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

281 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 | 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
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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
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.
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
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.
Linkside Village
$200ks
Linkside Village, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 100 homes
Timber Greens 9625 OAKWOOD HILLS CT, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$359,900

2 beds

|

2 baths

|

1,820 sq ft

|

House

9625 OAKWOOD HILLS CT, NEW PORT RICHEY, ...
Community: Timber Greens
Heritage Lake 4705 LACROSSE CT, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34655
$235,000

2 beds

|

2 baths

|

1,326 sq ft

|

Villa

4705 LACROSSE CT, NEW PORT RICHEY, FL, 3...
Community: Heritage Lake
Scotsdale Cluster Condominiums 365 DURHAM CT, DUNEDIN, FL, 34698, Dunedin, FL 34698
$365,000

2 beds

|

2 baths

|

1,230 sq ft

|

Villa

365 DURHAM CT, DUNEDIN, FL, 34698
Beacon Lakes 4028 DAVIT DR # 4028, NEW PORT RICHEY, F..., New Port Richey, FL 34652
$190,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

4028 DAVIT DR # 4028, NEW PORT RICHEY, F...
Community: Beacon Lakes
Timber Oaks 11604 VERSAILLES LN 60, PORT RICHEY, FL,..., Port Richey, FL 34668
$229,000

3 beds

|

2 baths

|

1,239 sq ft

|

House

11604 VERSAILLES LN 60, PORT RICHEY, FL,...
Community: Timber Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Pine Ridge at Palm Harbor 1725 PINE RIDGE WAY C, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$285,000

2 beds

|

2 baths

|

1,350 sq ft

|

Villa

1725 PINE RIDGE WAY C, PALM HARBOR, FL, ...
Country Oaks 7737 EUREKA DR 203, HUDSON, FL, 34667, Hudson, FL 34667
$159,900

2 beds

|

2 baths

|

1,141 sq ft

|

Condo

7737 EUREKA DR 203, HUDSON, FL, 34667
Community: Country Oaks
Pine Ridge at Palm Harbor 2666 PINE RIDGE WAY C2, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$184,900

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

2666 PINE RIDGE WAY C2, PALM HARBOR, FL,...
Timber Greens 9326 PALM HAVEN CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$322,000

2 beds

|

2 baths

|

1,672 sq ft

|

Villa

9326 PALM HAVEN CT, NEW PORT RICHEY, FL,...
Community: Timber Greens
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 4749 WESTBURY CT, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34655
$219,900

2 beds

|

2 baths

|

1,340 sq ft

|

Condo

4749 WESTBURY CT, NEW PORT RICHEY, FL, 3...
Community: Heritage Lake
Timber Oaks 8708 BENTON DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$249,999

2 beds

|

2 baths

|

1,112 sq ft

|

House

8708 BENTON DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
Edgewater Arms 634 EDGEWATER DR 848, DUNEDIN, FL, 34698, Dunedin, FL 34698
$525,000

2 beds

|

2 baths

|

1,465 sq ft

|

Condo

634 EDGEWATER DR 848, DUNEDIN, FL, 34698
Community: Edgewater Arms
Edgewater Arms 634 EDGEWATER DR 744, DUNEDIN, FL, 34698, Dunedin, FL 34698
$1,060,000

3 beds

|

3 baths

|

2,330 sq ft

|

Condo

634 EDGEWATER DR 744, DUNEDIN, FL, 34698
Community: Edgewater Arms
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 8014 CASUARINA DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$239,000

3 beds

|

3 baths

|

1,650 sq ft

|

House

8014 CASUARINA DR, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Timber Oaks 11120 CARRIAGE HILL DR 1, PORT RICHEY, F..., Port Richey, FL 34668
$99,900

2 beds

|

2 baths

|

882 sq ft

|

Villa

11120 CARRIAGE HILL DR 1, PORT RICHEY, F...
Community: Timber Oaks
Pinehurst Village 1701 PINEHURST RD 9G, DUNEDIN, FL, 34698, Dunedin, FL 34698
$199,000

2 beds

|

2 baths

|

875 sq ft

|

Condo

1701 PINEHURST RD 9G, DUNEDIN, FL, 34698
Community: Pinehurst Village
Heritage Springs 11751 AINTREE CT, TRINITY, FL, 34655, Trinity, FL 34655
$369,900

3 beds

|

2 baths

|

1,806 sq ft

|

House

11751 AINTREE CT, TRINITY, FL, 34655
Community: Heritage Springs
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 1084 DUNROBIN DR D, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$274,000

2 beds

|

2 baths

|

1,230 sq ft

|

Villa

1084 DUNROBIN DR D, PALM HARBOR, FL, 346...
Briar Patch 4523 GLEN HOLW, NEW PORT RICHEY, FL, 346..., New Port Richey, FL 34653
$189,000

2 beds

|

2 baths

|

964 sq ft

|

House

4523 GLEN HOLW, NEW PORT RICHEY, FL, 346...
Community: Briar Patch
Royal Stewart Arms 9 HAIG PL 801, DUNEDIN, FL, 34698, Dunedin, FL 34698
$365,000

2 beds

|

2 baths

|

1,181 sq ft

|

Condo

9 HAIG PL 801, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Timber Oaks 10654 FALLEN LEAF LN, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$315,000

2 beds

|

2 baths

|

1,718 sq ft

|

House

10654 FALLEN LEAF LN, PORT RICHEY, FL, 3...
Community: Timber Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 8221 SULKY CT 1, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$184,900

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

8221 SULKY CT 1, PORT RICHEY, FL, 34668
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 10721 FOOTPRINT LN, PORT RICHEY, FL, 346..., Port Richey, FL 34668
$299,900

2 beds

|

2 baths

|

2,005 sq ft

|

House

10721 FOOTPRINT LN, PORT RICHEY, FL, 346...
Community: Timber Oaks
Beacon Lakes 4036 DAVIT DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34652
$170,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

4036 DAVIT DR, NEW PORT RICHEY, FL, 3465...
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.
Timber Greens 6045 COUNTRY RIDGE LN, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$359,000

3 beds

|

2 baths

|

2,042 sq ft

|

House

6045 COUNTRY RIDGE LN, NEW PORT RICHEY, ...
Community: Timber Greens
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
Heather Ridge 1375 DOOLITTLE LN 103, DUNEDIN, FL, 3469..., Dunedin, FL 34698
$149,000

2 beds

|

1 baths

|

990 sq ft

|

Condo

1375 DOOLITTLE LN 103, DUNEDIN, FL, 3469...
Community: Heather Ridge
Edgewater Arms 632 EDGEWATER DR 135, DUNEDIN, FL, 34698, Dunedin, FL 34698
$399,000

2 beds

|

2 baths

|

1,330 sq ft

|

Condo

632 EDGEWATER DR 135, DUNEDIN, FL, 34698
Community: Edgewater Arms
Edgewater Arms 634 EDGEWATER DR 849, DUNEDIN, FL, 34698, Dunedin, FL 34698
$599,000

2 beds

|

2 baths

|

1,630 sq ft

|

Condo

634 EDGEWATER DR 849, DUNEDIN, FL, 34698
Community: Edgewater Arms
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heritage Springs 1211 ALMONDWOOD DR, TRINITY, FL, 34655, Trinity, FL 34655
$315,000

2 beds

|

2 baths

|

1,592 sq ft

|

House

1211 ALMONDWOOD DR, TRINITY, FL, 34655
Community: Heritage Springs
Pine Ridge at Palm Harbor 2522 PINE RIDGE WAY A2, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$189,900

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

2522 PINE RIDGE WAY A2, PALM HARBOR, FL,...
Village on the Green 2617 SYCAMORE DR, CLEARWATER, FL, 33763, Clearwater, FL 33763
$290,000

2 beds

|

2 baths

|

1,313 sq ft

|

House

2617 SYCAMORE DR, CLEARWATER, FL, 33763
Highland Lakes on Lake Tarpon 3280 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$270,000

2 beds

|

2 baths

|

1,332 sq ft

|

Villa

3280 MCMATH DR, PALM HARBOR, FL, 34684
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 1603 WHITEBRIDGE DR D, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$158,900

1 beds

|

1 baths

|

814 sq ft

|

Condo

1603 WHITEBRIDGE DR D, PALM HARBOR, FL, ...
Timber Greens 9630 GREEN NEEDLE DR, NEW PORT RICHEY, F..., New Port Richey, FL 34655
$359,900

2 beds

|

2 baths

|

1,724 sq ft

|

House

9630 GREEN NEEDLE DR, NEW PORT RICHEY, F...
Community: Timber Greens
Highland Lakes on Lake Tarpon 2850 HIGHLANDS BLVD A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$170,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

2850 HIGHLANDS BLVD A, PALM HARBOR, FL, ...
Highland Lakes on Lake Tarpon 2137 MALCOLM DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$434,800

2 beds

|

2 baths

|

1,319 sq ft

|

House

2137 MALCOLM DR, PALM HARBOR, FL, 34684
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Highland Lakes on Lake Tarpon 2842 HIGHLANDS BLVD A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$225,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

2842 HIGHLANDS BLVD A, PALM HARBOR, FL, ...
Timber Oaks 11135 CARRIAGE HILL DR 3, PORT RICHEY, F..., Port Richey, FL 34668
$127,500

2 beds

|

2 baths

|

954 sq ft

|

Condo

11135 CARRIAGE HILL DR 3, PORT RICHEY, F...
Community: Timber Oaks
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