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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
New Venetian Bay 3454 VELONA AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$469,900

3 beds

|

2 baths

|

2,670 sq ft

|

House

3454 VELONA AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
New Kings Ridge 4003 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711
$384,900

3 beds

|

3 baths

|

1,722 sq ft

|

House

4003 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings Ridge
New Kings Ridge 2028 BRAXTON ST, CLERMONT, FL, 34711, Clermont, FL 34711
$325,000

3 beds

|

2 baths

|

1,170 sq ft

|

House

2028 BRAXTON ST, CLERMONT, FL, 34711
Community: Kings Ridge
New SummerGlen 3970 SW 157TH PLACE RD, OCALA, FL, 34473, Ocala, FL 34473
$349,990

4 beds

|

3 baths

|

1,952 sq ft

|

House

3970 SW 157TH PLACE RD, OCALA, FL, 34473
Community: SummerGlen
New On Top of the World 9662 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481
$237,000

3 beds

|

2 baths

|

1,742 sq ft

|

House

9662 SW 97TH LN, 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
New Sun City Center 2206 HORSHAM PL, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$149,900

2 beds

|

2 baths

|

984 sq ft

|

Condo

2206 HORSHAM PL, SUN CITY CENTER, FL, 33...
Community: Sun City Center
New The Villages® 335 LOGAN ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$319,900

2 beds

|

2 baths

|

1,266 sq ft

|

House

335 LOGAN ST, THE VILLAGES, FL, 32163
Community: The Villages®
New The Villages® 1273 KETTLE LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$445,000

3 beds

|

2 baths

|

1,925 sq ft

|

House

1273 KETTLE LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
New Kings Ridge 2225 ELVERSON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$409,000

3 beds

|

2 baths

|

1,892 sq ft

|

House

2225 ELVERSON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Tarawood 10494 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436
$269,900

3 beds

|

2 baths

|

1,185 sq ft

|

House

10494 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
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 1518 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$419,000

2 beds

|

2 baths

|

2,528 sq ft

|

House

1518 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
Lakes of Mount Dora 8575 HEMPSTEAD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$779,999

3 beds

|

3 baths

|

2,370 sq ft

|

House

8575 HEMPSTEAD WAY, MOUNT DORA, FL, 3275...
Community: Lakes of Mount Dora
The Villages® 2866 JUDAH ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$314,000

2 beds

|

2 baths

|

1,257 sq ft

|

House

2866 JUDAH ST, THE VILLAGES, FL, 32163
Community: The Villages®
Harbor Hills Country Club 6008 APEX WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$824,500

4 beds

|

3 baths

|

3,432 sq ft

|

House

6008 APEX WAY, LADY LAKE, FL, 32159
On Top of the World 8166 SW 80TH TER, OCALA, FL, 34476, Ocala, FL 34476
$265,000

3 beds

|

2 baths

|

1,487 sq ft

|

House

8166 SW 80TH TER, OCALA, FL, 34476
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
Pelican Bay Daytona Beach 156 KINGBIRD CIR 2120, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$229,000

2 beds

|

2 baths

|

1,732 sq ft

|

House

156 KINGBIRD CIR 2120, DAYTONA BEACH, FL...
The Villages® 2721 DAY LILY RUN, THE VILLAGES, FL, 321..., The Villages, FL 32162
$494,900

3 beds

|

2 baths

|

2,355 sq ft

|

House

2721 DAY LILY RUN, THE VILLAGES, FL, 321...
Community: The Villages®
Royal Highlands 21850 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$389,997

3 beds

|

2 baths

|

2,159 sq ft

|

House

21850 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
Sun City Center 739 WINTERBROOKE WAY, SUN CITY CENTER, F..., Sun City Center, FL 33573
$379,900

3 beds

|

2 baths

|

2,180 sq ft

|

House

739 WINTERBROOKE WAY, SUN CITY CENTER, F...
Community: Sun City Center
The Villages® 1881 SASSPARILLA WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$575,000

3 beds

|

2 baths

|

1,965 sq ft

|

House

1881 SASSPARILLA WAY, THE VILLAGES, FL, ...
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.
Del Webb Sunbridge 6494 ROVER WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$580,000

3 beds

|

2 baths

|

1,881 sq ft

|

House

6494 ROVER WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Marco Polo Village 4910 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$349,900

4 beds

|

2 baths

|

1,716 sq ft

|

House

4910 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Marco Polo Village
Stonecrest 17645 SE 117TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$320,000

3 beds

|

3 baths

|

1,686 sq ft

|

House

17645 SE 117TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
Latitude Margaritaville 836 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$524,900

2 beds

|

2 baths

|

1,786 sq ft

|

House

836 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Venetian Bay 3511 SONESTA CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$749,900

4 beds

|

3 baths

|

2,599 sq ft

|

House

3511 SONESTA CT, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 2112 ACADIA GREENS DR # 62, SUN CITY CEN..., Sun City Center, FL 33573
$235,000

2 beds

|

2 baths

|

1,194 sq ft

|

Condo

2112 ACADIA GREENS DR # 62, SUN CITY CEN...
Community: Sun City Center
The Villages® 1007 ALOHA WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$157,500

2 beds

|

2 baths

|

1,152 sq ft

|

Mobile Home

1007 ALOHA WAY, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3024 MACON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$315,000

2 beds

|

2 baths

|

1,270 sq ft

|

Villa

3024 MACON CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 635 D ANGELO LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$485,000

3 beds

|

2 baths

|

1,712 sq ft

|

Villa

635 D ANGELO LN, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1625 ABERCROMBIE WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,240 sq ft

|

House

1625 ABERCROMBIE WAY, THE VILLAGES, FL, ...
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.
The Villages® 1268 CAMERO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$319,900

2 beds

|

2 baths

|

1,248 sq ft

|

House

1268 CAMERO DR, THE VILLAGES, FL, 32159
Community: The Villages®
Del Webb Sunbridge 6514 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771
$539,900

3 beds

|

2 baths

|

1,881 sq ft

|

House

6514 BARNSTORM WAY, SAINT CLOUD, FL, 347...
Community: Del Webb Sunbridge
Royal Highlands 21636 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748
$259,900

3 beds

|

2 baths

|

1,642 sq ft

|

House

21636 KING HENRY AVE, LEESBURG, FL, 3474...
Community: Royal Highlands
Latitude Margaritaville 957 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$465,000

3 beds

|

2 baths

|

1,848 sq ft

|

House

957 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Spruce Creek Country Club 9543 SE 137TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$539,900

3 beds

|

2 baths

|

2,806 sq ft

|

House

9543 SE 137TH STREET RD, SUMMERFIELD, FL...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 9110 SW 96TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$299,900

3 beds

|

2 baths

|

2,329 sq ft

|

House

9110 SW 96TH COURT RD, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8883 SW 93RD LN F, OCALA, FL, 34481, Ocala, FL 34481
$215,000

2 beds

|

2 baths

|

1,369 sq ft

|

Condo

8883 SW 93RD LN F, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 1318 LELAND DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$274,900

2 beds

|

2 baths

|

1,755 sq ft

|

Condo

1318 LELAND DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Oak Run 8386 SW 109TH LN, OCALA, FL, 34481, Ocala, FL 34481
$214,400

2 beds

|

2 baths

|

1,224 sq ft

|

House

8386 SW 109TH LN, OCALA, FL, 34481
Community: Oak Run
Solivita 100 VENTANA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$315,000

2 beds

|

2 baths

|

1,739 sq ft

|

House

100 VENTANA DR, KISSIMMEE, FL, 34759
Community: Solivita

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3,573 homes near Winter Garden
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