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

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
Timber Oaks 11210 CARRIAGE HILL DR 6, PORT RICHEY, F..., Port Richey, FL 34668
$79,990

2 beds

|

2 baths

|

954 sq ft

|

Condo

11210 CARRIAGE HILL DR 6, PORT RICHEY, F...
Community: Timber Oaks
Heather Lake Condominiums 946 VIRGINIA ST 104, DUNEDIN, FL, 34698, Dunedin, FL 34698
$119,000

1 beds

|

1 baths

|

770 sq ft

|

Condo

946 VIRGINIA ST 104, DUNEDIN, FL, 34698
Summertree 11613 PEAR TREE DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$239,000

2 beds

|

2 baths

|

1,414 sq ft

|

House

11613 PEAR TREE DR, NEW PORT RICHEY, FL,...
Community: Summertree
Heritage Lake 4916 TROON LN, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34655
$235,000

2 beds

|

2 baths

|

1,309 sq ft

|

Condo

4916 TROON LN, NEW PORT RICHEY, FL, 3465...
Community: Heritage Lake
Heritage Lake 4709 PORTLAND MANOR DR, NEW PORT RICHEY,..., New Port Richey, FL 34655
$337,000

2 beds

|

2 baths

|

1,714 sq ft

|

House

4709 PORTLAND MANOR DR, NEW PORT RICHEY,...
Community: Heritage Lake
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Village on the Green 2556 ROYAL PINES CIR 13-C, CLEARWATER, F..., Clearwater, FL 33763
$210,000

2 beds

|

2 baths

|

1,030 sq ft

|

Condo

2556 ROYAL PINES CIR 13-C, CLEARWATER, F...
Timber Greens 5924 WILLOW CREEK CT, NEW PORT RICHEY, F..., New Port Richey, FL 34655
$389,000

3 beds

|

2 baths

|

1,831 sq ft

|

House

5924 WILLOW CREEK CT, NEW PORT RICHEY, F...
Community: Timber Greens
Esplanade at Starkey Ranch 11503 CALLISIA DR, ODESSA, FL, 33556, Odessa, FL 33556
$515,000

3 beds

|

2 baths

|

1,931 sq ft

|

House

11503 CALLISIA DR, ODESSA, FL, 33556
Timber Oaks 10707 SALAMANCA DR, PORT RICHEY, FL, 346..., Port Richey, FL 34668
$260,000

2 beds

|

2 baths

|

1,274 sq ft

|

House

10707 SALAMANCA DR, PORT RICHEY, FL, 346...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 133 STAFFORD CIR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$359,000

2 beds

|

2 baths

|

1,230 sq ft

|

House

133 STAFFORD CIR, 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.
Heritage Springs 1741 ARBOR KNOLL LOOP, TRINITY, FL, 3465..., Trinity, FL 34655
$379,900

3 beds

|

2 baths

|

1,793 sq ft

|

House

1741 ARBOR KNOLL LOOP, TRINITY, FL, 3465...
Community: Heritage Springs
Heritage Springs 12133 ARRON TER, TRINITY, FL, 34655, Trinity, FL 34655
$373,000

2 beds

|

2 baths

|

1,594 sq ft

|

Villa

12133 ARRON TER, TRINITY, FL, 34655
Community: Heritage Springs
Timber Oaks 11337 VERSAILLES LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$209,900

2 beds

|

2 baths

|

1,253 sq ft

|

Condo

11337 VERSAILLES LN, PORT RICHEY, FL, 34...
Community: Timber Oaks
Timber Oaks 8111 BUGLE CT 2, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$125,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

8111 BUGLE CT 2, PORT RICHEY, FL, 34668
Community: Timber Oaks
Timber Greens 10029 BROOKDALE DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$294,900

3 beds

|

2 baths

|

1,538 sq ft

|

House

10029 BROOKDALE DR, NEW PORT RICHEY, FL,...
Community: Timber Greens
Highland Lakes on Lake Tarpon 2632 CAMILLE DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$428,000

2 beds

|

2 baths

|

1,754 sq ft

|

House

2632 CAMILLE DR, PALM HARBOR, FL, 34684
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Highland Lakes on Lake Tarpon 3097 MISSION GROVE DR A, PALM HARBOR, FL..., Palm Harbor, FL 34684
$116,000

1 beds

|

1 baths

|

636 sq ft

|

Villa

3097 MISSION GROVE DR A, PALM HARBOR, FL...
Highland Lakes on Lake Tarpon 1131 ORANGE TREE CIR C, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$192,777

2 beds

|

2 baths

|

960 sq ft

|

Villa

1131 ORANGE TREE CIR C, PALM HARBOR, FL,...
Beacon Lakes 3820 LIGHTHOUSE WAY, NEW PORT RICHEY, FL..., New Port Richey, FL 34652
$129,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

3820 LIGHTHOUSE WAY, NEW PORT RICHEY, FL...
Community: Beacon Lakes
Highland Lakes on Lake Tarpon 3284 GORSE CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$309,900

2 beds

|

2 baths

|

1,148 sq ft

|

Villa

3284 GORSE CT, 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.
Heritage Lake 4876 BOONESBORO CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$169,000

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

4876 BOONESBORO CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Briar Patch 4534 SLIPPERY ROCK RD, NEW PORT RICHEY, ..., New Port Richey, FL 34653
$218,000

2 beds

|

2 baths

|

1,359 sq ft

|

Townhouse

4534 SLIPPERY ROCK RD, NEW PORT RICHEY, ...
Community: Briar Patch
Heritage Lake 9031 WARWICK LN 9031, NEW PORT RICHEY, F..., New Port Richey, FL 34655
$214,900

2 beds

|

2 baths

|

1,309 sq ft

|

Condo

9031 WARWICK LN 9031, NEW PORT RICHEY, F...
Community: Heritage Lake
Esplanade at Starkey Ranch 3254 FRANCOA DR, ODESSA, FL, 33556, Odessa, FL 33556
$510,000

3 beds

|

2 baths

|

1,931 sq ft

|

House

3254 FRANCOA DR, ODESSA, FL, 33556
Timber Greens 6646 GARDEN PALM CT, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$529,900

4 beds

|

2 baths

|

2,560 sq ft

|

House

6646 GARDEN PALM CT, NEW PORT RICHEY, FL...
Community: Timber Greens
Imperial Pines Condominiums 3062 EASTLAND BLVD 406, CLEARWATER, FL, ..., Clearwater, FL 33761
$147,000

1 beds

|

1 baths

|

920 sq ft

|

Condo

3062 EASTLAND BLVD 406, CLEARWATER, FL, ...
Royal Stewart Arms 7 ELGIN PL 508, DUNEDIN, FL, 34698, Dunedin, FL 34698
$299,900

2 beds

|

1 baths

|

970 sq ft

|

Condo

7 ELGIN PL 508, 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
Heritage Lake 9909 SAINT JOSEPH CT, NEW PORT RICHEY, F..., New Port Richey, FL 34655
$340,000

2 beds

|

2 baths

|

2,068 sq ft

|

House

9909 SAINT JOSEPH CT, NEW PORT RICHEY, F...
Community: Heritage Lake
Timber Oaks 11340 CARRIAGE HILL DR 4, PORT RICHEY, F..., Port Richey, FL 34668
$109,900

2 beds

|

2 baths

|

978 sq ft

|

Condo

11340 CARRIAGE HILL DR 4, PORT RICHEY, F...
Community: Timber Oaks
Cindy Certified
1535 PINEHURST RD, DUNEDIN, FL, 34698, Dunedin, FL 34698
$539,900

3 beds

|

2 baths

|

1,520 sq ft

|

House

1535 PINEHURST RD, 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.
Pine Ridge at Palm Harbor 2655 PINE RIDGE WAY D3, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$199,000

2 beds

|

2 baths

|

979 sq ft

|

Condo

2655 PINE RIDGE WAY D3, PALM HARBOR, FL,...
Timber Greens 6525 PINE WALK DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$289,900

2 beds

|

2 baths

|

1,549 sq ft

|

Villa

6525 PINE WALK DR, NEW PORT RICHEY, FL, ...
Community: Timber Greens
Royal Stewart Arms 2 CAUSEWAY BLVD 102, DUNEDIN, FL, 34698, Dunedin, FL 34698
$189,000

1 beds

|

1 baths

|

606 sq ft

|

Condo

2 CAUSEWAY BLVD 102, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Highland Lakes on Lake Tarpon 1009 QUEEN ANNE DR B, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$189,000

2 beds

|

2 baths

|

1,000 sq ft

|

Villa

1009 QUEEN ANNE DR B, PALM HARBOR, FL, 3...
Highland Lakes on Lake Tarpon 1608 WHITEBRIDGE DR B, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$212,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1608 WHITEBRIDGE DR B, PALM HARBOR, FL, ...
Summertree 12200 PUTTER GREEN CT, NEW PORT RICHEY, ..., New Port Richey, FL 34654
$269,000

3 beds

|

2 baths

|

1,719 sq ft

|

Villa

12200 PUTTER GREEN CT, NEW PORT RICHEY, ...
Community: Summertree
Anchorage 2211 PORTSIDE PSGE, PALM HARBOR, FL, 346..., Palm Harbor, FL 34685
$409,000

2 beds

|

2 baths

|

1,778 sq ft

|

House

2211 PORTSIDE PSGE, PALM HARBOR, FL, 346...
Community: Anchorage
Highland Lakes on Lake Tarpon 3259 HILARY CIR 1C, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$325,000

2 beds

|

2 baths

|

1,330 sq ft

|

Villa

3259 HILARY CIR 1C, PALM HARBOR, FL, 346...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Edgewater Arms 622 EDGEWATER DR 823, DUNEDIN, FL, 34698, Dunedin, FL 34698
$725,000

3 beds

|

2 baths

|

2,030 sq ft

|

Condo

622 EDGEWATER DR 823, DUNEDIN, FL, 34698
Community: Edgewater Arms
Cindy Certified
3915 GAINER SPRINGS AVE, NEW PORT RICHEY..., New Port Richey, FL 34653
$319,900

3 beds

|

2 baths

|

1,451 sq ft

|

House

3915 GAINER SPRINGS AVE, NEW PORT RICHEY...
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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