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Winter Garden, FL 55+ active adult communities & homes for sale - Page 76

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
The Villages® 1850 KYRLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$925,000

3 beds

|

2 baths

|

2,227 sq ft

|

House

1850 KYRLE TER, THE VILLAGES, FL, 32162
Community: The Villages®
Four Seasons at Orlando 2074 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$599,000

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
Twin Lakes 4921 CATALPA DR, ST CLOUD, FL, 34772, St Cloud, FL 34772
$539,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

4921 CATALPA DR, ST CLOUD, FL, 34772
Community: Twin Lakes
Royal Harbor 3592 TROPICAL SEAS LOOP, TAVARES, FL, 32..., Tavares, FL 32778
$314,000

2 beds

|

2 baths

|

1,452 sq ft

|

House

3592 TROPICAL SEAS LOOP, TAVARES, FL, 32...
Community: Royal Harbor
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 9566 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$270,701

2 beds

|

2 baths

|

1,556 sq ft

|

Villa

9566 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Sullivan Ranch 21846 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$290,000

2 beds

|

2 baths

|

1,437 sq ft

|

House

21846 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
High Vista at Ridgewood Lakes 247 TRAVIS LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$289,900

2 beds

|

2 baths

|

1,596 sq ft

|

House

247 TRAVIS LN, DAVENPORT, FL, 33837
Spruce Creek South 10339 SE 179TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$194,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

10339 SE 179TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Valencia Lakes 15948 COBBLE MILL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$327,000

3 beds

|

2 baths

|

1,593 sq ft

|

House

15948 COBBLE MILL DR, WIMAUMA, FL, 33598
Community: Valencia 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.
The Villages® 1923 USEPPA OAKS LN, THE VILLAGES, FL, 3..., The Villages, FL 32163
$379,900

3 beds

|

2 baths

|

1,875 sq ft

|

House

1923 USEPPA OAKS LN, THE VILLAGES, FL, 3...
Community: The Villages®
Tampa Bay Golf and Country Club 29418 SCHINNECOCK HILLS LN, SAN ANTONIO,..., San Antonio, FL 33576
$275,000

2 beds

|

2 baths

|

1,698 sq ft

|

Villa

29418 SCHINNECOCK HILLS LN, SAN ANTONIO,...
Palm Cay 10856 SW 79 AVE, OCALA, FL, 34476, Ocala, FL 34476
$228,000

3 beds

|

2 baths

|

1,080 sq ft

|

House

10856 SW 79 AVE, OCALA, FL, 34476
Community: Palm Cay
The Villages® 2167 KERWOOD LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32162
$394,500

3 beds

|

2 baths

|

1,467 sq ft

|

House

2167 KERWOOD LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Ocala Preserve 4474 NW 53RD AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$499,900

3 beds

|

3 baths

|

2,659 sq ft

|

House

4474 NW 53RD AVENUE RD, OCALA, FL, 34482
Community: Ocala Preserve
Spruce Creek Country Club 9033 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$249,900

3 beds

|

2 baths

|

1,726 sq ft

|

House

9033 SE 135TH LOOP, SUMMERFIELD, FL, 344...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Palm 5415 SWORDFERN CT, PORT ORANGE, FL, 3212..., Port Orange, FL 32128
$375,000

3 beds

|

3 baths

|

1,942 sq ft

|

House

5415 SWORDFERN CT, PORT ORANGE, FL, 3212...
Community: Royal Palm
SummerGlen 1683 SW 156TH LN, OCALA, FL, 34473, Ocala, FL 34473
$249,289

3 beds

|

2 baths

|

2,093 sq ft

|

House

1683 SW 156TH LN, OCALA, FL, 34473
Community: SummerGlen
Traditions at Lake Ruby 3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$369,900

4 beds

|

3 baths

|

2,404 sq ft

|

House

3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388...
Huntington at Hunter's Ridge 42 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$389,900

4 beds

|

2 baths

|

2,003 sq ft

|

House

42 HUNTINGTON PL, ORMOND BEACH, FL, 3217...
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® 5180 LEXINGTON CIR, WILDWOOD, FL, 34785, Wildwood, FL 34785
$224,000

3 beds

|

2 baths

|

1,932 sq ft

|

Manufactured Home

5180 LEXINGTON CIR, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 511 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$369,000

2 beds

|

2 baths

|

1,832 sq ft

|

House

511 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Carlsberg Estates on Lake Suzanne 364 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$284,900

2 beds

|

2 baths

|

1,387 sq ft

|

House

364 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Venetian Bay 3304 MODENA WAY, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$570,000

3 beds

|

2 baths

|

2,147 sq ft

|

House

3304 MODENA WAY, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Tampa Bay Golf and Country Club 9506 ROLLING CIR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$294,900

3 beds

|

3 baths

|

1,577 sq ft

|

House

9506 ROLLING CIR, SAN ANTONIO, FL, 33576
Highland Lakes 5616 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,900

2 beds

|

2 baths

|

2,003 sq ft

|

House

5616 LAVER ST, LEESBURG, FL, 34748
Community: Highland Lakes
On Top of the World 8674 SW 94TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$432,000

3 beds

|

3 baths

|

2,450 sq ft

|

House

8674 SW 94TH CIR, 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
Mirada 31524 MAGNA GULF LOOP, SAN ANTONIO, FL, ..., San Antonio, FL 33576
$305,000

2 beds

|

2 baths

|

1,405 sq ft

|

Villa

31524 MAGNA GULF LOOP, SAN ANTONIO, FL, ...
Community: Mirada
Summit Greens 791 WOLF CREEK ST, CLERMONT, FL, 34711, Clermont, FL 34711
$289,000

2 beds

|

2 baths

|

1,256 sq ft

|

House

791 WOLF CREEK ST, CLERMONT, FL, 34711
Community: Summit Greens
Lake Ashton 5337 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$359,000

3 beds

|

2 baths

|

1,833 sq ft

|

House

5337 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
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® 5371 WARM SPRINGS AVE, WILDWOOD, FL, 347..., Wildwood, FL 34785
$275,000

2 beds

|

1 baths

|

696 sq ft

|

House

5371 WARM SPRINGS AVE, WILDWOOD, FL, 347...
Community: The Villages®
Valencia del Sol 4922 SIENNA ISLES AVE, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$389,900

2 beds

|

2 baths

|

1,834 sq ft

|

Villa

4922 SIENNA ISLES AVE, WIMAUMA, FL, 3359...
Community: Valencia del Sol
Venetian Bay 2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$330,000

4 beds

|

3 baths

|

2,070 sq ft

|

House

2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Spruce Creek Country Club 9330 SE 132ND PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$379,900

3 beds

|

3 baths

|

2,333 sq ft

|

House

9330 SE 132ND PL, SUMMERFIELD, FL, 34491
The Villages® 1822 ATHENS LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$289,000

2 beds

|

2 baths

|

1,322 sq ft

|

Villa

1822 ATHENS LN, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 8798 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$335,000

3 beds

|

2 baths

|

2,145 sq ft

|

House

8798 SW 83RD CIR, OCALA, FL, 34481
Community: On Top of the World
Ocala Palms 5599 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482
$289,900

2 beds

|

2 baths

|

1,671 sq ft

|

House

5599 NW 18TH ST, OCALA, FL, 34482
Community: Ocala Palms
Venetian Bay 3056 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$544,990

3 beds

|

4 baths

|

1,847 sq ft

|

Townhouse

3056 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Trilogy® Orlando 134 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$340,000

3 beds

|

2 baths

|

1,644 sq ft

|

House

134 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Sun City Center 1001 OTTER MILL WAY 1001, SUN CITY CENTE..., Sun City Center, FL 33573
$215,000

2 beds

|

2 baths

|

1,810 sq ft

|

Condo

1001 OTTER MILL WAY 1001, SUN CITY CENTE...
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.

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3,497 homes
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