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

3,537 homes near Winter Garden

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5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
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 - $500Ks
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 - $600Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
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3.6 rating (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
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 - $500Ks
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 - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Pelican Bay Daytona Beach
$100Ks - $400Ks
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
$100Ks - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 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
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
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 - $500Ks
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
$300Ks - $1Ms
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, FL? 55places can help!
Questions? Call us: (689) 407-5757
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) Sandpiper Golf & Coun...
$200Ks - $400Ks
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
Breakaway Trails
$400Ks - $800Ks
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, 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
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
Pine Run Estates
$100Ks - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
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
Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
The Villages® 17600 SE 88TH COVINGTON CIR, THE VILLAGE..., The Villages, FL 32162
$660,000

3 beds

|

2 baths

|

2,580 sq ft

|

House

17600 SE 88TH COVINGTON CIR, THE VILLAGE...
Community: The Villages®
The Villages® 289 ZINGALE LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$319,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

289 ZINGALE LN, THE VILLAGES, FL, 32163
Community: The Villages®
Solivita 537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$549,900

3 beds

|

3 baths

|

2,441 sq ft

|

House

537 MONTAGE LN, KISSIMMEE, FL, 34759
Community: Solivita
New Latitude Margaritaville 597 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$539,900

3 beds

|

2 baths

|

1,848 sq ft

|

House

597 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
The Villages® 3072 BERWYN WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$359,900

2 beds

|

2 baths

|

1,392 sq ft

|

House

3072 BERWYN WAY, THE VILLAGES, FL, 32162
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® 2377 LONGBOW TRL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$360,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

2377 LONGBOW TRL, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 4156 NADIRA CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$449,000

3 beds

|

2 baths

|

1,794 sq ft

|

House

4156 NADIRA CT, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 610 DANBURY ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$360,000

3 beds

|

2 baths

|

1,407 sq ft

|

Villa

610 DANBURY ST, THE VILLAGES, FL, 32162
Community: The Villages®
New Plantation at Leesburg 25205 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$255,000

2 beds

|

2 baths

|

1,328 sq ft

|

House

25205 CRANES ROOST CIR, LEESBURG, FL, 34...
New Ocala Palms 2305 NW 51ST TER, OCALA, FL, 34482, Ocala, FL 34482
$419,000

2 beds

|

2 baths

|

1,736 sq ft

|

House

2305 NW 51ST TER, OCALA, FL, 34482
Community: Ocala Palms
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® 1712 GALLOWAY DR, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$504,995

3 beds

|

2 baths

|

1,696 sq ft

|

Villa

1712 GALLOWAY DR, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1614 CHERRY HILL RD, THE VILLAGES, FL, 3..., The Villages, FL 32159
$224,400

2 beds

|

2 baths

|

1,336 sq ft

|

Manufactured Home

1614 CHERRY HILL RD, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 3459 OLDHAM LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$424,900

3 beds

|

2 baths

|

1,446 sq ft

|

Villa

3459 OLDHAM LN, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1701 PALM AIRE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$265,000

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

1701 PALM AIRE DR, THE VILLAGES, FL, 321...
Community: The Villages®
New Scottish Highlands 1605 SELKIRK DR, LEESBURG, FL, 34788, Leesburg, FL 34788
$235,000

2 beds

|

2 baths

|

1,284 sq ft

|

House

1605 SELKIRK DR, LEESBURG, FL, 34788
Community: Scottish Highlands
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1159 ISLE OF PALMS PATH, THE VILLAGES, F..., The Villages, FL 32162
$429,900

2 beds

|

2 baths

|

1,887 sq ft

|

House

1159 ISLE OF PALMS PATH, THE VILLAGES, F...
Community: The Villages®
The Villages® 3374 CASTLEGATE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163
$299,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

3374 CASTLEGATE CT, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 3377 QUAIL HOLLOW CT, THE VILLAGES, FL, ..., The Villages, FL 32163
$334,900

3 beds

|

2 baths

|

1,488 sq ft

|

House

3377 QUAIL HOLLOW CT, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 2671 COLLINGTON DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$270,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2671 COLLINGTON DR, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 16838 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162
$345,000

3 beds

|

2 baths

|

1,648 sq ft

|

House

16838 SE 93RD CUTHBERT CIR, THE VILLAGES...
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® 8544 SE 177TH BARTRAM LOOP, THE VILLAGES..., The Villages, FL 32162
$309,000

3 beds

|

2 baths

|

1,481 sq ft

|

House

8544 SE 177TH BARTRAM LOOP, THE VILLAGES...
Community: The Villages®
New The Lakes at Harmony 3343 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$385,000

3 beds

|

2 baths

|

2,090 sq ft

|

House

3343 SAGEBRUSH ST, HARMONY, FL, 34773
The Villages® 2142 MARGARITA DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$380,000

3 beds

|

2 baths

|

1,904 sq ft

|

House

2142 MARGARITA DR, THE VILLAGES, FL, 321...
Community: The Villages®
New The Villages® 1064 ALCOVE LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$799,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

1064 ALCOVE LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Lake Jovita Golf and Country Club 13514 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525
$625,000

4 beds

|

2 baths

|

2,108 sq ft

|

House

13514 THOROUGHBRED DR, DADE CITY, FL, 33...
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
New The Villages® 1234 DUSTIN DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$177,900

2 beds

|

2 baths

|

1,392 sq ft

|

Manufactured Home

1234 DUSTIN DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 2304 FRINGE TREE TRL, THE VILLAGES, FL, ..., The Villages, FL 32162
$569,000

3 beds

|

2 baths

|

1,939 sq ft

|

House

2304 FRINGE TREE TRL, THE VILLAGES, FL, ...
Community: The Villages®
New Royal Harbor 6170 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778
$345,000

3 beds

|

2 baths

|

1,535 sq ft

|

House

6170 SAILBOAT AVE, TAVARES, FL, 32778
Community: Royal Harbor
New Southshore Bay 17011 CLEAR CORK DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$229,000

2 beds

|

2 baths

|

1,406 sq ft

|

Villa

17011 CLEAR CORK DR, WIMAUMA, FL, 33598
Community: Southshore Bay
Cresswind at Victoria Gardens 317 BELLINGRATH TER, DELAND, FL, 32724, Deland, FL 32724
$359,000

3 beds

|

2 baths

|

2,240 sq ft

|

House

317 BELLINGRATH TER, DELAND, FL, 32724
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.
Tampa Bay Golf and Country Club 9524 ROLLING CIR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$450,000

3 beds

|

2 baths

|

2,065 sq ft

|

House

9524 ROLLING CIR, SAN ANTONIO, FL, 33576
Spruce Creek Country Club 12900 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$374,900

3 beds

|

2 baths

|

2,149 sq ft

|

House

12900 SE 97TH TERRACE RD, SUMMERFIELD, F...
Ocala Palms 5140 NW 25TH LOOP, OCALA, FL, 34482, Ocala, FL 34482
$245,000

2 beds

|

2 baths

|

1,569 sq ft

|

House

5140 NW 25TH LOOP, OCALA, FL, 34482
Community: Ocala Palms
Stonecrest 12333 SE 177TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$364,000

3 beds

|

2 baths

|

1,904 sq ft

|

House

12333 SE 177TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
New Baytree 579 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778
$218,000

2 beds

|

2 baths

|

1,024 sq ft

|

Villa

579 JUNIPER WAY, TAVARES, FL, 32778
Community: Baytree
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 12762 SE 92ND TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$279,900

2 beds

|

2 baths

|

1,274 sq ft

|

House

12762 SE 92ND TER, SUMMERFIELD, FL, 3449...
Venetian Bay 3447 LUNA BELLA LN, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168
$495,000

3 beds

|

3 baths

|

2,167 sq ft

|

House

3447 LUNA BELLA LN, NEW SMYRNA BEACH, FL...
Community: Venetian Bay
Sandpiper Golf & Country Club 6381 EGRET DR 28, LAKELAND, FL, 33809, Lakeland, FL 33809
$239,000

2 beds

|

2 baths

|

941 sq ft

|

Villa

6381 EGRET DR 28, LAKELAND, FL, 33809
The Villages® 1422 SEGOVIA PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$424,900

3 beds

|

2 baths

|

2,044 sq ft

|

House

1422 SEGOVIA PL, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 2864 MANOR DOWNS, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$485,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

2864 MANOR DOWNS, THE VILLAGES, FL, 3216...
Community: The Villages®

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3,537 homes near Winter Garden
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