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

132 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

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

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

Vienna Square

$100ks - $200ks

Vienna Square, Winter Haven, FL

New and Resale | 55+ age-restricted | Built 2007 - present | 181 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

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Questions? Call us: (863) 656-3786

Carlsberg Estates on Lake...

$200ks

Carlsberg Estates on Lake..., Lake Wales, FL

Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 homes

Lake Henry Estates

$100ks - $300ks

Lake Henry Estates, Haines City, FL

Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes

Spring Lake Towers

$100ks

Spring Lake Towers, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes

Oakview

$100ks - $200ks

Oakview, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 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.

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

Poinsettia Heights

$100ks - $200ks

Poinsettia Heights, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes

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Questions? Call us: (863) 656-3786

New Lake Ashton

4433 VENTANA LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$469,900

3 beds

2 baths

2,512 sq ft

House

4433 VENTANA LN, LAKE WALES, FL, 33859

Community: Lake Ashton

New Lake Ashton

4331 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$289,000

3 beds

2 baths

1,457 sq ft

House

4331 ASHTON CLUB DR, LAKE WALES, FL, 338...

Community: Lake Ashton

Oakview

$219,900

2 beds

2 baths

1,220 sq ft

Villa

1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388...

Community: Oakview

High Vista at Ridgewood Lakes

823 CUNNINGHAM DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$279,000

2 beds

2 baths

1,693 sq ft

House

823 CUNNINGHAM DR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

Lake Ashton

5264 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$335,000

3 beds

2 baths

2,011 sq ft

House

5264 GREEN DR, WINTER HAVEN, FL, 33884

Community: Lake Ashton

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Questions? Call us: (863) 656-3786

Lake Ashton

4648 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$375,000

3 beds

2 baths

1,847 sq ft

House

4648 TURNBERRY LN, LAKE WALES, FL, 33859

Community: Lake Ashton

Lake Ashton

4144 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$265,000

2 beds

2 baths

1,503 sq ft

House

4144 ABERDEEN LN, LAKE WALES, FL, 33859

Community: Lake Ashton

Lake Ashton

4080 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859

$379,900

3 beds

2 baths

2,295 sq ft

House

4080 SABLE LOOP DR, LAKE WALES, FL, 3385...

Community: Lake Ashton

Preserve at Lakeside Landings

5828 MARSH LANDING DR, WINTER HAVEN, FL,..., Winter Haven, FL 33881

$387,500

4 beds

2 baths

2,078 sq ft

House

5828 MARSH LANDING DR, WINTER HAVEN, FL,...

Community: Preserve at Lakeside Landings

Traditions at Lake Ruby

3343 LIVINGSTON WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884

$225,000

2 beds

2 baths

1,118 sq ft

House

3343 LIVINGSTON WAY, WINTER HAVEN, FL, 3...

Community: Traditions at Lake Ruby

Del Webb Orlando

329 ALICANTE CT, DAVENPORT, FL, 33837, Davenport, FL 33837

$415,000

3 beds

2 baths

2,000 sq ft

House

329 ALICANTE CT, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Traditions at Lake Ruby

4064 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$279,000

2 beds

2 baths

1,519 sq ft

House

4064 CARTERET DR, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

Lake Ashton

4083 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$535,000

3 beds

2 baths

2,477 sq ft

House

4083 ASHTON CLUB DR, LAKE WALES, FL, 338...

Community: Lake Ashton

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

Questions? Call us: (863) 656-3786

Traditions at Lake Ruby

3588 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$274,995

2 beds

2 baths

1,719 sq ft

House

3588 RALEIGH DR, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Del Webb Orlando

501 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$456,500

3 beds

2 baths

2,249 sq ft

House

501 ARENA DR, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Traditions at Lake Ruby

3007 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$210,000

2 beds

2 baths

1,385 sq ft

Villa

3007 CANEEL ST, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Lake Ashton

6216 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884

$459,000

3 beds

2 baths

2,045 sq ft

House

6216 PINEHURST LOOP, WINTER HAVEN, FL, 3...

Community: Lake Ashton

Lake Ashton

4424 WATERFORD DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$300,000

2 beds

2 baths

1,530 sq ft

House

4424 WATERFORD DR, LAKE WALES, FL, 33859

Community: Lake Ashton

Traditions at Lake Ruby

3008 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$210,000

2 beds

2 baths

1,385 sq ft

Villa

3008 CANEEL ST, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Lake Ashton

4425 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$329,900

3 beds

2 baths

1,706 sq ft

House

4425 TURNBERRY LN, LAKE WALES, FL, 33859

Community: Lake Ashton

Lake Ashton

4191 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$369,900

3 beds

2 baths

2,229 sq ft

House

4191 ABERDEEN LN, 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

1033 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$389,000

3 beds

2 baths

1,879 sq ft

House

1033 SAWGRASS DR, WINTER HAVEN, FL, 3388...

Community: Lake Ashton

Lake Ashton

4033 PHOENICIAN WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884

$424,900

3 beds

2 baths

2,095 sq ft

House

4033 PHOENICIAN WAY, WINTER HAVEN, FL, 3...

Community: Lake Ashton

Lake Ashton

1166 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$460,000

3 beds

2 baths

2,045 sq ft

House

1166 SAWGRASS DR, WINTER HAVEN, FL, 3388...

Community: Lake Ashton

Carlsberg Estates on Lake Suzanne

341 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$240,000

2 beds

2 baths

1,385 sq ft

House

341 LAKE SUZANNE DR, LAKE WALES, FL, 338...

Community: Carlsberg Estates on Lake Suzanne

Del Webb Orlando

516 PAMPLONA PL, DAVENPORT, FL, 33837, Davenport, FL 33837

$319,900

2 beds

2 baths

1,445 sq ft

House

516 PAMPLONA PL, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Lake Ashton

4632 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$429,900

3 beds

2 baths

2,354 sq ft

House

4632 TURNBERRY LN, LAKE WALES, FL, 33859

Community: Lake Ashton

Lake Ashton

4189 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859

$735,000

3 beds

2 baths

2,478 sq ft

House

4189 STONE CREEK LOOP, LAKE WALES, FL, 3...

Community: Lake Ashton

Lake Ashton

4360 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$399,900

3 beds

2 baths

2,265 sq ft

House

4360 ASHTON CLUB DR, LAKE WALES, FL, 338...

Community: Lake Ashton

Lake Henry Estates

422 HARBOURVIEW DR, HAINES CITY, FL, 338..., Haines City, FL 33844

$289,900

3 beds

2 baths

1,793 sq ft

House

422 HARBOURVIEW DR, 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

1209 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$450,000

3 beds

2 baths

2,045 sq ft

House

1209 SAWGRASS DR, WINTER HAVEN, FL, 3388...

Community: Lake Ashton

Vienna Square

2349 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884

$319,900

3 beds

3 baths

1,724 sq ft

House

2349 SALZBURG LOOP, WINTER HAVEN, FL, 33...

Community: Vienna Square

Del Webb Orlando

799 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837

$281,900

2 beds

2 baths

1,281 sq ft

House

799 ASTURIAS RD, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Traditions at Lake Ruby

3342 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$240,000

2 beds

2 baths

1,185 sq ft

House

3342 RALEIGH DR, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Oakview

$224,900

2 beds

2 baths

1,438 sq ft

House

1518 OAKVIEW CIR, WINTER HAVEN, FL, 3388...

Community: Oakview

Lake Henry Estates

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

$279,900

3 beds

2 baths

1,835 sq ft

House

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

Community: Lake Henry Estates

Lake Ashton

6308 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884

$464,900

3 beds

2 baths

2,045 sq ft

House

6308 PINEHURST LOOP, WINTER HAVEN, FL, 3...

Community: Lake Ashton

Traditions at Lake Ruby

2872 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884

$212,500

2 beds

2 baths

1,517 sq ft

Villa

2872 ATTWATER LOOP, WINTER HAVEN, FL, 33...

Community: Traditions at Lake Ruby

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

Questions? Call us: (863) 656-3786

High Vista at Ridgewood Lakes

245 FITZGERALD LN, DAVENPORT, FL, 33837, Davenport, FL 33837

$285,000

2 beds

2 baths

1,388 sq ft

House

245 FITZGERALD LN, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

Traditions at Lake Ruby

2733 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884

$361,696

3 beds

3 baths

2,032 sq ft

House

2733 ATTWATER LOOP, WINTER HAVEN, FL, 33...

Community: Traditions at Lake Ruby

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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.

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132 homes

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

12 communities near Winter Haven

132 homes near Winter Haven

3 beds

2 baths

2,512 sq ft

House

3 beds

2 baths

1,457 sq ft

House

2 beds

2 baths

1,220 sq ft

Villa

2 beds

2 baths

1,693 sq ft

House

3 beds

2 baths

2,011 sq ft

House

3 beds

2 baths

1,847 sq ft

House

2 beds

2 baths

1,503 sq ft

House

3 beds

2 baths

2,295 sq ft

House

4 beds

2 baths

2,078 sq ft

House

2 beds

2 baths

1,118 sq ft

House

3 beds

2 baths

2,000 sq ft

House

2 beds

2 baths

1,519 sq ft

House

3 beds

2 baths

2,477 sq ft

House

2 beds

2 baths

1,719 sq ft

House

3 beds

2 baths

2,249 sq ft

House

2 beds

2 baths

1,385 sq ft

Villa

3 beds

2 baths

2,045 sq ft

House

2 beds

2 baths

1,530 sq ft

House

2 beds

2 baths

1,385 sq ft

Villa

3 beds