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Winter Garden, FL 55+ active adult communities & homes for sale - Page 27

3,769 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 (57 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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
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
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
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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 (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
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 (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 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
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 (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 (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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 (1 reviews) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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
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
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
5 rating (1 reviews) Cresswind at Victoria Gar...
$300ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 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.
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Highland Fairways
$100ks - $300ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Cresswind Lakewood Ranch
$400ks - $700ks
Cresswind Lakewood Ranch, Lakewood Ranch, FL
New and Resale | 55+ age-restricted | Built 2018 - present | 648 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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.
123...4
The Villages® 1951 GATEHOUSE TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$1,199,000

4 beds

|

2 baths

|

2,521 sq ft

|

House

1951 GATEHOUSE TER, THE VILLAGES, FL, 32...
Community: The Villages®
Kings Ridge 2284 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$429,000

3 beds

|

2 baths

|

1,892 sq ft

|

House

2284 ADDISON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Venetian Bay 3580 CASALTA CIR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$429,000

3 beds

|

2 baths

|

1,891 sq ft

|

Townhouse

3580 CASALTA CIR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Mirada 31516 CABANA RYE AVE, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$469,900

3 beds

|

3 baths

|

2,387 sq ft

|

House

31516 CABANA RYE AVE, SAN ANTONIO, FL, 3...
Community: Mirada
Valencia Lakes 4935 MARBLE SPRINGS CIR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$325,000

3 beds

|

2 baths

|

1,800 sq ft

|

Villa

4935 MARBLE SPRINGS CIR, WIMAUMA, FL, 33...
Community: Valencia Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Four Seasons at Orlando 1915 ESTUARY LN, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$499,900

3 beds

|

2 baths

|

2,202 sq ft

|

House

1915 ESTUARY LN, KISSIMMEE, FL, 34747
The Villages® 9188 SE 166TH SPRUNG LN, THE VILLAGES, F..., The Villages, FL 32162
$335,000

3 beds

|

2 baths

|

1,437 sq ft

|

Villa

9188 SE 166TH SPRUNG LN, THE VILLAGES, F...
Community: The Villages®
Venetian Bay 225 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$569,000

3 beds

|

2 baths

|

1,839 sq ft

|

House

225 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
The Villages® 1410 RED ASH PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$299,700

2 beds

|

2 baths

|

1,100 sq ft

|

House

1410 RED ASH PL, THE VILLAGES, FL, 32162
Community: The Villages®
Cindy Certified
33571 SKY BLOSSOM CIR, LEESBURG, FL, 347..., Leesburg, FL 34788
$319,900

4 beds

|

2 baths

|

1,850 sq ft

|

House

33571 SKY BLOSSOM CIR, LEESBURG, FL, 347...
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.
Carlsberg Estates on Lake Suzanne 4178 CANNES AVE, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$285,000

3 beds

|

3 baths

|

1,718 sq ft

|

House

4178 CANNES AVE, LAKE WALES, FL, 33859
Sun City Center 2404 NANTUCKET GLEN PL 2404, SUN CITY CE..., Sun City Center, FL 33573
$190,000

2 beds

|

2 baths

|

1,113 sq ft

|

Condo

2404 NANTUCKET GLEN PL 2404, SUN CITY CE...
Community: Sun City Center
Cindy Certified
30173 EMERALD FOREST DR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$419,990

3 beds

|

2 baths

|

2,066 sq ft

|

House

30173 EMERALD FOREST DR, MOUNT DORA, FL,...
Esplanade at McKinnon Groves 17742 SEDONA ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$916,028

3 beds

|

3 baths

|

2,475 sq ft

|

House

17742 SEDONA ST, WINTER GARDEN, FL, 3478...
Latitude Margaritaville 306 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$648,000

3 beds

|

3 baths

|

2,110 sq ft

|

House

306 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
The Villages® 7618 SE 171ST SUN VALLEY PL, THE VILLAGE..., The Villages, FL 32162
$330,000

2 beds

|

2 baths

|

1,332 sq ft

|

Villa

7618 SE 171ST SUN VALLEY PL, THE VILLAGE...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1811 MILFORD CIR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$429,900

3 beds

|

3 baths

|

1,961 sq ft

|

House

1811 MILFORD CIR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
The Villages® 823 SAN SALVADOR DR, THE VILLAGES, FL, 3..., The Villages, FL 32159
$489,000

3 beds

|

3 baths

|

2,402 sq ft

|

House

823 SAN SALVADOR DR, THE VILLAGES, FL, 3...
Community: The Villages®
Pennbrooke Fairways 228 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$270,000

2 beds

|

2 baths

|

1,568 sq ft

|

House

228 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Cindy Certified
11432 DRIFTING LEAF DR, RIVERVIEW, FL, 3..., Riverview, FL 33579
$629,000

4 beds

|

3 baths

|

2,468 sq ft

|

House

11432 DRIFTING LEAF DR, RIVERVIEW, 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.
Solivita 766 CARMEL LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$430,000

3 beds

|

3 baths

|

2,320 sq ft

|

House

766 CARMEL LN, KISSIMMEE, FL, 34759
Community: Solivita
Stone Creek 5866 SW 87TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$339,585

2 beds

|

2 baths

|

1,656 sq ft

|

House

5866 SW 87TH AVE, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 7199 SW 91ST CT, OCALA, FL, 34481, Ocala, FL 34481
$245,542

2 beds

|

2 baths

|

1,443 sq ft

|

House

7199 SW 91ST CT, OCALA, FL, 34481
Community: Stone Creek
The Villages® 8420 COUNTY RD A1, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$299,900

3 beds

|

2 baths

|

2,176 sq ft

|

Manufactured Home

8420 COUNTY RD A1, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 3452 BOSIE RUN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$950,000

3 beds

|

3 baths

|

2,192 sq ft

|

House

3452 BOSIE RUN, THE VILLAGES, FL, 32163
Community: The Villages®
Huntington at Hunter's Ridge 5 SHEAR WATER TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$379,000

3 beds

|

2 baths

|

1,826 sq ft

|

House

5 SHEAR WATER TRL, ORMOND BEACH, FL, 321...
The Villages® 745 DOWDING WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$650,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

745 DOWDING WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stonecrest 17879 SE 125TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$425,000

3 beds

|

3 baths

|

2,071 sq ft

|

House

17879 SE 125TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
Arbor Lakes 3676 E IBIS COVE CT, HERNANDO, FL, 34442, Hernando, FL 34442
$239,000

2 beds

|

2 baths

|

1,595 sq ft

|

House

3676 E IBIS COVE CT, HERNANDO, FL, 34442
Community: Arbor Lakes
The Villages® 1134 SOUTHERN SUN DR, THE VILLAGES, FL, ..., The Villages, FL 32162
$525,000

3 beds

|

2 baths

|

1,685 sq ft

|

Villa

1134 SOUTHERN SUN DR, THE VILLAGES, FL, ...
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.
Cindy Certified
17007 BLISTER WING DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$299,000

3 beds

|

2 baths

|

1,504 sq ft

|

House

17007 BLISTER WING DR, WIMAUMA, FL, 3359...
On Top of the World 9702 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$237,900

2 beds

|

2 baths

|

1,500 sq ft

|

House

9702 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
The Villages® 3602 PEPPERIDGE CIR, THE VILLAGES, FL, 3..., The Villages, FL 32163
$450,000

3 beds

|

2 baths

|

1,731 sq ft

|

House

3602 PEPPERIDGE CIR, THE VILLAGES, FL, 3...
Community: The Villages®
Esplanade at McKinnon Groves 11341 BOURBON ROSE CIR, WINTER GARDEN, F..., Winter Garden, FL 34787
$936,063

4 beds

|

5 baths

|

2,974 sq ft

|

House

11341 BOURBON ROSE CIR, WINTER GARDEN, F...
Sandpiper Golf & Country Club 6031 SANDERLING DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$265,000

2 beds

|

2 baths

|

1,520 sq ft

|

House

6031 SANDERLING DR, LAKELAND, FL, 33809
Cindy Certified
4711 SAN MARTINO DR, WESLEY CHAPEL, FL, ..., Wesley Chapel, FL 33543
$485,000

3 beds

|

2 baths

|

1,610 sq ft

|

House

4711 SAN MARTINO DR, WESLEY CHAPEL, FL, ...
On Top of the World 8640 SW 86TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$445,000

4 beds

|

2 baths

|

2,275 sq ft

|

House

8640 SW 86TH CIR, OCALA, FL, 34481
Community: On Top of the World
Cindy Certified
1947 ALTAVISTA CIR, LAKELAND, FL, 33810, Lakeland, FL 33810
$410,000

3 beds

|

2 baths

|

2,107 sq ft

|

House

1947 ALTAVISTA CIR, LAKELAND, FL, 33810
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2129 MARGARITA DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$387,900

3 beds

|

2 baths

|

1,694 sq ft

|

House

2129 MARGARITA DR, THE VILLAGES, FL, 321...
Community: The Villages®
The Country Club of Mount Dora 9076 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757
$349,000

3 beds

|

2 baths

|

1,587 sq ft

|

House

9076 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
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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3,769 homes
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