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

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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Questions? Call us: (727) 800-3371
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
Pine Ridge at Palm Harbor 1737 PINE RIDGE WAY W A, PALM HARBOR, FL..., Palm Harbor, FL 34684
$155,000

2 beds

|

1 baths

|

904 sq ft

|

Condo

1737 PINE RIDGE WAY W A, PALM HARBOR, FL...
Timber Oaks 8040 PASADENA DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$227,500

2 beds

|

2 baths

|

1,650 sq ft

|

House

8040 PASADENA DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
Heather Lake Condominiums 960 VIRGINIA ST 307, DUNEDIN, FL, 34698, Dunedin, FL 34698
$109,900

1 beds

|

1 baths

|

800 sq ft

|

Condo

960 VIRGINIA ST 307, DUNEDIN, FL, 34698
Heritage Springs 12148 ARRON TER, TRINITY, FL, 34655, Trinity, FL 34655
$355,000

2 beds

|

2 baths

|

1,594 sq ft

|

Villa

12148 ARRON TER, TRINITY, FL, 34655
Community: Heritage Springs
Highland Lakes on Lake Tarpon 2738 SHERBROOKE LN C, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$155,000

1 beds

|

2 baths

|

814 sq ft

|

Villa

2738 SHERBROOKE LN C, PALM HARBOR, FL, 3...
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Questions? Call us: (727) 800-3371
Heritage Lake 4720 SHEFFIELD DR # 4720, NEW PORT RICHE..., New Port Richey, FL 34655
$184,900

2 beds

|

2 baths

|

1,204 sq ft

|

Condo

4720 SHEFFIELD DR # 4720, NEW PORT RICHE...
Community: Heritage Lake
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 2113 MALCOLM DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$374,916

2 beds

|

2 baths

|

1,535 sq ft

|

House

2113 MALCOLM DR, PALM HARBOR, FL, 34684
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
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 8330 HIGH POINT CIR APT 6, PORT RICHEY, ..., Port Richey, FL 34668
$204,000

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

8330 HIGH POINT CIR APT 6, PORT RICHEY, ...
Community: Timber Oaks
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
Heritage Lake 4707 WALLINGFORD CT # 4707, NEW PORT RIC..., New Port Richey, FL 34655
$154,900

2 beds

|

2 baths

|

1,401 sq ft

|

Condo

4707 WALLINGFORD CT # 4707, NEW PORT RIC...
Community: Heritage Lake
Green Dolphin 1250 S PINELLAS AVE 307, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$109,000

1 beds

|

1 baths

|

669 sq ft

|

Condo

1250 S PINELLAS AVE 307, 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 3184 BRUNSWICK CIR, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$445,000

2 beds

|

2 baths

|

1,950 sq ft

|

House

3184 BRUNSWICK CIR, PALM HARBOR, FL, 346...
Royal Stewart Arms 7 DUNOON PL APT 306, DUNEDIN, FL, 34698, Dunedin, FL 34698
$375,000

2 beds

|

2 baths

|

1,141 sq ft

|

Condo

7 DUNOON PL APT 306, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Pinehurst Village 1701 PINEHURST RD 24E, DUNEDIN, FL, 3469..., Dunedin, FL 34698
$110,000

1 beds

|

1 baths

|

645 sq ft

|

Condo

1701 PINEHURST RD 24E, DUNEDIN, FL, 3469...
Community: Pinehurst Village
Timber Oaks 10521 MIRA VISTA DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$245,000

2 beds

|

2 baths

|

1,432 sq ft

|

House

10521 MIRA VISTA DR, PORT RICHEY, FL, 34...
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.
Key Vista Villas 2514 SANDY HILL CT, HOLIDAY, FL, 34691, Holiday, FL 34691
$345,900

2 beds

|

2 baths

|

1,555 sq ft

|

House

2514 SANDY HILL CT, HOLIDAY, FL, 34691
Community: Key Vista Villas
Briar Patch 6506 THICKET TRL, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34653
$220,000

2 beds

|

2 baths

|

964 sq ft

|

Villa

6506 THICKET TRL, NEW PORT RICHEY, FL, 3...
Community: Briar Patch
Heritage Lake 9643 NOBLE CT, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34655
$259,900

2 beds

|

2 baths

|

1,230 sq ft

|

House

9643 NOBLE CT, NEW PORT RICHEY, FL, 3465...
Community: Heritage Lake
Highland Lakes on Lake Tarpon 3681 RIDGEMONT CT, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$350,000

2 beds

|

2 baths

|

1,372 sq ft

|

Villa

3681 RIDGEMONT CT, PALM HARBOR, FL, 3468...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 10619 MIRA VISTA DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$230,000

2 beds

|

2 baths

|

1,476 sq ft

|

House

10619 MIRA VISTA DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Green Dolphin 1934 GOLFVIEW DR # 1934, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$224,000

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

1934 GOLFVIEW DR # 1934, TARPON SPRINGS,...
Community: Green Dolphin
Beacon Lakes 4445 PELORUS DR, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34652
$129,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

4445 PELORUS DR, NEW PORT RICHEY, FL, 34...
Community: Beacon Lakes
Highland Lakes on Lake Tarpon 2211 LARK CIR D, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$235,000

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

2211 LARK CIR D, PALM HARBOR, FL, 34684
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 Lake 9433 STONEWALL LN, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$294,900

2 beds

|

2 baths

|

1,826 sq ft

|

House

9433 STONEWALL LN, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
Summertree 11806 WHITE ASH DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$189,900

3 beds

|

2 baths

|

1,349 sq ft

|

House

11806 WHITE ASH DR, NEW PORT RICHEY, FL,...
Community: Summertree
Highland Lakes on Lake Tarpon 3251 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$349,900

2 beds

|

2 baths

|

1,332 sq ft

|

Villa

3251 MCMATH DR, PALM HARBOR, FL, 34684
Green Dolphin 1250 S PINELLAS AVE 403, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$125,000

1 beds

|

1 baths

|

669 sq ft

|

Condo

1250 S PINELLAS AVE 403, TARPON SPRINGS,...
Community: Green Dolphin
Key Vista Villas 2211 PLEASANT HILL LN, HOLIDAY, FL, 3469..., Holiday, FL 34691
$341,900

2 beds

|

2 baths

|

1,500 sq ft

|

House

2211 PLEASANT HILL LN, HOLIDAY, FL, 3469...
Community: Key Vista Villas
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 10800 TEER LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$245,000

2 beds

|

2 baths

|

1,522 sq ft

|

House

10800 TEER LN, PORT RICHEY, FL, 34668
Community: Timber Oaks
Briar Patch 6531 REMUS DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34653
$215,000

3 beds

|

2 baths

|

1,359 sq ft

|

Townhouse

6531 REMUS DR, NEW PORT RICHEY, FL, 3465...
Community: Briar Patch
Esplanade at Starkey Ranch 11398 JUGLANS DR, ODESSA, FL, 33556, Odessa, FL 33556
$879,000

3 beds

|

3 baths

|

2,410 sq ft

|

House

11398 JUGLANS DR, ODESSA, FL, 33556
Timber Oaks 8420 WINDING WOOD DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$235,000

2 beds

|

2 baths

|

1,274 sq ft

|

House

8420 WINDING WOOD DR, PORT RICHEY, FL, 3...
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.
Green Dolphin 1250 S PINELLAS AVE APT 214, TARPON SPRI..., Tarpon Springs, FL 34689
$160,000

2 beds

|

2 baths

|

871 sq ft

|

Condo

1250 S PINELLAS AVE APT 214, TARPON SPRI...
Community: Green Dolphin
Royal Stewart Arms 5 GATESHEAD DR APT 107, DUNEDIN, FL, 346..., Dunedin, FL 34698
$450,000

2 beds

|

2 baths

|

1,014 sq ft

|

Condo

5 GATESHEAD DR APT 107, DUNEDIN, FL, 346...
Community: Royal Stewart Arms
Timber Oaks 11231 DOLLAR LAKE DR APT 1, PORT RICHEY,..., Port Richey, FL 34668
$145,000

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

11231 DOLLAR LAKE DR APT 1, PORT RICHEY,...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 2735 SHERBROOKE LN A, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$224,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

2735 SHERBROOKE LN A, PALM HARBOR, FL, 3...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Royal Stewart Arms 2 CAUSEWAY BLVD 101, DUNEDIN, FL, 34698, Dunedin, FL 34698
$340,000

2 beds

|

2 baths

|

1,040 sq ft

|

Condo

2 CAUSEWAY BLVD 101, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Patrician Oaks 870 VIRGINIA ST APT 113, DUNEDIN, FL, 34..., Dunedin, FL 34698
$140,000

2 beds

|

1 baths

|

973 sq ft

|

Condo

870 VIRGINIA ST APT 113, DUNEDIN, FL, 34...
Community: Patrician Oaks
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