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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
Stonecrest 17490 SE 110TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$330,000

3 beds

|

2 baths

|

1,471 sq ft

|

House

17490 SE 110TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 1721 SUNSET RIDGE DR, THE VILLAGES, FL, ..., The Villages, FL 32162
$1,530,000

4 beds

|

3 baths

|

3,897 sq ft

|

House

1721 SUNSET RIDGE DR, THE VILLAGES, FL, ...
Community: The Villages®
New Tampa Bay Golf and Country Club 10232 BUNCOMBE WAY, SAN ANTONIO, FL, 335..., San Antonio, FL 33576
$375,000

3 beds

|

2 baths

|

1,397 sq ft

|

House

10232 BUNCOMBE WAY, SAN ANTONIO, FL, 335...
Esplanade at Wiregrass Ranch 4795 FRECCIA LOOP, WESLEY CHAPEL, FL, 33..., Wesley Chapel, FL 33543
$909,900

3 beds

|

3 baths

|

3,087 sq ft

|

House

4795 FRECCIA LOOP, WESLEY CHAPEL, FL, 33...
Palms at Serenoa 3371 YELLOWTOP LOOP, CLERMONT, FL, 34714, Clermont, FL 34714
$392,990

2 beds

|

2 baths

|

1,700 sq ft

|

House

3371 YELLOWTOP LOOP, CLERMONT, FL, 34714
Community: Palms at Serenoa
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 5107 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484
$418,000

4 beds

|

3 baths

|

2,180 sq ft

|

House

5107 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
Venetian Bay 266 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$459,000

5 beds

|

3 baths

|

2,508 sq ft

|

House

266 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
On Top of the World 8166 SW 80TH TER, OCALA, FL, 34476, Ocala, FL 34476
$265,000

3 beds

|

2 baths

|

1,487 sq ft

|

House

8166 SW 80TH TER, OCALA, FL, 34476
Community: On Top of the World
Venetian Bay 610 MURA CT, NEW SMYRNA BEACH, FL, 32168, New Smyrna Beach, FL 32168
$987,900

5 beds

|

5 baths

|

3,535 sq ft

|

House

610 MURA CT, NEW SMYRNA BEACH, FL, 32168
Community: Venetian Bay
The Villages® 2192 KERWOOD LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32162
$309,000

2 beds

|

2 baths

|

1,142 sq ft

|

House

2192 KERWOOD LOOP, THE VILLAGES, FL, 321...
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.
Spruce Creek Country Club 9417 SE 132ND LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$229,900

2 beds

|

2 baths

|

1,147 sq ft

|

House

9417 SE 132ND LOOP, SUMMERFIELD, FL, 344...
Four Seasons at Orlando 7928 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$590,000

3 beds

|

2 baths

|

2,066 sq ft

|

House

7928 HANSON BAY PL, KISSIMMEE, FL, 34747
VillageWalk at Lake Nona 11754 BARLETTA DR, ORLANDO, FL, 32827, Orlando, FL 32827
$624,900

4 beds

|

2 baths

|

2,211 sq ft

|

House

11754 BARLETTA DR, ORLANDO, FL, 32827
Lakes of Mount Dora 8780 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$539,000

3 beds

|

2 baths

|

1,682 sq ft

|

House

8780 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
The Villages® 1727 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$210,000

2 beds

|

2 baths

|

1,180 sq ft

|

Manufactured Home

1727 HILTON HEAD BLVD, LADY LAKE, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 16967 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162
$345,000

3 beds

|

2 baths

|

1,514 sq ft

|

House

16967 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
Trilogy® Orlando 119 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$359,000

2 beds

|

2 baths

|

1,556 sq ft

|

House

119 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
Solivita 806 VIA COMO ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$360,000

2 beds

|

2 baths

|

1,652 sq ft

|

House

806 VIA COMO ST, POINCIANA, FL, 34759
Community: Solivita
The Villages® 17848 SE 87TH BOURNE AVE, THE VILLAGES, ..., The Villages, FL 32162
$295,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

17848 SE 87TH BOURNE AVE, THE VILLAGES, ...
Community: The Villages®
Lakeside Landings 4987 BELTED KINGFISHER DR, OXFORD, FL, 3..., Oxford, FL 34484
$355,900

3 beds

|

2 baths

|

1,916 sq ft

|

House

4987 BELTED KINGFISHER DR, OXFORD, FL, 3...
Community: Lakeside Landings
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® 1007 ALOHA WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$163,900

2 beds

|

2 baths

|

1,152 sq ft

|

Mobile Home

1007 ALOHA WAY, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 2096 CALLAWAY DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$489,000

3 beds

|

2 baths

|

2,215 sq ft

|

House

2096 CALLAWAY DR, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 3810 COSMOS WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$379,900

3 beds

|

2 baths

|

1,501 sq ft

|

House

3810 COSMOS WAY, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1912 ARMONDO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$389,900

3 beds

|

2 baths

|

1,894 sq ft

|

House

1912 ARMONDO DR, THE VILLAGES, FL, 32159
Community: The Villages®
Southshore Bay 17576 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$344,900

2 beds

|

3 baths

|

1,747 sq ft

|

Villa

17576 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Arlington Ridge 26821 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748
$465,000

3 beds

|

2 baths

|

2,282 sq ft

|

House

26821 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
The Villages® 1338 NEUPORT PATH, THE VILLAGES, FL, 321..., The Villages, FL 32163
$475,000

3 beds

|

2 baths

|

2,030 sq ft

|

House

1338 NEUPORT PATH, THE VILLAGES, FL, 321...
Community: The Villages®
New Marion Landing 6241 SW 84TH PL, OCALA, FL, 34476, Ocala, FL 34476
$260,000

3 beds

|

2 baths

|

1,808 sq ft

|

House

6241 SW 84TH PL, OCALA, FL, 34476
Community: Marion Landing
Plantation at Leesburg 4419 NOTTOWAY DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$294,900

3 beds

|

2 baths

|

1,863 sq ft

|

House

4419 NOTTOWAY DR, LEESBURG, FL, 34748
Liberty Village 7796 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$299,900

3 beds

|

2 baths

|

1,755 sq ft

|

House

7796 SW 74TH LOOP, OCALA, FL, 34481
Community: Liberty Village
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.
On Top of the World 7987 SW 89TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$360,000

3 beds

|

2 baths

|

1,874 sq ft

|

House

7987 SW 89TH CIR, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8952 SW 79TH LN, OCALA, FL, 34481, Ocala, FL 34481
$324,900

2 beds

|

2 baths

|

1,747 sq ft

|

House

8952 SW 79TH LN, OCALA, FL, 34481
Community: On Top of the World
The Villages® 1711 FRANCISCO ST, THE VILLAGES, FL, 321..., The Villages, FL 32159
$269,000

2 beds

|

2 baths

|

1,094 sq ft

|

Villa

1711 FRANCISCO ST, THE VILLAGES, FL, 321...
Community: The Villages®
VillageWalk at Lake Nona 11863 DELFINA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$450,000

2 beds

|

2 baths

|

1,541 sq ft

|

Halfplex

11863 DELFINA LN, ORLANDO, FL, 32827
New The Villages® 4878 CHITTY CHATTY RUN, THE VILLAGES, FL..., The Villages, FL 32163
$1,000,000

4 beds

|

3 baths

|

2,296 sq ft

|

House

4878 CHITTY CHATTY RUN, THE VILLAGES, FL...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Highlands 20936 ROYAL ST GEORGES LN, LEESBURG, FL,..., Leesburg, FL 34748
$449,000

3 beds

|

2 baths

|

2,380 sq ft

|

House

20936 ROYAL ST GEORGES LN, LEESBURG, FL,...
Community: Royal Highlands
Spruce Creek Country Club 8772 SE 130TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$460,000

2 beds

|

2 baths

|

1,870 sq ft

|

House

8772 SE 130TH LOOP, SUMMERFIELD, FL, 344...
VillageWalk at Lake Nona 11937 BIANCA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$475,000

3 beds

|

3 baths

|

1,820 sq ft

|

Townhouse

11937 BIANCA LN, ORLANDO, FL, 32827
Sun City Center 1110 JASMINE CREEK CT, SUN CITY CENTER, ..., Sun City Center, FL 33573
$399,000

2 beds

|

2 baths

|

1,956 sq ft

|

House

1110 JASMINE CREEK CT, SUN CITY CENTER, ...
Community: Sun City Center
The Villages® 1282 FORT LAWN LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162
$359,000

3 beds

|

2 baths

|

1,488 sq ft

|

House

1282 FORT LAWN LOOP, THE VILLAGES, FL, 3...
Community: The Villages®

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3,958 homes near Winter Garden
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