Call us at (689) 407-5757 to learn more about active adult communities in Winter Garden

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

3,964 homes near Winter Garden

Sort by:

Relevance

Relevance

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 - $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
<$100k - $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
$200Ks - $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 - $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 - $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 - $600Ks
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 - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $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
$200Ks - $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 - $900Ks
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
$200Ks - $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 - $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
$100Ks - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$100Ks - $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
$300Ks - $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 - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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 - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
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 - $800Ks
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
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$400Ks - $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 - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Pelican Bay Daytona Beach 128 LAUGHING GULL CT, DAYTONA BEACH, FL,..., Daytona Beach, FL 32119
$285,000

2 beds

|

2 baths

|

1,408 sq ft

|

Townhouse

128 LAUGHING GULL CT, DAYTONA BEACH, FL,...
Pelican Bay Daytona Beach 444 SEA DUCK DR, DAYTONA BEACH, FL, 3211..., Daytona Beach, FL 32119
$670,000

5 beds

|

3 baths

|

4,058 sq ft

|

House

444 SEA DUCK DR, DAYTONA BEACH, FL, 3211...
Latitude Margaritaville 258 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$374,900

2 beds

|

2 baths

|

1,909 sq ft

|

House

258 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
The Villages® 1781 KINGFISHER CT, THE VILLAGES, FL, 32..., The Villages, FL 32162
$554,900

3 beds

|

2 baths

|

1,612 sq ft

|

Villa

1781 KINGFISHER CT, THE VILLAGES, FL, 32...
Community: The Villages®
On Top of the World 8533 SW 93RD PL C, OCALA, FL, 34481, Ocala, FL 34481
$135,000

2 beds

|

2 baths

|

1,531 sq ft

|

Villa

8533 SW 93RD PL C, OCALA, FL, 34481
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
Latitude Margaritaville 786 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$729,900

3 beds

|

3 baths

|

2,392 sq ft

|

House

786 JOLLYMON WAY, DAYTONA BEACH, FL, 321...
The Villages® 1787 FOLIAGE LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$390,000

2 beds

|

2 baths

|

1,132 sq ft

|

Villa

1787 FOLIAGE LN, THE VILLAGES, FL, 32162
Community: The Villages®
Stone Creek 9777 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$599,000

3 beds

|

3 baths

|

2,501 sq ft

|

House

9777 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 10075 SW 91ST PL, OCALA, FL, 34481, Ocala, FL 34481
$279,900

2 beds

|

2 baths

|

1,766 sq ft

|

House

10075 SW 91ST PL, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 1604 COMFY CT, SUN CITY CENTER, FL, 3357..., Sun City Center, FL 33573
$270,000

2 beds

|

2 baths

|

1,503 sq ft

|

House

1604 COMFY CT, SUN CITY CENTER, FL, 3357...
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.
Latitude Margaritaville 834 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$639,900

2 beds

|

3 baths

|

2,080 sq ft

|

House

834 JOLLYMON WAY, DAYTONA BEACH, FL, 321...
The Villages® 3557 COCHRAN ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$300,000

2 beds

|

2 baths

|

1,227 sq ft

|

House

3557 COCHRAN ST, THE VILLAGES, FL, 32163
Community: The Villages®
Ocala Palms 2045 NW 56TH TER, OCALA, FL, 34482, Ocala, FL 34482
$295,000

3 beds

|

2 baths

|

1,680 sq ft

|

House

2045 NW 56TH TER, OCALA, FL, 34482
Community: Ocala Palms
Latitude Margaritaville 300 BLUE STARFISH PL, DAYTONA BEACH, FL,..., Daytona Beach, FL 32124
$790,000

3 beds

|

3 baths

|

2,394 sq ft

|

House

300 BLUE STARFISH PL, DAYTONA BEACH, FL,...
Mirada 31371 CABANA RYE AVE, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$291,900

2 beds

|

2 baths

|

1,616 sq ft

|

Villa

31371 CABANA RYE AVE, SAN ANTONIO, FL, 3...
Community: Mirada
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2202 KERSHAW RD, THE VILLAGES, FL, 32162, The Villages, FL 32162
$429,900

3 beds

|

2 baths

|

1,927 sq ft

|

House

2202 KERSHAW RD, THE VILLAGES, FL, 32162
Community: The Villages®
Spruce Creek Country Club 11977 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$315,000

3 beds

|

2 baths

|

1,720 sq ft

|

House

11977 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Solivita 321 DAVINCI PASS, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$270,000

2 beds

|

2 baths

|

1,491 sq ft

|

House

321 DAVINCI PASS, KISSIMMEE, FL, 34759
Community: Solivita
On Top of the World 10145 SW 89TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$394,999

2 beds

|

2 baths

|

2,079 sq ft

|

House

10145 SW 89TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Gatherings of Lake Nona 7573 LAUREATE BLVD UNIT 1404, ORLANDO, F..., Orlando, FL 32827
$467,000

2 beds

|

2 baths

|

1,486 sq ft

|

Condo

7573 LAUREATE BLVD UNIT 1404, ORLANDO, F...
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 11276 SE 170TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$399,950

3 beds

|

2 baths

|

2,000 sq ft

|

House

11276 SE 170TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Four Seasons at Orlando 2051 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$514,990

3 beds

|

2 baths

|

1,968 sq ft

|

House

2051 FLORA PASS PL, KISSIMMEE, FL, 34747
Sun City Center 703 ELKHORN RD, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$300,000

2 beds

|

2 baths

|

1,907 sq ft

|

House

703 ELKHORN RD, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Pine Run Estates 10250 SW 92ND AVE, OCALA, FL, 34481, Ocala, FL 34481
$110,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

10250 SW 92ND AVE, OCALA, FL, 34481
Community: Pine Run Estates
Sullivan Ranch 30439 GIDRAN TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$499,000

4 beds

|

3 baths

|

2,838 sq ft

|

House

30439 GIDRAN TER, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8645 SW 94TH LN E, OCALA, FL, 34481, Ocala, FL 34481
$210,000

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

8645 SW 94TH LN E, OCALA, FL, 34481
Community: On Top of the World
Four Seasons at Orlando 2017 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$481,000

3 beds

|

2 baths

|

2,202 sq ft

|

House

2017 FLORA PASS PL, KISSIMMEE, FL, 34747
Sun City Center 1530 INGRAM DR # 1530, SUN CITY CENTER, ..., Sun City Center, FL 33573
$212,490

2 beds

|

2 baths

|

1,642 sq ft

|

Condo

1530 INGRAM DR # 1530, SUN CITY CENTER, ...
Community: Sun City Center
Spruce Creek Country Club 13165 SE 93RD CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$439,000

3 beds

|

3 baths

|

2,261 sq ft

|

House

13165 SE 93RD CIR, SUMMERFIELD, FL, 3449...
On Top of the World 6203 SW 93RD LOOP, OCALA, FL, 34476, Ocala, FL 34476
$320,000

4 beds

|

2 baths

|

2,034 sq ft

|

House

6203 SW 93RD LOOP, OCALA, FL, 34476
Community: On Top of the World
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 8601 SE 133RD ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$263,500

2 beds

|

2 baths

|

1,346 sq ft

|

House

8601 SE 133RD ST, SUMMERFIELD, FL, 34491
Sun City Center 1405 W DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$399,900

2 beds

|

2 baths

|

1,424 sq ft

|

House

1405 W DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Solivita 433 VIA ABRUZZI ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$608,000

3 beds

|

3 baths

|

2,400 sq ft

|

House

433 VIA ABRUZZI ST, KISSIMMEE, FL, 34759
Community: Solivita
Oak Run 8107 SW 108TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$211,000

2 beds

|

2 baths

|

1,160 sq ft

|

House

8107 SW 108TH PLACE RD, OCALA, FL, 34481
Community: Oak Run
Spruce Creek Country Club 13190 SE 93RD CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$389,000

2 beds

|

2 baths

|

2,145 sq ft

|

House

13190 SE 93RD CIR, SUMMERFIELD, FL, 3449...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 759 VILLA PARK RD, POINCIANA, FL, 34759, Poinciana, FL 34759
$522,000

2 beds

|

3 baths

|

2,956 sq ft

|

House

759 VILLA PARK RD, POINCIANA, FL, 34759
Community: Solivita
Del Webb Orlando 208 ALMERIA WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$449,900

2 beds

|

2 baths

|

1,927 sq ft

|

House

208 ALMERIA WAY, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Oak Run 7451 SW 111TH PL, OCALA, FL, 34476, Ocala, FL 34476
$369,000

3 beds

|

2 baths

|

2,320 sq ft

|

House

7451 SW 111TH PL, OCALA, FL, 34476
Community: Oak Run
Tampa Bay Golf and Country Club 11116 JENKINS CT, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$338,000

3 beds

|

2 baths

|

1,564 sq ft

|

House

11116 JENKINS CT, SAN ANTONIO, FL, 33576
Legacy of Leesburg 5107 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$348,000

3 beds

|

2 baths

|

1,658 sq ft

|

House

5107 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg

Frequently Asked Questions


Want more information about active adult communities around Winter Garden?

Global - Lead Form - Buyer or Renter

*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

3,964 homes near Winter Garden
Remove Boundaries ×
Map Satellite

Want to learn more about 55+ communities in Winter Garden?

Call us: (689) 407-5757

Call Us Call Us
Scroll to Top