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

3,952 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 - $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
$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.
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $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) 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...
$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
$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
$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 - $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
Pennbrooke Fairways 32334 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$139,990

2 beds

|

2 baths

|

824 sq ft

|

Manufactured Home

32334 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Stone Creek 9582 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$240,000

2 beds

|

2 baths

|

1,696 sq ft

|

Villa

9582 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Baytree 579 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778
$218,000

2 beds

|

2 baths

|

1,024 sq ft

|

Villa

579 JUNIPER WAY, TAVARES, FL, 32778
Community: Baytree
Pennbrooke Fairways 33236 GRAND CYPRESS WAY, LEESBURG, FL, 3..., Leesburg, FL 34748
$314,247

3 beds

|

2 baths

|

1,598 sq ft

|

House

33236 GRAND CYPRESS WAY, LEESBURG, FL, 3...
Community: Pennbrooke Fairways
Del Webb Sunbridge 6117 SANDY SPRINGS CT, SAINT CLOUD, FL, ..., Saint Cloud, FL 34771
$675,000

3 beds

|

3 baths

|

2,483 sq ft

|

House

6117 SANDY SPRINGS CT, SAINT CLOUD, FL, ...
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 3587 NW 55TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$599,000

3 beds

|

3 baths

|

2,360 sq ft

|

House

3587 NW 55TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Highlands Ridge 3015 OAKHILL DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$265,000

2 beds

|

3 baths

|

1,861 sq ft

|

House

3015 OAKHILL DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Spring Lake Towers 700 MIRROR TER 505, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$139,400

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

700 MIRROR TER 505, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
Tampa Bay Golf and Country Club 10520 COLLAR DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$425,000

3 beds

|

2 baths

|

2,046 sq ft

|

House

10520 COLLAR DR, SAN ANTONIO, FL, 33576
The Villages® 2053 BEECHER PATH, THE VILLAGES, FL, 321..., The Villages, FL 32162
$495,000

3 beds

|

2 baths

|

1,876 sq ft

|

House

2053 BEECHER PATH, THE VILLAGES, FL, 321...
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 428 BEL AIR WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$535,999

3 beds

|

2 baths

|

2,023 sq ft

|

House

428 BEL AIR WAY, KISSIMMEE, FL, 34759
Community: Solivita
Venetian Bay 3402 TORRE BLVD, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$372,900

2 beds

|

2 baths

|

1,667 sq ft

|

Townhouse

3402 TORRE BLVD, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Lakeside Landings 5466 COMPASS PT # 101, OXFORD, FL, 34484, Oxford, FL 34484
$244,900

2 beds

|

2 baths

|

1,281 sq ft

|

Condo

5466 COMPASS PT # 101, OXFORD, FL, 34484
Community: Lakeside Landings
Sun City Center 2243 WORTHINGTON GREENS DR, SUN CITY CEN..., Sun City Center, FL 33573
$239,900

2 beds

|

2 baths

|

1,723 sq ft

|

Condo

2243 WORTHINGTON GREENS DR, SUN CITY CEN...
Community: Sun City Center
Latitude Margaritaville 867 BAMA BREEZE DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$499,000

2 beds

|

3 baths

|

1,748 sq ft

|

Villa

867 BAMA BREEZE DR, DAYTONA BEACH, FL, 3...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 280 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$369,900

3 beds

|

2 baths

|

1,618 sq ft

|

House

280 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Royal Harbor 5604 GULF STREAM ST, TAVARES, FL, 32778, Tavares, FL 32778
$300,000

3 beds

|

2 baths

|

1,535 sq ft

|

House

5604 GULF STREAM ST, TAVARES, FL, 32778
Community: Royal Harbor
Lakes of Mount Dora 3975 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$456,990

2 beds

|

2 baths

|

1,402 sq ft

|

House

3975 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
High Vista at Ridgewood Lakes 1111 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$280,000

3 beds

|

2 baths

|

1,415 sq ft

|

House

1111 HIGH VISTA DR, DAVENPORT, FL, 33837
Sun City Center 635 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$324,000

2 beds

|

2 baths

|

1,493 sq ft

|

Villa

635 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.
Twin Lakes 2524 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$280,000

2 beds

|

2 baths

|

1,261 sq ft

|

Villa

2524 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Spruce Creek Country Club 9651 SE 137TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$469,000

3 beds

|

2 baths

|

2,411 sq ft

|

House

9651 SE 137TH STREET RD, SUMMERFIELD, FL...
Spruce Creek Country Club 9910 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$404,000

3 beds

|

2 baths

|

2,025 sq ft

|

House

9910 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Stone Creek 5779 SW 87TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$299,900

2 beds

|

2 baths

|

1,471 sq ft

|

House

5779 SW 87TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
Royal Highlands 21242 BRAVEHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$310,000

3 beds

|

2 baths

|

1,943 sq ft

|

House

21242 BRAVEHEART DR, LEESBURG, FL, 34748
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 5300 TIGERS TAIL, LEESBURG, FL, 34748, Leesburg, FL 34748
$190,000

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

5300 TIGERS TAIL, LEESBURG, FL, 34748
Pennbrooke Fairways 32314 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$164,247

2 beds

|

1 baths

|

640 sq ft

|

House

32314 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Pennbrooke Fairways 509 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,247

3 beds

|

2 baths

|

1,872 sq ft

|

House

509 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
The Villages® 1010 VENTURA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$412,247

3 beds

|

2 baths

|

1,530 sq ft

|

House

1010 VENTURA DR, THE VILLAGES, FL, 32159
Community: The Villages®
Pelican Bay Daytona Beach 129 SAND FIDDLER CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$289,900

2 beds

|

2 baths

|

1,908 sq ft

|

House

129 SAND FIDDLER CT, DAYTONA BEACH, FL, ...
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 16299 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$294,900

2 beds

|

2 baths

|

1,820 sq ft

|

House

16299 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Harbor Hills Country Club 39539 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$469,000

3 beds

|

3 baths

|

2,303 sq ft

|

House

39539 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Sun City Center 2019 ACADIA GREENS DR # 34, SUN CITY CEN..., Sun City Center, FL 33573
$249,000

2 beds

|

2 baths

|

1,194 sq ft

|

Condo

2019 ACADIA GREENS DR # 34, SUN CITY CEN...
Community: Sun City Center
Spruce Creek South 17937 SE 107TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$259,900

3 beds

|

2 baths

|

1,450 sq ft

|

House

17937 SE 107TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Sun City Center 2403 NANTUCKET GREEN CT, SUN CITY CENTER..., Sun City Center, FL 33573
$220,000

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2403 NANTUCKET GREEN CT, SUN CITY CENTER...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1004 MATTHEW AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$164,900

2 beds

|

2 baths

|

936 sq ft

|

Manufactured Home

1004 MATTHEW AVE, LADY LAKE, FL, 32159
Community: The Villages®
Solivita 521 MILANO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$460,000

3 beds

|

3 baths

|

2,450 sq ft

|

House

521 MILANO RD, KISSIMMEE, FL, 34759
Community: Solivita
Serenity Reserve 2400 SYMPHONY CIR, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34771
$625,000

3 beds

|

4 baths

|

2,148 sq ft

|

House

2400 SYMPHONY CIR, SAINT CLOUD, FL, 3477...
Community: Serenity Reserve
Spruce Creek Country Club 12239 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$375,000

3 beds

|

2 baths

|

2,259 sq ft

|

House

12239 SE 92ND COURT RD, SUMMERFIELD, FL,...
Valencia Lakes 4822 GRAND BANKS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$540,000

3 beds

|

3 baths

|

2,271 sq ft

|

House

4822 GRAND BANKS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes

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3,952 homes near Winter Garden
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