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

272 homes near Holiday

Sort by:

Relevance

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

4.7 rating (13 reviews)

Heritage Springs

$200ks - $500ks

Heritage Springs, Trinity, FL

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

Summertree

$200ks - $300ks

Summertree, New Port Richey, FL

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

Heather Lake Condominiums

$100ks

Heather Lake Condominiums, Dunedin, FL

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

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

Questions? Call us: (727) 800-3371

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

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

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

Edgewater Arms

$400ks - $600ks

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

Briar Patch, New Port Richey, FL

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

Esplanade at Starkey Ranc...

$300ks - $700ks

Esplanade at Starkey Ranc..., Odessa, FL

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

Key Vista Villas

$300ks

Key Vista Villas, Holiday, FL

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

2 rating (1 reviews)

Beacon Lakes

$100ks

Beacon Lakes, New Port Richey, FL

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

Green Dolphin

$100ks

Green Dolphin, Tarpon Springs, FL

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

Imperial Pines Condominiu...

$100ks - $200ks

Imperial Pines Condominiu..., Clearwater, FL

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

Heather Ridge

$100ks - $200ks

Heather Ridge, Dunedin, FL

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

Anchorage

$200ks - $300ks

Anchorage, Palm Harbor, FL

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

Pinehurst Village

$100ks

Pinehurst Village, Dunedin, FL

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

Heather Hills Villas

$100ks

Heather Hills Villas, Dunedin, FL

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

Scotsdale Cluster Condomi...

$200ks

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

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

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+ communities in Holiday? 55places can help!

Questions? Call us: (727) 800-3371

New Pine Ridge at Palm Harbor

1870 PINE RIDGE WAY G1, PALM HARBOR, FL,..., Palm Harbor, FL 34684

$189,000

2 beds

2 baths

1,150 sq ft

Condo

1870 PINE RIDGE WAY G1, PALM HARBOR, FL,...

Community: Pine Ridge at Palm Harbor

New Summertree

11455 GOLF ROUND DR, NEW PORT RICHEY, FL..., New Port Richey, FL 34654

$259,900

3 beds

2 baths

1,548 sq ft

Villa

11455 GOLF ROUND DR, NEW PORT RICHEY, FL...

Community: Summertree

New Highland Lakes on Lake Tarpon

3157 MISSION GROVE DR, PALM HARBOR, FL, ..., Palm Harbor, FL 34684

$123,000

2 beds

1 baths

806 sq ft

Condo

3157 MISSION GROVE DR, PALM HARBOR, FL, ...

Community: Highland Lakes on Lake Tarpon

New Beacon Lakes

3835 LIGHTHOUSE WAY, NEW PORT RICHEY, FL..., New Port Richey, FL 34652

$155,000

2 beds

2 baths

1,144 sq ft

Condo

3835 LIGHTHOUSE WAY, NEW PORT RICHEY, FL...

Community: Beacon Lakes

New Heritage Springs

1032 DUSTAN PL, TRINITY, FL, 34655, Trinity, FL 34655

$399,000

3 beds

2 baths

1,704 sq ft

House

1032 DUSTAN PL, TRINITY, FL, 34655

Community: Heritage Springs

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

Questions? Call us: (727) 800-3371

New Timber Oaks

11541 ORLEANS LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668

$159,500

2 beds

2 baths

1,152 sq ft

Condo

11541 ORLEANS LN, PORT RICHEY, FL, 34668

Community: Timber Oaks

New Timber Greens

9413 SUMMERBREEZE TER, NEW PORT RICHEY, ..., New Port Richey, FL 34655

$440,000

3 beds

2 baths

2,022 sq ft

House

9413 SUMMERBREEZE TER, NEW PORT RICHEY, ...

Community: Timber Greens

New Highland Lakes on Lake Tarpon

2954 CURLING CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$295,000

2 beds

2 baths

1,069 sq ft

House

2954 CURLING CT, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

New Highland Lakes on Lake Tarpon

1472 QUEEN ANNE BLVD, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684

$439,000

2 beds

2 baths

1,211 sq ft

House

1472 QUEEN ANNE BLVD, PALM HARBOR, FL, 3...

Community: Highland Lakes on Lake Tarpon

New Timber Oaks

10600 SALAMANCA DR, PORT RICHEY, FL, 346..., Port Richey, FL 34668

$195,000

2 beds

2 baths

1,107 sq ft

House

10600 SALAMANCA DR, PORT RICHEY, FL, 346...

Community: Timber Oaks

New Highland Lakes on Lake Tarpon

2472 MALCOLM DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$414,900

2 beds

2 baths

1,330 sq ft

House

2472 MALCOLM DR, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

New Highland Lakes on Lake Tarpon

2828 HIGHLANDS BLVD A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684

$249,900

2 beds

2 baths

1,000 sq ft

Condo

2828 HIGHLANDS BLVD A, PALM HARBOR, FL, ...

Community: Highland Lakes on Lake Tarpon

New Highland Lakes on Lake Tarpon

860 MACLAREN DR B, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684

$259,900

2 beds

2 baths

1,230 sq ft

Condo

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

Community: Highland Lakes on Lake Tarpon

New Heritage Lake

9319 TROWBRIDGE CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655

$207,000

2 beds

2 baths

1,174 sq ft

Villa

9319 TROWBRIDGE CT, NEW PORT RICHEY, FL,...

Community: Heritage Lake

New Heritage Springs

11917 HADLEIGH WAY, TRINITY, FL, 34655, Trinity, FL 34655

$549,900

4 beds

4 baths

2,635 sq ft

House

11917 HADLEIGH WAY, TRINITY, FL, 34655

Community: Heritage Springs

New Heritage Springs

1852 ARBOR KNOLL LOOP, TRINITY, FL, 3465..., Trinity, FL 34655

$387,000

3 beds

2 baths

1,683 sq ft

House

1852 ARBOR KNOLL LOOP, TRINITY, FL, 3465...

House

9903 KINGSPORT AVE, NEW PORT RICHEY, FL,...

Community: Heritage Lake

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

Questions? Call us: (727) 800-3371

Heather Lake Condominiums

940 VIRGINIA ST 103, DUNEDIN, FL, 34698, Dunedin, FL 34698

$195,000

2 beds

2 baths

927 sq ft

Condo

940 VIRGINIA ST 103, DUNEDIN, FL, 34698

Community: Heather Lake Condominiums

Briar Patch

4557 GLEN HOLW, NEW PORT RICHEY, FL, 346..., New Port Richey, FL 34653

$189,900

2 beds

2 baths

964 sq ft

Villa

4557 GLEN HOLW, NEW PORT RICHEY, FL, 346...

Community: Briar Patch

Heather Ridge

1485 HALSEY DR 105, DUNEDIN, FL, 34698, Dunedin, FL 34698

$109,000

1 beds

1 baths

919 sq ft

Condo

1485 HALSEY DR 105, DUNEDIN, FL, 34698

Community: Heather Ridge

Heritage Springs

1624 LAKESTONE DR, TRINITY, FL, 34655, Trinity, FL 34655

$475,000

3 beds

2 baths

2,090 sq ft

House

1624 LAKESTONE DR, TRINITY, FL, 34655

Community: Heritage Springs

Timber Oaks

8225 SAN FELIPE CT, PORT RICHEY, FL, 346..., Port Richey, FL 34668

$274,900

2 beds

2 baths

1,274 sq ft

House

8225 SAN FELIPE CT, PORT RICHEY, FL, 346...

Community: Timber Oaks

Timber Oaks

10520 SPRINGWOOD DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668

$260,000

2 beds

2 baths

1,218 sq ft

House

10520 SPRINGWOOD DR, PORT RICHEY, FL, 34...

Community: Timber Oaks

Heather Lake Condominiums

948 VIRGINIA ST 207, DUNEDIN, FL, 34698, Dunedin, FL 34698

$125,000

1 beds

1 baths

869 sq ft

Condo

948 VIRGINIA ST 207, DUNEDIN, FL, 34698

Community: Heather Lake Condominiums

Heritage Springs

1430 CANBERLEY CT, TRINITY, FL, 34655, Trinity, FL 34655

$450,000

3 beds

2 baths

2,098 sq ft

House

1430 CANBERLEY CT, TRINITY, FL, 34655

Community: Heritage Springs

Beacon Lakes

3836 LIGHTHOUSE WAY 3836, NEW PORT RICHE..., New Port Richey, FL 34652

$135,000

2 beds

2 baths

1,144 sq ft

Condo

3836 LIGHTHOUSE WAY 3836, NEW PORT RICHE...

Community: Beacon Lakes

Heritage Springs

1237 ALMONDWOOD DR, TRINITY, FL, 34655, Trinity, FL 34655

$419,900

3 beds

2 baths

2,016 sq ft

House

1237 ALMONDWOOD DR, TRINITY, FL, 34655

Community: Heritage Springs

Heritage Lake

9058 ARUNDLE PL, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34655

$224,900

2 beds

2 baths

1,553 sq ft

Condo

9058 ARUNDLE PL, NEW PORT RICHEY, FL, 34...

Community: Heritage Lake

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

Questions? Call us: (727) 800-3371

Patrician Oaks

840 VIRGINIA ST 303, DUNEDIN, FL, 34698, Dunedin, FL 34698

$128,000

2 beds

1 baths

1,004 sq ft

Condo

840 VIRGINIA ST 303, DUNEDIN, FL, 34698

Community: Patrician Oaks

Pine Ridge at Palm Harbor

2687 PINE RIDGE WAY H1, PALM HARBOR, FL,..., Palm Harbor, FL 34684

$183,900

2 beds

2 baths

1,104 sq ft

Condo

2687 PINE RIDGE WAY H1, PALM HARBOR, FL,...

Community: Pine Ridge at Palm Harbor

1 2 3 4 5 6…7

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 270 days. The average price of homes for sale in this community is approximately $346,575, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Key Vista Villas average around $346,575.

Want more information about active adult communities around Holiday?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Holiday?

Call us: (727) 800-3371

272 homes

Remove Boundaries ×

Map Satellite

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.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: May 25, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

27 communities near Holiday

272 homes near Holiday

2 beds

2 baths

1,150 sq ft

Condo

3 beds

2 baths

1,548 sq ft

Villa

2 beds

1 baths

806 sq ft

Condo

2 beds

2 baths

1,144 sq ft

Condo

3 beds

2 baths

1,704 sq ft

House

2 beds

2 baths

1,152 sq ft

Condo

3 beds

2 baths

2,022 sq ft

House

2 beds

2 baths

1,069 sq ft

House

2 beds

2 baths

1,211 sq ft

House

2 beds

2 baths

1,107 sq ft

House

2 beds

2 baths

1,330 sq ft

House

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,174 sq ft

Villa

4 beds

4 baths

2,635 sq ft

House

3 beds

2 baths

1,683 sq ft

House

2 beds

2 baths

993 sq ft

Condo

2 beds

2 baths

1,699 sq ft

House

2 beds

2 baths

1,672 sq ft

Villa

2 beds