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

27 communities near Holiday

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5 rating (1 reviews)

Timber Oaks

<$100k - $200ks

Timber Oaks, Port Richey, FL

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

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

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

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

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

3.5 rating (2 reviews)

Timber Greens

$200ks - $300ks

Timber Greens, New Port Richey, FL

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

Heather Lake Condominiums

$100ks

Heather Lake Condominiums, Dunedin, FL

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

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

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.

Key Vista Villas

$300ks

Key Vista Villas, Holiday, FL

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

Anchorage

$200ks - $300ks

Anchorage, Palm Harbor, FL

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

Esplanade at Starkey Ranc...

$300ks - $700ks

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

Imperial Pines Condominiu...

$100ks - $200ks

Imperial Pines Condominiu..., Clearwater, FL

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

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

Patrician Oaks

$100ks

Patrician Oaks, Dunedin, FL

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

Heather Hills Villas

$100ks

Heather Hills Villas, Dunedin, FL

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

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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

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

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+ 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

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

Linkside Village

$200ks

Linkside Village, Port Richey, FL

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

New Anchorage

835 ANCHORAGE LN, PALM HARBOR, FL, 34685, Palm Harbor, FL 34685

$459,900

3 beds

2 baths

1,822 sq ft

House

835 ANCHORAGE LN, PALM HARBOR, FL, 34685

Community: Anchorage

New Pinehurst Village

1701 PINEHURST RD 13C, DUNEDIN, FL, 3469..., Dunedin, FL 34698

$149,900

1 beds

1 baths

645 sq ft

Condo

1701 PINEHURST RD 13C, DUNEDIN, FL, 3469...

Community: Pinehurst Village

New Heritage Springs

1455 WINDING WILLOW DR, TRINITY, FL, 346..., Trinity, FL 34655

$539,000

4 beds

2 baths

2,177 sq ft

House

1455 WINDING WILLOW DR, TRINITY, FL, 346...

Community: Heritage Springs

New Pine Ridge at Palm Harbor

1870 PINE RIDGE WAY D2, PALM HARBOR, FL,..., Palm Harbor, FL 34684

$170,999

2 beds

2 baths

1,038 sq ft

Condo

1870 PINE RIDGE WAY D2, PALM HARBOR, FL,...

Community: Pine Ridge at Palm Harbor

New Heather Ridge

1370 HEATHER RIDGE BLVD 204, DUNEDIN, FL..., Dunedin, FL 34698

$149,900

2 beds

1 baths

990 sq ft

Condo

1370 HEATHER RIDGE BLVD 204, DUNEDIN, FL...

Community: Heather Ridge

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 Briar Patch

4544 SLIPPERY ROCK RD, NEW PORT RICHEY, ..., New Port Richey, FL 34653

$179,900

2 beds

2 baths

964 sq ft

Villa

4544 SLIPPERY ROCK RD, NEW PORT RICHEY, ...

Community: Briar Patch

New Anchorage

1010 MAINSAIL WAY, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34685

$440,000

2 beds

2 baths

1,574 sq ft

House

1010 MAINSAIL WAY, PALM HARBOR, FL, 3468...

Community: Anchorage

New Heritage Springs

1933 ARBOR KNOLL LOOP, TRINITY, FL, 3465..., Trinity, FL 34655

$399,900

2 beds

2 baths

1,900 sq ft

Villa

1933 ARBOR KNOLL LOOP, TRINITY, FL, 3465...

Community: Heritage Springs

New Summertree

11303 CLEAR OAK CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34654

$350,000

3 beds

2 baths

1,854 sq ft

House

11303 CLEAR OAK CIR, NEW PORT RICHEY, FL...

Community: Summertree

New Timber Oaks

8510 WINDING WOOD DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668

$265,000

2 beds

2 baths

1,461 sq ft

House

8510 WINDING WOOD DR, PORT RICHEY, FL, 3...

Community: Timber Oaks

New Timber Greens

9521 SPRINGMEADOW DR, NEW PORT RICHEY, F..., New Port Richey, FL 34655

$469,999

3 beds

2 baths

1,843 sq ft

House

9521 SPRINGMEADOW DR, NEW PORT RICHEY, F...

Community: Timber Greens

New Highland Lakes on Lake Tarpon

2291 SHELLY DR D, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$215,900

2 beds

2 baths

1,120 sq ft

Condo

2291 SHELLY DR D, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

New Summertree

11704 ASPENWOOD DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654

$239,900

3 beds

2 baths

1,342 sq ft

House

11704 ASPENWOOD DR, NEW PORT RICHEY, FL,...

Community: Summertree

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

Questions? Call us: (727) 800-3371

Imperial Pines Condominiums

3078 EASTLAND BLVD 309, CLEARWATER, FL, ..., Clearwater, FL 33761

$249,900

2 beds

2 baths

1,390 sq ft

Condo

3078 EASTLAND BLVD 309, CLEARWATER, FL, ...

Community: Imperial Pines Condominiums

Heritage Lake

9302 TROWBRIDGE CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655

$199,995

2 beds

2 baths

1,174 sq ft

Condo

9302 TROWBRIDGE CT, NEW PORT RICHEY, FL,...

Community: Heritage Lake

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

Questions? Call us: (727) 800-3371

Timber Oaks

11241 ROLLINGWOOD DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668

$239,995

2 beds

2 baths

1,484 sq ft

House

11241 ROLLINGWOOD DR, PORT RICHEY, FL, 3...

Community: Timber Oaks

Esplanade at Starkey Ranch

3462 FORSYTHIA DR, ODESSA, FL, 33556, Odessa, FL 33556

$1,399,000

3 beds

3 baths

3,095 sq ft

House

3462 FORSYTHIA DR, ODESSA, FL, 33556

Community: Esplanade at Starkey Ranch

Timber Greens

6447 PINE WALK DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655

$320,000

2 beds

2 baths

1,352 sq ft

Villa

6447 PINE WALK DR, NEW PORT RICHEY, FL, ...

Community: Timber Greens

Summertree

11213 KISKADEE CIR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654

$339,000

3 beds

2 baths

1,834 sq ft

House

11213 KISKADEE CIR, NEW PORT RICHEY, FL,...

Community: Summertree

Key Vista Villas

2529 SANDY HILL CT, HOLIDAY, FL, 34691, Holiday, FL 34691

$379,000

2 beds

2 baths

1,555 sq ft

House

2529 SANDY HILL CT, HOLIDAY, FL, 34691

Community: Key Vista Villas

Heritage Springs

1046 ALMONDWOOD DR, TRINITY, FL, 34655, Trinity, FL 34655

$374,900

2 beds

2 baths

1,546 sq ft

Villa

1046 ALMONDWOOD DR, TRINITY, FL, 34655

Community: Heritage Springs

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

Questions? Call us: (727) 800-3371

Key Vista Villas

2945 WOOD POINTE DR, HOLIDAY, FL, 34691, Holiday, FL 34691

$345,000

2 beds

2 baths

1,341 sq ft

House

2945 WOOD POINTE DR, HOLIDAY, FL, 34691

Community: Key Vista Villas

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

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

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

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

Questions? Call us: (727) 800-3371

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

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

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

Highland Lakes on Lake Tarpon

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

$485,000

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

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

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

Questions? Call us: (727) 800-3371

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

Community: Highland Lakes on Lake Tarpon

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

Questions? Call us: (727) 800-3371

Summertree

11621 HOLLY ANN DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654

$269,000

2 beds

2 baths

1,400 sq ft

Villa

11621 HOLLY ANN DR, NEW PORT RICHEY, FL,...

Community: Summertree

Imperial Pines Condominiums

3076 EASTLAND BLVD 210, CLEARWATER, FL, ..., Clearwater, FL 33761

$214,900

2 beds

2 baths

1,250 sq ft

Condo

3076 EASTLAND BLVD 210, CLEARWATER, FL, ...

Community: Imperial Pines Condominiums

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?

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27 communities

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

27 communities near Holiday

283 homes near Holiday

3 beds

2 baths

1,822 sq ft

House

1 beds

1 baths

645 sq ft

Condo

4 beds

2 baths

2,177 sq ft

House

2 beds

2 baths

1,038 sq ft

Condo

2 beds

1 baths

990 sq ft

Condo

2 beds

2 baths

964 sq ft

Villa

2 beds

2 baths

1,574 sq ft

House

2 beds

2 baths

1,900 sq ft

Villa

3 beds

2 baths

1,854 sq ft

House

2 beds

2 baths

1,461 sq ft

House

3 beds

2 baths

1,843 sq ft

House

2 beds

2 baths

1,120 sq ft

Condo

3 beds

2 baths

1,342 sq ft

House

2 beds

2 baths

1,390 sq ft

Condo

2 beds

2 baths

1,174 sq ft

Condo

2 beds

2 baths

1,484 sq ft

House

3 beds

3 baths

3,095 sq ft

House

2 beds

2 baths

1,352 sq ft

Villa

3 beds

2 baths

1,834 sq ft

House

2 beds