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Holiday, FL 55+ active adult communities & homes for sale - Page 5

281 homes near Holiday

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5 rating (1 reviews) Highland Lakes on Lake Ta...
$100ks - $400ks
Highland Lakes on Lake Ta..., Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1977 - 1989 | 2,454 homes
5 rating (1 reviews) Timber Oaks
<$100k - $200ks
Timber Oaks, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1973 - 1997 | 1,000 homes
Heritage Lake
$100ks - $200ks
Heritage Lake, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1994 | 932 homes
Summertree
$200ks - $300ks
Summertree, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1974 - 2015 | 800 homes
3.3 rating (3 reviews) Royal Stewart Arms
$100ks - $300ks
Royal Stewart Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1968 - 1975 | 449 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heather Lake Condominiums
$100ks
Heather Lake Condominiums, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 homes
3.5 rating (2 reviews) Timber Greens
$200ks - $300ks
Timber Greens, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1994 - 2004 | 783 homes
Green Dolphin
$100ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
4.7 rating (13 reviews) Heritage Springs
$200ks - $500ks
Heritage Springs, Trinity, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,337 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.
Edgewater Arms
$400ks - $600ks
Edgewater Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 homes
5 rating (1 reviews) Pine Ridge at Palm Harbor
$100ks - $200ks
Pine Ridge at Palm Harbor, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1983 - 1983 | 264 homes
Key Vista Villas
$300ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 homes
5 rating (1 reviews) Village on the Green
$100ks - $200ks
Village on the Green, Clearwater, FL
Resale Only | 55+ age-restricted | Built 1978 - 1981 | 448 homes
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Questions? Call us: (727) 800-3371
Pinehurst Village
$100ks
Pinehurst Village, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 homes
Esplanade at Starkey Ranc...
$300ks - $700ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only | Age-targeted | Built 2016 - 2022 | 517 homes
Imperial Pines Condominiu...
$100ks - $200ks
Imperial Pines Condominiu..., Clearwater, FL
Resale Only | 55+ age-restricted | Built 1985 - 1985 | 181 homes
Briar Patch
$100ks
Briar Patch, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 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.
2 rating (1 reviews) Beacon Lakes
$100ks
Beacon Lakes, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 210 homes
Heather Ridge
$100ks - $200ks
Heather Ridge, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 homes
Heather Hills Villas
$100ks
Heather Hills Villas, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1971 - 1976 | 64 homes
Anchorage
$200ks - $300ks
Anchorage, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Country Oaks
$100ks
Country Oaks, Hudson, FL
Resale Only | 55+ age-restricted | Built 1981 - 1986 | 42 homes
Patrician Oaks
$100ks
Patrician Oaks, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 120 homes
Scotsdale Cluster Condomi...
$200ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 homes
New Port Corners
$200ks - $500ks
New Port Corners, New Port Richey, FL
New Construction | 55+ age-restricted | Built 2025 - present
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.
Linkside Village
$200ks
Linkside Village, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 100 homes
Summertree 12154 PUTTER GREEN CT, NEW PORT RICHEY, ..., New Port Richey, FL 34654
$275,500

3 beds

|

2 baths

|

1,522 sq ft

|

Villa

12154 PUTTER GREEN CT, NEW PORT RICHEY, ...
Community: Summertree
Timber Oaks 11130 CARRIAGE HILL DR APT 4, PORT RICHE..., Port Richey, FL 34668
$114,900

2 beds

|

2 baths

|

954 sq ft

|

Condo

11130 CARRIAGE HILL DR APT 4, PORT RICHE...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 2739 SHERBROOKE LN B, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$249,000

2 beds

|

2 baths

|

1,000 sq ft

|

Villa

2739 SHERBROOKE LN B, PALM HARBOR, FL, 3...
Timber Oaks 8360 HIGH POINT CIR 3, PORT RICHEY, FL, ..., Port Richey, FL 34668
$169,000

2 beds

|

2 baths

|

1,372 sq ft

|

Condo

8360 HIGH POINT CIR 3, PORT RICHEY, FL, ...
Community: Timber Oaks
Timber Greens 9742 OAKWOOD HILLS CT, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$475,000

3 beds

|

2 baths

|

1,905 sq ft

|

House

9742 OAKWOOD HILLS CT, NEW PORT RICHEY, ...
Community: Timber Greens
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Highland Lakes on Lake Tarpon 1658 MACDONNELL CT, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$498,000

2 beds

|

2 baths

|

1,875 sq ft

|

House

1658 MACDONNELL CT, PALM HARBOR, FL, 346...
Summertree 11254 MOLLYMAWK CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$349,900

3 beds

|

3 baths

|

2,048 sq ft

|

House

11254 MOLLYMAWK CT, NEW PORT RICHEY, FL,...
Community: Summertree
Royal Stewart Arms 9 HAIG PL 312, DUNEDIN, FL, 34698, Dunedin, FL 34698
$299,900

2 beds

|

2 baths

|

1,181 sq ft

|

Condo

9 HAIG PL 312, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Timber Greens 9713 SWEEPING VIEW DR, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$299,900

2 beds

|

2 baths

|

1,640 sq ft

|

Villa

9713 SWEEPING VIEW DR, NEW PORT RICHEY, ...
Community: Timber Greens
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.
Highland Lakes on Lake Tarpon 2735 SHERBROOKE LN D, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$159,999

1 beds

|

1 baths

|

949 sq ft

|

Condo

2735 SHERBROOKE LN D, PALM HARBOR, FL, 3...
Timber Greens 9338 CLEARMEADOW LN, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$324,990

2 beds

|

2 baths

|

1,855 sq ft

|

Villa

9338 CLEARMEADOW LN, NEW PORT RICHEY, FL...
Community: Timber Greens
Timber Greens 6606 GARDEN PALM CT, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$339,000

3 beds

|

2 baths

|

1,892 sq ft

|

House

6606 GARDEN PALM CT, NEW PORT RICHEY, FL...
Community: Timber Greens
Timber Greens 6525 PINE WALK DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$299,900

2 beds

|

2 baths

|

1,549 sq ft

|

Villa

6525 PINE WALK DR, NEW PORT RICHEY, FL, ...
Community: Timber Greens
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Highland Lakes on Lake Tarpon 1107 QUEEN ANNE DR C, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$200,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1107 QUEEN ANNE DR C, PALM HARBOR, FL, 3...
Green Dolphin 1250 S PINELLAS AVE 803, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$99,500

1 beds

|

1 baths

|

669 sq ft

|

Condo

1250 S PINELLAS AVE 803, TARPON SPRINGS,...
Community: Green Dolphin
Heather Lake Condominiums 940 VIRGINIA ST 105, DUNEDIN, FL, 34698, Dunedin, FL 34698
$117,000

1 beds

|

1 baths

|

770 sq ft

|

Condo

940 VIRGINIA ST 105, DUNEDIN, FL, 34698
Timber Oaks 10705 TONAPA LOOP, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$298,999

3 beds

|

2 baths

|

1,944 sq ft

|

House

10705 TONAPA LOOP, PORT RICHEY, FL, 3466...
Community: Timber Oaks
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.
Pine Ridge at Palm Harbor 1737 PINE RIDGE WAY A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$165,000

2 beds

|

1 baths

|

904 sq ft

|

Condo

1737 PINE RIDGE WAY A, PALM HARBOR, FL, ...
Summertree 12200 PUTTER GREEN CT, NEW PORT RICHEY, ..., New Port Richey, FL 34654
$290,000

3 beds

|

2 baths

|

1,719 sq ft

|

Villa

12200 PUTTER GREEN CT, NEW PORT RICHEY, ...
Community: Summertree
Royal Stewart Arms 9 HAIG PL 704, DUNEDIN, FL, 34698, Dunedin, FL 34698
$325,000

2 beds

|

2 baths

|

975 sq ft

|

Condo

9 HAIG PL 704, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Highland Lakes on Lake Tarpon 1350 GLENGARRY DR, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$474,900

2 beds

|

2 baths

|

1,694 sq ft

|

House

1350 GLENGARRY DR, PALM HARBOR, FL, 3468...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heather Lake Condominiums 841 PATRICIA AVE 306, DUNEDIN, FL, 34698, Dunedin, FL 34698
$145,000

2 beds

|

2 baths

|

934 sq ft

|

Condo

841 PATRICIA AVE 306, DUNEDIN, FL, 34698
Highland Lakes on Lake Tarpon 3251 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$339,900

2 beds

|

2 baths

|

1,332 sq ft

|

Villa

3251 MCMATH DR, PALM HARBOR, FL, 34684
Timber Oaks 8350 HIGH POINT CIR 3, PORT RICHEY, FL, ..., Port Richey, FL 34668
$185,000

2 beds

|

2 baths

|

1,372 sq ft

|

Condo

8350 HIGH POINT CIR 3, PORT RICHEY, FL, ...
Community: Timber Oaks
Briar Patch 6531 REMUS DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34653
$205,000

3 beds

|

2 baths

|

1,359 sq ft

|

Townhouse

6531 REMUS DR, NEW PORT RICHEY, FL, 3465...
Community: Briar Patch
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.
Royal Stewart Arms 5 GATESHEAD DR 107, DUNEDIN, FL, 34698, Dunedin, FL 34698
$394,900

2 beds

|

2 baths

|

1,175 sq ft

|

Condo

5 GATESHEAD DR 107, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Highland Lakes on Lake Tarpon 2211 LARK CIR D, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$190,000

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

2211 LARK CIR D, PALM HARBOR, FL, 34684
Heritage Lake 4745 VICKSBURG CT, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$230,000

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

4745 VICKSBURG CT, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
Highland Lakes on Lake Tarpon 899 CLELAND CT A, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$265,000

2 beds

|

2 baths

|

1,230 sq ft

|

Villa

899 CLELAND CT A, PALM HARBOR, FL, 34684
Timber Oaks 11508 ORLEANS LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$191,000

2 beds

|

2 baths

|

1,395 sq ft

|

Condo

11508 ORLEANS LN, PORT RICHEY, FL, 34668
Community: Timber Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heritage Lake 4814 PRINCE GEORGE CIR, NEW PORT RICHEY,..., New Port Richey, FL 34655
$269,900

2 beds

|

2 baths

|

2,001 sq ft

|

House

4814 PRINCE GEORGE CIR, NEW PORT RICHEY,...
Community: Heritage Lake
Heritage Lake 4638 SHEFFIELD DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$294,900

2 beds

|

2 baths

|

1,261 sq ft

|

Condo

4638 SHEFFIELD DR, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
Timber Oaks 8025 SAN FERNANDO DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$299,900

3 beds

|

2 baths

|

1,530 sq ft

|

House

8025 SAN FERNANDO DR, PORT RICHEY, FL, 3...
Community: Timber Oaks
Heather Hills Villas 1055 LOCH HAVEN DR, DUNEDIN, FL, 34698, Dunedin, FL 34698
$224,900

2 beds

|

2 baths

|

999 sq ft

|

Villa

1055 LOCH HAVEN DR, DUNEDIN, FL, 34698
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.
Imperial Pines Condominiums 3062 EASTLAND BLVD 406, CLEARWATER, FL, ..., Clearwater, FL 33761
$157,500

1 beds

|

1 baths

|

920 sq ft

|

Condo

3062 EASTLAND BLVD 406, CLEARWATER, FL, ...
Heritage Lake 9404 ROCKBRIDGE CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$189,500

2 beds

|

2 baths

|

1,227 sq ft

|

Condo

9404 ROCKBRIDGE CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
Heather Lake Condominiums 952 VIRGINIA ST 105, DUNEDIN, FL, 34698, Dunedin, FL 34698
$230,000

2 beds

|

2 baths

|

965 sq ft

|

Condo

952 VIRGINIA ST 105, DUNEDIN, FL, 34698
Timber Oaks 11110 CARRIAGE HILL DR 5, PORT RICHEY, F..., Port Richey, FL 34668
$99,999

2 beds

|

1 baths

|

882 sq ft

|

Condo

11110 CARRIAGE HILL DR 5, PORT RICHEY, F...
Community: Timber Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Key Vista Villas 2453 PLEASANT HILL LN, HOLIDAY, FL, 3469..., Holiday, FL 34691
$300,000

2 beds

|

2 baths

|

1,555 sq ft

|

House

2453 PLEASANT HILL LN, HOLIDAY, FL, 3469...
Community: Key Vista Villas
Highland Lakes on Lake Tarpon 142 STAFFORD CIR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$357,900

2 beds

|

2 baths

|

1,294 sq ft

|

House

142 STAFFORD CIR, PALM HARBOR, FL, 34684
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