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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
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
The Villages® 8377 SE 177TH BARTRAM LOOP, THE VILLAGES..., The Villages, FL 32162
$379,900

3 beds

|

2 baths

|

1,821 sq ft

|

House

8377 SE 177TH BARTRAM LOOP, THE VILLAGES...
Community: The Villages®
Sun City Center 1117 VILLEROY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$369,900

2 beds

|

2 baths

|

1,972 sq ft

|

House

1117 VILLEROY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Four Seasons at Orlando 7748 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747
$738,900

3 beds

|

3 baths

|

2,754 sq ft

|

House

7748 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...
Summer Trees 120 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$294,501

2 beds

|

2 baths

|

1,245 sq ft

|

House

120 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Heritage Hills 3640 SOLANA CIR A, CLERMONT, FL, 34711, Clermont, FL 34711
$309,900

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3640 SOLANA CIR A, CLERMONT, FL, 34711
Community: Heritage Hills
Lake Ashton 4577 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$375,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

4577 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
The Villages® 2450 MERIDA CIR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$385,000

3 beds

|

2 baths

|

1,851 sq ft

|

House

2450 MERIDA CIR, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 8678 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$324,900

3 beds

|

2 baths

|

1,695 sq ft

|

House

8678 SW 83RD CIR, OCALA, FL, 34481
Community: On Top of the World
Esplanade at Wiregrass Ranch 4520 FRECCIA LOOP, WESLEY CHAPEL, FL, 33..., Wesley Chapel, FL 33543
$845,000

3 beds

|

3 baths

|

2,403 sq ft

|

House

4520 FRECCIA LOOP, WESLEY CHAPEL, FL, 33...
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.
The Villages® 5068 NE 121ST AVE, OXFORD, FL, 34484, Oxford, FL 34484
$299,000

3 beds

|

2 baths

|

1,488 sq ft

|

House

5068 NE 121ST AVE, OXFORD, FL, 34484
Community: The Villages®
Sun City Center 1707 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$365,000

2 beds

|

2 baths

|

1,479 sq ft

|

House

1707 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
The Villages® 3495 RESTON DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$320,000

3 beds

|

2 baths

|

1,203 sq ft

|

House

3495 RESTON DR, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 9974 SW 88TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$339,900

2 beds

|

2 baths

|

1,975 sq ft

|

House

9974 SW 88TH LOOP, OCALA, FL, 34481
Community: On Top of the World
The Villages® 6295 DANIELSON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163
$749,000

4 beds

|

3 baths

|

2,514 sq ft

|

House

6295 DANIELSON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 2501 LONIGAN PL, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$215,000

2 beds

|

2 baths

|

1,394 sq ft

|

Condo

2501 LONIGAN PL, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Lakeside Landings 10021 LAKE MIONA WAY, OXFORD, FL, 34484, Oxford, FL 34484
$315,000

3 beds

|

2 baths

|

1,876 sq ft

|

House

10021 LAKE MIONA WAY, OXFORD, FL, 34484
Community: Lakeside Landings
Sun City Center 2490 KENSINGTON GREENS DR, SUN CITY CENT..., Sun City Center, FL 33573
$349,500

3 beds

|

3 baths

|

1,908 sq ft

|

Condo

2490 KENSINGTON GREENS DR, SUN CITY CENT...
Community: Sun City Center
Solivita 605 SAN AUGUSTO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$395,000

3 beds

|

2 baths

|

1,822 sq ft

|

House

605 SAN AUGUSTO DR, KISSIMMEE, FL, 34759
Community: Solivita
Latitude Margaritaville 307 CHEESEBURGER DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$372,600

2 beds

|

2 baths

|

1,205 sq ft

|

House

307 CHEESEBURGER DR, DAYTONA BEACH, FL, ...
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 176 CAPE FLORIDA DR, POINCIANA, FL, 3475..., Poinciana, FL 34759
$420,000

2 beds

|

2 baths

|

1,800 sq ft

|

House

176 CAPE FLORIDA DR, POINCIANA, FL, 3475...
Community: Solivita
The Villages® 17421 SE 81ST NEWBERRY CT, THE VILLAGES,..., The Villages, FL 32162
$245,000

2 beds

|

2 baths

|

1,179 sq ft

|

Villa

17421 SE 81ST NEWBERRY CT, THE VILLAGES,...
Community: The Villages®
Stone Creek 6409 SW 92ND CIR, OCALA, FL, 34481, Ocala, FL 34481
$259,900

3 beds

|

2 baths

|

1,596 sq ft

|

House

6409 SW 92ND CIR, OCALA, FL, 34481
Community: Stone Creek
Spruce Creek Country Club 8913 SE 132ND LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$475,900

3 beds

|

2 baths

|

2,413 sq ft

|

House

8913 SE 132ND LOOP, SUMMERFIELD, FL, 344...
Spruce Creek Country Club 12947 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$410,000

3 beds

|

2 baths

|

2,126 sq ft

|

House

12947 SE 97TH TERRACE RD, SUMMERFIELD, F...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 9603 SE 137TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$424,900

3 beds

|

2 baths

|

2,126 sq ft

|

House

9603 SE 137TH STREET RD, SUMMERFIELD, FL...
Solivita 621 SAN AUGUSTO DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$379,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

621 SAN AUGUSTO DR, POINCIANA, FL, 34759
Community: Solivita
Majestic Oaks Ocala 5365 SW 86TH PL, OCALA, FL, 34476, Ocala, FL 34476
$399,900

3 beds

|

3 baths

|

2,678 sq ft

|

House

5365 SW 86TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Majestic Oaks Ocala 8778 SW 59TH TER, OCALA, FL, 34476, Ocala, FL 34476
$499,483

4 beds

|

3 baths

|

2,707 sq ft

|

House

8778 SW 59TH TER, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Sun City Center 2421 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$359,900

3 beds

|

2 baths

|

1,901 sq ft

|

House

2421 E DEL WEBB BLVD, SUN CITY CENTER, F...
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.
Breakaway Trails 2 CREEK BEND WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$715,000

4 beds

|

4 baths

|

3,098 sq ft

|

House

2 CREEK BEND WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
Breakaway Trails 4 CREEK BEND WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$749,000

5 beds

|

3 baths

|

3,625 sq ft

|

House

4 CREEK BEND WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
Stone Creek 9423 SW 60TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$434,900

2 beds

|

2 baths

|

1,891 sq ft

|

House

9423 SW 60TH LANE RD, OCALA, FL, 34481
Community: Stone Creek
Four Seasons at Orlando 2108 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$359,900

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

2108 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Sun City Center 1813 ALLEGHENY DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$235,000

3 beds

|

2 baths

|

1,504 sq ft

|

House

1813 ALLEGHENY DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 3014 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$319,900

3 beds

|

3 baths

|

1,587 sq ft

|

Townhouse

3014 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Sun City Center 2306 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$210,000

2 beds

|

2 baths

|

1,642 sq ft

|

Condo

2306 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Sun City Center 2433 KENSINGTON GREENS DR, SUN CITY CENT..., Sun City Center, FL 33573
$269,000

2 beds

|

2 baths

|

1,456 sq ft

|

Villa

2433 KENSINGTON GREENS DR, SUN CITY CENT...
Community: Sun City Center
Spruce Creek Country Club 13727 SE 87TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$279,000

2 beds

|

2 baths

|

1,687 sq ft

|

House

13727 SE 87TH AVE, SUMMERFIELD, FL, 3449...
Esplanade at Wiregrass Ranch 29544 VELLETRI LN, WESLEY CHAPEL, FL, 33..., Wesley Chapel, FL 33543
$489,900

3 beds

|

2 baths

|

1,925 sq ft

|

House

29544 VELLETRI LN, WESLEY CHAPEL, FL, 33...

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3,573 homes near Winter Garden
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