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

27 communities 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

Summertree

$200ks - $300ks

Summertree, New Port Richey, FL

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

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

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

Questions? Call us: (727) 800-3371

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

Heather Lake Condominiums

$100ks

Heather Lake Condominiums, Dunedin, FL

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

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

Esplanade at Starkey Ranc...

$300ks - $700ks

Esplanade at Starkey Ranc..., Odessa, FL

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

Green Dolphin

$100ks

Green Dolphin, Tarpon Springs, FL

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

Key Vista Villas

$300ks

Key Vista Villas, Holiday, FL

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

Briar Patch

$100ks

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

Edgewater Arms

$400ks - $600ks

Edgewater Arms, Dunedin, FL

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

Pinehurst Village

$100ks

Pinehurst Village, Dunedin, FL

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

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

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

Patrician Oaks

$100ks

Patrician Oaks, Dunedin, FL

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

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

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

Questions? Call us: (727) 800-3371

New Beacon Lakes

3815 PENRICK DR, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34652

$109,900

2 beds

2 baths

1,144 sq ft

Condo

3815 PENRICK DR, NEW PORT RICHEY, FL, 34...

Community: Beacon Lakes

New Heather Hills Villas

859 OXFORD CT, DUNEDIN, FL, 34698, Dunedin, FL 34698

$159,900

1 beds

1 baths

754 sq ft

Villa

859 OXFORD CT, DUNEDIN, FL, 34698

Community: Heather Hills Villas

New Highland Lakes on Lake Tarpon

1637 CALEDONIA DR, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684

$450,000

2 beds

2 baths

1,628 sq ft

House

1637 CALEDONIA DR, PALM HARBOR, FL, 3468...

Community: Highland Lakes on Lake Tarpon

New Esplanade at Starkey Ranch

11318 JUGLANS DR, ODESSA, FL, 33556, Odessa, FL 33556

$720,000

3 beds

3 baths

2,262 sq ft

House

11318 JUGLANS DR, ODESSA, FL, 33556

Community: Esplanade at Starkey Ranch

New Highland Lakes on Lake Tarpon

2150 SHELLY DR B, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$200,000

2 beds

2 baths

918 sq ft

Condo

2150 SHELLY DR B, 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

New Timber Oaks

10823 CASA GRANDE AVE, PORT RICHEY, FL, ..., Port Richey, FL 34668

$245,000

2 beds

2 baths

1,030 sq ft

House

10823 CASA GRANDE AVE, PORT RICHEY, FL, ...

Community: Timber Oaks

New Highland Lakes on Lake Tarpon

944 MADRID DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$239,900

1 beds

1 baths

700 sq ft

Villa

944 MADRID DR, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

New Timber Oaks

10501 HARDWOOD CT, PORT RICHEY, FL, 3466..., Port Richey, FL 34668

$295,000

3 beds

2 baths

1,422 sq ft

House

10501 HARDWOOD CT, PORT RICHEY, FL, 3466...

Community: Timber Oaks

New Timber Oaks

10616 SPRINGWOOD DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668

$225,000

2 beds

2 baths

1,112 sq ft

House

10616 SPRINGWOOD DR, PORT RICHEY, FL, 34...

Community: Timber Oaks

New Timber Greens

6019 COUNTRY RIDGE LN, NEW PORT RICHEY, ..., New Port Richey, FL 34655

$359,000

3 beds

2 baths

2,168 sq ft

House

6019 COUNTRY RIDGE LN, NEW PORT RICHEY, ...

Community: Timber Greens

New Patrician Oaks

845 MAPLE CT 103, DUNEDIN, FL, 34698, Dunedin, FL 34698

$149,900

2 beds

1 baths

1,004 sq ft

Condo

845 MAPLE CT 103, DUNEDIN, FL, 34698

Community: Patrician Oaks

New Summertree

11337 CLEAR OAK CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34654

$325,000

3 beds

2 baths

1,732 sq ft

House

11337 CLEAR OAK CIR, NEW PORT RICHEY, FL...

Community: Summertree

New Heather Lake Condominiums

952 VIRGINIA ST 209, DUNEDIN, FL, 34698, Dunedin, FL 34698

$129,000

1 beds

1 baths

800 sq ft

Condo

952 VIRGINIA ST 209, DUNEDIN, FL, 34698

Community: Heather Lake Condominiums

New Heather Lake Condominiums

936 VIRGINIA ST 206, DUNEDIN, FL, 34698, Dunedin, FL 34698

$150,000

2 beds

2 baths

927 sq ft

Condo

936 VIRGINIA ST 206, DUNEDIN, FL, 34698

Community: Heather Lake Condominiums

New Highland Lakes on Lake Tarpon

1060 DUNROBIN DR A, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684

$249,900

2 beds

2 baths

1,230 sq ft

Villa

1060 DUNROBIN DR A, PALM HARBOR, FL, 346...

Community: Highland Lakes on Lake Tarpon

New Green Dolphin

1250 S PINELLAS AVE 205, TARPON SPRINGS,..., Tarpon Springs, FL 34689

$134,000

1 beds

1 baths

669 sq ft

Condo

1250 S PINELLAS AVE 205, TARPON SPRINGS,...

Community: Green Dolphin

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

Questions? Call us: (727) 800-3371

New Village on the Green

2210 SEQUOIA DR, CLEARWATER, FL, 33763, Clearwater, FL 33763

$339,000

2 beds

2 baths

1,309 sq ft

House

2210 SEQUOIA DR, CLEARWATER, FL, 33763

Community: Village on the Green

New Highland Lakes on Lake Tarpon

2238 LARK CIR D, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684

$199,000

2 beds

2 baths

1,230 sq ft

Condo

2238 LARK CIR D, PALM HARBOR, FL, 34684

Community: Highland Lakes on Lake Tarpon

New Royal Stewart Arms

2 CAUSEWAY BLVD 208, DUNEDIN, FL, 34698, Dunedin, FL 34698

$360,000

2 beds

2 baths

1,123 sq ft

Condo

2 CAUSEWAY BLVD 208, DUNEDIN, FL, 34698

Community: Royal Stewart Arms

Timber Greens

6542 PINE WALK DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655

$299,000

2 beds

2 baths

1,549 sq ft

Villa

6542 PINE WALK DR, NEW PORT RICHEY, FL, ...

Community: Timber Greens

Pine Ridge at Palm Harbor

2688 PINE RIDGE WAY A2, PALM HARBOR, FL,..., Palm Harbor, FL 34684

$184,900

2 beds

2 baths

1,038 sq ft

Condo

2688 PINE RIDGE WAY A2, PALM HARBOR, FL,...

Community: Pine Ridge at Palm Harbor

Imperial Pines Condominiums

3076 EASTLAND BLVD 203, CLEARWATER, FL, ..., Clearwater, FL 33761

$160,000

2 beds

2 baths

1,250 sq ft

Condo

3076 EASTLAND BLVD 203, CLEARWATER, FL, ...

Community: Imperial Pines Condominiums

Esplanade at Starkey Ranch

11257 CALLISIA DR, ODESSA, FL, 33556, Odessa, FL 33556

$540,000

3 beds

2 baths

1,931 sq ft

House

11257 CALLISIA DR, ODESSA, FL, 33556

Community: Esplanade at Starkey Ranch

Heritage Lake

9427 CAPE CHARLES AVE, NEW PORT RICHEY, ..., New Port Richey, FL 34655

$215,000

2 beds

2 baths

1,016 sq ft

House

9427 CAPE CHARLES AVE, NEW PORT RICHEY, ...

Community: Heritage Lake

Heather Lake Condominiums

952 VIRGINIA ST 202, DUNEDIN, FL, 34698, Dunedin, FL 34698

$218,000

2 beds

2 baths

965 sq ft

Condo

952 VIRGINIA ST 202, DUNEDIN, FL, 34698

Community: Heather Lake Condominiums

Timber Oaks

8119 SAN BERNARDINO DR, PORT RICHEY, FL,..., Port Richey, FL 34668

$276,000

3 beds

2 baths

1,784 sq ft

House

8119 SAN BERNARDINO DR, PORT RICHEY, FL,...

Community: Timber Oaks

Esplanade at Starkey Ranch

11257 EGERIA DR, ODESSA, FL, 33556, Odessa, FL 33556

$749,900

3 beds

4 baths

2,740 sq ft

House

11257 EGERIA DR, ODESSA, FL, 33556

Community: Esplanade at Starkey Ranch

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

Questions? Call us: (727) 800-3371

Anchorage

$459,900

3 beds

2 baths

1,822 sq ft

House

835 ANCHORAGE LN, PALM HARBOR, FL, 34685

Community: Anchorage

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

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

Heather Ridge

$149,900

2 beds

1 baths

990 sq ft

Condo

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

Community: Heather Ridge

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

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

Heritage Springs

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

$373,000

2 beds

2 baths

1,900 sq ft

Villa

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

Community: Heritage Springs

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

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

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

Highland Lakes on Lake Tarpon

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

$212,980

2 beds

2 baths

1,120 sq ft

Condo

2291 SHELLY DR D, 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

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

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

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

27 communities

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 24, 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

296 homes near Holiday

2 beds

2 baths

1,144 sq ft

Condo

1 beds

1 baths

754 sq ft

Villa

2 beds

2 baths

1,628 sq ft

House

3 beds

3 baths

2,262 sq ft

House

2 beds

2 baths

918 sq ft

Condo

2 beds

2 baths

1,030 sq ft

House

1 beds

1 baths

700 sq ft

Villa

3 beds

2 baths

1,422 sq ft

House

2 beds

2 baths

1,112 sq ft

House

3 beds

2 baths

2,168 sq ft

House

2 beds

1 baths

1,004 sq ft

Condo

3 beds

2 baths

1,732 sq ft

House

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

927 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Villa

1 beds

1 baths

669 sq ft

Condo

2 beds

2 baths

1,309 sq ft

House

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,123 sq ft

Condo

2 beds