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

306 homes near Holiday

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No reviews yet Key Vista Villas
$300Ks - $300Ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 homes
5 rating (1 reviews) Highland Lakes on Lake Ta...
<$100k - $400Ks
Highland Lakes on Lake Ta..., Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1977 - 1989 | 2,454 homes
4.7 rating (13 reviews) Heritage Springs
$300Ks - $500Ks
Heritage Springs, Trinity, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,337 homes
No reviews yet Timber Oaks
<$100k - $300Ks
Timber Oaks, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1973 - 1997 | 1,000 homes
No reviews yet Heritage Lake
$100Ks - $300Ks
Heritage Lake, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1994 | 932 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
No reviews yet Summertree
$200Ks - $300Ks
Summertree, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1974 - 2015 | 800 homes
3.5 rating (2 reviews) Timber Greens
$200Ks - $400Ks
Timber Greens, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1994 - 2004 | 783 homes
No reviews yet Esplanade at Starkey Ranc...
$400Ks - $800Ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only | Age-targeted | Built 2016 - 2022 | 517 homes
3.3 rating (3 reviews) Royal Stewart Arms
$200Ks - $300Ks
Royal Stewart Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1968 - 1975 | 449 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
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.
No reviews yet Green Dolphin
$100Ks - $200Ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
No reviews yet Anchorage
$200Ks - $400Ks
Anchorage, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 homes
No reviews yet Heather Ridge
$100Ks - $100Ks
Heather Ridge, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 homes
5 rating (1 reviews) Pine Ridge at Palm Harbor
$100Ks - $300Ks
Pine Ridge at Palm Harbor, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1983 - 1983 | 264 homes
No reviews yet Pinehurst Village
$100Ks - $200Ks
Pinehurst Village, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
2 rating (1 reviews) Beacon Lakes
$100Ks - $100Ks
Beacon Lakes, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 210 homes
No reviews yet Edgewater Arms
$400Ks - $400Ks
Edgewater Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 homes
No reviews yet Heather Lake Condominiums
<$100k - $200Ks
Heather Lake Condominiums, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 homes
No reviews yet Briar Patch
$100Ks - $200Ks
Briar Patch, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 homes
No reviews yet Imperial Pines Condominiu...
$100Ks - $200Ks
Imperial Pines Condominiu..., Clearwater, FL
Resale Only | 55+ age-restricted | Built 1985 - 1985 | 181 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.
No reviews yet Scotsdale Cluster Condomi...
$300Ks - $300Ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 homes
No reviews yet Patrician Oaks
<$100k - $100Ks
Patrician Oaks, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 120 homes
No reviews yet Linkside Village
$100Ks - $200Ks
Linkside Village, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 100 homes
No reviews yet Heather Hills Villas
$100Ks - $200Ks
Heather Hills Villas, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1971 - 1976 | 64 homes
No reviews yet Country Oaks
$100Ks - $100Ks
Country Oaks, Hudson, FL
Resale Only | 55+ age-restricted | Built 1981 - 1986 | 42 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
No reviews yet New Port Corners
$200Ks - $500Ks
New Port Corners, New Port Richey, FL
New Construction | 55+ age-restricted | Built 2025 - present
Highland Lakes on Lake Tarpon 2735 SHERBROOKE LN D, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$175,000

1 beds

|

1 baths

|

949 sq ft

|

Villa

2735 SHERBROOKE LN D, PALM HARBOR, FL, 3...
Heather Lake Condominiums 946 VIRGINIA ST 304, DUNEDIN, FL, 34698, Dunedin, FL 34698
$99,000

1 beds

|

1 baths

|

845 sq ft

|

Condo

946 VIRGINIA ST 304, DUNEDIN, FL, 34698
Heritage Lake 9531 DANVILLE CT NA, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$219,900

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

9531 DANVILLE CT NA, NEW PORT RICHEY, FL...
Community: Heritage Lake
Heritage Lake 4707 WALLINGFORD CT # 4707, NEW PORT RIC..., New Port Richey, FL 34655
$164,900

2 beds

|

2 baths

|

1,401 sq ft

|

Condo

4707 WALLINGFORD CT # 4707, NEW PORT RIC...
Community: Heritage Lake
Summertree 11719 ROSE TREE DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$264,900

3 beds

|

2 baths

|

1,454 sq ft

|

House

11719 ROSE TREE DR, NEW PORT RICHEY, FL,...
Community: Summertree
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 11132 PEMBRIDGE CT APT 3, PORT RICHEY, F..., Port Richey, FL 34668
$89,995

1 beds

|

1 baths

|

714 sq ft

|

Condo

11132 PEMBRIDGE CT APT 3, PORT RICHEY, F...
Community: Timber Oaks
Timber Oaks 8101 CASUARINA DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$229,000

2 beds

|

2 baths

|

1,107 sq ft

|

House

8101 CASUARINA DR, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Patrician Oaks 870 VIRGINIA ST APT 113, DUNEDIN, FL, 34..., Dunedin, FL 34698
$150,000

2 beds

|

1 baths

|

973 sq ft

|

Condo

870 VIRGINIA ST APT 113, DUNEDIN, FL, 34...
Community: Patrician Oaks
Patrician Oaks 845 MAPLE CT APT 103, DUNEDIN, FL, 34698, Dunedin, FL 34698
$179,000

2 beds

|

1 baths

|

1,004 sq ft

|

Condo

845 MAPLE CT APT 103, DUNEDIN, FL, 34698
Community: Patrician Oaks
Green Dolphin 1250 S PINELLAS AVE APT 405, TARPON SPRI..., Tarpon Springs, FL 34689
$124,900

1 beds

|

1 baths

|

669 sq ft

|

Condo

1250 S PINELLAS AVE APT 405, TARPON SPRI...
Community: Green Dolphin
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.
Heather Hills Villas 858 CAMBRIDGE CT # 858, DUNEDIN, FL, 346..., Dunedin, FL 34698
$210,000

2 beds

|

2 baths

|

990 sq ft

|

Condo

858 CAMBRIDGE CT # 858, DUNEDIN, FL, 346...
Heather Hills Villas 857 CAMBRIDGE CT, DUNEDIN, FL, 34698, Dunedin, FL 34698
$175,000

2 beds

|

1 baths

|

863 sq ft

|

Condo

857 CAMBRIDGE CT, DUNEDIN, FL, 34698
Highland Lakes on Lake Tarpon 2866 THISTLE CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$468,900

2 beds

|

2 baths

|

1,578 sq ft

|

House

2866 THISTLE CT, PALM HARBOR, FL, 34684
Heritage Lake 4614 SANDPOINTE DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$349,000

2 beds

|

2 baths

|

1,738 sq ft

|

House

4614 SANDPOINTE DR, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Pinehurst Village 1701 PINEHURST RD 33E, DUNEDIN, FL, 3469..., Dunedin, FL 34698
$269,900

2 beds

|

2 baths

|

875 sq ft

|

Condo

1701 PINEHURST RD 33E, DUNEDIN, FL, 3469...
Community: Pinehurst Village
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heritage Lake 9444 ROCKBRIDGE CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$214,900

2 beds

|

2 baths

|

1,335 sq ft

|

Condo

9444 ROCKBRIDGE CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
Highland Lakes on Lake Tarpon 3283 HILARY CIR 2C, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$215,000

2 beds

|

2 baths

|

1,000 sq ft

|

Villa

3283 HILARY CIR 2C, PALM HARBOR, FL, 346...
Timber Oaks 11516 VERSAILLES LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$189,000

2 beds

|

2 baths

|

1,166 sq ft

|

Condo

11516 VERSAILLES LN, PORT RICHEY, FL, 34...
Community: Timber Oaks
Pine Ridge at Palm Harbor 2699 PINE RIDGE WAY H2, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$199,900

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

2699 PINE RIDGE WAY H2, PALM HARBOR, FL,...
Anchorage 801 LEEWARD WAY, PALM HARBOR, FL, 34685, Palm Harbor, FL 34685
$349,900

3 beds

|

2 baths

|

1,286 sq ft

|

House

801 LEEWARD WAY, PALM HARBOR, FL, 34685
Community: Anchorage
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.
Heritage Springs 1142 WOLFORD DR, TRINITY, FL, 34655, Trinity, FL 34655
$389,000

2 beds

|

2 baths

|

1,465 sq ft

|

Villa

1142 WOLFORD DR, TRINITY, FL, 34655
Community: Heritage Springs
Anchorage 2212 PORTSIDE PSGE, PALM HARBOR, FL, 346..., Palm Harbor, FL 34685
$289,000

2 beds

|

2 baths

|

1,575 sq ft

|

House

2212 PORTSIDE PSGE, PALM HARBOR, FL, 346...
Community: Anchorage
Green Dolphin 1250 S PINELLAS AVE APT 214, TARPON SPRI..., Tarpon Springs, FL 34689
$180,000

2 beds

|

2 baths

|

871 sq ft

|

Condo

1250 S PINELLAS AVE APT 214, TARPON SPRI...
Community: Green Dolphin
Key Vista Villas 2926 WALNUT GROVE CT, HOLIDAY, FL, 34691, Holiday, FL 34691
$349,500

3 beds

|

2 baths

|

1,341 sq ft

|

House

2926 WALNUT GROVE CT, HOLIDAY, FL, 34691
Community: Key Vista Villas
Highland Lakes on Lake Tarpon 2770 KEATS TER C, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$218,000

2 beds

|

2 baths

|

1,050 sq ft

|

Villa

2770 KEATS TER C, PALM HARBOR, FL, 34684
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 8619 GOLD PINE DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$242,200

2 beds

|

2 baths

|

1,658 sq ft

|

House

8619 GOLD PINE DR, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Timber Oaks 11241 DOLLAR LAKE DR 5, PORT RICHEY, FL,..., Port Richey, FL 34668
$155,000

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

11241 DOLLAR LAKE DR 5, PORT RICHEY, FL,...
Community: Timber Oaks
Timber Oaks 8420 WINDING WOOD DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$240,000

2 beds

|

2 baths

|

1,274 sq ft

|

House

8420 WINDING WOOD DR, PORT RICHEY, FL, 3...
Community: Timber Oaks
Briar Patch 6514 THICKET TRL, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34653
$199,000

2 beds

|

2 baths

|

964 sq ft

|

House

6514 THICKET TRL, NEW PORT RICHEY, FL, 3...
Community: Briar Patch
Village on the Green 2546 OAKLEAF LN 35D, CLEARWATER, FL, 337..., Clearwater, FL 33763
$250,000

2 beds

|

2 baths

|

980 sq ft

|

Villa

2546 OAKLEAF LN 35D, CLEARWATER, FL, 337...
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 9 HAIG PL 510, DUNEDIN, FL, 34698, Dunedin, FL 34698
$349,000

2 beds

|

2 baths

|

975 sq ft

|

Condo

9 HAIG PL 510, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Timber Oaks 11231 DOLLAR LAKE DR APT 6, PORT RICHEY,..., Port Richey, FL 34668
$169,900

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

11231 DOLLAR LAKE DR APT 6, PORT RICHEY,...
Community: Timber Oaks
Timber Oaks 8140 SAN FELIPE CT, PORT RICHEY, FL, 346..., Port Richey, FL 34668
$269,900

2 beds

|

2 baths

|

1,510 sq ft

|

House

8140 SAN FELIPE CT, PORT RICHEY, FL, 346...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 946 MADRID DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$345,000

2 beds

|

2 baths

|

980 sq ft

|

Villa

946 MADRID DR, PALM HARBOR, FL, 34684
Edgewater Arms 632 EDGEWATER DR 832, DUNEDIN, FL, 34698, Dunedin, FL 34698
$459,000

2 beds

|

2 baths

|

1,620 sq ft

|

Condo

632 EDGEWATER DR 832, DUNEDIN, FL, 34698
Community: Edgewater Arms
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Briar Patch 6421 REMUS DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34653
$205,000

2 beds

|

2 baths

|

964 sq ft

|

Villa

6421 REMUS DR, NEW PORT RICHEY, FL, 3465...
Community: Briar Patch
Pine Ridge at Palm Harbor 1725 PINE RIDGE WAY E APT E C, PALM HARB..., Palm Harbor, FL 34684
$300,000

2 beds

|

2 baths

|

1,350 sq ft

|

Villa

1725 PINE RIDGE WAY E APT E C, PALM HARB...
Timber Oaks 11311 DOLLAR LAKE DR APT 6, PORT RICHEY,..., Port Richey, FL 34668
$187,000

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

11311 DOLLAR LAKE DR APT 6, PORT RICHEY,...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 3116 HIGHLANDS BLVD # 3116, PALM HARBOR,..., Palm Harbor, FL 34684
$140,000

1 beds

|

1 baths

|

636 sq ft

|

Condo

3116 HIGHLANDS BLVD # 3116, PALM HARBOR,...
Anchorage 918 WINDWARD WAY, PALM HARBOR, FL, 34685, Palm Harbor, FL 34685
$364,900

3 beds

|

3 baths

|

1,960 sq ft

|

House

918 WINDWARD WAY, PALM HARBOR, FL, 34685
Community: Anchorage
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306 homes near Holiday
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