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

26 communities 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

Summertree

$200ks - $300ks

Summertree, New Port Richey, FL

Resale Only | 55+ age-restricted | Built 1974 - 2015 | 800 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

Want to learn more about 55+ rental communities in Holiday? 55places can help!

Questions? Call us: (727) 800-3371

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

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

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.

4.7 rating (13 reviews)

Heritage Springs

$200ks - $500ks

Heritage Springs, Trinity, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,337 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

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

Pinehurst Village

$100ks

Pinehurst Village, Dunedin, FL

Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 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

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

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+ rental communities in Holiday? 55places can help!

Questions? Call us: (727) 800-3371

2 rating (1 reviews)

Beacon Lakes

$100ks

Beacon Lakes, New Port Richey, FL

Resale Only | 55+ age-restricted | Built 1975 - 1982 | 210 homes

Briar Patch

$100ks

Briar Patch, New Port Richey, FL

Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 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

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

Want to learn more about 55+ communities in Holiday? 55places can help!

Questions? Call us: (727) 800-3371

Heather Hills Villas

$100ks

Heather Hills Villas, Dunedin, FL

Resale Only | 55+ age-restricted | Built 1971 - 1976 | 64 homes

Scotsdale Cluster Condomi...

$200ks

Scotsdale Cluster Condomi..., Dunedin, FL

Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 homes

Country Oaks

$100ks

Country Oaks, Hudson, FL

Resale Only | 55+ age-restricted | Built 1981 - 1986 | 42 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+ rental communities in Holiday? 55places can help!

Questions? Call us: (727) 800-3371

Linkside Village

$200ks

Linkside Village, Port Richey, FL

1237 RAMBLING VINE CT, TRINITY, FL, 3465...

Community: Heritage Springs

Want to learn more about 55+ communities in Holiday? 55places can help!

Questions? Call us: (727) 800-3371

Want to learn more about 55+ rental communities in Holiday? 55places can help!

Questions? Call us: (727) 800-3371

New Imperial Pines Condominiums

3078 EASTLAND BLVD 411, CLEARWATER, FL, ..., Clearwater, FL 33761

$179,900

1 beds

1 baths

870 sq ft

Condo

3078 EASTLAND BLVD 411, CLEARWATER, FL, ...

Community: Imperial Pines Condominiums

New Timber Oaks

11210 CARRIAGE HILL DR APT 2, PORT RICHE..., Port Richey, FL 34668

$129,900

2 beds

2 baths

954 sq ft

Condo

11210 CARRIAGE HILL DR APT 2, PORT RICHE...

Community: Timber Oaks

New Heather Lake Condominiums

920 VIRGINIA ST APT 303, DUNEDIN, FL, 34..., Dunedin, FL 34698

$164,900

2 beds

1 baths

935 sq ft

Condo

920 VIRGINIA ST APT 303, DUNEDIN, FL, 34...

Community: Heather Lake Condominiums

New Edgewater Arms

632 EDGEWATER DR UNIT 139, DUNEDIN, FL, ..., Dunedin, FL 34698

$359,900

2 beds

2 baths

1,330 sq ft

Condo

632 EDGEWATER DR UNIT 139, DUNEDIN, FL, ...

Community: Edgewater Arms

New Village on the Green

2573 OAKLEAF LN 39A, CLEARWATER, FL, 337..., Clearwater, FL 33763

$229,900

2 beds

2 baths

940 sq ft

Villa

2573 OAKLEAF LN 39A, CLEARWATER, FL, 337...

Community: Village on the Green

New Highland Lakes on Lake Tarpon

1303 GLENGARRY DR, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684

$454,900

2 beds

2 baths

1,687 sq ft

House

1303 GLENGARRY DR, PALM HARBOR, FL, 3468...

Community: Highland Lakes on Lake Tarpon

Timber Oaks

11117 PEMBRIDGE CT 2, PORT RICHEY, FL, 3..., Port Richey, FL 34668

$114,000

2 beds

1 baths

882 sq ft

Condo

11117 PEMBRIDGE CT 2, PORT RICHEY, FL, 3...

Community: Timber Oaks

Heritage Lake

4736 PORTLAND MANOR DR, NEW PORT RICHEY,..., New Port Richey, FL 34655

$325,000

2 beds

2 baths

1,756 sq ft

House

4736 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

Highland Lakes on Lake Tarpon

102 STAFFORD DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$379,900

2 beds

2 baths

1,264 sq ft

House

102 STAFFORD DR, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

Summertree

11829 IVYWOOD PL, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34654

$259,000

3 beds

2 baths

1,632 sq ft

House

11829 IVYWOOD PL, NEW PORT RICHEY, FL, 3...

Condo

8131 BRADDOCK CIR 1, 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

Anchorage

2108 PORTSIDE PSGE, PALM HARBOR, FL, 346..., Palm Harbor, FL 34685

$399,900

2 beds

2 baths

1,525 sq ft

House

2108 PORTSIDE PSGE, PALM HARBOR, FL, 346...

Community: Anchorage

Heritage Springs

1031 ALMONDWOOD DR, TRINITY, FL, 34655, Trinity, FL 34655

$345,000

2 beds

2 baths

1,450 sq ft

Villa

1031 ALMONDWOOD DR, TRINITY, FL, 34655

Community: Heritage Springs

Patrician Oaks

865 VIRGINIA CT APT 107, DUNEDIN, FL, 34..., Dunedin, FL 34698

$110,000

1 beds

1 baths

817 sq ft

Condo

865 VIRGINIA CT APT 107, DUNEDIN, FL, 34...

Community: Patrician Oaks

Royal Stewart Arms

9 HAIG PL 612, DUNEDIN, FL, 34698, Dunedin, FL 34698

$299,000

2 beds

2 baths

1,181 sq ft

Condo

9 HAIG PL 612, DUNEDIN, FL, 34698

Condo

1339 QUEEN ANNE DR C, PALM HARBOR, FL, 3...

Villa

865 MACLAREN DR A, PALM HARBOR, FL, 3468...

Community: Highland Lakes on Lake Tarpon

Want to learn more about 55+ rental communities in Holiday? 55places can help!

Questions? Call us: (727) 800-3371

Edgewater Arms

632 EDGEWATER DR 437, DUNEDIN, FL, 34698, Dunedin, FL 34698

$249,000

1 beds

1 baths

695 sq ft

Condo

632 EDGEWATER DR 437, DUNEDIN, FL, 34698

Community: Edgewater Arms

Timber Oaks

11541 ORLEANS LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668

$184,000

2 beds

2 baths

1,152 sq ft

Townhouse

11541 ORLEANS LN, PORT RICHEY, FL, 34668

Community: Timber Oaks

Anchorage

811 HELMSMAN WAY, PALM HARBOR, FL, 34685, Palm Harbor, FL 34685

$365,000

2 beds

2 baths

1,666 sq ft

House

811 HELMSMAN WAY, PALM HARBOR, FL, 34685

Community: Anchorage

Want to learn more about 55+ communities in Holiday? 55places can help!

Questions? Call us: (727) 800-3371

Timber Oaks

11431 DOLLAR LAKE DR 1, PORT RICHEY, FL,..., Port Richey, FL 34668

$225,000

2 beds

2 baths

1,372 sq ft

Villa

11431 DOLLAR LAKE DR 1, PORT RICHEY, FL,...

Community: Timber Oaks

Timber Oaks

11337 VERSAILLES LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668

$234,000

2 beds

2 baths

1,253 sq ft

Condo

11337 VERSAILLES LN, PORT RICHEY, FL, 34...

Community: Timber Oaks

Frequently Asked Questions

What size 55+ communities are there in Holiday?

In Holiday, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Holiday?

The smallest 55+ community in Holiday has 170 homes, the largest has 170 homes, and the average community consists of 170 homes.

Are there gated 55+ communities in Holiday?

Yes, there is gated 55+ community in Holiday. The only 55+ community in Holiday is gated. For instance, Key Vista Villas is a gated community with 170 homes.

How long do listings in 55+ communities in Holiday typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ community in Holiday stay on the market for around 173 days. The average price of homes for sale in this community is approximately $350,110, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Key Vista Villas average around $350,110.

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Want to learn more about 55+ communities in Holiday?

Call us: (727) 800-3371

26 communities

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REIN updates its listings on a daily basis. Data last updated: Feb 25, 2026.
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Holiday, FL 55+ active adult communities & homes for sale

26 communities near Holiday

306 homes near Holiday

2 beds

2 baths

975 sq ft

Condo

2 beds

2 baths

1,069 sq ft

House

3 beds

2 baths

1,554 sq ft

House

2 beds

2 baths

1,224 sq ft

Villa

3 beds

2 baths

2,409 sq ft

House

1 beds

1 baths

870 sq ft

Condo

2 beds

2 baths

954 sq ft

Condo

2 beds

1 baths

935 sq ft

Condo

2 beds

2 baths

1,330 sq ft

Condo

2 beds

2 baths

940 sq ft

Villa

2 beds

2 baths

1,687 sq ft

House

2 beds

1 baths

882 sq ft

Condo

2 beds

2 baths

1,756 sq ft

House

2 beds

2 baths

1,264 sq ft

House

3 beds

2 baths

1,632 sq ft

House

2 beds

2 baths

1,110 sq ft

Condo

3 beds

2 baths

1,656 sq ft

House

3 beds

2 baths

1,834 sq ft

Villa

2 beds

2 baths

1,689 sq ft

House

2 beds