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

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

3,631 homes near Winter Garden

Sort by:

Relevance

Relevance

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
Sun City Center 1103 VILLEROY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$417,000

3 beds

|

2 baths

|

1,490 sq ft

|

House

1103 VILLEROY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
VillageWalk at Lake Nona 11858 BARLETTA DR, ORLANDO, FL, 32827, Orlando, FL 32827
$614,000

3 beds

|

2 baths

|

1,941 sq ft

|

House

11858 BARLETTA DR, ORLANDO, FL, 32827
Quail Meadow 1795 NW 44TH COURT RD, OCALA, FL, 34482, Ocala, FL 34482
$369,900

5 beds

|

3 baths

|

2,445 sq ft

|

House

1795 NW 44TH COURT RD, OCALA, FL, 34482
Community: Quail Meadow
The Villages® 8069 SE 174TH LUDLOW PL, THE VILLAGES, F..., The Villages, FL 32162
$350,000

3 beds

|

2 baths

|

1,481 sq ft

|

House

8069 SE 174TH LUDLOW PL, THE VILLAGES, F...
Community: The Villages®
SummerGlen 16052 SW 15TH CT, OCALA, FL, 34473, Ocala, FL 34473
$289,000

3 beds

|

3 baths

|

1,759 sq ft

|

House

16052 SW 15TH CT, OCALA, FL, 34473
Community: SummerGlen
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Arlington Ridge 26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748
$499,900

4 beds

|

3 baths

|

2,318 sq ft

|

House

26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
Plantation at Leesburg 4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$429,900

3 beds

|

3 baths

|

2,780 sq ft

|

House

4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34...
Pelican Bay Daytona Beach 102 BOB WHITE CT APT 9, DAYTONA BEACH, F..., Daytona Beach, FL 32119
$155,000

1 beds

|

1 baths

|

894 sq ft

|

Condo

102 BOB WHITE CT APT 9, DAYTONA BEACH, F...
Summer Trees 109 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$273,827

2 beds

|

2 baths

|

1,106 sq ft

|

House

109 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Summer Trees 39 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$280,000

2 beds

|

2 baths

|

1,406 sq ft

|

House

39 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
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 319 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$499,900

2 beds

|

2 baths

|

1,563 sq ft

|

House

319 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 429 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$539,900

3 beds

|

2 baths

|

1,848 sq ft

|

House

429 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Pelican Bay Daytona Beach 220 BOB WHITE CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119
$249,900

3 beds

|

2 baths

|

1,377 sq ft

|

Condo

220 BOB WHITE CT, DAYTONA BEACH, FL, 321...
Latitude Margaritaville 710 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$565,000

2 beds

|

3 baths

|

1,743 sq ft

|

House

710 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 119 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$549,900

3 beds

|

2 baths

|

1,862 sq ft

|

House

119 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 3583 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$789,900

3 beds

|

2 baths

|

2,273 sq ft

|

House

3583 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Latitude Margaritaville 285 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$519,900

3 beds

|

2 baths

|

1,848 sq ft

|

Townhouse

285 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Latitude Margaritaville 356 PARROT LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$409,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

356 PARROT LN, DAYTONA BEACH, FL, 32124
Venetian Bay 3357 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$524,900

4 beds

|

3 baths

|

2,835 sq ft

|

House

3357 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
The Villages® 17037 SE 76TH CREEKSIDE CIR, THE VILLAGE..., The Villages, FL 32162
$490,000

3 beds

|

2 baths

|

2,136 sq ft

|

House

17037 SE 76TH CREEKSIDE CIR, THE VILLAGE...
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.
Solivita 128 RIALTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$325,000

2 beds

|

2 baths

|

1,398 sq ft

|

House

128 RIALTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Stonecrest 11092 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$379,000

3 beds

|

3 baths

|

2,071 sq ft

|

House

11092 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Solivita 525 GENOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$474,000

3 beds

|

3 baths

|

2,325 sq ft

|

House

525 GENOA DR, KISSIMMEE, FL, 34759
Community: Solivita
Stonecrest 16863 SE 110TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$369,000

3 beds

|

2 baths

|

1,687 sq ft

|

House

16863 SE 110TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
Valencia Lakes 16301 GARNET GLEN PL, WIMAUMA, FL, 33598, Wimauma, FL 33598
$647,500

3 beds

|

4 baths

|

2,723 sq ft

|

House

16301 GARNET GLEN PL, WIMAUMA, FL, 33598
Community: Valencia Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Breakaway Trails 24 LAKE VISTA WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$509,900

4 beds

|

3 baths

|

2,544 sq ft

|

House

24 LAKE VISTA WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
The Villages® 1405 ESPINOZA LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$220,000

1 beds

|

1 baths

|

804 sq ft

|

Villa

1405 ESPINOZA LN, THE VILLAGES, FL, 3215...
Community: The Villages®
Majestic Oaks Ocala 5351 SW 80TH PL, OCALA, FL, 34476, Ocala, FL 34476
$265,000

2 beds

|

2 baths

|

1,520 sq ft

|

House

5351 SW 80TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Ocala Preserve 3642 NW 55TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$565,000

2 beds

|

3 baths

|

2,315 sq ft

|

House

3642 NW 55TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Del Webb Oasis 13066 SUNNY RETREAT LN, WINTER GARDEN, F..., Winter Garden, FL 34787
$674,990

2 beds

|

2 baths

|

1,899 sq ft

|

House

13066 SUNNY RETREAT LN, WINTER GARDEN, F...
Community: Del Webb Oasis
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.
Ocala Palms 2515 NW 53RD AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$369,500

3 beds

|

2 baths

|

2,399 sq ft

|

House

2515 NW 53RD AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
Lake Ashton 4081 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$424,000

3 beds

|

2 baths

|

2,027 sq ft

|

House

4081 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Ocala Palms 2100 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$269,500

2 beds

|

2 baths

|

1,669 sq ft

|

House

2100 NW 50TH CIR, OCALA, FL, 34482
Community: Ocala Palms
Oak Run 10824 SW 90TH TER, OCALA, FL, 34481, Ocala, FL 34481
$182,000

2 beds

|

2 baths

|

960 sq ft

|

House

10824 SW 90TH TER, OCALA, FL, 34481
Community: Oak Run
Lake Ashton 4433 VENTANA LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$484,900

3 beds

|

2 baths

|

2,512 sq ft

|

House

4433 VENTANA LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 668 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$679,138

5 beds

|

4 baths

|

3,221 sq ft

|

House

668 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Venetian Bay 673 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$738,364

6 beds

|

5 baths

|

4,181 sq ft

|

House

673 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Del Webb Sunbridge 2904 VOYAGER AVE, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$389,990

3 beds

|

3 baths

|

1,744 sq ft

|

Townhouse

2904 VOYAGER AVE, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Del Webb Sunbridge 6507 TRAILBLAZE BND, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$334,990

3 beds

|

3 baths

|

1,744 sq ft

|

Townhouse

6507 TRAILBLAZE BND, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
Venetian Bay 672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$643,384

4 beds

|

4 baths

|

2,748 sq ft

|

House

672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay

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.

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

Call us: (689) 407-5757
3,631 homes near Winter Garden
Remove Boundaries ×
Map Satellite

Call Us Call Us
Scroll to Top