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Holiday, FL 55+ active adult communities & homes for sale - Page 6

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
Timber Oaks 8330 HIGH POINT CIR 6, PORT RICHEY, FL, ..., Port Richey, FL 34668
$179,900

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

8330 HIGH POINT CIR 6, PORT RICHEY, FL, ...
Community: Timber Oaks
Summertree 11415 WINDSTAR CT, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34654
$320,000

3 beds

|

2 baths

|

1,738 sq ft

|

House

11415 WINDSTAR CT, NEW PORT RICHEY, FL, ...
Community: Summertree
Timber Oaks 11431 DOLLAR LAKE DR 1, PORT RICHEY, FL,..., Port Richey, FL 34668
$160,000

2 beds

|

2 baths

|

1,372 sq ft

|

Villa

11431 DOLLAR LAKE DR 1, PORT RICHEY, FL,...
Community: Timber Oaks
Timber Oaks 11317 VERSAILLES LN # 5, PORT RICHEY, FL..., Port Richey, FL 34668
$177,900

2 beds

|

2 baths

|

1,037 sq ft

|

Condo

11317 VERSAILLES LN # 5, PORT RICHEY, FL...
Community: Timber Oaks
Timber Oaks 8141 BUGLE CT 1, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$145,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

8141 BUGLE CT 1, PORT RICHEY, FL, 34668
Community: Timber Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heritage Springs 11429 HIDDEN COVE CT, TRINITY, FL, 34655, Trinity, FL 34655
$479,000

3 beds

|

2 baths

|

1,876 sq ft

|

House

11429 HIDDEN COVE CT, TRINITY, FL, 34655
Community: Heritage Springs
Highland Lakes on Lake Tarpon 3569 OAK LAKE DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$398,000

2 beds

|

2 baths

|

1,466 sq ft

|

House

3569 OAK LAKE DR, PALM HARBOR, FL, 34684
Beacon Lakes 4028 DAVIT DR 4028, NEW PORT RICHEY, FL,..., New Port Richey, FL 34652
$150,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

4028 DAVIT DR 4028, NEW PORT RICHEY, FL,...
Community: Beacon Lakes
Timber Oaks 11604 VERSAILLES LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$200,000

2 beds

|

2 baths

|

1,239 sq ft

|

House

11604 VERSAILLES LN, PORT RICHEY, FL, 34...
Community: Timber Oaks
Pine Ridge at Palm Harbor 1725 PINE RIDGE WAY C, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$295,000

2 beds

|

2 baths

|

1,350 sq ft

|

Villa

1725 PINE RIDGE WAY C, 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.
Timber Greens 9326 PALM HAVEN CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$309,000

2 beds

|

2 baths

|

1,672 sq ft

|

Villa

9326 PALM HAVEN CT, NEW PORT RICHEY, FL,...
Community: Timber Greens
Timber Oaks 8708 BENTON DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$244,250

2 beds

|

2 baths

|

1,112 sq ft

|

House

8708 BENTON DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
Edgewater Arms 634 EDGEWATER DR 848, DUNEDIN, FL, 34698, Dunedin, FL 34698
$499,000

2 beds

|

2 baths

|

1,465 sq ft

|

Condo

634 EDGEWATER DR 848, DUNEDIN, FL, 34698
Community: Edgewater Arms
Edgewater Arms 634 EDGEWATER DR 744, DUNEDIN, FL, 34698, Dunedin, FL 34698
$1,060,000

3 beds

|

3 baths

|

2,330 sq ft

|

Condo

634 EDGEWATER DR 744, DUNEDIN, FL, 34698
Community: Edgewater Arms
Timber Oaks 11120 CARRIAGE HILL DR 1, PORT RICHEY, F..., Port Richey, FL 34668
$96,000

2 beds

|

2 baths

|

882 sq ft

|

Villa

11120 CARRIAGE HILL DR 1, PORT RICHEY, F...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 1084 DUNROBIN DR D, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$269,500

2 beds

|

2 baths

|

1,360 sq ft

|

Villa

1084 DUNROBIN DR D, PALM HARBOR, FL, 346...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Briar Patch 4523 GLEN HOLW, NEW PORT RICHEY, FL, 346..., New Port Richey, FL 34653
$189,000

2 beds

|

2 baths

|

964 sq ft

|

House

4523 GLEN HOLW, NEW PORT RICHEY, FL, 346...
Community: Briar Patch
Timber Oaks 10654 FALLEN LEAF LN, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$299,900

2 beds

|

2 baths

|

1,718 sq ft

|

House

10654 FALLEN LEAF LN, PORT RICHEY, FL, 3...
Community: Timber Oaks
Heritage Lake 9902 ST JOSEPH, NEW PORT RICHEY, FL, 346..., New Port Richey, FL 34655
$325,000

2 beds

|

2 baths

|

1,747 sq ft

|

House

9902 ST JOSEPH, NEW PORT RICHEY, FL, 346...
Community: Heritage Lake
Timber Oaks 10721 FOOTPRINT LN, PORT RICHEY, FL, 346..., Port Richey, FL 34668
$289,900

2 beds

|

2 baths

|

2,005 sq ft

|

House

10721 FOOTPRINT LN, 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.
Edgewater Arms 632 EDGEWATER DR 135, DUNEDIN, FL, 34698, Dunedin, FL 34698
$399,000

2 beds

|

2 baths

|

1,330 sq ft

|

Condo

632 EDGEWATER DR 135, DUNEDIN, FL, 34698
Community: Edgewater Arms
Edgewater Arms 634 EDGEWATER DR 849, DUNEDIN, FL, 34698, Dunedin, FL 34698
$552,000

2 beds

|

2 baths

|

1,630 sq ft

|

Condo

634 EDGEWATER DR 849, DUNEDIN, FL, 34698
Community: Edgewater Arms
Pine Ridge at Palm Harbor 2522 PINE RIDGE WAY A2, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$189,900

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

2522 PINE RIDGE WAY A2, PALM HARBOR, FL,...
Highland Lakes on Lake Tarpon 3280 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$245,000

2 beds

|

2 baths

|

1,332 sq ft

|

Villa

3280 MCMATH DR, PALM HARBOR, FL, 34684
Timber Greens 9630 GREEN NEEDLE DR, NEW PORT RICHEY, F..., New Port Richey, FL 34655
$349,900

2 beds

|

2 baths

|

1,724 sq ft

|

House

9630 GREEN NEEDLE DR, NEW PORT RICHEY, F...
Community: Timber Greens
Highland Lakes on Lake Tarpon 2137 MALCOLM DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$424,900

2 beds

|

2 baths

|

1,519 sq ft

|

House

2137 MALCOLM DR, PALM HARBOR, FL, 34684
Highland Lakes on Lake Tarpon 2842 HIGHLANDS BLVD A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$225,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

2842 HIGHLANDS BLVD A, PALM HARBOR, FL, ...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Highland Lakes on Lake Tarpon 2739 SHERBROOKE LN B, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$238,000

2 beds

|

2 baths

|

1,000 sq ft

|

Villa

2739 SHERBROOKE LN B, PALM HARBOR, FL, 3...
Timber Greens 9742 OAKWOOD HILLS CT, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$455,000

3 beds

|

2 baths

|

1,905 sq ft

|

House

9742 OAKWOOD HILLS CT, NEW PORT RICHEY, ...
Community: Timber Greens
Timber Greens 9338 CLEARMEADOW LN, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$305,000

2 beds

|

2 baths

|

1,855 sq ft

|

Villa

9338 CLEARMEADOW LN, NEW PORT RICHEY, FL...
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.
Green Dolphin 1250 S PINELLAS AVE 803, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$89,900

1 beds

|

1 baths

|

669 sq ft

|

Condo

1250 S PINELLAS AVE 803, TARPON SPRINGS,...
Community: Green Dolphin
Highland Lakes on Lake Tarpon 1350 GLENGARRY DR, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$450,000

2 beds

|

2 baths

|

1,694 sq ft

|

House

1350 GLENGARRY DR, PALM HARBOR, FL, 3468...
Timber Oaks 8350 HIGH POINT CIR 3, PORT RICHEY, FL, ..., Port Richey, FL 34668
$165,000

2 beds

|

2 baths

|

1,372 sq ft

|

Condo

8350 HIGH POINT CIR 3, PORT RICHEY, FL, ...
Community: Timber Oaks
Royal Stewart Arms 5 GATESHEAD DR 107, DUNEDIN, FL, 34698, Dunedin, FL 34698
$334,900

2 beds

|

2 baths

|

1,175 sq ft

|

Condo

5 GATESHEAD DR 107, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Timber Oaks 11508 ORLEANS LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$185,000

2 beds

|

2 baths

|

1,395 sq ft

|

Condo

11508 ORLEANS LN, PORT RICHEY, FL, 34668
Community: Timber Oaks
Heather Lake Condominiums 952 VIRGINIA ST 105, DUNEDIN, FL, 34698, Dunedin, FL 34698
$220,000

2 beds

|

2 baths

|

965 sq ft

|

Condo

952 VIRGINIA ST 105, DUNEDIN, FL, 34698
Key Vista Villas 2453 PLEASANT HILL LN, HOLIDAY, FL, 3469..., Holiday, FL 34691
$275,000

2 beds

|

2 baths

|

1,555 sq ft

|

House

2453 PLEASANT HILL LN, HOLIDAY, FL, 3469...
Community: Key Vista Villas
Timber Greens 9500 GREEN NEEDLE DR, NEW PORT RICHEY, F..., New Port Richey, FL 34655
$336,000

2 beds

|

2 baths

|

1,213 sq ft

|

House

9500 GREEN NEEDLE DR, NEW PORT RICHEY, F...
Community: Timber Greens
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Edgewater Arms 632 EDGEWATER DR 238, DUNEDIN, FL, 34698, Dunedin, FL 34698
$349,900

2 beds

|

2 baths

|

1,220 sq ft

|

Condo

632 EDGEWATER DR 238, DUNEDIN, FL, 34698
Community: Edgewater Arms
Timber Greens 6543 PINE WALK DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$309,000

2 beds

|

2 baths

|

1,380 sq ft

|

Villa

6543 PINE WALK DR, NEW PORT RICHEY, FL, ...
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.
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This application does not include information on all of the properties available for sale at this time.

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