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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
Royal Highlands 4925 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$275,000

2 beds

|

2 baths

|

1,226 sq ft

|

House

4925 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 1010 SIERRA BLANCA CT, THE VILLAGES, FL,..., The Villages, FL 32159
$550,000

3 beds

|

2 baths

|

2,250 sq ft

|

House

1010 SIERRA BLANCA CT, THE VILLAGES, FL,...
Community: The Villages®
The Villages® 16827 SE 92ND LANCE CT, THE VILLAGES, FL..., The Villages, FL 32162
$349,000

3 beds

|

2 baths

|

1,437 sq ft

|

House

16827 SE 92ND LANCE CT, THE VILLAGES, FL...
Community: The Villages®
The Villages® 2954 HEINY PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$684,900

4 beds

|

2 baths

|

2,828 sq ft

|

House

2954 HEINY PL, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 923 OLEANDER ST, THE VILLAGES, FL, 32159, The Villages, FL 32159
$475,000

3 beds

|

2 baths

|

2,076 sq ft

|

House

923 OLEANDER ST, THE VILLAGES, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 631 INDEPENDENCE PATH, THE VILLAGES, FL,..., The Villages, FL 32163
$955,000

4 beds

|

2 baths

|

2,606 sq ft

|

House

631 INDEPENDENCE PATH, THE VILLAGES, FL,...
Community: The Villages®
The Villages® 2202 KERSHAW RD, THE VILLAGES, FL, 32162, The Villages, FL 32162
$409,999

3 beds

|

2 baths

|

1,927 sq ft

|

House

2202 KERSHAW RD, THE VILLAGES, FL, 32162
Community: The Villages®
Latitude Margaritaville 1082 CASTAWAY CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$565,000

2 beds

|

2 baths

|

1,684 sq ft

|

House

1082 CASTAWAY CT, DAYTONA BEACH, FL, 321...
Stonecrest 17728 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$399,000

3 beds

|

3 baths

|

1,658 sq ft

|

House

17728 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
New Pelican Bay Daytona Beach 320 BOB WHITE CT 3200, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$235,000

2 beds

|

2 baths

|

1,469 sq ft

|

Condo

320 BOB WHITE CT 3200, DAYTONA BEACH, FL...
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® 3202 CONDREY CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$575,000

3 beds

|

2 baths

|

2,091 sq ft

|

House

3202 CONDREY CT, THE VILLAGES, FL, 32163
Community: The Villages®
Solivita 531 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$479,000

3 beds

|

3 baths

|

2,307 sq ft

|

House

531 VILLA PARK RD, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 2725 HALSEY TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$669,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

2725 HALSEY TER, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 4157 TIEDEMANN LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163
$379,000

3 beds

|

2 baths

|

1,569 sq ft

|

House

4157 TIEDEMANN LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Solivita 446 TREVISO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$524,900

3 beds

|

3 baths

|

2,235 sq ft

|

House

446 TREVISO DR, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Carillon Lakes 3913 SERENADE LN # 4, LAKELAND, FL, 3381..., Lakeland, FL 33811
$314,500

2 beds

|

2 baths

|

1,722 sq ft

|

Condo

3913 SERENADE LN # 4, LAKELAND, FL, 3381...
Community: Carillon Lakes
Lake James 7991 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$464,500

3 beds

|

2 baths

|

1,890 sq ft

|

House

7991 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Sun City Center 2114 WORTHINGTON GREENS DR, SUN CITY CEN..., Sun City Center, FL 33573
$349,000

2 beds

|

2 baths

|

2,102 sq ft

|

House

2114 WORTHINGTON GREENS DR, SUN CITY CEN...
Community: Sun City Center
The Villages® 4416 HOMAN LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$359,000

3 beds

|

2 baths

|

1,419 sq ft

|

House

4416 HOMAN LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1717 LILLY LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$259,000

2 beds

|

2 baths

|

1,856 sq ft

|

Manufactured Home

1717 LILLY LN, LADY LAKE, FL, 32159
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.
VillageWalk at Lake Nona 8639 LOWER VILLAGEWALK CIR, ORLANDO, FL,..., Orlando, FL 32827
$469,000

3 beds

|

3 baths

|

1,830 sq ft

|

Townhouse

8639 LOWER VILLAGEWALK CIR, ORLANDO, FL,...
Summit Greens 793 SUMMIT GREENS BLVD, CLERMONT, FL, 34..., Clermont, FL 34711
$385,000

2 beds

|

2 baths

|

1,731 sq ft

|

House

793 SUMMIT GREENS BLVD, CLERMONT, FL, 34...
Community: Summit Greens
Marion Landing 14930 SW 66TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$309,900

4 beds

|

2 baths

|

1,751 sq ft

|

House

14930 SW 66TH AVENUE RD, OCALA, FL, 3447...
Community: Marion Landing
The Villages® 7781 SE 166TH SMALLWOOD PL, THE VILLAGES..., The Villages, FL 32162
$390,000

3 beds

|

2 baths

|

1,924 sq ft

|

House

7781 SE 166TH SMALLWOOD PL, THE VILLAGES...
Community: The Villages®
The Villages® 3243 MANSFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$289,900

2 beds

|

2 baths

|

1,156 sq ft

|

House

3243 MANSFIELD ST, 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
Venetian Bay 327 TOSCA ST, NEW SMYRNA BEACH, FL, 3216..., New Smyrna Beach, FL 32168
$499,000

4 beds

|

3 baths

|

3,181 sq ft

|

House

327 TOSCA ST, NEW SMYRNA BEACH, FL, 3216...
Community: Venetian Bay
Plantation at Leesburg 5089 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$279,900

3 beds

|

2 baths

|

1,706 sq ft

|

House

5089 EL DESTINO DR, LEESBURG, FL, 34748
Kings Ridge 3821 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$299,900

2 beds

|

2 baths

|

1,447 sq ft

|

House

3821 DOUNE WAY, CLERMONT, FL, 34711
Community: Kings Ridge
Kings Ridge 3725 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711
$265,000

2 beds

|

2 baths

|

1,338 sq ft

|

House

3725 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
New The Villages® 2041 ROYAL ELM RD, THE VILLAGES, FL, 321..., The Villages, FL 32162
$399,000

3 beds

|

2 baths

|

1,551 sq ft

|

House

2041 ROYAL ELM RD, 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.
Pennbrooke Fairways 313 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$189,000

2 beds

|

2 baths

|

1,402 sq ft

|

Manufactured Home

313 WESTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Marion Landing 8668 SW 67TH CT, OCALA, FL, 34476, Ocala, FL 34476
$190,000

3 beds

|

2 baths

|

1,296 sq ft

|

Manufactured Home

8668 SW 67TH CT, OCALA, FL, 34476
Community: Marion Landing
Plantation at Leesburg 25523 MAUREPAS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$419,800

3 beds

|

3 baths

|

2,675 sq ft

|

House

25523 MAUREPAS LN, LEESBURG, FL, 34748
On Top of the World 8896 SW 90TH ST B, OCALA, FL, 34481, Ocala, FL 34481
$169,000

2 beds

|

2 baths

|

1,377 sq ft

|

House

8896 SW 90TH ST B, OCALA, FL, 34481
Community: On Top of the World
The Villages® 618 JUANITA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$376,500

3 beds

|

2 baths

|

1,418 sq ft

|

House

618 JUANITA CT, THE VILLAGES, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1607 DORAL CIR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$229,000

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

1607 DORAL CIR, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 934 ORCHID ST, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$339,900

3 beds

|

2 baths

|

1,495 sq ft

|

House

934 ORCHID ST, LADY LAKE, FL, 32159
Community: The Villages®
Spruce Creek Country Club 9343 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$469,000

3 beds

|

3 baths

|

2,324 sq ft

|

House

9343 SE 124TH PL, SUMMERFIELD, FL, 34491
The Villages® 518 ALCAZAR CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$269,000

2 beds

|

2 baths

|

1,383 sq ft

|

House

518 ALCAZAR CT, THE VILLAGES, FL, 32159
Community: The Villages®
On Top of the World 10071 SW 90TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$220,000

2 beds

|

2 baths

|

1,504 sq ft

|

House

10071 SW 90TH LOOP, OCALA, FL, 34481
Community: On Top of the World

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3,573 homes near Winter Garden
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