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Holiday, FL 55+ active adult communities & homes for sale - Page 3

Living in Holiday

Holiday is a community located along the Gulf coast of Florida, in the Tampa metropolitan area. Surrounded by beaches and boardwalks, Holiday has a tropical atmosphere.…

Holiday is a community located along the Gulf coast of Florida, in the Tampa metropolitan area. Surrounded by beaches and boardwalks, Holiday has a tropical atmosphere. Additionally, the cost of living in Holiday is affordable and the weather throughout the year is pleasant. The weather, cost of living and beautiful scenery all combine to make Holiday 55+ communities popular with homebuyers.

Climate & Geography

The climate in Florida is generally characterized as humid subtropical. Summer temperatures in Holiday may reach temperatures in the high 80s and low 90s while winter temperatures may fall to the low 50s. Holiday gets heavy rains accumulating 51 inches of rain on average, per year.

Recreation, Culture & Entertainment

Some of the top attractions in Holiday include Anclote River Park, Key Vista Nature Park, Anclote Gulf Park, Absolute Florida Flats Fishing, Bottoms Up Fishing Excursions, Seal in the Sun Charters, Captain Dustin Fishing Charters, and Anclote Village Marina.

Residents enjoy miles of tropical beaches along the coast, and can drive to the city of Tampa in less than an hour to enjoy all of the big city amenities on offer there.

Cost of Living & Taxes

The cost of living in Holiday is notably lower than the state and national averages. Housing costs are very low and other factors like health care, grocery, utilities, and transportation are similar to the national averages.

Florida does not have a state income tax, therefore retirement income does not get additional state tax. Furthermore, qualifying residents over the age of 65 may request a homestead exemption to offset the cost of property taxes. The tax friendly regulations and lower cost of living are helpful to Holiday 55+ community residents on a budget.

Health Care

Although there are no hospitals in Holiday, there are a number of health care providers in the surrounding area that are rated high performing by U.S. News. The Medical Center of Trinity in Trinity and AdventHealth North Pinellas in Lake Tarpon are both less than 10 miles away. Other high performing hospitals close to Holiday include Mease Countryside Hospital, Regional Medical Center Bayonet Point, Morton Plant hospital, and Largo Medical Center.

Frequently Asked Questions


297 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
4.7 rating (13 reviews) Heritage Springs
$200ks - $500ks
Heritage Springs, Trinity, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,337 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
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
2 rating (1 reviews) Beacon Lakes
$100ks
Beacon Lakes, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 210 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
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.
Esplanade at Starkey Ranc...
$300ks - $700ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only | Age-targeted | Built 2016 - 2022 | 517 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
Edgewater Arms
$400ks - $600ks
Edgewater Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 homes
Victoria Lakes
$800ks - $1Ms
Victoria Lakes, Odessa, FL
New Construction | Age-targeted | Built 2025 - present | 166 homes
Green Dolphin
$100ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
Briar Patch
$100ks
Briar Patch, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 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
Imperial Pines Condominiu...
$100ks - $200ks
Imperial Pines Condominiu..., Clearwater, FL
Resale Only | 55+ age-restricted | Built 1985 - 1985 | 181 homes
Key Vista Villas
$300ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 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.
Anchorage
$200ks - $300ks
Anchorage, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 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
Heather Ridge
$100ks - $200ks
Heather Ridge, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 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
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
Highland Lakes on Lake Tarpon 2336 MALCOLM DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$395,000

2 beds

|

2 baths

|

1,288 sq ft

|

House

2336 MALCOLM DR, PALM HARBOR, FL, 34684
Pine Ridge at Palm Harbor 1700 PINE RIDGE WAY C1, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$139,900

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

1700 PINE RIDGE WAY C1, PALM HARBOR, FL,...
Highland Lakes on Lake Tarpon 945 MADRID DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$265,000

2 beds

|

2 baths

|

980 sq ft

|

Villa

945 MADRID DR, PALM HARBOR, FL, 34684
Timber Oaks 11121 ROLLINGWOOD DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$174,900

2 beds

|

2 baths

|

1,554 sq ft

|

House

11121 ROLLINGWOOD DR, PORT RICHEY, FL, 3...
Community: Timber Oaks
Imperial Pines Condominiums 3078 EASTLAND BLVD 209, CLEARWATER, FL, ..., Clearwater, FL 33761
$225,000

2 beds

|

2 baths

|

1,390 sq ft

|

Condo

3078 EASTLAND BLVD 209, CLEARWATER, FL, ...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 11541 SAN REMO CT, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$199,900

2 beds

|

2 baths

|

1,085 sq ft

|

Condo

11541 SAN REMO CT, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Cindy Certified
10667 STEINAHATCHEE LN, NEW PORT RICHEY,..., New Port Richey, FL 34655
$603,685

4 beds

|

3 baths

|

2,071 sq ft

|

House

10667 STEINAHATCHEE LN, NEW PORT RICHEY,...
Highland Lakes on Lake Tarpon 1652 HIGHLAND CLUB LN, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$215,000

1 beds

|

2 baths

|

700 sq ft

|

Villa

1652 HIGHLAND CLUB LN, PALM HARBOR, FL, ...
Timber Oaks 8521 CEDARVIEW CT, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$260,000

2 beds

|

2 baths

|

1,472 sq ft

|

House

8521 CEDARVIEW CT, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 1630 BYRNEDALE CT, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$429,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

1630 BYRNEDALE CT, 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.
Highland Lakes on Lake Tarpon 1609 WHITEBRIDGE DR A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$142,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1609 WHITEBRIDGE DR A, PALM HARBOR, FL, ...
Timber Greens 9423 SUMMERBREEZE TER, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$334,900

2 beds

|

2 baths

|

1,808 sq ft

|

House

9423 SUMMERBREEZE TER, NEW PORT RICHEY, ...
Community: Timber Greens
Pinehurst Village 1701 PINEHURST RD 2F, DUNEDIN, FL, 34698, Dunedin, FL 34698
$101,000

1 beds

|

1 baths

|

645 sq ft

|

Condo

1701 PINEHURST RD 2F, DUNEDIN, FL, 34698
Community: Pinehurst Village
Village on the Green 2529 OAKLEAF LN 30C, CLEARWATER, FL, 337..., Clearwater, FL 33763
$220,000

2 beds

|

2 baths

|

960 sq ft

|

Villa

2529 OAKLEAF LN 30C, CLEARWATER, FL, 337...
Summertree 11510 PAMPAS DR, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34654
$224,900

2 beds

|

2 baths

|

1,384 sq ft

|

House

11510 PAMPAS DR, NEW PORT RICHEY, FL, 34...
Community: Summertree
Highland Lakes on Lake Tarpon 3300 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$299,900

2 beds

|

2 baths

|

1,332 sq ft

|

Villa

3300 MCMATH DR, PALM HARBOR, FL, 34684
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 8045 PASADENA DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$177,000

2 beds

|

2 baths

|

1,422 sq ft

|

House

8045 PASADENA DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
Heritage Lake 4911 CATHEDRAL CT, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$209,900

2 beds

|

2 baths

|

1,266 sq ft

|

Condo

4911 CATHEDRAL CT, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
Timber Oaks 8643 GOLD PINE DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$259,990

2 beds

|

2 baths

|

1,470 sq ft

|

House

8643 GOLD PINE DR, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Timber Oaks 10811 PEPPERTREE LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$230,000

2 beds

|

2 baths

|

1,470 sq ft

|

House

10811 PEPPERTREE 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.
Timber Greens 6513 CARDINAL CREST DR, NEW PORT RICHEY,..., New Port Richey, FL 34655
$340,000

3 beds

|

2 baths

|

2,015 sq ft

|

House

6513 CARDINAL CREST DR, NEW PORT RICHEY,...
Community: Timber Greens
Beacon Lakes 4034 DAVIT DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34652
$149,999

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

4034 DAVIT DR, NEW PORT RICHEY, FL, 3465...
Community: Beacon Lakes
Cindy Certified
3123 MELA CT, HOLIDAY, FL, 34691, Holiday, FL 34691
$370,000

3 beds

|

2 baths

|

1,489 sq ft

|

House

3123 MELA CT, HOLIDAY, FL, 34691
Highland Lakes on Lake Tarpon 2360 SHELLY DR B, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$200,999

2 beds

|

2 baths

|

918 sq ft

|

Condo

2360 SHELLY DR B, PALM HARBOR, FL, 34684
Highland Lakes on Lake Tarpon 3370 STONEHAVEN CT B, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$229,900

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

3370 STONEHAVEN CT B, PALM HARBOR, FL, 3...
Village on the Green 2531 ROYAL PINES CIR 23E, CLEARWATER, FL..., Clearwater, FL 33763
$159,000

2 beds

|

2 baths

|

1,095 sq ft

|

Condo

2531 ROYAL PINES CIR 23E, CLEARWATER, FL...
Timber Oaks 11404 STANSBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$229,900

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
Scotsdale Cluster Condominiums 1245 SUTHERLAND CT 1452, DUNEDIN, FL, 34..., Dunedin, FL 34698
$340,000

2 beds

|

2 baths

|

1,110 sq ft

|

Condo

1245 SUTHERLAND CT 1452, DUNEDIN, FL, 34...
Timber Greens 6639 SUN POINT CT, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$335,000

2 beds

|

2 baths

|

1,824 sq ft

|

House

6639 SUN POINT CT, NEW PORT RICHEY, FL, ...
Community: Timber Greens
Highland Lakes on Lake Tarpon 2150 SHELLY DR B, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$200,000

2 beds

|

2 baths

|

918 sq ft

|

Condo

2150 SHELLY DR B, PALM HARBOR, FL, 34684
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 3217 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$324,900

2 beds

|

2 baths

|

1,332 sq ft

|

Villa

3217 MCMATH DR, PALM HARBOR, FL, 34684
Pinehurst Village 1701 PINEHURST RD 16G, DUNEDIN, FL, 3469..., Dunedin, FL 34698
$162,900

2 beds

|

1 baths

|

875 sq ft

|

Villa

1701 PINEHURST RD 16G, DUNEDIN, FL, 3469...
Community: Pinehurst Village
Village on the Green 2506 OAKLEAF LN 25B, CLEARWATER, FL, 337..., Clearwater, FL 33763
$214,900

2 beds

|

2 baths

|

960 sq ft

|

Villa

2506 OAKLEAF LN 25B, CLEARWATER, FL, 337...
Timber Oaks 11130 CARRIAGE HILL DR 6, PORT RICHEY, F..., Port Richey, FL 34668
$105,000

2 beds

|

2 baths

|

954 sq ft

|

Condo

11130 CARRIAGE HILL DR 6, PORT RICHEY, F...
Community: Timber Oaks
Heritage Lake 9902 SAINT JOSEPH CT, NEW PORT RICHEY, F..., New Port Richey, FL 34655
$317,500

2 beds

|

2 baths

|

1,747 sq ft

|

House

9902 SAINT JOSEPH CT, NEW PORT RICHEY, F...
Community: Heritage Lake
Patrician Oaks 870 VIRGINIA ST 104, DUNEDIN, FL, 34698, Dunedin, FL 34698
$109,500

1 beds

|

1 baths

|

793 sq ft

|

Condo

870 VIRGINIA ST 104, DUNEDIN, FL, 34698
Community: Patrician Oaks
Timber Oaks 10624 ENCINO CT, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$250,000

2 beds

|

2 baths

|

1,467 sq ft

|

House

10624 ENCINO CT, PORT RICHEY, FL, 34668
Community: Timber Oaks
Highland Lakes on Lake Tarpon 2833 ORANGE TREE CIR A, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$189,500

2 beds

|

2 baths

|

960 sq ft

|

Villa

2833 ORANGE TREE CIR A, PALM HARBOR, FL,...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heritage Springs 1236 FLORA VISTA ST, TRINITY, FL, 34655, Trinity, FL 34655
$450,000

2 beds

|

2 baths

|

1,903 sq ft

|

Villa

1236 FLORA VISTA ST, TRINITY, FL, 34655
Community: Heritage Springs
Heritage Lake 4706 WALLINGFORD CT 68, NEW PORT RICHEY,..., New Port Richey, FL 34655
$260,000

2 beds

|

2 baths

|

1,340 sq ft

|

Condo

4706 WALLINGFORD CT 68, NEW PORT RICHEY,...
Community: Heritage Lake
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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