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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) 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
<$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
Venetian Bay 545 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$414,900

3 beds

|

2 baths

|

1,916 sq ft

|

House

545 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Venetian Bay 219 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$549,900

4 beds

|

3 baths

|

2,196 sq ft

|

House

219 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Venetian Bay 3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$395,000

2 beds

|

2 baths

|

1,003 sq ft

|

Townhouse

3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Harbor Hills Country Club 6145 SPINNAKER LOOP, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$649,900

4 beds

|

3 baths

|

3,294 sq ft

|

House

6145 SPINNAKER LOOP, LADY LAKE, FL, 3215...
Colonnades 4829 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$262,500

2 beds

|

2 baths

|

1,182 sq ft

|

House

4829 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pelican Bay Daytona Beach 149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$224,000

2 beds

|

2 baths

|

1,075 sq ft

|

House

149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3...
On Top of the World 10597 SW 90TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481
$336,000

2 beds

|

2 baths

|

1,651 sq ft

|

House

10597 SW 90TH STREET RD, OCALA, FL, 3448...
Community: On Top of the World
Marco Polo Village 5312 SW 109TH PLACE ROAD RD, OCALA, FL, ..., Ocala, FL 34476
$269,900

3 beds

|

2 baths

|

1,758 sq ft

|

House

5312 SW 109TH PLACE ROAD RD, OCALA, FL, ...
Community: Marco Polo Village
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
On Top of the World 9010 SW 89TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$519,000

3 beds

|

3 baths

|

2,811 sq ft

|

House

9010 SW 89TH LOOP, 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.
On Top of the World 9042 SW 88TH PL, OCALA, FL, 34481, Ocala, FL 34481
$599,000

3 beds

|

3 baths

|

2,815 sq ft

|

House

9042 SW 88TH PL, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 408 GLOUCESTER BLVD # 33, SUN CITY CENTE..., Sun City Center, FL 33573
$99,000

1 beds

|

2 baths

|

928 sq ft

|

Condo

408 GLOUCESTER BLVD # 33, SUN CITY CENTE...
Community: Sun City Center
Kings Ridge 2310 GRASMERE CIR, CLERMONT, FL, 34711, Clermont, FL 34711
$315,000

2 beds

|

2 baths

|

1,677 sq ft

|

House

2310 GRASMERE CIR, CLERMONT, FL, 34711
Community: Kings Ridge
Solivita 531 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$464,000

3 beds

|

3 baths

|

2,307 sq ft

|

House

531 VILLA PARK RD, KISSIMMEE, FL, 34759
Community: Solivita
Cresswind at Victoria Gardens 1385 LONGLEY PL, DELAND, FL, 32724, Deland, FL 32724
$379,900

3 beds

|

2 baths

|

1,658 sq ft

|

House

1385 LONGLEY PL, DELAND, FL, 32724
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1816 N PEBBLE BEACH BLVD, SUN CITY CENTE..., Sun City Center, FL 33573
$259,000

2 beds

|

2 baths

|

1,860 sq ft

|

Villa

1816 N PEBBLE BEACH BLVD, SUN CITY CENTE...
Community: Sun City Center
On Top of the World 8552 SW 92ND LN C, OCALA, FL, 34481, Ocala, FL 34481
$119,900

2 beds

|

2 baths

|

1,369 sq ft

|

Villa

8552 SW 92ND LN C, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9273 SW 91ST COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$364,900

2 beds

|

2 baths

|

2,311 sq ft

|

House

9273 SW 91ST COURT RD, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8658 SW 95TH LN B, OCALA, FL, 34481, Ocala, FL 34481
$179,900

2 beds

|

2 baths

|

1,179 sq ft

|

Villa

8658 SW 95TH LN B, OCALA, FL, 34481
Community: On Top of the World
SummerGlen 16026 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$274,654

3 beds

|

2 baths

|

1,800 sq ft

|

House

16026 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
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 8640 SW 83RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$305,000

3 beds

|

2 baths

|

1,906 sq ft

|

House

8640 SW 83RD LOOP, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8532 SW 93RD PL B, OCALA, FL, 34481, Ocala, FL 34481
$189,000

2 beds

|

2 baths

|

1,385 sq ft

|

Villa

8532 SW 93RD PL B, OCALA, FL, 34481
Community: On Top of the World
The Villages® 2317 WHISPER ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$229,000

1 beds

|

1 baths

|

991 sq ft

|

Villa

2317 WHISPER ST, THE VILLAGES, FL, 32162
Community: The Villages®
Harbor Hills Country Club 39634 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$474,900

3 beds

|

2 baths

|

2,579 sq ft

|

House

39634 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Ocala Palms 2399 NW 53RD AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$289,900

3 beds

|

2 baths

|

1,739 sq ft

|

House

2399 NW 53RD AVENUE RD, 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
Tampa Bay Golf and Country Club 29436 ZELLER AVE, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$229,900

2 beds

|

2 baths

|

1,124 sq ft

|

House

29436 ZELLER AVE, SAN ANTONIO, FL, 33576
Arlington Ridge 26917 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$260,000

2 beds

|

2 baths

|

1,251 sq ft

|

Villa

26917 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
The Villages® 1508 GIFFORD CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$410,000

3 beds

|

2 baths

|

1,554 sq ft

|

House

1508 GIFFORD CT, THE VILLAGES, FL, 32162
Community: The Villages®
Stone Creek 9673 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$285,000

2 beds

|

2 baths

|

1,447 sq ft

|

House

9673 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
Kings Ridge 4202 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711
$439,900

2 beds

|

2 baths

|

1,968 sq ft

|

House

4202 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings 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.
Sun City Center 1209 WILD FEATHER LN, SUN CITY CENTER, F..., Sun City Center, FL 33573
$234,900

2 beds

|

2 baths

|

1,860 sq ft

|

House

1209 WILD FEATHER LN, SUN CITY CENTER, F...
Community: Sun City Center
Vienna Square 1620 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$235,000

2 beds

|

2 baths

|

1,329 sq ft

|

Villa

1620 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
On Top of the World 8373 SW 82ND LOOP, OCALA, FL, 34481, Ocala, FL 34481
$320,000

3 beds

|

2 baths

|

2,048 sq ft

|

House

8373 SW 82ND LOOP, OCALA, FL, 34481
Community: On Top of the World
Marco Polo Village 10884 SW 53RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$314,900

3 beds

|

2 baths

|

2,026 sq ft

|

House

10884 SW 53RD CIR, OCALA, FL, 34476
Community: Marco Polo Village
Spruce Creek Preserve 13364 SW 111TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$174,900

2 beds

|

2 baths

|

1,382 sq ft

|

Villa

13364 SW 111TH CIR, DUNNELLON, FL, 34432
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 4378 NW 54TH TER, OCALA, FL, 34482, Ocala, FL 34482
$469,000

3 beds

|

3 baths

|

2,360 sq ft

|

House

4378 NW 54TH TER, OCALA, FL, 34482
Community: Ocala Preserve
Solivita 417 LAKE BUTLER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$324,900

3 beds

|

2 baths

|

2,728 sq ft

|

House

417 LAKE BUTLER DR, KISSIMMEE, FL, 34759
Community: Solivita
On Top of the World 7947 SW 80TH PLACE RD, OCALA, FL, 34476, Ocala, FL 34476
$234,900

3 beds

|

2 baths

|

2,032 sq ft

|

House

7947 SW 80TH PLACE RD, OCALA, FL, 34476
Community: On Top of the World
JB Ranch 9238 SW 60TH COURT RD, OCALA, FL, 34476, Ocala, FL 34476
$440,000

3 beds

|

3 baths

|

2,619 sq ft

|

House

9238 SW 60TH COURT RD, OCALA, FL, 34476
Community: JB Ranch
Cresswind DeLand 1235 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724
$599,990

3 beds

|

4 baths

|

2,496 sq ft

|

House

1235 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand

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3,648 homes near Winter Garden
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