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

Living in Winter Haven

Winter Haven is a city in Polk County, Florida and located 51 miles east of Tampa. The canal-linked Chain of Lakes offer several waterside parks to bask in the sun with eateries…

Winter Haven is a city in Polk County, Florida and located 51 miles east of Tampa. The canal-linked Chain of Lakes offer several waterside parks to bask in the sun with eateries to visit making Winter Haven an ideal city for retirees.

Winter Haven Climate & Geography

Winter Haven is located in the humid subtropical zone. The average annual high temperature is in the low 80s and the average annual low temperature is in the low 60s. The summer months tend to be the rainiest time of year with an average annual rainfall around 50 inches.

Recreation, Culture & Entertainment In Winter Haven

Residents enjoy visiting Marshall Hampton Reserve, the trails are easy to access for leisurely strolls and bike rides. There are a few antique shops throughout the city to explore. Bok Tower Gardens, located about 15 miles outside Winter Haven, is 250-acre with a trail to bird watch and take in the scenery. There is a good amount of restaurants to wine & dine, a few offer darts and billiards.

Winter Haven Cost of Living & Taxes

The median home cost in Winter Haven is right at the national median. Florida is one of the few states with no income tax. Florida residents ages 65 and older who meet certain income limits can receive an extra homestead exemption equal to the assessed value of property. Social Security and other retirement income is not taxed.

Health Care In Winter Haven

Winter Haven Hospital is the one medical center and hospital located directly in Winter Haven. It’s ranked High Performing in four adult procedures including heart failure and hip replacement.

Frequently Asked Questions


171 homes near Winter Haven

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5 rating (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
4.4 rating (16 reviews) Del Webb Orlando
$200ks - $500ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
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
3.8 rating (5 reviews) Traditions at Lake Ruby
$200ks - $300ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 homes
Lake Henry Estates
$100ks - $300ks
Lake Henry Estates, Haines City, FL
Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Vienna Square
$100ks - $200ks
Vienna Square, Winter Haven, FL
New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes
Carlsberg Estates on Lake...
$200ks
Carlsberg Estates on Lake..., Lake Wales, FL
Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 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
Preserve at Lakeside Land...
$200ks - $300ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 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.
Oakview
$100ks - $200ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
Poinsettia Heights
$100ks - $200ks
Poinsettia Heights, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes
Lake Ashton 4193 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$535,000

3 beds

|

2 baths

|

2,058 sq ft

|

House

4193 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Carlsberg Estates on Lake Suzanne 364 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$284,900

2 beds

|

2 baths

|

1,387 sq ft

|

House

364 LAKE SUZANNE DR, LAKE WALES, FL, 338...
New Del Webb Orlando 120 MONTORO LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$289,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

120 MONTORO LN, DAVENPORT, FL, 33837
Community: Del Webb Orlando
New Del Webb Orlando 325 ALICANTE CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$370,000

3 beds

|

2 baths

|

2,056 sq ft

|

House

325 ALICANTE CT, DAVENPORT, FL, 33837
Community: Del Webb Orlando
New Del Webb Orlando 492 PONTEVEDRA RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$459,000

3 beds

|

3 baths

|

2,841 sq ft

|

House

492 PONTEVEDRA RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
New Del Webb Orlando 1032 SALAMANCA PL, DAVENPORT, FL, 33837, Davenport, FL 33837
$307,000

2 beds

|

2 baths

|

1,455 sq ft

|

House

1032 SALAMANCA PL, DAVENPORT, FL, 33837
Community: Del Webb Orlando
New
Cindy Certified
764 GREENWAY BLVD, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$257,990

3 beds

|

2 baths

|

1,328 sq ft

|

House

764 GREENWAY BLVD, LAKE WALES, FL, 33859
New
Cindy Certified
1163 AMBER WAVES CT, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$259,990

5 beds

|

2 baths

|

1,739 sq ft

|

House

1163 AMBER WAVES CT, LAKE WALES, FL, 338...
New
Cindy Certified
1167 AMBER WAVES CT, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$241,990

3 beds

|

2 baths

|

1,223 sq ft

|

House

1167 AMBER WAVES CT, LAKE WALES, FL, 338...
New
Cindy Certified
1158 AMBER WAVES CT, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$235,990

3 beds

|

2 baths

|

1,223 sq ft

|

House

1158 AMBER WAVES CT, 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 High Vista at Ridgewood Lakes 228 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$269,900

3 beds

|

2 baths

|

1,476 sq ft

|

House

228 FLEMING LN, DAVENPORT, FL, 33837
New
Cindy Certified
2433 AVENUE F NW, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880
$294,997

3 beds

|

2 baths

|

1,270 sq ft

|

House

2433 AVENUE F NW, WINTER HAVEN, FL, 3388...
Lake Ashton 6216 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$429,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

6216 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Lake Ashton 5288 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$314,000

3 beds

|

2 baths

|

1,847 sq ft

|

House

5288 GREEN DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Cindy Certified
988 CAMBRIDGE DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33881
$299,900

4 beds

|

2 baths

|

1,867 sq ft

|

House

988 CAMBRIDGE DR, WINTER HAVEN, FL, 3388...
Cindy Certified
414 TAFT DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$385,000

3 beds

|

2 baths

|

1,968 sq ft

|

House

414 TAFT DR, DAVENPORT, FL, 33837
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Lake Ashton 4227 BERWICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$359,000

3 beds

|

2 baths

|

1,847 sq ft

|

House

4227 BERWICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Del Webb Orlando 533 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$330,000

2 beds

|

2 baths

|

1,728 sq ft

|

House

533 ARENA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Cindy Certified
4046 DINNER LAKE WAY, LAKE WALES, FL, 33..., Lake Wales, FL 33859
$360,000

4 beds

|

2 baths

|

2,752 sq ft

|

House

4046 DINNER LAKE WAY, LAKE WALES, FL, 33...
Lake Ashton 5344 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$310,000

3 beds

|

2 baths

|

1,680 sq ft

|

House

5344 NICKLAUS DR, WINTER HAVEN, FL, 3388...
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.
Lake Ashton 4232 DORNOCH DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$449,000

3 beds

|

2 baths

|

2,229 sq ft

|

House

4232 DORNOCH DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Del Webb Orlando 123 MAGELLAN CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$514,900

3 beds

|

3 baths

|

2,186 sq ft

|

House

123 MAGELLAN CT, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Del Webb Orlando 336 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$424,900

3 beds

|

3 baths

|

2,086 sq ft

|

House

336 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Traditions at Lake Ruby 4035 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$249,900

2 beds

|

2 baths

|

1,719 sq ft

|

House

4035 CARTERET DR, WINTER HAVEN, FL, 3388...
Cindy Certified
3101 ROYAL TERN DR, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$279,990

4 beds

|

2 baths

|

1,851 sq ft

|

House

3101 ROYAL TERN DR, WINTER HAVEN, FL, 33...
Carlsberg Estates on Lake Suzanne 483 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$248,000

3 beds

|

2 baths

|

1,510 sq ft

|

House

483 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Del Webb Orlando 475 PALENCIA PL, DAVENPORT, FL, 33837, Davenport, FL 33837
$414,900

3 beds

|

2 baths

|

2,042 sq ft

|

House

475 PALENCIA PL, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Lake Ashton 1321 OAKMONT DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$424,900

3 beds

|

2 baths

|

2,312 sq ft

|

House

1321 OAKMONT DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Cindy Certified
469 NOVA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$320,000

3 beds

|

2 baths

|

1,694 sq ft

|

House

469 NOVA DR, DAVENPORT, FL, 33837
High Vista at Ridgewood Lakes 217 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$324,750

2 beds

|

2 baths

|

1,790 sq ft

|

House

217 FLEMING LN, 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.
Cindy Certified
2441 OAKWOOD LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$339,000

3 beds

|

2 baths

|

1,420 sq ft

|

House

2441 OAKWOOD LN, DAVENPORT, FL, 33837
Cindy Certified
6283 RED HERRING DR, WINTER HAVEN, FL, 3..., Winter Haven, FL 33881
$275,000

3 beds

|

2 baths

|

1,747 sq ft

|

House

6283 RED HERRING DR, WINTER HAVEN, FL, 3...
Lake Ashton 5281 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$279,900

3 beds

|

2 baths

|

1,495 sq ft

|

House

5281 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Lake Ashton 4047 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$349,900

3 beds

|

2 baths

|

1,905 sq ft

|

House

4047 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Lake Henry Estates 430 HARBOURVIEW DR, HAINES CITY, FL, 338..., Haines City, FL 33844
$332,900

2 beds

|

2 baths

|

1,650 sq ft

|

House

430 HARBOURVIEW DR, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Vienna Square 1631 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$190,500

2 beds

|

2 baths

|

1,231 sq ft

|

Villa

1631 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Lake Ashton 4028 PHOENICIAN WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$330,000

2 beds

|

2 baths

|

1,784 sq ft

|

House

4028 PHOENICIAN WAY, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Lake Ashton 4064 PHOENICIAN WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$449,900

3 beds

|

2 baths

|

2,354 sq ft

|

House

4064 PHOENICIAN WAY, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Lake Ashton 4039 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$369,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

4039 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
Carlsberg Estates on Lake Suzanne 452 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$399,000

3 beds

|

2 baths

|

1,979 sq ft

|

House

452 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.
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