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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? 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? 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? 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? 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
Palm Cay 10520 SW 85TH TER, OCALA, FL, 34481, Ocala, FL 34481
$125,000

2 beds

|

1 baths

|

768 sq ft

|

House

10520 SW 85TH TER, OCALA, FL, 34481
Community: Palm Cay
Solivita 801 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$537,500

3 beds

|

3 baths

|

2,761 sq ft

|

House

801 SAN RAPHAEL ST, POINCIANA, FL, 34759
Community: Solivita
Royal Harbor 5000 PORTSMOUTH ST, TAVARES, FL, 32778, Tavares, FL 32778
$359,900

3 beds

|

2 baths

|

1,732 sq ft

|

House

5000 PORTSMOUTH ST, TAVARES, FL, 32778
Community: Royal Harbor
The Villages® 2936 SUBER ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$404,900

3 beds

|

2 baths

|

1,593 sq ft

|

House

2936 SUBER ST, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 2708 LA POSADA DR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$319,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

2708 LA POSADA DR, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 6594 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$229,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6594 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
High Vista at Ridgewood Lakes 1010 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$269,000

3 beds

|

2 baths

|

1,422 sq ft

|

House

1010 HIGH VISTA DR, DAVENPORT, FL, 33837
Venetian Bay 3368 TUSCANO AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$360,000

3 beds

|

2 baths

|

1,848 sq ft

|

House

3368 TUSCANO AVE, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
The Villages® 1907 ANDERSON CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$750,000

3 beds

|

2 baths

|

2,110 sq ft

|

House

1907 ANDERSON CT, THE VILLAGES, FL, 3216...
Community: The Villages®
On Top of the World 8457 SW 97TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$499,900

2 beds

|

2 baths

|

2,097 sq ft

|

House

8457 SW 97TH CIR, OCALA, FL, 34481
Community: On Top of the World
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 7421 SW 110TH PL, OCALA, FL, 34476, Ocala, FL 34476
$249,999

2 beds

|

2 baths

|

1,668 sq ft

|

House

7421 SW 110TH PL, OCALA, FL, 34476
Community: Oak Run
Solivita 196 VENTANA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$254,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

196 VENTANA DR, POINCIANA, FL, 34759
Community: Solivita
The Villages® 1222 CAMERO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$439,900

3 beds

|

2 baths

|

1,880 sq ft

|

House

1222 CAMERO DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 8457 SE 177TH PENMAN PL, THE VILLAGES, F..., The Villages, FL 32162
$335,000

3 beds

|

2 baths

|

1,607 sq ft

|

Villa

8457 SE 177TH PENMAN PL, THE VILLAGES, F...
Community: The Villages®
Venetian Bay 424 LUNA BELLA LN 327, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$295,000

2 beds

|

2 baths

|

1,575 sq ft

|

Condo

424 LUNA BELLA LN 327, NEW SMYRNA BEACH,...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 104 GLOUCESTER BLVD 340, SUN CITY CENTER..., Sun City Center, FL 33573
$164,999

1 beds

|

2 baths

|

928 sq ft

|

Condo

104 GLOUCESTER BLVD 340, SUN CITY CENTER...
Community: Sun City Center
Stone Creek 8820 SW 58TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$337,500

2 beds

|

2 baths

|

1,469 sq ft

|

House

8820 SW 58TH STREET RD, OCALA, FL, 34481
Community: Stone Creek
Sun City Center 420 S BROCKFIELD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$380,000

2 beds

|

2 baths

|

1,656 sq ft

|

House

420 S BROCKFIELD DR, SUN CITY CENTER, FL...
Community: Sun City Center
Venetian Bay 3061 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$330,000

3 beds

|

3 baths

|

1,614 sq ft

|

House

3061 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Plantation at Leesburg 4801 SUMMERBRIDGE CIR, LEESBURG, FL, 347..., Leesburg, FL 34748
$413,000

3 beds

|

3 baths

|

3,267 sq ft

|

House

4801 SUMMERBRIDGE 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.
Southshore Bay 17583 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$585,000

3 beds

|

3 baths

|

2,634 sq ft

|

House

17583 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Ocala Palms 5470 NW 26TH LN, OCALA, FL, 34482, Ocala, FL 34482
$288,500

2 beds

|

2 baths

|

1,569 sq ft

|

House

5470 NW 26TH LN, OCALA, FL, 34482
Community: Ocala Palms
On Top of the World 9012 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$216,800

2 beds

|

2 baths

|

1,777 sq ft

|

House

9012 SW 91ST CIR, OCALA, FL, 34481
Community: On Top of the World
Pennbrooke Fairways 32900 CROOKED OAKS LN, LEESBURG, FL, 347..., Leesburg, FL 34748
$261,000

3 beds

|

2 baths

|

1,620 sq ft

|

House

32900 CROOKED OAKS LN, LEESBURG, FL, 347...
Community: Pennbrooke Fairways
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Southshore Bay 5329 WINDY GROVE DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$614,000

3 beds

|

3 baths

|

2,776 sq ft

|

House

5329 WINDY GROVE DR, WIMAUMA, FL, 33598
Community: Southshore Bay
Harbor Hills Country Club 39634 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$539,900

3 beds

|

2 baths

|

2,579 sq ft

|

House

39634 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Foxwood Lake Estates 5013 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810
$180,000

2 beds

|

2 baths

|

1,056 sq ft

|

Manufactured Home

5013 FOXWOOD BLVD, LAKELAND, FL, 33810
Latitude Margaritaville 542 DAIQUIRI PL, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$375,500

2 beds

|

2 baths

|

1,309 sq ft

|

House

542 DAIQUIRI PL, DAYTONA BEACH, FL, 3212...
Pine Run Estates 9920 SW 102ND PL, OCALA, FL, 34481, Ocala, FL 34481
$129,129

2 beds

|

1 baths

|

864 sq ft

|

House

9920 SW 102ND PL, OCALA, FL, 34481
Community: Pine Run Estates
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® 2602 YOUNG LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$339,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2602 YOUNG LN, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 9345 SE 171ST LE FLORE LN, THE VILLAGES,..., The Villages, FL 32162
$352,900

3 beds

|

2 baths

|

1,509 sq ft

|

House

9345 SE 171ST LE FLORE LN, THE VILLAGES,...
Community: The Villages®
Solivita 309 VESTRELLA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$339,900

3 beds

|

2 baths

|

1,590 sq ft

|

House

309 VESTRELLA DR, POINCIANA, FL, 34759
Community: Solivita
Plantation at Leesburg 3624 BELLE ROSE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$385,000

4 beds

|

3 baths

|

2,820 sq ft

|

House

3624 BELLE ROSE DR, LEESBURG, FL, 34748
On Top of the World 6590 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$229,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6590 SW 81ST LOOP, OCALA, FL, 34476
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
On Top of the World 7706 SW 89TH CT, OCALA, FL, 34481, Ocala, FL 34481
$359,900

2 beds

|

2 baths

|

1,747 sq ft

|

House

7706 SW 89TH CT, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8998 SW 75TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$461,000

3 beds

|

2 baths

|

2,118 sq ft

|

House

8998 SW 75TH LOOP, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8625 SW 94TH ST G, OCALA, FL, 34481, Ocala, FL 34481
$139,900

2 beds

|

2 baths

|

1,409 sq ft

|

Villa

8625 SW 94TH ST G, OCALA, FL, 34481
Community: On Top of the World
Lakes of Mount Dora 7873 CROSSWINDS WAY, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$480,000

2 beds

|

2 baths

|

1,592 sq ft

|

House

7873 CROSSWINDS WAY, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Latitude Margaritaville 162 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$399,999

2 beds

|

2 baths

|

1,466 sq ft

|

House

162 GYPSY PALACE LN, DAYTONA BEACH, FL, ...

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3,958 homes near Winter Garden
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