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

3,958 homes near Winter Garden

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No reviews yet Del Webb Oasis
$400Ks - $1Ms
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $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
<$100k - $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
<$100k - $600Ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$200Ks - $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, FL? 55places can help!
Questions? Call us: (689) 407-5757
3.6 rating (46 reviews) Latitude Margaritaville
$300Ks - $700Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $800Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 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
4.5 rating (11 reviews) Spruce Creek Country Club
$200Ks - $500Ks
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 - $400Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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) Stonecrest
$200Ks - $600Ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
5 rating (7 reviews) Kings Ridge
$200Ks - $400Ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
5 rating (3 reviews) Twin Lakes
$200Ks - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $600Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.6 rating (5 reviews) Ocala Preserve
$200Ks - $600Ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$200Ks - $300Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $900Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (1 reviews) Cypress Lakes
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $900Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$200Ks - $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.
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
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
3.8 rating (6 reviews) Tampa Bay Golf and Countr...
$200Ks - $400Ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (8 reviews) Pennbrooke Fairways
$100Ks - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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
3.6 rating (5 reviews) Heritage Hills
$300Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Ocala Palms
$100Ks - $400Ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300Ks - $600Ks
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.
5 rating (5 reviews) SummerGlen
$200Ks - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 homes
5 rating (1 reviews) Legacy of Leesburg
$200Ks - $400Ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes
No reviews yet Breakaway Trails
$400Ks - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4 rating (2 reviews) Harbor Hills Country Club
$200Ks - $800Ks
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, FL? 55places can help!
Questions? Call us: (689) 407-5757
4.8 rating (6 reviews) Highland Lakes
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet 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
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Stonecrest 17563 SE 122ND TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$559,900

3 beds

|

3 baths

|

2,071 sq ft

|

House

17563 SE 122ND TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 1210 WEATON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$425,000

2 beds

|

2 baths

|

1,912 sq ft

|

House

1210 WEATON CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 2367 CAMDEN TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$350,000

3 beds

|

2 baths

|

1,397 sq ft

|

House

2367 CAMDEN TER, THE VILLAGES, FL, 32162
Community: The Villages®
Twin Lakes 4904 W FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772
$599,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

4904 W FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
The Villages® 8288 SE 177TH WINTERTHUR LOOP, THE VILLA..., The Villages, FL 32162
$359,000

3 beds

|

2 baths

|

1,997 sq ft

|

House

8288 SE 177TH WINTERTHUR LOOP, THE VILLA...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Esplanade at Wiregrass Ranch 4286 CAIROLI CT, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$457,709

3 beds

|

2 baths

|

1,925 sq ft

|

House

4286 CAIROLI CT, WESLEY CHAPEL, FL, 3354...
Vienna Square 2505 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$338,300

2 beds

|

2 baths

|

2,062 sq ft

|

House

2505 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
Heritage Hills 3755 SANIBEL ST, CLERMONT, FL, 34711, Clermont, FL 34711
$525,000

3 beds

|

3 baths

|

2,573 sq ft

|

House

3755 SANIBEL ST, CLERMONT, FL, 34711
Community: Heritage Hills
Twin Lakes 2765 REDBLUSH TER, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$514,395

2 beds

|

2 baths

|

1,889 sq ft

|

House

2765 REDBLUSH TER, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Summer Trees 6023 SPRUCE POINT CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128
$364,900

3 beds

|

2 baths

|

1,567 sq ft

|

House

6023 SPRUCE POINT CIR, PORT ORANGE, FL, ...
Community: Summer Trees
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.
Lakeside Landings 5312 GALLEY WAY, OXFORD, FL, 34484, Oxford, FL 34484
$275,000

3 beds

|

2 baths

|

1,705 sq ft

|

House

5312 GALLEY WAY, OXFORD, FL, 34484
Community: Lakeside Landings
The Villages® 1667 OSPREY AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$274,500

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1667 OSPREY AVE, THE VILLAGES, FL, 32162
Community: The Villages®
Trilogy® Orlando 115 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$380,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

115 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
Twin Lakes 2426 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$275,000

2 beds

|

2 baths

|

1,261 sq ft

|

Halfplex

2426 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
The Lakes at Harmony 3447 FEATHERGRASS CT, HARMONY, FL, 34773, Harmony, FL 34773
$495,000

5 beds

|

4 baths

|

3,300 sq ft

|

House

3447 FEATHERGRASS CT, HARMONY, FL, 34773
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Sunbridge 2793 NATURE VIEW RD, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$689,000

4 beds

|

3 baths

|

2,761 sq ft

|

House

2793 NATURE VIEW RD, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
New Pelican Bay Daytona Beach 144 HERRING GULL CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$345,000

3 beds

|

2 baths

|

2,196 sq ft

|

House

144 HERRING GULL CT, DAYTONA BEACH, FL, ...
The Villages® 924 FIGWOOD LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$582,700

3 beds

|

2 baths

|

2,145 sq ft

|

House

924 FIGWOOD LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 3433 NESTLEBRANCH AVE, THE VILLAGES, FL,..., The Villages, FL 32163
$549,900

3 beds

|

2 baths

|

1,957 sq ft

|

House

3433 NESTLEBRANCH AVE, THE VILLAGES, FL,...
Community: The Villages®
The Villages® 3118 SWEETGUM ST, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$350,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

3118 SWEETGUM ST, THE VILLAGES, FL, 3216...
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® 2700 PLAINRIDGE LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162
$390,000

3 beds

|

2 baths

|

1,546 sq ft

|

House

2700 PLAINRIDGE LOOP, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 529 VALENCIA PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$250,000

2 beds

|

2 baths

|

1,040 sq ft

|

House

529 VALENCIA PL, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 741 ROYAL PALM AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$182,000

2 beds

|

2 baths

|

1,056 sq ft

|

Manufactured Home

741 ROYAL PALM AVE, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 2125 HORIZON RUN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$1,549,900

3 beds

|

2 baths

|

2,911 sq ft

|

House

2125 HORIZON RUN, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1046 RIDGELAND PATH, THE VILLAGES, FL, 3..., The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

1046 RIDGELAND PATH, THE VILLAGES, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 928 NUTHATCH AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$358,000

3 beds

|

2 baths

|

1,416 sq ft

|

Villa

928 NUTHATCH AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 17145 SE 93RD YONDEL CIR, THE VILLAGES, ..., The Villages, FL 32162
$319,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

17145 SE 93RD YONDEL CIR, THE VILLAGES, ...
Community: The Villages®
Sun City Center 1909 EAST VIEW DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$469,000

3 beds

|

2 baths

|

2,598 sq ft

|

House

1909 EAST VIEW DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Oak Run 8450 SW 115TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481
$239,900

3 beds

|

2 baths

|

1,689 sq ft

|

House

8450 SW 115TH STREET RD, OCALA, FL, 3448...
Community: Oak Run
The Villages® 517 SAN PEDRO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$275,000

2 beds

|

2 baths

|

1,066 sq ft

|

House

517 SAN PEDRO DR, LADY LAKE, 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.
The Villages® 1053 ALCOVE LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$773,000

3 beds

|

2 baths

|

1,770 sq ft

|

House

1053 ALCOVE LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
On Top of the World 9153 SW 83RD TER E, OCALA, FL, 34481, Ocala, FL 34481
$255,000

2 beds

|

2 baths

|

1,858 sq ft

|

Villa

9153 SW 83RD TER E, OCALA, FL, 34481
Community: On Top of the World
Highland Fairways 3130 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810
$229,900

2 beds

|

2 baths

|

1,210 sq ft

|

House

3130 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
Southshore Bay 17228 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$279,900

2 beds

|

3 baths

|

1,737 sq ft

|

Villa

17228 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Sun City Center 2335 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$314,900

3 beds

|

2 baths

|

1,322 sq ft

|

House

2335 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Twin Lakes 2672 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$671,999

3 beds

|

3 baths

|

2,935 sq ft

|

House

2672 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Breakaway Trails 4 CREEK BEND WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$769,000

5 beds

|

3 baths

|

3,625 sq ft

|

House

4 CREEK BEND WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
The Villages® 1986 ALTAMONTE WAY, THE VILLAGES, FL, 32..., The Villages, FL 32162
$545,000

3 beds

|

2 baths

|

2,123 sq ft

|

Villa

1986 ALTAMONTE WAY, THE VILLAGES, FL, 32...
Community: The Villages®
Valencia Lakes 15731 CRYSTAL WATERS DR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$400,000

3 beds

|

2 baths

|

1,986 sq ft

|

House

15731 CRYSTAL WATERS DR, WIMAUMA, FL, 33...
Community: Valencia Lakes
On Top of the World 8635 SW 95TH ST G, OCALA, FL, 34481, Ocala, FL 34481
$89,900

2 beds

|

2 baths

|

1,677 sq ft

|

Villa

8635 SW 95TH ST G, OCALA, FL, 34481
Community: On Top of the World

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3,958 homes near Winter Garden
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