Call us at (863) 656-3786 to learn more about active adult communities in Winter Haven

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


12 communities near Winter Haven

Sort by:

Relevance

Relevance

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
Oakview
$100ks - $200ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
The Wellington
$100ks - $200ks
The Wellington, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1969 - 1981 | 77 homes
Spring Lake Towers
$100ks
Spring Lake Towers, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 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.
Preserve at Lakeside Land...
$200ks - $300ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 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 Lake Ashton 3064 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$399,900

3 beds

|

2 baths

|

2,394 sq ft

|

House

3064 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
New Del Webb Orlando 542 CORTEZ DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,900

3 beds

|

2 baths

|

1,928 sq ft

|

House

542 CORTEZ DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
New Vienna Square 1643 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$197,000

2 beds

|

2 baths

|

1,369 sq ft

|

Villa

1643 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
New
Cindy Certified
735 JEFFERSON ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$314,990

4 beds

|

2 baths

|

1,767 sq ft

|

House

735 JEFFERSON ST, DAVENPORT, FL, 33837
Lake Ashton 3833 LITCHFIELD LOOP, LAKE WALES, FL, 33..., Lake Wales, FL 33859
$500,000

2 beds

|

2 baths

|

1,763 sq ft

|

House

3833 LITCHFIELD LOOP, LAKE WALES, FL, 33...
Community: Lake Ashton
Cindy Certified
4462 EMERALD PALMS LN, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$975,000

4 beds

|

3 baths

|

2,825 sq ft

|

House

4462 EMERALD PALMS LN, WINTER HAVEN, FL,...
Cindy Certified
756 GREENWAY BLVD, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$289,990

5 beds

|

2 baths

|

1,708 sq ft

|

House

756 GREENWAY BLVD, LAKE WALES, FL, 33859
High Vista at Ridgewood Lakes 124 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$275,000

3 beds

|

2 baths

|

1,542 sq ft

|

House

124 HIGH VISTA 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.
Cindy Certified
1859 GALLOWAY TER, WINTER HAVEN, FL, 338..., Winter Haven, FL 33881
$350,000

4 beds

|

2 baths

|

2,103 sq ft

|

House

1859 GALLOWAY TER, WINTER HAVEN, FL, 338...
Cindy Certified
417 HENNEPIN LOOP, LAKE WALES, FL, 33898, Lake Wales, FL 33898
$247,999

3 beds

|

2 baths

|

1,420 sq ft

|

House

417 HENNEPIN LOOP, LAKE WALES, FL, 33898
Traditions at Lake Ruby 3437 GRENVILLE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$223,000

2 beds

|

2 baths

|

1,275 sq ft

|

House

3437 GRENVILLE DR, WINTER HAVEN, FL, 338...
Lake Ashton 6240 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$415,000

3 beds

|

2 baths

|

2,057 sq ft

|

House

6240 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
High Vista at Ridgewood Lakes 159 RED MAPLE PASS, DAVENPORT, FL, 33837, Davenport, FL 33837
$299,900

2 beds

|

2 baths

|

1,693 sq ft

|

House

159 RED MAPLE PASS, DAVENPORT, FL, 33837
High Vista at Ridgewood Lakes 148 RED MAPLE PASS, DAVENPORT, FL, 33837, Davenport, FL 33837
$339,900

2 beds

|

2 baths

|

2,003 sq ft

|

House

148 RED MAPLE PASS, DAVENPORT, FL, 33837
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Lake Henry Estates 686 PARADISE PT, HAINES CITY, FL, 33844, Haines City, FL 33844
$249,000

2 beds

|

2 baths

|

1,418 sq ft

|

House

686 PARADISE PT, HAINES CITY, FL, 33844
Community: Lake Henry Estates
Vienna Square 2470 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$270,000

3 beds

|

2 baths

|

1,935 sq ft

|

House

2470 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
Cindy Certified
915 HART LAKE CT, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$520,000

4 beds

|

3 baths

|

2,659 sq ft

|

House

915 HART LAKE CT, WINTER HAVEN, FL, 3388...
Del Webb Orlando 516 PLAYA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,999

2 beds

|

2 baths

|

2,030 sq ft

|

House

516 PLAYA DR, 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 6125 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$425,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

6125 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Lake Ashton 5385 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$369,000

3 beds

|

2 baths

|

1,847 sq ft

|

House

5385 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Lake Ashton 4299 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$415,000

3 beds

|

2 baths

|

2,229 sq ft

|

House

4299 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
Del Webb Orlando 516 LAGO LOOP, DAVENPORT, FL, 33837, Davenport, FL 33837
$391,000

3 beds

|

2 baths

|

1,693 sq ft

|

House

516 LAGO LOOP, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Cindy Certified
168 WATERSIDE CIR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33880
$299,900

3 beds

|

2 baths

|

1,714 sq ft

|

House

168 WATERSIDE CIR, WINTER HAVEN, FL, 338...
Del Webb Orlando 283 TOMELLOSO WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$308,753

2 beds

|

2 baths

|

1,425 sq ft

|

House

283 TOMELLOSO WAY, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Del Webb Orlando 521 VISTA SOL DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$309,900

2 beds

|

2 baths

|

1,446 sq ft

|

House

521 VISTA SOL DR, 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
Del Webb Orlando 536 GRANDE DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$375,000

3 beds

|

3 baths

|

2,263 sq ft

|

House

536 GRANDE DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Traditions at Lake Ruby 4043 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$359,900

2 beds

|

2 baths

|

1,871 sq ft

|

House

4043 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Cindy Certified
1358 BUCKEYE TRACE BLVD, WINTER HAVEN, F..., Winter Haven, FL 33881
$270,000

3 beds

|

2 baths

|

1,820 sq ft

|

House

1358 BUCKEYE TRACE BLVD, WINTER HAVEN, F...
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
2021 CANTON PARK DR, WINTER HAVEN, FL, 3..., Winter Haven, FL 33881
$325,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

2021 CANTON PARK DR, WINTER HAVEN, FL, 3...
Cindy Certified
3447 HAVEN SIDE RD ROAD, DAVENPORT, FL, ..., Davenport, FL 33837
$457,090

4 beds

|

3 baths

|

2,503 sq ft

|

House

3447 HAVEN SIDE RD ROAD, DAVENPORT, FL, ...
Cindy Certified
3451 HAVEN SIDE RD ROAD, DAVENPORT, FL, ..., Davenport, FL 33837
$459,090

4 beds

|

3 baths

|

2,503 sq ft

|

House

3451 HAVEN SIDE RD ROAD, DAVENPORT, FL, ...
Cindy Certified
1652 LEMON AVE, WINTER HAVEN, FL, 33881, Winter Haven, FL 33881
$380,000

4 beds

|

3 baths

|

2,509 sq ft

|

House

1652 LEMON AVE, WINTER HAVEN, FL, 33881
Lake Ashton 3834 LITCHFIELD LOOP, LAKE WALES, FL, 33..., Lake Wales, FL 33859
$589,999

2 beds

|

2 baths

|

1,792 sq ft

|

House

3834 LITCHFIELD LOOP, LAKE WALES, FL, 33...
Community: Lake Ashton
Lake Ashton 4497 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$359,000

3 beds

|

2 baths

|

2,312 sq ft

|

House

4497 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
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
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
Want to learn more about 55+ communities in Winter Haven? 55places can help!
Questions? Call us: (863) 656-3786
Del Webb Orlando 492 PONTEVEDRA RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$439,000

3 beds

|

3 baths

|

2,841 sq ft

|

House

492 PONTEVEDRA RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
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
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.

Frequently Asked Questions


Want more information about active adult communities around Winter Haven?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Winter Haven?

Call us: (863) 656-3786
12 communities
Remove Boundaries ×
Map Satellite

Reinmlsx

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Nov 03, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top