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

265 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
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
Heather Lake Condominiums
$100ks
Heather Lake Condominiums, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 homes
Edgewater Arms
$400ks - $600ks
Edgewater Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 homes
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
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
2 rating (1 reviews) Beacon Lakes
$100ks
Beacon Lakes, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 210 homes
Pinehurst Village
$100ks
Pinehurst Village, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 homes
Green Dolphin
$100ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
Victoria Lakes
$800ks - $1Ms
Victoria Lakes, Odessa, FL
New Construction | Age-targeted | Built 2025 - present | 166 homes
Key Vista Villas
$300ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Esplanade at Starkey Ranc...
$300ks - $700ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only | Age-targeted | Built 2016 - 2022 | 517 homes
Patrician Oaks
$100ks
Patrician Oaks, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 120 homes
Imperial Pines Condominiu...
$100ks - $200ks
Imperial Pines Condominiu..., Clearwater, FL
Resale Only | 55+ age-restricted | Built 1985 - 1985 | 181 homes
Heather Ridge
$100ks - $200ks
Heather Ridge, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 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
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
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
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
New Port Corners
$200ks - $500ks
New Port Corners, New Port Richey, FL
New Construction | 55+ age-restricted | Built 2025 - present
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
$172,000

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

4808 VESPER CT 34, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
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
Green Dolphin 1250 S PINELLAS AVE 804, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$78,900

1 beds

|

1 baths

|

565 sq ft

|

Condo

1250 S PINELLAS AVE 804, TARPON SPRINGS,...
Community: Green Dolphin
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
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 8345 ELGIN DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$240,000

2 beds

|

2 baths

|

1,454 sq ft

|

House

8345 ELGIN DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
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, ...
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
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
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.
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
Highland Lakes on Lake Tarpon 1121 QUEEN ANNE DR C, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$150,000

2 beds

|

2 baths

|

1,000 sq ft

|

Villa

1121 QUEEN ANNE DR C, PALM HARBOR, FL, 3...
Royal Stewart Arms 7 DUNOON PL 102, DUNEDIN, FL, 34698, Dunedin, FL 34698
$270,000

1 beds

|

1 baths

|

957 sq ft

|

Condo

7 DUNOON PL 102, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Briar Patch 4505 GLEN HOLW, NEW PORT RICHEY, FL, 346..., New Port Richey, FL 34653
$235,000

2 beds

|

3 baths

|

1,453 sq ft

|

Townhouse

4505 GLEN HOLW, NEW PORT RICHEY, FL, 346...
Community: Briar Patch
Timber Oaks 11241 DOLLAR LAKE DR 4, PORT RICHEY, FL,..., Port Richey, FL 34668
$130,000

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

11241 DOLLAR LAKE DR 4, PORT RICHEY, FL,...
Community: Timber Oaks
Country Oaks 7804 EUREKA DR, HUDSON, FL, 34667, Hudson, FL 34667
$140,000

2 beds

|

2 baths

|

1,049 sq ft

|

Condo

7804 EUREKA DR, HUDSON, FL, 34667
Community: Country Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Key Vista Villas 2211 PLEASANT HILL LN, HOLIDAY, FL, 3469..., Holiday, FL 34691
$300,000

2 beds

|

2 baths

|

1,500 sq ft

|

Villa

2211 PLEASANT HILL LN, HOLIDAY, FL, 3469...
Community: Key Vista Villas
Timber Greens 6353 CARDINAL CREST DR, NEW PORT RICHEY,..., New Port Richey, FL 34655
$389,000

3 beds

|

2 baths

|

1,709 sq ft

|

House

6353 CARDINAL CREST DR, NEW PORT RICHEY,...
Community: Timber Greens
Heather Hills Villas 852 OXFORD CT, DUNEDIN, FL, 34698, Dunedin, FL 34698
$225,000

2 beds

|

2 baths

|

999 sq ft

|

Villa

852 OXFORD CT, DUNEDIN, FL, 34698
Pinehurst Village 1701 PINEHURST RD 18C, DUNEDIN, FL, 3469..., Dunedin, FL 34698
$149,900

2 beds

|

1 baths

|

875 sq ft

|

Villa

1701 PINEHURST RD 18C, DUNEDIN, FL, 3469...
Community: Pinehurst Village
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 865 VIRGINIA CT 108, DUNEDIN, FL, 34698, Dunedin, FL 34698
$154,000

2 beds

|

2 baths

|

1,040 sq ft

|

Condo

865 VIRGINIA CT 108, DUNEDIN, FL, 34698
Community: Patrician Oaks
Highland Lakes on Lake Tarpon 3305 GORSE CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$339,000

2 beds

|

2 baths

|

1,148 sq ft

|

Villa

3305 GORSE CT, PALM HARBOR, FL, 34684
Highland Lakes on Lake Tarpon 1001 TARTAN DR 302, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$199,500

2 beds

|

2 baths

|

980 sq ft

|

Condo

1001 TARTAN DR 302, PALM HARBOR, FL, 346...
Timber Oaks 11308 VERSAILLES LN C, PORT RICHEY, FL, ..., Port Richey, FL 34668
$199,900

2 beds

|

2 baths

|

1,171 sq ft

|

Condo

11308 VERSAILLES LN C, PORT RICHEY, FL, ...
Community: Timber Oaks
Edgewater Arms 620 EDGEWATER DRS 103, DUNEDIN, FL, 3469..., Dunedin, FL 34698
$274,000

1 beds

|

1 baths

|

840 sq ft

|

Condo

620 EDGEWATER DRS 103, DUNEDIN, FL, 3469...
Community: Edgewater Arms
Royal Stewart Arms 7 ELGIN PL 301, DUNEDIN, FL, 34698, Dunedin, FL 34698
$349,000

2 beds

|

2 baths

|

1,181 sq ft

|

Condo

7 ELGIN PL 301, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Royal Stewart Arms 7 DUNOON PL 104, DUNEDIN, FL, 34698, Dunedin, FL 34698
$340,000

2 beds

|

2 baths

|

1,141 sq ft

|

Condo

7 DUNOON PL 104, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Esplanade at Starkey Ranch 11414 JUGLANS DR, ODESSA, FL, 33556, Odessa, FL 33556
$749,000

4 beds

|

3 baths

|

2,466 sq ft

|

House

11414 JUGLANS DR, ODESSA, FL, 33556
Green Dolphin 2014 GOLFVIEW DR 2014, TARPON SPRINGS, F..., Tarpon Springs, FL 34689
$224,900

3 beds

|

2 baths

|

1,560 sq ft

|

Condo

2014 GOLFVIEW DR 2014, TARPON SPRINGS, F...
Community: Green Dolphin
Timber Oaks 11341 DOLLAR LAKE DR 1, PORT RICHEY, FL,..., Port Richey, FL 34668
$159,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

11341 DOLLAR LAKE DR 1, PORT RICHEY, FL,...
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 8030 GLENEAGLE DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$209,900

2 beds

|

2 baths

|

1,001 sq ft

|

House

8030 GLENEAGLE DR, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Pinehurst Village 1701 PINEHURST RD 6A, DUNEDIN, FL, 34698, Dunedin, FL 34698
$179,900

2 beds

|

2 baths

|

1,025 sq ft

|

Condo

1701 PINEHURST RD 6A, DUNEDIN, FL, 34698
Community: Pinehurst Village
Anchorage 819 HELMSMAN WAY, PALM HARBOR, FL, 34685, Palm Harbor, FL 34685
$364,900

3 beds

|

2 baths

|

1,344 sq ft

|

House

819 HELMSMAN WAY, PALM HARBOR, FL, 34685
Community: Anchorage
Summertree 11129 KISKADEE CIR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$310,000

3 beds

|

2 baths

|

1,554 sq ft

|

House

11129 KISKADEE CIR, NEW PORT RICHEY, FL,...
Community: Summertree
Heritage Springs 1237 RAMBLING VINE CT, TRINITY, FL, 3465..., Trinity, FL 34655
$563,000

3 beds

|

2 baths

|

2,409 sq ft

|

House

1237 RAMBLING VINE CT, TRINITY, FL, 3465...
Community: Heritage Springs
Timber Oaks 11210 CARRIAGE HILL DR 2, PORT RICHEY, F..., Port Richey, FL 34668
$119,900

2 beds

|

2 baths

|

954 sq ft

|

Condo

11210 CARRIAGE HILL DR 2, PORT RICHEY, F...
Community: Timber Oaks
Timber Oaks 11117 PEMBRIDGE CT 2, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$96,000

2 beds

|

1 baths

|

882 sq ft

|

Condo

11117 PEMBRIDGE CT 2, PORT RICHEY, FL, 3...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 102 STAFFORD DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$379,900

2 beds

|

2 baths

|

1,264 sq ft

|

House

102 STAFFORD DR, PALM HARBOR, FL, 34684
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Summertree 11829 IVYWOOD PL, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34654
$259,000

3 beds

|

2 baths

|

1,632 sq ft

|

House

11829 IVYWOOD PL, NEW PORT RICHEY, FL, 3...
Community: Summertree
Summertree 11519 HOLLY ANN DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$244,900

3 beds

|

2 baths

|

1,834 sq ft

|

Villa

11519 HOLLY ANN DR, NEW PORT RICHEY, FL,...
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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