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Holiday, FL 55+ active adult communities & homes for sale - Page 6

292 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
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
Summertree
$200ks - $300ks
Summertree, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1974 - 2015 | 800 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
4.7 rating (13 reviews) Heritage Springs
$200ks - $500ks
Heritage Springs, Trinity, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,337 homes
Heather Lake Condominiums
$100ks
Heather Lake Condominiums, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 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
Green Dolphin
$100ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 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.
5 rating (2 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
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
$400ks - $600ks
Edgewater Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 homes
Victoria Lakes
$800ks - $1Ms
Victoria Lakes, Odessa, FL
New Construction | Age-targeted | Built 2025 - present | 166 homes
Briar Patch
$100ks
Briar Patch, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 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
Key Vista Villas
$300ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 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
Imperial Pines Condominiu...
$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.
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
Country Oaks
$100ks
Country Oaks, Hudson, FL
Resale Only | 55+ age-restricted | Built 1981 - 1986 | 42 homes
Linkside Village
$200ks
Linkside Village, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 100 homes
New Port Corners
$200ks - $500ks
New Port Corners, New Port Richey, FL
New Construction | 55+ age-restricted | Built 2025 - present
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
Heather Ridge
$100ks - $200ks
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
Soleta at Starkey Ranch
$500ks - $600ks
Soleta at Starkey Ranch, Odessa, FL
New Construction | Age-targeted | Built 2023 - present | 139 homes
Heritage Lake 4643 SANDPOINTE DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$310,000

3 beds

|

2 baths

|

1,708 sq ft

|

House

4643 SANDPOINTE DR, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Summertree 11622 COCOWOOD DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34654
$244,000

3 beds

|

2 baths

|

1,349 sq ft

|

House

11622 COCOWOOD DR, NEW PORT RICHEY, FL, ...
Community: Summertree
Timber Greens 9307 PALM HAVEN CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$384,000

2 beds

|

2 baths

|

1,642 sq ft

|

Villa

9307 PALM HAVEN CT, NEW PORT RICHEY, FL,...
Community: Timber Greens
Heritage Springs 11428 HIDDEN COVE CT, TRINITY, FL, 34655, Trinity, FL 34655
$425,000

3 beds

|

2 baths

|

1,799 sq ft

|

House

11428 HIDDEN COVE CT, TRINITY, FL, 34655
Community: Heritage Springs
Beacon Lakes 3815 PENRICK DR, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34652
$90,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

3815 PENRICK DR, NEW PORT RICHEY, FL, 34...
Community: Beacon Lakes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Cindy Certified
2713 SAN LUIS RD, HOLIDAY, FL, 34691, Holiday, FL 34691
$420,000

3 beds

|

2 baths

|

1,460 sq ft

|

House

2713 SAN LUIS RD, HOLIDAY, FL, 34691
Timber Oaks 10501 HARDWOOD CT, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$289,900

3 beds

|

2 baths

|

1,422 sq ft

|

House

10501 HARDWOOD CT, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Timber Oaks 10616 SPRINGWOOD DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$220,000

2 beds

|

2 baths

|

1,112 sq ft

|

House

10616 SPRINGWOOD DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Patrician Oaks 845 MAPLE CT 103, DUNEDIN, FL, 34698, Dunedin, FL 34698
$139,900

2 beds

|

1 baths

|

1,004 sq ft

|

Condo

845 MAPLE CT 103, DUNEDIN, FL, 34698
Community: Patrician Oaks
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
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 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
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,...
Heather Lake Condominiums 952 VIRGINIA ST 202, DUNEDIN, FL, 34698, Dunedin, FL 34698
$189,999

2 beds

|

2 baths

|

965 sq ft

|

Condo

952 VIRGINIA ST 202, DUNEDIN, FL, 34698
Cindy Certified
6671 MINERAL SPRINGS RD, NEW PORT RICHEY..., New Port Richey, FL 34653
$339,000

3 beds

|

2 baths

|

1,561 sq ft

|

House

6671 MINERAL SPRINGS RD, NEW PORT RICHEY...
Heritage Springs 1933 ARBOR KNOLL LOOP, TRINITY, FL, 3465..., Trinity, FL 34655
$350,000

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
$315,000

3 beds

|

2 baths

|

1,854 sq ft

|

House

11303 CLEAR OAK CIR, NEW PORT RICHEY, FL...
Community: Summertree
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Imperial Pines Condominiums 3078 EASTLAND BLVD 309, CLEARWATER, FL, ..., Clearwater, FL 33761
$235,000

3 beds

|

2 baths

|

1,390 sq ft

|

Condo

3078 EASTLAND BLVD 309, CLEARWATER, FL, ...
Victoria Lakes 11235 MANOR HOUSE LN, ODESSA, FL, 33556, Odessa, FL 33556
$1,051,433

4 beds

|

5 baths

|

2,921 sq ft

|

House

11235 MANOR HOUSE LN, ODESSA, FL, 33556
Community: Victoria Lakes
Victoria Lakes 16237 ALPHA GROVE PL, ODESSA, FL, 33556, Odessa, FL 33556
$1,347,429

6 beds

|

6 baths

|

4,271 sq ft

|

House

16237 ALPHA GROVE PL, ODESSA, FL, 33556
Community: Victoria Lakes
Timber Greens 6447 PINE WALK DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$305,000

2 beds

|

2 baths

|

1,352 sq ft

|

Villa

6447 PINE WALK DR, 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.
Victoria Lakes 11270 KINGLY LN, ODESSA, FL, 33556, Odessa, FL 33556
$1,390,316

6 beds

|

5 baths

|

4,181 sq ft

|

House

11270 KINGLY LN, ODESSA, FL, 33556
Community: Victoria Lakes
Victoria Lakes 11283 MANOR HOUSE LN, ODESSA, FL, 33556, Odessa, FL 33556
$1,029,694

4 beds

|

5 baths

|

2,921 sq ft

|

House

11283 MANOR HOUSE LN, ODESSA, FL, 33556
Community: Victoria Lakes
Cindy Certified
7994 CHANDLER LAKE CT 16, HUDSON, FL, 34..., Hudson, FL 34667
$328,884

3 beds

|

2 baths

|

1,472 sq ft

|

House

7994 CHANDLER LAKE CT 16, HUDSON, FL, 34...
Pine Ridge at Palm Harbor 2688 PINE RIDGE WAY D2, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$169,500

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

2688 PINE RIDGE WAY D2, PALM HARBOR, FL,...
Heritage Lake 4808 VESPER CT 34, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$169,000

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

4808 VESPER CT 34, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
Timber Oaks 11340 DOLLAR LAKE DR 2, PORT RICHEY, FL,..., Port Richey, FL 34668
$144,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

11340 DOLLAR LAKE DR 2, PORT RICHEY, FL,...
Community: Timber Oaks
Green Dolphin 1250 S PINELLAS AVE 804, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$78,900

1 beds

|

1 baths

|

565 sq ft

|

Condo

1250 S PINELLAS AVE 804, TARPON SPRINGS,...
Community: Green Dolphin
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Edgewater Arms 620 EDGEWATER DR 102, DUNEDIN, FL, 34698, Dunedin, FL 34698
$499,000

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

620 EDGEWATER DR 102, DUNEDIN, FL, 34698
Community: Edgewater Arms
Heritage Springs 1249 WINDING WILLOW DR, TRINITY, FL, 346..., Trinity, FL 34655
$325,000

3 beds

|

2 baths

|

1,773 sq ft

|

House

1249 WINDING WILLOW DR, TRINITY, FL, 346...
Community: Heritage Springs
Summertree 11442 TURTLE DOVE PL, NEW PORT RICHEY, F..., New Port Richey, FL 34654
$279,900

2 beds

|

2 baths

|

1,471 sq ft

|

House

11442 TURTLE DOVE PL, NEW PORT RICHEY, F...
Community: Summertree
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.
Royal Stewart Arms 7 DUNOON PL 102, DUNEDIN, FL, 34698, Dunedin, FL 34698
$270,000

1 beds

|

1 baths

|

957 sq ft

|

Condo

7 DUNOON PL 102, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Briar Patch 4505 GLEN HOLW, NEW PORT RICHEY, FL, 346..., New Port Richey, FL 34653
$215,000

2 beds

|

3 baths

|

1,453 sq ft

|

Townhouse

4505 GLEN HOLW, NEW PORT RICHEY, FL, 346...
Community: Briar Patch
Timber Oaks 11241 DOLLAR LAKE DR 4, PORT RICHEY, FL,..., Port Richey, FL 34668
$130,000

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

11241 DOLLAR LAKE DR 4, PORT RICHEY, FL,...
Community: Timber Oaks
Country Oaks 7804 EUREKA DR, HUDSON, FL, 34667, Hudson, FL 34667
$140,000

2 beds

|

2 baths

|

1,049 sq ft

|

Condo

7804 EUREKA DR, HUDSON, FL, 34667
Community: Country Oaks
Key Vista Villas 2211 PLEASANT HILL LN, HOLIDAY, FL, 3469..., Holiday, FL 34691
$300,000

2 beds

|

2 baths

|

1,500 sq ft

|

Villa

2211 PLEASANT HILL LN, HOLIDAY, FL, 3469...
Community: Key Vista Villas
Timber Greens 6353 CARDINAL CREST DR, NEW PORT RICHEY,..., New Port Richey, FL 34655
$369,000

3 beds

|

2 baths

|

1,709 sq ft

|

House

6353 CARDINAL CREST DR, NEW PORT RICHEY,...
Community: Timber Greens
Heather Hills Villas 852 OXFORD CT, DUNEDIN, FL, 34698, Dunedin, FL 34698
$214,900

2 beds

|

2 baths

|

999 sq ft

|

Villa

852 OXFORD CT, DUNEDIN, FL, 34698
Pinehurst Village 1701 PINEHURST RD 18C, DUNEDIN, FL, 3469..., Dunedin, FL 34698
$145,900

2 beds

|

1 baths

|

875 sq ft

|

Villa

1701 PINEHURST RD 18C, DUNEDIN, FL, 3469...
Community: Pinehurst Village
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Patrician Oaks 865 VIRGINIA CT 108, DUNEDIN, FL, 34698, Dunedin, FL 34698
$154,000

2 beds

|

2 baths

|

1,040 sq ft

|

Condo

865 VIRGINIA CT 108, DUNEDIN, FL, 34698
Community: Patrician Oaks
Highland Lakes on Lake Tarpon 3305 GORSE CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$339,000

2 beds

|

2 baths

|

1,148 sq ft

|

Villa

3305 GORSE CT, 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.
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