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Winter Garden, FL 55+ active adult communities & homes for sale - Page 10

3,495 homes near Winter Garden

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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 - $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 - $700Ks
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 - $500Ks
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 - $600Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
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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 - $900Ks
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
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 (2 reviews) Plantation at Leesburg
$100Ks - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
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 - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
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Pelican Bay Daytona Beach
$100Ks - $400Ks
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
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $600Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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 (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
Venetian Bay
$200Ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
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Questions? Call us: (689) 407-5757
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
4 rating (7 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
$300Ks - $1Ms
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
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) 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 - $400Ks
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
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Questions? Call us: (689) 407-5757
5 rating (5 reviews) SummerGlen
$100Ks - $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
Breakaway Trails
$400Ks - $800Ks
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
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.
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
4.8 rating (6 reviews) Highland Lakes
$100Ks - $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
Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Stone Creek 8339 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$368,770

3 beds

|

2 baths

|

1,662 sq ft

|

House

8339 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 5445 SW 86TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$357,450

2 beds

|

2 baths

|

1,655 sq ft

|

House

5445 SW 86TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 8467 SW 55TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$437,080

2 beds

|

2 baths

|

1,948 sq ft

|

House

8467 SW 55TH STREET RD, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 5321 SW 81ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$403,520

3 beds

|

2 baths

|

1,662 sq ft

|

House

5321 SW 81ST CIR, OCALA, FL, 34481
Community: Stone Creek
The Villages® 1130 AVENIDA DE LAS CASAS, LADY LAKE, FL..., Lady Lake, FL 32159
$445,000

2 beds

|

3 baths

|

1,780 sq ft

|

Condo

1130 AVENIDA DE LAS CASAS, LADY LAKE, FL...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 8343 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$369,860

4 beds

|

2 baths

|

1,850 sq ft

|

House

8343 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 8360 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$482,290

2 beds

|

2 baths

|

1,948 sq ft

|

House

8360 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
New Lake Ashton 4105 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$535,000

3 beds

|

3 baths

|

2,371 sq ft

|

House

4105 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
New Carlsberg Estates on Lake Suzanne 235 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$289,900

3 beds

|

3 baths

|

1,744 sq ft

|

House

235 LAKE SUZANNE DR, LAKE WALES, FL, 338...
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.
New Spruce Creek North 6286 SW 110TH ST, OCALA, FL, 34476, Ocala, FL 34476
$200,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

6286 SW 110TH ST, OCALA, FL, 34476
Community: Spruce Creek North
Stone Creek 8323 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$408,190

2 beds

|

2 baths

|

1,670 sq ft

|

House

8323 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Majestic Oaks Ocala 5461 SW 87TH PL, OCALA, FL, 34476, Ocala, FL 34476
$495,580

2 beds

|

3 baths

|

2,269 sq ft

|

House

5461 SW 87TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Sandpiper Golf & Country Club 6381 EGRET DR 28, LAKELAND, FL, 33809, Lakeland, FL 33809
$232,000

2 beds

|

2 baths

|

941 sq ft

|

Villa

6381 EGRET DR 28, LAKELAND, FL, 33809
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New The Villages® 3065 GLENWOOD PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$345,900

3 beds

|

2 baths

|

1,490 sq ft

|

House

3065 GLENWOOD PL, THE VILLAGES, FL, 3216...
Community: The Villages®
New On Top of the World 10453 SW 99TH LN, OCALA, FL, 34481, Ocala, FL 34481
$534,900

2 beds

|

2 baths

|

2,097 sq ft

|

House

10453 SW 99TH LN, OCALA, FL, 34481
Community: On Top of the World
The Villages® 109 LYONIA LN, WILDWOOD, FL, 34785, Wildwood, FL 34785
$110,000

2 beds

|

2 baths

|

1,152 sq ft

|

Manufactured Home

109 LYONIA LN, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 421 ALDAMA AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$349,247

3 beds

|

2 baths

|

1,392 sq ft

|

House

421 ALDAMA AVE, THE VILLAGES, FL, 32159
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® 3258 IIAMS CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$349,900

3 beds

|

2 baths

|

1,476 sq ft

|

House

3258 IIAMS CT, THE VILLAGES, FL, 32163
Community: The Villages®
New The Villages® 17883 SE 87TH MELROSE CT, THE VILLAGES, ..., The Villages, FL 32162
$369,900

3 beds

|

2 baths

|

1,855 sq ft

|

House

17883 SE 87TH MELROSE CT, THE VILLAGES, ...
Community: The Villages®
The Villages® 3468 ROANOKE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$265,000

2 beds

|

2 baths

|

1,182 sq ft

|

Villa

3468 ROANOKE ST, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1850 KYRLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$1,050,000

3 beds

|

2 baths

|

2,227 sq ft

|

House

1850 KYRLE TER, 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
Solivita 601 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$239,239

2 beds

|

2 baths

|

1,258 sq ft

|

House

601 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Venetian Bay 2967 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$358,500

3 beds

|

3 baths

|

1,672 sq ft

|

House

2967 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
The Villages® 2864 MANOR DOWNS, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$485,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

2864 MANOR DOWNS, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 703 MELENDEZ WAY, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$339,000

3 beds

|

2 baths

|

1,509 sq ft

|

House

703 MELENDEZ WAY, THE VILLAGES, FL, 3215...
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® 651 D ANGELO LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$435,000

3 beds

|

2 baths

|

1,357 sq ft

|

Villa

651 D ANGELO LN, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 3604 CAMBRIA CIR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$265,000

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

3604 CAMBRIA CIR, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 733 PALMA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$340,000

3 beds

|

2 baths

|

1,936 sq ft

|

House

733 PALMA DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1850 LAKE RIDGE DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$1,150,000

3 beds

|

3 baths

|

2,964 sq ft

|

House

1850 LAKE RIDGE DR, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 290 JEFFERSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$340,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

290 JEFFERSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1717 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$280,000

2 beds

|

2 baths

|

1,143 sq ft

|

Villa

1717 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 3377 CLARA CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$299,900

2 beds

|

2 baths

|

1,240 sq ft

|

Villa

3377 CLARA CT, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 9231 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162
$375,900

3 beds

|

2 baths

|

1,850 sq ft

|

House

9231 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
Pelican Bay Daytona Beach 256 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$229,000

2 beds

|

2 baths

|

1,146 sq ft

|

Halfplex

256 PALM SPARROW 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.
Venetian Bay 677 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$664,689

4 beds

|

4 baths

|

3,221 sq ft

|

House

677 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Sun City Center 708 RUTGERS PL, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$225,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

708 RUTGERS PL, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Highlands Ridge 5056 BIRKDALE DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$294,900

2 beds

|

2 baths

|

1,799 sq ft

|

Villa

5056 BIRKDALE DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Spruce Creek Country Club 9019 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$429,000

3 beds

|

2 baths

|

2,419 sq ft

|

House

9019 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2475 LAUREL BAY LN, THE VILLAGES, FL, 32..., The Villages, FL 32162
$229,900

2 beds

|

2 baths

|

1,156 sq ft

|

House

2475 LAUREL BAY LN, THE VILLAGES, FL, 32...
Community: The Villages®
Sun City Center 1417 INGRAM DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$208,500

2 beds

|

2 baths

|

1,857 sq ft

|

Villa

1417 INGRAM DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center

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