP, 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
Cresswind at Victoria Gardens 212 STONINGTON WAY, DELAND, FL, 32724, Deland, FL 32724
$310,000

2 beds

|

2 baths

|

1,494 sq ft

|

House

212 STONINGTON WAY, DELAND, FL, 32724
Cherrywood 10141 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$194,900

2 beds

|

2 baths

|

1,396 sq ft

|

House

10141 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
Southshore Bay 16868 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$349,900

2 beds

|

2 baths

|

1,683 sq ft

|

House

16868 SCUBA CREST ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Sun City Center 206 ANDOVER PL N UNIT 96, SUN CITY CENTE..., Sun City Center, FL 33573
$107,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

206 ANDOVER PL N UNIT 96, SUN CITY CENTE...
Community: Sun City Center
Legacy of Leesburg 5135 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$369,000

3 beds

|

2 baths

|

2,055 sq ft

|

House

5135 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
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.
Spruce Creek Country Club 9171 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$299,913

2 beds

|

2 baths

|

1,575 sq ft

|

House

9171 SE 118TH LOOP, SUMMERFIELD, FL, 344...
On Top of the World 9662 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481
$243,900

3 beds

|

2 baths

|

1,742 sq ft

|

House

9662 SW 97TH LN, OCALA, FL, 34481
Community: On Top of the World
Oak Run 7248 SW 115TH PL, OCALA, FL, 34476, Ocala, FL 34476
$212,500

2 beds

|

2 baths

|

1,379 sq ft

|

House

7248 SW 115TH PL, OCALA, FL, 34476
Community: Oak Run
Royal Highlands 20740 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$370,000

3 beds

|

2 baths

|

2,136 sq ft

|

House

20740 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Spruce Creek South 10476 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$244,000

2 beds

|

2 baths

|

1,473 sq ft

|

House

10476 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 904 DESERT HILLS DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$255,900

3 beds

|

2 baths

|

1,662 sq ft

|

House

904 DESERT HILLS DR, SUN CITY CENTER, FL...
Community: Sun City Center
Stonecrest 11041 SE 169TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$320,000

3 beds

|

2 baths

|

1,417 sq ft

|

House

11041 SE 169TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 971 MARGAUX TRL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$293,000

2 beds

|

2 baths

|

1,156 sq ft

|

House

971 MARGAUX TRL, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1324 BALBOA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$264,900

2 beds

|

2 baths

|

1,094 sq ft

|

House

1324 BALBOA CT, THE VILLAGES, FL, 32159
Community: The Villages®
Ocala Palms 2398 NW 50TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$329,500

3 beds

|

2 baths

|

2,246 sq ft

|

House

2398 NW 50TH AVE, OCALA, FL, 34482
Community: Ocala Palms
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.
The Villages® 1233 CARVELLO DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$334,247

2 beds

|

2 baths

|

1,148 sq ft

|

House

1233 CARVELLO DR, THE VILLAGES, FL, 3216...
Community: The Villages®
Sun City Center 2082 SIFIELD GREENS WAY # 3, SUN CITY CE..., Sun City Center, FL 33573
$285,000

2 beds

|

2 baths

|

1,206 sq ft

|

Condo

2082 SIFIELD GREENS WAY # 3, SUN CITY CE...
Community: Sun City Center
Quail Meadow 4572 NW 32ND ST, OCALA, FL, 34482, Ocala, FL 34482
$370,000

3 beds

|

2 baths

|

2,108 sq ft

|

House

4572 NW 32ND ST, OCALA, FL, 34482
Community: Quail Meadow
Pennbrooke Fairways 305 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$264,247

2 beds

|

2 baths

|

1,631 sq ft

|

House

305 RANCHWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
The Villages® 17353 SE 76TH FLINTLOCK TER, THE VILLAGE..., The Villages, FL 32162
$319,000

2 beds

|

2 baths

|

1,388 sq ft

|

House

17353 SE 76TH FLINTLOCK TER, THE VILLAGE...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 913 BAMA BREEZE DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$508,000

2 beds

|

2 baths

|

1,558 sq ft

|

House

913 BAMA BREEZE DR, DAYTONA BEACH, FL, 3...
Pennbrooke Fairways 32622 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$255,247

3 beds

|

2 baths

|

1,611 sq ft

|

House

32622 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Palm Cay 7632 SW 112TH LN, OCALA, FL, 34476, Ocala, FL 34476
$199,900

2 beds

|

2 baths

|

1,032 sq ft

|

House

7632 SW 112TH LN, OCALA, FL, 34476
Community: Palm Cay
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
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
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.
The Villages® 1405 W SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$299,900

2 beds

|

2 baths

|

1,192 sq ft

|

House

1405 W SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
Windermere 828 WINDERMERE BLVD, INVERNESS, FL, 3445..., Inverness, FL 34453
$219,000

2 beds

|

2 baths

|

1,202 sq ft

|

Villa

828 WINDERMERE BLVD, INVERNESS, FL, 3445...
Community: Windermere
The Lakes at Harmony 3420 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$290,000

2 beds

|

2 baths

|

1,534 sq ft

|

House

3420 SAGEBRUSH ST, HARMONY, FL, 34773
On Top of the World 9741 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481
$219,000

2 beds

|

2 baths

|

1,201 sq ft

|

House

9741 SW 97TH LN, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8655 SW 86TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$307,500

3 beds

|

2 baths

|

1,867 sq ft

|

House

8655 SW 86TH 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
Harbor Hills Country Club 39206 TREELINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$699,317

4 beds

|

4 baths

|

3,145 sq ft

|

House

39206 TREELINE DR, LADY LAKE, FL, 32159
Sandpiper Golf & Country Club 537 EAGLE RUN, LAKELAND, FL, 33809, Lakeland, FL 33809
$260,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

537 EAGLE RUN, LAKELAND, FL, 33809
Valencia Lakes 4922 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$425,000

2 beds

|

2 baths

|

2,070 sq ft

|

House

4922 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Solivita 532 CASANOVA CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$265,000

2 beds

|

2 baths

|

1,507 sq ft

|

House

532 CASANOVA CT, KISSIMMEE, FL, 34759
Community: Solivita
Venetian Bay 3608 ROMEA CIR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$355,000

3 beds

|

3 baths

|

2,036 sq ft

|

Townhouse

3608 ROMEA CIR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay

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3,952 homes near Winter Garden
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