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

26 communities near Holiday

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Key Vista Villas
$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 - $400Ks
Heritage Springs, Trinity, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,337 homes
Timber Oaks
<$100k - $300Ks
Timber Oaks, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1973 - 1997 | 1,000 homes
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
Summertree
$100Ks - $300Ks
Summertree, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1974 - 2015 | 800 homes
3.5 rating (2 reviews) Timber Greens
$300Ks - $400Ks
Timber Greens, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1994 - 2004 | 783 homes
Esplanade at Starkey Ranc...
$400Ks - $1Ms
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.
Green Dolphin
$100Ks - $200Ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
Anchorage
$300Ks - $400Ks
Anchorage, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 homes
Heather Ridge
$100Ks - $200Ks
Heather Ridge, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 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
Pinehurst Village
$100Ks - $200Ks
Pinehurst Village, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 homes
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Questions? Call us: (727) 800-3371
2 rating (1 reviews) Beacon Lakes
$100Ks
Beacon Lakes, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 210 homes
Edgewater Arms
$400Ks - $1Ms
Edgewater Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 homes
Heather Lake Condominiums
$100Ks - $200Ks
Heather Lake Condominiums, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 homes
Briar Patch
$100Ks - $200Ks
Briar Patch, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 homes
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.
Scotsdale Cluster Condomi...
$300Ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 homes
Patrician Oaks
<$100k
Patrician Oaks, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 120 homes
Linkside Village
$100Ks - $200Ks
Linkside Village, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 100 homes
Heather Hills Villas
$100Ks - $200Ks
Heather Hills Villas, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1971 - 1976 | 64 homes
Country Oaks
$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
New Port Corners
$200Ks - $500Ks
New Port Corners, New Port Richey, FL
New Construction | 55+ age-restricted | Built 2025 - present
Briar Patch 6428 THICKET TRL, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34653
$220,000

2 beds

|

2 baths

|

964 sq ft

|

Villa

6428 THICKET TRL, NEW PORT RICHEY, FL, 3...
Community: Briar Patch
Timber Greens 9626 WOODHOLLOW CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$379,900

2 beds

|

2 baths

|

1,679 sq ft

|

Villa

9626 WOODHOLLOW CT, NEW PORT RICHEY, FL,...
Community: Timber Greens
Heritage Lake 4719 CAVENDISH DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$298,900

2 beds

|

2 baths

|

1,646 sq ft

|

House

4719 CAVENDISH DR, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
Timber Oaks 8131 BRADDOCK CIR 1, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$132,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

8131 BRADDOCK CIR 1, PORT RICHEY, FL, 34...
Community: Timber Oaks
Patrician Oaks 820 VIRGINIA ST APT 207, DUNEDIN, FL, 34..., Dunedin, FL 34698
$140,000

2 beds

|

1 baths

|

1,004 sq ft

|

Condo

820 VIRGINIA ST APT 207, DUNEDIN, FL, 34...
Community: Patrician Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Pinehurst Village 1701 PINEHURST RD APT 13C, DUNEDIN, FL, ..., Dunedin, FL 34698
$153,900

1 beds

|

1 baths

|

645 sq ft

|

Condo

1701 PINEHURST RD APT 13C, DUNEDIN, FL, ...
Community: Pinehurst Village
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
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
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 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
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 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
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
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
Highland Lakes on Lake Tarpon 2722 SHERBROOKE LN D, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$170,000

1 beds

|

2 baths

|

814 sq ft

|

Condo

2722 SHERBROOKE LN D, PALM HARBOR, FL, 3...
Imperial Pines Condominiums 3062 EASTLAND BLVD UNIT 308, CLEARWATER,..., Clearwater, FL 33761
$270,000

2 beds

|

2 baths

|

1,565 sq ft

|

Condo

3062 EASTLAND BLVD UNIT 308, CLEARWATER,...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Beacon Lakes 4028 DAVIT DR # 4028, NEW PORT RICHEY, F..., New Port Richey, FL 34652
$185,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

4028 DAVIT DR # 4028, NEW PORT RICHEY, F...
Community: Beacon Lakes
Heather Lake Condominiums 940 VIRGINIA ST 303, DUNEDIN, FL, 34698, Dunedin, FL 34698
$225,000

2 beds

|

2 baths

|

927 sq ft

|

Condo

940 VIRGINIA ST 303, DUNEDIN, FL, 34698
Heritage Lake 9843 SAINT JOSEPH CT, NEW PORT RICHEY, F..., New Port Richey, FL 34655
$325,000

2 beds

|

2 baths

|

1,678 sq ft

|

House

9843 SAINT JOSEPH CT, NEW PORT RICHEY, F...
Community: Heritage Lake
New Esplanade at Starkey Ranch 2930 FRANCOA DR, ODESSA, FL, 33556, Odessa, FL 33556
$450,000

2 beds

|

2 baths

|

1,689 sq ft

|

House

2930 FRANCOA DR, ODESSA, FL, 33556
Heritage Springs 1251 RAMBLING VINE CT, TRINITY, FL, 3465..., Trinity, FL 34655
$450,000

3 beds

|

2 baths

|

1,814 sq ft

|

House

1251 RAMBLING VINE CT, TRINITY, FL, 3465...
Community: Heritage Springs
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 Heather Lake Condominiums 952 VIRGINIA ST 105, DUNEDIN, FL, 34698, Dunedin, FL 34698
$245,000

2 beds

|

2 baths

|

965 sq ft

|

Condo

952 VIRGINIA ST 105, DUNEDIN, FL, 34698
New Highland Lakes on Lake Tarpon 142 STAFFORD CIR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$375,000

2 beds

|

2 baths

|

1,294 sq ft

|

House

142 STAFFORD CIR, PALM HARBOR, FL, 34684
Heritage Lake 9531 DANVILLE CT -, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$219,900

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

9531 DANVILLE CT -, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Highland Lakes on Lake Tarpon 3116 BRUNSWICK CIR, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$499,900

3 beds

|

2 baths

|

1,699 sq ft

|

House

3116 BRUNSWICK CIR, PALM HARBOR, FL, 346...
Royal Stewart Arms 9 FORBES PL 512, DUNEDIN, FL, 34698, Dunedin, FL 34698
$365,000

2 beds

|

2 baths

|

1,181 sq ft

|

Condo

9 FORBES PL 512, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heritage Springs 1046 ALMONDWOOD DR, TRINITY, FL, 34655, Trinity, FL 34655
$389,900

2 beds

|

2 baths

|

1,546 sq ft

|

Villa

1046 ALMONDWOOD DR, TRINITY, FL, 34655
Community: Heritage Springs
Highland Lakes on Lake Tarpon 3390 STONEHAVEN CT A, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$319,900

2 beds

|

2 baths

|

1,337 sq ft

|

Villa

3390 STONEHAVEN CT A, PALM HARBOR, FL, 3...
New Highland Lakes on Lake Tarpon 2955 BRIAR CLIFF DR, PALM HARBOR, FL, 34..., Palm Harbor, FL 34684
$333,000

2 beds

|

2 baths

|

1,269 sq ft

|

House

2955 BRIAR CLIFF DR, PALM HARBOR, FL, 34...
Timber Oaks 11241 VERSAILLES LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$166,900

2 beds

|

2 baths

|

1,037 sq ft

|

Condo

11241 VERSAILLES LN, PORT RICHEY, FL, 34...
Community: Timber Oaks
New Timber Oaks 8034 MERRIMAC DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$260,000

2 beds

|

2 baths

|

1,260 sq ft

|

House

8034 MERRIMAC DR, PORT RICHEY, FL, 34668
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.
Highland Lakes on Lake Tarpon 1637 CALEDONIA DR, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$368,000

2 beds

|

2 baths

|

1,492 sq ft

|

House

1637 CALEDONIA DR, PALM HARBOR, FL, 3468...
New Timber Oaks 11110 CARRIAGE HILL DR APT 5, PORT RICHE..., Port Richey, FL 34668
$104,000

2 beds

|

1 baths

|

882 sq ft

|

Condo

11110 CARRIAGE HILL DR APT 5, PORT RICHE...
Community: Timber Oaks
Key Vista Villas 2735 PLANTAIN DR, HOLIDAY, FL, 34691, Holiday, FL 34691
$319,900

2 beds

|

2 baths

|

1,555 sq ft

|

House

2735 PLANTAIN DR, HOLIDAY, FL, 34691
Community: Key Vista Villas
Edgewater Arms 632 EDGEWATER DR 433, DUNEDIN, FL, 34698, Dunedin, FL 34698
$449,000

2 beds

|

2 baths

|

1,425 sq ft

|

Condo

632 EDGEWATER DR 433, DUNEDIN, FL, 34698
Community: Edgewater Arms
Highland Lakes on Lake Tarpon 2836 HIGHLANDS BLVD A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$189,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

2836 HIGHLANDS BLVD A, PALM HARBOR, FL, ...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Pinehurst Village 1701 PINEHURST RD 22B, DUNEDIN, FL, 3469..., Dunedin, FL 34698
$187,500

2 beds

|

1 baths

|

875 sq ft

|

Villa

1701 PINEHURST RD 22B, DUNEDIN, FL, 3469...
Community: Pinehurst Village
Highland Lakes on Lake Tarpon 1614 BERWICK CT D, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$185,000

1 beds

|

1 baths

|

814 sq ft

|

Villa

1614 BERWICK CT D, PALM HARBOR, FL, 3468...
Summertree 11723 FOXWORTH LN, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34654
$264,900

2 beds

|

2 baths

|

1,096 sq ft

|

Villa

11723 FOXWORTH LN, NEW PORT RICHEY, FL, ...
Community: Summertree
Heritage Lake 9643 NOBLE CT, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34655
$269,900

2 beds

|

2 baths

|

1,230 sq ft

|

House

9643 NOBLE CT, NEW PORT RICHEY, FL, 3465...
Community: Heritage Lake
Timber Oaks 8130 SAN FELIPE CT, PORT RICHEY, FL, 346..., Port Richey, FL 34668
$334,900

3 beds

|

2 baths

|

1,670 sq ft

|

House

8130 SAN FELIPE CT, PORT RICHEY, FL, 346...
Community: Timber Oaks
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26 communities near Holiday
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