Call us at (727) 800-3371 to learn more about active adult communities in Holiday

Holiday, FL 55+ active adult communities & homes for sale - Page 4

292 homes near Holiday

Sort by:

Relevance

Relevance

Key Vista Villas
$300Ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 homes
5 rating (1 reviews) Highland Lakes on Lake Ta...
<$100k - $500Ks
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
$300Ks - $500Ks
Heritage Springs, Trinity, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,337 homes
5 rating (1 reviews) Timber Oaks
<$100k - $300Ks
Timber Oaks, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1973 - 1997 | 1,000 homes
Heritage Lake
$100Ks - $300Ks
Heritage Lake, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1994 | 932 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Summertree
$100Ks - $300Ks
Summertree, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1974 - 2015 | 800 homes
3.5 rating (2 reviews) Timber Greens
$200Ks - $400Ks
Timber Greens, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1994 - 2004 | 783 homes
Esplanade at Starkey Ranc...
$400Ks - $900Ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only | Age-targeted | Built 2016 - 2022 | 517 homes
3.3 rating (3 reviews) Royal Stewart Arms
$200Ks - $400Ks
Royal Stewart Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1968 - 1975 | 449 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 (1 reviews) Village on the Green
$100Ks - $200Ks
Village on the Green, Clearwater, FL
Resale Only | 55+ age-restricted | Built 1978 - 1981 | 448 homes
Green Dolphin
<$100k - $200Ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
Anchorage
$400Ks
Anchorage, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 homes
Heather Ridge
$100Ks
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
5 rating (1 reviews) Pine Ridge at Palm Harbor
$100Ks
Pine Ridge at Palm Harbor, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1983 - 1983 | 264 homes
Pinehurst Village
$100Ks - $200Ks
Pinehurst Village, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 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
$100Ks - $1Ms
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.
Heather Lake Condominiums
$100Ks - $200Ks
Heather Lake Condominiums, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 homes
Briar Patch
$100Ks - $200Ks
Briar Patch, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 homes
Imperial Pines Condominiu...
$100Ks - $200Ks
Imperial Pines Condominiu..., Clearwater, FL
Resale Only | 55+ age-restricted | Built 1985 - 1985 | 181 homes
Scotsdale Cluster Condomi...
$300Ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Patrician Oaks
<$100k
Patrician Oaks, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 120 homes
Linkside Village
$100Ks - $200Ks
Linkside Village, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 100 homes
Heather Hills Villas
<$100k - $200Ks
Heather Hills Villas, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1971 - 1976 | 64 homes
Country Oaks
$100Ks
Country Oaks, Hudson, FL
Resale Only | 55+ age-restricted | Built 1981 - 1986 | 42 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.
New Port Corners
$200Ks - $500Ks
New Port Corners, New Port Richey, FL
New Construction | 55+ age-restricted | Built 2025 - present
Green Dolphin 2201 PINE DR, TARPON SPRINGS, FL, 34689, Tarpon Springs, FL 34689
$272,000

2 beds

|

2 baths

|

1,320 sq ft

|

Villa

2201 PINE DR, TARPON SPRINGS, FL, 34689
Community: Green Dolphin
Imperial Pines Condominiums 3062 EASTLAND BLVD 406, CLEARWATER, FL, ..., Clearwater, FL 33761
$150,000

1 beds

|

1 baths

|

920 sq ft

|

Condo

3062 EASTLAND BLVD 406, CLEARWATER, FL, ...
Country Oaks 7745 EUREKA DR # 7745, HUDSON, FL, 34667, Hudson, FL 34667
$118,900

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

7745 EUREKA DR # 7745, HUDSON, FL, 34667
Community: Country Oaks
Pinehurst Village 1701 PINEHURST RD APT 24B, DUNEDIN, FL, ..., Dunedin, FL 34698
$179,900

2 beds

|

1 baths

|

875 sq ft

|

Villa

1701 PINEHURST RD APT 24B, DUNEDIN, FL, ...
Community: Pinehurst Village
Summertree 11521 ROSE TREE DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$275,000

2 beds

|

2 baths

|

1,777 sq ft

|

House

11521 ROSE TREE 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
Highland Lakes on Lake Tarpon 946 MADRID DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$329,400

2 beds

|

2 baths

|

980 sq ft

|

Villa

946 MADRID DR, PALM HARBOR, FL, 34684
Heather Hills Villas 858 CAMBRIDGE CT # 858, DUNEDIN, FL, 346..., Dunedin, FL 34698
$210,000

2 beds

|

2 baths

|

990 sq ft

|

Condo

858 CAMBRIDGE CT # 858, DUNEDIN, FL, 346...
Heather Hills Villas 832 CAMBRIDGE CT, DUNEDIN, FL, 34698, Dunedin, FL 34698
$168,000

1 beds

|

1 baths

|

739 sq ft

|

Villa

832 CAMBRIDGE CT, DUNEDIN, FL, 34698
Highland Lakes on Lake Tarpon 1164 RUSTLEWOOD CT, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$385,000

2 beds

|

2 baths

|

1,282 sq ft

|

Villa

1164 RUSTLEWOOD CT, PALM HARBOR, FL, 346...
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.
Highland Lakes on Lake Tarpon 2932 MACALPIN DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$419,500

2 beds

|

2 baths

|

1,539 sq ft

|

House

2932 MACALPIN DR, PALM HARBOR, FL, 34684
Briar Patch 6520 THICKET TRL, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34653
$269,000

2 beds

|

2 baths

|

1,359 sq ft

|

Townhouse

6520 THICKET TRL, NEW PORT RICHEY, FL, 3...
Community: Briar Patch
Summertree 11150 PARADISE POINT WAY, NEW PORT RICHE..., New Port Richey, FL 34654
$319,900

3 beds

|

2 baths

|

1,558 sq ft

|

House

11150 PARADISE POINT WAY, NEW PORT RICHE...
Community: Summertree
Heritage Lake 4916 TROON LN, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34655
$268,345

2 beds

|

2 baths

|

1,309 sq ft

|

Condo

4916 TROON LN, NEW PORT RICHEY, FL, 3465...
Community: Heritage Lake
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Highland Lakes on Lake Tarpon 1605 WHITEBRIDGE DR B, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$195,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1605 WHITEBRIDGE DR B, PALM HARBOR, FL, ...
Edgewater Arms 634 EDGEWATER DR 644, DUNEDIN, FL, 34698, Dunedin, FL 34698
$825,000

2 beds

|

3 baths

|

2,330 sq ft

|

Condo

634 EDGEWATER DR 644, DUNEDIN, FL, 34698
Community: Edgewater Arms
Summertree 11723 FOXWORTH LN, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34654
$258,000

2 beds

|

2 baths

|

1,096 sq ft

|

House

11723 FOXWORTH LN, NEW PORT RICHEY, FL, ...
Community: Summertree
Pine Ridge at Palm Harbor 2687 PINE RIDGE WAY F2, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$144,900

1 beds

|

1 baths

|

805 sq ft

|

Condo

2687 PINE RIDGE WAY F2, PALM HARBOR, FL,...
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.
Pine Ridge at Palm Harbor 2687 PINE RIDGE WAY E1, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$141,000

1 beds

|

1 baths

|

805 sq ft

|

Condo

2687 PINE RIDGE WAY E1, PALM HARBOR, FL,...
Pine Ridge at Palm Harbor 2642 PINE RIDGE WAY D2, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$144,900

1 beds

|

1 baths

|

805 sq ft

|

Condo

2642 PINE RIDGE WAY D2, PALM HARBOR, FL,...
Timber Oaks 10600 MIRA VISTA DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$275,000

2 beds

|

2 baths

|

1,561 sq ft

|

House

10600 MIRA VISTA DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 2320 SHELLY DR B, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$209,900

2 beds

|

2 baths

|

918 sq ft

|

Condo

2320 SHELLY DR B, PALM HARBOR, FL, 34684
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Green Dolphin 1250 S PINELLAS AVE 506, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$102,500

1 beds

|

1 baths

|

669 sq ft

|

Condo

1250 S PINELLAS AVE 506, TARPON SPRINGS,...
Community: Green Dolphin
Timber Oaks 8101 CASUARINA DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$227,500

2 beds

|

2 baths

|

1,107 sq ft

|

House

8101 CASUARINA DR, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Heritage Lake 9902 SAINT JOSEPH CT, NEW PORT RICHEY, F..., New Port Richey, FL 34655
$325,000

2 beds

|

2 baths

|

1,747 sq ft

|

House

9902 SAINT JOSEPH CT, NEW PORT RICHEY, F...
Community: Heritage Lake
Timber Oaks 10803 HACHITA DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$219,999

2 beds

|

2 baths

|

1,034 sq ft

|

House

10803 HACHITA DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
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.
Heather Lake Condominiums 960 VIRGINIA ST 201, DUNEDIN, FL, 34698, Dunedin, FL 34698
$130,000

2 beds

|

2 baths

|

1,040 sq ft

|

Condo

960 VIRGINIA ST 201, DUNEDIN, FL, 34698
Timber Oaks 10733 FALLEN LEAF LN, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$205,000

2 beds

|

2 baths

|

1,470 sq ft

|

House

10733 FALLEN LEAF LN, PORT RICHEY, FL, 3...
Community: Timber Oaks
Heather Lake Condominiums 936 VIRGINIA ST 208, DUNEDIN, FL, 34698, Dunedin, FL 34698
$150,000

2 beds

|

2 baths

|

1,010 sq ft

|

Condo

936 VIRGINIA ST 208, DUNEDIN, FL, 34698
Highland Lakes on Lake Tarpon 3540 CAYMAN CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$345,000

2 beds

|

2 baths

|

1,325 sq ft

|

Villa

3540 CAYMAN CT, PALM HARBOR, FL, 34684
Edgewater Arms 632 EDGEWATER DR UNIT 238, DUNEDIN, FL, ..., Dunedin, FL 34698
$410,000

2 beds

|

2 baths

|

1,220 sq ft

|

Condo

632 EDGEWATER DR UNIT 238, DUNEDIN, FL, ...
Community: Edgewater Arms
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 11435 STANSBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$185,000

2 beds

|

2 baths

|

972 sq ft

|

House

11435 STANSBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Timber Oaks 11541 ORLEANS LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$209,000

2 beds

|

2 baths

|

1,152 sq ft

|

Condo

11541 ORLEANS LN, PORT RICHEY, FL, 34668
Community: Timber Oaks
Timber Oaks 11241 DOLLAR LAKE DR 5, PORT RICHEY, FL,..., Port Richey, FL 34668
$150,000

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

11241 DOLLAR LAKE DR 5, PORT RICHEY, FL,...
Community: Timber Oaks
Beacon Lakes 4014 DAVIT DR A, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34652
$139,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

4014 DAVIT DR A, NEW PORT RICHEY, FL, 34...
Community: Beacon Lakes
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.
Anchorage 1128 LANYARD ST, PALM HARBOR, FL, 34685, Palm Harbor, FL 34685
$429,000

2 beds

|

2 baths

|

1,760 sq ft

|

House

1128 LANYARD ST, PALM HARBOR, FL, 34685
Community: Anchorage
Summertree 11805 LOBLOLLY PINE DR, NEW PORT RICHEY,..., New Port Richey, FL 34654
$259,900

2 beds

|

2 baths

|

1,223 sq ft

|

House

11805 LOBLOLLY PINE DR, NEW PORT RICHEY,...
Community: Summertree
Timber Greens 9500 GREEN NEEDLE DR, NEW PORT RICHEY, F..., New Port Richey, FL 34655
$349,000

2 beds

|

2 baths

|

1,213 sq ft

|

House

9500 GREEN NEEDLE DR, NEW PORT RICHEY, F...
Community: Timber Greens
Highland Lakes on Lake Tarpon 3430 STONEHAVEN CT D, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$249,500

2 beds

|

2 baths

|

1,230 sq ft

|

Villa

3430 STONEHAVEN CT D, PALM HARBOR, FL, 3...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Highland Lakes on Lake Tarpon 1350 GLENGARRY DR, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$495,000

2 beds

|

2 baths

|

1,694 sq ft

|

House

1350 GLENGARRY DR, PALM HARBOR, FL, 3468...
Heritage Lake 4719 CAVENDISH DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$298,900

2 beds

|

2 baths

|

1,646 sq ft

|

House

4719 CAVENDISH DR, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
1234567…8

Frequently Asked Questions


Want more information about active adult communities around Holiday?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
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
292 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

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: Jan 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top