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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!
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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) VillageWalk at Lake Nona
$400Ks - $900Ks
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? 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
Huntington at Hunter's Ridge 71 WRENDALE LOOP, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$363,000

2 beds

|

2 baths

|

1,598 sq ft

|

Villa

71 WRENDALE LOOP, ORMOND BEACH, FL, 3217...
The Villages® 741 ROYAL PALM AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$182,000

2 beds

|

2 baths

|

1,056 sq ft

|

Manufactured Home

741 ROYAL PALM AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Del Webb Oasis 13732 FRESH IVY ST, WINTER GARDEN, FL, 3..., Winter Garden, FL 34787
$625,000

2 beds

|

2 baths

|

1,889 sq ft

|

House

13732 FRESH IVY ST, WINTER GARDEN, FL, 3...
Community: Del Webb Oasis
Del Webb Sunbridge 6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771
$514,990

3 beds

|

3 baths

|

2,077 sq ft

|

House

6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
Sun City Center 2236 PLATINUM DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$375,000

3 beds

|

3 baths

|

2,294 sq ft

|

House

2236 PLATINUM DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3138 AUREA PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$724,500

4 beds

|

3 baths

|

2,286 sq ft

|

House

3138 AUREA PL, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 815 CORTEZ AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$340,000

2 beds

|

2 baths

|

1,384 sq ft

|

House

815 CORTEZ AVE, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 17427 SE 78TH HARMONY CIR, THE VILLAGES,..., The Villages, FL 32162
$279,900

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

17427 SE 78TH HARMONY CIR, THE VILLAGES,...
Community: The Villages®
Sun City Center 1607 VINCENNES DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$225,000

3 beds

|

2 baths

|

1,402 sq ft

|

House

1607 VINCENNES DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
The Villages® 16751 SE 84TH COLERAIN CIR, THE VILLAGES..., The Villages, FL 32162
$399,999

3 beds

|

2 baths

|

1,917 sq ft

|

House

16751 SE 84TH COLERAIN CIR, THE VILLAGES...
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.
The Villages® 1524 CONWAY CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$344,900

2 beds

|

2 baths

|

1,196 sq ft

|

House

1524 CONWAY CT, THE VILLAGES, FL, 32162
Community: The Villages®
Spruce Creek North 6448 SW 111TH PL, OCALA, FL, 34476, Ocala, FL 34476
$229,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

6448 SW 111TH PL, OCALA, FL, 34476
Community: Spruce Creek North
Ocala Preserve 4748 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$249,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4748 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4754 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$249,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4754 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4736 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$249,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4736 NW 39TH STREET 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 4742 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$249,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4742 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Sun City Center 1308 CRYSTAL GREENS DR, SUN CITY CENTER,..., Sun City Center, FL 33573
$529,900

3 beds

|

2 baths

|

2,117 sq ft

|

House

1308 CRYSTAL GREENS DR, SUN CITY CENTER,...
Community: Sun City Center
The Villages® 276 LAWTHORN ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$725,000

3 beds

|

2 baths

|

2,266 sq ft

|

House

276 LAWTHORN ST, THE VILLAGES, FL, 32162
Community: The Villages®
Pine Run Estates 10012 SW 88TH CT, OCALA, FL, 34481, Ocala, FL 34481
$152,999

2 beds

|

2 baths

|

1,144 sq ft

|

House

10012 SW 88TH CT, OCALA, FL, 34481
Community: Pine Run Estates
Ocala Preserve 4082 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$259,990

2 beds

|

2 baths

|

1,614 sq ft

|

House

4082 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
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.
Ocala Preserve 4072 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$259,990

2 beds

|

2 baths

|

1,614 sq ft

|

House

4072 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
JB Ranch 4690 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$294,990

4 beds

|

2 baths

|

1,828 sq ft

|

House

4690 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
JB Ranch 4691 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$295,990

4 beds

|

2 baths

|

1,828 sq ft

|

House

4691 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
JB Ranch 4746 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$295,990

4 beds

|

2 baths

|

1,828 sq ft

|

House

4746 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
Four Seasons at Orlando 7778 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747
$725,000

3 beds

|

2 baths

|

1,970 sq ft

|

House

7778 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1828 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$312,000

3 beds

|

2 baths

|

1,579 sq ft

|

House

1828 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
New Pine Run Estates 8973 SW 102ND PL, OCALA, FL, 34481, Ocala, FL 34481
$169,900

2 beds

|

2 baths

|

1,040 sq ft

|

House

8973 SW 102ND PL, OCALA, FL, 34481
Community: Pine Run Estates
Spruce Creek South 9916 SE 175TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$279,900

2 beds

|

2 baths

|

1,603 sq ft

|

House

9916 SE 175TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
On Top of the World 9926 SW 95TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$337,700

2 beds

|

2 baths

|

1,680 sq ft

|

House

9926 SW 95TH LOOP, OCALA, FL, 34481
Community: On Top of the World
The Villages® 919 WEEPING WILLOW AVE, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$229,000

2 beds

|

2 baths

|

1,392 sq ft

|

Manufactured Home

919 WEEPING WILLOW AVE, LADY LAKE, FL, 3...
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.
The Villages® 525 CHULA VISTA AVE, THE VILLAGES, FL, 3..., The Villages, FL 32159
$309,000

2 beds

|

2 baths

|

1,410 sq ft

|

House

525 CHULA VISTA AVE, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 8383 SE 173RD HAMILTON PL, THE VILLAGES,..., The Villages, FL 32162
$315,000

3 beds

|

2 baths

|

1,586 sq ft

|

Villa

8383 SE 173RD HAMILTON PL, THE VILLAGES,...
Community: The Villages®
The Villages® 1877 W SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$232,000

2 beds

|

2 baths

|

1,388 sq ft

|

House

1877 W SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
The Villages® 976 CARIBOU WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$540,000

3 beds

|

2 baths

|

2,044 sq ft

|

House

976 CARIBOU WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 1709 S PEBBLE BEACH BLVD, SUN CITY CENTE..., Sun City Center, FL 33573
$305,000

2 beds

|

2 baths

|

1,857 sq ft

|

House

1709 S PEBBLE BEACH BLVD, SUN CITY CENTE...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 527 BEVILLE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$649,900

3 beds

|

2 baths

|

2,050 sq ft

|

House

527 BEVILLE PL, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1600 ARIAL PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$663,500

3 beds

|

2 baths

|

1,927 sq ft

|

House

1600 ARIAL PL, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1224 BALLESTEROS DR, THE VILLAGES, FL, 3..., The Villages, FL 32162
$274,900

2 beds

|

2 baths

|

1,148 sq ft

|

House

1224 BALLESTEROS DR, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 488 SETH RUN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$899,750

4 beds

|

3 baths

|

2,315 sq ft

|

House

488 SETH RUN, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 17353 SE 76TH FLINTLOCK TER, THE VILLAGE..., The Villages, FL 32162
$295,000

2 beds

|

2 baths

|

1,388 sq ft

|

House

17353 SE 76TH FLINTLOCK TER, THE VILLAGE...
Community: The Villages®

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3,573 homes near Winter Garden
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