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

283 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

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

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

4.7 rating (13 reviews)

Heritage Springs

$200ks - $500ks

Heritage Springs, Trinity, FL

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

Green Dolphin

$100ks

Green Dolphin, Tarpon Springs, FL

Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 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.

Edgewater Arms

$400ks - $600ks

Edgewater Arms, Dunedin, FL

Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 homes

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

Key Vista Villas

$300ks

Key Vista Villas, Holiday, FL

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

Esplanade at Starkey Ranc...

$300ks - $700ks

Esplanade at Starkey Ranc..., Odessa, FL

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

Imperial Pines Condominiu...

$100ks - $200ks

Imperial Pines Condominiu..., Clearwater, FL

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

Anchorage

$200ks - $300ks

Anchorage, Palm Harbor, FL

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

Pinehurst Village

$100ks

Pinehurst Village, Dunedin, FL

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

Heather Ridge

$100ks - $200ks

Heather Ridge, Dunedin, FL

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

2 rating (1 reviews)

Beacon Lakes

$100ks

Beacon Lakes, New Port Richey, FL

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

Patrician Oaks

$100ks

Patrician Oaks, Dunedin, FL

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

Country Oaks

$100ks

Country Oaks, Hudson, FL

Resale Only | 55+ age-restricted | Built 1981 - 1986 | 42 homes

Scotsdale Cluster Condomi...

$200ks

Scotsdale Cluster Condomi..., Dunedin, FL

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

Linkside Village

$200ks

Linkside Village, Port Richey, FL

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 100 homes

New Port Corners

$200ks - $500ks

New Port Corners, New Port Richey, FL

3462 FORSYTHIA DR, ODESSA, FL, 33556

Condo

11231 DOLLAR LAKE DR 5, PORT RICHEY, FL,...

Community: Timber Oaks

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

Questions? Call us: (727) 800-3371

New Royal Stewart Arms

9 FORBES PL 707, DUNEDIN, FL, 34698, Dunedin, FL 34698

$265,000

1 beds

1 baths

802 sq ft

Condo

9 FORBES PL 707, DUNEDIN, FL, 34698

Community: Royal Stewart Arms

New Esplanade at Starkey Ranch

11151 CALLUNA DR, ODESSA, FL, 33556, Odessa, FL 33556

$735,000

3 beds

3 baths

2,313 sq ft

House

11151 CALLUNA DR, ODESSA, FL, 33556

Community: Esplanade at Starkey Ranch

New Pine Ridge at Palm Harbor

2688 PINE RIDGE WAY D2, PALM HARBOR, FL,..., Palm Harbor, FL 34684

$183,900

2 beds

2 baths

1,038 sq ft

Condo

2688 PINE RIDGE WAY D2, PALM HARBOR, FL,...

Community: Pine Ridge at Palm Harbor

New Anchorage

760 PILOTS WAY, PALM HARBOR, FL, 34685, Palm Harbor, FL 34685

$359,999

2 beds

2 baths

1,306 sq ft

House

760 PILOTS WAY, PALM HARBOR, FL, 34685

Community: Anchorage

New Timber Oaks

8324 WINDING WOOD DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668

$278,000

2 beds

2 baths

1,490 sq ft

House

8324 WINDING WOOD DR, PORT RICHEY, FL, 3...

Community: Timber Oaks

New Patrician Oaks

870 VIRGINIA ST 111, DUNEDIN, FL, 34698, Dunedin, FL 34698

$120,000

1 beds

1 baths

664 sq ft

Condo

870 VIRGINIA ST 111, DUNEDIN, FL, 34698

Community: Patrician Oaks

New Highland Lakes on Lake Tarpon

1735 ABERDEEN CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$499,900

3 beds

2 baths

1,556 sq ft

House

1735 ABERDEEN CT, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

Heather Ridge

$115,000

2 beds

1 baths

993 sq ft

Condo

1450 HEATHER RIDGE BLVD 307, DUNEDIN, FL...

Community: Heather Ridge

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

Questions? Call us: (727) 800-3371

Esplanade at Starkey Ranch

11477 BITOLA DR, ODESSA, FL, 33556, Odessa, FL 33556

$619,000

3 beds

3 baths

2,100 sq ft

House

11477 BITOLA DR, ODESSA, FL, 33556

Community: Esplanade at Starkey Ranch

Heritage Lake

4808 VESPER CT 34, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655

$185,000

2 beds

2 baths

1,105 sq ft

Condo

4808 VESPER CT 34, NEW PORT RICHEY, FL, ...

Community: Heritage Lake

Timber Oaks

11340 DOLLAR LAKE DR 2, PORT RICHEY, FL,..., Port Richey, FL 34668

$144,900

2 beds

2 baths

1,000 sq ft

Condo

11340 DOLLAR LAKE DR 2, PORT RICHEY, FL,...

Community: Timber Oaks

Highland Lakes on Lake Tarpon

999 GILLESPIE DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$479,900

3 beds

2 baths

1,732 sq ft

House

999 GILLESPIE DR, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

Green Dolphin

1250 S PINELLAS AVE 804, TARPON SPRINGS,..., Tarpon Springs, FL 34689

$83,900

1 beds

1 baths

565 sq ft

Condo

1250 S PINELLAS AVE 804, TARPON SPRINGS,...

Community: Green Dolphin

Edgewater Arms

620 EDGEWATER DR 102, DUNEDIN, FL, 34698, Dunedin, FL 34698

$499,000

2 beds

2 baths

1,360 sq ft

Condo

620 EDGEWATER DR 102, DUNEDIN, FL, 34698

Community: Edgewater Arms

Highland Lakes on Lake Tarpon

1185 ROYAL BLVD, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$449,000

3 beds

2 baths

1,677 sq ft

House

1185 ROYAL BLVD, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

Timber Oaks

8711 GOLD PINE DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668

$275,000

3 beds

2 baths

1,610 sq ft

House

8711 GOLD PINE DR, PORT RICHEY, FL, 3466...

Community: Timber Oaks

Highland Lakes on Lake Tarpon

2938 MACALPIN DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$499,000

3 beds

2 baths

1,944 sq ft

House

2938 MACALPIN DR, PALM HARBOR, FL, 34684

Condo

1250 S PINELLAS AVE 214, TARPON SPRINGS,...

Community: Green Dolphin

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

Questions? Call us: (727) 800-3371

Heritage Springs

1249 WINDING WILLOW DR, TRINITY, FL, 346..., Trinity, FL 34655

$350,000

3 beds

2 baths

1,773 sq ft

House

1249 WINDING WILLOW DR, TRINITY, FL, 346...

Community: Heritage Springs

Summertree

11442 TURTLE DOVE PL, NEW PORT RICHEY, F..., New Port Richey, FL 34654

$289,900

2 beds

2 baths

1,471 sq ft

House

11442 TURTLE DOVE PL, NEW PORT RICHEY, F...

Community: Summertree

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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

283 homes

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REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.

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

26 communities near Holiday

283 homes near Holiday

3 beds

2 baths

1,796 sq ft

House

2 beds

2 baths

1,174 sq ft

Condo

3 beds

2 baths

1,797 sq ft

House

2 beds

2 baths

1,484 sq ft

House

3 beds

3 baths

3,095 sq ft

House

2 beds

2 baths

1,508 sq ft

House

2 beds

2 baths

1,352 sq ft

Villa

2 beds

2 baths

1,834 sq ft

House

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,555 sq ft

House

2 beds

2 baths

1,546 sq ft

Villa

2 beds

2 baths

1,341 sq ft

House

2 beds

2 baths

1,210 sq ft

Condo

1 beds

1 baths

802 sq ft

Condo

3 beds

3 baths

2,313 sq ft

House

2 beds

2 baths

1,038 sq ft

Condo

2 beds

2 baths

1,306 sq ft

House

2 beds

2 baths

1,490 sq ft

House

1 beds

1 baths

664 sq ft

Condo

3 beds