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

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 9500 GREEN NEEDLE DR, NEW PORT RICHEY, F..., New Port Richey, FL 34655
$336,500

2 beds

|

2 baths

|

1,213 sq ft

|

House

9500 GREEN NEEDLE DR, NEW PORT RICHEY, F...
Community: Timber Greens
Green Dolphin 1250 S PINELLAS AVE 506, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$88,500

1 beds

|

1 baths

|

669 sq ft

|

Condo

1250 S PINELLAS AVE 506, TARPON SPRINGS,...
Community: Green Dolphin
Summertree 12209 PUTTER GREEN CT, NEW PORT RICHEY, ..., New Port Richey, FL 34654
$281,900

2 beds

|

2 baths

|

1,414 sq ft

|

Villa

12209 PUTTER GREEN CT, NEW PORT RICHEY, ...
Community: Summertree
Imperial Pines Condominiums 3078 EASTLAND BLVD 107, CLEARWATER, FL, ..., Clearwater, FL 33761
$185,000

1 beds

|

1 baths

|

870 sq ft

|

Condo

3078 EASTLAND BLVD 107, CLEARWATER, FL, ...
Village on the Green 2561 ROYAL PINES CIR # 14H, CLEARWATER, ..., Clearwater, FL 33763
$196,000

2 beds

|

2 baths

|

1,095 sq ft

|

Condo

2561 ROYAL PINES CIR # 14H, CLEARWATER, ...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Edgewater Arms 632 EDGEWATER DR 238, DUNEDIN, FL, 34698, Dunedin, FL 34698
$370,000

2 beds

|

2 baths

|

1,220 sq ft

|

Condo

632 EDGEWATER DR 238, DUNEDIN, FL, 34698
Community: Edgewater Arms
Heritage Springs 1201 DUSTAN PL, TRINITY, FL, 34655, Trinity, FL 34655
$374,900

3 beds

|

2 baths

|

2,032 sq ft

|

House

1201 DUSTAN PL, TRINITY, FL, 34655
Community: Heritage Springs
Pinehurst Village 1701 PINEHURST RD 3E, DUNEDIN, FL, 34698, Dunedin, FL 34698
$137,000

1 beds

|

1 baths

|

645 sq ft

|

Condo

1701 PINEHURST RD 3E, DUNEDIN, FL, 34698
Community: Pinehurst Village
Green Dolphin 2201 PINE DR, TARPON SPRINGS, FL, 34689, Tarpon Springs, FL 34689
$267,000

2 beds

|

2 baths

|

1,320 sq ft

|

Villa

2201 PINE DR, TARPON SPRINGS, FL, 34689
Community: Green Dolphin
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 9 HAIG PL 104, DUNEDIN, FL, 34698, Dunedin, FL 34698
$299,900

2 beds

|

2 baths

|

975 sq ft

|

Condo

9 HAIG PL 104, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Timber Greens 6543 PINE WALK DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$325,000

2 beds

|

2 baths

|

1,380 sq ft

|

Villa

6543 PINE WALK DR, NEW PORT RICHEY, FL, ...
Community: Timber Greens
Highland Lakes on Lake Tarpon 3109 MISSION GROVE DR D, PALM HARBOR, FL..., Palm Harbor, FL 34684
$129,500

2 beds

|

2 baths

|

806 sq ft

|

Condo

3109 MISSION GROVE DR D, PALM HARBOR, FL...
Timber Oaks 11220 ELDERBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$246,999

2 beds

|

2 baths

|

1,347 sq ft

|

House

11220 ELDERBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heritage Lake 9309 TROWBRIDGE CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$185,000

1 beds

|

1 baths

|

723 sq ft

|

Villa

9309 TROWBRIDGE CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Highland Lakes on Lake Tarpon 2932 MACALPIN DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$418,500

2 beds

|

2 baths

|

1,539 sq ft

|

House

2932 MACALPIN DR, PALM HARBOR, FL, 34684
Esplanade at Starkey Ranch 11599 CALLISIA DR, ODESSA, FL, 33556, Odessa, FL 33556
$449,500

2 beds

|

2 baths

|

1,689 sq ft

|

House

11599 CALLISIA DR, ODESSA, FL, 33556
Green Dolphin 1933 GOLFVIEW DR # 1933, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$259,900

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

1933 GOLFVIEW DR # 1933, TARPON SPRINGS,...
Community: Green Dolphin
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 1609 WHITEBRIDGE DR C, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$149,400

1 beds

|

1 baths

|

964 sq ft

|

Condo

1609 WHITEBRIDGE DR C, PALM HARBOR, FL, ...
Highland Lakes on Lake Tarpon 1605 WHITEBRIDGE DR B, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$185,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1605 WHITEBRIDGE DR B, PALM HARBOR, FL, ...
Heather Lake Condominiums 821 PATRICIA AVE 202, DUNEDIN, FL, 34698, Dunedin, FL 34698
$159,900

2 beds

|

1 baths

|

935 sq ft

|

Condo

821 PATRICIA AVE 202, DUNEDIN, FL, 34698
Timber Oaks 11403 VERSAILLES LN E, PORT RICHEY, FL, ..., Port Richey, FL 34668
$149,000

2 beds

|

2 baths

|

1,171 sq ft

|

Condo

11403 VERSAILLES LN E, PORT RICHEY, FL, ...
Community: Timber Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 8130 MERRIMAC DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$274,900

2 beds

|

2 baths

|

1,470 sq ft

|

House

8130 MERRIMAC DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
Timber Oaks 11204 PEMBRIDGE CT 4, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$82,500

2 beds

|

2 baths

|

978 sq ft

|

Condo

11204 PEMBRIDGE CT 4, PORT RICHEY, FL, 3...
Community: Timber Oaks
Edgewater Arms 634 EDGEWATER DR 447, DUNEDIN, FL, 34698, Dunedin, FL 34698
$434,000

2 beds

|

2 baths

|

1,175 sq ft

|

Condo

634 EDGEWATER DR 447, DUNEDIN, FL, 34698
Community: Edgewater Arms
Heritage Lake 4740 CARRINGTON CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$237,000

2 beds

|

2 baths

|

1,340 sq ft

|

Condo

4740 CARRINGTON CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
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 208, DUNEDIN, FL, 34698, Dunedin, FL 34698
$139,500

2 beds

|

2 baths

|

1,010 sq ft

|

Condo

936 VIRGINIA ST 208, DUNEDIN, FL, 34698
Heritage Lake 4814 GRIST MILL CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$211,500

2 beds

|

2 baths

|

1,174 sq ft

|

Villa

4814 GRIST MILL CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
Green Dolphin 1250 S PINELLAS AVE 711, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$117,500

1 beds

|

1 baths

|

565 sq ft

|

Condo

1250 S PINELLAS AVE 711, TARPON SPRINGS,...
Community: Green Dolphin
Highland Lakes on Lake Tarpon 2846 HIGHLANDS BLVD D, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$185,000

1 beds

|

2 baths

|

814 sq ft

|

Condo

2846 HIGHLANDS BLVD D, PALM HARBOR, FL, ...
Green Dolphin 1250 S PINELLAS AVE 411, TARPON SPRINGS,..., Tarpon Springs, FL 34689
$115,000

1 beds

|

1 baths

|

565 sq ft

|

Condo

1250 S PINELLAS AVE 411, TARPON SPRINGS,...
Community: Green Dolphin
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Royal Stewart Arms 7 DUNOON PL APT 203, DUNEDIN, FL, 34698, Dunedin, FL 34698
$299,750

1 beds

|

1 baths

|

957 sq ft

|

Condo

7 DUNOON PL APT 203, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Key Vista Villas 2514 SANDY HILL CT, HOLIDAY, FL, 34691, Holiday, FL 34691
$345,900

2 beds

|

2 baths

|

1,555 sq ft

|

House

2514 SANDY HILL CT, HOLIDAY, FL, 34691
Community: Key Vista Villas
Timber Oaks 11241 VERSAILLES LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$159,900

2 beds

|

2 baths

|

1,037 sq ft

|

Condo

11241 VERSAILLES LN, PORT RICHEY, FL, 34...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 1472 QUEEN ANNE BLVD, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$445,000

2 beds

|

2 baths

|

1,211 sq ft

|

House

1472 QUEEN ANNE BLVD, PALM HARBOR, FL, 3...
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 2150 SHELLY DR A, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$204,999

2 beds

|

2 baths

|

918 sq ft

|

Condo

2150 SHELLY DR A, PALM HARBOR, FL, 34684
Timber Oaks 10800 TEER LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$235,000

2 beds

|

2 baths

|

1,522 sq ft

|

House

10800 TEER LN, PORT RICHEY, FL, 34668
Community: Timber Oaks
Heritage Lake 4739 CARRINGTON CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$210,000

2 beds

|

2 baths

|

1,261 sq ft

|

Condo

4739 CARRINGTON CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Timber Oaks 8111 BRADDOCK CIR 6, PORT RICHEY, FL, 34..., Port Richey, FL 34668
$150,000

2 beds

|

2 baths

|

1,210 sq ft

|

Villa

8111 BRADDOCK CIR 6, PORT RICHEY, FL, 34...
Community: Timber Oaks
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heather Lake Condominiums 940 VIRGINIA ST 108, DUNEDIN, FL, 34698, Dunedin, FL 34698
$219,900

2 beds

|

2 baths

|

1,024 sq ft

|

Condo

940 VIRGINIA ST 108, DUNEDIN, FL, 34698
Royal Stewart Arms 8 GLENCOE PL 307, DUNEDIN, FL, 34698, Dunedin, FL 34698
$225,000

2 beds

|

1 baths

|

1,100 sq ft

|

Condo

8 GLENCOE PL 307, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
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