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Holiday, FL 55+ active adult communities & homes for sale - Page 6

292 homes 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 - $500Ks
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
5 rating (1 reviews) 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
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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
$200Ks - $400Ks
Timber Greens, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1994 - 2004 | 783 homes
Esplanade at Starkey Ranc...
$400Ks - $900Ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only | Age-targeted | Built 2016 - 2022 | 517 homes
3.3 rating (3 reviews) Royal Stewart Arms
$200Ks - $400Ks
Royal Stewart Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1968 - 1975 | 449 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.
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
Green Dolphin
<$100k - $200Ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
Anchorage
$400Ks
Anchorage, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 homes
Heather Ridge
$100Ks
Heather Ridge, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 homes
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5 rating (1 reviews) Pine Ridge at Palm Harbor
$100Ks
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
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
$100Ks - $1Ms
Edgewater Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 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.
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
Scotsdale Cluster Condomi...
$300Ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 homes
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Questions? Call us: (727) 800-3371
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
<$100k - $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
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 Port Corners
$200Ks - $500Ks
New Port Corners, New Port Richey, FL
New Construction | 55+ age-restricted | Built 2025 - present
Royal Stewart Arms 8 GLENCOE PL 307, DUNEDIN, FL, 34698, Dunedin, FL 34698
$250,000

2 beds

|

1 baths

|

1,100 sq ft

|

Condo

8 GLENCOE PL 307, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Heather Ridge 1450 HEATHER RIDGE BLVD 307, DUNEDIN, FL..., Dunedin, FL 34698
$115,000

2 beds

|

1 baths

|

993 sq ft

|

Condo

1450 HEATHER RIDGE BLVD 307, DUNEDIN, FL...
Community: Heather Ridge
Briar Patch 6516 REMUS DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34653
$180,000

2 beds

|

2 baths

|

964 sq ft

|

Villa

6516 REMUS DR, NEW PORT RICHEY, FL, 3465...
Community: Briar Patch
Highland Lakes on Lake Tarpon 2336 MALCOLM DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$359,900

2 beds

|

2 baths

|

1,288 sq ft

|

House

2336 MALCOLM DR, PALM HARBOR, FL, 34684
Highland Lakes on Lake Tarpon 1109 TARTAN DR C, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$289,000

2 beds

|

2 baths

|

1,280 sq ft

|

Villa

1109 TARTAN DR C, PALM HARBOR, FL, 34684
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Highland Lakes on Lake Tarpon 3499 CEDAR LN, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$310,000

2 beds

|

2 baths

|

1,230 sq ft

|

Villa

3499 CEDAR LN, PALM HARBOR, FL, 34684
Heritage Lake 4635 GAZEBO CT, NEW PORT RICHEY, FL, 346..., New Port Richey, FL 34655
$280,000

2 beds

|

2 baths

|

1,646 sq ft

|

House

4635 GAZEBO CT, NEW PORT RICHEY, FL, 346...
Community: Heritage Lake
Summertree 11501 BLOOMINGTON CT, NEW PORT RICHEY, F..., New Port Richey, FL 34654
$345,500

3 beds

|

2 baths

|

1,863 sq ft

|

House

11501 BLOOMINGTON CT, NEW PORT RICHEY, F...
Community: Summertree
Royal Stewart Arms 7 DUNOON PL APT 203, DUNEDIN, FL, 34698, Dunedin, FL 34698
$324,998

1 beds

|

1 baths

|

957 sq ft

|

Condo

7 DUNOON PL APT 203, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
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.
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
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
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
Highland Lakes on Lake Tarpon 1065 TARTAN DR C, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$260,000

2 beds

|

2 baths

|

1,330 sq ft

|

Condo

1065 TARTAN DR C, PALM HARBOR, FL, 34684
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Patrician Oaks 861 MAPLE CT 104, DUNEDIN, FL, 34698, Dunedin, FL 34698
$83,900

1 beds

|

1 baths

|

817 sq ft

|

Condo

861 MAPLE CT 104, DUNEDIN, FL, 34698
Community: Patrician Oaks
Linkside Village 11141 SANDTRAP DR # 11141, PORT RICHEY, ..., Port Richey, FL 34668
$209,900

2 beds

|

2 baths

|

1,646 sq ft

|

Condo

11141 SANDTRAP DR # 11141, PORT RICHEY, ...
Community: Linkside Village
Timber Oaks 11141 SANDTRAP DR # 11141, PORT RICHEY, ..., Port Richey, FL 34668
$209,900

2 beds

|

2 baths

|

1,646 sq ft

|

Condo

11141 SANDTRAP DR # 11141, PORT RICHEY, ...
Community: Timber Oaks
Beacon Lakes 3847 LIGHTHOUSE WAY # 3847, NEW PORT RIC..., New Port Richey, FL 34652
$179,900

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

3847 LIGHTHOUSE WAY # 3847, NEW PORT RIC...
Community: Beacon Lakes
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.
Village on the Green 2529 OAKLEAF LN 30A, CLEARWATER, FL, 337..., Clearwater, FL 33763
$275,000

2 beds

|

2 baths

|

980 sq ft

|

Villa

2529 OAKLEAF LN 30A, CLEARWATER, FL, 337...
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
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...
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
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
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
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
Highland Lakes on Lake Tarpon 1222 GILLESPIE DR, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$494,900

2 beds

|

2 baths

|

1,674 sq ft

|

House

1222 GILLESPIE DR, PALM HARBOR, FL, 3468...
Key Vista Villas 2542 SANDY HILL CT, HOLIDAY, FL, 34691, Holiday, FL 34691
$385,090

3 beds

|

2 baths

|

1,819 sq ft

|

House

2542 SANDY HILL CT, HOLIDAY, FL, 34691
Community: Key Vista Villas
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.
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
Summertree 11236 MERGANSER WAY, NEW PORT RICHEY, FL..., New Port Richey, FL 34654
$340,000

3 beds

|

2 baths

|

1,558 sq ft

|

House

11236 MERGANSER WAY, NEW PORT RICHEY, FL...
Community: Summertree
Key Vista Villas 2453 PLEASANT HILL LN, HOLIDAY, FL, 3469..., Holiday, FL 34691
$317,000

2 beds

|

2 baths

|

1,555 sq ft

|

House

2453 PLEASANT HILL LN, HOLIDAY, FL, 3469...
Community: Key Vista Villas
Heritage Springs 1249 WINDING WILLOW DR, TRINITY, FL, 346..., Trinity, FL 34655
$399,900

3 beds

|

2 baths

|

1,773 sq ft

|

House

1249 WINDING WILLOW DR, TRINITY, FL, 346...
Community: Heritage Springs
Green Dolphin 1728 GOLFVIEW DR # 1728, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$209,900

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

1728 GOLFVIEW DR # 1728, TARPON SPRINGS,...
Community: Green Dolphin
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Highland Lakes on Lake Tarpon 1609 WHITEBRIDGE DR C, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$149,400

1 beds

|

1 baths

|

964 sq ft

|

Condo

1609 WHITEBRIDGE DR C, PALM HARBOR, FL, ...
Highland Lakes on Lake Tarpon 1632 HEATHER PL, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$439,900

2 beds

|

2 baths

|

1,508 sq ft

|

House

1632 HEATHER PL, PALM HARBOR, FL, 34684
Heritage Lake 4740 CARRINGTON CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$237,000

2 beds

|

2 baths

|

1,340 sq ft

|

Condo

4740 CARRINGTON CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Heather Lake Condominiums 821 PATRICIA AVE 202, DUNEDIN, FL, 34698, Dunedin, FL 34698
$173,900

2 beds

|

1 baths

|

935 sq ft

|

Condo

821 PATRICIA AVE 202, 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.
Village on the Green 2459 BAY BERRY DR, CLEARWATER, FL, 33763, Clearwater, FL 33763
$299,000

2 beds

|

2 baths

|

1,309 sq ft

|

House

2459 BAY BERRY DR, CLEARWATER, FL, 33763
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
Heritage Lake 4872 BOONESBORO CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$159,900

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

4872 BOONESBORO CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Summertree 11636 ASPENWOOD DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$220,000

2 beds

|

2 baths

|

1,226 sq ft

|

House

11636 ASPENWOOD 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
Imperial Pines Condominiums 3076 EASTLAND BLVD 106, CLEARWATER, FL, ..., Clearwater, FL 33761
$210,000

2 beds

|

2 baths

|

1,565 sq ft

|

Condo

3076 EASTLAND BLVD 106, CLEARWATER, FL, ...
Village on the Green 2561 ROYAL PINES CIR # 14H, CLEARWATER, ..., Clearwater, FL 33763
$196,000

2 beds

|

2 baths

|

1,095 sq ft

|

Condo

2561 ROYAL PINES CIR # 14H, CLEARWATER, ...
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