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Winter Garden, FL 55+ active adult communities & homes for sale - Page 69

3,497 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
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 rating (56 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
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
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
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
Venetian Bay
$300ks - $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.
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 (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 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
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 homes
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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 (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
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 (4 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
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) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 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 (5 reviews) Heritage Hills
$200ks - $400ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 homes
3.8 rating (5 reviews) Marion Landing
$100ks - $300ks
Marion Landing, Ocala, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 homes
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
Quail Meadow
$200ks - $400ks
Quail Meadow, Ocala, FL
Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 homes
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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.
12...3
Heritage Hills 3550 FAIRWATERS CT C, CLERMONT, FL, 3471..., Clermont, FL 34711
$289,990

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3550 FAIRWATERS CT C, CLERMONT, FL, 3471...
Community: Heritage Hills
Stonecrest 11351 SE 175TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$269,500

3 beds

|

2 baths

|

1,717 sq ft

|

House

11351 SE 175TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Spruce Creek Country Club 8955 SE 118TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$344,900

2 beds

|

2 baths

|

2,270 sq ft

|

House

8955 SE 118TH LN, SUMMERFIELD, FL, 34491
Spruce Creek Country Club 13324 SE 91ST COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$330,000

2 beds

|

2 baths

|

1,870 sq ft

|

House

13324 SE 91ST COURT RD, SUMMERFIELD, FL,...
Stonecrest 17187 SE 116TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$479,900

3 beds

|

3 baths

|

2,026 sq ft

|

House

17187 SE 116TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
JB Ranch 6388 SW 89TH STREET RD, OCALA, FL, 34479, Ocala, FL 34479
$333,900

4 beds

|

2 baths

|

2,039 sq ft

|

House

6388 SW 89TH STREET RD, OCALA, FL, 34479
Community: JB Ranch
Stone Creek 5472 SW 85TH AVENUE RD, OCALA, FL, 34481, Ocala, FL 34481
$294,000

2 beds

|

2 baths

|

1,433 sq ft

|

House

5472 SW 85TH AVENUE RD, OCALA, FL, 34481
Community: Stone Creek
Alhambra Villas Condominiums 249 N HILL AVE 30, DELAND, FL, 32724, Deland, FL 32724
$190,500

2 beds

|

2 baths

|

1,043 sq ft

|

Condo

249 N HILL AVE 30, DELAND, FL, 32724
Sun City Center 930 VILLEROY GREENS DR, SUN CITY CENTER,..., Sun City Center, FL 33573
$325,000

2 beds

|

2 baths

|

2,014 sq ft

|

Condo

930 VILLEROY GREENS DR, SUN CITY CENTER,...
Community: Sun City Center
Traditions at Lake Ruby 2925 DAYTON DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$284,500

3 beds

|

2 baths

|

2,109 sq ft

|

House

2925 DAYTON DR, WINTER HAVEN, FL, 33884
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.
Lakes of Mount Dora 2389 PAWTUCKET PASS, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$522,000

3 beds

|

2 baths

|

2,048 sq ft

|

House

2389 PAWTUCKET PASS, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Quail Meadow 3340 NW 44TH CT, OCALA, FL, 34482, Ocala, FL 34482
$235,000

3 beds

|

2 baths

|

1,265 sq ft

|

House

3340 NW 44TH CT, OCALA, FL, 34482
Community: Quail Meadow
Quail Meadow 3276 NW 44TH CT, OCALA, FL, 34482, Ocala, FL 34482
$230,000

3 beds

|

2 baths

|

1,224 sq ft

|

House

3276 NW 44TH CT, OCALA, FL, 34482
Community: Quail Meadow
Pelican Bay Daytona Beach 196 GRAY DOVE CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119
$274,000

3 beds

|

3 baths

|

1,833 sq ft

|

Townhouse

196 GRAY DOVE CT, DAYTONA BEACH, FL, 321...
Marion Landing 8373 SW 62ND CT, OCALA, FL, 34476, Ocala, FL 34476
$165,000

2 beds

|

2 baths

|

1,506 sq ft

|

House

8373 SW 62ND CT, OCALA, FL, 34476
Community: Marion Landing
Sun City Center 2345 GLENMORE CIR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$109,900

2 beds

|

2 baths

|

984 sq ft

|

Condo

2345 GLENMORE CIR, 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
The Villages® 1399 HOLLY HILL AVE, THE VILLAGES, FL, 3..., The Villages, FL 32162
$329,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

1399 HOLLY HILL AVE, THE VILLAGES, FL, 3...
Community: The Villages®
Heritage Hills 3201 SONESTA CT A, CLERMONT, FL, 34711, Clermont, FL 34711
$298,500

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3201 SONESTA CT A, CLERMONT, FL, 34711
Community: Heritage Hills
Spruce Creek Country Club 8516 SE 137TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$239,000

2 beds

|

2 baths

|

1,296 sq ft

|

House

8516 SE 137TH LOOP, SUMMERFIELD, FL, 344...
The Villages® 17766 SE 91ST POPLAR TER, THE VILLAGES, ..., The Villages, FL 32162
$297,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

17766 SE 91ST POPLAR TER, THE VILLAGES, ...
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® 304 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$304,000

2 beds

|

2 baths

|

1,360 sq ft

|

House

304 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
VillageWalk at Lake Nona 12077 ULETA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$950,000

5 beds

|

4 baths

|

4,093 sq ft

|

House

12077 ULETA LN, ORLANDO, FL, 32827
On Top of the World 8123 SW 95TH CT, OCALA, FL, 34481, Ocala, FL 34481
$579,900

3 beds

|

3 baths

|

2,490 sq ft

|

House

8123 SW 95TH CT, OCALA, FL, 34481
Community: On Top of the World
Four Seasons at Orlando 7661 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747
$424,900

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

7661 SAND PIERRE CT, KISSIMMEE, FL, 3474...
On Top of the World 10621 SW 98TH LN, OCALA, FL, 34481, Ocala, FL 34481
$440,000

3 beds

|

3 baths

|

2,963 sq ft

|

House

10621 SW 98TH LN, OCALA, FL, 34481
Community: On Top of the World
Twin Lakes 4909 W FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772
$499,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

4909 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...
Community: Twin Lakes
The Villages® 2403 ST GEORGE AVE, THE VILLAGES, FL, 32..., The Villages, FL 32162
$485,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

2403 ST GEORGE AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 9685 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$310,000

2 beds

|

2 baths

|

1,873 sq ft

|

House

9685 SE 136TH PL, SUMMERFIELD, FL, 34491
Oak Run 10824 SW 90TH TER, OCALA, FL, 34481, Ocala, FL 34481
$176,000

2 beds

|

2 baths

|

960 sq ft

|

House

10824 SW 90TH TER, OCALA, FL, 34481
Community: Oak Run
Ocala Palms 2305 NW 51ST TER, OCALA, FL, 34482, Ocala, FL 34482
$419,000

2 beds

|

2 baths

|

1,736 sq ft

|

House

2305 NW 51ST TER, 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® 926 LONG LEAF LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$439,900

3 beds

|

2 baths

|

1,541 sq ft

|

House

926 LONG LEAF LN, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1514 CERVANTES PL, THE VILLAGES, FL, 321..., The Villages, FL 32159
$625,000

3 beds

|

2 baths

|

2,308 sq ft

|

House

1514 CERVANTES PL, THE VILLAGES, FL, 321...
Community: The Villages®
Tampa Bay Golf and Country Club 29636 TEE SHOT DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$309,000

3 beds

|

2 baths

|

1,762 sq ft

|

House

29636 TEE SHOT DR, SAN ANTONIO, FL, 3357...
On Top of the World 8820 SW 104TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$385,711

2 beds

|

2 baths

|

2,104 sq ft

|

House

8820 SW 104TH CIR, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek Country Club 9921 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$289,400

2 beds

|

2 baths

|

1,872 sq ft

|

House

9921 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Arlington Ridge 26821 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748
$349,000

2 beds

|

2 baths

|

2,282 sq ft

|

House

26821 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
Lake Ashton 5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$345,000

2 beds

|

2 baths

|

1,677 sq ft

|

House

5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Sun City Center 2608 NEWCOMB CT 2608, SUN CITY CENTER, F..., Sun City Center, FL 33573
$190,000

2 beds

|

2 baths

|

1,645 sq ft

|

Condo

2608 NEWCOMB CT 2608, SUN CITY CENTER, F...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 3399 NW 56TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$599,900

3 beds

|

3 baths

|

2,763 sq ft

|

House

3399 NW 56TH AVE, OCALA, FL, 34482
Community: Ocala Preserve
On Top of the World 9972 SW 106TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$463,555

2 beds

|

2 baths

|

2,019 sq ft

|

House

9972 SW 106TH CIR, OCALA, FL, 34481
Community: On Top of the World
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.

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3,497 homes
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