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Holiday, FL 55+ active adult communities & homes for sale - Page 7

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
Highland Lakes on Lake Tarpon 2828 SHERBROOKE LN C, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$184,000

1 beds

|

2 baths

|

814 sq ft

|

Condo

2828 SHERBROOKE LN C, PALM HARBOR, FL, 3...
Highland Lakes on Lake Tarpon 1012 DUNROBIN DR D, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$259,000

2 beds

|

2 baths

|

1,230 sq ft

|

Villa

1012 DUNROBIN DR D, PALM HARBOR, FL, 346...
Summertree 11427 TURTLE DOVE PL, NEW PORT RICHEY, F..., New Port Richey, FL 34654
$370,000

3 beds

|

2 baths

|

1,686 sq ft

|

House

11427 TURTLE DOVE PL, NEW PORT RICHEY, F...
Community: Summertree
Highland Lakes on Lake Tarpon 3140 HIGHLANDS BLVD F, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$159,900

2 beds

|

2 baths

|

866 sq ft

|

Condo

3140 HIGHLANDS BLVD F, PALM HARBOR, FL, ...
Highland Lakes on Lake Tarpon 3098 E DORCHESTER DR, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$450,000

2 beds

|

2 baths

|

1,567 sq ft

|

House

3098 E DORCHESTER DR, PALM HARBOR, FL, 3...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heritage Lake 9444 ROCKBRIDGE CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$195,000

2 beds

|

2 baths

|

1,335 sq ft

|

Condo

9444 ROCKBRIDGE CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
Village on the Green 2567 OAKLEAF LN 41B, CLEARWATER, FL, 337..., Clearwater, FL 33763
$189,000

2 beds

|

2 baths

|

960 sq ft

|

Villa

2567 OAKLEAF LN 41B, CLEARWATER, FL, 337...
Timber Oaks 8718 BENTON DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$178,000

2 beds

|

2 baths

|

1,218 sq ft

|

House

8718 BENTON DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
Heritage Springs 1201 DUSTAN PL, TRINITY, FL, 34655, Trinity, FL 34655
$399,900

3 beds

|

2 baths

|

2,032 sq ft

|

House

1201 DUSTAN PL, 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.
Royal Stewart Arms 9 HAIG PL 612, DUNEDIN, FL, 34698, Dunedin, FL 34698
$305,000

2 beds

|

2 baths

|

1,181 sq ft

|

Condo

9 HAIG PL 612, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Green Dolphin 1250 S PINELLAS AVE 910, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$122,500

1 beds

|

1 baths

|

669 sq ft

|

Condo

1250 S PINELLAS AVE 910, TARPON SPRINGS,...
Community: Green Dolphin
Heritage Lake 4951 GRIST MILL CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$209,900

2 beds

|

2 baths

|

1,174 sq ft

|

House

4951 GRIST MILL CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
Edgewater Arms 634 EDGEWATER DR 844, DUNEDIN, FL, 34698, Dunedin, FL 34698
$1,100,000

3 beds

|

3 baths

|

2,565 sq ft

|

Condo

634 EDGEWATER DR 844, DUNEDIN, FL, 34698
Community: Edgewater Arms
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Briar Patch 4557 GLEN HOLW, NEW PORT RICHEY, FL, 346..., New Port Richey, FL 34653
$215,000

2 beds

|

2 baths

|

964 sq ft

|

Villa

4557 GLEN HOLW, NEW PORT RICHEY, FL, 346...
Community: Briar Patch
Key Vista Villas 2747 WOOD POINTE DR, HOLIDAY, FL, 34691, Holiday, FL 34691
$349,500

3 beds

|

2 baths

|

1,695 sq ft

|

House

2747 WOOD POINTE DR, HOLIDAY, FL, 34691
Community: Key Vista Villas
Heather Lake Condominiums 940 VIRGINIA ST 304, DUNEDIN, FL, 34698, Dunedin, FL 34698
$137,000

1 beds

|

1 baths

|

760 sq ft

|

Condo

940 VIRGINIA ST 304, DUNEDIN, FL, 34698
Highland Lakes on Lake Tarpon 3116 HIGHLANDS BLVD # 3116, PALM HARBOR,..., Palm Harbor, FL 34684
$140,000

1 beds

|

1 baths

|

636 sq ft

|

Condo

3116 HIGHLANDS BLVD # 3116, PALM HARBOR,...
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 2931 WALNUT GROVE CT, HOLIDAY, FL, 34691, Holiday, FL 34691
$325,000

3 beds

|

2 baths

|

1,341 sq ft

|

House

2931 WALNUT GROVE CT, HOLIDAY, FL, 34691
Community: Key Vista Villas
Timber Oaks 8130 MERRIMAC DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$289,900

2 beds

|

2 baths

|

1,470 sq ft

|

House

8130 MERRIMAC DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
Timber Oaks 11404 STANSBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$269,990

2 beds

|

2 baths

|

1,440 sq ft

|

Villa

11404 STANSBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 2846 HIGHLANDS BLVD D, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$185,000

1 beds

|

2 baths

|

814 sq ft

|

Condo

2846 HIGHLANDS BLVD D, PALM HARBOR, FL, ...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Royal Stewart Arms 7 DUNOON PL 304, DUNEDIN, FL, 34698, Dunedin, FL 34698
$350,000

2 beds

|

2 baths

|

1,141 sq ft

|

Condo

7 DUNOON PL 304, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Green Dolphin 1933 GOLFVIEW DR # 1933, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$264,900

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

1933 GOLFVIEW DR # 1933, TARPON SPRINGS,...
Community: Green Dolphin
Imperial Pines Condominiums 3076 EASTLAND BLVD 210, CLEARWATER, FL, ..., Clearwater, FL 33761
$209,500

2 beds

|

2 baths

|

1,250 sq ft

|

Condo

3076 EASTLAND BLVD 210, CLEARWATER, FL, ...
Timber Oaks 11403 VERSAILLES LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$149,000

2 beds

|

2 baths

|

1,171 sq ft

|

Condo

11403 VERSAILLES LN, 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.
Highland Lakes on Lake Tarpon 3115 MISSION GROVE DR, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$99,900

1 beds

|

1 baths

|

636 sq ft

|

Villa

3115 MISSION GROVE DR, PALM HARBOR, FL, ...
Highland Lakes on Lake Tarpon 3948 TARPON POINTE CIR, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$450,000

3 beds

|

2 baths

|

2,164 sq ft

|

House

3948 TARPON POINTE CIR, PALM HARBOR, FL,...
Pine Ridge at Palm Harbor 1871 PINE RIDGE WAY W APT H3, PALM HARBO..., Palm Harbor, FL 34684
$187,500

2 beds

|

2 baths

|

1,036 sq ft

|

Condo

1871 PINE RIDGE WAY W APT H3, PALM HARBO...
Timber Oaks 11204 PEMBRIDGE CT 4, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$99,900

2 beds

|

2 baths

|

978 sq ft

|

Condo

11204 PEMBRIDGE CT 4, PORT RICHEY, FL, 3...
Community: Timber Oaks
Green Dolphin 1250 S PINELLAS AVE 411, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$115,000

1 beds

|

1 baths

|

565 sq ft

|

Condo

1250 S PINELLAS AVE 411, TARPON SPRINGS,...
Community: Green Dolphin
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Summertree 11248 MOLLYMAWK CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$335,000

3 beds

|

2 baths

|

1,558 sq ft

|

House

11248 MOLLYMAWK CT, NEW PORT RICHEY, FL,...
Community: Summertree
Highland Lakes on Lake Tarpon 2927 MACALPIN DR 9, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$497,999

3 beds

|

3 baths

|

1,535 sq ft

|

House

2927 MACALPIN DR 9, PALM HARBOR, FL, 346...
Highland Lakes on Lake Tarpon 2281 SHELLY DR D, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$214,900

2 beds

|

2 baths

|

918 sq ft

|

Villa

2281 SHELLY DR D, PALM HARBOR, FL, 34684
New Highland Lakes on Lake Tarpon 1319 GLENGARRY DR, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$470,000

3 beds

|

2 baths

|

1,854 sq ft

|

House

1319 GLENGARRY DR, 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.
Heather Lake Condominiums 970 VIRGINIA ST 109, DUNEDIN, FL, 34698, Dunedin, FL 34698
$145,000

2 beds

|

2 baths

|

965 sq ft

|

Condo

970 VIRGINIA ST 109, DUNEDIN, FL, 34698
Heather Lake Condominiums 940 VIRGINIA ST 108, DUNEDIN, FL, 34698, Dunedin, FL 34698
$249,000

2 beds

|

2 baths

|

1,024 sq ft

|

Condo

940 VIRGINIA ST 108, DUNEDIN, FL, 34698
Heather Lake Condominiums 946 VIRGINIA ST APT 102, DUNEDIN, FL, 34..., Dunedin, FL 34698
$137,000

2 beds

|

1 baths

|

1,010 sq ft

|

Condo

946 VIRGINIA ST APT 102, DUNEDIN, FL, 34...
Briar Patch 6428 THICKET TRL, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34653
$220,000

2 beds

|

2 baths

|

964 sq ft

|

Villa

6428 THICKET TRL, NEW PORT RICHEY, FL, 3...
Community: Briar Patch
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Royal Stewart Arms 9 FORBES PL 205, DUNEDIN, FL, 34698, Dunedin, FL 34698
$269,900

2 beds

|

2 baths

|

975 sq ft

|

Condo

9 FORBES PL 205, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Timber Oaks 11543 ORLEANS LN # 11543, PORT RICHEY, F..., Port Richey, FL 34668
$238,000

2 beds

|

2 baths

|

993 sq ft

|

Condo

11543 ORLEANS LN # 11543, PORT RICHEY, F...
Community: Timber Oaks
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