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Winter Garden, FL 55+ active adult communities & homes for sale - Page 71

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
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
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
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
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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
Lakes at Laurel Highlands 2667 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811
$338,500

3 beds

|

2 baths

|

1,710 sq ft

|

House

2667 CANYON CREST DR, LAKELAND, FL, 3381...
Heritage Landings 2667 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811
$338,500

3 beds

|

2 baths

|

1,710 sq ft

|

House

2667 CANYON CREST DR, LAKELAND, FL, 3381...
Community: Heritage Landings
JB Ranch 6264 SW 89TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476
$314,900

2 beds

|

2 baths

|

1,813 sq ft

|

House

6264 SW 89TH LANE RD, OCALA, FL, 34476
Community: JB Ranch
Valencia del Sol 15567 CORONA DEL MAR DR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$525,000

4 beds

|

3 baths

|

2,127 sq ft

|

House

15567 CORONA DEL MAR DR, WIMAUMA, FL, 33...
Community: Valencia del Sol
Sun City Center 1209 LITCHFIELD DR 42, SUN CITY CENTER, ..., Sun City Center, FL 33573
$224,318

3 beds

|

2 baths

|

1,573 sq ft

|

Condo

1209 LITCHFIELD DR 42, SUN CITY CENTER, ...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 856 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$559,900

2 beds

|

2 baths

|

1,862 sq ft

|

House

856 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Sun City Center 1722 COCO PALM CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$275,000

3 beds

|

2 baths

|

1,619 sq ft

|

House

1722 COCO PALM CIR, SUN CITY CENTER, FL,...
Community: Sun City Center
Spruce Creek Country Club 13914 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$354,900

3 beds

|

2 baths

|

1,958 sq ft

|

House

13914 SE 96TH CIR, SUMMERFIELD, FL, 3449...
Latitude Margaritaville 472 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$419,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

472 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
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.
Sandpiper Golf & Country Club 6325 EGRET DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$255,000

3 beds

|

2 baths

|

1,441 sq ft

|

House

6325 EGRET DR, LAKELAND, FL, 33809
The Villages® 1573 NORFOLK AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$949,000

3 beds

|

2 baths

|

1,871 sq ft

|

House

1573 NORFOLK AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
Pelican Bay Daytona Beach 348 BOB WHITE CT 9, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$225,000

3 beds

|

3 baths

|

1,527 sq ft

|

Condo

348 BOB WHITE CT 9, DAYTONA BEACH, FL, 3...
On Top of the World 8655 SW 98TH STREET RD G, OCALA, FL, 344..., Ocala, FL 34481
$154,900

2 beds

|

2 baths

|

1,424 sq ft

|

Villa

8655 SW 98TH STREET RD G, OCALA, FL, 344...
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
Latitude Margaritaville 664 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$609,900

2 beds

|

2 baths

|

1,922 sq ft

|

House

664 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
The Villages® 2845 CHARITY LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$327,500

2 beds

|

2 baths

|

1,206 sq ft

|

House

2845 CHARITY LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Sun City Center 906 BLUEWATER DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$269,000

2 beds

|

2 baths

|

1,756 sq ft

|

House

906 BLUEWATER DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Pine Run Estates 10260 SW 92ND CT, OCALA, FL, 34481, Ocala, FL 34481
$129,900

2 beds

|

1 baths

|

864 sq ft

|

House

10260 SW 92ND CT, OCALA, FL, 34481
Community: Pine Run Estates
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® 1133 DEL TORO DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$299,900

2 beds

|

2 baths

|

1,332 sq ft

|

House

1133 DEL TORO DR, THE VILLAGES, FL, 3215...
Community: The Villages®
Sun City Center 901 HENDON CT, SUN CITY CENTER, FL, 3357..., Sun City Center, FL 33573
$139,000

2 beds

|

2 baths

|

1,087 sq ft

|

Condo

901 HENDON CT, SUN CITY CENTER, FL, 3357...
Community: Sun City Center
Stone Creek 8392 SW 54TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$305,000

2 beds

|

2 baths

|

1,433 sq ft

|

House

8392 SW 54TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Highlands Ridge 2848 E SPINNAKER DR, AVON PARK, FL, 3382..., Avon Park, FL 33825
$108,900

2 beds

|

2 baths

|

1,100 sq ft

|

Mobile Home

2848 E SPINNAKER DR, AVON PARK, FL, 3382...
Community: Highlands Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 12546 SE 92ND TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$350,000

2 beds

|

2 baths

|

2,119 sq ft

|

House

12546 SE 92ND TER, SUMMERFIELD, FL, 3449...
On Top of the World 9109 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$229,800

2 beds

|

2 baths

|

2,164 sq ft

|

House

9109 SW 93RD CIR, OCALA, FL, 34481
Community: On Top of the World
Scottish Highlands 304 BRIGADOON CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$200,000

2 beds

|

2 baths

|

1,278 sq ft

|

House

304 BRIGADOON CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 664 TERNBERRY FOREST DR, THE VILLAGES, F..., The Villages, FL 32162
$1,595,000

3 beds

|

3 baths

|

3,100 sq ft

|

House

664 TERNBERRY FOREST DR, THE VILLAGES, F...
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.
Marion Landing 6942 SW 86TH ST, OCALA, FL, 34476, Ocala, FL 34476
$124,999

3 beds

|

2 baths

|

1,200 sq ft

|

Mobile Home

6942 SW 86TH ST, OCALA, FL, 34476
Community: Marion Landing
Solivita 543 VIA VITALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$425,000

3 beds

|

3 baths

|

2,235 sq ft

|

House

543 VIA VITALE CT, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 1422 SEGOVIA PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$399,999

3 beds

|

2 baths

|

2,044 sq ft

|

House

1422 SEGOVIA PL, THE VILLAGES, FL, 32162
Community: The Villages®
Four Seasons at Orlando 2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$379,990

2 beds

|

2 baths

|

1,778 sq ft

|

House

2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Trilogy® Orlando 133 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736
$300,000

2 beds

|

2 baths

|

1,483 sq ft

|

House

133 CREPE MYRTLE DR, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Foxwood Lake Estates 1576 LONGBOW DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$199,000

3 beds

|

2 baths

|

1,152 sq ft

|

Manufactured Home

1576 LONGBOW DR, LAKELAND, FL, 33810
Summer Trees 109 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$270,809

2 beds

|

2 baths

|

1,259 sq ft

|

House

109 UNDERBRUSH TRL, PORT ORANGE, FL, 321...
Community: Summer Trees
The Lakes at Harmony 3473 MIDDLEBROOK PL, HARMONY, FL, 34773, Harmony, FL 34773
$398,022

4 beds

|

2 baths

|

2,064 sq ft

|

House

3473 MIDDLEBROOK PL, HARMONY, FL, 34773
The Villages® 1850 KYRLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$975,000

3 beds

|

2 baths

|

2,227 sq ft

|

House

1850 KYRLE TER, THE VILLAGES, FL, 32162
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® 1899 GROESSER PL, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$315,000

2 beds

|

2 baths

|

1,203 sq ft

|

Villa

1899 GROESSER PL, THE VILLAGES, FL, 3216...
Community: The Villages®
Four Seasons at Orlando 2074 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$610,000

3 beds

|

2 baths

|

2,130 sq ft

|

House

2074 FLORA PASS PL, KISSIMMEE, FL, 34747
Solivita 328 INDIAN WELLS AVE, POINCIANA, FL, 347..., Poinciana, FL 34759
$323,500

2 beds

|

2 baths

|

1,548 sq ft

|

House

328 INDIAN WELLS AVE, POINCIANA, FL, 347...
Community: Solivita
Foxwood Lake Estates 4903 DEERWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$162,999

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

4903 DEERWOOD DR, LAKELAND, FL, 33810
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Twin Lakes 4921 CATALPA DR, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$539,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

4921 CATALPA DR, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Royal Harbor 3592 TROPICAL SEAS LOOP, TAVARES, FL, 32..., Tavares, FL 32778
$317,000

2 beds

|

2 baths

|

1,452 sq ft

|

House

3592 TROPICAL SEAS LOOP, TAVARES, FL, 32...
Community: Royal Harbor

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