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

3,551 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 - $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 - $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 - $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 - $500Ks
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 - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
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
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
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 - $700Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
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
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 - $500Ks
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) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
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
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
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
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, FL? 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
4.4 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
$100Ks - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
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
New Valencia Lakes 15737 CRYSTAL WATERS DR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$400,000

2 beds

|

2 baths

|

1,954 sq ft

|

House

15737 CRYSTAL WATERS DR, WIMAUMA, FL, 33...
Community: Valencia Lakes
New The Villages® 3104 BURBANK LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$385,000

3 beds

|

2 baths

|

1,932 sq ft

|

House

3104 BURBANK LN, THE VILLAGES, FL, 32162
Community: The Villages®
Four Seasons at Orlando 7957 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$499,900

3 beds

|

2 baths

|

2,271 sq ft

|

House

7957 HANSON BAY PL, KISSIMMEE, FL, 34747
The Villages® 949 ISLE OF PALMS PATH, THE VILLAGES, FL..., The Villages, FL 32162
$849,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

949 ISLE OF PALMS PATH, THE VILLAGES, FL...
Community: The Villages®
The Villages® 362 ARBELLA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$349,000

2 beds

|

2 baths

|

1,393 sq ft

|

House

362 ARBELLA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8231 SW 79TH CT, OCALA, FL, 34476, Ocala, FL 34476
$275,000

3 beds

|

2 baths

|

1,963 sq ft

|

House

8231 SW 79TH CT, OCALA, FL, 34476
Community: On Top of the World
Twin Lakes 5150 GARDENROW DR, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$328,770

2 beds

|

2 baths

|

1,322 sq ft

|

Villa

5150 GARDENROW DR, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Spruce Creek Preserve 14117 SW 115TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$199,900

2 beds

|

2 baths

|

1,296 sq ft

|

House

14117 SW 115TH CIR, DUNNELLON, FL, 34432
New Spruce Creek Country Club 13766 SE 89TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$339,900

3 beds

|

2 baths

|

2,025 sq ft

|

House

13766 SE 89TH AVE, SUMMERFIELD, FL, 3449...
Ridgehaven 1126 CLIFFHAVEN CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$569,990

3 beds

|

3 baths

|

2,344 sq ft

|

House

1126 CLIFFHAVEN CT, ORMOND BEACH, FL, 32...
Community: Ridgehaven
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.
Twin Lakes 2781 BUCKEYE LN, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$337,690

2 beds

|

2 baths

|

1,322 sq ft

|

Villa

2781 BUCKEYE LN, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Spruce Creek Preserve 13798 SW 111TH AVE, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$245,000

2 beds

|

2 baths

|

1,866 sq ft

|

House

13798 SW 111TH AVE, DUNNELLON, FL, 34432
New The Villages® 3102 RAVEN CROFT TER, THE VILLAGES, FL, ..., The Villages, FL 32163
$525,000

3 beds

|

2 baths

|

1,965 sq ft

|

House

3102 RAVEN CROFT TER, THE VILLAGES, FL, ...
Community: The Villages®
Spruce Creek Country Club 9105 SE 125TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$379,000

2 beds

|

2 baths

|

2,148 sq ft

|

House

9105 SE 125TH LOOP, SUMMERFIELD, FL, 344...
Palms at Serenoa 3860 GOLDENROD CT, CLERMONT, FL, 34714, Clermont, FL 34714
$368,000

3 beds

|

2 baths

|

1,621 sq ft

|

House

3860 GOLDENROD CT, CLERMONT, FL, 34714
Community: Palms at Serenoa
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 3009 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$321,000

3 beds

|

3 baths

|

1,614 sq ft

|

Townhouse

3009 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
SummerGlen 16205 SW 12TH TER, OCALA, FL, 34473, Ocala, FL 34473
$329,900

3 beds

|

2 baths

|

1,968 sq ft

|

House

16205 SW 12TH TER, OCALA, FL, 34473
Community: SummerGlen
Spruce Creek Preserve 11283 SW 139TH PL, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$259,000

3 beds

|

2 baths

|

1,772 sq ft

|

House

11283 SW 139TH PL, DUNNELLON, FL, 34432
Spruce Creek Preserve 13781 SW 112TH TER, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$270,000

3 beds

|

2 baths

|

2,016 sq ft

|

House

13781 SW 112TH TER, DUNNELLON, FL, 34432
Spruce Creek Preserve 11518 SW 136TH PL, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$200,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

11518 SW 136TH PL, DUNNELLON, FL, 34432
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.
Sun City Center 1649 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$364,900

3 beds

|

2 baths

|

1,911 sq ft

|

House

1649 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Spruce Creek Preserve 11411 SW 139TH PL, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$324,900

2 beds

|

2 baths

|

1,719 sq ft

|

House

11411 SW 139TH PL, DUNNELLON, FL, 34432
Spruce Creek Preserve 11411 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$269,000

3 beds

|

2 baths

|

1,974 sq ft

|

House

11411 SW 138TH LN, DUNNELLON, FL, 34432
Spruce Creek Preserve 11228 SW 138TH PL, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$249,000

2 beds

|

2 baths

|

1,678 sq ft

|

House

11228 SW 138TH PL, DUNNELLON, FL, 34432
Spruce Creek Country Club 13485 SE 93RD COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$389,900

2 beds

|

2 baths

|

1,826 sq ft

|

House

13485 SE 93RD COURT RD, SUMMERFIELD, FL,...
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Legacy of Leesburg 27238 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$440,000

4 beds

|

2 baths

|

2,585 sq ft

|

House

27238 STONEY BROOK DR, LEESBURG, FL, 347...
Community: Legacy of Leesburg
Sandpiper Golf & Country Club 6381 EGRET DR APT 25, LAKELAND, FL, 3380..., Lakeland, FL 33809
$270,000

2 beds

|

2 baths

|

1,383 sq ft

|

Villa

6381 EGRET DR APT 25, LAKELAND, FL, 3380...
Spruce Creek Preserve 11369 SW 139TH ST, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$257,000

2 beds

|

2 baths

|

1,654 sq ft

|

House

11369 SW 139TH ST, DUNNELLON, FL, 34432
The Villages® 776 ALCOTT AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$435,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

776 ALCOTT AVE, THE VILLAGES, FL, 32162
Community: The Villages®
Spruce Creek Preserve 11552 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$264,000

3 beds

|

2 baths

|

1,760 sq ft

|

House

11552 SW 138TH LN, DUNNELLON, FL, 34432
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.
Twin Lakes 2658 MIDSWEET AVE, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$493,870

2 beds

|

2 baths

|

1,921 sq ft

|

House

2658 MIDSWEET AVE, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Venetian Bay 422 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$629,990

4 beds

|

3 baths

|

2,542 sq ft

|

House

422 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
VillageWalk at Lake Nona 11858 BARLETTA DR, ORLANDO, FL, 32827, Orlando, FL 32827
$608,000

3 beds

|

2 baths

|

1,941 sq ft

|

House

11858 BARLETTA DR, ORLANDO, FL, 32827
Venetian Bay 672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$624,684

4 beds

|

4 baths

|

2,748 sq ft

|

House

672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Venetian Bay 673 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$729,384

6 beds

|

5 baths

|

4,181 sq ft

|

House

673 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 703 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$459,990

3 beds

|

3 baths

|

2,226 sq ft

|

House

703 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Twin Lakes 5040 GARDENROW DR, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$325,580

2 beds

|

2 baths

|

1,322 sq ft

|

Villa

5040 GARDENROW DR, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Venetian Bay 677 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$664,689

4 beds

|

4 baths

|

3,221 sq ft

|

House

677 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Venetian Bay 118 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$399,990

3 beds

|

2 baths

|

1,900 sq ft

|

House

118 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Spruce Creek Preserve 11298 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$238,000

2 beds

|

2 baths

|

1,408 sq ft

|

House

11298 SW 138TH LN, DUNNELLON, FL, 34432

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3,551 homes near Winter Garden
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