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

3,648 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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 - $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
$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) VillageWalk at Lake Nona
$300Ks - $1Ms
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
<$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
$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
4.4 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
Latitude Margaritaville 923 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$470,000

3 beds

|

2 baths

|

1,862 sq ft

|

House

923 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Spruce Creek South 17874 SE 105TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$178,000

2 beds

|

2 baths

|

936 sq ft

|

House

17874 SE 105TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
New Solivita 328 INDIAN WELLS AVE, POINCIANA, FL, 347..., Poinciana, FL 34759
$325,000

2 beds

|

2 baths

|

1,548 sq ft

|

House

328 INDIAN WELLS AVE, POINCIANA, FL, 347...
Community: Solivita
Lake Jovita Golf and Country Club 13915 CARRYBACK DR, DADE CITY, FL, 33525, Dade City, FL 33525
$1,295,000

4 beds

|

3 baths

|

3,613 sq ft

|

House

13915 CARRYBACK DR, DADE CITY, FL, 33525
Stone Creek 6683 SW 97TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$469,900

3 beds

|

2 baths

|

1,958 sq ft

|

House

6683 SW 97TH TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 3362 GALLIA ST, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$364,000

3 beds

|

2 baths

|

1,476 sq ft

|

House

3362 GALLIA ST, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
The Villages® 482 HILDALGO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$212,900

1 beds

|

1 baths

|

810 sq ft

|

Villa

482 HILDALGO DR, THE VILLAGES, FL, 32159
Community: The Villages®
Majestic Oaks Ocala 8895 SW 57TH COURT RD, OCALA, FL, 34476, Ocala, FL 34476
$308,800

3 beds

|

2 baths

|

1,864 sq ft

|

House

8895 SW 57TH COURT RD, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Heritage Hills 3524 LITCHFIELD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$495,000

4 beds

|

3 baths

|

2,293 sq ft

|

House

3524 LITCHFIELD CT, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 1114 PARADISE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$255,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

1114 PARADISE DR, LADY LAKE, 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.
Venetian Bay 236 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$425,000

3 beds

|

2 baths

|

1,610 sq ft

|

House

236 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
The Villages® 3472 SIPSEY ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$339,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

3472 SIPSEY ST, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 3467 SIPSEY ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$299,000

3 beds

|

2 baths

|

1,240 sq ft

|

House

3467 SIPSEY ST, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 8681 SW 93RD PL B, OCALA, FL, 34481, Ocala, FL 34481
$192,000

2 beds

|

2 baths

|

1,409 sq ft

|

Villa

8681 SW 93RD PL B, OCALA, FL, 34481
Community: On Top of the World
Plantation at Leesburg 24841 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$169,000

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

24841 PINE HL, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Heritage Hills 3606 SOLANA CIR, CLERMONT, FL, 34711, Clermont, FL 34711
$424,900

3 beds

|

3 baths

|

2,006 sq ft

|

House

3606 SOLANA CIR, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 1649 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$259,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1649 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
Stone Creek 8464 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$375,000

3 beds

|

2 baths

|

1,663 sq ft

|

House

8464 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
Esplanade at Wiregrass Ranch 4639 GAROFALO RD, WESLEY CHAPEL, FL, 335..., Wesley Chapel, FL 33543
$415,000

2 beds

|

2 baths

|

1,689 sq ft

|

House

4639 GAROFALO RD, WESLEY CHAPEL, FL, 335...
New Latitude Margaritaville 850 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$915,000

3 beds

|

3 baths

|

2,336 sq ft

|

House

850 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
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 Preserve 14272 SW 112TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$269,000

3 beds

|

2 baths

|

1,790 sq ft

|

House

14272 SW 112TH CIR, DUNNELLON, FL, 34432
The Villages® 3331 OVERLAND TER, THE VILLAGES, FL, 321..., The Villages, FL 32163
$379,000

2 beds

|

2 baths

|

1,161 sq ft

|

Villa

3331 OVERLAND TER, THE VILLAGES, FL, 321...
Community: The Villages®
Del Webb Minneola 2766 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715
$479,990

2 beds

|

2 baths

|

1,561 sq ft

|

House

2766 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
New Summer Trees 109 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$274,809

2 beds

|

2 baths

|

1,403 sq ft

|

House

109 UNDERBRUSH TRL, PORT ORANGE, FL, 321...
Community: Summer Trees
New Plantation at Leesburg 24547 BOCAGE WAY, LEESBURG, FL, 34748, Leesburg, FL 34748
$435,000

2 beds

|

3 baths

|

2,597 sq ft

|

House

24547 BOCAGE WAY, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Arlington Ridge 26694 OTTER CREEK LN, LEESBURG, FL, 3474..., Leesburg, FL 34748
$499,000

3 beds

|

3 baths

|

2,399 sq ft

|

House

26694 OTTER CREEK LN, LEESBURG, FL, 3474...
Community: Arlington Ridge
Solivita 627 VINEYARD WAY, POINCIANA, FL, 34759, Poinciana, FL 34759
$231,700

2 beds

|

2 baths

|

1,071 sq ft

|

House

627 VINEYARD WAY, POINCIANA, FL, 34759
Community: Solivita
The Villages® 600 OAK BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$155,000

2 beds

|

2 baths

|

1,288 sq ft

|

Manufactured Home

600 OAK BLVD, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 116 CYPRESS RD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$74,500

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

116 CYPRESS RD, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 1765 W SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$139,900

2 beds

|

2 baths

|

1,309 sq ft

|

Manufactured Home

1765 W SCHWARTZ BLVD, LADY LAKE, FL, 321...
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.
SummerGlen 15092 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$369,900

3 beds

|

2 baths

|

2,285 sq ft

|

House

15092 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
The Villages® 1676 VAN BUREN WAY, THE VILLAGES, FL, 32..., The Villages, FL 32162
$424,900

3 beds

|

2 baths

|

1,840 sq ft

|

House

1676 VAN BUREN WAY, THE VILLAGES, FL, 32...
Community: The Villages®
Lake Jovita Golf and Country Club 12713 GRAND TRAVERSE DR, DADE CITY, FL, ..., Dade City, FL 33525
$849,000

4 beds

|

3 baths

|

3,121 sq ft

|

House

12713 GRAND TRAVERSE DR, DADE CITY, FL, ...
Marion Landing 6366 SW 84TH LN, OCALA, FL, 34476, Ocala, FL 34476
$125,000

2 beds

|

2 baths

|

1,240 sq ft

|

Manufactured Home

6366 SW 84TH LN, OCALA, FL, 34476
Community: Marion Landing
Solivita 504 MILLIFIORA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$245,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

504 MILLIFIORA LN, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 157 SAND PIPER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$350,000

3 beds

|

3 baths

|

2,267 sq ft

|

House

157 SAND PIPER DR, KISSIMMEE, FL, 34759
Community: Solivita
Latitude Margaritaville 500 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$415,000

2 beds

|

2 baths

|

1,464 sq ft

|

House

500 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
New Summer Trees 103 LAZY FOX LAIR, PORT ORANGE, FL, 3212..., Port Orange, FL 32128
$284,902

2 beds

|

2 baths

|

1,404 sq ft

|

House

103 LAZY FOX LAIR, PORT ORANGE, FL, 3212...
Community: Summer Trees
On Top of the World 7935 SW 89TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$275,000

2 beds

|

2 baths

|

1,344 sq ft

|

House

7935 SW 89TH LOOP, OCALA, FL, 34476
Community: On Top of the World
Pine Run Estates 9430 SW 102ND PL, OCALA, FL, 34481, Ocala, FL 34481
$145,000

2 beds

|

2 baths

|

1,040 sq ft

|

House

9430 SW 102ND PL, OCALA, FL, 34481
Community: Pine Run Estates

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3,648 homes near Winter Garden
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