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

3,573 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 - $2Ms
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 (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 - $500Ks
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 - $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
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $500Ks
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
$300Ks - $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) VillageWalk at Lake Nona
$400Ks - $900Ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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
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...
$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 - $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 - $400Ks
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
$300Ks - $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
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $400Ks
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
Esplanade at Wiregrass Ranch 4294 CAIROLI CT, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$459,999

3 beds

|

2 baths

|

1,926 sq ft

|

House

4294 CAIROLI CT, WESLEY CHAPEL, FL, 3354...
The Villages® 8195 SE 174TH ROWLAND ST, THE VILLAGES, ..., The Villages, FL 32162
$269,000

2 beds

|

2 baths

|

1,208 sq ft

|

Villa

8195 SE 174TH ROWLAND ST, THE VILLAGES, ...
Community: The Villages®
The Villages® 1309 PINEY WOODS PATH, THE VILLAGES, FL,..., The Villages, FL 32163
$519,000

3 beds

|

2 baths

|

1,699 sq ft

|

House

1309 PINEY WOODS PATH, THE VILLAGES, FL,...
Community: The Villages®
The Villages® 2085 IRONTON PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$355,900

2 beds

|

2 baths

|

1,206 sq ft

|

House

2085 IRONTON PL, THE VILLAGES, FL, 32163
Community: The Villages®
Breakaway Trails 148 DEEP WOODS WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$445,000

3 beds

|

2 baths

|

2,561 sq ft

|

House

148 DEEP WOODS WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 5446 ALFREDSON TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$654,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

5446 ALFREDSON TER, THE VILLAGES, FL, 32...
Community: The Villages®
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®
On Top of the World 9669 SW 94TH AVE D, OCALA, FL, 34481, Ocala, FL 34481
$180,000

2 beds

|

2 baths

|

1,422 sq ft

|

Villa

9669 SW 94TH AVE D, OCALA, FL, 34481
Community: On Top of the World
The Villages® 1312 LANDEROS LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$299,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

1312 LANDEROS LN, THE VILLAGES, FL, 3215...
Community: The Villages®
Pennbrooke Fairways 353 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,000

3 beds

|

2 baths

|

1,755 sq ft

|

House

353 RANCHWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
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® 310 KNOLL PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$379,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

310 KNOLL PL, THE VILLAGES, FL, 32162
Community: The Villages®
Latitude Margaritaville 118 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$389,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

118 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Sun City Center 404 GRAND CHATEAUX WAY, SUN CITY CENTER,..., Sun City Center, FL 33573
$357,000

2 beds

|

2 baths

|

1,963 sq ft

|

House

404 GRAND CHATEAUX WAY, SUN CITY CENTER,...
Community: Sun City Center
Sun City Center 1526 FORT DUQUESNA DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$369,900

2 beds

|

2 baths

|

2,031 sq ft

|

House

1526 FORT DUQUESNA DR, SUN CITY CENTER, ...
Community: Sun City Center
The Villages® 744 BARRON PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$359,000

3 beds

|

2 baths

|

1,635 sq ft

|

House

744 BARRON PL, THE VILLAGES, FL, 32163
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Orlando 136 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$449,900

3 beds

|

3 baths

|

1,982 sq ft

|

House

136 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Breakaway Trails 11 FOREST VIEW WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$635,000

4 beds

|

2 baths

|

3,104 sq ft

|

House

11 FOREST VIEW WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
Sun City Center 906 BLUEWATER DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$299,999

2 beds

|

2 baths

|

1,756 sq ft

|

House

906 BLUEWATER DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
SummerGlen 1690 SW 158TH LN, OCALA, FL, 34473, Ocala, FL 34473
$279,900

3 beds

|

2 baths

|

1,647 sq ft

|

House

1690 SW 158TH LN, OCALA, FL, 34473
Community: SummerGlen
New On Top of the World 8872 SW 92ND PL F, OCALA, FL, 34481, Ocala, FL 34481
$164,900

2 beds

|

2 baths

|

1,394 sq ft

|

Villa

8872 SW 92ND PL F, OCALA, FL, 34481
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 North 10740 SW 62ND AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34476
$199,900

2 beds

|

2 baths

|

1,092 sq ft

|

House

10740 SW 62ND AVENUE RD, OCALA, FL, 3447...
Community: Spruce Creek North
The Villages® 7233 SE 171ST POND LN, THE VILLAGES, FL,..., The Villages, FL 32162
$349,900

2 beds

|

2 baths

|

1,918 sq ft

|

House

7233 SE 171ST POND LN, THE VILLAGES, FL,...
Community: The Villages®
The Villages® 9430 SE 176TH SAFFOLD ST, THE VILLAGES, ..., The Villages, FL 32162
$405,000

3 beds

|

2 baths

|

1,657 sq ft

|

House

9430 SE 176TH SAFFOLD ST, THE VILLAGES, ...
Community: The Villages®
The Villages® 1903 RUIZ CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$415,000

3 beds

|

2 baths

|

2,186 sq ft

|

House

1903 RUIZ CT, THE VILLAGES, FL, 32159
Community: The Villages®
New The Villages® 3364 ARCHER AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$267,500

2 beds

|

1 baths

|

971 sq ft

|

Villa

3364 ARCHER AVE, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Heritage Landings 2795 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$329,000

3 beds

|

2 baths

|

1,769 sq ft

|

House

2795 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
Lakes at Laurel Highlands 2795 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$329,000

3 beds

|

2 baths

|

1,769 sq ft

|

House

2795 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Ocala Preserve 5555 NW 40TH PL, OCALA, FL, 34482, Ocala, FL 34482
$469,000

3 beds

|

2 baths

|

1,854 sq ft

|

House

5555 NW 40TH PL, OCALA, FL, 34482
Community: Ocala Preserve
Plantation at Leesburg 24125 PEEKSKILL ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,000

2 beds

|

2 baths

|

1,935 sq ft

|

House

24125 PEEKSKILL ST, LEESBURG, FL, 34748
Esplanade at Wiregrass Ranch 29929 RADICE CT, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$674,999

3 beds

|

3 baths

|

2,397 sq ft

|

House

29929 RADICE CT, WESLEY CHAPEL, FL, 3354...
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.
SummerGlen 15659 SW 13TH CIR, OCALA, FL, 34473, Ocala, FL 34473
$261,000

2 beds

|

2 baths

|

1,593 sq ft

|

House

15659 SW 13TH CIR, OCALA, FL, 34473
Community: SummerGlen
Oak Run 8545 SW 108TH PL, OCALA, FL, 34481, Ocala, FL 34481
$175,000

2 beds

|

2 baths

|

1,265 sq ft

|

House

8545 SW 108TH PL, OCALA, FL, 34481
Community: Oak Run
New The Villages® 2495 DUNDEE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$339,000

2 beds

|

2 baths

|

1,258 sq ft

|

House

2495 DUNDEE TER, THE VILLAGES, FL, 32162
Community: The Villages®
Venetian Bay 3209 MEDICI BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$715,000

3 beds

|

2 baths

|

2,376 sq ft

|

House

3209 MEDICI BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Solivita 271 INDIAN WELLS AVE, POINCIANA, FL, 347..., Poinciana, FL 34759
$445,000

2 beds

|

2 baths

|

2,471 sq ft

|

House

271 INDIAN WELLS AVE, POINCIANA, FL, 347...
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 767 TREMONT GREENS LN # 64, SUN CITY CEN..., Sun City Center, FL 33573
$179,990

2 beds

|

2 baths

|

1,110 sq ft

|

Condo

767 TREMONT GREENS LN # 64, SUN CITY CEN...
Community: Sun City Center
Stonecrest 17789 SE 113TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$334,900

3 beds

|

3 baths

|

1,463 sq ft

|

House

17789 SE 113TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
Oak Run 10820 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481
$219,700

2 beds

|

2 baths

|

1,418 sq ft

|

House

10820 SW 87TH TER, OCALA, FL, 34481
Community: Oak Run
On Top of the World 7929 SW 80TH PLACE RD, OCALA, FL, 34476, Ocala, FL 34476
$219,900

2 beds

|

2 baths

|

1,319 sq ft

|

House

7929 SW 80TH PLACE RD, OCALA, FL, 34476
Community: On Top of the World
The Villages® 4157 COLLERETTE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163
$499,900

3 beds

|

2 baths

|

1,949 sq ft

|

House

4157 COLLERETTE CT, THE VILLAGES, FL, 32...
Community: The Villages®

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
3,573 homes near Winter Garden
Remove Boundaries ×
Map Satellite

Call Us Call Us
Scroll to Top