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

106 communities 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 - $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 - $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
$200Ks - $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 - $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 - $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 - $600Ks
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 - $1Ms
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 - $600Ks
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
$200Ks - $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 - $900Ks
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
<$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 - $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 - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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 - $900Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
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
<$100k - $500Ks
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...
$400Ks - $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 - $800Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Oak Run 10819 SW 84TH TER, OCALA, FL, 34481, Ocala, FL 34481
$249,900

3 beds

|

2 baths

|

1,952 sq ft

|

House

10819 SW 84TH TER, OCALA, FL, 34481
Community: Oak Run
The Villages® 1032 VENTURA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$559,000

2 beds

|

2 baths

|

1,734 sq ft

|

House

1032 VENTURA DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 2202 KERSHAW RD, THE VILLAGES, FL, 32162, The Villages, FL 32162
$429,900

3 beds

|

2 baths

|

1,927 sq ft

|

House

2202 KERSHAW RD, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 744 BARRON PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$382,000

3 beds

|

2 baths

|

1,635 sq ft

|

House

744 BARRON PL, THE VILLAGES, FL, 32163
Community: The Villages®
Royal Highlands 5906 PRINCE PHILIP CT, LEESBURG, FL, 347..., Leesburg, FL 34748
$349,900

3 beds

|

2 baths

|

1,951 sq ft

|

House

5906 PRINCE PHILIP CT, LEESBURG, FL, 347...
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Lake Jovita Golf and Country Club 13816 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525
$825,000

4 beds

|

3 baths

|

2,825 sq ft

|

House

13816 THOROUGHBRED DR, DADE CITY, FL, 33...
Marco Polo Village 5323 SW 111TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476
$455,000

4 beds

|

3 baths

|

2,592 sq ft

|

House

5323 SW 111TH LANE RD, OCALA, FL, 34476
Community: Marco Polo Village
The Villages® 412 HILDALGO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$269,900

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

412 HILDALGO DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3500 COUNTRYSIDE PATH, THE VILLAGES, FL,..., The Villages, FL 32163
$395,000

3 beds

|

2 baths

|

1,531 sq ft

|

House

3500 COUNTRYSIDE PATH, THE VILLAGES, FL,...
Community: The Villages®
Solivita 2188 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$319,900

2 beds

|

2 baths

|

1,364 sq ft

|

House

2188 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
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.
Spruce Creek South 10476 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$244,000

2 beds

|

2 baths

|

1,473 sq ft

|

House

10476 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Lake James 7919 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$499,900

3 beds

|

2 baths

|

1,886 sq ft

|

House

7919 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
On Top of the World 9093 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$259,900

2 beds

|

2 baths

|

1,629 sq ft

|

House

9093 SW 91ST CIR, OCALA, FL, 34481
Community: On Top of the World
New Royal Highlands 22125 DRAW BRIDGE DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$390,000

3 beds

|

2 baths

|

2,200 sq ft

|

House

22125 DRAW BRIDGE DR, LEESBURG, FL, 3474...
Community: Royal Highlands
Lakeside Landings 10173 JULIA ISLES AVE, OXFORD, FL, 34484, Oxford, FL 34484
$399,500

3 beds

|

2 baths

|

2,149 sq ft

|

House

10173 JULIA ISLES AVE, OXFORD, FL, 34484
Community: Lakeside Landings
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New The Villages® 5778 HENRY LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$430,000

3 beds

|

2 baths

|

1,531 sq ft

|

House

5778 HENRY LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
Arlington Ridge 4210 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$492,000

3 beds

|

2 baths

|

2,011 sq ft

|

House

4210 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Valencia Lakes 4949 MARBLE SPRINGS CIR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$360,000

2 beds

|

2 baths

|

1,747 sq ft

|

Villa

4949 MARBLE SPRINGS CIR, WIMAUMA, FL, 33...
Community: Valencia Lakes
Royal Highlands 4814 SAINT ANDREWS ARC, LEESBURG, FL, 34..., Leesburg, FL 34748
$319,900

3 beds

|

2 baths

|

1,728 sq ft

|

House

4814 SAINT ANDREWS ARC, LEESBURG, FL, 34...
Community: Royal Highlands
Royal Highlands 4909 KELSO ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$350,000

3 beds

|

2 baths

|

1,875 sq ft

|

House

4909 KELSO ST, LEESBURG, FL, 34748
Community: Royal Highlands
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 1330 MISTY GREENS DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$320,000

2 beds

|

2 baths

|

1,820 sq ft

|

House

1330 MISTY GREENS DR, SUN CITY CENTER, F...
Community: Sun City Center
New Lakes at Laurel Highlands 2811 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$390,000

5 beds

|

3 baths

|

2,696 sq ft

|

House

2811 GRANDBURY GROVE RD, LAKELAND, FL, 3...
New Heritage Landings 2811 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$390,000

5 beds

|

3 baths

|

2,696 sq ft

|

House

2811 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
New Spruce Creek Country Club 9017 SE 119TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$359,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

9017 SE 119TH ST, SUMMERFIELD, FL, 34491
Stone Creek 9740 SW 68TH LN, OCALA, FL, 34481, Ocala, FL 34481
$409,000

2 beds

|

2 baths

|

2,164 sq ft

|

House

9740 SW 68TH LN, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Sandpiper Golf & Country Club 5771 MACAW PL, LAKELAND, FL, 33809, Lakeland, FL 33809
$259,800

2 beds

|

2 baths

|

1,293 sq ft

|

House

5771 MACAW PL, LAKELAND, FL, 33809
Solivita 3390 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$290,000

2 beds

|

2 baths

|

1,353 sq ft

|

House

3390 FALLBROOK DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 1146 W BOONE CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$235,000

2 beds

|

2 baths

|

1,418 sq ft

|

Manufactured Home

1146 W BOONE CT, LADY LAKE, FL, 32159
Community: The Villages®
Solivita 724 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$329,000

2 beds

|

3 baths

|

1,938 sq ft

|

House

724 VILLA PARK RD, KISSIMMEE, FL, 34759
Community: Solivita
New Tampa Bay Golf and Country Club 29702 TEE SHOT DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$279,900

2 beds

|

2 baths

|

1,489 sq ft

|

House

29702 TEE SHOT DR, SAN ANTONIO, FL, 3357...
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 Orlando 793 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$299,000

2 beds

|

2 baths

|

1,468 sq ft

|

House

793 ASTURIAS RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Ocala Palms 5137 NW 20TH PL, OCALA, FL, 34482, Ocala, FL 34482
$319,000

2 beds

|

2 baths

|

1,569 sq ft

|

House

5137 NW 20TH PL, OCALA, FL, 34482
Community: Ocala Palms
Harbor Hills Country Club 39145 TREELINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$440,000

2 beds

|

3 baths

|

2,030 sq ft

|

House

39145 TREELINE DR, LADY LAKE, FL, 32159
Plantation at Leesburg 25007 BELLEVUE, LEESBURG, FL, 34748, Leesburg, FL 34748
$238,000

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

25007 BELLEVUE, LEESBURG, FL, 34748
Cherrywood 10350 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$212,000

2 beds

|

2 baths

|

1,667 sq ft

|

House

10350 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 25333 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$275,000

3 beds

|

2 baths

|

1,737 sq ft

|

House

25333 RIVER CREST DR, LEESBURG, FL, 3474...
Plantation at Leesburg 5300 TIGERS TAIL, LEESBURG, FL, 34748, Leesburg, FL 34748
$190,000

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

5300 TIGERS TAIL, LEESBURG, FL, 34748
Plantation at Leesburg 25642 OAK ALY, LEESBURG, FL, 34748, Leesburg, FL 34748
$225,000

2 beds

|

2 baths

|

1,730 sq ft

|

House

25642 OAK ALY, LEESBURG, FL, 34748
Plantation at Leesburg 4553 BELLE GRV, LEESBURG, FL, 34748, Leesburg, FL 34748
$245,000

2 beds

|

2 baths

|

1,420 sq ft

|

House

4553 BELLE GRV, LEESBURG, FL, 34748
Plantation at Leesburg 25274 LOST OAK CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$317,000

2 beds

|

2 baths

|

1,980 sq ft

|

House

25274 LOST OAK CIR, LEESBURG, FL, 34748

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106 communities near Winter Garden
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