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...

<$100k - $500Ks

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 - $300Ks

Timber Oaks, Port Richey, FL

Resale Only | 55+ age-restricted | Built 1973 - 1997 | 1,000 homes

Heritage Lake

$100Ks - $300Ks

Heritage Lake, New Port Richey, FL

Resale Only | 55+ age-restricted | Built 1981 - 1994 | 932 homes

Summertree

$100Ks - $300Ks

Summertree, New Port Richey, FL

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

Green Dolphin

<$100k - $200Ks

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

$200Ks - $400Ks

Royal Stewart Arms, Dunedin, FL

Resale Only | 55+ age-restricted | Built 1968 - 1975 | 449 homes

Heather Lake Condominiums

$100Ks - $200Ks

Heather Lake Condominiums, Dunedin, FL

Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 homes

3.5 rating (2 reviews)

Timber Greens

$200Ks - $400Ks

Timber Greens, New Port Richey, FL

Resale Only | 55+ age-restricted | Built 1994 - 2004 | 783 homes

Edgewater Arms

$400Ks - $1Ms

Edgewater Arms, Dunedin, FL

Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 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 - $200Ks

Briar Patch, New Port Richey, FL

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

4.7 rating (13 reviews)

Heritage Springs

$300Ks - $400Ks

Heritage Springs, Trinity, FL

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

5 rating (1 reviews)

Pine Ridge at Palm Harbor

$100Ks

Pine Ridge at Palm Harbor, Palm Harbor, FL

Resale Only | 55+ age-restricted | Built 1983 - 1983 | 264 homes

Pinehurst Village

$100Ks - $200Ks

Pinehurst Village, Dunedin, FL

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

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

Questions? Call us: (727) 800-3371

Imperial Pines Condominiu...

$100Ks - $200Ks

Imperial Pines Condominiu..., Clearwater, FL

Resale Only | 55+ age-restricted | Built 1985 - 1985 | 181 homes

Esplanade at Starkey Ranc...

$600Ks - $900Ks

Esplanade at Starkey Ranc..., Odessa, FL

Resale Only | Age-targeted | Built 2016 - 2022 | 517 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

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 Ridge

$100Ks

Heather Ridge, Dunedin, FL

Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 homes

Key Vista Villas

$200Ks - $300Ks

Key Vista Villas, Holiday, FL

Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 homes

Patrician Oaks

$100Ks

Patrician Oaks, Dunedin, FL

Resale Only | 55+ age-restricted | Built 1975 - 1982 | 120 homes

Linkside Village

$100Ks

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

Anchorage

$300Ks - $400Ks

Anchorage, Palm Harbor, FL

Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 homes

Heather Hills Villas

<$100k

Heather Hills Villas, Dunedin, FL

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

Scotsdale Cluster Condomi...

$300Ks

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

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

Questions? Call us: (727) 800-3371

New Port Corners

$200Ks - $500Ks

New Port Corners, New Port Richey, FL

880 MACLAREN DR B, PALM HARBOR, FL, 3468...

Community: Highland Lakes on Lake Tarpon

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 Timber Oaks

8708 BENTON DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668

$254,999

2 beds

2 baths

1,112 sq ft

House

8708 BENTON DR, PORT RICHEY, FL, 34668

Community: Timber Oaks

New Green Dolphin

1938 GOLFVIEW DR # 1938, TARPON SPRINGS,..., Tarpon Springs, FL 34689

$199,900

2 beds

2 baths

1,125 sq ft

Condo

1938 GOLFVIEW DR # 1938, TARPON SPRINGS,...

Community: Green Dolphin

New Scotsdale Cluster Condominiums

409 STIRLING TER, DUNEDIN, FL, 34698, Dunedin, FL 34698

$369,900

2 beds

2 baths

1,110 sq ft

Villa

409 STIRLING TER, DUNEDIN, FL, 34698

Community: Scotsdale Cluster Condominiums

New Edgewater Arms

634 EDGEWATER DR 848, DUNEDIN, FL, 34698, Dunedin, FL 34698

$550,000

2 beds

2 baths

1,465 sq ft

Condo

634 EDGEWATER DR 848, DUNEDIN, FL, 34698

Community: Edgewater Arms

New Edgewater Arms

634 EDGEWATER DR 744, DUNEDIN, FL, 34698, Dunedin, FL 34698

$1,090,000

3 beds

3 baths

2,330 sq ft

Condo

634 EDGEWATER DR 744, DUNEDIN, FL, 34698

Community: Edgewater Arms

New Heritage Springs

1326 WINDING WILLOW DR, TRINITY, FL, 346..., Trinity, FL 34655

$460,000

3 beds

2 baths

1,684 sq ft

House

1326 WINDING WILLOW DR, TRINITY, FL, 346...

Community: Heritage Springs

New Timber Oaks

8014 CASUARINA DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668

$258,000

3 beds

3 baths

1,650 sq ft

House

8014 CASUARINA DR, PORT RICHEY, FL, 3466...

Community: Timber Oaks

New Timber Oaks

11120 CARRIAGE HILL DR 1, PORT RICHEY, F..., Port Richey, FL 34668

$105,000

2 beds

2 baths

882 sq ft

Villa

11120 CARRIAGE HILL DR 1, PORT RICHEY, F...

Community: Timber Oaks

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

Questions? Call us: (727) 800-3371

New Pinehurst Village

1701 PINEHURST RD APT 9G, DUNEDIN, FL, 3..., Dunedin, FL 34698

$199,000

2 beds

2 baths

875 sq ft

Condo

1701 PINEHURST RD APT 9G, DUNEDIN, FL, 3...

Community: Pinehurst Village

New Highland Lakes on Lake Tarpon

3535 BIRKDALE LN, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$525,000

2 beds

2 baths

1,765 sq ft

Villa

3535 BIRKDALE LN, PALM HARBOR, FL, 34684

House

1248 ASHBOURNE CIR, TRINITY, FL, 34655

House

1563 WICKLOW DR, PALM HARBOR, FL, 34684

Condo

2238 LARK CIR D, PALM HARBOR, FL, 34684

House

1211 ALMONDWOOD DR, TRINITY, FL, 34655

House

3280 SKENE TER, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

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

Questions? Call us: (727) 800-3371

Heather Lake Condominiums

920 VIRGINIA ST APT 302, DUNEDIN, FL, 34..., Dunedin, FL 34698

$146,000

2 beds

1 baths

935 sq ft

Condo

920 VIRGINIA ST APT 302, DUNEDIN, FL, 34...

Community: Heather Lake Condominiums

Pine Ridge at Palm Harbor

2522 PINE RIDGE WAY A2, PALM HARBOR, FL,..., Palm Harbor, FL 34684

$199,900

2 beds

2 baths

1,038 sq ft

Condo

2522 PINE RIDGE WAY A2, PALM HARBOR, FL,...

Community: Pine Ridge at Palm Harbor

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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26 communities

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The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
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REIN updates its listings on a daily basis. Data last updated: Feb 01, 2026.
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Holiday, FL 55+ active adult communities & homes for sale

26 communities near Holiday

304 homes near Holiday

2 beds

2 baths

1,672 sq ft

Villa

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,210 sq ft

Condo

2 beds

2 baths

1,340 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,112 sq ft

House

2 beds

2 baths

1,125 sq ft

Condo

2 beds

2 baths

1,110 sq ft

Villa

2 beds

2 baths

1,465 sq ft

Condo

3 beds

3 baths

2,330 sq ft

Condo

3 beds

2 baths

1,684 sq ft

House

3 beds

3 baths

1,650 sq ft

House

2 beds

2 baths

882 sq ft

Villa

2 beds

2 baths

875 sq ft

Condo

2 beds

2 baths

1,765 sq ft

Villa

2 beds

2 baths

965 sq ft

Condo

3 beds

2 baths

1,806 sq ft

House

2 beds

2 baths

1,230 sq ft

Villa

2 beds

2 baths

964 sq ft

House

2 beds