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Winter Garden, FL 55+ active adult communities & homes for sale - Page 73

3,517 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 - $700Ks
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 - $900Ks
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
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 (2 reviews) Plantation at Leesburg
$100Ks - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
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
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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
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 - $600Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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 (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
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
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Questions? Call us: (689) 407-5757
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
4 rating (7 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
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 (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
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Questions? Call us: (689) 407-5757
5 rating (5 reviews) SummerGlen
$100Ks - $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
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.
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
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
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
Pelican Bay Daytona Beach 133 BLUE HERON DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$199,000

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

133 BLUE HERON DR C, DAYTONA BEACH, FL, ...
Stone Creek 8335 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$353,690

3 beds

|

2 baths

|

1,662 sq ft

|

House

8335 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 9539 SW 71ST LOOP, OCALA, FL, 34481, Ocala, FL 34481
$459,000

3 beds

|

2 baths

|

2,413 sq ft

|

House

9539 SW 71ST LOOP, OCALA, FL, 34481
Community: Stone Creek
New On Top of the World 10061 SW 89TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$379,900

2 beds

|

2 baths

|

2,082 sq ft

|

House

10061 SW 89TH LOOP, OCALA, FL, 34481
Community: On Top of the World
New Solivita 2316 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$308,200

2 beds

|

2 baths

|

1,539 sq ft

|

House

2316 PALM TREE 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
Solivita 2376 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$310,000

2 beds

|

2 baths

|

1,539 sq ft

|

Halfplex

2376 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
New Stone Creek 5394 SW 86TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$357,580

2 beds

|

2 baths

|

1,655 sq ft

|

House

5394 SW 86TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 5967 SW 82ND TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$520,460

2 beds

|

3 baths

|

2,269 sq ft

|

House

5967 SW 82ND TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
New Oak Run 6257 SW 84TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$568,040

3 beds

|

4 baths

|

2,808 sq ft

|

House

6257 SW 84TH AVE, OCALA, FL, 34481
Community: Oak Run
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.
Stone Creek 9685 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$249,500

2 beds

|

2 baths

|

1,305 sq ft

|

House

9685 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
Sun City Center 1811 BEDFORD LN, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$123,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

1811 BEDFORD LN, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Sun City Center 1806 WOLF LAUREL DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$379,000

2 beds

|

2 baths

|

1,890 sq ft

|

House

1806 WOLF LAUREL DR, SUN CITY CENTER, FL...
Community: Sun City Center
New Stone Creek 8447 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$446,910

2 beds

|

2 baths

|

1,889 sq ft

|

House

8447 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Palms 2238 NW 50TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$214,900

2 beds

|

2 baths

|

1,395 sq ft

|

House

2238 NW 50TH AVE, OCALA, FL, 34482
Community: Ocala Palms
Spruce Creek Preserve 11411 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$264,000

3 beds

|

2 baths

|

1,974 sq ft

|

House

11411 SW 138TH LN, DUNNELLON, FL, 34432
El Dorado 3555 SW 24TH AVENUE RD, OCALA, FL, 34471, Ocala, FL 34471
$525,000

4 beds

|

3 baths

|

3,304 sq ft

|

House

3555 SW 24TH AVENUE RD, OCALA, FL, 34471
Community: El Dorado
Valencia Ridge 3923 CORSICA PL, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$917,900

3 beds

|

4 baths

|

2,788 sq ft

|

House

3923 CORSICA PL, WESLEY CHAPEL, FL, 3354...
Community: Valencia 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.
Cherrywood 10031 SW 62ND CIR, OCALA, FL, 34476, Ocala, FL 34476
$200,000

3 beds

|

2 baths

|

1,855 sq ft

|

House

10031 SW 62ND CIR, OCALA, FL, 34476
Community: Cherrywood
The Villages® 3072 BERWYN WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$339,900

2 beds

|

2 baths

|

1,392 sq ft

|

House

3072 BERWYN WAY, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1705 KILEY CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$169,000

3 beds

|

2 baths

|

1,292 sq ft

|

Manufactured Home

1705 KILEY CT, THE VILLAGES, FL, 32159
Community: The Villages®
Stonecrest 12115 SE 175TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$524,900

3 beds

|

3 baths

|

2,074 sq ft

|

House

12115 SE 175TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Palm 5408 DAYLILLY ST, PORT ORANGE, FL, 32128, Port Orange, FL 32128
$374,929

4 beds

|

2 baths

|

1,871 sq ft

|

House

5408 DAYLILLY ST, PORT ORANGE, FL, 32128
Community: Royal Palm
Summer Trees 109 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$270,809

2 beds

|

2 baths

|

1,403 sq ft

|

House

109 UNDERBRUSH TRL, PORT ORANGE, FL, 321...
Community: Summer Trees
The Villages® 612 DOMINGUEZ DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$265,000

2 beds

|

2 baths

|

1,214 sq ft

|

Villa

612 DOMINGUEZ DR, THE VILLAGES, FL, 3215...
Community: The Villages®
Sun City Center 615 TREMONT GREENS LN, SUN CITY CENTER, ..., Sun City Center, FL 33573
$174,900

2 beds

|

2 baths

|

1,137 sq ft

|

Condo

615 TREMONT GREENS LN, SUN CITY CENTER, ...
Community: Sun City Center
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® 3338 QUEENSWAY TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$524,900

3 beds

|

2 baths

|

2,013 sq ft

|

House

3338 QUEENSWAY TER, THE VILLAGES, FL, 32...
Community: The Villages®
Stonecrest 16863 SE 110TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$359,000

3 beds

|

2 baths

|

1,687 sq ft

|

House

16863 SE 110TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
Spruce Creek Country Club 13751 SE 88TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$265,000

2 beds

|

2 baths

|

1,364 sq ft

|

House

13751 SE 88TH CT, SUMMERFIELD, FL, 34491
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® 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®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3229 KILLINGTON LOOP, THE VILLAGES, FL, ..., The Villages, FL 32163
$535,000

3 beds

|

3 baths

|

2,072 sq ft

|

House

3229 KILLINGTON LOOP, THE VILLAGES, FL, ...
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® 1945 RIEGER RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$625,000

3 beds

|

2 baths

|

2,036 sq ft

|

House

1945 RIEGER RD, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1318 GUERRA AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$349,900

3 beds

|

2 baths

|

1,561 sq ft

|

House

1318 GUERRA AVE, THE VILLAGES, 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.
Lake Jovita Golf and Country Club 13049 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525
$729,900

4 beds

|

4 baths

|

3,566 sq ft

|

House

13049 THOROUGHBRED DR, DADE CITY, FL, 33...
The Country Club of Mount Dora 2250 CHASE CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$437,000

3 beds

|

2 baths

|

1,716 sq ft

|

House

2250 CHASE CT, MOUNT DORA, FL, 32757
On Top of the World 7765 SW 80TH PLACE RD, OCALA, FL, 34476, Ocala, FL 34476
$314,900

2 beds

|

2 baths

|

1,737 sq ft

|

House

7765 SW 80TH PLACE RD, OCALA, FL, 34476
Community: On Top of the World
On Top of the World 8233 SW 93RD TER, OCALA, FL, 34481, Ocala, FL 34481
$493,250

2 beds

|

3 baths

|

2,815 sq ft

|

House

8233 SW 93RD TER, OCALA, FL, 34481
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Colonnades 4908 DAWNVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$239,200

2 beds

|

2 baths

|

1,338 sq ft

|

House

4908 DAWNVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
Sun City Center 2315 NEW ORCHARD CT 40, SUN CITY CENTER,..., Sun City Center, FL 33573
$189,900

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2315 NEW ORCHARD CT 40, SUN CITY CENTER,...
Community: Sun City Center

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