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

3,584 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
<$100k - $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!
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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.
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) Trilogy® Orlando
$300Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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 - $900Ks
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
$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
Spruce Creek Preserve 11628 SW 140TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432
$229,000

2 beds

|

2 baths

|

1,536 sq ft

|

House

11628 SW 140TH LOOP, DUNNELLON, FL, 3443...
Spruce Creek Preserve 14272 SW 112TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$279,000

3 beds

|

2 baths

|

1,790 sq ft

|

House

14272 SW 112TH CIR, DUNNELLON, FL, 34432
Spruce Creek Preserve 13816 SW 112TH TER, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$240,000

2 beds

|

2 baths

|

1,672 sq ft

|

House

13816 SW 112TH TER, DUNNELLON, FL, 34432
Silver Lakes 2244 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$254,990

2 beds

|

2 baths

|

1,545 sq ft

|

House

2244 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
Spruce Creek Preserve 13675 SW 111TH AVE, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$229,000

2 beds

|

2 baths

|

1,382 sq ft

|

Villa

13675 SW 111TH AVE, DUNNELLON, FL, 34432
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Preserve 11536 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$214,000

2 beds

|

2 baths

|

1,122 sq ft

|

House

11536 SW 138TH LN, DUNNELLON, FL, 34432
Spruce Creek Preserve 11495 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$225,000

3 beds

|

2 baths

|

1,412 sq ft

|

House

11495 SW 138TH LN, DUNNELLON, FL, 34432
Venetian Bay 2904 PALMA LN, NEW SMYRNA BEACH, FL, 321..., New Smyrna Beach, FL 32168
$1,518,888

5 beds

|

4 baths

|

3,372 sq ft

|

House

2904 PALMA LN, NEW SMYRNA BEACH, FL, 321...
Community: Venetian Bay
Spruce Creek Preserve 14191 SW 115TH TER, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$259,000

2 beds

|

2 baths

|

1,687 sq ft

|

House

14191 SW 115TH TER, DUNNELLON, FL, 34432
Spruce Creek Preserve 11643 SW 137TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432
$225,000

2 beds

|

2 baths

|

1,322 sq ft

|

House

11643 SW 137TH LOOP, DUNNELLON, FL, 3443...
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 11518 SW 136TH PL, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$225,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

11518 SW 136TH PL, DUNNELLON, FL, 34432
Spruce Creek Preserve 15024 SW 112TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$295,000

3 beds

|

2 baths

|

1,835 sq ft

|

House

15024 SW 112TH CIR, DUNNELLON, FL, 34432
High Vista at Ridgewood Lakes 100 MOSS LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,000

3 beds

|

2 baths

|

2,051 sq ft

|

House

100 MOSS LN, DAVENPORT, FL, 33837
The Villages® 3083 YODER DR, THE VILLAGES, FL, 32163, The Villages, FL 32163
$929,500

3 beds

|

2 baths

|

2,478 sq ft

|

House

3083 YODER DR, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 2991 SAINT THOMAS LN, THE VILLAGES, FL, ..., The Villages, FL 32162
$449,000

3 beds

|

2 baths

|

1,777 sq ft

|

House

2991 SAINT THOMAS LN, THE VILLAGES, FL, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Palm 1636 ARECA PALM DR, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$319,900

2 beds

|

2 baths

|

1,331 sq ft

|

Townhouse

1636 ARECA PALM DR, PORT ORANGE, FL, 321...
Community: Royal Palm
Sun City Center 505 FOXGLOVE CIR B, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$185,000

2 beds

|

2 baths

|

1,245 sq ft

|

Halfplex

505 FOXGLOVE CIR B, SUN CITY CENTER, FL,...
Community: Sun City Center
Trilogy® Orlando 341 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$429,900

2 beds

|

2 baths

|

1,612 sq ft

|

House

341 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Lake James 7771 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$399,000

2 beds

|

2 baths

|

1,925 sq ft

|

House

7771 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Valencia Lakes 4918 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$525,000

3 beds

|

3 baths

|

2,461 sq ft

|

House

4918 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
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.
Venetian Bay 3604 ROMEA CIR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$385,000

3 beds

|

2 baths

|

1,870 sq ft

|

Townhouse

3604 ROMEA CIR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Sun City Center 2016 EAST VIEW DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$399,900

2 beds

|

2 baths

|

2,213 sq ft

|

House

2016 EAST VIEW DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Del Webb Orlando 763 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$300,000

2 beds

|

2 baths

|

1,348 sq ft

|

House

763 ASTURIAS RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
On Top of the World 9729 SW 97TH ST, OCALA, FL, 34481, Ocala, FL 34481
$229,000

2 beds

|

2 baths

|

1,230 sq ft

|

House

9729 SW 97TH ST, OCALA, FL, 34481
Community: On Top of the World
High Vista at Ridgewood Lakes 145 LEWIS DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$314,000

2 beds

|

2 baths

|

1,723 sq ft

|

House

145 LEWIS DR, DAVENPORT, FL, 33837
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Encore at Fishhawk Ranch 6113 PLOVER MEADOW ST, LITHIA, FL, 33547, Lithia, FL 33547
$484,000

2 beds

|

2 baths

|

1,916 sq ft

|

House

6113 PLOVER MEADOW ST, LITHIA, FL, 33547
Valencia Lakes 4947 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$449,000

2 beds

|

2 baths

|

2,061 sq ft

|

House

4947 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Sun City Center 1809 HAVERFORD AVE, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$275,000

2 beds

|

2 baths

|

1,402 sq ft

|

House

1809 HAVERFORD AVE, SUN CITY CENTER, FL,...
Community: Sun City Center
On Top of the World 9235 SW 96TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$258,500

2 beds

|

2 baths

|

1,664 sq ft

|

House

9235 SW 96TH COURT RD, OCALA, FL, 34481
Community: On Top of the World
Royal Highlands 21821 KING JOHN ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$250,250

3 beds

|

2 baths

|

1,694 sq ft

|

House

21821 KING JOHN ST, LEESBURG, FL, 34748
Community: Royal Highlands
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.
Oak Run 11058 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$199,000

2 beds

|

2 baths

|

1,550 sq ft

|

House

11058 SW 69TH CIR, OCALA, FL, 34476
Community: Oak Run
The Villages® 1135 BURKE CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$490,000

3 beds

|

2 baths

|

1,966 sq ft

|

House

1135 BURKE CT, THE VILLAGES, FL, 32162
Community: The Villages®
Solivita 1260 BONITA CANYON DR, POINCIANA, FL, 34..., Poinciana, FL 34759
$379,000

2 beds

|

3 baths

|

2,053 sq ft

|

House

1260 BONITA CANYON DR, POINCIANA, FL, 34...
Community: Solivita
The Villages® 925 BEECHWOOD AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$225,000

2 beds

|

2 baths

|

1,568 sq ft

|

Manufactured Home

925 BEECHWOOD AVE, LADY LAKE, FL, 32159
Community: The Villages®
Colonnades 4904 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$240,000

2 beds

|

2 baths

|

1,523 sq ft

|

House

4904 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pennbrooke Fairways 32676 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$270,000

3 beds

|

2 baths

|

1,709 sq ft

|

House

32676 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Marion Landing 6740 SW 84TH ST, OCALA, FL, 34476, Ocala, FL 34476
$189,000

3 beds

|

2 baths

|

1,187 sq ft

|

Manufactured Home

6740 SW 84TH ST, OCALA, FL, 34476
Community: Marion Landing
Solivita 314 DAVINCI PASS, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$309,999

2 beds

|

2 baths

|

1,467 sq ft

|

House

314 DAVINCI PASS, KISSIMMEE, FL, 34759
Community: Solivita
Legacy of Leesburg 5710 CELEBRATION WAY, LEESBURG, FL, 3474..., Leesburg, FL 34748
$359,900

3 beds

|

2 baths

|

2,004 sq ft

|

House

5710 CELEBRATION WAY, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
Lake Ashton 4128 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$275,000

3 beds

|

2 baths

|

1,503 sq ft

|

House

4128 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton

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3,584 homes near Winter Garden
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