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

3,573 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 - $2Ms
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
<$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
$100Ks - $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
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 - $500Ks
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 - $500Ks
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 - $900Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
$100Ks - $500Ks
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? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $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 - $500Ks
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
$300Ks - $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) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$400Ks - $900Ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
Want to learn more about 55+ communities in Winter Garden? 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...
$200Ks - $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
$200Ks - $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 - $400Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
$300Ks - $1Ms
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$400Ks - $900Ks
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 - $1Ms
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
4.8 rating (6 reviews) Highland Lakes
$200Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$300Ks - $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 - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Stone Creek 9672 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$329,000

2 beds

|

2 baths

|

1,545 sq ft

|

House

9672 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
The Villages® 3374 CASTLEGATE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163
$319,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

3374 CASTLEGATE CT, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 1738 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$749,999

4 beds

|

3 baths

|

2,959 sq ft

|

House

1738 AUGUSTINE DR, THE VILLAGES, FL, 321...
Community: The Villages®
Pennbrooke Fairways 321 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

1,894 sq ft

|

House

321 RANCHWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
On Top of the World 8443 SW 82ND LOOP, OCALA, FL, 34481, Ocala, FL 34481
$349,853

2 beds

|

2 baths

|

1,709 sq ft

|

House

8443 SW 82ND LOOP, 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
Summit Greens 2217 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711
$359,888

3 beds

|

2 baths

|

1,645 sq ft

|

House

2217 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
Sun City Center 1762 ATRIUM DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$239,000

2 beds

|

2 baths

|

1,227 sq ft

|

House

1762 ATRIUM DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Solivita 1384 HARBOR RIDGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$304,777

2 beds

|

2 baths

|

1,658 sq ft

|

House

1384 HARBOR RIDGE DR, KISSIMMEE, FL, 347...
Community: Solivita
Sun City Center 1205 DESERT HILLS DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$265,000

2 beds

|

2 baths

|

1,533 sq ft

|

House

1205 DESERT HILLS DR, SUN CITY CENTER, F...
Community: Sun City Center
Lake Ashton 4101 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$424,000

2 beds

|

2 baths

|

1,882 sq ft

|

House

4101 LIMERICK DR, LAKE WALES, FL, 33859
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.
Sun City Center 202 BEDFORD TRL APT 120, SUN CITY CENTER..., Sun City Center, FL 33573
$157,000

2 beds

|

2 baths

|

960 sq ft

|

Villa

202 BEDFORD TRL APT 120, SUN CITY CENTER...
Community: Sun City Center
Stone Creek 5309 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481
$427,690

2 beds

|

2 baths

|

1,889 sq ft

|

House

5309 SW 87TH TER, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 5339 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481
$531,450

3 beds

|

3 baths

|

2,483 sq ft

|

House

5339 SW 87TH TER, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 8175 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$366,250

4 beds

|

2 baths

|

1,850 sq ft

|

House

8175 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 8323 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$418,170

2 beds

|

2 baths

|

1,670 sq ft

|

House

8323 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Traditions at Lake Ruby 4150 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$279,900

3 beds

|

2 baths

|

1,831 sq ft

|

House

4150 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Kings Ridge 3667 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$365,000

2 beds

|

2 baths

|

1,552 sq ft

|

House

3667 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
SummerGlen 1748 SW 157TH PLACE RD, OCALA, FL, 34473, Ocala, FL 34473
$339,000

3 beds

|

2 baths

|

2,090 sq ft

|

House

1748 SW 157TH PLACE RD, OCALA, FL, 34473
Community: SummerGlen
The Villages® 1930 HARSTON TRL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$339,950

3 beds

|

2 baths

|

1,392 sq ft

|

House

1930 HARSTON TRL, THE VILLAGES, FL, 3216...
Community: The Villages®
New The Villages® 950 LADSON LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162
$395,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

950 LADSON LOOP, THE VILLAGES, FL, 32162
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.
Venetian Bay 3039 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$335,000

3 beds

|

3 baths

|

1,672 sq ft

|

House

3039 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
The Villages® 1642 PENNECAMP DR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$479,000

3 beds

|

2 baths

|

1,939 sq ft

|

House

1642 PENNECAMP DR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 1014 NASH LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162
$329,900

2 beds

|

2 baths

|

1,142 sq ft

|

House

1014 NASH LOOP, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 2258 PRESERVATION GREEN CT, SUN CITY CEN..., Sun City Center, FL 33573
$315,000

3 beds

|

2 baths

|

1,490 sq ft

|

House

2258 PRESERVATION GREEN CT, SUN CITY CEN...
Community: Sun City Center
Venetian Bay 3357 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$529,900

4 beds

|

3 baths

|

2,835 sq ft

|

House

3357 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3759 ORIENT AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$485,000

3 beds

|

2 baths

|

1,930 sq ft

|

House

3759 ORIENT AVE, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 2025 CASTANO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$300,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

2025 CASTANO PL, THE VILLAGES, FL, 32159
Community: The Villages®
Lake Ashton 4072 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$389,000

3 beds

|

2 baths

|

1,875 sq ft

|

House

4072 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Summit Greens 2817 FALCON RDG, CLERMONT, FL, 34711, Clermont, FL 34711
$508,000

3 beds

|

3 baths

|

2,300 sq ft

|

House

2817 FALCON RDG, CLERMONT, FL, 34711
Community: Summit Greens
Sandpiper Golf & Country Club 6098 MAGPIE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$365,000

3 beds

|

2 baths

|

2,006 sq ft

|

House

6098 MAGPIE DR, LAKELAND, FL, 33809
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® 1805 SAN LUIS LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$339,900

3 beds

|

2 baths

|

1,884 sq ft

|

House

1805 SAN LUIS LN, THE VILLAGES, FL, 3215...
Community: The Villages®
On Top of the World 9117 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$219,000

3 beds

|

2 baths

|

1,428 sq ft

|

House

9117 SW 93RD CIR, OCALA, FL, 34481
Community: On Top of the World
Latitude Margaritaville 710 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$565,000

2 beds

|

3 baths

|

1,743 sq ft

|

House

710 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Sun City Center 1426 INGRAM DR # 1426, SUN CITY CENTER, ..., Sun City Center, FL 33573
$225,000

2 beds

|

2 baths

|

1,642 sq ft

|

Condo

1426 INGRAM DR # 1426, SUN CITY CENTER, ...
Community: Sun City Center
Trilogy® Orlando 440 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$382,000

3 beds

|

2 baths

|

1,704 sq ft

|

House

440 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 217 LAKE CASSIDY DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$430,000

3 beds

|

2 baths

|

2,201 sq ft

|

House

217 LAKE CASSIDY DR, KISSIMMEE, FL, 3475...
Community: Solivita
The Villages® 1762 MEADOWLARK AVE, THE VILLAGES, FL, 3..., The Villages, FL 32162
$345,000

3 beds

|

2 baths

|

1,392 sq ft

|

Villa

1762 MEADOWLARK AVE, THE VILLAGES, FL, 3...
Community: The Villages®
Traditions at Lake Ruby 2885 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$205,000

2 beds

|

2 baths

|

1,400 sq ft

|

Villa

2885 ATTWATER LOOP, WINTER HAVEN, FL, 33...
Pennbrooke Fairways 1045 MEADOWBEND DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$281,900

3 beds

|

2 baths

|

1,570 sq ft

|

House

1045 MEADOWBEND DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Solivita 156 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$249,900

2 beds

|

2 baths

|

1,240 sq ft

|

House

156 GRAND CANAL DR, POINCIANA, FL, 34759
Community: Solivita

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3,573 homes near Winter Garden
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