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

27 communities 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
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
Heather Lake Condominiums
$100ks
Heather Lake Condominiums, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 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
Summertree
$200ks - $300ks
Summertree, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1974 - 2015 | 800 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
2 rating (1 reviews) Beacon Lakes
$100ks
Beacon Lakes, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 210 homes
Patrician Oaks
$100ks
Patrician Oaks, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 120 homes
Key Vista Villas
$300ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 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
Heather Ridge
$100ks - $200ks
Heather Ridge, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 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
Anchorage
$200ks - $300ks
Anchorage, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 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.
Pinehurst Village
$100ks
Pinehurst Village, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 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
Scotsdale Cluster Condomi...
$200ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 homes
Soleta at Starkey Ranch
$500ks - $600ks
Soleta at Starkey Ranch, Odessa, FL
New Construction | Age-targeted | Built 2023 - present | 139 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
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
New Green Dolphin 1250 S PINELLAS AVE 910, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$89,000

1 beds

|

1 baths

|

669 sq ft

|

Condo

1250 S PINELLAS AVE 910, TARPON SPRINGS,...
Community: Green Dolphin
New Timber Oaks 11220 ELDERBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$244,900

2 beds

|

2 baths

|

1,347 sq ft

|

House

11220 ELDERBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
New Royal Stewart Arms 1 GATESHEAD DR B108, DUNEDIN, FL, 34698, Dunedin, FL 34698
$225,000

1 beds

|

1 baths

|

606 sq ft

|

Condo

1 GATESHEAD DR B108, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
New Green Dolphin 1250 S PINELLAS AVE 306, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$89,900

1 beds

|

1 baths

|

635 sq ft

|

Condo

1250 S PINELLAS AVE 306, TARPON SPRINGS,...
Community: Green Dolphin
New Village on the Green 2572 LAURELWOOD DR 12A, CLEARWATER, FL, ..., Clearwater, FL 33763
$264,900

2 beds

|

2 baths

|

980 sq ft

|

Villa

2572 LAURELWOOD DR 12A, CLEARWATER, FL, ...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
New 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
New Heritage Lake 4817 GRIST MILL CIR 4817, NEW PORT RICHE..., New Port Richey, FL 34655
$209,900

2 beds

|

2 baths

|

962 sq ft

|

Villa

4817 GRIST MILL CIR 4817, NEW PORT RICHE...
Community: Heritage Lake
New Pine Ridge at Palm Harbor 1870 PINE RIDGE WAY G1, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$189,000

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

1870 PINE RIDGE WAY G1, PALM HARBOR, FL,...
New Summertree 11455 GOLF ROUND DR, NEW PORT RICHEY, FL..., New Port Richey, FL 34654
$259,900

3 beds

|

2 baths

|

1,548 sq ft

|

Villa

11455 GOLF ROUND DR, NEW PORT RICHEY, FL...
Community: Summertree
Highland Lakes on Lake Tarpon 3157 MISSION GROVE DR, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$123,000

2 beds

|

1 baths

|

806 sq ft

|

Condo

3157 MISSION GROVE DR, PALM HARBOR, FL, ...
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.
Beacon Lakes 3835 LIGHTHOUSE WAY, NEW PORT RICHEY, FL..., New Port Richey, FL 34652
$155,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

3835 LIGHTHOUSE WAY, NEW PORT RICHEY, FL...
Community: Beacon Lakes
Heritage Springs 1032 DUSTAN PL, TRINITY, FL, 34655, Trinity, FL 34655
$399,000

3 beds

|

2 baths

|

1,704 sq ft

|

House

1032 DUSTAN PL, TRINITY, FL, 34655
Community: Heritage Springs
Timber Oaks 11541 ORLEANS LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$159,500

2 beds

|

2 baths

|

1,152 sq ft

|

Condo

11541 ORLEANS LN, PORT RICHEY, FL, 34668
Community: Timber Oaks
Timber Greens 9413 SUMMERBREEZE TER, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$440,000

3 beds

|

2 baths

|

2,022 sq ft

|

House

9413 SUMMERBREEZE TER, NEW PORT RICHEY, ...
Community: Timber Greens
Highland Lakes on Lake Tarpon 2954 CURLING CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$295,000

2 beds

|

2 baths

|

1,069 sq ft

|

House

2954 CURLING CT, PALM HARBOR, FL, 34684
Highland Lakes on Lake Tarpon 1472 QUEEN ANNE BLVD, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$439,000

2 beds

|

2 baths

|

1,211 sq ft

|

House

1472 QUEEN ANNE BLVD, PALM HARBOR, FL, 3...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 10600 SALAMANCA DR, PORT RICHEY, FL, 346..., Port Richey, FL 34668
$195,000

2 beds

|

2 baths

|

1,107 sq ft

|

House

10600 SALAMANCA DR, PORT RICHEY, FL, 346...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 2472 MALCOLM DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$414,900

2 beds

|

2 baths

|

1,330 sq ft

|

House

2472 MALCOLM DR, PALM HARBOR, FL, 34684
Highland Lakes on Lake Tarpon 2828 HIGHLANDS BLVD A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$249,900

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...
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 9319 TROWBRIDGE CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$207,000

2 beds

|

2 baths

|

1,174 sq ft

|

Villa

9319 TROWBRIDGE CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Heritage Springs 11917 HADLEIGH WAY, TRINITY, FL, 34655, Trinity, FL 34655
$549,900

4 beds

|

4 baths

|

2,635 sq ft

|

House

11917 HADLEIGH WAY, TRINITY, FL, 34655
Community: Heritage Springs
Heritage Springs 1852 ARBOR KNOLL LOOP, TRINITY, FL, 3465..., Trinity, FL 34655
$387,000

3 beds

|

2 baths

|

1,683 sq ft

|

House

1852 ARBOR KNOLL LOOP, TRINITY, FL, 3465...
Community: Heritage Springs
Timber Oaks 11543 ORLEANS LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$189,500

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
$470,000

2 beds

|

2 baths

|

1,699 sq ft

|

House

1647 BENTLEY CT, PALM HARBOR, FL, 34684
Timber Oaks 11530 SAN REMO CT, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$219,900

2 beds

|

2 baths

|

1,197 sq ft

|

Condo

11530 SAN REMO CT, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 1150 ORANGE TREE CIR D, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$225,000

2 beds

|

2 baths

|

960 sq ft

|

Villa

1150 ORANGE TREE CIR D, PALM HARBOR, FL,...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Briar Patch 6419 REMUS DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34653
$235,000

2 beds

|

2 baths

|

1,359 sq ft

|

House

6419 REMUS DR, NEW PORT RICHEY, FL, 3465...
Community: Briar Patch
Timber Oaks 8150 BRADDOCK CIR 3, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$155,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

8150 BRADDOCK CIR 3, PORT RICHEY, FL, 34...
Community: Timber Oaks
Royal Stewart Arms 9 FORBES PLACE PL 112, DUNEDIN, FL, 3469..., Dunedin, FL 34698
$238,000

2 beds

|

2 baths

|

1,181 sq ft

|

Condo

9 FORBES PLACE PL 112, DUNEDIN, FL, 3469...
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.
Patrician Oaks 820 PATRICIA AVE 109, DUNEDIN, FL, 34698, Dunedin, FL 34698
$169,999

2 beds

|

2 baths

|

1,118 sq ft

|

Condo

820 PATRICIA AVE 109, DUNEDIN, FL, 34698
Community: Patrician Oaks
Timber Oaks 11430 CARRIAGE HILL DR 4, PORT RICHEY, F..., Port Richey, FL 34668
$142,000

2 beds

|

2 baths

|

978 sq ft

|

Condo

11430 CARRIAGE HILL DR 4, PORT RICHEY, F...
Community: Timber Oaks
Heritage Lake 9903 KINGSPORT AVE, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$339,900

2 beds

|

2 baths

|

1,822 sq ft

|

House

9903 KINGSPORT AVE, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Heather Lake Condominiums 940 VIRGINIA ST 103, DUNEDIN, FL, 34698, Dunedin, FL 34698
$195,000

2 beds

|

2 baths

|

927 sq ft

|

Condo

940 VIRGINIA ST 103, DUNEDIN, FL, 34698
Briar Patch 4557 GLEN HOLW, NEW PORT RICHEY, FL, 346..., New Port Richey, FL 34653
$189,900

2 beds

|

2 baths

|

964 sq ft

|

Villa

4557 GLEN HOLW, NEW PORT RICHEY, FL, 346...
Community: Briar Patch
Heather Ridge 1485 HALSEY DR 105, DUNEDIN, FL, 34698, Dunedin, FL 34698
$109,000

1 beds

|

1 baths

|

919 sq ft

|

Condo

1485 HALSEY DR 105, DUNEDIN, FL, 34698
Community: Heather Ridge
Heritage Springs 1624 LAKESTONE DR, TRINITY, FL, 34655, Trinity, FL 34655
$460,000

3 beds

|

2 baths

|

2,090 sq ft

|

House

1624 LAKESTONE DR, TRINITY, FL, 34655
Community: Heritage Springs
Timber Oaks 8225 SAN FELIPE CT, PORT RICHEY, FL, 346..., Port Richey, FL 34668
$274,900

2 beds

|

2 baths

|

1,274 sq ft

|

House

8225 SAN FELIPE CT, PORT RICHEY, FL, 346...
Community: Timber Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 10520 SPRINGWOOD DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$260,000

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
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 29, 2026.
This application does not include information on all of the properties available for sale at this time.

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