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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
Trilogy® Orlando 125 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$397,500

3 beds

|

2 baths

|

1,680 sq ft

|

House

125 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Oak Run 7251 SW 115TH PL, OCALA, FL, 34476, Ocala, FL 34476
$185,000

2 beds

|

2 baths

|

1,537 sq ft

|

House

7251 SW 115TH PL, OCALA, FL, 34476
Community: Oak Run
Stone Creek 6816 SW 95TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$464,999

2 beds

|

2 baths

|

1,969 sq ft

|

House

6816 SW 95TH CIR, OCALA, FL, 34481
Community: Stone Creek
Latitude Margaritaville 208 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$462,800

2 beds

|

2 baths

|

1,482 sq ft

|

House

208 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Sun City Center 721 ELKHORN RD, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$290,000

3 beds

|

2 baths

|

2,522 sq ft

|

House

721 ELKHORN RD, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lakes of Mount Dora 8677 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$474,990

2 beds

|

3 baths

|

2,012 sq ft

|

House

8677 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
Summit Greens 2817 FALCON RDG, CLERMONT, FL, 34711, Clermont, FL 34711
$429,000

3 beds

|

3 baths

|

2,300 sq ft

|

House

2817 FALCON RDG, CLERMONT, FL, 34711
Community: Summit Greens
Lake Jovita Golf and Country Club 12735 EASTPOINTE DR, DADE CITY, FL, 3352..., Dade City, FL 33525
$455,000

4 beds

|

2 baths

|

2,057 sq ft

|

House

12735 EASTPOINTE DR, DADE CITY, FL, 3352...
Solivita 271 INDIAN WELLS AVE, POINCIANA, FL, 347..., Poinciana, FL 34759
$435,000

2 beds

|

2 baths

|

2,471 sq ft

|

House

271 INDIAN WELLS AVE, POINCIANA, FL, 347...
Community: Solivita
Solivita 432 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$268,000

2 beds

|

2 baths

|

1,507 sq ft

|

House

432 GRAND CANAL DR, POINCIANA, FL, 34759
Community: Solivita
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 Preserve 11353 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$239,900

2 beds

|

2 baths

|

1,664 sq ft

|

House

11353 SW 138TH LN, DUNNELLON, FL, 34432
Oak Run 11410 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$289,999

2 beds

|

2 baths

|

1,583 sq ft

|

House

11410 SW 69TH CIR, OCALA, FL, 34476
Community: Oak Run
Archers Mill 3349 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$484,990

5 beds

|

5 baths

|

3,345 sq ft

|

House

3349 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
SummerGlen 1732 SW 157TH PLACE RD, OCALA, FL, 34473, Ocala, FL 34473
$397,500

3 beds

|

2 baths

|

2,256 sq ft

|

House

1732 SW 157TH PLACE RD, OCALA, FL, 34473
Community: SummerGlen
Cresswind at Victoria Gardens 1011 CLAYMONT BLVD, DELAND, FL, 32724, Deland, FL 32724
$347,047

3 beds

|

2 baths

|

1,541 sq ft

|

House

1011 CLAYMONT BLVD, DELAND, FL, 32724
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Oakview 1518 OAKVIEW CIR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880
$226,650

2 beds

|

2 baths

|

1,438 sq ft

|

House

1518 OAKVIEW CIR, WINTER HAVEN, FL, 3388...
Community: Oakview
On Top of the World 8872 SW 92ND PL F, OCALA, FL, 34481, Ocala, FL 34481
$154,000

2 beds

|

2 baths

|

1,394 sq ft

|

Villa

8872 SW 92ND PL F, OCALA, FL, 34481
Community: On Top of the World
Latitude Margaritaville 148 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$429,900

2 beds

|

2 baths

|

1,378 sq ft

|

House

148 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Tampa Bay Golf and Country Club 29241 KAPALUA WAY, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$300,000

2 beds

|

2 baths

|

1,861 sq ft

|

House

29241 KAPALUA WAY, SAN ANTONIO, FL, 3357...
Ocala Preserve 4473 NW 53RD AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$440,990

2 beds

|

3 baths

|

2,059 sq ft

|

House

4473 NW 53RD AVENUE RD, OCALA, FL, 34482
Community: Ocala Preserve
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.
Ocala Preserve 4443 NW 53RD AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$349,990

2 beds

|

2 baths

|

1,631 sq ft

|

House

4443 NW 53RD AVENUE RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4516 NW 54TH TER, OCALA, FL, 34482, Ocala, FL 34482
$450,990

2 beds

|

3 baths

|

2,060 sq ft

|

House

4516 NW 54TH TER, OCALA, FL, 34482
Community: Ocala Preserve
The Villages® 2866 JUDAH ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$314,000

2 beds

|

2 baths

|

1,257 sq ft

|

House

2866 JUDAH ST, THE VILLAGES, FL, 32163
Community: The Villages®
Spruce Creek North 10780 SW 62ND AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34476
$179,900

2 beds

|

2 baths

|

960 sq ft

|

House

10780 SW 62ND AVENUE RD, OCALA, FL, 3447...
Community: Spruce Creek North
The Villages® 3010 FRITILLARY TER, THE VILLAGES, FL, 3..., The Villages, FL 32163
$239,900

2 beds

|

1 baths

|

1,067 sq ft

|

Villa

3010 FRITILLARY TER, THE VILLAGES, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1675 WESTMINSTER CT, THE VILLAGES, FL, 3..., The Villages, FL 32162
$384,247

3 beds

|

2 baths

|

1,587 sq ft

|

House

1675 WESTMINSTER CT, THE VILLAGES, FL, 3...
Community: The Villages®
Sun City Center 214 GLOUCESTER BLVD, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$149,900

2 beds

|

2 baths

|

984 sq ft

|

Condo

214 GLOUCESTER BLVD, SUN CITY CENTER, FL...
Community: Sun City Center
Sun City Center 1503 LAUGHTON PL 206, SUN CITY CENTER, F..., Sun City Center, FL 33573
$234,000

2 beds

|

2 baths

|

1,751 sq ft

|

Condo

1503 LAUGHTON PL 206, SUN CITY CENTER, F...
Community: Sun City Center
Sun City Center 2339 GLENMORE CIR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$154,900

2 beds

|

2 baths

|

960 sq ft

|

Condo

2339 GLENMORE CIR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Sun City Center 675 MASTERPIECE DR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$319,900

3 beds

|

3 baths

|

2,171 sq ft

|

Condo

675 MASTERPIECE DR, SUN CITY CENTER, FL,...
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.
Sun City Center 2421 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$194,900

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

2421 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Sun City Center 2411 NANTUCKET HARBOR LOOP, SUN CITY CEN..., Sun City Center, FL 33573
$174,900

2 beds

|

2 baths

|

1,265 sq ft

|

Condo

2411 NANTUCKET HARBOR LOOP, SUN CITY CEN...
Community: Sun City Center
Sun City Center 1908 CANTERBURY LN 25, SUN CITY CENTER, ..., Sun City Center, FL 33573
$122,900

2 beds

|

2 baths

|

984 sq ft

|

Condo

1908 CANTERBURY LN 25, SUN CITY CENTER, ...
Community: Sun City Center
Valencia Lakes 15820 AURORA LAKE CIR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$279,900

2 beds

|

2 baths

|

1,496 sq ft

|

Villa

15820 AURORA LAKE CIR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
Sun City Center 2467 NANTUCKET HARBOR LOOP 122, SUN CITY..., Sun City Center, FL 33573
$234,000

2 beds

|

2 baths

|

1,313 sq ft

|

Condo

2467 NANTUCKET HARBOR LOOP 122, SUN CITY...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Valencia Lakes 15837 AURORA LAKE CIR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$314,900

2 beds

|

2 baths

|

1,747 sq ft

|

Villa

15837 AURORA LAKE CIR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
Sun City Center 201 KINGS BLVD 19, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$99,900

1 beds

|

2 baths

|

800 sq ft

|

Condo

201 KINGS BLVD 19, SUN CITY CENTER, FL, ...
Community: Sun City Center
Sun City Center 1011 OTTER MILL WAY, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$289,900

2 beds

|

3 baths

|

2,105 sq ft

|

Condo

1011 OTTER MILL WAY, SUN CITY CENTER, FL...
Community: Sun City Center
Sun City Center 2315 NEW ORCHARD CT 40, SUN CITY CENTER,..., Sun City Center, FL 33573
$194,900

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2315 NEW ORCHARD CT 40, SUN CITY CENTER,...
Community: Sun City Center
Sun City Center 2529 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$199,900

2 beds

|

2 baths

|

1,359 sq ft

|

Condo

2529 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center

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3,648 homes near Winter Garden
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