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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!
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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
Plantation at Leesburg 25313 JASMINE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$265,000

2 beds

|

2 baths

|

1,718 sq ft

|

House

25313 JASMINE CT, LEESBURG, FL, 34748
Stonecrest 10882 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$369,000

3 beds

|

2 baths

|

1,616 sq ft

|

House

10882 SE 170TH LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
Venetian Bay 3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$479,000

3 beds

|

2 baths

|

2,174 sq ft

|

House

3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Highlands Ridge 2704 E WATERVIEW DR, AVON PARK, FL, 3382..., Avon Park, FL 33825
$94,900

3 beds

|

2 baths

|

1,700 sq ft

|

Mobile Home

2704 E WATERVIEW DR, AVON PARK, FL, 3382...
Community: Highlands Ridge
Solivita 346 TREVISO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$669,000

3 beds

|

3 baths

|

2,871 sq ft

|

House

346 TREVISO DR, 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 555 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$299,900

3 beds

|

2 baths

|

1,610 sq ft

|

House

555 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
On Top of the World 8876 SW 95TH LN E, OCALA, FL, 34481, Ocala, FL 34481
$200,000

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

8876 SW 95TH LN E, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9691 SW 95TH CT A, OCALA, FL, 34481, Ocala, FL 34481
$185,000

2 beds

|

2 baths

|

1,502 sq ft

|

Condo

9691 SW 95TH CT A, OCALA, FL, 34481
Community: On Top of the World
Harbor Hills Country Club 5252 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$383,000

3 beds

|

2 baths

|

1,844 sq ft

|

House

5252 GROVE MNR, LADY LAKE, FL, 32159
The Villages® 1042 AVENIDA SONOMA, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$475,000

3 beds

|

3 baths

|

2,271 sq ft

|

House

1042 AVENIDA SONOMA, LADY LAKE, FL, 3215...
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.
Spruce Creek South 10677 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$214,900

2 beds

|

2 baths

|

1,008 sq ft

|

House

10677 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
Sun City Center 2410 LANCASTER DR NA, SUN CITY CENTER, F..., Sun City Center, FL 33573
$199,999

2 beds

|

2 baths

|

1,579 sq ft

|

Condo

2410 LANCASTER DR NA, SUN CITY CENTER, F...
Community: Sun City Center
Ocala Palms 5064 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482
$209,000

2 beds

|

2 baths

|

1,142 sq ft

|

House

5064 NW 18TH ST, OCALA, FL, 34482
Community: Ocala Palms
Heritage - The Cottages of Sanders Grove 28026 CYPRESS SPRINGS LOOP, OKAHUMPKA, F..., Okahumpka, FL 34762
$293,000

4 beds

|

2 baths

|

1,617 sq ft

|

House

28026 CYPRESS SPRINGS LOOP, OKAHUMPKA, F...
The Villages® 2123 HEATHER HILL LOOP, THE VILLAGES, FL..., The Villages, FL 32162
$379,900

3 beds

|

2 baths

|

1,565 sq ft

|

House

2123 HEATHER HILL LOOP, 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
Sun City Center 310 KELSEY WAY, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$150,000

2 beds

|

2 baths

|

1,073 sq ft

|

Condo

310 KELSEY WAY, SUN CITY CENTER, FL, 335...
Community: Sun City Center
The Villages® 4406 CREIGHTON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163
$799,900

3 beds

|

2 baths

|

2,061 sq ft

|

House

4406 CREIGHTON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Sun City Center 301 ANDOVER PL S APT 177, SUN CITY CENTE..., Sun City Center, FL 33573
$129,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

301 ANDOVER PL S APT 177, SUN CITY CENTE...
Community: Sun City Center
On Top of the World 8650 SW 83RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$368,000

2 beds

|

2 baths

|

2,425 sq ft

|

House

8650 SW 83RD LOOP, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 2429 NEW HAVEN CIR # 64, SUN CITY CENTER..., Sun City Center, FL 33573
$188,000

2 beds

|

2 baths

|

1,359 sq ft

|

Condo

2429 NEW HAVEN CIR # 64, SUN CITY CENTER...
Community: Sun City Center
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.
Stonecrest 17867 SE 115TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$335,000

3 beds

|

2 baths

|

1,597 sq ft

|

House

17867 SE 115TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 445 SOCIETY HILL CIR, THE VILLAGES, FL, ..., The Villages, FL 32162
$730,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

445 SOCIETY HILL CIR, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 278 MATISSE AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$459,900

3 beds

|

2 baths

|

1,966 sq ft

|

House

278 MATISSE AVE, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 1803 PACIFIC DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$379,900

2 beds

|

2 baths

|

1,733 sq ft

|

House

1803 PACIFIC DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Spruce Creek Country Club 9029 SE 130TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$450,000

3 beds

|

3 baths

|

2,809 sq ft

|

House

9029 SE 130TH LOOP, SUMMERFIELD, FL, 344...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Kings Ridge 4021 NEWLAND ST, CLERMONT, FL, 34711, Clermont, FL 34711
$399,900

2 beds

|

2 baths

|

2,124 sq ft

|

House

4021 NEWLAND ST, CLERMONT, FL, 34711
Community: Kings Ridge
Ocala Palms 5192 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482
$250,000

2 beds

|

2 baths

|

1,457 sq ft

|

House

5192 NW 18TH ST, OCALA, FL, 34482
Community: Ocala Palms
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®
Plantation at Leesburg 25333 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$265,000

3 beds

|

2 baths

|

1,737 sq ft

|

House

25333 RIVER CREST DR, LEESBURG, FL, 3474...
Majestic Oaks Ocala 5661 SW 88TH PL, OCALA, FL, 34476, Ocala, FL 34476
$289,000

3 beds

|

2 baths

|

1,830 sq ft

|

House

5661 SW 88TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
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.
On Top of the World 9661 SW 95TH CT B, OCALA, FL, 34481, Ocala, FL 34481
$215,000

2 beds

|

2 baths

|

1,412 sq ft

|

Condo

9661 SW 95TH CT B, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 10406 SW 96TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$265,000

2 beds

|

2 baths

|

1,432 sq ft

|

House

10406 SW 96TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 2226 NOTTINGHAM GREENS DR, SUN CITY CENT..., Sun City Center, FL 33573
$343,900

2 beds

|

2 baths

|

1,668 sq ft

|

Villa

2226 NOTTINGHAM GREENS DR, SUN CITY CENT...
Community: Sun City Center
Summit Greens 2495 SQUAW CRK, CLERMONT, FL, 34711, Clermont, FL 34711
$550,000

3 beds

|

3 baths

|

2,817 sq ft

|

House

2495 SQUAW CRK, CLERMONT, FL, 34711
Community: Summit Greens
Solivita 151 BELL TOWER XING W, KISSIMMEE, FL, 34..., Kissimmee, FL 34759
$234,900

2 beds

|

2 baths

|

1,356 sq ft

|

House

151 BELL TOWER XING W, KISSIMMEE, FL, 34...
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Country Club of Mount Dora 1521 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$688,850

3 beds

|

3 baths

|

3,028 sq ft

|

House

1521 EDGEWATER DR, MOUNT DORA, FL, 32757
Stone Creek 9777 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$539,900

3 beds

|

3 baths

|

2,501 sq ft

|

House

9777 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
Thunderbird Hill 3745 CAMRY CT, SEBRING, FL, 33872, Sebring, FL 33872
$199,000

2 beds

|

2 baths

|

950 sq ft

|

Villa

3745 CAMRY CT, SEBRING, FL, 33872
Community: Thunderbird Hill
Sun City Center 206 SOLA LN, SUN CITY CENTER, FL, 33573, Sun City Center, FL 33573
$250,000

2 beds

|

2 baths

|

1,516 sq ft

|

House

206 SOLA LN, SUN CITY CENTER, FL, 33573
Community: Sun City Center
Stone Creek 9119 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$294,492

2 beds

|

2 baths

|

1,437 sq ft

|

House

9119 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek

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3,648 homes near Winter Garden
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