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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) 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 - $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
$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
Spruce Creek Country Club 13885 DEL WEBB BLVD, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$415,000

3 beds

|

2 baths

|

2,213 sq ft

|

House

13885 DEL WEBB BLVD, SUMMERFIELD, FL, 34...
On Top of the World 7917 SW 85TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$349,900

3 beds

|

2 baths

|

1,953 sq ft

|

House

7917 SW 85TH LOOP, OCALA, FL, 34476
Community: On Top of the World
Ocala Preserve 5587 NW 40TH PL, OCALA, FL, 34482, Ocala, FL 34482
$294,750

2 beds

|

2 baths

|

1,492 sq ft

|

House

5587 NW 40TH PL, OCALA, FL, 34482
Community: Ocala Preserve
Traditions at Lake Ruby 3986 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$415,000

4 beds

|

3 baths

|

2,320 sq ft

|

House

3986 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Scottish Highlands 1902 TWEED CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$190,000

2 beds

|

2 baths

|

1,176 sq ft

|

House

1902 TWEED CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Palms 2031 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$329,500

3 beds

|

2 baths

|

1,621 sq ft

|

House

2031 NW 50TH CIR, OCALA, FL, 34482
Community: Ocala Palms
SummerGlen 15705 SW 16TH TER, OCALA, FL, 34473, Ocala, FL 34473
$289,900

2 beds

|

2 baths

|

1,795 sq ft

|

House

15705 SW 16TH TER, OCALA, FL, 34473
Community: SummerGlen
Sullivan Ranch 30308 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$398,000

3 beds

|

2 baths

|

1,851 sq ft

|

House

30308 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Oak Run 8450 SW 115TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481
$236,000

3 beds

|

2 baths

|

1,689 sq ft

|

House

8450 SW 115TH STREET RD, OCALA, FL, 3448...
Community: Oak Run
The Villages® 523 BONITA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$209,000

2 beds

|

2 baths

|

1,332 sq ft

|

Manufactured Home

523 BONITA DR, THE VILLAGES, FL, 32159
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.
New Sandpiper Golf & Country Club 6059 CONDOR DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$395,000

3 beds

|

2 baths

|

2,195 sq ft

|

House

6059 CONDOR DR, LAKELAND, FL, 33809
New Spruce Creek South 17965 SE 102ND TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$175,300

2 beds

|

2 baths

|

1,296 sq ft

|

House

17965 SE 102ND TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
New Stone Creek 9725 SW 68TH LN, OCALA, FL, 34481, Ocala, FL 34481
$389,500

2 beds

|

2 baths

|

1,701 sq ft

|

House

9725 SW 68TH LN, OCALA, FL, 34481
Community: Stone Creek
New On Top of the World 8755 SW 79TH PL, OCALA, FL, 34481, Ocala, FL 34481
$429,000

3 beds

|

2 baths

|

2,126 sq ft

|

House

8755 SW 79TH PL, OCALA, FL, 34481
Community: On Top of the World
New The Villages® 1273 SPARTANBURG WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$530,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

1273 SPARTANBURG WAY, THE VILLAGES, FL, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Spruce Creek North 6533 SW 107TH PL, OCALA, FL, 34476, Ocala, FL 34476
$149,000

2 beds

|

2 baths

|

1,304 sq ft

|

House

6533 SW 107TH PL, OCALA, FL, 34476
Community: Spruce Creek North
New Kings Ridge 2012 BRAXTON ST, CLERMONT, FL, 34711, Clermont, FL 34711
$299,900

2 beds

|

2 baths

|

1,335 sq ft

|

House

2012 BRAXTON ST, CLERMONT, FL, 34711
Community: Kings Ridge
New Majestic Oaks Ocala 4311 SW 82ND LN, OCALA, FL, 34476, Ocala, FL 34476
$347,990

5 beds

|

3 baths

|

2,449 sq ft

|

House

4311 SW 82ND LN, OCALA, FL, 34476
Community: Majestic Oaks Ocala
New Pine Run Estates 10015 SW 90TH CT, OCALA, FL, 34481, Ocala, FL 34481
$144,777

2 beds

|

2 baths

|

1,144 sq ft

|

House

10015 SW 90TH CT, OCALA, FL, 34481
Community: Pine Run Estates
New Palm Cay 8424 SW 107TH PL, OCALA, FL, 34481, Ocala, FL 34481
$169,900

2 beds

|

2 baths

|

1,040 sq ft

|

House

8424 SW 107TH PL, OCALA, FL, 34481
Community: Palm Cay
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.
New Spruce Creek South 17830 SE 95TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$299,900

2 beds

|

2 baths

|

1,734 sq ft

|

House

17830 SE 95TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
New Cherrywood 10225 SW 61ST TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$224,900

3 beds

|

2 baths

|

1,482 sq ft

|

House

10225 SW 61ST TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
New Tohoqua Reserve 1873 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$365,000

3 beds

|

2 baths

|

1,559 sq ft

|

Villa

1873 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
New Stone Creek 9063 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$294,900

2 beds

|

2 baths

|

1,556 sq ft

|

Villa

9063 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
New Venetian Bay 3610 MARISOL CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$559,900

3 beds

|

2 baths

|

2,079 sq ft

|

House

3610 MARISOL CT, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Sun City Center 2039 BERRY ROBERTS DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$420,000

3 beds

|

2 baths

|

2,352 sq ft

|

House

2039 BERRY ROBERTS DR, SUN CITY CENTER, ...
Community: Sun City Center
New Legacy of Leesburg 5725 CELEBRATION WAY, LEESBURG, FL, 3474..., Leesburg, FL 34748
$345,000

3 beds

|

2 baths

|

1,732 sq ft

|

House

5725 CELEBRATION WAY, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
Highland Lakes 6022 WILANDER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$248,500

3 beds

|

2 baths

|

1,460 sq ft

|

House

6022 WILANDER ST, LEESBURG, FL, 34748
Community: Highland Lakes
New Bridgewater Landing 5714 STOCKPORT ST, RIVERVIEW, FL, 33578, Riverview, FL 33578
$350,000

2 beds

|

2 baths

|

1,516 sq ft

|

Villa

5714 STOCKPORT ST, RIVERVIEW, FL, 33578
Community: Bridgewater Landing
Highland Fairways 3658 HIGHLAND FAIRWAYS BLVD, LAKELAND, F..., Lakeland, FL 33810
$321,000

3 beds

|

2 baths

|

1,851 sq ft

|

House

3658 HIGHLAND FAIRWAYS BLVD, LAKELAND, F...
Community: Highland Fairways
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.
New The Villages® 2378 COLUMBIA WAY, THE VILLAGES, FL, 321..., The Villages, FL 32162
$550,000

4 beds

|

2 baths

|

2,202 sq ft

|

House

2378 COLUMBIA WAY, THE VILLAGES, FL, 321...
Community: The Villages®
New Legacy of Leesburg 27111 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,900

3 beds

|

2 baths

|

1,477 sq ft

|

House

27111 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
New Cresswind at Victoria Gardens 109 APREMONT CT, DELAND, FL, 32724, Deland, FL 32724
$385,000

3 beds

|

2 baths

|

1,836 sq ft

|

House

109 APREMONT CT, DELAND, FL, 32724
New Del Webb Sunbridge 2587 CLIFF WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$465,000

2 beds

|

2 baths

|

1,401 sq ft

|

House

2587 CLIFF WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
New Cherrywood 6136 SW 100TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$172,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

6136 SW 100TH LOOP, OCALA, FL, 34476
Community: Cherrywood
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 3818 ST EMMA CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$394,900

2 beds

|

2 baths

|

2,065 sq ft

|

House

3818 ST EMMA CT, LEESBURG, FL, 34748
New The Villages® 2423 DUNDEE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$350,000

3 beds

|

2 baths

|

1,397 sq ft

|

Villa

2423 DUNDEE TER, THE VILLAGES, FL, 32162
Community: The Villages®
Lake James 8107 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$370,000

2 beds

|

2 baths

|

1,557 sq ft

|

House

8107 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Spruce Creek Country Club 13544 SE 89TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$429,000

3 beds

|

2 baths

|

1,958 sq ft

|

House

13544 SE 89TH TERRACE RD, SUMMERFIELD, F...
New Plantation at Leesburg 4745 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$312,000

2 beds

|

4 baths

|

1,988 sq ft

|

House

4745 TARA VIEW RD, LEESBURG, FL, 34748

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3,573 homes near Winter Garden
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