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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
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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) 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
Lakes at Laurel Highlands 2719 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$330,000

4 beds

|

2 baths

|

1,867 sq ft

|

House

2719 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Southshore Bay 17253 STAR BANKS ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$394,000

2 beds

|

2 baths

|

1,956 sq ft

|

House

17253 STAR BANKS ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Ocala Preserve 5662 NW 40TH PL, OCALA, FL, 34482, Ocala, FL 34482
$379,000

3 beds

|

2 baths

|

1,862 sq ft

|

House

5662 NW 40TH PL, OCALA, FL, 34482
Community: Ocala Preserve
Latitude Margaritaville 710 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$559,900

2 beds

|

3 baths

|

1,743 sq ft

|

House

710 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 213 CHEESEBURGER DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$529,900

2 beds

|

2 baths

|

1,681 sq ft

|

House

213 CHEESEBURGER DR, DAYTONA BEACH, FL, ...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Breakaway Trails 45 WINDING CREEK WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$629,900

3 beds

|

2 baths

|

2,366 sq ft

|

House

45 WINDING CREEK WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
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 9012 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$179,800

2 beds

|

2 baths

|

1,777 sq ft

|

House

9012 SW 91ST CIR, OCALA, FL, 34481
Community: On Top of the World
Arlington Ridge 26689 OTTER CREEK LN, LEESBURG, FL, 3474..., Leesburg, FL 34748
$399,000

3 beds

|

2 baths

|

1,725 sq ft

|

House

26689 OTTER CREEK LN, LEESBURG, FL, 3474...
Community: Arlington Ridge
The Villages® 144 COSTA MESA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$354,900

3 beds

|

2 baths

|

2,046 sq ft

|

House

144 COSTA MESA 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.
The Villages® 1524 CONWAY CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$334,900

2 beds

|

2 baths

|

1,196 sq ft

|

House

1524 CONWAY CT, THE VILLAGES, FL, 32162
Community: The Villages®
Stonecrest 11193 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$344,900

3 beds

|

2 baths

|

1,974 sq ft

|

House

11193 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Pennbrooke Fairways 231 BENTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$209,247

2 beds

|

2 baths

|

1,423 sq ft

|

House

231 BENTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Tampa Bay Golf and Country Club 9723 ROLLING CIR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$419,500

3 beds

|

2 baths

|

1,892 sq ft

|

House

9723 ROLLING CIR, SAN ANTONIO, FL, 33576
Pennbrooke Fairways 409 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$214,247

2 beds

|

2 baths

|

1,232 sq ft

|

House

409 WESTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 623 DELGADO AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$305,000

2 beds

|

2 baths

|

1,206 sq ft

|

Villa

623 DELGADO AVE, THE VILLAGES, FL, 32159
Community: The Villages®
Carillon Lakes 4344 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811
$657,000

5 beds

|

4 baths

|

3,461 sq ft

|

House

4344 WHISTLEWOOD CIR, LAKELAND, FL, 3381...
Community: Carillon Lakes
Sullivan Ranch 30304 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$545,000

6 beds

|

4 baths

|

3,499 sq ft

|

House

30304 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Twin Lakes 2606 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$559,990

3 beds

|

3 baths

|

2,365 sq ft

|

House

2606 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Solivita 561 LAGO MATISSE ST, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$440,000

3 beds

|

2 baths

|

1,815 sq ft

|

House

561 LAGO MATISSE ST, KISSIMMEE, FL, 3475...
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.
Solivita 651 HIGHLANDS HAMMOCK DR, POINCIANA, FL,..., Poinciana, FL 34759
$299,900

2 beds

|

3 baths

|

1,800 sq ft

|

House

651 HIGHLANDS HAMMOCK DR, POINCIANA, FL,...
Community: Solivita
Solivita 3390 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$273,000

2 beds

|

2 baths

|

1,353 sq ft

|

Villa

3390 FALLBROOK DR, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 542 VITERRA CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$463,000

3 beds

|

3 baths

|

2,312 sq ft

|

House

542 VITERRA CT, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 560 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$274,900

2 beds

|

2 baths

|

1,543 sq ft

|

House

560 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
On Top of the World 8747 SW 98TH STREET RD F, OCALA, FL, 344..., Ocala, FL 34481
$144,900

2 beds

|

2 baths

|

1,198 sq ft

|

Villa

8747 SW 98TH STREET RD F, OCALA, FL, 344...
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Highlands 22125 DRAW BRIDGE DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$377,000

3 beds

|

2 baths

|

2,200 sq ft

|

House

22125 DRAW BRIDGE DR, LEESBURG, FL, 3474...
Community: Royal Highlands
The Villages® 939 KOLLER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$479,900

3 beds

|

2 baths

|

1,880 sq ft

|

House

939 KOLLER CT, THE VILLAGES, FL, 32163
Community: The Villages®
Lake Jovita Golf and Country Club 12717 EASTPOINTE DR, DADE CITY, FL, 3352..., Dade City, FL 33525
$424,900

4 beds

|

2 baths

|

2,057 sq ft

|

House

12717 EASTPOINTE DR, DADE CITY, FL, 3352...
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
Foxwood Lake Estates 1620 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$219,000

3 beds

|

2 baths

|

1,800 sq ft

|

Manufactured Home

1620 FOXWAY DR, LAKELAND, FL, 33810
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.
Royal Highlands 5518 QUEEN VICTORIA DR, LEESBURG, FL, 34..., Leesburg, FL 34748
$315,000

3 beds

|

2 baths

|

1,757 sq ft

|

House

5518 QUEEN VICTORIA DR, LEESBURG, FL, 34...
Community: Royal Highlands
Sun City Center 1906 CANTERBURY LN 20, SUN CITY CENTER, ..., Sun City Center, FL 33573
$159,000

2 beds

|

2 baths

|

984 sq ft

|

Condo

1906 CANTERBURY LN 20, SUN CITY CENTER, ...
Community: Sun City Center
Breakaway Trails 9 FOREST VIEW WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$969,999

5 beds

|

5 baths

|

4,840 sq ft

|

House

9 FOREST VIEW WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
The Villages® 3389 LUTY LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$375,000

3 beds

|

2 baths

|

1,547 sq ft

|

House

3389 LUTY LN, THE VILLAGES, FL, 32163
Community: The Villages®
Sun City Center 1902 ANDOVER ST 198, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$141,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

1902 ANDOVER ST 198, 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
The Villages® 17096 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162
$315,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

17096 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
Sun City Center 804 REGAL MANOR WAY, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$375,000

2 beds

|

2 baths

|

1,808 sq ft

|

House

804 REGAL MANOR WAY, SUN CITY CENTER, FL...
Community: Sun City Center
Sun City Center 657 MASTERPIECE DR # 154, SUN CITY CENTE..., Sun City Center, FL 33573
$234,000

2 beds

|

2 baths

|

1,543 sq ft

|

Condo

657 MASTERPIECE DR # 154, SUN CITY CENTE...
Community: Sun City Center
Spruce Creek South 10689 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$229,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

10689 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
Stonecrest 17414 SE 123RD TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$389,000

3 beds

|

2 baths

|

1,914 sq ft

|

House

17414 SE 123RD TER, SUMMERFIELD, FL, 344...
Community: Stonecrest

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3,648 homes near Winter Garden
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