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

3,654 homes near Winter Garden

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4 rating (17 reviews) The Villages®
$100ks - $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
$100ks - $800ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.2 rating (10 reviews) Stone Creek
$200ks - $500ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.7 rating (18 reviews) Solivita
$300ks - $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
4.5 rating (11 reviews) Spruce Creek Country Club
$100ks - $400ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
5 rating (2 reviews) Plantation at Leesburg
$100ks - $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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
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.
3.6 rating (48 reviews) Latitude Margaritaville
$300ks - $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
4.6 rating (5 reviews) Ocala Preserve
$100ks - $500ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
3.8 rating (4 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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.
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
5 rating (1 reviews) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4 rating (7 reviews) Tampa Bay Golf and Countr...
$200ks - $500ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (3 reviews) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 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
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.
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $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
$300ks - $900ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
3.6 rating (5 reviews) Heritage Hills
$200ks - $400ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 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 (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 homes
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
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 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
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
12...3
New The Villages® 9232 SE 168TH COOK PL, THE VILLAGES, FL,..., The Villages, FL 32162
$365,000

3 beds

|

2 baths

|

1,733 sq ft

|

Villa

9232 SE 168TH COOK PL, THE VILLAGES, FL,...
Community: The Villages®
New Ocala Preserve 4537 NW 53RD CT, OCALA, FL, 34482, Ocala, FL 34482
$429,500

3 beds

|

2 baths

|

1,862 sq ft

|

House

4537 NW 53RD CT, OCALA, FL, 34482
Community: Ocala Preserve
New The Villages® 9469 SE 176TH SAFFOLD ST, THE VILLAGES, ..., The Villages, FL 32162
$349,000

3 beds

|

2 baths

|

1,505 sq ft

|

House

9469 SE 176TH SAFFOLD ST, THE VILLAGES, ...
Community: The Villages®
New Palms at Serenoa 3645 BLUE SAGE LOOP, CLERMONT, FL, 34714, Clermont, FL 34714
$475,000

4 beds

|

2 baths

|

2,069 sq ft

|

House

3645 BLUE SAGE LOOP, CLERMONT, FL, 34714
Community: Palms at Serenoa
New On Top of the World 8667 SW 97TH ST C, OCALA, FL, 34481, Ocala, FL 34481
$160,000

2 beds

|

2 baths

|

1,541 sq ft

|

Villa

8667 SW 97TH ST C, 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 The Villages® 8015 SE 174TH BELHAVEN LOOP, THE VILLAGE..., The Villages, FL 32162
$275,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

8015 SE 174TH BELHAVEN LOOP, THE VILLAGE...
Community: The Villages®
New On Top of the World 7953 SW 89TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$279,900

2 beds

|

2 baths

|

1,343 sq ft

|

House

7953 SW 89TH LOOP, OCALA, FL, 34476
Community: On Top of the World
New Four Seasons at Orlando 7624 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747
$349,500

2 beds

|

2 baths

|

1,437 sq ft

|

House

7624 SAND PIERRE CT, KISSIMMEE, FL, 3474...
New Cherrywood 5947 SW 98TH STREET RD, OCALA, FL, 34476, Ocala, FL 34476
$195,000

2 beds

|

2 baths

|

1,158 sq ft

|

House

5947 SW 98TH STREET RD, OCALA, FL, 34476
Community: Cherrywood
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.
New Spruce Creek South 17590 SE 96TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$189,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

17590 SE 96TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
New Quail Meadow 5028 NW 34TH PL, OCALA, FL, 34482, Ocala, FL 34482
$424,000

3 beds

|

2 baths

|

2,213 sq ft

|

House

5028 NW 34TH PL, OCALA, FL, 34482
Community: Quail Meadow
New Sun City Center 202 BEDFORD TRL 109, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$72,500

2 beds

|

2 baths

|

960 sq ft

|

Condo

202 BEDFORD TRL 109, SUN CITY CENTER, FL...
Community: Sun City Center
New Solivita 3461 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$300,000

2 beds

|

2 baths

|

1,499 sq ft

|

Villa

3461 FALLBROOK DR, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Sun City Center 1804 PACIFIC DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$379,900

2 beds

|

3 baths

|

2,053 sq ft

|

House

1804 PACIFIC DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
New Scottish Highlands 27 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$215,000

2 beds

|

2 baths

|

1,252 sq ft

|

House

27 GORDON CT, LEESBURG, FL, 34788
Community: Scottish Highlands
New Sun City Center 608 LA JOLLA AVE, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$249,900

2 beds

|

2 baths

|

1,852 sq ft

|

House

608 LA JOLLA AVE, SUN CITY CENTER, FL, 3...
Community: Sun City Center
New Plantation at Leesburg 3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748
$299,999

3 beds

|

2 baths

|

1,868 sq ft

|

House

3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474...
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.
New Gatherings of Lake Nona 7517 LAUREATE BLVD 4403, ORLANDO, FL, 32..., Orlando, FL 32827
$329,000

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7517 LAUREATE BLVD 4403, ORLANDO, FL, 32...
New Southshore Bay 5336 WINDY GROVE DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$565,000

3 beds

|

3 baths

|

2,651 sq ft

|

House

5336 WINDY GROVE DR, WIMAUMA, FL, 33598
Community: Southshore Bay
New The Villages® 2088 VISION CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$689,000

3 beds

|

2 baths

|

2,013 sq ft

|

House

2088 VISION CT, THE VILLAGES, FL, 32163
Community: The Villages®
New Foxwood Lake Estates 1704 QUAIL HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$140,000

2 beds

|

2 baths

|

1,372 sq ft

|

Manufactured Home

1704 QUAIL HILL DR, LAKELAND, FL, 33810
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New The Country Club of Mount Dora 1901 PARK FOREST BLVD, MOUNT DORA, FL, 3..., Mount Dora, FL 32757
$539,000

3 beds

|

2 baths

|

2,286 sq ft

|

House

1901 PARK FOREST BLVD, MOUNT DORA, FL, 3...
New Sullivan Ranch 20926 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757
$349,900

3 beds

|

2 baths

|

1,440 sq ft

|

House

20926 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
New Foxwood Lake Estates 4966 DEERWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$174,900

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

4966 DEERWOOD DR, LAKELAND, FL, 33810
New Twin Lakes 4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772
$420,000

2 beds

|

2 baths

|

1,624 sq ft

|

House

4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...
Community: Twin Lakes
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.
New The Villages® 1738 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$775,000

4 beds

|

3 baths

|

2,959 sq ft

|

House

1738 AUGUSTINE DR, THE VILLAGES, FL, 321...
Community: The Villages®
New Foxwood Lake Estates 1798 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$164,900

3 beds

|

2 baths

|

1,176 sq ft

|

Manufactured Home

1798 FOX HILL DR, LAKELAND, FL, 33810
New Spruce Creek Preserve 11876 SW 137TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432
$249,900

3 beds

|

2 baths

|

1,760 sq ft

|

House

11876 SW 137TH LOOP, DUNNELLON, FL, 3443...
New Highlands Ridge 5004 BIRKDALE DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$299,000

2 beds

|

2 baths

|

1,648 sq ft

|

Villa

5004 BIRKDALE DR, AVON PARK, FL, 33825
Community: Highlands Ridge
New Four Seasons at Orlando 1999 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$429,980

2 beds

|

2 baths

|

1,557 sq ft

|

Villa

1999 KEY BAY TRL, KISSIMMEE, FL, 34747
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Lakes at Laurel Highlands 2933 IVY LAKE CT, LAKELAND, FL, 33811, Lakeland, FL 33811
$389,500

5 beds

|

3 baths

|

2,674 sq ft

|

House

2933 IVY LAKE CT, LAKELAND, FL, 33811
New The Villages® 5511 HEAD WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$394,900

3 beds

|

2 baths

|

1,708 sq ft

|

House

5511 HEAD WAY, THE VILLAGES, FL, 32163
Community: The Villages®
New High Vista at Ridgewood Lakes 116 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$309,000

2 beds

|

2 baths

|

1,776 sq ft

|

House

116 FLEMING LN, DAVENPORT, FL, 33837
New The Villages® 603 ROBIN LANE AVE, WILDWOOD, FL, 34785, Wildwood, FL 34785
$159,900

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

603 ROBIN LANE AVE, WILDWOOD, FL, 34785
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.
New The Villages® 1714 EL NINO ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$289,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1714 EL NINO ST, THE VILLAGES, FL, 32162
Community: The Villages®
New The Villages® 2530 FOXBRIDGE TER, THE VILLAGES, FL, 32..., The Villages, FL 32162
$324,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

2530 FOXBRIDGE TER, THE VILLAGES, FL, 32...
Community: The Villages®
New Plantation at Leesburg 25845 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

2,047 sq ft

|

House

25845 GLEN EAGLE DR, LEESBURG, FL, 34748
New Oak Run 6541 SW 111TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$279,500

3 beds

|

2 baths

|

1,808 sq ft

|

House

6541 SW 111TH LOOP, OCALA, FL, 34476
Community: Oak Run
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New The Villages® 3284 THEODORE TER, THE VILLAGES, FL, 321..., The Villages, FL 32163
$674,900

3 beds

|

3 baths

|

2,033 sq ft

|

House

3284 THEODORE TER, THE VILLAGES, FL, 321...
Community: The Villages®
New The Villages® 717 TANGERINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$220,000

2 beds

|

2 baths

|

1,332 sq ft

|

Manufactured Home

717 TANGERINE DR, LADY LAKE, FL, 32159
Community: The Villages®

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