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Winter Haven, FL 55+ active adult communities & homes for sale - Page 2

137 homes near Winter Haven

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3.8 rating (5 reviews) Traditions at Lake Ruby
$200Ks - $400Ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 homes
Vienna Square
$200Ks - $300Ks
Vienna Square, Winter Haven, FL
New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes
Spring Lake Towers
$100Ks
Spring Lake Towers, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes
The Wellington
$100Ks - $200Ks
The Wellington, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1969 - 1981 | 77 homes
Poinsettia Heights
$100Ks - $200Ks
Poinsettia Heights, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Oakview
$100Ks - $200Ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
Preserve at Lakeside Land...
$300Ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 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
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
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 (4 reviews) High Vista at Ridgewood L...
$200Ks - $300Ks
High Vista at Ridgewood L..., Davenport, FL
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 623 homes
Lake Henry Estates
$200Ks
Lake Henry Estates, Haines City, FL
Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes
Carlsberg Estates on Lake...
$200Ks - $300Ks
Carlsberg Estates on Lake..., Lake Wales, FL
Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 homes
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Carlsberg Estates on Lake Suzanne 246 CHALET ESTATES ST, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$242,000

2 beds

|

2 baths

|

1,385 sq ft

|

House

246 CHALET ESTATES ST, LAKE WALES, FL, 3...
Lake Ashton 4249 BERWICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$389,900

2 beds

|

2 baths

|

1,847 sq ft

|

House

4249 BERWICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
New Lake Ashton 4577 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$375,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

4577 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
New Lake Ashton 4193 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$465,000

3 beds

|

3 baths

|

2,639 sq ft

|

House

4193 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
New Lake Ashton 4016 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$379,900

3 beds

|

2 baths

|

2,120 sq ft

|

House

4016 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Lake Ashton 1124 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$378,000

3 beds

|

2 baths

|

2,113 sq ft

|

House

1124 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
High Vista at Ridgewood Lakes 116 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$320,000

2 beds

|

2 baths

|

1,776 sq ft

|

House

116 FLEMING LN, DAVENPORT, FL, 33837
Del Webb Orlando 507 CADIZ DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$420,900

4 beds

|

3 baths

|

2,616 sq ft

|

House

507 CADIZ DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Lake Ashton 4068 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$495,000

3 beds

|

2 baths

|

2,064 sq ft

|

House

4068 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
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.
High Vista at Ridgewood Lakes 537 RIDGE VIEW DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$350,000

2 beds

|

2 baths

|

1,797 sq ft

|

House

537 RIDGE VIEW DR, DAVENPORT, FL, 33837
Del Webb Orlando 672 CORDOBA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$389,900

2 beds

|

2 baths

|

1,956 sq ft

|

House

672 CORDOBA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Lake Ashton 4188 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$290,000

2 beds

|

2 baths

|

1,520 sq ft

|

House

4188 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
Lake Ashton 4232 ROEBELENII DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$344,900

3 beds

|

2 baths

|

1,941 sq ft

|

House

4232 ROEBELENII DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Lake Ashton 5353 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$499,000

3 beds

|

2 baths

|

2,805 sq ft

|

House

5353 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Traditions at Lake Ruby 4016 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$421,900

4 beds

|

3 baths

|

1,927 sq ft

|

House

4016 CARTERET DR, WINTER HAVEN, FL, 3388...
Lake Ashton 4576 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$344,500

2 beds

|

2 baths

|

1,514 sq ft

|

House

4576 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
Vienna Square 1614 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$225,000

2 beds

|

2 baths

|

1,164 sq ft

|

Villa

1614 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
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.
Lake Ashton 1069 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$345,000

2 beds

|

2 baths

|

1,688 sq ft

|

House

1069 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Spring Lake Towers 700 MIRROR TER 702, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$117,900

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

700 MIRROR TER 702, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
Traditions at Lake Ruby 3832 TRADITIONS BLVD, WINTER HAVEN, FL, ..., Winter Haven, FL 33884
$300,000

3 beds

|

2 baths

|

2,109 sq ft

|

House

3832 TRADITIONS BLVD, WINTER HAVEN, FL, ...
Lake Ashton 5200 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$539,000

3 beds

|

2 baths

|

2,443 sq ft

|

House

5200 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Lake Ashton 4240 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$550,000

2 beds

|

2 baths

|

1,771 sq ft

|

House

4240 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Vienna Square 1703 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$259,000

2 beds

|

2 baths

|

1,164 sq ft

|

Villa

1703 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
High Vista at Ridgewood Lakes 642 VISTA OAKS WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$324,000

3 beds

|

2 baths

|

1,781 sq ft

|

House

642 VISTA OAKS WAY, DAVENPORT, FL, 33837
Del Webb Orlando 224 GRANADA LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$439,900

3 beds

|

2 baths

|

1,926 sq ft

|

House

224 GRANADA LN, DAVENPORT, FL, 33837
Community: Del Webb Orlando
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.
Lake Ashton 4139 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$319,900

2 beds

|

2 baths

|

1,556 sq ft

|

House

4139 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Lake Ashton 4148 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$570,000

3 beds

|

3 baths

|

2,808 sq ft

|

House

4148 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Lake Ashton 4072 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$355,000

3 beds

|

2 baths

|

1,820 sq ft

|

House

4072 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Spring Lake Towers 700 MIRROR TER 404, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$148,000

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

700 MIRROR TER 404, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
High Vista at Ridgewood Lakes 46 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$349,000

3 beds

|

2 baths

|

1,816 sq ft

|

House

46 HIGH VISTA DR, DAVENPORT, FL, 33837
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Carlsberg Estates on Lake Suzanne 284 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$218,900

2 beds

|

2 baths

|

1,170 sq ft

|

House

284 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Traditions at Lake Ruby 4150 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$272,900

3 beds

|

2 baths

|

1,831 sq ft

|

House

4150 BEDFORD AVE, WINTER HAVEN, FL, 3388...
High Vista at Ridgewood Lakes 247 TRAVIS LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$289,900

2 beds

|

2 baths

|

1,596 sq ft

|

House

247 TRAVIS LN, DAVENPORT, FL, 33837
High Vista at Ridgewood Lakes 205 CUNNINGHAM DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,000

3 beds

|

2 baths

|

2,502 sq ft

|

House

205 CUNNINGHAM 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.
High Vista at Ridgewood Lakes 100 MOSS LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,000

3 beds

|

2 baths

|

2,051 sq ft

|

House

100 MOSS LN, DAVENPORT, FL, 33837
High Vista at Ridgewood Lakes 106 MOSSY OAK DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$360,000

3 beds

|

2 baths

|

1,797 sq ft

|

House

106 MOSSY OAK DR, DAVENPORT, FL, 33837
Lake Ashton 4433 VENTANA LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$479,900

3 beds

|

2 baths

|

2,512 sq ft

|

House

4433 VENTANA LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Lake Henry Estates 669 WATERFORD DR, HAINES CITY, FL, 33844, Haines City, FL 33844
$232,000

3 beds

|

2 baths

|

1,741 sq ft

|

House

669 WATERFORD DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Carlsberg Estates on Lake Suzanne 4189 CANNES AVE, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$250,000

3 beds

|

2 baths

|

1,385 sq ft

|

House

4189 CANNES AVE, LAKE WALES, FL, 33859
Lake Henry Estates 497 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$280,000

2 beds

|

2 baths

|

1,747 sq ft

|

House

497 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
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