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

3,573 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
$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
$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.
3.8 rating (6 reviews) Trilogy® Orlando
$300Ks - $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 - $900Ks
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
$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
Sun City Center 607 MANCHESTER WOODS DR # 84, SUN CITY C..., Sun City Center, FL 33573
$203,000

2 beds

|

2 baths

|

1,444 sq ft

|

Condo

607 MANCHESTER WOODS DR # 84, SUN CITY C...
Community: Sun City Center
Venetian Bay 2820 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$529,000

3 beds

|

3 baths

|

2,203 sq ft

|

Townhouse

2820 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
SummerGlen 16405 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$279,870

3 beds

|

2 baths

|

1,676 sq ft

|

House

16405 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Valencia Lakes 4943 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$420,000

2 beds

|

2 baths

|

2,061 sq ft

|

House

4943 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Cresswind at Victoria Gardens 1653 VICTORIA GARDENS DR, DELAND, FL, 32..., Deland, FL 32724
$419,900

2 beds

|

2 baths

|

1,928 sq ft

|

House

1653 VICTORIA GARDENS DR, DELAND, FL, 32...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sullivan Ranch 30743 LIPIZZAN TER, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$324,500

3 beds

|

2 baths

|

1,663 sq ft

|

Villa

30743 LIPIZZAN TER, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
The Villages® 1802 PETUNIA LN, THE VILLAGES, FL, 32159, The Villages, FL 32159
$250,000

2 beds

|

2 baths

|

1,434 sq ft

|

Manufactured Home

1802 PETUNIA LN, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1827 KYRLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$432,000

3 beds

|

2 baths

|

1,887 sq ft

|

House

1827 KYRLE TER, THE VILLAGES, FL, 32162
Community: The Villages®
Gatherings of Lake Nona 7573 LAUREATE BLVD UNIT 1301, ORLANDO, F..., Orlando, FL 32827
$299,999

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

7573 LAUREATE BLVD UNIT 1301, ORLANDO, F...
On Top of the World 9880 SW 88TH TER B, OCALA, FL, 34481, Ocala, FL 34481
$255,000

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

9880 SW 88TH TER B, 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.
Valencia Lakes 15731 CRYSTAL WATERS DR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$400,000

3 beds

|

2 baths

|

1,986 sq ft

|

House

15731 CRYSTAL WATERS DR, WIMAUMA, FL, 33...
Community: Valencia Lakes
Valencia Lakes 16233 AMETHYST KEY DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$265,000

2 beds

|

2 baths

|

1,317 sq ft

|

Villa

16233 AMETHYST KEY DR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
Valencia Lakes 4821 GRAND BANKS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$525,000

3 beds

|

3 baths

|

2,268 sq ft

|

House

4821 GRAND BANKS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Valencia Lakes 16106 CEDAR KEY DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$549,000

4 beds

|

3 baths

|

2,467 sq ft

|

House

16106 CEDAR KEY DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Stonecrest 17652 SE 120TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$439,900

3 beds

|

2 baths

|

2,067 sq ft

|

House

17652 SE 120TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 6677 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$205,000

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6677 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Spruce Creek Country Club 9464 SE 132ND LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$227,500

1 beds

|

2 baths

|

1,020 sq ft

|

House

9464 SE 132ND LOOP, SUMMERFIELD, FL, 344...
On Top of the World 8457 SW 97TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$489,900

2 beds

|

2 baths

|

2,097 sq ft

|

House

8457 SW 97TH CIR, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek Country Club 13729 SE 89TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$275,900

3 beds

|

2 baths

|

1,760 sq ft

|

House

13729 SE 89TH AVE, SUMMERFIELD, FL, 3449...
Sun City Center 2327 PLATINUM DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$569,000

3 beds

|

2 baths

|

2,202 sq ft

|

House

2327 PLATINUM DR, SUN CITY CENTER, FL, 3...
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.
Venetian Bay 569 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$369,900

2 beds

|

2 baths

|

1,272 sq ft

|

House

569 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Breakaway Trails 6 BLACK PINE WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$729,000

4 beds

|

4 baths

|

3,289 sq ft

|

House

6 BLACK PINE WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
Solivita 159 OLYMPUS WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$405,000

3 beds

|

2 baths

|

1,730 sq ft

|

House

159 OLYMPUS WAY, KISSIMMEE, FL, 34759
Community: Solivita
Latitude Margaritaville 182 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$685,699

3 beds

|

3 baths

|

2,303 sq ft

|

House

182 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Latitude Margaritaville 306 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$475,000

2 beds

|

2 baths

|

1,509 sq ft

|

Townhouse

306 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek South 10783 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$214,500

2 beds

|

2 baths

|

1,144 sq ft

|

House

10783 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Colonnades 4846 COLONNADES CLUB BLVD, LAKELAND, FL,..., Lakeland, FL 33811
$257,000

2 beds

|

2 baths

|

1,534 sq ft

|

House

4846 COLONNADES CLUB BLVD, LAKELAND, FL,...
Community: Colonnades
The Villages® 932 MEDIRA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$419,500

2 beds

|

2 baths

|

1,732 sq ft

|

Villa

932 MEDIRA DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3432 FAIRFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,477 sq ft

|

House

3432 FAIRFIELD ST, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 2544 ASHVILLE AVE, THE VILLAGES, FL, 321..., The Villages, FL 32162
$661,000

3 beds

|

2 baths

|

2,725 sq ft

|

House

2544 ASHVILLE AVE, THE VILLAGES, FL, 321...
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.
Ocala Preserve 3231 NW 52ND AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$278,990

2 beds

|

2 baths

|

1,562 sq ft

|

Halfplex

3231 NW 52ND AVENUE RD, OCALA, FL, 34482
Community: Ocala Preserve
Carlsberg Estates on Lake Suzanne 4182 CANNES AVE, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$275,000

3 beds

|

3 baths

|

1,744 sq ft

|

House

4182 CANNES AVE, LAKE WALES, FL, 33859
Ocala Preserve 5270 NW 33RD PL, OCALA, FL, 34482, Ocala, FL 34482
$264,990

2 beds

|

2 baths

|

1,320 sq ft

|

Halfplex

5270 NW 33RD PL, OCALA, FL, 34482
Community: Ocala Preserve
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
On Top of the World 9285 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481
$215,000

2 beds

|

2 baths

|

1,756 sq ft

|

House

9285 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
Solivita 2212 PORTRAIT ST, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$290,000

3 beds

|

3 baths

|

1,373 sq ft

|

Townhouse

2212 PORTRAIT ST, KISSIMMEE, FL, 34758
Community: Solivita
Sun City Center 2501 SAPPHIRE GREENS LN, SUN CITY CENTER..., Sun City Center, FL 33573
$340,000

2 beds

|

2 baths

|

1,493 sq ft

|

Condo

2501 SAPPHIRE GREENS LN, SUN CITY CENTER...
Community: Sun City Center
Lake Jovita Golf and Country Club 13216 LEGENDS TRL, DADE CITY, FL, 33525, Dade City, FL 33525
$749,900

5 beds

|

3 baths

|

3,265 sq ft

|

House

13216 LEGENDS TRL, DADE CITY, FL, 33525
The Villages® 17037 SE 76TH CREEKSIDE CIR, THE VILLAGE..., The Villages, FL 32162
$510,000

3 beds

|

2 baths

|

2,136 sq ft

|

House

17037 SE 76TH CREEKSIDE CIR, THE VILLAGE...
Community: The Villages®
Venetian Bay 3008 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$339,000

3 beds

|

3 baths

|

1,672 sq ft

|

Townhouse

3008 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay

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3,573 homes near Winter Garden
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