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Winter Garden, FL 55+ active adult communities & homes for sale - Page 46

3,517 homes near Winter Garden

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5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
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 - $700Ks
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 - $500Ks
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 - $600Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
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3.6 rating (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $900Ks
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
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 (2 reviews) Plantation at Leesburg
$100Ks - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
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 - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
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Pelican Bay Daytona Beach
$100Ks - $400Ks
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
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $600Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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 (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
Venetian Bay
$200Ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
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Questions? Call us: (689) 407-5757
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
4 rating (7 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
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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) Pennbrooke Fairways
<$100k - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$200Ks - $400Ks
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
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Questions? Call us: (689) 407-5757
5 rating (5 reviews) SummerGlen
$100Ks - $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
Breakaway Trails
$400Ks - $800Ks
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
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.
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
4.8 rating (6 reviews) Highland Lakes
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
The Villages® 19201 SANDALWOOD DR # 19201, WILDWOOD, F..., Wildwood, FL 34785
$115,000

1 beds

|

1 baths

|

872 sq ft

|

Condo

19201 SANDALWOOD DR # 19201, WILDWOOD, F...
Community: The Villages®
Huntington at Hunter's Ridge 34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$330,000

3 beds

|

2 baths

|

1,523 sq ft

|

House

34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Highlands Ridge 4456 TOUSSANT DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$419,000

3 beds

|

2 baths

|

1,722 sq ft

|

House

4456 TOUSSANT DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Solivita 582 SAN JOAQUIN RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$369,900

3 beds

|

2 baths

|

1,730 sq ft

|

House

582 SAN JOAQUIN RD, KISSIMMEE, FL, 34759
Community: Solivita
Cresswind at Victoria Gardens 213 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724
$362,000

2 beds

|

2 baths

|

1,507 sq ft

|

House

213 OLD MOSS CIR, DELAND, FL, 32724
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 10248 SW 93RD PL, OCALA, FL, 34481, Ocala, FL 34481
$625,000

3 beds

|

3 baths

|

2,828 sq ft

|

House

10248 SW 93RD PL, OCALA, FL, 34481
Community: On Top of the World
Solivita 506 TAPATIO LN, POINCIANA, FL, 34759, Poinciana, FL 34759
$549,000

3 beds

|

3 baths

|

2,509 sq ft

|

House

506 TAPATIO LN, POINCIANA, FL, 34759
Community: Solivita
Valencia Lakes 16101 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$390,000

3 beds

|

2 baths

|

1,912 sq ft

|

House

16101 CAPE CORAL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Lakes of Mount Dora 8456 NORWICH WAY, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$648,999

4 beds

|

3 baths

|

2,460 sq ft

|

House

8456 NORWICH WAY, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
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 806 EBB TIDE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$429,000

3 beds

|

3 baths

|

2,011 sq ft

|

House

806 EBB TIDE LN, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 2448 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$309,900

3 beds

|

2 baths

|

1,539 sq ft

|

Villa

2448 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
Royal Palm 1315 COCONUT PALM CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128
$419,800

4 beds

|

2 baths

|

1,989 sq ft

|

House

1315 COCONUT PALM CIR, PORT ORANGE, FL, ...
Community: Royal Palm
Tampa Bay Golf and Country Club 11027 DORMIE DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$297,000

2 beds

|

2 baths

|

1,700 sq ft

|

House

11027 DORMIE DR, SAN ANTONIO, FL, 33576
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 7809 SW 86TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$265,000

3 beds

|

2 baths

|

1,465 sq ft

|

House

7809 SW 86TH LOOP, OCALA, FL, 34476
Community: On Top of the World
Arlington Ridge 4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$389,900

4 beds

|

2 baths

|

1,857 sq ft

|

House

4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Venetian Bay 3124 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$389,000

3 beds

|

3 baths

|

1,916 sq ft

|

House

3124 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Valencia del Sol 4914 SIENNA ISLES AVE, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$389,900

2 beds

|

3 baths

|

2,040 sq ft

|

Villa

4914 SIENNA ISLES AVE, WIMAUMA, FL, 3359...
Community: Valencia del Sol
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.
Del Webb Minneola 1517 EVENING SUMMIT CIR, MINNEOLA, FL, 3..., Minneola, FL 34715
$1,200,000

4 beds

|

4 baths

|

2,808 sq ft

|

House

1517 EVENING SUMMIT CIR, MINNEOLA, FL, 3...
Community: Del Webb Minneola
Lake Ashton 4576 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$344,500

2 beds

|

2 baths

|

1,514 sq ft

|

House

4576 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
Vienna Square 1614 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$225,000

2 beds

|

2 baths

|

1,164 sq ft

|

Villa

1614 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Tampa Bay Golf and Country Club 10926 COLLAR DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$360,000

2 beds

|

2 baths

|

1,590 sq ft

|

House

10926 COLLAR DR, SAN ANTONIO, FL, 33576
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3165 HUDSON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$447,500

3 beds

|

2 baths

|

2,176 sq ft

|

House

3165 HUDSON CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 2016 PEACEFUL PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$299,900

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

2016 PEACEFUL PL, THE VILLAGES, FL, 3216...
Community: The Villages®
Latitude Margaritaville 205 CHEESEBURGER DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$625,000

2 beds

|

2 baths

|

1,922 sq ft

|

House

205 CHEESEBURGER DR, DAYTONA BEACH, FL, ...
Highland Lakes 27107 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$259,900

2 beds

|

2 baths

|

1,474 sq ft

|

House

27107 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland 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.
Highland Lakes 6033 WADE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$239,900

2 beds

|

2 baths

|

1,632 sq ft

|

House

6033 WADE ST, LEESBURG, FL, 34748
Community: Highland Lakes
Gatherings of Lake Nona 7565 LAUREATE BLVD UNIT 3304, ORLANDO, F..., Orlando, FL 32827
$450,000

2 beds

|

2 baths

|

1,486 sq ft

|

Condo

7565 LAUREATE BLVD UNIT 3304, ORLANDO, F...
VillageWalk at Lake Nona 11863 FIORE DR, ORLANDO, FL, 32827, Orlando, FL 32827
$460,000

2 beds

|

2 baths

|

1,582 sq ft

|

Halfplex

11863 FIORE DR, ORLANDO, FL, 32827
Marion Landing 7707 SW 88TH STREET RD, OCALA, FL, 34476, Ocala, FL 34476
$264,900

2 beds

|

2 baths

|

1,465 sq ft

|

House

7707 SW 88TH STREET RD, OCALA, FL, 34476
Community: Marion Landing
On Top of the World 8710 SW 96TH ST C, OCALA, FL, 34481, Ocala, FL 34481
$114,900

2 beds

|

2 baths

|

1,179 sq ft

|

Villa

8710 SW 96TH ST 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
Plantation at Leesburg 25125 BELLEVUE, LEESBURG, FL, 34748, Leesburg, FL 34748
$160,000

2 beds

|

2 baths

|

936 sq ft

|

Manufactured Home

25125 BELLEVUE, LEESBURG, FL, 34748
The Villages® 7326 SE 173RD ARLINGTON LOOP, THE VILLAG..., The Villages, FL 32162
$324,900

3 beds

|

2 baths

|

1,490 sq ft

|

House

7326 SE 173RD ARLINGTON LOOP, THE VILLAG...
Community: The Villages®
Summit Greens 1063 MESA VERDE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$385,000

3 beds

|

2 baths

|

1,900 sq ft

|

House

1063 MESA VERDE CT, CLERMONT, FL, 34711
Community: Summit Greens
Highland Fairways 3535 SADDLEBROOK WAY, LAKELAND, FL, 3381..., Lakeland, FL 33810
$369,900

3 beds

|

2 baths

|

2,145 sq ft

|

House

3535 SADDLEBROOK WAY, LAKELAND, FL, 3381...
Community: Highland Fairways
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 9002 SW 96TH LN C, OCALA, FL, 34481, Ocala, FL 34481
$169,900

2 beds

|

2 baths

|

1,728 sq ft

|

Condo

9002 SW 96TH LN C, OCALA, FL, 34481
Community: On Top of the World
Four Seasons at Orlando 7916 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$575,000

3 beds

|

3 baths

|

2,470 sq ft

|

House

7916 HANSON BAY PL, KISSIMMEE, FL, 34747
Sun City Center 1805 BUTTERFLY PL, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$285,000

2 beds

|

2 baths

|

1,516 sq ft

|

House

1805 BUTTERFLY PL, SUN CITY CENTER, FL, ...
Community: Sun City Center
Southshore Bay 17253 STAR BANKS ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$385,000

2 beds

|

2 baths

|

1,956 sq ft

|

House

17253 STAR BANKS ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Majestic Oaks Ocala 8598 SW 59TH TER, OCALA, FL, 34476, Ocala, FL 34476
$460,000

4 beds

|

4 baths

|

2,835 sq ft

|

House

8598 SW 59TH TER, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Four Seasons at Orlando 2031 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$339,000

2 beds

|

2 baths

|

1,557 sq ft

|

Villa

2031 KEY BAY TRL, KISSIMMEE, FL, 34747

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