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

32 communities near Lakeland-Winter Haven Area

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Highland Fairways
$100ks - $300ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
5 rating (1 review) Cypress Lakes
$100ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
5 rating (1 review) Sandpiper Golf & Country ...
$100ks - $300ks
Sandpiper Golf & Country ..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
5 rating (4 reviews) Highlands Ridge
<$100k - $300ks
Highlands Ridge, Avon Park, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 850 homes
Want to learn more about 55+ communities in Lakeland-Winter Haven Area? 55places can help!
Questions? Call us: (863) 344-5798
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
5 rating (1 review) Silver Lakes
$100ks - $300ks
Silver Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1996 - 2001 | 148 homes
Lake Henry Estates
$100ks - $300ks
Lake Henry Estates, Haines City, FL
Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes
Colonnades
$100ks - $200ks
Colonnades, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 homes
Lake James
$300ks
Lake James, Lakeland, FL
New and Resale | 55+ age-restricted | Built 2004 - present | 216 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.
4.5 rating (19 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes
Tomoka Heights
$100ks - $300ks
Tomoka Heights, Lake Placid, FL
Resale Only | 55+ age-restricted | Built 1982 - 2018 | 460 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
Covered Bridge
$100ks
Covered Bridge, Lake Placid, FL
New and Resale | 55+ age-restricted | Built 1974 - present | 230 homes
Want to learn more about 55+ communities in Lakeland-Winter Haven Area? 55places can help!
Questions? Call us: (863) 344-5798
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 homes
Thunderbird Hill
$100ks - $200ks
Thunderbird Hill, Sebring, FL
Resale Only | 55+ age-restricted | Built 1984 - 2000 | 103 homes
Esplanade at Westview
$300ks - $700ks
Esplanade at Westview, Kissimmee, FL
New Construction | Age-targeted | Built 2025 - present | 600 homes
5 rating (4 reviews) Carillon Lakes
$200ks - $400ks
Carillon Lakes, Lakeland, FL
Resale Only | Age-targeted | Built 2000 - 2006 | 650 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.
Vienna Square
$100ks - $200ks
Vienna Square, Winter Haven, FL
New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes
3 rating (1 review) Cormorant Point
$100ks - $200ks
Cormorant Point, Sebring, FL
Resale Only | 55+ age-restricted | Built 1981 - 2007 | 150 homes
Carlsberg Estates on Lake...
$200ks
Carlsberg Estates on Lake..., Lake Wales, FL
Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 homes
Hidden Creek
$100ks - $200ks
Hidden Creek, Sebring, FL
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 55 homes
Spring Lake Towers
$100ks
Spring Lake Towers, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes
Lakes at Laurel Highlands
$200ks - $300ks
Lakes at Laurel Highlands, Lakeland, FL
New Construction | Age-targeted | Built 2017 - present | 65 homes
Oakview
$100ks - $200ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
Want to learn more about 55+ communities in Lakeland-Winter Haven Area? 55places can help!
Questions? Call us: (863) 344-5798
The Wellington
$100ks - $200ks
The Wellington, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1969 - 1981 | 77 homes
2 rating (1 review) Heritage Landings
$200ks - $300ks
Heritage Landings, Lakeland, FL
New Construction | 55+ age-restricted | Built 2017 - 2020 | 65 homes
Ashley Oaks
$100ks
Ashley Oaks, Sebring, FL
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 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.
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
Solivita 513 BARCELONA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$295,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

513 BARCELONA DR, KISSIMMEE, FL, 34759
Community: Solivita
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 Tohoqua Reserve 2711 SUMMER RETREAT LN, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$349,990

3 beds

|

2 baths

|

1,579 sq ft

|

Villa

2711 SUMMER RETREAT LN, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
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
Want to learn more about 55+ communities in Lakeland-Winter Haven Area? 55places can help!
Questions? Call us: (863) 344-5798
New Tomoka Heights 158 CRESTVIEW TER, LAKE PLACID, FL, 3385..., Lake Placid, FL 33852
$405,000

3 beds

|

2 baths

|

2,876 sq ft

|

House

158 CRESTVIEW TER, LAKE PLACID, FL, 3385...
Community: Tomoka Heights
New
Cindy Certified
4459 RIVER BIRCH BND, LAKELAND, FL, 3381..., Lakeland, FL 33811
$391,095

4 beds

|

2 baths

|

2,005 sq ft

|

House

4459 RIVER BIRCH BND, LAKELAND, FL, 3381...
New
Cindy Certified
4586 RIVER BIRCH BND, LAKELAND, FL, 3381..., Lakeland, FL 33811
$368,280

4 beds

|

2 baths

|

1,715 sq ft

|

House

4586 RIVER BIRCH BND, LAKELAND, FL, 3381...
New
Cindy Certified
4471 RIVER BIRCH BND, LAKELAND, FL, 3381..., Lakeland, FL 33811
$339,900

3 beds

|

2 baths

|

1,545 sq ft

|

House

4471 RIVER BIRCH BND, LAKELAND, FL, 3381...
New Tomoka Heights 9 ACACIA CT, LAKE PLACID, FL, 33852, Lake Placid, FL 33852
$375,000

2 beds

|

2 baths

|

1,750 sq ft

|

House

9 ACACIA CT, LAKE PLACID, FL, 33852
Community: Tomoka Heights
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 Colonnades 4930 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$186,900

2 beds

|

2 baths

|

1,300 sq ft

|

Manufactured Home

4930 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
New
Cindy Certified
4041 SHEARWATER ST, LAKELAND, FL, 33811, Lakeland, FL 33811
$444,900

4 beds

|

3 baths

|

2,370 sq ft

|

House

4041 SHEARWATER ST, LAKELAND, FL, 33811
New
Cindy Certified
5533 ISLA SAONA DR, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$341,467

4 beds

|

2 baths

|

1,813 sq ft

|

House

5533 ISLA SAONA DR, KISSIMMEE, FL, 34758
New Sandpiper Golf & Country Club 6380 EGRET DR 33, LAKELAND, FL, 33809, Lakeland, FL 33809
$249,000

2 beds

|

2 baths

|

1,112 sq ft

|

Villa

6380 EGRET DR 33, LAKELAND, FL, 33809
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
New
Cindy Certified
5515 ISLA SAONA DR, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$345,214

4 beds

|

2 baths

|

1,813 sq ft

|

House

5515 ISLA SAONA DR, KISSIMMEE, FL, 34758
Want to learn more about 55+ communities in Lakeland-Winter Haven Area? 55places can help!
Questions? Call us: (863) 344-5798
New Solivita 265 INDIAN WELLS AVE, POINCIANA, FL, 347..., Poinciana, FL 34759
$373,000

2 beds

|

2 baths

|

2,101 sq ft

|

House

265 INDIAN WELLS AVE, POINCIANA, FL, 347...
Community: Solivita
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
New
Cindy Certified
5685 SEAGRAPE LN, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$355,069

3 beds

|

3 baths

|

1,790 sq ft

|

House

5685 SEAGRAPE LN, KISSIMMEE, FL, 34758
New Highlands Ridge 2857 E SPINNAKER DR, AVON PARK, FL, 3382..., Avon Park, FL 33825
$74,900

2 beds

|

2 baths

|

1,232 sq ft

|

Mobile Home

2857 E SPINNAKER DR, AVON PARK, FL, 3382...
Community: Highlands Ridge
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
Cindy Certified
262 TANAGER AVE, SEBRING, FL, 33870, Sebring, FL 33870
$365,000

4 beds

|

3 baths

|

1,735 sq ft

|

House

262 TANAGER AVE, SEBRING, FL, 33870
New 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
New
Cindy Certified
242 ABBOTSBURY DR, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$375,000

3 beds

|

3 baths

|

1,622 sq ft

|

House

242 ABBOTSBURY DR, KISSIMMEE, FL, 34758
New
Cindy Certified
209 VANWALL TER, SEBRING, FL, 33872, Sebring, FL 33872
$369,000

3 beds

|

2 baths

|

1,422 sq ft

|

House

209 VANWALL TER, SEBRING, FL, 33872
New
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,...
New Sandpiper Golf & Country Club 5946 CHICKADEE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$364,500

3 beds

|

2 baths

|

1,852 sq ft

|

House

5946 CHICKADEE DR, LAKELAND, FL, 33809
New Tohoqua Reserve 2015 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$412,000

3 beds

|

2 baths

|

2,054 sq ft

|

House

2015 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Want to learn more about 55+ communities in Lakeland-Winter Haven Area? 55places can help!
Questions? Call us: (863) 344-5798
New
Cindy Certified
5755 MEADS BAY POND RD, KISSIMMEE, FL, 3..., Kissimmee, FL 34758
$387,530

4 beds

|

3 baths

|

2,175 sq ft

|

House

5755 MEADS BAY POND RD, KISSIMMEE, FL, 3...
New
Cindy Certified
5704 PORTICO PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$312,290

4 beds

|

2 baths

|

1,600 sq ft

|

House

5704 PORTICO PL, KISSIMMEE, FL, 34758
Tomoka Heights 38 HICKORY HILLS CIR, LAKE PLACID, FL, 3..., Lake Placid, FL 33852
$245,000

2 beds

|

2 baths

|

1,162 sq ft

|

Villa

38 HICKORY HILLS CIR, LAKE PLACID, FL, 3...
Community: Tomoka Heights
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.
Solivita 964 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$600,000

3 beds

|

3 baths

|

2,466 sq ft

|

House

964 SAN RAPHAEL ST, POINCIANA, FL, 34759
Community: Solivita
Thunderbird Hill 3916 THUNDERBIRD HILL CIR, SEBRING, FL, ..., Sebring, FL 33872
$190,000

2 beds

|

2 baths

|

1,103 sq ft

|

Townhouse

3916 THUNDERBIRD HILL CIR, SEBRING, FL, ...
Community: Thunderbird Hill
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
Solivita 296 BELLA CORTINA DR, POINCIANA, FL, 347..., Poinciana, FL 34759
$475,000

3 beds

|

2 baths

|

1,849 sq ft

|

House

296 BELLA CORTINA DR, POINCIANA, FL, 347...
Community: Solivita
Colonnades 4851 COLONNADES CLUB BLVD, LAKELAND, FL,..., Lakeland, FL 33811
$169,900

2 beds

|

2 baths

|

1,355 sq ft

|

Modular

4851 COLONNADES CLUB BLVD, LAKELAND, FL,...
Community: Colonnades
Covered Bridge 118 HILLCREST ST, LAKE PLACID, FL, 33852, Lake Placid, FL 33852
$299,900

2 beds

|

2 baths

|

1,815 sq ft

|

Villa

118 HILLCREST ST, LAKE PLACID, FL, 33852
Community: Covered Bridge
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
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...
Want to learn more about 55+ communities in Lakeland-Winter Haven Area? 55places can help!
Questions? Call us: (863) 344-5798
Cindy Certified
2021 HARVEST LANDING CIR, LAKELAND, FL, ..., Lakeland, FL 33810
$305,000

4 beds

|

2 baths

|

1,715 sq ft

|

House

2021 HARVEST LANDING CIR, LAKELAND, FL, ...
Cindy Certified
417 HENNEPIN LOOP, LAKE WALES, FL, 33898, Lake Wales, FL 33898
$249,999

3 beds

|

2 baths

|

1,420 sq ft

|

House

417 HENNEPIN LOOP, LAKE WALES, FL, 33898
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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© 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: Oct 31, 2026.
This application does not include information on all of the properties available for sale at this time.

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