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

3,952 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 - $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 - $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
$200Ks - $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 - $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 - $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 - $600Ks
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 - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $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
$200Ks - $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 - $900Ks
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
$200Ks - $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 - $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
$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
$300Ks - $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 - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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 - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
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 - $800Ks
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 - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$400Ks - $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 - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Palm Cay 11214 SW 77TH CT, OCALA, FL, 34476, Ocala, FL 34476
$159,000

2 beds

|

1 baths

|

840 sq ft

|

House

11214 SW 77TH CT, OCALA, FL, 34476
Community: Palm Cay
Ocala Palms 2339 NW 55TH AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$249,900

3 beds

|

2 baths

|

1,514 sq ft

|

House

2339 NW 55TH AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
Lake James 7919 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$499,900

3 beds

|

2 baths

|

1,925 sq ft

|

House

7919 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Breakaway Trails 11 FOREST VIEW WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$649,000

4 beds

|

2 baths

|

3,104 sq ft

|

House

11 FOREST VIEW WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
Four Seasons at Orlando 2212 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$495,900

3 beds

|

2 baths

|

1,904 sq ft

|

House

2212 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 8740 SE 140TH PLACE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$225,000

2 beds

|

2 baths

|

1,361 sq ft

|

House

8740 SE 140TH PLACE RD, SUMMERFIELD, FL,...
Venetian Bay 2913 LINARI CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$1,150,000

4 beds

|

3 baths

|

2,624 sq ft

|

House

2913 LINARI CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Sun City Center 613 FORT DUQUESNA DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$455,000

2 beds

|

2 baths

|

2,031 sq ft

|

House

613 FORT DUQUESNA DR, SUN CITY CENTER, F...
Community: Sun City Center
The Villages® 16914 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162
$365,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

16914 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
Sandpiper Golf & Country Club 5879 SWALLOW DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$284,000

3 beds

|

2 baths

|

1,406 sq ft

|

House

5879 SWALLOW DR, LAKELAND, FL, 33809
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 9652 SW 84TH TER C, OCALA, FL, 34481, Ocala, FL 34481
$154,900

2 beds

|

2 baths

|

1,031 sq ft

|

Villa

9652 SW 84TH TER C, OCALA, FL, 34481
Community: On Top of the World
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
Del Webb Sunbridge 6501 CYRILS DR, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$450,000

3 beds

|

3 baths

|

1,738 sq ft

|

Townhouse

6501 CYRILS DR, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
SummerGlen 15825 SW 11TH COURT RD, OCALA, FL, 34473, Ocala, FL 34473
$303,000

3 beds

|

2 baths

|

1,869 sq ft

|

House

15825 SW 11TH COURT RD, OCALA, FL, 34473
Community: SummerGlen
Royal Highlands 4848 SAINT ANDREWS ARC, LEESBURG, FL, 34..., Leesburg, FL 34748
$290,000

3 beds

|

2 baths

|

1,544 sq ft

|

House

4848 SAINT ANDREWS ARC, LEESBURG, FL, 34...
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 9395 SW 97TH LN B, OCALA, FL, 34481, Ocala, FL 34481
$140,000

2 beds

|

2 baths

|

1,180 sq ft

|

Villa

9395 SW 97TH LN B, OCALA, FL, 34481
Community: On Top of the World
Pelican Bay Daytona Beach 100 BROWN PELICAN DR, DAYTONA BEACH, FL,..., Daytona Beach, FL 32119
$329,900

3 beds

|

3 baths

|

1,876 sq ft

|

Halfplex

100 BROWN PELICAN DR, DAYTONA BEACH, FL,...
The Villages® 882 TANGLEWOOD PL, THE VILLAGES, FL, 321..., The Villages, FL 32162
$384,500

3 beds

|

2 baths

|

1,602 sq ft

|

Villa

882 TANGLEWOOD PL, THE VILLAGES, FL, 321...
Community: The Villages®
Royal Highlands 20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$399,000

3 beds

|

3 baths

|

2,224 sq ft

|

House

20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Royal Highlands 21122 LIONHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$279,900

3 beds

|

2 baths

|

1,453 sq ft

|

House

21122 LIONHEART DR, 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.
Sun City Center 1031 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$357,500

2 beds

|

2 baths

|

1,908 sq ft

|

House

1031 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Highlands Ridge 3006 OAKHILL DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$359,900

2 beds

|

2 baths

|

2,192 sq ft

|

House

3006 OAKHILL DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Arlington Ridge 4581 SHENANDOAH RIVER TRL, LEESBURG, FL,..., Leesburg, FL 34748
$515,000

3 beds

|

2 baths

|

2,236 sq ft

|

House

4581 SHENANDOAH RIVER TRL, LEESBURG, FL,...
Community: Arlington Ridge
Arlington Ridge 3677 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$500,000

3 beds

|

2 baths

|

2,201 sq ft

|

House

3677 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
On Top of the World 9483 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481
$368,000

3 beds

|

2 baths

|

2,370 sq ft

|

House

9483 SW 90TH ST, 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
Sun City Center 1321 BLUEWATER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$249,000

2 beds

|

2 baths

|

1,756 sq ft

|

House

1321 BLUEWATER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Royal Harbor 5305 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778
$353,500

3 beds

|

2 baths

|

1,824 sq ft

|

House

5305 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
Del Webb Orlando 1036 SALAMANCA PL, DAVENPORT, FL, 33837, Davenport, FL 33837
$295,000

2 beds

|

2 baths

|

1,287 sq ft

|

House

1036 SALAMANCA PL, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Latitude Margaritaville 443 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$449,000

3 beds

|

2 baths

|

1,563 sq ft

|

House

443 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Pelican Bay Daytona Beach 133 WOOD IBIS CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119
$359,900

3 beds

|

2 baths

|

1,914 sq ft

|

House

133 WOOD IBIS CT, DAYTONA BEACH, FL, 321...
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.
Royal Highlands 4712 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,999

3 beds

|

2 baths

|

1,615 sq ft

|

House

4712 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
Quail Meadow 4945 NW 33RD LN, OCALA, FL, 34482, Ocala, FL 34482
$270,000

3 beds

|

2 baths

|

1,490 sq ft

|

House

4945 NW 33RD LN, OCALA, FL, 34482
Community: Quail Meadow
Legacy of Leesburg 5818 GREENBRIAR LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748
$399,900

3 beds

|

2 baths

|

2,255 sq ft

|

House

5818 GREENBRIAR LOOP, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
Ocala Palms 2550 NW 55TH AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$279,900

3 beds

|

2 baths

|

1,548 sq ft

|

House

2550 NW 55TH AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
SummerGlen 15213 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$250,000

3 beds

|

2 baths

|

1,869 sq ft

|

House

15213 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Highland Lakes 26823 FOREST HILLS ST, LEESBURG, FL, 347..., Leesburg, FL 34748
$274,900

2 beds

|

2 baths

|

1,380 sq ft

|

House

26823 FOREST HILLS ST, LEESBURG, FL, 347...
Community: Highland Lakes
Esplanade at Highland Ranch 2554 STARGRASS CIR, CLERMONT, FL, 34715, Clermont, FL 34715
$549,000

2 beds

|

2 baths

|

1,995 sq ft

|

House

2554 STARGRASS CIR, CLERMONT, FL, 34715
Spruce Creek North 10740 SW 62ND AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34476
$213,000

2 beds

|

2 baths

|

1,092 sq ft

|

House

10740 SW 62ND AVENUE RD, OCALA, FL, 3447...
Community: Spruce Creek North
Cresswind at Victoria Gardens 319 BELLINGRATH TER, DELAND, FL, 32724, Deland, FL 32724
$363,000

3 beds

|

2 baths

|

2,240 sq ft

|

House

319 BELLINGRATH TER, DELAND, FL, 32724
Royal Highlands 21926 KING ALFRED ST, LEESBURG, FL, 3474..., Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

1,784 sq ft

|

House

21926 KING ALFRED ST, LEESBURG, FL, 3474...
Community: Royal Highlands

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3,952 homes near Winter Garden
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