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

3,631 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 - $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 (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
$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
$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
$200Ks - $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 - $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
<$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
Venetian Bay 677 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$719,689

4 beds

|

4 baths

|

3,221 sq ft

|

House

677 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Del Webb Sunbridge 6488 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771
$404,990

3 beds

|

3 baths

|

1,767 sq ft

|

Townhouse

6488 BARNSTORM WAY, SAINT CLOUD, FL, 347...
Community: Del Webb Sunbridge
Del Webb Sunbridge 6476 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771
$404,990

3 beds

|

3 baths

|

1,767 sq ft

|

Townhouse

6476 BARNSTORM WAY, SAINT CLOUD, FL, 347...
Community: Del Webb Sunbridge
Del Webb Sunbridge 6553 ROVER WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$529,990

3 beds

|

3 baths

|

2,018 sq ft

|

House

6553 ROVER WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Del Webb Sunbridge 6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771
$515,990

3 beds

|

3 baths

|

2,077 sq ft

|

House

6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Preserve 11536 SW 140TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432
$262,500

2 beds

|

2 baths

|

1,830 sq ft

|

House

11536 SW 140TH LOOP, DUNNELLON, FL, 3443...
Stone Creek 8464 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$389,000

3 beds

|

2 baths

|

1,663 sq ft

|

House

8464 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
Latitude Margaritaville 422 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$575,000

3 beds

|

2 baths

|

1,922 sq ft

|

House

422 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Spruce Creek Preserve 11353 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$239,900

2 beds

|

2 baths

|

1,664 sq ft

|

House

11353 SW 138TH LN, DUNNELLON, FL, 34432
Sun City Center 2039 BERRY ROBERTS DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$420,000

3 beds

|

2 baths

|

2,352 sq ft

|

House

2039 BERRY ROBERTS DR, SUN CITY CENTER, ...
Community: Sun City Center
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 11473 SW 82ND COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$249,900

2 beds

|

2 baths

|

1,602 sq ft

|

House

11473 SW 82ND COURT RD, OCALA, FL, 34481
Community: Oak Run
Spruce Creek Country Club 12860 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$469,965

2 beds

|

2 baths

|

1,639 sq ft

|

House

12860 SE 92ND COURT RD, SUMMERFIELD, FL,...
The Villages® 1511 LAVACA LN, THE VILLAGES, FL, 32159, The Villages, FL 32159
$608,000

3 beds

|

2 baths

|

2,058 sq ft

|

House

1511 LAVACA LN, THE VILLAGES, FL, 32159
Community: The Villages®
Spruce Creek Country Club 13535 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$419,900

3 beds

|

3 baths

|

2,262 sq ft

|

House

13535 SE 97TH TERRACE RD, SUMMERFIELD, F...
Spruce Creek Preserve 11879 SW 137TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432
$209,900

2 beds

|

1 baths

|

943 sq ft

|

House

11879 SW 137TH LOOP, DUNNELLON, FL, 3443...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Preserve 11470 SW 139TH ST, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$234,950

2 beds

|

2 baths

|

1,672 sq ft

|

House

11470 SW 139TH ST, DUNNELLON, FL, 34432
Spruce Creek Preserve 14695 SW 112TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$244,000

2 beds

|

2 baths

|

1,444 sq ft

|

House

14695 SW 112TH CIR, DUNNELLON, FL, 34432
Spruce Creek Preserve 14117 SW 115TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$215,000

2 beds

|

2 baths

|

1,296 sq ft

|

House

14117 SW 115TH CIR, DUNNELLON, FL, 34432
Palm Cay 10881 SW 79TH TER, OCALA, FL, 34476, Ocala, FL 34476
$183,000

2 beds

|

2 baths

|

1,112 sq ft

|

House

10881 SW 79TH TER, OCALA, FL, 34476
Community: Palm Cay
Palm Cay 8274 SW 106TH PL, OCALA, FL, 34481, Ocala, FL 34481
$161,000

2 beds

|

1 baths

|

768 sq ft

|

House

8274 SW 106TH PL, OCALA, FL, 34481
Community: Palm Cay
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.
Palm Cay 8449 SW 106TH PL, OCALA, FL, 34481, Ocala, FL 34481
$172,000

2 beds

|

2 baths

|

1,114 sq ft

|

House

8449 SW 106TH PL, OCALA, FL, 34481
Community: Palm Cay
Latitude Margaritaville 613 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$367,000

2 beds

|

2 baths

|

1,204 sq ft

|

House

613 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Stone Creek 9412 SW 53RD PL, OCALA, FL, 34481, Ocala, FL 34481
$289,500

2 beds

|

2 baths

|

1,432 sq ft

|

House

9412 SW 53RD PL, OCALA, FL, 34481
Community: Stone Creek
Latitude Margaritaville 757 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$460,000

2 beds

|

3 baths

|

1,743 sq ft

|

House

757 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
The Villages® 916 PASADENA WAY, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$350,000

3 beds

|

2 baths

|

1,663 sq ft

|

House

916 PASADENA WAY, THE VILLAGES, FL, 3215...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 2227 NORTH CREEK CT, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$370,000

3 beds

|

2 baths

|

1,902 sq ft

|

House

2227 NORTH CREEK CT, SUN CITY CENTER, FL...
Community: Sun City Center
The Villages® 3394 RIDGEWOOD PATH, THE VILLAGES, FL, 3..., The Villages, FL 32163
$429,900

3 beds

|

2 baths

|

1,559 sq ft

|

House

3394 RIDGEWOOD PATH, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 1701 PALM AIRE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$269,900

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

1701 PALM AIRE DR, LADY LAKE, FL, 32159
Community: The Villages®
Latitude Margaritaville 443 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$429,000

3 beds

|

2 baths

|

1,563 sq ft

|

House

443 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Oak Run 8850 SW 116TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$210,000

2 beds

|

2 baths

|

1,077 sq ft

|

House

8850 SW 116TH PLACE RD, OCALA, FL, 34481
Community: Oak Run
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 2115 PLATINUM DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$624,999

3 beds

|

4 baths

|

2,737 sq ft

|

House

2115 PLATINUM DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Venetian Bay 3054 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$575,000

3 beds

|

4 baths

|

1,847 sq ft

|

Townhouse

3054 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Latitude Margaritaville 621 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$690,000

2 beds

|

3 baths

|

2,338 sq ft

|

House

621 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
The Villages® 3486 RABBIT RUN PATH, THE VILLAGES, FL, ..., The Villages, FL 32163
$525,000

3 beds

|

3 baths

|

2,016 sq ft

|

House

3486 RABBIT RUN PATH, THE VILLAGES, FL, ...
Community: The Villages®
Sun City Center 329 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$300,000

2 beds

|

2 baths

|

1,809 sq ft

|

Villa

329 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8084 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$345,000

3 beds

|

2 baths

|

2,032 sq ft

|

House

8084 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Del Webb Sunbridge 2928 VOYAGER AVE, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$429,000

3 beds

|

3 baths

|

1,854 sq ft

|

Townhouse

2928 VOYAGER AVE, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Spruce Creek Country Club 9073 SE 136TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$220,000

2 beds

|

2 baths

|

1,136 sq ft

|

House

9073 SE 136TH LOOP, SUMMERFIELD, FL, 344...
Mirada 31541 CANNON RUSH DR, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$385,000

2 beds

|

2 baths

|

1,770 sq ft

|

House

31541 CANNON RUSH DR, SAN ANTONIO, FL, 3...
Community: Mirada
Spruce Creek Country Club 9573 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$339,900

2 beds

|

2 baths

|

1,708 sq ft

|

House

9573 SE 124TH LOOP, SUMMERFIELD, FL, 344...

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3,631 homes near Winter Garden
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