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

272 homes 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
Heather Lake Condominiums
$100ks
Heather Lake Condominiums, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 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
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
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
Key Vista Villas
$300ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 homes
2 rating (1 reviews) Beacon Lakes
$100ks
Beacon Lakes, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 210 homes
Imperial Pines Condominiu...
$100ks - $200ks
Imperial Pines Condominiu..., Clearwater, FL
Resale Only | 55+ age-restricted | Built 1985 - 1985 | 181 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
Patrician Oaks
$100ks
Patrician Oaks, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 120 homes
Anchorage
$200ks - $300ks
Anchorage, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 homes
Heather Ridge
$100ks - $200ks
Heather Ridge, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 homes
Pinehurst Village
$100ks
Pinehurst Village, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 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
Scotsdale Cluster Condomi...
$200ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 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
Linkside Village
$200ks
Linkside Village, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 100 homes
Soleta at Starkey Ranch
$500ks - $600ks
Soleta at Starkey Ranch, Odessa, FL
New Construction | Age-targeted | Built 2023 - present | 139 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
Timber Oaks 11241 VERSAILLES LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$159,900

2 beds

|

2 baths

|

1,037 sq ft

|

Condo

11241 VERSAILLES LN, PORT RICHEY, FL, 34...
Community: Timber Oaks
Heritage Lake 4739 CARRINGTON CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$210,000

2 beds

|

2 baths

|

1,261 sq ft

|

Condo

4739 CARRINGTON CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Timber Oaks 8111 BRADDOCK CIR 6, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$140,000

2 beds

|

2 baths

|

1,210 sq ft

|

Villa

8111 BRADDOCK CIR 6, PORT RICHEY, FL, 34...
Community: Timber Oaks
Heather Lake Condominiums 940 VIRGINIA ST 108, DUNEDIN, FL, 34698, Dunedin, FL 34698
$213,000

2 beds

|

2 baths

|

1,024 sq ft

|

Condo

940 VIRGINIA ST 108, DUNEDIN, FL, 34698
Royal Stewart Arms 8 GLENCOE PL 307, DUNEDIN, FL, 34698, Dunedin, FL 34698
$215,000

2 beds

|

1 baths

|

1,100 sq ft

|

Condo

8 GLENCOE PL 307, 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
Timber Greens 5930 PRECIOUS VIEW CT, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$332,500

2 beds

|

2 baths

|

1,855 sq ft

|

Villa

5930 PRECIOUS VIEW CT, NEW PORT RICHEY, ...
Community: Timber Greens
Heather Lake Condominiums 960 VIRGINIA ST 107, DUNEDIN, FL, 34698, Dunedin, FL 34698
$97,000

1 beds

|

1 baths

|

800 sq ft

|

Condo

960 VIRGINIA ST 107, DUNEDIN, FL, 34698
Heritage Lake 4719 CAVENDISH DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$288,400

2 beds

|

2 baths

|

1,646 sq ft

|

House

4719 CAVENDISH DR, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
Heritage Lake 4658 WALLINGFORD CT, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$237,999

2 beds

|

2 baths

|

1,204 sq ft

|

Condo

4658 WALLINGFORD CT, NEW PORT RICHEY, FL...
Community: Heritage Lake
Heritage Springs 12202 ARRON TER, TRINITY, FL, 34655, Trinity, FL 34655
$369,000

2 beds

|

2 baths

|

1,873 sq ft

|

Villa

12202 ARRON TER, 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.
Summertree 11805 LOBLOLLY PINE DR, NEW PORT RICHEY,..., New Port Richey, FL 34654
$235,000

2 beds

|

2 baths

|

1,223 sq ft

|

House

11805 LOBLOLLY PINE DR, NEW PORT RICHEY,...
Community: Summertree
Green Dolphin 1250 S PINELLAS AVE 910, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$99,000

1 beds

|

1 baths

|

669 sq ft

|

Condo

1250 S PINELLAS AVE 910, TARPON SPRINGS,...
Community: Green Dolphin
Pine Ridge at Palm Harbor 2575 PINE RIDGE WAY E1, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$189,000

2 beds

|

2 baths

|

1,085 sq ft

|

Condo

2575 PINE RIDGE WAY E1, PALM HARBOR, FL,...
Timber Oaks 11414 STANSBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$249,500

2 beds

|

2 baths

|

1,387 sq ft

|

Villa

11414 STANSBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Royal Stewart Arms 7 DUNOON PL 304, DUNEDIN, FL, 34698, Dunedin, FL 34698
$299,500

2 beds

|

2 baths

|

1,141 sq ft

|

Condo

7 DUNOON PL 304, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Timber Oaks 11404 STANSBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$249,990

2 beds

|

2 baths

|

1,440 sq ft

|

Villa

11404 STANSBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
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...
Briar Patch 6421 REMUS DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34653
$178,900

2 beds

|

2 baths

|

964 sq ft

|

Villa

6421 REMUS DR, NEW PORT RICHEY, FL, 3465...
Community: Briar Patch
Highland Lakes on Lake Tarpon 2722 SHERBROOKE LN D, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$145,000

1 beds

|

1 baths

|

814 sq ft

|

Condo

2722 SHERBROOKE LN D, PALM HARBOR, FL, 3...
Heather Hills Villas 832 CAMBRIDGE CT, DUNEDIN, FL, 34698, Dunedin, FL 34698
$159,900

1 beds

|

1 baths

|

739 sq ft

|

Villa

832 CAMBRIDGE CT, 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.
Imperial Pines Condominiums 3062 EASTLAND BLVD 308, CLEARWATER, FL, ..., Clearwater, FL 33761
$240,000

2 beds

|

2 baths

|

1,565 sq ft

|

Condo

3062 EASTLAND BLVD 308, CLEARWATER, FL, ...
Esplanade at Starkey Ranch 11398 JUGLANS DR, ODESSA, FL, 33556, Odessa, FL 33556
$815,000

3 beds

|

3 baths

|

2,410 sq ft

|

House

11398 JUGLANS DR, ODESSA, FL, 33556
Beacon Lakes 3838 LANYARD CT, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34652
$108,500

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

3838 LANYARD CT, NEW PORT RICHEY, FL, 34...
Community: Beacon Lakes
Pinehurst Village 1701 PINEHURST RD 16C, DUNEDIN, FL, 3469..., Dunedin, FL 34698
$179,900

2 beds

|

1 baths

|

875 sq ft

|

Condo

1701 PINEHURST RD 16C, DUNEDIN, FL, 3469...
Community: Pinehurst Village
Summertree 11248 MOLLYMAWK CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$330,000

3 beds

|

2 baths

|

1,558 sq ft

|

House

11248 MOLLYMAWK CT, NEW PORT RICHEY, FL,...
Community: Summertree
Briar Patch 6516 REMUS DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34653
$175,000

2 beds

|

2 baths

|

964 sq ft

|

Villa

6516 REMUS DR, NEW PORT RICHEY, FL, 3465...
Community: Briar Patch
Heather Lake Condominiums 940 VIRGINIA ST 304, DUNEDIN, FL, 34698, Dunedin, FL 34698
$111,000

1 beds

|

1 baths

|

760 sq ft

|

Condo

940 VIRGINIA ST 304, DUNEDIN, FL, 34698
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 10819 LOS SANTOS DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$160,000

2 beds

|

2 baths

|

1,107 sq ft

|

House

10819 LOS SANTOS DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Timber Oaks 11310 CARRIAGE HILL DR 4, PORT RICHEY, F..., Port Richey, FL 34668
$104,900

2 beds

|

2 baths

|

978 sq ft

|

Condo

11310 CARRIAGE HILL DR 4, PORT RICHEY, F...
Community: Timber Oaks
Summertree 11521 ROSE TREE DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$260,000

2 beds

|

2 baths

|

1,777 sq ft

|

House

11521 ROSE TREE 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.
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
Patrician Oaks 820 VIRGINIA ST 207, DUNEDIN, FL, 34698, Dunedin, FL 34698
$125,000

2 beds

|

1 baths

|

1,004 sq ft

|

Condo

820 VIRGINIA ST 207, DUNEDIN, FL, 34698
Community: Patrician Oaks

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