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

3,703 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 - $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
$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 - $700Ks
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 - $700Ks
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 - $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
<$100k - $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
$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
No reviews yet Venetian Bay
$300Ks - $2Ms
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 - $500Ks
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) 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
<$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 - $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 - $500Ks
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 | 1,024 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
$400Ks - $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
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $300Ks
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
VillageWalk at Lake Nona 11807 PADUA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$770,000

4 beds

|

4 baths

|

3,000 sq ft

|

House

11807 PADUA LN, ORLANDO, FL, 32827
SummerGlen 15705 SW 16TH TER, OCALA, FL, 34473, Ocala, FL 34473
$278,375

2 beds

|

2 baths

|

1,792 sq ft

|

House

15705 SW 16TH TER, OCALA, FL, 34473
Community: SummerGlen
Ridgehaven 454 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$545,000

4 beds

|

3 baths

|

2,791 sq ft

|

House

454 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
The Villages® 3233 LOWE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$530,000

3 beds

|

3 baths

|

2,056 sq ft

|

House

3233 LOWE CT, THE VILLAGES, FL, 32163
Community: The Villages®
Spruce Creek North 10740 SW 62ND AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34476
$191,500

2 beds

|

2 baths

|

1,092 sq ft

|

House

10740 SW 62ND AVENUE RD, OCALA, FL, 3447...
Community: Spruce Creek North
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ridgehaven 453 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$547,510

4 beds

|

3 baths

|

2,791 sq ft

|

House

453 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
Ridgehaven 457 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$519,810

4 beds

|

3 baths

|

2,487 sq ft

|

House

457 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
Valencia Lakes 15911 COBBLE MILL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$350,000

3 beds

|

2 baths

|

1,868 sq ft

|

House

15911 COBBLE MILL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Cherrywood 6008 SW 103RD LOOP, OCALA, FL, 34476, Ocala, FL 34476
$349,900

3 beds

|

2 baths

|

1,763 sq ft

|

House

6008 SW 103RD LOOP, OCALA, FL, 34476
Community: Cherrywood
Stonecrest 17409 SE 111TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$319,000

3 beds

|

2 baths

|

1,700 sq ft

|

House

17409 SE 111TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
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® 925 BEECHWOOD AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$225,000

2 beds

|

2 baths

|

1,568 sq ft

|

Manufactured Home

925 BEECHWOOD AVE, LADY LAKE, FL, 32159
Community: The Villages®
Sun City Center 2431 NANTUCKET HARBOR LOOP # 61, SUN CIT..., Sun City Center, FL 33573
$217,900

2 beds

|

2 baths

|

1,205 sq ft

|

Condo

2431 NANTUCKET HARBOR LOOP # 61, SUN CIT...
Community: Sun City Center
Plantation at Leesburg 4300 LEAFWAY CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,000

3 beds

|

2 baths

|

1,861 sq ft

|

House

4300 LEAFWAY CIR, LEESBURG, FL, 34748
Cherrywood 10523 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$219,900

2 beds

|

2 baths

|

1,295 sq ft

|

House

10523 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
El Dorado 3555 SW 24TH AVENUE RD, OCALA, FL, 34471, Ocala, FL 34471
$542,900

4 beds

|

3 baths

|

3,304 sq ft

|

House

3555 SW 24TH AVENUE RD, OCALA, FL, 34471
Community: El Dorado
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Oak Run 6758 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$229,900

2 beds

|

2 baths

|

1,550 sq ft

|

House

6758 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Oak Run
On Top of the World 9722 SW 95TH CT C, OCALA, FL, 34481, Ocala, FL 34481
$174,900

2 beds

|

2 baths

|

1,412 sq ft

|

Villa

9722 SW 95TH CT C, OCALA, FL, 34481
Community: On Top of the World
Plantation at Leesburg 3603 WESTOVER CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$415,000

2 beds

|

2 baths

|

2,399 sq ft

|

House

3603 WESTOVER CIR, LEESBURG, FL, 34748
Sun City Center 1360 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$470,000

3 beds

|

2 baths

|

2,482 sq ft

|

Condo

1360 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Mirada 31896 MAGNA GULF LOOP, SAN ANTONIO, FL, ..., San Antonio, FL 33576
$524,990

3 beds

|

3 baths

|

2,349 sq ft

|

House

31896 MAGNA GULF LOOP, SAN ANTONIO, FL, ...
Community: Mirada
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 920 VILLEROY GREENS DR, SUN CITY CENTER,..., Sun City Center, FL 33573
$230,000

2 beds

|

2 baths

|

1,757 sq ft

|

Condo

920 VILLEROY GREENS DR, SUN CITY CENTER,...
Community: Sun City Center
Sun City Center 1226 LYNDHURST GREENS DR, SUN CITY CENTE..., Sun City Center, FL 33573
$254,000

3 beds

|

2 baths

|

1,429 sq ft

|

Condo

1226 LYNDHURST GREENS DR, SUN CITY CENTE...
Community: Sun City Center
On Top of the World 8306 SW 79TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$356,200

3 beds

|

3 baths

|

1,850 sq ft

|

House

8306 SW 79TH CIR, OCALA, FL, 34476
Community: On Top of the World
The Villages® 506 DEAUVILLE CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$685,000

3 beds

|

2 baths

|

1,914 sq ft

|

House

506 DEAUVILLE CT, THE VILLAGES, FL, 3216...
Community: The Villages®
On Top of the World 8796 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$274,900

3 beds

|

2 baths

|

1,726 sq ft

|

House

8796 SW 83RD 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
Legacy of Leesburg 5135 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,900

3 beds

|

2 baths

|

2,055 sq ft

|

House

5135 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Lake Ashton 4152 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$250,000

2 beds

|

2 baths

|

1,319 sq ft

|

House

4152 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Highlands Ridge 4456 TOUSSANT DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$449,000

3 beds

|

2 baths

|

1,722 sq ft

|

House

4456 TOUSSANT DR, AVON PARK, FL, 33825
Community: Highlands Ridge
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...
Pine Run Estates 8879 SW 104TH LN, OCALA, FL, 34481, Ocala, FL 34481
$209,000

2 beds

|

2 baths

|

1,347 sq ft

|

House

8879 SW 104TH LN, OCALA, FL, 34481
Community: Pine Run Estates
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 26616 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$255,000

2 beds

|

2 baths

|

1,269 sq ft

|

House

26616 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
The Villages® 106 OAK BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$115,000

2 beds

|

2 baths

|

828 sq ft

|

Manufactured Home

106 OAK BLVD, WILDWOOD, FL, 34785
Community: The Villages®
Cherrywood 5968 SW 103RD LOOP, OCALA, FL, 34476, Ocala, FL 34476
$279,000

3 beds

|

2 baths

|

1,713 sq ft

|

House

5968 SW 103RD LOOP, OCALA, FL, 34476
Community: Cherrywood
Harbor Hills Country Club 39640 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$529,900

3 beds

|

3 baths

|

2,531 sq ft

|

House

39640 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Thunderbird Hill 3702 THUNDERBIRD HILL CIR, SEBRING, FL, ..., Sebring, FL 33872
$220,000

2 beds

|

2 baths

|

1,306 sq ft

|

Villa

3702 THUNDERBIRD HILL CIR, SEBRING, FL, ...
Community: Thunderbird Hill
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Tarawood 10501 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436
$230,000

3 beds

|

2 baths

|

1,627 sq ft

|

House

10501 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
Colonnades 4805 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$125,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

4805 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
Plantation at Leesburg 5305 INGLESIDE, LEESBURG, FL, 34748, Leesburg, FL 34748
$193,900

2 beds

|

2 baths

|

1,220 sq ft

|

Manufactured Home

5305 INGLESIDE, LEESBURG, FL, 34748
Ocala Palms 5340 NW 26TH LN, OCALA, FL, 34482, Ocala, FL 34482
$330,000

3 beds

|

2 baths

|

1,719 sq ft

|

House

5340 NW 26TH LN, OCALA, FL, 34482
Community: Ocala Palms
The Villages® 12328 NE 48TH LOOP, OXFORD, FL, 34484, Oxford, FL 34484
$280,000

3 beds

|

2 baths

|

1,495 sq ft

|

House

12328 NE 48TH LOOP, OXFORD, FL, 34484
Community: The Villages®

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3,703 homes near Winter Garden
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