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

3,573 homes near Winter Garden

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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
<$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
$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 (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.
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
$300Ks - $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) 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
Sun City Center 202 BEDFORD ST APT 69, SUN CITY CENTER, ..., Sun City Center, FL 33573
$169,500

2 beds

|

2 baths

|

960 sq ft

|

Condo

202 BEDFORD ST APT 69, SUN CITY CENTER, ...
Community: Sun City Center
Latitude Margaritaville 329 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$475,000

2 beds

|

2 baths

|

1,862 sq ft

|

House

329 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Plantation at Leesburg 24947 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$244,900

3 beds

|

2 baths

|

1,653 sq ft

|

House

24947 CRANES ROOST CIR, LEESBURG, FL, 34...
The Villages® 8960 SE 178TH MUIRFIELD PL, THE VILLAGES..., The Villages, FL 32162
$369,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

8960 SE 178TH MUIRFIELD PL, THE VILLAGES...
Community: The Villages®
Tarawood 10485 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436
$267,000

2 beds

|

2 baths

|

1,641 sq ft

|

House

10485 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lakes of Mount Dora 1990 WALLINGFORD LOOP, MOUNT DORA, FL, 3..., Mount Dora, FL 32757
$674,900

3 beds

|

3 baths

|

2,330 sq ft

|

House

1990 WALLINGFORD LOOP, MOUNT DORA, FL, 3...
Community: Lakes of Mount Dora
On Top of the World 9912 SW 82ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$642,246

3 beds

|

3 baths

|

2,472 sq ft

|

House

9912 SW 82ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 1732 FLAMINGO LN, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$274,900

2 beds

|

2 baths

|

1,778 sq ft

|

House

1732 FLAMINGO LN, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Colonnades 1608 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$269,900

2 beds

|

2 baths

|

1,305 sq ft

|

House

1608 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
Solivita 729 SAN RAPHAEL ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$514,900

4 beds

|

4 baths

|

2,616 sq ft

|

House

729 SAN RAPHAEL ST, 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.
Sun City Center 1801 BEDFORD TER 235, SUN CITY CENTER, F..., Sun City Center, FL 33573
$99,500

1 beds

|

2 baths

|

800 sq ft

|

Condo

1801 BEDFORD TER 235, SUN CITY CENTER, F...
Community: Sun City Center
Cherrywood 5968 SW 103RD LOOP, OCALA, FL, 34476, Ocala, FL 34476
$279,000

3 beds

|

2 baths

|

1,713 sq ft

|

House

5968 SW 103RD LOOP, OCALA, FL, 34476
Community: Cherrywood
Sun City Center 2447 NANTUCKET HARBOR LOOP # 112, SUN CI..., Sun City Center, FL 33573
$239,900

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

2447 NANTUCKET HARBOR LOOP # 112, SUN CI...
Community: Sun City Center
Royal Highlands 22247 DRAW BRIDGE DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$379,900

3 beds

|

2 baths

|

2,428 sq ft

|

House

22247 DRAW BRIDGE DR, LEESBURG, FL, 3474...
Community: Royal Highlands
Latitude Margaritaville 894 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$744,900

3 beds

|

3 baths

|

2,493 sq ft

|

House

894 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Highlands 21708 ROYAL ST GEORGES LN, LEESBURG, FL,..., Leesburg, FL 34748
$262,000

3 beds

|

2 baths

|

2,253 sq ft

|

House

21708 ROYAL ST GEORGES LN, LEESBURG, FL,...
Community: Royal Highlands
Sun City Center 608 FORT DUQUESNA DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$334,000

2 beds

|

2 baths

|

2,028 sq ft

|

House

608 FORT DUQUESNA DR, SUN CITY CENTER, F...
Community: Sun City Center
Tampa Bay Golf and Country Club 10523 HYANNISPORT LOOP, SAN ANTONIO, FL,..., San Antonio, FL 33576
$375,000

2 beds

|

2 baths

|

1,943 sq ft

|

House

10523 HYANNISPORT LOOP, SAN ANTONIO, FL,...
Sun City Center 702 CYPRESS PL, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$374,900

3 beds

|

2 baths

|

1,810 sq ft

|

House

702 CYPRESS PL, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Sun City Center 611 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$349,900

2 beds

|

2 baths

|

1,668 sq ft

|

Townhouse

611 CHIPPER DR, SUN CITY CENTER, FL, 335...
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.
Sun City Center 724 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$410,000

3 beds

|

2 baths

|

1,800 sq ft

|

Villa

724 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Cresswind DeLand 1262 VENICE CT, DELAND, FL, 32724, Deland, FL 32724
$584,990

3 beds

|

3 baths

|

2,129 sq ft

|

House

1262 VENICE CT, DELAND, FL, 32724
Community: Cresswind DeLand
The Villages® 1871 W SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$379,000

3 beds

|

2 baths

|

1,599 sq ft

|

House

1871 W SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
The Villages® 2608 BOTELLO AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$248,995

2 beds

|

2 baths

|

1,231 sq ft

|

House

2608 BOTELLO AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
Sun City Center 689 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$300,000

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

689 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1502 FORT DUQUESNA DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$298,900

2 beds

|

2 baths

|

1,872 sq ft

|

House

1502 FORT DUQUESNA DR, SUN CITY CENTER, ...
Community: Sun City Center
Kings Ridge 4020 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$350,000

3 beds

|

2 baths

|

1,572 sq ft

|

House

4020 CAPLAND AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Spruce Creek South 17533 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$268,900

2 beds

|

2 baths

|

1,534 sq ft

|

House

17533 SE 96TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Sun City Center 334 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$219,900

2 beds

|

2 baths

|

1,516 sq ft

|

Condo

334 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
The Villages® 520 SAINT ANDREWS BLVD, THE VILLAGES, FL..., The Villages, FL 32159
$229,900

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

520 SAINT ANDREWS BLVD, THE VILLAGES, FL...
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 Preserve 12044 SW 137TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432
$304,900

2 beds

|

2 baths

|

1,630 sq ft

|

House

12044 SW 137TH LOOP, DUNNELLON, FL, 3443...
Royal Highlands 5007 KELSO ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$274,500

2 beds

|

2 baths

|

1,469 sq ft

|

House

5007 KELSO ST, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 514 SAINT ANDREWS BLVD, THE VILLAGES, FL..., The Villages, FL 32159
$230,000

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

514 SAINT ANDREWS BLVD, THE VILLAGES, FL...
Community: The Villages®
Highland Lakes 6410 TILDON CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$279,900

3 beds

|

2 baths

|

1,957 sq ft

|

House

6410 TILDON CT, LEESBURG, FL, 34748
Community: Highland Lakes
Spruce Creek Preserve 11470 SW 139TH ST, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$244,000

2 beds

|

2 baths

|

1,672 sq ft

|

House

11470 SW 139TH ST, DUNNELLON, FL, 34432
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1005 HAREFIELD CIR # 43, SUN CITY CENTER..., Sun City Center, FL 33573
$219,500

2 beds

|

2 baths

|

1,448 sq ft

|

Condo

1005 HAREFIELD CIR # 43, SUN CITY CENTER...
Community: Sun City Center
Cherrywood 6150 SW 103RD LOOP, OCALA, FL, 34476, Ocala, FL 34476
$199,000

3 beds

|

2 baths

|

1,364 sq ft

|

House

6150 SW 103RD LOOP, OCALA, FL, 34476
Community: Cherrywood
Lake Ashton 6265 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$549,000

3 beds

|

2 baths

|

2,521 sq ft

|

House

6265 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Harbor Hills Country Club 39634 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$499,000

3 beds

|

2 baths

|

2,579 sq ft

|

House

39634 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Stone Creek 8606 SW 61ST LOOP, OCALA, FL, 34481, Ocala, FL 34481
$724,900

3 beds

|

3 baths

|

2,512 sq ft

|

House

8606 SW 61ST LOOP, OCALA, FL, 34481
Community: Stone Creek

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3,573 homes near Winter Garden
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