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Holiday, FL 55+ active adult communities & homes for sale - Page 4

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
Cindy Certified
10762 APALACHICOLA DR, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$749,990

3 beds

|

3 baths

|

2,859 sq ft

|

House

10762 APALACHICOLA DR, NEW PORT RICHEY, ...
Village on the Green 2218 BAY BERRY LN, CLEARWATER, FL, 33763, Clearwater, FL 33763
$345,000

2 beds

|

2 baths

|

1,309 sq ft

|

House

2218 BAY BERRY LN, CLEARWATER, FL, 33763
Highland Lakes on Lake Tarpon 3253 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$369,900

2 beds

|

2 baths

|

1,332 sq ft

|

Villa

3253 MCMATH DR, PALM HARBOR, FL, 34684
Highland Lakes on Lake Tarpon 1207 TIMBERBROOKE DR, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$654,999

3 beds

|

3 baths

|

2,018 sq ft

|

House

1207 TIMBERBROOKE DR, PALM HARBOR, FL, 3...
Esplanade at Starkey Ranch 3456 FORSYTHIA DR, ODESSA, FL, 33556, Odessa, FL 33556
$949,000

3 beds

|

3 baths

|

3,054 sq ft

|

House

3456 FORSYTHIA DR, ODESSA, FL, 33556
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 11414 STANSBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$230,000

2 beds

|

2 baths

|

1,387 sq ft

|

Villa

11414 STANSBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Timber Oaks 11210 ELDERBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$258,000

2 beds

|

2 baths

|

1,158 sq ft

|

House

11210 ELDERBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Country Oaks 7719 COSME DR 1, HUDSON, FL, 34667, Hudson, FL 34667
$159,000

2 beds

|

2 baths

|

1,332 sq ft

|

Condo

7719 COSME DR 1, HUDSON, FL, 34667
Community: Country Oaks
Scotsdale Cluster Condominiums 1372 CARLISLE CT, DUNEDIN, FL, 34698, Dunedin, FL 34698
$460,000

2 beds

|

2 baths

|

1,110 sq ft

|

Villa

1372 CARLISLE CT, DUNEDIN, FL, 34698
Timber Oaks 8423 PEBBLE DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$215,500

2 beds

|

2 baths

|

1,646 sq ft

|

House

8423 PEBBLE DR, PORT RICHEY, FL, 34668
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.
Linkside Village 8423 PEBBLE DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$215,500

2 beds

|

2 baths

|

1,646 sq ft

|

House

8423 PEBBLE DR, PORT RICHEY, FL, 34668
Community: Linkside Village
Cindy Certified
502 BELTREES ST, DUNEDIN, FL, 34698, Dunedin, FL 34698
$1,100,000

3 beds

|

2 baths

|

1,804 sq ft

|

House

502 BELTREES ST, DUNEDIN, FL, 34698
Beacon Lakes 3843 LIGHTHOUSE WAY, NEW PORT RICHEY, FL..., New Port Richey, FL 34652
$150,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

3843 LIGHTHOUSE WAY, NEW PORT RICHEY, FL...
Community: Beacon Lakes
Timber Oaks 11436 VERSAILLES LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$179,000

2 beds

|

2 baths

|

1,353 sq ft

|

Condo

11436 VERSAILLES LN, PORT RICHEY, FL, 34...
Community: Timber Oaks
Green Dolphin 1250 S PINELLAS AVE 511, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$68,000

1 beds

|

1 baths

|

565 sq ft

|

Condo

1250 S PINELLAS AVE 511, TARPON SPRINGS,...
Community: Green Dolphin
Timber Oaks 10819 LOS SANTOS DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$250,000

2 beds

|

2 baths

|

1,107 sq ft

|

House

10819 LOS SANTOS 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
Heritage Springs 10924 RAIN HOLLOW CT, TRINITY, FL, 34655, Trinity, FL 34655
$439,000

3 beds

|

2 baths

|

2,582 sq ft

|

House

10924 RAIN HOLLOW CT, TRINITY, FL, 34655
Community: Heritage Springs
Heritage Lake 4739 CARRINGTON CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$185,000

2 beds

|

2 baths

|

1,261 sq ft

|

Condo

4739 CARRINGTON CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Heritage Lake 4949 BOSTONIAN LOOP, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$269,900

2 beds

|

2 baths

|

1,485 sq ft

|

Condo

4949 BOSTONIAN LOOP, NEW PORT RICHEY, FL...
Community: Heritage Lake
Timber Oaks 11140 CARRIAGE HILL DR 4, PORT RICHEY, F..., Port Richey, FL 34668
$87,500

1 beds

|

1 baths

|

714 sq ft

|

Condo

11140 CARRIAGE HILL DR 4, PORT RICHEY, F...
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.
Heritage Lake 4809 WAKEFIELD CT, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$199,999

2 beds

|

2 baths

|

1,311 sq ft

|

Villa

4809 WAKEFIELD CT, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
Timber Oaks 11512 VERSAILLES LN 11512, PORT RICHEY, ..., Port Richey, FL 34668
$180,000

2 beds

|

2 baths

|

1,237 sq ft

|

Condo

11512 VERSAILLES LN 11512, PORT RICHEY, ...
Community: Timber Oaks
Summertree 11602 WHITE ASH DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$284,900

2 beds

|

2 baths

|

1,414 sq ft

|

House

11602 WHITE ASH DR, NEW PORT RICHEY, FL,...
Community: Summertree
Summertree 11156 MERGANSER WAY, NEW PORT RICHEY, FL..., New Port Richey, FL 34654
$345,000

3 beds

|

2 baths

|

1,952 sq ft

|

House

11156 MERGANSER WAY, NEW PORT RICHEY, FL...
Community: Summertree
Heritage Springs 12021 FERN TERRACE CT, TRINITY, FL, 3465..., Trinity, FL 34655
$395,000

3 beds

|

2 baths

|

2,032 sq ft

|

House

12021 FERN TERRACE CT, TRINITY, FL, 3465...
Community: Heritage Springs
Heather Hills Villas 830 CAMBRIDGE CT, DUNEDIN, FL, 34698, Dunedin, FL 34698
$205,000

2 beds

|

2 baths

|

999 sq ft

|

Villa

830 CAMBRIDGE CT, DUNEDIN, FL, 34698
Cindy Certified
1196 MARY JANE LN, DUNEDIN, FL, 34698, Dunedin, FL 34698
$1,200,000

4 beds

|

3 baths

|

2,661 sq ft

|

House

1196 MARY JANE LN, DUNEDIN, FL, 34698
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Highland Lakes on Lake Tarpon 2958 DUNDEE DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$439,000

2 beds

|

2 baths

|

1,612 sq ft

|

House

2958 DUNDEE DR, PALM HARBOR, FL, 34684
Esplanade at Starkey Ranch 11108 CALLUNA DR, ODESSA, FL, 33556, Odessa, FL 33556
$709,000

3 beds

|

3 baths

|

2,295 sq ft

|

House

11108 CALLUNA DR, ODESSA, FL, 33556
Heather Lake Condominiums 970 VIRGINIA ST 103, DUNEDIN, FL, 34698, Dunedin, FL 34698
$83,900

1 beds

|

1 baths

|

795 sq ft

|

Condo

970 VIRGINIA ST 103, 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.
Beacon Lakes 4009 LIGHTHOUSE WAY, NEW PORT RICHEY, FL..., New Port Richey, FL 34652
$150,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

4009 LIGHTHOUSE WAY, NEW PORT RICHEY, FL...
Community: Beacon Lakes
Esplanade at Starkey Ranch 3142 FRANCOA DR, ODESSA, FL, 33556, Odessa, FL 33556
$614,000

3 beds

|

2 baths

|

1,931 sq ft

|

House

3142 FRANCOA DR, ODESSA, FL, 33556
Summertree 11404 TURTLE DOVE PL, NEW PORT RICHEY, F..., New Port Richey, FL 34654
$379,900

3 beds

|

2 baths

|

1,608 sq ft

|

House

11404 TURTLE DOVE PL, NEW PORT RICHEY, F...
Community: Summertree
Royal Stewart Arms 9 HAIG PL 101, DUNEDIN, FL, 34698, Dunedin, FL 34698
$329,000

2 beds

|

2 baths

|

1,181 sq ft

|

Condo

9 HAIG PL 101, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Green Dolphin 1250 S PINELLAS AVE 1008, TARPON SPRINGS..., Tarpon Springs, FL 34689
$139,900

2 beds

|

2 baths

|

871 sq ft

|

Condo

1250 S PINELLAS AVE 1008, TARPON SPRINGS...
Community: Green Dolphin
Highland Lakes on Lake Tarpon 2297 LARK CIR C, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$144,500

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

2297 LARK CIR C, PALM HARBOR, FL, 34684
Summertree 12154 PUTTER GREEN CT, NEW PORT RICHEY, ..., New Port Richey, FL 34654
$269,000

3 beds

|

2 baths

|

1,522 sq ft

|

Villa

12154 PUTTER GREEN CT, NEW PORT RICHEY, ...
Community: Summertree
Timber Oaks 10508 QUIMBY DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$259,900

2 beds

|

2 baths

|

1,543 sq ft

|

House

10508 QUIMBY DR, 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
Highland Lakes on Lake Tarpon 1610 BERWICK CT D, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$134,900

1 beds

|

1 baths

|

814 sq ft

|

Villa

1610 BERWICK CT D, PALM HARBOR, FL, 3468...
Heritage Lake 9136 TIARA CT, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34655
$310,000

2 beds

|

2 baths

|

1,490 sq ft

|

House

9136 TIARA CT, NEW PORT RICHEY, FL, 3465...
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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This application does not include information on all of the properties available for sale at this time.

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