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

292 homes near Holiday

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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
5 rating (1 reviews) Timber Oaks
<$100k - $200ks
Timber Oaks, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1973 - 1997 | 1,000 homes
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
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
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
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
Green Dolphin
$100ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
Esplanade at Starkey Ranc...
$300ks - $700ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only | Age-targeted | Built 2016 - 2022 | 517 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 (2 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
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 - $600ks
Edgewater Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 homes
Victoria Lakes
$800ks - $1Ms
Victoria Lakes, Odessa, FL
New Construction | Age-targeted | Built 2025 - present | 166 homes
Briar Patch
$100ks
Briar Patch, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 homes
Pinehurst Village
$100ks
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
Key Vista Villas
$300ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 homes
Patrician Oaks
$100ks
Patrician Oaks, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 120 homes
Scotsdale Cluster Condomi...
$200ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 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.
Heather Hills Villas
$100ks
Heather Hills Villas, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1971 - 1976 | 64 homes
Anchorage
$200ks - $300ks
Anchorage, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 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
New Port Corners
$200ks - $500ks
New Port Corners, New Port Richey, FL
New Construction | 55+ age-restricted | Built 2025 - present
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
Heather Ridge
$100ks - $200ks
Heather Ridge, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Soleta at Starkey Ranch
$500ks - $600ks
Soleta at Starkey Ranch, Odessa, FL
New Construction | Age-targeted | Built 2023 - present | 139 homes
Highland Lakes on Lake Tarpon 3472 MACLAREN DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$319,900

2 beds

|

2 baths

|

1,289 sq ft

|

Villa

3472 MACLAREN DR, PALM HARBOR, FL, 34684
Timber Greens 6240 FAIRSKIES DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$349,000

2 beds

|

2 baths

|

1,558 sq ft

|

Villa

6240 FAIRSKIES DR, NEW PORT RICHEY, FL, ...
Community: Timber Greens
Timber Oaks 11220 ELDERBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$240,000

2 beds

|

2 baths

|

1,347 sq ft

|

House

11220 ELDERBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Royal Stewart Arms 1 GATESHEAD DR B108, DUNEDIN, FL, 34698, Dunedin, FL 34698
$195,000

1 beds

|

1 baths

|

606 sq ft

|

Condo

1 GATESHEAD DR B108, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Heather Lake Condominiums 970 VIRGINIA ST 107, DUNEDIN, FL, 34698, Dunedin, FL 34698
$145,000

2 beds

|

1 baths

|

965 sq ft

|

Condo

970 VIRGINIA ST 107, DUNEDIN, FL, 34698
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Cindy Certified
270 DIOGENES ST, DUNEDIN, FL, 34698, Dunedin, FL 34698
$549,000

3 beds

|

2 baths

|

1,364 sq ft

|

House

270 DIOGENES ST, DUNEDIN, FL, 34698
Cindy Certified
266 PLATON AVE, DUNEDIN, FL, 34698, Dunedin, FL 34698
$549,000

3 beds

|

2 baths

|

1,380 sq ft

|

House

266 PLATON AVE, DUNEDIN, FL, 34698
Highland Lakes on Lake Tarpon 3157 MISSION GROVE DR, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$117,000

2 beds

|

1 baths

|

806 sq ft

|

Condo

3157 MISSION GROVE DR, PALM HARBOR, FL, ...
Beacon Lakes 3835 LIGHTHOUSE WAY, NEW PORT RICHEY, FL..., New Port Richey, FL 34652
$138,500

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

3835 LIGHTHOUSE WAY, NEW PORT RICHEY, FL...
Community: Beacon Lakes
Highland Lakes on Lake Tarpon 1472 QUEEN ANNE BLVD, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$419,000

2 beds

|

2 baths

|

1,211 sq ft

|

House

1472 QUEEN ANNE BLVD, PALM HARBOR, FL, 3...
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 2828 HIGHLANDS BLVD A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$244,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

2828 HIGHLANDS BLVD A, PALM HARBOR, FL, ...
Highland Lakes on Lake Tarpon 860 MACLAREN DR B, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$259,900

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

860 MACLAREN DR B, PALM HARBOR, FL, 3468...
Heritage Lake 9319 TROWBRIDGE CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$189,000

2 beds

|

2 baths

|

1,174 sq ft

|

Villa

9319 TROWBRIDGE CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Timber Oaks 11543 ORLEANS LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$180,000

2 beds

|

2 baths

|

993 sq ft

|

Condo

11543 ORLEANS LN, PORT RICHEY, FL, 34668
Community: Timber Oaks
Highland Lakes on Lake Tarpon 1647 BENTLEY CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$440,000

2 beds

|

2 baths

|

1,699 sq ft

|

House

1647 BENTLEY CT, PALM HARBOR, FL, 34684
Briar Patch 6419 REMUS DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34653
$199,000

2 beds

|

2 baths

|

1,359 sq ft

|

House

6419 REMUS DR, NEW PORT RICHEY, FL, 3465...
Community: Briar Patch
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Green Dolphin 1250 S PINELLAS AVE 711, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$117,500

1 beds

|

1 baths

|

565 sq ft

|

Condo

1250 S PINELLAS AVE 711, TARPON SPRINGS,...
Community: Green Dolphin
Timber Oaks 8150 BRADDOCK CIR 3, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$150,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

8150 BRADDOCK CIR 3, PORT RICHEY, FL, 34...
Community: Timber Oaks
Briar Patch 4557 GLEN HOLW, NEW PORT RICHEY, FL, 346..., New Port Richey, FL 34653
$179,900

2 beds

|

2 baths

|

964 sq ft

|

Villa

4557 GLEN HOLW, NEW PORT RICHEY, FL, 346...
Community: Briar Patch
Timber Oaks 8225 SAN FELIPE CT, PORT RICHEY, FL, 346..., Port Richey, FL 34668
$269,800

2 beds

|

2 baths

|

1,560 sq ft

|

House

8225 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.
Timber Oaks 10520 SPRINGWOOD DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$239,900

2 beds

|

2 baths

|

1,218 sq ft

|

House

10520 SPRINGWOOD DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Heather Lake Condominiums 948 VIRGINIA ST 207, DUNEDIN, FL, 34698, Dunedin, FL 34698
$125,000

1 beds

|

1 baths

|

869 sq ft

|

Condo

948 VIRGINIA ST 207, DUNEDIN, FL, 34698
Beacon Lakes 3836 LIGHTHOUSE WAY 3836, NEW PORT RICHE..., New Port Richey, FL 34652
$130,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

3836 LIGHTHOUSE WAY 3836, NEW PORT RICHE...
Community: Beacon Lakes
Heritage Lake 9058 ARUNDLE PL, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34655
$224,900

2 beds

|

2 baths

|

1,553 sq ft

|

Condo

9058 ARUNDLE PL, NEW PORT RICHEY, FL, 34...
Community: Heritage Lake
Timber Oaks 11210 CARRIAGE HILL DR 5, PORT RICHEY, F..., Port Richey, FL 34668
$127,900

2 beds

|

2 baths

|

954 sq ft

|

Condo

11210 CARRIAGE HILL DR 5, PORT RICHEY, F...
Community: Timber Oaks
Patrician Oaks 840 VIRGINIA ST 303, DUNEDIN, FL, 34698, Dunedin, FL 34698
$119,000

2 beds

|

1 baths

|

1,004 sq ft

|

Condo

840 VIRGINIA ST 303, DUNEDIN, FL, 34698
Community: Patrician Oaks
Pine Ridge at Palm Harbor 2687 PINE RIDGE WAY H1, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$180,000

2 beds

|

2 baths

|

1,104 sq ft

|

Condo

2687 PINE RIDGE WAY H1, PALM HARBOR, FL,...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Pine Ridge at Palm Harbor 2642 PINE RIDGE WAY G2, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$189,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

2642 PINE RIDGE WAY G2, PALM HARBOR, FL,...
Timber Oaks 10636 SALAMANCA DR, PORT RICHEY, FL, 346..., Port Richey, FL 34668
$210,000

2 beds

|

2 baths

|

1,332 sq ft

|

House

10636 SALAMANCA DR, PORT RICHEY, FL, 346...
Community: Timber Oaks
Timber Greens 9631 OAKWOOD HILLS CT, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$499,999

3 beds

|

2 baths

|

1,888 sq ft

|

House

9631 OAKWOOD HILLS CT, NEW PORT RICHEY, ...
Community: Timber Greens
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 139, DUNEDIN, FL, 34698, Dunedin, FL 34698
$299,700

2 beds

|

2 baths

|

1,330 sq ft

|

Condo

632 EDGEWATER DR 139, DUNEDIN, FL, 34698
Community: Edgewater Arms
Heather Lake Condominiums 936 VIRGINIA ST 201, DUNEDIN, FL, 34698, Dunedin, FL 34698
$140,000

2 beds

|

2 baths

|

1,024 sq ft

|

Condo

936 VIRGINIA ST 201, DUNEDIN, FL, 34698
Heritage Lake 4968 GRIST MILL CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$159,900

2 beds

|

2 baths

|

962 sq ft

|

Villa

4968 GRIST MILL CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
Timber Oaks 10541 GREEN MEADOW LN, PORT RICHEY, FL, ..., Port Richey, FL 34668
$260,000

2 beds

|

2 baths

|

1,422 sq ft

|

House

10541 GREEN MEADOW LN, PORT RICHEY, FL, ...
Community: Timber Oaks
Heritage Springs 1300 FALLOWFIELD DR, TRINITY, FL, 34655, Trinity, FL 34655
$425,000

2 beds

|

2 baths

|

1,870 sq ft

|

House

1300 FALLOWFIELD DR, TRINITY, FL, 34655
Community: Heritage Springs
Heather Lake Condominiums 946 VIRGINIA ST 107, DUNEDIN, FL, 34698, Dunedin, FL 34698
$150,000

2 beds

|

1 baths

|

1,010 sq ft

|

Condo

946 VIRGINIA ST 107, DUNEDIN, FL, 34698
Timber Greens 10036 BROOKDALE DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$335,000

3 beds

|

2 baths

|

1,694 sq ft

|

House

10036 BROOKDALE DR, NEW PORT RICHEY, FL,...
Community: Timber Greens
Highland Lakes on Lake Tarpon 2740 HIGHLANDS BLVD B, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$185,000

2 beds

|

2 baths

|

1,000 sq ft

|

Villa

2740 HIGHLANDS BLVD B, PALM HARBOR, FL, ...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Key Vista Villas 2815 WOOD POINTE DR, HOLIDAY, FL, 34691, Holiday, FL 34691
$359,900

3 beds

|

2 baths

|

1,819 sq ft

|

House

2815 WOOD POINTE DR, HOLIDAY, FL, 34691
Community: Key Vista Villas
Heritage Springs 1444 CANBERLEY CT, TRINITY, FL, 34655, Trinity, FL 34655
$369,000

2 beds

|

2 baths

|

1,837 sq ft

|

House

1444 CANBERLEY CT, TRINITY, FL, 34655
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.
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