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

3,631 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 - $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 (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
$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
$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
$200Ks - $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 - $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 - $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
The Villages® 17602 SE 82ND WOODLAWN AVE, THE VILLAGES..., The Villages, FL 32162
$465,999

3 beds

|

2 baths

|

1,924 sq ft

|

House

17602 SE 82ND WOODLAWN AVE, THE VILLAGES...
Community: The Villages®
Solivita 915 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$590,000

4 beds

|

3 baths

|

3,110 sq ft

|

House

915 SAN RAPHAEL ST, POINCIANA, FL, 34759
Community: Solivita
New Sun City Center 653 MCDANIEL ST # 178, SUN CITY CENTER, ..., Sun City Center, FL 33573
$212,000

2 beds

|

2 baths

|

1,277 sq ft

|

Condo

653 MCDANIEL ST # 178, SUN CITY CENTER, ...
Community: Sun City Center
Latitude Margaritaville 338 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$650,000

3 beds

|

3 baths

|

2,402 sq ft

|

House

338 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
New Majestic Oaks Ocala 8835 SW 52ND CT, OCALA, FL, 34476, Ocala, FL 34476
$345,000

3 beds

|

2 baths

|

1,729 sq ft

|

House

8835 SW 52ND CT, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 16946 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162
$442,000

3 beds

|

2 baths

|

2,002 sq ft

|

House

16946 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
The Villages® 937 KAUSKA WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$385,000

3 beds

|

2 baths

|

1,558 sq ft

|

House

937 KAUSKA WAY, THE VILLAGES, FL, 32163
Community: The Villages®
Lake James 8147 LAKE JAMES DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$385,000

2 beds

|

2 baths

|

1,476 sq ft

|

House

8147 LAKE JAMES DR, LAKELAND, FL, 33810
Community: Lake James
New Lake Ashton 4111 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$324,900

2 beds

|

2 baths

|

1,688 sq ft

|

House

4111 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
Venetian Bay 661 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$723,006

4 beds

|

3 baths

|

2,748 sq ft

|

House

661 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
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 Country Club 9126 SE 125TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$389,000

2 beds

|

2 baths

|

1,757 sq ft

|

House

9126 SE 125TH LOOP, SUMMERFIELD, FL, 344...
Sun City Center 382 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$184,990

2 beds

|

2 baths

|

1,516 sq ft

|

Condo

382 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Pine Run Estates 9070 SW 101ST LN, OCALA, FL, 34481, Ocala, FL 34481
$134,900

2 beds

|

1 baths

|

864 sq ft

|

House

9070 SW 101ST LN, OCALA, FL, 34481
Community: Pine Run Estates
Highland Lakes 26126 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,900

3 beds

|

2 baths

|

1,890 sq ft

|

House

26126 NEWCOMBE CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Lake Jovita Golf and Country Club 12632 OAK HOLLOW CT, DADE CITY, FL, 3352..., Dade City, FL 33525
$799,900

4 beds

|

4 baths

|

2,711 sq ft

|

House

12632 OAK HOLLOW CT, DADE CITY, FL, 3352...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8580 SW 97TH LANE RD D, OCALA, FL, 34481, Ocala, FL 34481
$135,000

2 beds

|

2 baths

|

1,196 sq ft

|

Villa

8580 SW 97TH LANE RD D, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9155 SW 83RD CT C, OCALA, FL, 34481, Ocala, FL 34481
$250,000

2 beds

|

2 baths

|

1,886 sq ft

|

Villa

9155 SW 83RD CT C, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8702 SW 93RD LN D, OCALA, FL, 34481, Ocala, FL 34481
$159,900

2 beds

|

2 baths

|

1,531 sq ft

|

Villa

8702 SW 93RD LN D, OCALA, FL, 34481
Community: On Top of the World
The Lakes at Harmony 7520 CASTLEWOOD CT, HARMONY, FL, 34773, Harmony, FL 34773
$401,990

2 beds

|

2 baths

|

1,455 sq ft

|

House

7520 CASTLEWOOD CT, HARMONY, FL, 34773
Legacy of Leesburg 5401 WATER LILY CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$395,000

3 beds

|

2 baths

|

2,033 sq ft

|

House

5401 WATER LILY CT, LEESBURG, FL, 34748
Community: Legacy of Leesburg
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 On Top of the World 10325 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481
$430,000

3 beds

|

3 baths

|

2,536 sq ft

|

House

10325 SW 105TH CT, OCALA, FL, 34481
Community: On Top of the World
New On Top of the World 10373 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481
$449,000

2 beds

|

3 baths

|

2,493 sq ft

|

House

10373 SW 105TH CT, OCALA, FL, 34481
Community: On Top of the World
New Del Webb Orlando 333 ALMANSA ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$359,000

2 beds

|

2 baths

|

1,655 sq ft

|

House

333 ALMANSA ST, DAVENPORT, FL, 33837
Community: Del Webb Orlando
On Top of the World 7980 SW 89TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$267,000

2 beds

|

2 baths

|

1,226 sq ft

|

House

7980 SW 89TH CIR, OCALA, FL, 34481
Community: On Top of the World
JB Ranch 6125 SW 88TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$334,900

2 beds

|

2 baths

|

1,813 sq ft

|

House

6125 SW 88TH LOOP, OCALA, FL, 34476
Community: JB Ranch
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 25034 BETTON HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$145,000

3 beds

|

2 baths

|

1,456 sq ft

|

Manufactured Home

25034 BETTON HL, LEESBURG, FL, 34748
On Top of the World 9275 SW 97TH LN B, OCALA, FL, 34481, Ocala, FL 34481
$210,000

2 beds

|

2 baths

|

1,470 sq ft

|

Villa

9275 SW 97TH LN B, OCALA, FL, 34481
Community: On Top of the World
Pennbrooke Fairways 32218 SWEET BRIAR CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$239,900

2 beds

|

2 baths

|

1,272 sq ft

|

House

32218 SWEET BRIAR CT, LEESBURG, FL, 3474...
Community: Pennbrooke Fairways
The Villages® 1868 DALTON DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$495,000

3 beds

|

2 baths

|

1,757 sq ft

|

Villa

1868 DALTON DR, THE VILLAGES, FL, 32162
Community: The Villages®
Pennbrooke Fairways 32805 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$256,000

3 beds

|

2 baths

|

1,685 sq ft

|

House

32805 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke 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 Sun City Center 930 KINGS BLVD # 930, SUN CITY CENTER, F..., Sun City Center, FL 33573
$360,000

2 beds

|

2 baths

|

1,720 sq ft

|

Condo

930 KINGS BLVD # 930, SUN CITY CENTER, F...
Community: Sun City Center
Spruce Creek Country Club 11759 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$375,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

11759 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Cherrywood 9849 SW 61ST CT, OCALA, FL, 34476, Ocala, FL 34476
$222,500

3 beds

|

2 baths

|

1,503 sq ft

|

House

9849 SW 61ST CT, OCALA, FL, 34476
Community: Cherrywood
Sun City Center 1503 LAUGHTON PL 206, SUN CITY CENTER, F..., Sun City Center, FL 33573
$234,000

2 beds

|

2 baths

|

1,751 sq ft

|

Condo

1503 LAUGHTON PL 206, SUN CITY CENTER, F...
Community: Sun City Center
Ocala Preserve 5231 NW 48TH PL, OCALA, FL, 34482, Ocala, FL 34482
$259,000

2 beds

|

2 baths

|

1,552 sq ft

|

House

5231 NW 48TH PL, OCALA, FL, 34482
Community: Ocala Preserve
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 9511 SE 168TH ELDERBERRY PL, THE VILLAGE..., The Villages, FL 32162
$284,000

2 beds

|

2 baths

|

1,388 sq ft

|

House

9511 SE 168TH ELDERBERRY PL, THE VILLAGE...
Community: The Villages®
Sandpiper Golf & Country Club 669 EAGLE RUN, LAKELAND, FL, 33809, Lakeland, FL 33809
$339,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

669 EAGLE RUN, LAKELAND, FL, 33809
Spruce Creek Country Club 9025 SE 136TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$360,000

3 beds

|

2 baths

|

2,251 sq ft

|

House

9025 SE 136TH LOOP, SUMMERFIELD, FL, 344...
The Villages® 852 SAPPHIRE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$360,000

3 beds

|

2 baths

|

1,407 sq ft

|

Villa

852 SAPPHIRE PL, THE VILLAGES, FL, 32163
Community: The Villages®
High Vista at Ridgewood Lakes 116 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$324,000

2 beds

|

2 baths

|

1,776 sq ft

|

House

116 FLEMING LN, DAVENPORT, FL, 33837

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3,631 homes near Winter Garden
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