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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
$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
The Villages® 2036 CHESAPEAKE PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$304,999

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

2036 CHESAPEAKE PL, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 870 ROBLES AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$395,900

3 beds

|

2 baths

|

1,279 sq ft

|

Villa

870 ROBLES AVE, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 6222 DINGMAN WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$575,000

3 beds

|

2 baths

|

1,524 sq ft

|

Villa

6222 DINGMAN WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 3359 BRIANNA LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$414,000

3 beds

|

2 baths

|

1,584 sq ft

|

House

3359 BRIANNA LN, THE VILLAGES, FL, 32163
Community: The Villages®
New The Villages® 647 SAN PEDRO DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$314,900

2 beds

|

2 baths

|

1,383 sq ft

|

House

647 SAN PEDRO DR, THE VILLAGES, FL, 3215...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 289 ZINGALE LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$339,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

289 ZINGALE LN, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 220 ESTRADA PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$269,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

220 ESTRADA PL, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 829 CORTEZ AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$350,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

829 CORTEZ AVE, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3431 KANANWOOD TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$500,000

3 beds

|

2 baths

|

2,003 sq ft

|

House

3431 KANANWOOD TER, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 17606 SE 93RD BUTLER CT, THE VILLAGES, F..., The Villages, FL 32162
$290,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

17606 SE 93RD BUTLER CT, THE VILLAGES, F...
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.
The Villages® 762 TURBEVILLE TER, THE VILLAGES, FL, 32..., The Villages, FL 32162
$424,900

3 beds

|

2 baths

|

1,861 sq ft

|

House

762 TURBEVILLE TER, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 2935 CEDAR GROVE LOOP, THE VILLAGES, FL,..., The Villages, FL 32163
$950,000

3 beds

|

2 baths

|

3,466 sq ft

|

House

2935 CEDAR GROVE LOOP, THE VILLAGES, FL,...
Community: The Villages®
The Villages® 901 CHULA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$312,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

901 CHULA CT, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 411 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$359,000

3 beds

|

2 baths

|

1,632 sq ft

|

House

411 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 703 ROYAL PALM AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$425,000

3 beds

|

2 baths

|

1,730 sq ft

|

House

703 ROYAL PALM AVE, LADY LAKE, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Southshore Bay 17415 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$539,900

3 beds

|

3 baths

|

2,651 sq ft

|

House

17415 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
The Villages® 705 PRADO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$274,900

2 beds

|

2 baths

|

1,383 sq ft

|

House

705 PRADO DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 2101 SOUTHERN STAR WAY, THE VILLAGES, FL..., The Villages, FL 32162
$379,900

3 beds

|

2 baths

|

1,398 sq ft

|

Villa

2101 SOUTHERN STAR WAY, THE VILLAGES, FL...
Community: The Villages®
The Villages® 2907 BARBOZA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$274,500

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2907 BARBOZA DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 3389 LUTY LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$385,000

3 beds

|

2 baths

|

1,547 sq ft

|

House

3389 LUTY LN, THE VILLAGES, FL, 32163
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.
The Villages® 3283 DAWN PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$289,900

2 beds

|

2 baths

|

1,223 sq ft

|

Villa

3283 DAWN PL, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 5081 FRANCIS LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$399,900

3 beds

|

2 baths

|

1,569 sq ft

|

House

5081 FRANCIS LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 3154 MERRIT LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$410,500

3 beds

|

2 baths

|

1,828 sq ft

|

Villa

3154 MERRIT LN, THE VILLAGES, FL, 32163
Community: The Villages®
Cherrywood 10307 SW 61ST TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$215,000

3 beds

|

2 baths

|

1,428 sq ft

|

House

10307 SW 61ST TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
Palms at Serenoa 3449 MEADOW BEAUTY WAY, CLERMONT, FL, 34..., Clermont, FL 34714
$368,500

2 beds

|

2 baths

|

1,646 sq ft

|

House

3449 MEADOW BEAUTY WAY, CLERMONT, FL, 34...
Community: Palms at Serenoa
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 101 CAMBRIDGE TRL 212, SUN CITY CENTER, ..., Sun City Center, FL 33573
$104,900

2 beds

|

2 baths

|

960 sq ft

|

Condo

101 CAMBRIDGE TRL 212, SUN CITY CENTER, ...
Community: Sun City Center
Latitude Margaritaville 138 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$698,000

3 beds

|

3 baths

|

2,483 sq ft

|

House

138 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Royal Highlands 20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$389,000

3 beds

|

3 baths

|

2,224 sq ft

|

House

20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
New Sun City Center 2307 EMERALD LAKE DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$415,000

2 beds

|

2 baths

|

1,689 sq ft

|

House

2307 EMERALD LAKE DR, SUN CITY CENTER, F...
Community: Sun City Center
High Vista at Ridgewood Lakes 235 ROYAL PALM DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$324,999

3 beds

|

2 baths

|

1,870 sq ft

|

House

235 ROYAL PALM DR, DAVENPORT, FL, 33837
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® 1910 ANTONIA PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$359,900

3 beds

|

2 baths

|

1,882 sq ft

|

House

1910 ANTONIA PL, THE VILLAGES, FL, 32159
Community: The Villages®
Sun City Center 721 ELKHORN RD, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$310,000

3 beds

|

2 baths

|

2,522 sq ft

|

House

721 ELKHORN RD, SUN CITY CENTER, FL, 335...
Community: Sun City Center
On Top of the World 7809 SW 86TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$290,000

3 beds

|

2 baths

|

1,465 sq ft

|

House

7809 SW 86TH LOOP, OCALA, FL, 34476
Community: On Top of the World
New Ocala Palms 1913 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$184,900

2 beds

|

2 baths

|

1,182 sq ft

|

House

1913 NW 50TH CIR, OCALA, FL, 34482
Community: Ocala Palms
Oak Run 13138 SW 74TH CT, OCALA, FL, 34473, Ocala, FL 34473
$309,900

4 beds

|

2 baths

|

1,787 sq ft

|

House

13138 SW 74TH CT, OCALA, FL, 34473
Community: Oak Run
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3772 VISCAYA CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$305,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

3772 VISCAYA CT, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 17461 SE 82ND ALBEMARLE AVE, THE VILLAGE..., The Villages, FL 32162
$279,900

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

17461 SE 82ND ALBEMARLE AVE, THE VILLAGE...
Community: The Villages®
Solivita 615 DAVINCI PASS, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$374,900

3 beds

|

3 baths

|

2,276 sq ft

|

House

615 DAVINCI PASS, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 1032 VENTURA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$539,000

2 beds

|

2 baths

|

1,734 sq ft

|

House

1032 VENTURA DR, THE VILLAGES, FL, 32159
Community: The Villages®
Sun City Center 646 ALLEGHENY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$279,000

2 beds

|

2 baths

|

1,522 sq ft

|

House

646 ALLEGHENY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center

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3,573 homes near Winter Garden
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