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

137 homes near Winter Haven

Sort by:

Relevance

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!

656 SWEETWATER WAY, HAINES CITY, FL, 338...

Community: Lake Henry Estates

Want to learn more about 55+ communities in Winter Haven? 55places can help!

Questions? Call us: (863) 656-3786

Lake Ashton

1142 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$464,900

3 beds

2 baths

2,045 sq ft

House

1142 SAWGRASS DR, WINTER HAVEN, FL, 3388...

Community: Lake Ashton

Traditions at Lake Ruby

3738 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$329,000

2 beds

2 baths

1,797 sq ft

House

3738 PLYMOUTH DR, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

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...

Community: Carlsberg Estates on Lake Suzanne

High Vista at Ridgewood Lakes

457 GOLF VISTA CIR, DAVENPORT, FL, 33837, Davenport, FL 33837

$395,000

4 beds

3 baths

2,211 sq ft

House

457 GOLF VISTA CIR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

Lake Ashton

5384 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$365,000

2 beds

2 baths

1,682 sq ft

House

5384 HOGAN LN, WINTER HAVEN, FL, 33884

Community: Lake Ashton

Del Webb Orlando

613 CANTABRIA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$399,900

2 beds

2 baths

1,831 sq ft

House

613 CANTABRIA DR, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Del Webb Orlando

710 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837

$434,900

2 beds

2 baths

2,080 sq ft

House

710 ASTURIAS 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

Del Webb Orlando

536 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$309,900

3 beds

2 baths

1,508 sq ft

House

536 ARENA DR, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Del Webb Orlando

336 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837

$429,900

3 beds

3 baths

2,086 sq ft

House

336 DEL SOL AVE, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Del Webb Orlando

451 PALENCIA PL, DAVENPORT, FL, 33837, Davenport, FL 33837

$459,900

3 beds

2 baths

2,182 sq ft

House

451 PALENCIA PL, DAVENPORT, FL, 33837

Community: Del Webb Orlando

New Vienna Square

1620 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$229,000

2 beds

2 baths

1,329 sq ft

Villa

1620 LINZ CT, WINTER HAVEN, FL, 33884

Community: Vienna Square

Traditions at Lake Ruby

3614 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$320,000

3 beds

2 baths

2,109 sq ft

House

3614 PLYMOUTH DR, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

Traditions at Lake Ruby

3986 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$399,900

4 beds

3 baths

2,320 sq ft

House

3986 BEDFORD AVE, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

New Lake Henry Estates

516 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844

$244,990

2 beds

2 baths

1,393 sq ft

House

516 SWEETWATER WAY, HAINES CITY, FL, 338...

Community: Lake Henry Estates

Traditions at Lake Ruby

3348 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$235,000

2 beds

2 baths

1,185 sq ft

House

3348 RALEIGH DR, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Want to learn more about 55+ communities in Winter Haven? 55places can help!

Questions? Call us: (863) 656-3786

New Lake Ashton

4189 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$559,000

2 beds

2 baths

2,227 sq ft

House

4189 LIMERICK DR, LAKE WALES, FL, 33859

Community: Lake Ashton

Lake Ashton

4168 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$349,900

3 beds

2 baths

1,756 sq ft

House

4168 ABERDEEN LN, LAKE WALES, FL, 33859

Community: Lake Ashton

Lake Ashton

4025 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859

$575,000

4 beds

3 baths

2,923 sq ft

House

4025 SABLE LOOP DR, LAKE WALES, FL, 3385...

Community: Lake Ashton

Lake Ashton

5325 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$284,900

2 beds

2 baths

1,319 sq ft

House

5325 NICKLAUS DR, WINTER HAVEN, FL, 3388...

Community: Lake Ashton

New Lake Ashton

4081 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$405,000

3 beds

2 baths

2,027 sq ft

House

4081 DUNMORE DR, LAKE WALES, FL, 33859

Community: Lake Ashton

Traditions at Lake Ruby

2925 DAYTON DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$310,000

3 beds

2 baths

2,109 sq ft

House

2925 DAYTON DR, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Del Webb Orlando

300 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837

$428,200

2 beds

2 baths

1,728 sq ft

House

300 DEL SOL AVE, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Traditions at Lake Ruby

3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$388,900

4 beds

3 baths

2,404 sq ft

House

3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

Traditions at Lake Ruby

3987 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$358,000

2 beds

2 baths

1,817 sq ft

House

3987 BEDFORD AVE, WINTER HAVEN, FL, 3388...

House

514 SWEETWATER WAY, HAINES CITY, FL, 338...

Community: Lake Henry Estates

Want to learn more about 55+ communities in Winter Haven? 55places can help!

Questions? Call us: (863) 656-3786

Del Webb Orlando

210 TOMELLOSO WAY, DAVENPORT, FL, 33837, Davenport, FL 33837

$415,000

3 beds

3 baths

2,004 sq ft

House

210 TOMELLOSO WAY, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Lake Ashton

4115 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$295,000

2 beds

2 baths

1,688 sq ft

House

4115 ABERDEEN LN, LAKE WALES, FL, 33859

Community: Lake Ashton

1 2 3…4

Frequently Asked Questions

What size 55+ communities are there in Winter Haven?

In Winter Haven, there are no large communities, 1 medium community with 500-1000 homes, and 6 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winter Haven?

The smallest 55+ communities in Winter Haven has 44 homes, the largest has 552 homes, and the average communities consists of 147 homes.

Are there new 55+ homes available in Winter Haven?

Yes, there is new 55+ home available in Winter Haven. The most recent communities started in Winter Haven include Preserve at Lakeside Landings, Vienna Square, Traditions at Lake Ruby. There is also 1 communities in Winter Haven that offers new construction homes, including Vienna Square.

Are there gated 55+ communities in Winter Haven?

Yes, there are gated 55+ communities in Winter Haven. Approximately 42.9% of 55+ communities in the area are gated. For instance, Traditions at Lake Ruby is a gated communities with 552 homes, and Preserve at Lakeside Landings is another gated communities with 44 homes.

How long do listings in 55+ communities in Winter Haven typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Winter Haven stay on the market for around 237 days. The average price of homes for sale in these communities is approximately $221,827, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Preserve at Lakeside Landings average around $337,000, while homes in Oakview average around $207,537.

Want more information about active adult communities around Winter Haven?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

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 [email protected]. 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

137 homes

Remove Boundaries ×

Map Satellite

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: Jan 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

12 communities near Winter Haven

137 homes near Winter Haven

3 beds

2 baths

2,363 sq ft

House

3 beds

2 baths

2,051 sq ft

House

3 beds

3 baths

2,032 sq ft

House

3 beds

2 baths

1,999 sq ft

House

2 beds

2 baths

1,681 sq ft

House

3 beds

2 baths

2,045 sq ft

House

2 beds

2 baths

1,797 sq ft

House

3 beds

3 baths

2,371 sq ft

House

3 beds

3 baths

1,744 sq ft

House

4 beds

3 baths

2,211 sq ft

House

2 beds

2 baths

1,682 sq ft

House

2 beds

2 baths

1,831 sq ft

House

2 beds

2 baths

2,080 sq ft

House

3 beds

2 baths

1,508 sq ft

House

3 beds

3 baths

2,086 sq ft

House

3 beds

2 baths

2,182 sq ft

House

2 beds

2 baths

1,329 sq ft

Villa

3 beds

2 baths

2,109 sq ft

House

4 beds

3 baths

2,320 sq ft

House

2 beds