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Holiday, FL 55+ active adult communities & homes for sale - Page 3

272 homes near Holiday

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5 rating (1 reviews) Timber Oaks
<$100k - $200ks
Timber Oaks, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1973 - 1997 | 1,000 homes
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
4.7 rating (13 reviews) Heritage Springs
$200ks - $500ks
Heritage Springs, Trinity, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,337 homes
Heather Lake Condominiums
$100ks
Heather Lake Condominiums, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 homes
Summertree
$200ks - $300ks
Summertree, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1974 - 2015 | 800 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heritage Lake
$100ks - $200ks
Heritage Lake, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1994 | 932 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
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
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
Edgewater Arms
$400ks - $600ks
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.
Briar Patch
$100ks
Briar Patch, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 homes
Esplanade at Starkey Ranc...
$300ks - $700ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only | Age-targeted | Built 2016 - 2022 | 517 homes
Key Vista Villas
$300ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 homes
2 rating (1 reviews) Beacon Lakes
$100ks
Beacon Lakes, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 210 homes
Imperial Pines Condominiu...
$100ks - $200ks
Imperial Pines Condominiu..., Clearwater, FL
Resale Only | 55+ age-restricted | Built 1985 - 1985 | 181 homes
Green Dolphin
$100ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Patrician Oaks
$100ks
Patrician Oaks, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 120 homes
Anchorage
$200ks - $300ks
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
Pinehurst Village
$100ks
Pinehurst Village, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 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
Scotsdale Cluster Condomi...
$200ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 homes
Heather Hills Villas
$100ks
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
Linkside Village
$200ks
Linkside Village, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 100 homes
Soleta at Starkey Ranch
$500ks - $600ks
Soleta at Starkey Ranch, Odessa, FL
New Construction | Age-targeted | Built 2023 - present | 139 homes
New Port Corners
$200ks - $500ks
New Port Corners, New Port Richey, FL
New Construction | 55+ age-restricted | Built 2025 - present
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Highland Lakes on Lake Tarpon 1060 DUNROBIN DR A, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$249,900

2 beds

|

2 baths

|

1,230 sq ft

|

Villa

1060 DUNROBIN DR A, PALM HARBOR, FL, 346...
Green Dolphin 1250 S PINELLAS AVE 205, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$129,500

1 beds

|

1 baths

|

669 sq ft

|

Condo

1250 S PINELLAS AVE 205, TARPON SPRINGS,...
Community: Green Dolphin
Village on the Green 2210 SEQUOIA DR, CLEARWATER, FL, 33763, Clearwater, FL 33763
$329,000

2 beds

|

2 baths

|

1,309 sq ft

|

House

2210 SEQUOIA DR, CLEARWATER, FL, 33763
Royal Stewart Arms 2 CAUSEWAY BLVD 208, DUNEDIN, FL, 34698, Dunedin, FL 34698
$360,000

2 beds

|

2 baths

|

1,123 sq ft

|

Condo

2 CAUSEWAY BLVD 208, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Pine Ridge at Palm Harbor 2688 PINE RIDGE WAY A2, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$184,900

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

2688 PINE RIDGE WAY A2, PALM HARBOR, FL,...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Esplanade at Starkey Ranch 11257 CALLISIA DR, ODESSA, FL, 33556, Odessa, FL 33556
$525,000

3 beds

|

2 baths

|

1,931 sq ft

|

House

11257 CALLISIA DR, ODESSA, FL, 33556
Heritage Lake 9427 CAPE CHARLES AVE, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$200,000

2 beds

|

2 baths

|

1,016 sq ft

|

House

9427 CAPE CHARLES AVE, NEW PORT RICHEY, ...
Community: Heritage Lake
Heather Lake Condominiums 952 VIRGINIA ST 202, DUNEDIN, FL, 34698, Dunedin, FL 34698
$194,999

2 beds

|

2 baths

|

965 sq ft

|

Condo

952 VIRGINIA ST 202, DUNEDIN, FL, 34698
Timber Oaks 8119 SAN BERNARDINO DR, PORT RICHEY, FL,..., Port Richey, FL 34668
$276,000

3 beds

|

2 baths

|

1,784 sq ft

|

House

8119 SAN BERNARDINO DR, PORT RICHEY, FL,...
Community: Timber Oaks
Esplanade at Starkey Ranch 11257 EGERIA DR, ODESSA, FL, 33556, Odessa, FL 33556
$749,900

3 beds

|

4 baths

|

2,740 sq ft

|

House

11257 EGERIA DR, ODESSA, FL, 33556
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.
Anchorage 835 ANCHORAGE LN, PALM HARBOR, FL, 34685, Palm Harbor, FL 34685
$459,900

3 beds

|

2 baths

|

1,822 sq ft

|

House

835 ANCHORAGE LN, PALM HARBOR, FL, 34685
Community: Anchorage
Heather Ridge 1370 HEATHER RIDGE BLVD 204, DUNEDIN, FL..., Dunedin, FL 34698
$114,900

2 beds

|

1 baths

|

990 sq ft

|

Condo

1370 HEATHER RIDGE BLVD 204, DUNEDIN, FL...
Community: Heather Ridge
Anchorage 1010 MAINSAIL WAY, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34685
$440,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

1010 MAINSAIL WAY, PALM HARBOR, FL, 3468...
Community: Anchorage
Heritage Springs 1933 ARBOR KNOLL LOOP, TRINITY, FL, 3465..., Trinity, FL 34655
$373,000

2 beds

|

2 baths

|

1,900 sq ft

|

Villa

1933 ARBOR KNOLL LOOP, TRINITY, FL, 3465...
Community: Heritage Springs
Summertree 11303 CLEAR OAK CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34654
$350,000

3 beds

|

2 baths

|

1,854 sq ft

|

House

11303 CLEAR OAK CIR, NEW PORT RICHEY, FL...
Community: Summertree
Timber Oaks 8510 WINDING WOOD DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$263,000

2 beds

|

2 baths

|

1,461 sq ft

|

House

8510 WINDING WOOD DR, PORT RICHEY, FL, 3...
Community: Timber Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Imperial Pines Condominiums 3078 EASTLAND BLVD 309, CLEARWATER, FL, ..., Clearwater, FL 33761
$249,900

2 beds

|

2 baths

|

1,390 sq ft

|

Condo

3078 EASTLAND BLVD 309, CLEARWATER, FL, ...
Timber Greens 6447 PINE WALK DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$320,000

2 beds

|

2 baths

|

1,352 sq ft

|

Villa

6447 PINE WALK DR, NEW PORT RICHEY, FL, ...
Community: Timber Greens
Summertree 11213 KISKADEE CIR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$339,000

3 beds

|

2 baths

|

1,834 sq ft

|

House

11213 KISKADEE CIR, NEW PORT RICHEY, FL,...
Community: Summertree
Key Vista Villas 2529 SANDY HILL CT, HOLIDAY, FL, 34691, Holiday, FL 34691
$379,000

2 beds

|

2 baths

|

1,555 sq ft

|

House

2529 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.
Heritage Springs 1046 ALMONDWOOD DR, TRINITY, FL, 34655, Trinity, FL 34655
$359,900

2 beds

|

2 baths

|

1,546 sq ft

|

Villa

1046 ALMONDWOOD DR, TRINITY, FL, 34655
Community: Heritage Springs
Key Vista Villas 2945 WOOD POINTE DR, HOLIDAY, FL, 34691, Holiday, FL 34691
$345,000

2 beds

|

2 baths

|

1,341 sq ft

|

House

2945 WOOD POINTE DR, HOLIDAY, FL, 34691
Community: Key Vista Villas
Royal Stewart Arms 9 FORBES PL 707, DUNEDIN, FL, 34698, Dunedin, FL 34698
$259,000

1 beds

|

1 baths

|

802 sq ft

|

Condo

9 FORBES PL 707, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Pine Ridge at Palm Harbor 2688 PINE RIDGE WAY D2, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$183,900

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

2688 PINE RIDGE WAY D2, PALM HARBOR, FL,...
Highland Lakes on Lake Tarpon 1735 ABERDEEN CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$465,000

3 beds

|

2 baths

|

1,556 sq ft

|

House

1735 ABERDEEN CT, PALM HARBOR, FL, 34684
Heather Ridge 1450 HEATHER RIDGE BLVD 307, DUNEDIN, FL..., Dunedin, FL 34698
$109,000

2 beds

|

1 baths

|

993 sq ft

|

Condo

1450 HEATHER RIDGE BLVD 307, DUNEDIN, FL...
Community: Heather Ridge
Heritage Lake 4808 VESPER CT 34, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$176,000

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

4808 VESPER CT 34, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 11340 DOLLAR LAKE DR 2, PORT RICHEY, FL,..., Port Richey, FL 34668
$144,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

11340 DOLLAR LAKE DR 2, PORT RICHEY, FL,...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 999 GILLESPIE DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$469,900

3 beds

|

2 baths

|

1,732 sq ft

|

House

999 GILLESPIE DR, PALM HARBOR, FL, 34684
Green Dolphin 1250 S PINELLAS AVE 804, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$79,900

1 beds

|

1 baths

|

565 sq ft

|

Condo

1250 S PINELLAS AVE 804, TARPON SPRINGS,...
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.
Edgewater Arms 620 EDGEWATER DR 102, DUNEDIN, FL, 34698, Dunedin, FL 34698
$499,000

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

620 EDGEWATER DR 102, DUNEDIN, FL, 34698
Community: Edgewater Arms
Highland Lakes on Lake Tarpon 1185 ROYAL BLVD, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$439,900

3 beds

|

2 baths

|

1,677 sq ft

|

Villa

1185 ROYAL BLVD, PALM HARBOR, FL, 34684
Timber Oaks 8711 GOLD PINE DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$250,000

3 beds

|

2 baths

|

1,610 sq ft

|

House

8711 GOLD PINE DR, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 2938 MACALPIN DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$489,000

3 beds

|

2 baths

|

1,944 sq ft

|

House

2938 MACALPIN DR, PALM HARBOR, FL, 34684
Summertree 11621 HOLLY ANN DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$254,000

2 beds

|

2 baths

|

1,400 sq ft

|

Villa

11621 HOLLY ANN DR, NEW PORT RICHEY, FL,...
Community: Summertree
Imperial Pines Condominiums 3076 EASTLAND BLVD 210, CLEARWATER, FL, ..., Clearwater, FL 33761
$204,900

2 beds

|

2 baths

|

1,250 sq ft

|

Condo

3076 EASTLAND BLVD 210, CLEARWATER, FL, ...
Timber Oaks 10623 MIRA VISTA DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$249,900

2 beds

|

2 baths

|

1,668 sq ft

|

House

10623 MIRA VISTA DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Green Dolphin 1250 S PINELLAS AVE 214, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$150,000

2 beds

|

2 baths

|

871 sq ft

|

Condo

1250 S PINELLAS AVE 214, TARPON SPRINGS,...
Community: Green Dolphin
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heritage Springs 1249 WINDING WILLOW DR, TRINITY, FL, 346..., Trinity, FL 34655
$340,000

3 beds

|

2 baths

|

1,773 sq ft

|

House

1249 WINDING WILLOW DR, TRINITY, FL, 346...
Community: Heritage Springs
Summertree 11442 TURTLE DOVE PL, NEW PORT RICHEY, F..., New Port Richey, FL 34654
$279,900

2 beds

|

2 baths

|

1,471 sq ft

|

House

11442 TURTLE DOVE PL, NEW PORT RICHEY, F...
Community: Summertree
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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REIN updates its listings on a daily basis. Data last updated: May 25, 2026.
This application does not include information on all of the properties available for sale at this time.

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