Holiday, FL 55+ active adult communities & homes for sale - Page 2

281 homes near Holiday

Sort by:

Relevance

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

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

Heather Lake Condominiums

$100ks

Heather Lake Condominiums, Dunedin, FL

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

Green Dolphin

$100ks

Green Dolphin, Tarpon Springs, FL

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

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

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

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

Esplanade at Starkey Ranc...

$300ks - $700ks

Esplanade at Starkey Ranc..., Odessa, FL

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

Imperial Pines Condominiu...

$100ks - $200ks

Imperial Pines Condominiu..., Clearwater, FL

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

Briar Patch

$100ks

Briar Patch, New Port Richey, FL

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

2 rating (1 reviews)

Beacon Lakes

$100ks

Beacon Lakes, New Port Richey, FL

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

Heather Ridge

$100ks - $200ks

Heather Ridge, Dunedin, FL

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

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

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

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

3957 TARPON POINTE CIR, PALM HARBOR, FL,...

Condo

11308 VERSAILLES LN C, PORT RICHEY, FL, ...

Community: Timber Oaks

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

Questions? Call us: (727) 800-3371

Heather Lake Condominiums

946 VIRGINIA ST 104- J, DUNEDIN, FL, 346..., Dunedin, FL 34698

$109,900

1 beds

1 baths

770 sq ft

Condo

946 VIRGINIA ST 104- J, DUNEDIN, FL, 346...

Community: Heather Lake Condominiums

Edgewater Arms

620 EDGEWATER DRS 103, DUNEDIN, FL, 3469..., Dunedin, FL 34698

$275,000

1 beds

1 baths

840 sq ft

Condo

620 EDGEWATER DRS 103, DUNEDIN, FL, 3469...

Community: Edgewater Arms

Highland Lakes on Lake Tarpon

1194 ROYAL BLVD, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$499,000

3 beds

2 baths

1,820 sq ft

House

1194 ROYAL BLVD, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

Royal Stewart Arms

7 ELGIN PL 301, DUNEDIN, FL, 34698, Dunedin, FL 34698

$349,000

2 beds

2 baths

1,181 sq ft

Condo

7 ELGIN PL 301, DUNEDIN, FL, 34698

Community: Royal Stewart Arms

Highland Lakes on Lake Tarpon

3132 BRUNSWICK CIR, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684

$474,900

3 beds

2 baths

1,858 sq ft

House

3132 BRUNSWICK CIR, PALM HARBOR, FL, 346...

Community: Highland Lakes on Lake Tarpon

Highland Lakes on Lake Tarpon

1446 QUEEN ANNE BLVD, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684

$350,000

2 beds

2 baths

1,296 sq ft

House

1446 QUEEN ANNE BLVD, PALM HARBOR, FL, 3...

Community: Highland Lakes on Lake Tarpon

Highland Lakes on Lake Tarpon

1223 TIMBERBROOKE DR, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684

$439,900

3 beds

2 baths

1,468 sq ft

House

1223 TIMBERBROOKE DR, PALM HARBOR, FL, 3...

Community: Highland Lakes on Lake Tarpon

Royal Stewart Arms

7 DUNOON PL 104, DUNEDIN, FL, 34698, Dunedin, FL 34698

$340,000

2 beds

2 baths

1,141 sq ft

Condo

7 DUNOON PL 104, DUNEDIN, FL, 34698

Community: Royal Stewart Arms

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

Questions? Call us: (727) 800-3371

Esplanade at Starkey Ranch

11414 JUGLANS DR, ODESSA, FL, 33556, Odessa, FL 33556

$785,000

4 beds

3 baths

2,466 sq ft

House

11414 JUGLANS DR, ODESSA, FL, 33556

Community: Esplanade at Starkey Ranch

Summertree

11515 SCOTCH PINE DR, NEW PORT RICHEY, F..., New Port Richey, FL 34654

$225,000

2 beds

2 baths

1,038 sq ft

House

11515 SCOTCH PINE DR, NEW PORT RICHEY, F...

Community: Summertree

Green Dolphin

2014 GOLFVIEW DR 2014, TARPON SPRINGS, F..., Tarpon Springs, FL 34689

$235,000

3 beds

2 baths

1,560 sq ft

Condo

2014 GOLFVIEW DR 2014, TARPON SPRINGS, F...

Community: Green Dolphin

Royal Stewart Arms

8 GLENCOE PL 105, DUNEDIN, FL, 34698, Dunedin, FL 34698

$215,000

1 beds

1 baths

948 sq ft

Condo

8 GLENCOE PL 105, DUNEDIN, FL, 34698

Community: Royal Stewart Arms

Timber Oaks

11341 DOLLAR LAKE DR 1, PORT RICHEY, FL,..., Port Richey, FL 34668

$194,777

2 beds

2 baths

1,100 sq ft

Condo

11341 DOLLAR LAKE DR 1, PORT RICHEY, FL,...

Community: Timber Oaks

Heritage Lake

4712 COACHMEN RD, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34655

$289,000

2 beds

2 baths

1,360 sq ft

House

4712 COACHMEN RD, NEW PORT RICHEY, FL, 3...

Community: Heritage Lake

Timber Greens

9525 SPRINGMEADOW DR, NEW PORT RICHEY, F..., New Port Richey, FL 34655

$364,900

3 beds

2 baths

1,932 sq ft

House

9525 SPRINGMEADOW DR, NEW PORT RICHEY, F...

Community: Timber Greens

Highland Lakes on Lake Tarpon

2240 SPRUCE LN D, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$210,000

2 beds

2 baths

918 sq ft

Condo

2240 SPRUCE LN D, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

Timber Oaks

8030 GLENEAGLE DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668

$219,900

2 beds

2 baths

1,001 sq ft

House

8030 GLENEAGLE DR, PORT RICHEY, FL, 3466...

House

2217 SEQUOIA DR, CLEARWATER, FL, 33763

Community: Village on the Green

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

Questions? Call us: (727) 800-3371

Heritage Springs

1751 LAKESTONE DR, TRINITY, FL, 34655, Trinity, FL 34655

$410,000

3 beds

2 baths

1,841 sq ft

House

1751 LAKESTONE DR, TRINITY, FL, 34655

Community: Heritage Springs

Timber Oaks

11210 DOLLAR LAKE DR 2, PORT RICHEY, FL,..., Port Richey, FL 34668

$94,000

2 beds

2 baths

1,210 sq ft

Condo

11210 DOLLAR LAKE DR 2, PORT RICHEY, FL,...

Community: Timber Oaks

1 2 3 4 5 6 7…8

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.

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

281 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: Apr 03, 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 - Page 2

26 communities near Holiday

281 homes near Holiday

2 beds

2 baths

1,377 sq ft

House

3 beds

2 baths

1,709 sq ft

House

3 beds

2 baths

1,280 sq ft

House

2 beds

2 baths

999 sq ft

Villa

3 beds

2 baths

1,588 sq ft

House

2 beds

1 baths

875 sq ft

Villa

2 beds

2 baths

1,040 sq ft

Condo

2 beds

2 baths

1,148 sq ft

Villa

2 beds

2 baths

1,148 sq ft

Villa

2 beds

1 baths

1,100 sq ft

Condo

2 beds

2 baths

980 sq ft

Condo

2 beds

2 baths

1,340 sq ft

Villa

2 beds

2 baths

1,171 sq ft

Condo

1 beds

1 baths

770 sq ft

Condo

1 beds

1 baths

840 sq ft

Condo

3 beds

2 baths

1,820 sq ft

House

2 beds

2 baths

1,181 sq ft

Condo

3 beds

2 baths

1,858 sq ft

House

2 beds

2 baths

1,296 sq ft

House

3 beds