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

28 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

3.5 rating (2 reviews)

Timber Greens

$200ks - $300ks

Timber Greens, New Port Richey, FL

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

Edgewater Arms

$400ks - $600ks

Edgewater Arms, Dunedin, FL

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

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

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

Briar Patch, New Port Richey, FL

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

Victoria Lakes

$800ks - $1Ms

Victoria Lakes, Odessa, FL

New Construction | Age-targeted | Built 2025 - present | 166 homes

2 rating (1 reviews)

Beacon Lakes

$100ks

Beacon Lakes, New Port Richey, FL

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

Key Vista Villas

$300ks

Key Vista Villas, Holiday, FL

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

Anchorage

$200ks - $300ks

Anchorage, Palm Harbor, FL

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

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

Esplanade at Starkey Ranc...

$300ks - $700ks

Esplanade at Starkey Ranc..., Odessa, FL

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

Patrician Oaks

$100ks

Patrician Oaks, Dunedin, FL

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

Heather Ridge

$100ks - $200ks

Heather Ridge, Dunedin, FL

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

Linkside Village

$200ks

Linkside Village, Port Richey, FL

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

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+ communities in Holiday? 55places can help!

Questions? Call us: (727) 800-3371

Country Oaks

$100ks

Country Oaks, Hudson, FL

10007 BROOKDALE DR, 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

2261 SHELLY DR D, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$204,500

2 beds

2 baths

918 sq ft

Villa

2261 SHELLY DR D, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

New Edgewater Arms

620 EDGEWATER DR 204, DUNEDIN, FL, 34698, Dunedin, FL 34698

$279,900

1 beds

1 baths

840 sq ft

Condo

620 EDGEWATER DR 204, DUNEDIN, FL, 34698

Community: Edgewater Arms

New Anchorage

2211 PORTSIDE PSGE, PALM HARBOR, FL, 346..., Palm Harbor, FL 34685

$439,000

2 beds

2 baths

1,778 sq ft

House

2211 PORTSIDE PSGE, PALM HARBOR, FL, 346...

Community: Anchorage

New Highland Lakes on Lake Tarpon

3156 HIGHLANDS BLVD A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684

$115,000

1 beds

1 baths

636 sq ft

Villa

3156 HIGHLANDS BLVD A, PALM HARBOR, FL, ...

Community: Highland Lakes on Lake Tarpon

New Heather Ridge

2220 MARSHALL DR, DUNEDIN, FL, 34698, Dunedin, FL 34698

$297,500

2 beds

2 baths

1,400 sq ft

Villa

2220 MARSHALL DR, DUNEDIN, FL, 34698

Community: Heather Ridge

Key Vista Villas

2230 PLEASANT HILL LN, HOLIDAY, FL, 3469..., Holiday, FL 34691

$324,900

2 beds

2 baths

1,341 sq ft

House

2230 PLEASANT HILL LN, HOLIDAY, FL, 3469...

Community: Key Vista Villas

Heritage Lake

9851 KINGSPORT AVE, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655

$291,100

3 beds

2 baths

1,558 sq ft

House

9851 KINGSPORT AVE, NEW PORT RICHEY, FL,...

Community: Heritage Lake

Summertree

11501 BLOOMINGTON CT, NEW PORT RICHEY, F..., New Port Richey, FL 34654

$339,900

3 beds

2 baths

1,863 sq ft

House

11501 BLOOMINGTON CT, NEW PORT RICHEY, F...

Community: Summertree

Highland Lakes on Lake Tarpon

1529 E DORCHESTER DR, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684

$438,900

3 beds

2 baths

1,475 sq ft

House

1529 E DORCHESTER DR, PALM HARBOR, FL, 3...

Community: Highland Lakes on Lake Tarpon

Summertree

11413 BLOOMINGTON CT, NEW PORT RICHEY, F..., New Port Richey, FL 34654

$374,900

3 beds

2 baths

2,045 sq ft

House

11413 BLOOMINGTON CT, NEW PORT RICHEY, F...

Community: Summertree

Edgewater Arms

622 EDGEWATER DR 823, DUNEDIN, FL, 34698, Dunedin, FL 34698

$765,000

3 beds

2 baths

2,030 sq ft

Condo

622 EDGEWATER DR 823, DUNEDIN, FL, 34698

Community: Edgewater Arms

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

Questions? Call us: (727) 800-3371

Highland Lakes on Lake Tarpon

3351 STONEHAVEN CT C, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684

$269,000

2 beds

2 baths

1,230 sq ft

Villa

3351 STONEHAVEN CT C, PALM HARBOR, FL, 3...

Community: Highland Lakes on Lake Tarpon

Pinehurst Village

1701 PINEHURST RD 34D, DUNEDIN, FL, 3469..., Dunedin, FL 34698

$123,900

1 beds

1 baths

645 sq ft

Condo

1701 PINEHURST RD 34D, DUNEDIN, FL, 3469...

Community: Pinehurst Village

Timber Oaks

8141 BUGLE CT 2, PORT RICHEY, FL, 34668, Port Richey, FL 34668

$134,900

2 beds

2 baths

1,000 sq ft

Condo

8141 BUGLE CT 2, PORT RICHEY, FL, 34668

Community: Timber Oaks

Briar Patch

6418 CABBAGE LN, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34653

$174,900

2 beds

2 baths

940 sq ft

Villa

6418 CABBAGE LN, NEW PORT RICHEY, FL, 34...

Community: Briar Patch

Heritage Lake

9022 RAMSGATE DR 9022, NEW PORT RICHEY, ..., New Port Richey, FL 34655

$195,000

2 beds

2 baths

1,215 sq ft

Condo

9022 RAMSGATE DR 9022, NEW PORT RICHEY, ...

Community: Heritage Lake

Highland Lakes on Lake Tarpon

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

$469,000

3 beds

2 baths

1,732 sq ft

House

999 GILLESPIE DR, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

Highland Lakes on Lake Tarpon

2740 HAMBLE VILLAGE LN, PALM HARBOR, FL,..., Palm Harbor, FL 34684

$429,900

3 beds

2 baths

1,595 sq ft

House

2740 HAMBLE VILLAGE LN, PALM HARBOR, FL,...

Community: Highland Lakes on Lake Tarpon

Highland Lakes on Lake Tarpon

3127 MISSION GROVE DR 3127, PALM HARBOR,..., Palm Harbor, FL 34684

$125,000

2 beds

2 baths

866 sq ft

Condo

3127 MISSION GROVE DR 3127, PALM HARBOR,...

Community: Highland Lakes on Lake Tarpon

Village on the Green

2538 OAKLEAF LN 33B, CLEARWATER, FL, 337..., Clearwater, FL 33763

$259,900

2 beds

2 baths

960 sq ft

Villa

2538 OAKLEAF LN 33B, CLEARWATER, FL, 337...

Community: Village on the Green

Heritage Lake

9414 CAPE CHARLES AVE, NEW PORT RICHEY, ..., New Port Richey, FL 34655

$260,000

2 beds

2 baths

1,308 sq ft

House

9414 CAPE CHARLES AVE, NEW PORT RICHEY, ...

Community: Heritage Lake

Highland Lakes on Lake Tarpon

3271 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$392,700

2 beds

2 baths

1,332 sq ft

Villa

3271 MCMATH DR, PALM HARBOR, FL, 34684

House

9519 SCENIC PINE 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

Timber Oaks

8634 WINDING WOOD DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668

$215,000

2 beds

2 baths

1,112 sq ft

House

8634 WINDING WOOD DR, PORT RICHEY, FL, 3...

Community: Timber Oaks

Highland Lakes on Lake Tarpon

3472 MACLAREN DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$319,900

2 beds

2 baths

1,289 sq ft

Villa

3472 MACLAREN DR, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

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

28 communities

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REIN updates its listings on a daily basis. Data last updated: Jun 18, 2026.
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Holiday, FL 55+ active adult communities & homes for sale

28 communities near Holiday

262 homes near Holiday

2 beds

2 baths

1,148 sq ft

Villa

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

875 sq ft

Condo

3 beds

2 baths

1,719 sq ft

Villa

2 beds

2 baths

1,300 sq ft

House

2 beds

2 baths

918 sq ft

Villa

1 beds

1 baths

840 sq ft

Condo

2 beds

2 baths

1,778 sq ft

House

1 beds

1 baths

636 sq ft

Villa

2 beds

2 baths

1,400 sq ft

Villa

2 beds

2 baths

1,341 sq ft

House

3 beds

2 baths

1,558 sq ft

House

3 beds

2 baths

1,863 sq ft

House

3 beds

2 baths

1,475 sq ft

House

3 beds

2 baths

2,045 sq ft

House

3 beds

2 baths

2,030 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Villa

1 beds

1 baths

645 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds