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

3,964 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
<$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
$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...
$100Ks - $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
$100Ks - $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
Royal Palm 1333 COCONUT PALM CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128
$435,000

3 beds

|

2 baths

|

2,060 sq ft

|

House

1333 COCONUT PALM CIR, PORT ORANGE, FL, ...
Community: Royal Palm
Valencia Lakes 15657 AURORA LAKE CIR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$379,900

3 beds

|

2 baths

|

1,764 sq ft

|

Villa

15657 AURORA LAKE CIR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
Twin Lakes 2527 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$299,500

2 beds

|

2 baths

|

1,346 sq ft

|

Halfplex

2527 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Plantation at Leesburg 24801 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$259,900

3 beds

|

2 baths

|

2,037 sq ft

|

House

24801 CRANES ROOST CIR, LEESBURG, FL, 34...
On Top of the World 8303 SW 82ND CIR, OCALA, FL, 34481, Ocala, FL 34481
$329,900

3 beds

|

2 baths

|

1,827 sq ft

|

House

8303 SW 82ND CIR, 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 461 TREVISO DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$454,900

3 beds

|

3 baths

|

2,266 sq ft

|

House

461 TREVISO DR, POINCIANA, FL, 34759
Community: Solivita
Solivita 555 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$310,000

3 beds

|

2 baths

|

1,610 sq ft

|

House

555 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
Solivita 316 TREVISO DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$559,000

3 beds

|

3 baths

|

2,320 sq ft

|

House

316 TREVISO DR, POINCIANA, FL, 34759
Community: Solivita
Solivita 2285 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$364,500

2 beds

|

2 baths

|

1,703 sq ft

|

House

2285 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
Breakaway Trails 4 CREEK BLUFF WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$500,000

3 beds

|

2 baths

|

2,575 sq ft

|

House

4 CREEK BLUFF WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
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 9350 SW 91ST COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$339,000

2 beds

|

2 baths

|

1,970 sq ft

|

House

9350 SW 91ST COURT RD, OCALA, FL, 34481
Community: On Top of the World
Valencia del Sol 4920 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598
$589,990

3 beds

|

3 baths

|

2,252 sq ft

|

House

4920 SEVILLA SHORES DR, WIMAUMA, FL, 335...
Community: Valencia del Sol
Solivita 1948 MOLISE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$419,900

3 beds

|

2 baths

|

1,849 sq ft

|

House

1948 MOLISE DR, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 2724 PALM TREE DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$309,900

2 beds

|

2 baths

|

1,539 sq ft

|

Villa

2724 PALM TREE DR, POINCIANA, FL, 34759
Community: Solivita
Venetian Bay 2931 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168
$789,900

4 beds

|

3 baths

|

2,511 sq ft

|

House

2931 BELLA FLORE TER, NEW SMYRNA BEACH, ...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1676 VAN BUREN WAY, THE VILLAGES, FL, 32..., The Villages, FL 32162
$454,900

3 beds

|

2 baths

|

1,840 sq ft

|

House

1676 VAN BUREN WAY, THE VILLAGES, FL, 32...
Community: The Villages®
Sun City Center 611 TREMONT GREENS LN, SUN CITY CENTER, ..., Sun City Center, FL 33573
$179,990

2 beds

|

2 baths

|

974 sq ft

|

Villa

611 TREMONT GREENS LN, SUN CITY CENTER, ...
Community: Sun City Center
Sun City Center 1735 COUNCIL DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$310,000

3 beds

|

1 baths

|

1,375 sq ft

|

House

1735 COUNCIL DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Colonnades 4856 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$249,900

2 beds

|

2 baths

|

1,312 sq ft

|

House

4856 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
The Villages® 3141 ROSWELL RD, THE VILLAGES, FL, 32162, The Villages, FL 32162
$549,900

3 beds

|

2 baths

|

2,216 sq ft

|

House

3141 ROSWELL RD, THE VILLAGES, FL, 32162
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.
JB Ranch 9237 SW 60TH TERRACE RD, OCALA, FL, 3447..., Ocala, FL 34476
$362,999

4 beds

|

2 baths

|

2,034 sq ft

|

House

9237 SW 60TH TERRACE RD, OCALA, FL, 3447...
Community: JB Ranch
On Top of the World 10625 SW 98TH PL, OCALA, FL, 34481, Ocala, FL 34481
$381,000

2 beds

|

2 baths

|

2,019 sq ft

|

House

10625 SW 98TH PL, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 339 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$244,900

2 beds

|

2 baths

|

1,516 sq ft

|

House

339 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Pine Run Estates 10170 SW 96TH CT, OCALA, FL, 34481, Ocala, FL 34481
$164,990

2 beds

|

2 baths

|

1,176 sq ft

|

House

10170 SW 96TH CT, OCALA, FL, 34481
Community: Pine Run Estates
The Villages® 871 IRON OAK WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$1,250,000

3 beds

|

2 baths

|

2,626 sq ft

|

House

871 IRON OAK WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
SummerGlen 15119 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$410,000

3 beds

|

2 baths

|

1,869 sq ft

|

House

15119 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Breakaway Trails 3 FOREST VIEW WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$529,900

3 beds

|

2 baths

|

2,737 sq ft

|

House

3 FOREST VIEW WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
Latitude Margaritaville 340 TIKI TER, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$467,500

2 beds

|

2 baths

|

1,563 sq ft

|

House

340 TIKI TER, DAYTONA BEACH, FL, 32124
Latitude Margaritaville 664 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$625,000

2 beds

|

2 baths

|

1,922 sq ft

|

House

664 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 798 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$685,000

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.
Latitude Margaritaville 126 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$729,987

3 beds

|

3 baths

|

2,338 sq ft

|

House

126 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Latitude Margaritaville 182 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$700,000

3 beds

|

3 baths

|

2,303 sq ft

|

House

182 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Latitude Margaritaville 643 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$447,700

2 beds

|

2 baths

|

1,503 sq ft

|

House

643 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 586 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$510,000

3 beds

|

2 baths

|

1,862 sq ft

|

House

586 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Latitude Margaritaville 220 SAND BAR LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$519,000

2 beds

|

2 baths

|

1,771 sq ft

|

House

220 SAND BAR LN, DAYTONA BEACH, FL, 3212...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 484 TROPICS AVE, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$674,900

3 beds

|

3 baths

|

2,080 sq ft

|

House

484 TROPICS AVE, DAYTONA BEACH, FL, 3212...
Latitude Margaritaville 544 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$715,000

2 beds

|

3 baths

|

2,067 sq ft

|

House

544 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Pine Run Estates 10495 SW 100TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$129,000

2 beds

|

1 baths

|

672 sq ft

|

House

10495 SW 100TH AVE, OCALA, FL, 34481
Community: Pine Run Estates
Solivita 151 BELL TOWER XING W, KISSIMMEE, FL, 34..., Kissimmee, FL 34759
$239,000

2 beds

|

2 baths

|

1,356 sq ft

|

House

151 BELL TOWER XING W, KISSIMMEE, FL, 34...
Community: Solivita
Sun City Center 761 TREMONT GREENS LN # 61, SUN CITY CEN..., Sun City Center, FL 33573
$192,000

2 beds

|

2 baths

|

1,110 sq ft

|

Condo

761 TREMONT GREENS LN # 61, SUN CITY CEN...
Community: Sun City Center

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3,964 homes near Winter Garden
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