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

3,648 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 - $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
$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 - $700Ks
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 - $700Ks
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 - $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
<$100k - $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 - $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
$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
$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
No reviews yet Venetian Bay
$300Ks - $2Ms
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 - $500Ks
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
$400Ks - $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? 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 - $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 - $500Ks
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 | 1,024 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
$400Ks - $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
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $300Ks
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
Sun City Center 1207 HUNTINGTON GREENS DR, SUN CITY CENT..., Sun City Center, FL 33573
$260,000

2 beds

|

2 baths

|

1,318 sq ft

|

Condo

1207 HUNTINGTON GREENS DR, SUN CITY CENT...
Community: Sun City Center
The Villages® 1336 E SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$219,000

2 beds

|

2 baths

|

936 sq ft

|

Manufactured Home

1336 E SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
Vienna Square 1584 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$215,000

2 beds

|

2 baths

|

1,231 sq ft

|

Villa

1584 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
Del Webb Orlando 513 SAN SEBASTIAN CT, DAVENPORT, FL, 338..., Davenport, FL 33837
$412,000

3 beds

|

3 baths

|

2,036 sq ft

|

House

513 SAN SEBASTIAN CT, DAVENPORT, FL, 338...
Community: Del Webb Orlando
Twin Lakes 2600 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$659,000

3 beds

|

3 baths

|

2,935 sq ft

|

House

2600 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Arlington Ridge 26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748
$499,900

4 beds

|

3 baths

|

2,318 sq ft

|

House

26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
Spruce Creek Country Club 12470 SE 92ND TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$319,900

2 beds

|

2 baths

|

1,244 sq ft

|

House

12470 SE 92ND TER, SUMMERFIELD, FL, 3449...
Oak Run 8396 SW 109TH LN, OCALA, FL, 34481, Ocala, FL 34481
$198,000

2 beds

|

2 baths

|

1,224 sq ft

|

House

8396 SW 109TH LN, OCALA, FL, 34481
Community: Oak Run
Villas On The Green 13110 ELGAR PL, RIVERVIEW, FL, 33579, Riverview, FL 33579
$289,000

2 beds

|

2 baths

|

1,451 sq ft

|

House

13110 ELGAR PL, RIVERVIEW, FL, 33579
Community: Villas On The Green
Arlington Ridge 26939 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$315,000

2 beds

|

2 baths

|

1,631 sq ft

|

Villa

26939 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
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.
Arlington Ridge 4002 RICHMOND XING, LEESBURG, FL, 34748, Leesburg, FL 34748
$423,000

3 beds

|

2 baths

|

2,188 sq ft

|

House

4002 RICHMOND XING, LEESBURG, FL, 34748
Community: Arlington Ridge
On Top of the World 8755 SW 79TH PL, OCALA, FL, 34481, Ocala, FL 34481
$399,900

3 beds

|

2 baths

|

2,126 sq ft

|

House

8755 SW 79TH PL, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek Country Club 8649 SE 141ST PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$229,000

2 beds

|

2 baths

|

1,356 sq ft

|

Villa

8649 SE 141ST PL, SUMMERFIELD, FL, 34491
Sandpiper Golf & Country Club 6054 CRANE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$350,000

3 beds

|

2 baths

|

1,915 sq ft

|

House

6054 CRANE DR, LAKELAND, FL, 33809
Pennbrooke Fairways 32752 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,900

3 beds

|

2 baths

|

1,940 sq ft

|

House

32752 TIMBERWOOD 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
Del Webb Orlando 145 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$439,900

3 beds

|

2 baths

|

1,972 sq ft

|

House

145 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Spruce Creek Country Club 9464 SE 132ND LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$223,900

1 beds

|

2 baths

|

1,020 sq ft

|

House

9464 SE 132ND LOOP, SUMMERFIELD, FL, 344...
Highland Fairways 3130 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810
$199,900

2 beds

|

2 baths

|

1,210 sq ft

|

House

3130 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
Lakeside Landings 10274 JULIA ISLES AVE, OXFORD, FL, 34484, Oxford, FL 34484
$355,000

3 beds

|

2 baths

|

1,616 sq ft

|

House

10274 JULIA ISLES AVE, OXFORD, FL, 34484
Community: Lakeside Landings
Marion Landing 6190 SW 84TH PL, OCALA, FL, 34476, Ocala, FL 34476
$229,900

2 beds

|

2 baths

|

1,616 sq ft

|

House

6190 SW 84TH PL, OCALA, FL, 34476
Community: Marion Landing
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.
Four Seasons at Orlando 1598 WHITEWOOD CT, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$499,999

3 beds

|

2 baths

|

2,066 sq ft

|

House

1598 WHITEWOOD CT, KISSIMMEE, FL, 34747
Arlington Ridge 26821 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748
$429,000

3 beds

|

2 baths

|

2,282 sq ft

|

House

26821 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
Del Webb Orlando 208 ALMERIA WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$429,900

2 beds

|

2 baths

|

1,927 sq ft

|

House

208 ALMERIA WAY, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Arlington Ridge 27103 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748
$475,000

3 beds

|

2 baths

|

2,236 sq ft

|

House

27103 CAMERONS RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
The Villages® 16914 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

16914 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 25800 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,900

3 beds

|

2 baths

|

1,653 sq ft

|

House

25800 BELLE HELENE, LEESBURG, FL, 34748
The Villages® 1258 WEATON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$359,000

3 beds

|

2 baths

|

1,477 sq ft

|

House

1258 WEATON CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 16846 SE 80TH BELLAVISTA CIR, THE VILLAG..., The Villages, FL 32162
$575,000

2 beds

|

2 baths

|

1,906 sq ft

|

House

16846 SE 80TH BELLAVISTA CIR, THE VILLAG...
Community: The Villages®
Oak Run 8386 SW 109TH LN, OCALA, FL, 34481, Ocala, FL 34481
$196,000

2 beds

|

2 baths

|

1,224 sq ft

|

House

8386 SW 109TH LN, OCALA, FL, 34481
Community: Oak Run
Stone Creek 9125 SW 57TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$781,250

3 beds

|

4 baths

|

2,955 sq ft

|

House

9125 SW 57TH PLACE RD, OCALA, FL, 34481
Community: Stone Creek
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® 430 TARRSON BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$200,000

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

430 TARRSON BLVD, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 939 LIVINGSTON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162
$345,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

939 LIVINGSTON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Venetian Bay 3106 BORASSUS DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$370,000

3 beds

|

2 baths

|

1,505 sq ft

|

House

3106 BORASSUS DR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Sun City Center 1526 FORT DUQUESNA DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$369,900

2 beds

|

2 baths

|

2,031 sq ft

|

House

1526 FORT DUQUESNA DR, SUN CITY CENTER, ...
Community: Sun City Center
Ocala Palms 1921 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$194,900

2 beds

|

2 baths

|

929 sq ft

|

House

1921 NW 50TH CIR, OCALA, FL, 34482
Community: Ocala Palms
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Southshore Bay 17116 STAR BANKS ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$649,900

4 beds

|

3 baths

|

2,856 sq ft

|

House

17116 STAR BANKS ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Encore at Fishhawk Ranch 6122 WATERCOLOR DR, LITHIA, FL, 33547, Lithia, FL 33547
$649,000

2 beds

|

3 baths

|

2,670 sq ft

|

House

6122 WATERCOLOR DR, LITHIA, FL, 33547
On Top of the World 7809 SW 86TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$275,000

3 beds

|

2 baths

|

1,465 sq ft

|

House

7809 SW 86TH LOOP, OCALA, FL, 34476
Community: On Top of the World
Stonecrest 10952 SE 169TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$352,000

3 beds

|

2 baths

|

1,476 sq ft

|

House

10952 SE 169TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Solivita 1029 UMBRIA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$298,000

2 beds

|

2 baths

|

1,365 sq ft

|

House

1029 UMBRIA DR, POINCIANA, FL, 34759
Community: Solivita

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3,648 homes near Winter Garden
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