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

3,958 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.
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) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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
Valencia Lakes 16106 CEDAR KEY DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$549,000

4 beds

|

3 baths

|

2,467 sq ft

|

House

16106 CEDAR KEY DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Solivita 439 MADERA PASS, POINCIANA, FL, 34759, Poinciana, FL 34759
$219,000

2 beds

|

1 baths

|

1,085 sq ft

|

House

439 MADERA PASS, POINCIANA, FL, 34759
Community: Solivita
Stone Creek 8951 SW 58TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$372,888

2 beds

|

2 baths

|

1,656 sq ft

|

House

8951 SW 58TH STREET RD, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 8420 SW 92ND ST B, OCALA, FL, 34481, Ocala, FL 34481
$189,900

2 beds

|

2 baths

|

1,688 sq ft

|

Villa

8420 SW 92ND ST B, OCALA, FL, 34481
Community: On Top of the World
Solivita 187 TALL PINES PASS, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$325,000

2 beds

|

2 baths

|

2,031 sq ft

|

House

187 TALL PINES PASS, KISSIMMEE, FL, 3475...
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1724 MAGNOLIA AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$210,000

2 beds

|

2 baths

|

1,390 sq ft

|

Manufactured Home

1724 MAGNOLIA AVE, LADY LAKE, FL, 32159
Community: The Villages®
Foxwood Lake Estates 4940 FOXDALE DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$167,500

2 beds

|

2 baths

|

943 sq ft

|

Manufactured Home

4940 FOXDALE DR, LAKELAND, FL, 33810
The Villages® 1461 SOTHELL ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$292,000

2 beds

|

2 baths

|

1,156 sq ft

|

House

1461 SOTHELL ST, THE VILLAGES, FL, 32162
Community: The Villages®
Ocala Palms 5858 NW 27TH PL, OCALA, FL, 34482, Ocala, FL 34482
$350,000

3 beds

|

2 baths

|

2,382 sq ft

|

House

5858 NW 27TH PL, OCALA, FL, 34482
Community: Ocala Palms
Stonecrest 10929 SE 167TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$479,000

3 beds

|

2 baths

|

2,133 sq ft

|

House

10929 SE 167TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
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.
Quail Meadow 4886 NW 30TH PL, OCALA, FL, 34482, Ocala, FL 34482
$319,900

3 beds

|

2 baths

|

1,442 sq ft

|

House

4886 NW 30TH PL, OCALA, FL, 34482
Community: Quail Meadow
On Top of the World 8814 SW 93RD LN C, OCALA, FL, 34481, Ocala, FL 34481
$139,450

2 beds

|

2 baths

|

1,369 sq ft

|

Villa

8814 SW 93RD LN C, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9617 SW 102ND TER, OCALA, FL, 34481, Ocala, FL 34481
$449,900

2 beds

|

2 baths

|

1,983 sq ft

|

House

9617 SW 102ND TER, OCALA, FL, 34481
Community: On Top of the World
Arlington Ridge 26715 MANASSAS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$499,900

3 beds

|

2 baths

|

2,449 sq ft

|

House

26715 MANASSAS DR, LEESBURG, FL, 34748
Community: Arlington Ridge
Solivita 681 CORONADO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$257,900

2 beds

|

2 baths

|

1,700 sq ft

|

House

681 CORONADO 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
Spring Lake Towers 700 MIRROR TER 403, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$168,000

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

700 MIRROR TER 403, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
Lakes of Mount Dora 7836 CROSSWINDS WAY, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$479,499

3 beds

|

2 baths

|

1,910 sq ft

|

House

7836 CROSSWINDS WAY, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
The Villages® 22103 SANDALWOOD DR # 103, WILDWOOD, FL,..., Wildwood, FL 34785
$149,900

2 beds

|

2 baths

|

1,156 sq ft

|

Condo

22103 SANDALWOOD DR # 103, WILDWOOD, FL,...
Community: The Villages®
Ocala Palms 2459 NW 55TH AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$255,000

3 beds

|

2 baths

|

1,514 sq ft

|

House

2459 NW 55TH AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
Kings Ridge 3827 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711
$319,000

2 beds

|

2 baths

|

1,465 sq ft

|

House

3827 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
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.
Spring Lake Towers 700 MIRROR TER 303, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$124,900

2 beds

|

2 baths

|

1,029 sq ft

|

Condo

700 MIRROR TER 303, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
Highlands Ridge 2802 S MAINSAIL DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$89,900

2 beds

|

2 baths

|

1,008 sq ft

|

Mobile Home

2802 S MAINSAIL DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Plantation at Leesburg 25239 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$279,990

2 beds

|

2 baths

|

1,563 sq ft

|

House

25239 CRANES ROOST CIR, LEESBURG, FL, 34...
Solivita 753 LARGO PASS, POINCIANA, FL, 34759, Poinciana, FL 34759
$254,900

2 beds

|

2 baths

|

1,467 sq ft

|

House

753 LARGO PASS, POINCIANA, FL, 34759
Community: Solivita
Sun City Center 303 CRANSTON PL, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$437,990

3 beds

|

2 baths

|

2,508 sq ft

|

House

303 CRANSTON PL, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 663 IRVINE RANCH RD, POINCIANA, FL, 3475..., Poinciana, FL 34759
$423,000

3 beds

|

3 baths

|

2,307 sq ft

|

House

663 IRVINE RANCH RD, POINCIANA, FL, 3475...
Community: Solivita
Four Seasons at Orlando 1855 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$375,000

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1855 FLORA PASS PL, KISSIMMEE, FL, 34747
Pennbrooke Fairways 32521 W GOLF CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$119,247

2 beds

|

1 baths

|

936 sq ft

|

Manufactured Home

32521 W GOLF CT, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Arlington Ridge 26951 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$255,000

2 beds

|

2 baths

|

1,418 sq ft

|

Villa

26951 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
Solivita 619 TAPATIO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$629,000

5 beds

|

5 baths

|

2,881 sq ft

|

House

619 TAPATIO LN, KISSIMMEE, FL, 34759
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.
Pennbrooke Fairways 910 EAGLES LNDG, LEESBURG, FL, 34748, Leesburg, FL 34748
$314,247

3 beds

|

2 baths

|

1,807 sq ft

|

House

910 EAGLES LNDG, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Solivita 465 VILLA PARK RD, POINCIANA, FL, 34759, Poinciana, FL 34759
$460,000

3 beds

|

3 baths

|

2,427 sq ft

|

House

465 VILLA PARK RD, POINCIANA, FL, 34759
Community: Solivita
Twin Lakes 2789 SOUTHLAND ST, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$555,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

2789 SOUTHLAND ST, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Del Webb Minneola 1104 WESTERN BLUE WAY, MINNEOLA, FL, 347..., Minneola, FL 34715
$644,000

3 beds

|

2 baths

|

1,889 sq ft

|

House

1104 WESTERN BLUE WAY, MINNEOLA, FL, 347...
Community: Del Webb Minneola
High Vista at Ridgewood Lakes 100 LAUREL OAK PASS, DAVENPORT, FL, 3383..., Davenport, FL 33837
$345,000

2 beds

|

2 baths

|

1,792 sq ft

|

House

100 LAUREL OAK PASS, DAVENPORT, FL, 3383...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2609 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$319,900

2 beds

|

2 baths

|

1,388 sq ft

|

House

2609 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
Spruce Creek Country Club 9405 SE 125TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$449,500

2 beds

|

2 baths

|

2,658 sq ft

|

House

9405 SE 125TH ST, SUMMERFIELD, FL, 34491
Pine Run Estates 10498 SW 99TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$149,000

2 beds

|

1 baths

|

768 sq ft

|

House

10498 SW 99TH AVE, OCALA, FL, 34481
Community: Pine Run Estates
On Top of the World 8342 SW 82ND LOOP, OCALA, FL, 34481, Ocala, FL 34481
$335,000

3 beds

|

2 baths

|

2,059 sq ft

|

House

8342 SW 82ND LOOP, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9357 SW 82ND TER B, OCALA, FL, 34481, Ocala, FL 34481
$231,900

2 beds

|

2 baths

|

1,249 sq ft

|

Villa

9357 SW 82ND TER B, OCALA, FL, 34481
Community: On Top of the World

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.

3,958 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