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

292 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

3.5 rating (2 reviews)

Timber Greens

$200ks - $300ks

Timber Greens, New Port Richey, FL

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

4.7 rating (13 reviews)

Heritage Springs

$200ks - $500ks

Heritage Springs, Trinity, FL

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

Heather Lake Condominiums

$100ks

Heather Lake Condominiums, Dunedin, FL

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

Green Dolphin

$100ks

Green Dolphin, Tarpon Springs, FL

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

Esplanade at Starkey Ranc...

$300ks - $700ks

Esplanade at Starkey Ranc..., Odessa, FL

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

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

2 rating (1 reviews)

Beacon Lakes

$100ks

Beacon Lakes, New Port Richey, FL

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

Briar Patch

$100ks

Briar Patch, New Port Richey, FL

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

Pinehurst Village

$100ks

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

Key Vista Villas

$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

Scotsdale Cluster Condomi...

$200ks

Scotsdale Cluster Condomi..., Dunedin, FL

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

Imperial Pines Condominiu...

$100ks - $200ks

Imperial Pines Condominiu..., Clearwater, FL

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

Heather Hills Villas

$100ks

Heather Hills Villas, Dunedin, FL

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

Anchorage

$200ks - $300ks

Anchorage, Palm Harbor, FL

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

New Port Corners

$200ks - $500ks

New Port Corners, New Port Richey, FL

New Construction | 55+ age-restricted | Built 2025 - present

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 - $200ks

Heather Ridge, Dunedin, FL

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

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

Questions? Call us: (727) 800-3371

Soleta at Starkey Ranch

$500ks - $600ks

Soleta at Starkey Ranch, Odessa, FL

6639 SUN POINT CT, NEW PORT RICHEY, FL, ...

Community: Timber Greens

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

Questions? Call us: (727) 800-3371

New Highland Lakes on Lake Tarpon

2150 SHELLY DR B, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$200,000

2 beds

2 baths

918 sq ft

Condo

2150 SHELLY DR B, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

New Highland Lakes on Lake Tarpon

3217 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$324,900

2 beds

2 baths

1,332 sq ft

Villa

3217 MCMATH DR, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

New Pinehurst Village

1701 PINEHURST RD 16G, DUNEDIN, FL, 3469..., Dunedin, FL 34698

$162,900

2 beds

1 baths

875 sq ft

Villa

1701 PINEHURST RD 16G, DUNEDIN, FL, 3469...

Community: Pinehurst Village

New Heritage Lake

4866 ENFIELD CT, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34655

$220,000

2 beds

2 baths

1,105 sq ft

House

4866 ENFIELD CT, NEW PORT RICHEY, FL, 34...

Community: Heritage Lake

New Village on the Green

2506 OAKLEAF LN 25B, CLEARWATER, FL, 337..., Clearwater, FL 33763

$234,900

2 beds

2 baths

960 sq ft

Villa

2506 OAKLEAF LN 25B, CLEARWATER, FL, 337...

Community: Village on the Green

New Timber Oaks

11130 CARRIAGE HILL DR 6, PORT RICHEY, F..., Port Richey, FL 34668

$105,000

2 beds

2 baths

954 sq ft

Condo

11130 CARRIAGE HILL DR 6, PORT RICHEY, F...

Community: Timber Oaks

New Heritage Lake

9902 SAINT JOSEPH CT, NEW PORT RICHEY, F..., New Port Richey, FL 34655

$317,500

2 beds

2 baths

1,747 sq ft

House

9902 SAINT JOSEPH CT, NEW PORT RICHEY, F...

Community: Heritage Lake

New Patrician Oaks

870 VIRGINIA ST 104, DUNEDIN, FL, 34698, Dunedin, FL 34698

$112,500

1 beds

1 baths

793 sq ft

Condo

870 VIRGINIA ST 104, DUNEDIN, FL, 34698

Community: Patrician Oaks

New Highland Lakes on Lake Tarpon

1614 BERWICK CT D, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684

$159,900

1 beds

1 baths

814 sq ft

Villa

1614 BERWICK CT D, PALM HARBOR, FL, 3468...

Community: Highland Lakes on Lake Tarpon

New Timber Oaks

10624 ENCINO CT, PORT RICHEY, FL, 34668, Port Richey, FL 34668

$250,000

2 beds

2 baths

1,467 sq ft

House

10624 ENCINO CT, PORT RICHEY, FL, 34668

Community: Timber Oaks

New Highland Lakes on Lake Tarpon

2833 ORANGE TREE CIR A, PALM HARBOR, FL,..., Palm Harbor, FL 34684

$195,000

2 beds

2 baths

960 sq ft

Villa

2833 ORANGE TREE CIR A, PALM HARBOR, FL,...

Condo

4706 WALLINGFORD CT 68, NEW PORT RICHEY,...

Community: Heritage Lake

New

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, ...

New Highland Lakes on Lake Tarpon

3253 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$374,900

2 beds

2 baths

1,332 sq ft

Villa

3253 MCMATH DR, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

Highland Lakes on Lake Tarpon

1207 TIMBERBROOKE DR, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684

$659,999

3 beds

3 baths

1,883 sq ft

House

1207 TIMBERBROOKE DR, PALM HARBOR, FL, 3...

Community: Highland Lakes on Lake Tarpon

Esplanade at Starkey Ranch

3456 FORSYTHIA DR, ODESSA, FL, 33556, Odessa, FL 33556

$986,500

3 beds

3 baths

3,054 sq ft

House

3456 FORSYTHIA DR, ODESSA, FL, 33556

Community: Esplanade at Starkey Ranch

Heritage Lake

9545 DANVILLE CT 42, NEW PORT RICHEY, FL..., New Port Richey, FL 34655

$189,500

2 beds

2 baths

1,135 sq ft

Condo

9545 DANVILLE CT 42, NEW PORT RICHEY, FL...

Community: Heritage Lake

Timber Oaks

11414 STANSBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668

$237,500

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

Highland Lakes on Lake Tarpon

3495 W LINKS CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$599,000

3 beds

2 baths

1,800 sq ft

House

3495 W LINKS CT, PALM HARBOR, FL, 34684

Condo

8423 PEBBLE DR, PORT RICHEY, FL, 34668

Community: Linkside Village

Timber Oaks

$238,000

2 beds

2 baths

1,646 sq ft

Condo

8423 PEBBLE DR, PORT RICHEY, FL, 34668

Community: Timber Oaks

Cindy Certified

502 BELTREES ST, DUNEDIN, FL, 34698, Dunedin, FL 34698

$1,150,000

1 baths

565 sq ft

Condo

1250 S PINELLAS AVE 511, TARPON SPRINGS,...

Community: Green Dolphin

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

Questions? Call us: (727) 800-3371

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

Heritage Springs

10924 RAIN HOLLOW CT, NEW PORT RICHEY, F..., New Port Richey, FL 34655

$449,000

3 beds

2 baths

2,582 sq ft

House

10924 RAIN HOLLOW CT, NEW PORT RICHEY, F...

Community: Heritage Springs

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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 346 days. The average price of homes for sale in this community is approximately $346,102, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Key Vista Villas average around $346,102.

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Want to learn more about 55+ communities in Holiday?

Call us: (727) 800-3371

292 homes

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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: Aug 25, 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

28 communities near Holiday

292 homes near Holiday

2 beds

2 baths

1,135 sq ft

Condo

2 beds

2 baths

1,226 sq ft

House

2 beds

2 baths

1,440 sq ft

Villa

2 beds

2 baths

1,110 sq ft

Condo

3 beds

2 baths

1,824 sq ft

House

2 beds

2 baths

918 sq ft

Condo

2 beds

2 baths

1,332 sq ft

Villa

2 beds

1 baths

875 sq ft

Villa

2 beds

2 baths

1,105 sq ft

House

2 beds

2 baths

960 sq ft

Villa

2 beds

2 baths

954 sq ft

Condo

2 beds

2 baths

1,747 sq ft

House

1 beds

1 baths

793 sq ft

Condo

1 beds

1 baths

814 sq ft

Villa

2 beds

2 baths

1,467 sq ft

House

2 beds

2 baths

960 sq ft

Villa

2 beds

2 baths

1,190 sq ft

Villa

2 beds

2 baths

1,903 sq ft

Villa

2 beds

2 baths

1,340 sq ft

Condo

3 beds