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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) 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
Pelican Bay Daytona Beach 111 BROWN CRANE CT, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$329,000

3 beds

|

2 baths

|

2,046 sq ft

|

House

111 BROWN CRANE CT, DAYTONA BEACH, FL, 3...
The Villages® 919 CAMINO DEL REY DR, THE VILLAGES, FL,..., The Villages, FL 32159
$475,000

3 beds

|

2 baths

|

1,634 sq ft

|

House

919 CAMINO DEL REY DR, THE VILLAGES, FL,...
Community: The Villages®
Tampa Bay Golf and Country Club 10048 CLEGHORN DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$387,000

3 beds

|

2 baths

|

2,229 sq ft

|

House

10048 CLEGHORN DR, SAN ANTONIO, FL, 3357...
The Villages® 949 ISLE OF PALMS PATH, THE VILLAGES, FL..., The Villages, FL 32162
$879,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

949 ISLE OF PALMS PATH, THE VILLAGES, FL...
Community: The Villages®
Sun City Center 1604 CHEVY CHASE DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$234,900

2 beds

|

2 baths

|

1,266 sq ft

|

House

1604 CHEVY CHASE 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
Latitude Margaritaville 440 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$559,900

2 beds

|

2 baths

|

1,563 sq ft

|

House

440 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
The Villages® 12185 NE 51ST CIR, OXFORD, FL, 34484, Oxford, FL 34484
$339,000

3 beds

|

2 baths

|

1,889 sq ft

|

House

12185 NE 51ST CIR, OXFORD, FL, 34484
Community: The Villages®
Latitude Margaritaville 148 SIX STRING DR, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$719,900

2 beds

|

3 baths

|

2,347 sq ft

|

House

148 SIX STRING DR, DAYTONA BEACH, FL, 32...
Latitude Margaritaville 203 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$558,000

3 beds

|

2 baths

|

1,563 sq ft

|

House

203 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Lakeside Landings 5373 COMPASS PT # 1, OXFORD, FL, 34484, Oxford, FL 34484
$217,000

3 beds

|

2 baths

|

1,291 sq ft

|

Condo

5373 COMPASS PT # 1, OXFORD, FL, 34484
Community: Lakeside Landings
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 224 GRANADA LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$439,900

3 beds

|

2 baths

|

1,926 sq ft

|

House

224 GRANADA LN, DAVENPORT, FL, 33837
Community: Del Webb Orlando
The Villages® 2217 ISLEWORTH CIR, THE VILLAGES, FL, 32..., The Villages, FL 32163
$1,075,000

3 beds

|

2 baths

|

2,683 sq ft

|

House

2217 ISLEWORTH CIR, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 2077 VICKERS PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$850,000

3 beds

|

2 baths

|

2,415 sq ft

|

House

2077 VICKERS PL, THE VILLAGES, FL, 32163
Community: The Villages®
Solivita 469 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$499,000

3 beds

|

4 baths

|

2,616 sq ft

|

House

469 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Stonecrest 12183 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$425,000

3 beds

|

2 baths

|

1,915 sq ft

|

House

12183 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
SummerGlen 5877 SW 157TH PL, OCALA, FL, 34473, Ocala, FL 34473
$274,500

3 beds

|

2 baths

|

1,557 sq ft

|

House

5877 SW 157TH PL, OCALA, FL, 34473
Community: SummerGlen
Southshore Bay 17334 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$328,998

2 beds

|

3 baths

|

1,737 sq ft

|

Villa

17334 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Sun City Center 2427 SIFIELD GREENS WAY, SUN CITY CENTER..., Sun City Center, FL 33573
$289,500

2 beds

|

2 baths

|

1,396 sq ft

|

Condo

2427 SIFIELD GREENS WAY, SUN CITY CENTER...
Community: Sun City Center
Sun City Center 1112 MCDANIEL ST # 78, SUN CITY CENTER, ..., Sun City Center, FL 33573
$270,000

2 beds

|

2 baths

|

1,629 sq ft

|

Condo

1112 MCDANIEL ST # 78, SUN CITY CENTER, ...
Community: Sun City Center
Mirada 31921 MAGNA GULF LOOP, SAN ANTONIO, FL, ..., San Antonio, FL 33576
$509,900

3 beds

|

3 baths

|

2,231 sq ft

|

House

31921 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.
Latitude Margaritaville 162 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$399,999

2 beds

|

2 baths

|

1,466 sq ft

|

House

162 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Sandpiper Golf & Country Club 6004 SANDERLING DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$305,000

2 beds

|

2 baths

|

1,606 sq ft

|

House

6004 SANDERLING DR, LAKELAND, FL, 33809
The Villages® 412 HILDALGO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$265,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

412 HILDALGO DR, THE VILLAGES, FL, 32159
Community: The Villages®
New Scottish Highlands 301 BRIGADOON CIR # 301, LEESBURG, FL, 3..., Leesburg, FL 34788
$185,000

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

301 BRIGADOON CIR # 301, LEESBURG, FL, 3...
Community: Scottish Highlands
New Lake Ashton 5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$448,900

3 beds

|

2 baths

|

2,031 sq ft

|

House

5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Legacy of Leesburg 27302 ORCHID GLADE ST, LEESBURG, FL, 347..., Leesburg, FL 34748
$340,000

3 beds

|

2 baths

|

1,905 sq ft

|

House

27302 ORCHID GLADE ST, LEESBURG, FL, 347...
Community: Legacy of Leesburg
Spruce Creek South 17551 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$269,900

3 beds

|

2 baths

|

1,498 sq ft

|

House

17551 SE 96TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
The Villages® 1819 ZIRCON PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$775,000

4 beds

|

2 baths

|

2,534 sq ft

|

House

1819 ZIRCON PL, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1511 LAVACA LN, THE VILLAGES, FL, 32159, The Villages, FL 32159
$618,000

3 beds

|

2 baths

|

2,058 sq ft

|

House

1511 LAVACA LN, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1407 GEORGIANA TER, THE VILLAGES, FL, 32..., The Villages, FL 32162
$365,000

3 beds

|

2 baths

|

1,397 sq ft

|

Villa

1407 GEORGIANA TER, THE VILLAGES, FL, 32...
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® 1382 ZEST AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$279,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1382 ZEST AVE, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 8544 SE 177TH BARTRAM LOOP, THE VILLAGES..., The Villages, FL 32162
$320,000

2 beds

|

2 baths

|

1,481 sq ft

|

House

8544 SE 177TH BARTRAM LOOP, THE VILLAGES...
Community: The Villages®
The Villages® 1115 MCBEE AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$479,900

3 beds

|

2 baths

|

1,612 sq ft

|

Villa

1115 MCBEE AVE, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1116 SAN BERNARDO RD, THE VILLAGES, FL, ..., The Villages, FL 32162
$293,000

2 beds

|

2 baths

|

1,102 sq ft

|

Villa

1116 SAN BERNARDO RD, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 1219 SANTOS PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$255,000

2 beds

|

2 baths

|

1,383 sq ft

|

House

1219 SANTOS PL, LADY LAKE, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2188 GORDON PATH, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$399,900

3 beds

|

2 baths

|

1,539 sq ft

|

House

2188 GORDON PATH, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 202 ESTRADA PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$255,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

202 ESTRADA PL, THE VILLAGES, FL, 32159
Community: The Villages®
New Lake Ashton 4496 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$419,900

3 beds

|

2 baths

|

2,312 sq ft

|

House

4496 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
Spruce Creek South 15823 SE 101ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$299,990

4 beds

|

2 baths

|

1,828 sq ft

|

House

15823 SE 101ST CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
The Lakes at Harmony 3306 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$480,000

4 beds

|

3 baths

|

2,547 sq ft

|

House

3306 SAGEBRUSH ST, HARMONY, FL, 34773

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3,573 homes near Winter Garden
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