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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!
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 - $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 2315 NEW ORCHARD CT 40, SUN CITY CENTER,..., Sun City Center, FL 33573
$199,900

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2315 NEW ORCHARD CT 40, SUN CITY CENTER,...
Community: Sun City Center
Latitude Margaritaville 167 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$479,900

3 beds

|

2 baths

|

1,848 sq ft

|

House

167 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Latitude Margaritaville 597 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$539,900

3 beds

|

2 baths

|

1,862 sq ft

|

House

597 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
JB Ranch 4706 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$297,990

3 beds

|

2 baths

|

1,672 sq ft

|

House

4706 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
Ocala Preserve 4859 NW 35TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$369,000

2 beds

|

2 baths

|

1,666 sq ft

|

House

4859 NW 35TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 5589 NW 40TH LOOP, OCALA, FL, 34482, Ocala, FL 34482
$399,900

2 beds

|

2 baths

|

1,666 sq ft

|

House

5589 NW 40TH LOOP, OCALA, FL, 34482
Community: Ocala Preserve
Marion Landing 6848 SW 84TH PL, OCALA, FL, 34476, Ocala, FL 34476
$155,000

2 beds

|

2 baths

|

1,012 sq ft

|

Manufactured Home

6848 SW 84TH PL, OCALA, FL, 34476
Community: Marion Landing
Tampa Bay Golf and Country Club 11027 DORMIE DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$325,000

2 beds

|

2 baths

|

1,700 sq ft

|

House

11027 DORMIE DR, SAN ANTONIO, FL, 33576
El Dorado 3555 SW 24TH AVENUE RD, OCALA, FL, 34471, Ocala, FL 34471
$567,000

4 beds

|

3 baths

|

3,304 sq ft

|

House

3555 SW 24TH AVENUE RD, OCALA, FL, 34471
Community: El Dorado
Heritage Hills 3685 CORSICA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$415,000

3 beds

|

2 baths

|

1,836 sq ft

|

House

3685 CORSICA LN, CLERMONT, FL, 34711
Community: Heritage Hills
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.
Solivita 187 TALL PINES PASS, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$299,500

2 beds

|

2 baths

|

2,031 sq ft

|

House

187 TALL PINES PASS, KISSIMMEE, FL, 3475...
Community: Solivita
Solivita 634 VIA CORSO CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$430,000

2 beds

|

2 baths

|

1,705 sq ft

|

House

634 VIA CORSO CT, KISSIMMEE, FL, 34759
Community: Solivita
Sun City Center 1333 MISTY GREENS DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$325,000

3 beds

|

2 baths

|

1,725 sq ft

|

House

1333 MISTY GREENS DR, SUN CITY CENTER, F...
Community: Sun City Center
Ocala Palms 5247 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482
$234,900

2 beds

|

2 baths

|

1,161 sq ft

|

House

5247 NW 18TH ST, OCALA, FL, 34482
Community: Ocala Palms
Sun City Center 102 CAMBRIDGE TRL APT 229, SUN CITY CENT..., Sun City Center, FL 33573
$110,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

102 CAMBRIDGE TRL APT 229, SUN CITY CENT...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Henry Estates 669 WATERFORD DR, HAINES CITY, FL, 33844, Haines City, FL 33844
$255,000

3 beds

|

2 baths

|

1,741 sq ft

|

House

669 WATERFORD DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
Sun City Center 1812 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$485,000

3 beds

|

2 baths

|

2,606 sq ft

|

House

1812 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
Spruce Creek Country Club 9290 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$415,000

3 beds

|

2 baths

|

2,126 sq ft

|

House

9290 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Arlington Ridge 4546 SHENANDOAH RIVER TRL, LEESBURG, FL,..., Leesburg, FL 34748
$410,000

3 beds

|

2 baths

|

1,948 sq ft

|

House

4546 SHENANDOAH RIVER TRL, LEESBURG, FL,...
Community: Arlington Ridge
Lake Jovita Golf and Country Club 12314 LAKE JOVITA BLVD, DADE CITY, FL, 3..., Dade City, FL 33525
$775,000

5 beds

|

4 baths

|

3,275 sq ft

|

House

12314 LAKE JOVITA BLVD, DADE CITY, FL, 3...
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 North 10967 SW 65TH AVE, OCALA, FL, 34476, Ocala, FL 34476
$199,999

2 beds

|

2 baths

|

1,248 sq ft

|

House

10967 SW 65TH AVE, OCALA, FL, 34476
Community: Spruce Creek North
Lake Jovita Golf and Country Club 13816 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525
$825,000

4 beds

|

3 baths

|

2,825 sq ft

|

House

13816 THOROUGHBRED DR, DADE CITY, FL, 33...
Venetian Bay 424 LUNA BELLA LN 422, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$360,000

3 beds

|

3 baths

|

1,953 sq ft

|

Condo

424 LUNA BELLA LN 422, NEW SMYRNA BEACH,...
Community: Venetian Bay
Del Webb Oasis 14329 BRAEMAR ST, WINTER GARDEN, FL, 347..., Winter Garden, FL 34787
$500,000

3 beds

|

3 baths

|

1,788 sq ft

|

House

14329 BRAEMAR ST, WINTER GARDEN, FL, 347...
Community: Del Webb Oasis
Del Webb Oasis 12272 BRACCO ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$518,000

3 beds

|

3 baths

|

1,788 sq ft

|

House

12272 BRACCO ST, WINTER GARDEN, FL, 3478...
Community: Del Webb Oasis
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Foxwood Lake Estates 4859 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810
$174,000

2 beds

|

2 baths

|

828 sq ft

|

Manufactured Home

4859 FOXWOOD BLVD, LAKELAND, FL, 33810
On Top of the World 9728 SW 94TH AVE D, OCALA, FL, 34481, Ocala, FL 34481
$164,900

2 beds

|

2 baths

|

1,215 sq ft

|

Villa

9728 SW 94TH AVE D, OCALA, FL, 34481
Community: On Top of the World
Highlands Ridge 3929 PUMA DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$370,000

2 beds

|

2 baths

|

1,964 sq ft

|

House

3929 PUMA DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Mirada 31396 CABANA RYE AVE, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$350,000

2 beds

|

3 baths

|

1,747 sq ft

|

Townhouse

31396 CABANA RYE AVE, SAN ANTONIO, FL, 3...
Community: Mirada
Latitude Margaritaville 798 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$659,000

3 beds

|

3 baths

|

2,067 sq ft

|

House

798 JOLLYMON WAY, 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.
Lake James 7770 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$508,000

2 beds

|

2 baths

|

1,990 sq ft

|

House

7770 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Venetian Bay 3049 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$327,000

3 beds

|

3 baths

|

1,614 sq ft

|

House

3049 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Lake James 8160 LAKE JAMES DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$414,900

2 beds

|

2 baths

|

2,002 sq ft

|

House

8160 LAKE JAMES DR, LAKELAND, FL, 33810
Community: Lake James
Oak Run 11298 SW 73RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$335,000

2 beds

|

2 baths

|

1,540 sq ft

|

House

11298 SW 73RD CIR, OCALA, FL, 34476
Community: Oak Run
On Top of the World 9726 SW 94TH TER C, OCALA, FL, 34481, Ocala, FL 34481
$184,900

2 beds

|

2 baths

|

1,412 sq ft

|

Villa

9726 SW 94TH TER C, 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
Twin Lakes 5075 TWIN LAKES BLVD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$679,900

4 beds

|

4 baths

|

2,870 sq ft

|

House

5075 TWIN LAKES BLVD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Lake Ashton 1124 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$414,900

3 beds

|

2 baths

|

2,113 sq ft

|

House

1124 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Lakeside Landings 10173 JULIA ISLES AVE, OXFORD, FL, 34484, Oxford, FL 34484
$398,900

3 beds

|

2 baths

|

1,970 sq ft

|

House

10173 JULIA ISLES AVE, OXFORD, FL, 34484
Community: Lakeside Landings
On Top of the World 10075 SW 91ST PL, OCALA, FL, 34481, Ocala, FL 34481
$279,900

2 beds

|

2 baths

|

1,766 sq ft

|

House

10075 SW 91ST PL, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8737 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$419,000

3 beds

|

2 baths

|

2,280 sq ft

|

House

8737 SW 83RD CIR, OCALA, FL, 34481
Community: On Top of the World

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3,573 homes near Winter Garden
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