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Holiday, FL 55+ active adult communities & homes for sale
28 communities near Holiday
303 homes near Holiday
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5 rating (1 reviews)
![Highland Lakes on Lake Ta...]()
$100ks
- $400ks
Highland Lakes on Lake Ta..., Palm Harbor, FL
Resale Only
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55+ age-restricted
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Built 1977 - 1989
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2,454 homes
5 rating (1 reviews)
![Timber Oaks]()
<$100k
- $200ks
Timber Oaks, Port Richey, FL
Resale Only
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55+ age-restricted
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Built 1973 - 1997
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1,000 homes
$100ks
- $200ks
Heritage Lake, New Port Richey, FL
Resale Only
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55+ age-restricted
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Built 1981 - 1994
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932 homes
3.5 rating (2 reviews)
![Timber Greens]()
$200ks
- $300ks
Timber Greens, New Port Richey, FL
Resale Only
|
55+ age-restricted
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Built 1994 - 2004
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783 homes
$200ks
- $300ks
Summertree, New Port Richey, FL
Resale Only
|
55+ age-restricted
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Built 1974 - 2015
|
800 homes
Want to learn more about 55+ communities in Holiday?
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4.7 rating (13 reviews)
![Heritage Springs]()
$200ks
- $500ks
Heritage Springs, Trinity, FL
Resale Only
|
55+ age-restricted
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Built 1999 - 2006
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1,337 homes
$100ks
Heather Lake Condominiums, Dunedin, FL
Resale Only
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55+ age-restricted
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Built 1972 - 1978
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200 homes
3.3 rating (3 reviews)
![Royal Stewart Arms]()
$100ks
- $300ks
Royal Stewart Arms, Dunedin, FL
Resale Only
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55+ age-restricted
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Built 1968 - 1975
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449 homes
2 rating (1 reviews)
![Beacon Lakes]()
$100ks
Beacon Lakes, New Port Richey, FL
Resale Only
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55+ age-restricted
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Built 1975 - 1982
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210 homes
$300ks
- $700ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only
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Age-targeted
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Built 2016 - 2022
|
517 homes
Download the Ultimate 55+ Homebuying Guide
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5 rating (2 reviews)
![Pine Ridge at Palm Harbor]()
$100ks
- $200ks
Pine Ridge at Palm Harbor, Palm Harbor, FL
Resale Only
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55+ age-restricted
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Built 1983 - 1983
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264 homes
5 rating (1 reviews)
![Village on the Green]()
$100ks
- $200ks
Village on the Green, Clearwater, FL
Resale Only
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55+ age-restricted
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Built 1978 - 1981
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448 homes
$100ks
Green Dolphin, Tarpon Springs, FL
Resale Only
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55+ age-restricted
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Built 1974 - 1990
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315 homes
$400ks
- $600ks
Edgewater Arms, Dunedin, FL
Resale Only
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55+ age-restricted
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Built 1970 - 1974
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209 homes
$100ks
Pinehurst Village, Dunedin, FL
Resale Only
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55+ age-restricted
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Built 1973 - 1976
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240 homes
$100ks
Briar Patch, New Port Richey, FL
Resale Only
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55+ age-restricted
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Built 1986 - 1993
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198 homes
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$800ks
- $1Ms
Victoria Lakes, Odessa, FL
New Construction
|
Age-targeted
|
Built 2025 - present
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166 homes
$100ks
Patrician Oaks, Dunedin, FL
Resale Only
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55+ age-restricted
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Built 1975 - 1982
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120 homes
$200ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only
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55+ age-restricted
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Built 1980 - 1983
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148 homes
$100ks
- $200ks
Imperial Pines Condominiu..., Clearwater, FL
Resale Only
|
55+ age-restricted
|
Built 1985 - 1985
|
181 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.
$100ks
Heather Hills Villas, Dunedin, FL
Resale Only
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55+ age-restricted
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Built 1971 - 1976
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64 homes
$200ks
- $300ks
Anchorage, Palm Harbor, FL
Resale Only
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55+ age-restricted
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Built 1972 - 1979
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279 homes
$100ks
Country Oaks, Hudson, FL
Resale Only
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55+ age-restricted
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Built 1981 - 1986
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42 homes
$200ks
Linkside Village, Port Richey, FL
Resale Only
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55+ age-restricted
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Built 1981 - 1985
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100 homes
$200ks
- $500ks
New Port Corners, New Port Richey, FL
New Construction
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55+ age-restricted
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Built 2025 - present
$300ks
Key Vista Villas, Holiday, FL
Resale Only
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55+ age-restricted
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Built 2001 - 2005
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170 homes
$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?
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Questions? Call us:
(727) 800-3371
$100ks
- $200ks
Heather Ridge, Dunedin, FL
Resale Only
|
55+ age-restricted
|
Built 1978 - 1987
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273 homes
Village on the Green
![2543 ROYAL PINES CIR 17K, CLEARWATER, FL..., Clearwater, FL 33763]()
2 beds
|2 baths
|1,030 sq ft
|Condo
2543 ROYAL PINES CIR 17K, CLEARWATER, FL...
Community: Village on the Green
MLS TB8543069 • PREMIER SOTHEBYS INTL REALTY, Jul... • PREMIER SOTHEBYS INTL REALTY
Heritage Lake
![4903 LEYTE CT 67, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,135 sq ft
|Condo
4903 LEYTE CT 67, NEW PORT RICHEY, FL, 3...
Community: Heritage Lake
MLS W7886892 • RE/MAX CHAMPIONS, Ashley Quaife • RE/MAX CHAMPIONS
New
Heritage Springs
![12027 FERN TERRACE CT, TRINITY, FL, 3465..., Trinity, FL 34655]()
3 beds
|2 baths
|1,683 sq ft
|House
12027 FERN TERRACE CT, TRINITY, FL, 3465...
Community: Heritage Springs
MLS W7889082 • FUTURE HOME REALTY, Justine Manous... • FUTURE HOME REALTY
New
![12342 OCONEE BLVD, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34654]()
Cindy Certified
New
Highland Lakes on Lake Tarpon
![2950 CURLING CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|978 sq ft
|House
2950 CURLING CT, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8545380 • RE/MAX ALLIANCE GROUP, Lawrence M... • RE/MAX ALLIANCE GROUP
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New
Highland Lakes on Lake Tarpon
![1139 ORANGE TREE CIR A, PALM HARBOR, FL,..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|960 sq ft
|Villa
1139 ORANGE TREE CIR A, PALM HARBOR, FL,...
Community: Highland Lakes on Lake Tarpon
MLS TB8537188 • RE/MAX CHAMPIONS, Rachel Mayhew • RE/MAX CHAMPIONS
New
Highland Lakes on Lake Tarpon
![2336 MALCOLM DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,288 sq ft
|House
2336 MALCOLM DR, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8543762 • COLDWELL BANKER REALTY, Amanda Ju... • COLDWELL BANKER REALTY
New
Pine Ridge at Palm Harbor
![1700 PINE RIDGE WAY C1, PALM HARBOR, FL,..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,038 sq ft
|Condo
1700 PINE RIDGE WAY C1, PALM HARBOR, FL,...
Community: Pine Ridge at Palm Harbor
MLS TB8546308 • COASTAL PROPERTIES GROUP INTERNAT... • COASTAL PROPERTIES GROUP INTERNATIONAL
Highland Lakes on Lake Tarpon
![945 MADRID DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|980 sq ft
|Villa
945 MADRID DR, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS W7889207 • KELLER WILLIAMS REALTY- PALM HARBO... • KELLER WILLIAMS REALTY- PALM HARBOR
Timber Greens
![9338 WHISPERING MEADOW CT, NEW PORT RICH..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,679 sq ft
|House
9338 WHISPERING MEADOW CT, NEW PORT RICH...
Community: Timber Greens
MLS A4705204 • JOSEPH WALTER REALTY LLC, Scott Fa... • JOSEPH WALTER REALTY LLC
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.
Timber Oaks
![11121 ROLLINGWOOD DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,554 sq ft
|House
11121 ROLLINGWOOD DR, PORT RICHEY, FL, 3...
Community: Timber Oaks
MLS W7889231 • HOME LAND REAL ESTATE INC, Brittan... • HOME LAND REAL ESTATE INC
Imperial Pines Condominiums
![3078 EASTLAND BLVD 209, CLEARWATER, FL, ..., Clearwater, FL 33761]()
2 beds
|2 baths
|1,390 sq ft
|Condo
3078 EASTLAND BLVD 209, CLEARWATER, FL, ...
Community: Imperial Pines Condominiums
MLS TB8545175 • FUTURE HOME REALTY INC, Michael L... • FUTURE HOME REALTY INC
Timber Oaks
![11541 SAN REMO CT, PORT RICHEY, FL, 3466..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,085 sq ft
|Condo
11541 SAN REMO CT, PORT RICHEY, FL, 3466...
Community: Timber Oaks
MLS TB8545091 • CHARLES RUTENBERG REALTY INC, Ste... • CHARLES RUTENBERG REALTY INC
Cindy Certified
Village on the Green
![2502 ROYAL PINES CIR 5C, CLEARWATER, FL,..., Clearwater, FL 33763]()
2 beds
|2 baths
|1,095 sq ft
|Condo
2502 ROYAL PINES CIR 5C, CLEARWATER, FL,...
Community: Village on the Green
MLS TB8537523 • SMITH & ASSOCIATES REAL ESTATE, R... • SMITH & ASSOCIATES REAL ESTATE
Highland Lakes on Lake Tarpon
![1652 HIGHLAND CLUB LN, PALM HARBOR, FL, ..., Palm Harbor, FL 34684]()
1 beds
|2 baths
|700 sq ft
|Villa
1652 HIGHLAND CLUB LN, PALM HARBOR, FL, ...
Community: Highland Lakes on Lake Tarpon
MLS TB8545125 • MARK SPAIN REAL ESTATE, Dee Kouli... • MARK SPAIN REAL ESTATE
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Questions? Call us:
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Summertree
![11440 GOLF ROUND DR, NEW PORT RICHEY, FL..., New Port Richey, FL 34654]()
3 beds
|2 baths
|1,719 sq ft
|Villa
11440 GOLF ROUND DR, NEW PORT RICHEY, FL...
Community: Summertree
MLS W7889058 • BHHS FLORIDA PROPERTIES GROUP, Rob... • BHHS FLORIDA PROPERTIES GROUP
Timber Oaks
![8521 CEDARVIEW CT, PORT RICHEY, FL, 3466..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,472 sq ft
|House
8521 CEDARVIEW CT, PORT RICHEY, FL, 3466...
Community: Timber Oaks
MLS TB8544689 • MARK SPAIN REAL ESTATE, Patrick M... • MARK SPAIN REAL ESTATE
Highland Lakes on Lake Tarpon
![1630 BYRNEDALE CT, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,248 sq ft
|House
1630 BYRNEDALE CT, PALM HARBOR, FL, 3468...
Community: Highland Lakes on Lake Tarpon
MLS W7889125 • VERANDA REALTY GROUP, Tina Hoover • VERANDA REALTY GROUP
Esplanade at Starkey Ranch
![11386 JUGLANS DR, ODESSA, FL, 33556, Odessa, FL 33556]()
3 beds
|3 baths
|2,140 sq ft
|House
11386 JUGLANS DR, ODESSA, FL, 33556
Community: Esplanade at Starkey Ranch
MLS TB8543629 • CHARLES RUTENBERG REALTY INC, Ali... • CHARLES RUTENBERG REALTY INC
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
![3558 OAK LAKE DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
3 beds
|2 baths
|2,154 sq ft
|House
3558 OAK LAKE DR, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8543377 • COLDWELL BANKER REALTY, Julie Kel... • COLDWELL BANKER REALTY
Highland Lakes on Lake Tarpon
![1609 WHITEBRIDGE DR A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,000 sq ft
|Condo
1609 WHITEBRIDGE DR A, PALM HARBOR, FL, ...
Community: Highland Lakes on Lake Tarpon
MLS TB8543982 • BHHS FLORIDA PROPERTIES GROUP, Ke... • BHHS FLORIDA PROPERTIES GROUP
Heritage Springs
![1004 SWEET JASMINE DR, TRINITY, FL, 3465..., Trinity, FL 34655]()
3 beds
|2 baths
|1,950 sq ft
|House
1004 SWEET JASMINE DR, TRINITY, FL, 3465...
Community: Heritage Springs
MLS W7888882 • FUTURE HOME REALTY, Justine Manous... • FUTURE HOME REALTY
Timber Greens
![9423 SUMMERBREEZE TER, NEW PORT RICHEY, ..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,808 sq ft
|House
9423 SUMMERBREEZE TER, NEW PORT RICHEY, ...
Community: Timber Greens
MLS W7889036 • RE/MAX MARKETING SPECIALISTS, Debo... • RE/MAX MARKETING SPECIALISTS
Pinehurst Village
![1701 PINEHURST RD 2F, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
1 beds
|1 baths
|645 sq ft
|Condo
1701 PINEHURST RD 2F, DUNEDIN, FL, 34698
Community: Pinehurst Village
MLS TB8543726 • DUNEDIN LIFE REALTY, David Vose • DUNEDIN LIFE REALTY
Village on the Green
![2529 OAKLEAF LN 30C, CLEARWATER, FL, 337..., Clearwater, FL 33763]()
2 beds
|2 baths
|960 sq ft
|Villa
2529 OAKLEAF LN 30C, CLEARWATER, FL, 337...
Community: Village on the Green
MLS TB8543365 • CHARLES RUTENBERG REALTY INC, Kar... • CHARLES RUTENBERG REALTY INC
Scotsdale Cluster Condominiums
![1251 SUTHERLAND CT, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|2 baths
|1,110 sq ft
|Condo
1251 SUTHERLAND CT, DUNEDIN, FL, 34698
Community: Scotsdale Cluster Condominiums
MLS TB8542460 • COASTAL PROPERTIES GROUP INTERNAT... • COASTAL PROPERTIES GROUP INTERNATIONAL
Want to learn more about 55+ communities in Holiday?
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Questions? Call us:
(727) 800-3371
Summertree
![11510 PAMPAS DR, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34654]()
2 beds
|2 baths
|1,384 sq ft
|House
11510 PAMPAS DR, NEW PORT RICHEY, FL, 34...
Community: Summertree
MLS L4964656 • KELLER WILLIAMS REALTY, Chad Karr • KELLER WILLIAMS REALTY
Highland Lakes on Lake Tarpon
![3300 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,332 sq ft
|Villa
3300 MCMATH DR, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8543424 • COLDWELL BANKER REALTY, Amanda Ju... • COLDWELL BANKER REALTY
Timber Oaks
![8045 PASADENA DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668]()
2 beds
|2 baths
|1,422 sq ft
|House
8045 PASADENA DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
MLS TB8542217 • RE/MAX CHAMPIONS, Nik Slavik • RE/MAX CHAMPIONS
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.
Heritage Lake
![4911 CATHEDRAL CT, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,266 sq ft
|Condo
4911 CATHEDRAL CT, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
MLS W7888854 • BHHS FLORIDA PROPERTIES GROUP, Kat... • BHHS FLORIDA PROPERTIES GROUP
Timber Oaks
![8643 GOLD PINE DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,470 sq ft
|House
8643 GOLD PINE DR, PORT RICHEY, FL, 3466...
Community: Timber Oaks
MLS TB8543358 • QUICKSILVER REAL ESTATE GROUP, Dy... • QUICKSILVER REAL ESTATE GROUP
Timber Oaks
![10811 PEPPERTREE LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,470 sq ft
|House
10811 PEPPERTREE LN, PORT RICHEY, FL, 34...
Community: Timber Oaks
MLS TB8542520 • REAL BROKER, LLC, David Ramos • REAL BROKER, LLC
Timber Greens
![6513 CARDINAL CREST DR, NEW PORT RICHEY,..., New Port Richey, FL 34655]()
3 beds
|2 baths
|2,015 sq ft
|House
6513 CARDINAL CREST DR, NEW PORT RICHEY,...
Community: Timber Greens
MLS TB8542374 • VERANDA REALTY GROUP, Laura Allim... • VERANDA REALTY GROUP
Beacon Lakes
![4034 DAVIT DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34652]()
2 beds
|2 baths
|1,144 sq ft
|Condo
4034 DAVIT DR, NEW PORT RICHEY, FL, 3465...
Community: Beacon Lakes
MLS B26069119 • LPT Realty, LLC, Rose Emilione • LPT Realty, LLC
Royal Stewart Arms
![9 FORBES PL 507, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
1 beds
|1 baths
|802 sq ft
|Condo
9 FORBES PL 507, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
MLS TB8518660 • RE/MAX REALTEC GROUP INC, Ed Karl... • RE/MAX REALTEC GROUP INC
Cindy Certified
Summertree
![12126 TOURNAMENT VIEW AVE, NEW PORT RICH..., New Port Richey, FL 34654]()
3 beds
|2 baths
|1,518 sq ft
|Villa
12126 TOURNAMENT VIEW AVE, NEW PORT RICH...
Community: Summertree
MLS TB8542743 • ORCHARD BROKERAGE, LLC, Christine... • ORCHARD BROKERAGE, LLC
Want to learn more about 55+ communities in Holiday?
55places can help!
Questions? Call us:
(727) 800-3371
Heritage Springs
![1017 SWEET JASMINE DR, TRINITY, FL, 3465..., Trinity, FL 34655]()
3 beds
|2 baths
|1,954 sq ft
|House
1017 SWEET JASMINE DR, TRINITY, FL, 3465...
Community: Heritage Springs
MLS W7888694 • RE/MAX CHAMPIONS, Gwen Zierke • RE/MAX CHAMPIONS
Highland Lakes on Lake Tarpon
![2360 SHELLY DR B, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|918 sq ft
|Condo
2360 SHELLY DR B, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8542922 • VINTAGE HOMES REALTY, Michelle Ja... • VINTAGE HOMES REALTY
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.
Frequently Asked Questions
In Holiday, there is 1 small community with less than 500 homes.
The smallest 55+ community in Holiday has 170 homes, the largest has 170 homes, and the average community consists of 170 homes.
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.
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.
Want more information about active adult communities around Holiday?
Want to learn more about 55+ communities in Holiday?
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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: Sep 11, 2026.
This application does not include information on all of the properties available for sale at this time.
