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Winter Garden, FL 55+ active adult communities & homes for sale - Page 12

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
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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
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
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 (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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 (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
Del Webb Orlando 1032 SALAMANCA PL, DAVENPORT, FL, 33837, Davenport, FL 33837
$319,900

2 beds

|

2 baths

|

1,455 sq ft

|

House

1032 SALAMANCA PL, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Solivita 505 MILLIFIORA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$290,000

2 beds

|

2 baths

|

1,548 sq ft

|

House

505 MILLIFIORA LN, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 1041 REIDVILLE RD, THE VILLAGES, FL, 321..., The Villages, FL 32162
$379,000

2 beds

|

2 baths

|

1,196 sq ft

|

Villa

1041 REIDVILLE RD, THE VILLAGES, FL, 321...
Community: The Villages®
Highland Lakes 6122 WADE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$266,500

3 beds

|

2 baths

|

1,961 sq ft

|

House

6122 WADE ST, LEESBURG, FL, 34748
Community: Highland Lakes
Venetian Bay 3207 MEDICI BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$799,900

4 beds

|

3 baths

|

2,708 sq ft

|

House

3207 MEDICI BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Kings Ridge 2225 ELVERSON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$349,900

3 beds

|

2 baths

|

1,892 sq ft

|

House

2225 ELVERSON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Kings Ridge 2319 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$350,000

3 beds

|

2 baths

|

1,875 sq ft

|

House

2319 ADDISON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Scottish Highlands 1907 TWEED CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$229,000

2 beds

|

2 baths

|

1,495 sq ft

|

House

1907 TWEED CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Stone Creek 8367 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$380,560

4 beds

|

2 baths

|

1,850 sq ft

|

House

8367 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
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.
Stone Creek 8454 SW 55TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$448,980

2 beds

|

2 baths

|

1,943 sq ft

|

House

8454 SW 55TH STREET RD, OCALA, FL, 34481
Community: Stone Creek
Scottish Highlands 1416 ORKNEY DR, LEESBURG, FL, 34788, Leesburg, FL 34788
$250,000

3 beds

|

2 baths

|

1,736 sq ft

|

House

1416 ORKNEY DR, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 519 WESTON MANOR DR, THE VILLAGES, FL, 3..., The Villages, FL 32162
$374,900

3 beds

|

2 baths

|

1,505 sq ft

|

House

519 WESTON MANOR DR, THE VILLAGES, FL, 3...
Community: The Villages®
Sun City Center 1222 HADDINGTON CIR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$179,900

2 beds

|

2 baths

|

1,448 sq ft

|

Condo

1222 HADDINGTON 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
Stone Creek 5346 SW 86TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$325,290

2 beds

|

2 baths

|

1,405 sq ft

|

House

5346 SW 86TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 8443 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$437,800

2 beds

|

2 baths

|

1,889 sq ft

|

House

8443 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 5958 SW 86TH AVENUE RD, OCALA, FL, 34481, Ocala, FL 34481
$340,960

2 beds

|

2 baths

|

1,655 sq ft

|

House

5958 SW 86TH AVENUE RD, OCALA, FL, 34481
Community: Stone Creek
The Villages® 731 CORTEZ AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$275,000

2 beds

|

2 baths

|

1,336 sq ft

|

House

731 CORTEZ AVE, THE VILLAGES, FL, 32159
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.
Oak Run 6279 SW 84TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$563,420

3 beds

|

4 baths

|

2,808 sq ft

|

House

6279 SW 84TH AVE, OCALA, FL, 34481
Community: Oak Run
Stone Creek 5315 SW 86TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$354,950

2 beds

|

2 baths

|

1,655 sq ft

|

House

5315 SW 86TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
The Villages® 2584 BUTTONWOOD RUN, THE VILLAGES, FL, 3..., The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,488 sq ft

|

House

2584 BUTTONWOOD RUN, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 5375 WERDEBAUGH WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163
$589,000

3 beds

|

2 baths

|

1,923 sq ft

|

House

5375 WERDEBAUGH WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 235 INDIAN WELLS AVE, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$324,900

2 beds

|

3 baths

|

1,935 sq ft

|

House

235 INDIAN WELLS AVE, KISSIMMEE, FL, 347...
Community: Solivita
Sun City Center 2629 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$235,000

2 beds

|

2 baths

|

1,829 sq ft

|

Condo

2629 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Spruce Creek South 17841 SE 106TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$216,000

2 beds

|

2 baths

|

1,446 sq ft

|

House

17841 SE 106TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Cresswind at Victoria Gardens 261 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724
$617,000

3 beds

|

3 baths

|

2,804 sq ft

|

House

261 OLD MOSS CIR, DELAND, FL, 32724
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® 1365 BRIER CREEK CIR, THE VILLAGES, FL, ..., The Villages, FL 32162
$1,299,000

3 beds

|

2 baths

|

3,679 sq ft

|

House

1365 BRIER CREEK CIR, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 3067 MELVILLE LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32162
$380,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

3067 MELVILLE LOOP, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 1040 DENTSVILLE LN, THE VILLAGES, FL, 32..., The Villages, FL 32162
$447,000

3 beds

|

2 baths

|

2,006 sq ft

|

House

1040 DENTSVILLE LN, THE VILLAGES, FL, 32...
Community: The Villages®
Valencia del Sol 15512 CORONA DEL MAR DR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$545,000

3 beds

|

3 baths

|

2,268 sq ft

|

House

15512 CORONA DEL MAR DR, WIMAUMA, FL, 33...
Community: Valencia del Sol
Tampa Bay Golf and Country Club 29549 TEE SHOT DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$319,900

3 beds

|

2 baths

|

1,554 sq ft

|

House

29549 TEE SHOT DR, SAN ANTONIO, FL, 3357...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cresswind at Victoria Gardens 1369 HAYTON AVE, DELAND, FL, 32724, Deland, FL 32724
$309,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

1369 HAYTON AVE, DELAND, FL, 32724
Trilogy® Orlando 184 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736
$539,000

4 beds

|

3 baths

|

3,044 sq ft

|

House

184 CREPE MYRTLE DR, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Pine Run Estates 8917 SW 104TH PL, OCALA, FL, 34481, Ocala, FL 34481
$149,900

2 beds

|

2 baths

|

1,040 sq ft

|

House

8917 SW 104TH PL, OCALA, FL, 34481
Community: Pine Run Estates
The Villages® 1667 ABERNETHY PL, THE VILLAGES, FL, 321..., The Villages, FL 32162
$389,900

3 beds

|

2 baths

|

1,496 sq ft

|

House

1667 ABERNETHY PL, THE VILLAGES, FL, 321...
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.
Tohoqua Reserve 2744 SERENITY MEADOW DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744
$439,890

3 beds

|

2 baths

|

2,056 sq ft

|

House

2744 SERENITY MEADOW DR, KISSIMMEE, FL, ...
Community: Tohoqua Reserve
The Villages® 986 DAVEY LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$444,500

3 beds

|

2 baths

|

1,569 sq ft

|

House

986 DAVEY LN, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 9100 SE 170TH FONTAINE ST, THE VILLAGES,..., The Villages, FL 32162
$379,000

3 beds

|

2 baths

|

2,170 sq ft

|

House

9100 SE 170TH FONTAINE ST, THE VILLAGES,...
Community: The Villages®
The Villages® 8146 SE 177TH WINTERTHUR LOOP, THE VILLA..., The Villages, FL 32162
$650,000

3 beds

|

2 baths

|

2,022 sq ft

|

House

8146 SE 177TH WINTERTHUR LOOP, THE VILLA...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sullivan Ranch 30215 BRETTON LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$490,000

4 beds

|

3 baths

|

2,687 sq ft

|

House

30215 BRETTON LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
Sun City Center 1405 JACOBSON CIR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$299,900

3 beds

|

2 baths

|

1,453 sq ft

|

House

1405 JACOBSON CIR, SUN CITY CENTER, FL, ...
Community: Sun City Center

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