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Holiday, FL 55+ active adult communities & homes for sale
26 communities near Holiday
318 homes near Holiday
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$300Ks
Key Vista Villas, Holiday, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2005
|
170 homes
5 rating (1 reviews)
![Highland Lakes on Lake Ta...]()
<$100k
- $500Ks
Highland Lakes on Lake Ta..., Palm Harbor, FL
Resale Only
|
55+ age-restricted
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Built 1977 - 1989
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2,454 homes
4.7 rating (13 reviews)
![Heritage Springs]()
$300Ks
- $400Ks
Heritage Springs, Trinity, FL
Resale Only
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55+ age-restricted
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Built 1999 - 2006
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1,337 homes
<$100k
- $300Ks
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
- $300Ks
Heritage Lake, New Port Richey, FL
Resale Only
|
55+ age-restricted
|
Built 1981 - 1994
|
932 homes
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$100Ks
- $300Ks
Summertree, New Port Richey, FL
Resale Only
|
55+ age-restricted
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Built 1974 - 2015
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800 homes
3.5 rating (2 reviews)
![Timber Greens]()
$200Ks
- $400Ks
Timber Greens, New Port Richey, FL
Resale Only
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55+ age-restricted
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Built 1994 - 2004
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783 homes
$400Ks
- $1Ms
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only
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Age-targeted
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Built 2016 - 2022
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517 homes
3.3 rating (3 reviews)
![Royal Stewart Arms]()
$200Ks
- $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
5 rating (1 reviews)
![Village on the Green]()
$100Ks
- $200Ks
Village on the Green, Clearwater, FL
Resale Only
|
55+ age-restricted
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Built 1978 - 1981
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448 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
- $200Ks
Green Dolphin, Tarpon Springs, FL
Resale Only
|
55+ age-restricted
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Built 1974 - 1990
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315 homes
$300Ks
- $400Ks
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
- $200Ks
Heather Ridge, Dunedin, FL
Resale Only
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55+ age-restricted
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Built 1978 - 1987
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273 homes
5 rating (1 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
$100Ks
- $200Ks
Pinehurst Village, Dunedin, FL
Resale Only
|
55+ age-restricted
|
Built 1973 - 1976
|
240 homes
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2 rating (1 reviews)
![Beacon Lakes]()
$100Ks
Beacon Lakes, New Port Richey, FL
Resale Only
|
55+ age-restricted
|
Built 1975 - 1982
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210 homes
$400Ks
- $1Ms
Edgewater Arms, Dunedin, FL
Resale Only
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55+ age-restricted
|
Built 1970 - 1974
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209 homes
$100Ks
- $200Ks
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
$100Ks
- $200Ks
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
$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.
$300Ks
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
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
$100Ks
- $200Ks
Heather Hills Villas, Dunedin, FL
Resale Only
|
55+ age-restricted
|
Built 1971 - 1976
|
64 homes
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Summertree
![11806 WHITE ASH DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654]()
3 beds
|2 baths
|1,349 sq ft
|House
11806 WHITE ASH DR, NEW PORT RICHEY, FL,...
Community: Summertree
MLS A4665817 • REALTY ONE GROUP SUNSHINE, Arno Is...
Timber Oaks
![11241 DOLLAR LAKE DR 5, PORT RICHEY, FL,..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,386 sq ft
|Condo
11241 DOLLAR LAKE DR 5, PORT RICHEY, FL,...
Community: Timber Oaks
MLS W7874936 • KELLER WILLIAMS REALTY- PALM H, Br...
Timber Oaks
![11321 STANSBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,268 sq ft
|Villa
11321 STANSBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
MLS W7880610 • RE/MAX SUNSET REALTY, Brian Pfiste...
Green Dolphin
![1250 S PINELLAS AVE APT 405, TARPON SPRI..., Tarpon Springs, FL 34689]()
1 beds
|1 baths
|669 sq ft
|Condo
1250 S PINELLAS AVE APT 405, TARPON SPRI...
Community: Green Dolphin
MLS TB8381256 • BHHS FLORIDA PROPERTIES GROUP, Ch...
Highland Lakes on Lake Tarpon
![3116 HIGHLANDS BLVD # 3116, PALM HARBOR,..., Palm Harbor, FL 34684]()
1 beds
|1 baths
|636 sq ft
|Condo
3116 HIGHLANDS BLVD # 3116, PALM HARBOR,...
Community: Highland Lakes on Lake Tarpon
MLS TB8419716 • COLDWELL BANKER REALTY, Linda Kar...
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Highland Lakes on Lake Tarpon
![2238 LARK CIR D, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,230 sq ft
|Condo
2238 LARK CIR D, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8392086 • DALTON WADE INC, Leroy Hunton
Pinehurst Village
![1701 PINEHURST RD 19F, DUNEDIN, FL, 3469..., Dunedin, FL 34698]()
1 beds
|1 baths
|645 sq ft
|Condo
1701 PINEHURST RD 19F, DUNEDIN, FL, 3469...
Community: Pinehurst Village
MLS TB8410868 • KELLER WILLIAMS REALTY- PALM H, J...
Esplanade at Starkey Ranch
![11398 JUGLANS DR, ODESSA, FL, 33556, Odessa, FL 33556]()
3 beds
|3 baths
|2,410 sq ft
|House
11398 JUGLANS DR, ODESSA, FL, 33556
Community: Esplanade at Starkey Ranch
MLS W7875778 • KELLER WILLIAMS REALTY- PALM H, Ju...
Timber Oaks
![11110 CARRIAGE HILL DR 1, PORT RICHEY, F..., Port Richey, FL 34668]()
2 beds
|2 baths
|954 sq ft
|Condo
11110 CARRIAGE HILL DR 1, PORT RICHEY, F...
Community: Timber Oaks
MLS W7880706 • FLORIDA LUXURY REALTY INC, Frank C...
Key Vista Villas
![2931 WALNUT GROVE CT, HOLIDAY, FL, 34691, Holiday, FL 34691]()
3 beds
|2 baths
|1,341 sq ft
|House
2931 WALNUT GROVE CT, HOLIDAY, FL, 34691
Community: Key Vista Villas
MLS W7873078 • FUTURE HOME REALTY, Kathy Dobies
Download the Ultimate 55+ Homebuying Guide
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Highland Lakes on Lake Tarpon
![3957 TARPON POINTE CIR, PALM HARBOR, FL,..., Palm Harbor, FL 34684]()
3 beds
|2 baths
|1,588 sq ft
|House
3957 TARPON POINTE CIR, PALM HARBOR, FL,...
Community: Highland Lakes on Lake Tarpon
MLS TB8430711 • KELLER WILLIAMS REALTY PORTFOLIO ...
Highland Lakes on Lake Tarpon
![1131 ORANGE TREE CIR C, PALM HARBOR, FL,..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|960 sq ft
|Villa
1131 ORANGE TREE CIR C, PALM HARBOR, FL,...
Community: Highland Lakes on Lake Tarpon
MLS TB8427694 • KELLER WILLIAMS REALTY- PALM H, J...
Timber Oaks
![11231 DOLLAR LAKE DR APT 6, PORT RICHEY,..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,386 sq ft
|Condo
11231 DOLLAR LAKE DR APT 6, PORT RICHEY,...
Community: Timber Oaks
MLS W7877774 • PARADISE WEST REALTY, INC, Claudia...
Briar Patch
![6520 THICKET TRL, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34653]()
2 beds
|2 baths
|1,359 sq ft
|Townhouse
6520 THICKET TRL, NEW PORT RICHEY, FL, 3...
Community: Briar Patch
MLS W7880475 • RE/MAX ALLIANCE GROUP, Debbie Daws...
Summertree
![11736 WHITE ASH DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654]()
2 beds
|2 baths
|1,515 sq ft
|House
11736 WHITE ASH DR, NEW PORT RICHEY, FL,...
Community: Summertree
MLS W7878322 • BHHS FLORIDA PROPERTIES GROUP, JIM...
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Summertree
![11521 ROSE TREE DR, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654]()
2 beds
|2 baths
|1,777 sq ft
|House
11521 ROSE TREE DR, NEW PORT RICHEY, FL,...
Community: Summertree
MLS TB8365155 • IMPACT REALTY TAMPA BAY, Jacqueli...
Green Dolphin
![1250 S PINELLAS AVE APT 214, TARPON SPRI..., Tarpon Springs, FL 34689]()
2 beds
|2 baths
|871 sq ft
|Condo
1250 S PINELLAS AVE APT 214, TARPON SPRI...
Community: Green Dolphin
MLS TB8385544 • KELLER WILLIAMS REALTY- PALM H, S...
Highland Lakes on Lake Tarpon
![3184 BRUNSWICK CIR, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,950 sq ft
|House
3184 BRUNSWICK CIR, PALM HARBOR, FL, 346...
Community: Highland Lakes on Lake Tarpon
MLS TB8431223 • COMPASS FLORIDA, LLC, Mark Middle...
Timber Oaks
![8130 MERRIMAC DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668]()
2 beds
|2 baths
|1,470 sq ft
|House
8130 MERRIMAC DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
MLS TB8443837 • CENTURY 21 CIRCLE, Ginger Gillett...
Royal Stewart Arms
![8 GLENCOE PL 307, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|1 baths
|1,100 sq ft
|Condo
8 GLENCOE PL 307, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
MLS TB8427811 • COASTAL PROPERTIES GROUP INTERNAT...
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
![6606 GARDEN PALM CT, NEW PORT RICHEY, FL..., New Port Richey, FL 34655]()
3 beds
|2 baths
|1,892 sq ft
|House
6606 GARDEN PALM CT, NEW PORT RICHEY, FL...
Community: Timber Greens
MLS W7879596 • CENTURY 21 PALM REALTY, Deborah Ro...
Timber Oaks
![11404 STANSBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,440 sq ft
|Villa
11404 STANSBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
MLS TB8409997 • WEICHERT REALTORS EXCLUSIVE PROPE...
Highland Lakes on Lake Tarpon
![2846 HIGHLANDS BLVD D, PALM HARBOR, FL, ..., Palm Harbor, FL 34684]()
1 beds
|2 baths
|814 sq ft
|Condo
2846 HIGHLANDS BLVD D, PALM HARBOR, FL, ...
Community: Highland Lakes on Lake Tarpon
MLS TB8438449 • EXP REALTY LLC, John Rurkowski
Heritage Springs
![11600 WEAVER PARK CT, TRINITY, FL, 34655, Trinity, FL 34655]()
2 beds
|2 baths
|1,964 sq ft
|House
11600 WEAVER PARK CT, TRINITY, FL, 34655
Community: Heritage Springs
MLS TB8439463 • COLDWELL BANKER REALTY, Teresa Si...
Pine Ridge at Palm Harbor
![2666 PINE RIDGE WAY C2, PALM HARBOR, FL,..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,150 sq ft
|Condo
2666 PINE RIDGE WAY C2, PALM HARBOR, FL,...
Community: Pine Ridge at Palm Harbor
MLS TB8418562 • COLDWELL BANKER REALTY, Teri Peco...
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Timber Oaks
![11541 ORLEANS LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668]()
2 beds
|2 baths
|1,152 sq ft
|Condo
11541 ORLEANS LN, PORT RICHEY, FL, 34668
Community: Timber Oaks
MLS TB8393166 • FUTURE HOME REALTY INC, Laura But...
Heritage Lake
![4961 GRIST MILL CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,326 sq ft
|Villa
4961 GRIST MILL CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
MLS W7879376 • HENDRIK MARIE REALTY LLC, Tina Ost...
Royal Stewart Arms
![7 DUNOON PL 304, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|2 baths
|1,141 sq ft
|Condo
7 DUNOON PL 304, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
MLS TB8410948 • CENTURY 21 COASTAL ALLIANCE, Cind...
Heritage Springs
![1630 LAKESTONE DR, TRINITY, FL, 34655, Trinity, FL 34655]()
3 beds
|2 baths
|1,956 sq ft
|House
1630 LAKESTONE DR, TRINITY, FL, 34655
Community: Heritage Springs
MLS W7879015 • FUTURE HOME REALTY, Patti Reading
Pine Ridge at Palm Harbor
![2687 PINE RIDGE WAY E1, PALM HARBOR, FL,..., Palm Harbor, FL 34684]()
1 beds
|1 baths
|805 sq ft
|Condo
2687 PINE RIDGE WAY E1, PALM HARBOR, FL,...
Community: Pine Ridge at Palm Harbor
MLS TB8419146 • COLDWELL BANKER REALTY, Teri Peco...
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.
Village on the Green
![2541 LAURELWOOD DR # 8C, CLEARWATER, FL,..., Clearwater, FL 33763]()
2 beds
|2 baths
|1,030 sq ft
|Villa
2541 LAURELWOOD DR # 8C, CLEARWATER, FL,...
Community: Village on the Green
MLS TB8395288 • CHARLES RUTENBERG REALTY INC, Kar...
Green Dolphin
![1933 GOLFVIEW DR # 1933, TARPON SPRINGS,..., Tarpon Springs, FL 34689]()
2 beds
|2 baths
|1,125 sq ft
|Condo
1933 GOLFVIEW DR # 1933, TARPON SPRINGS,...
Community: Green Dolphin
MLS TB8445798 • MAVREALTY, Drew Moser
Heather Ridge
![1421 HEATHER RIDGE BLVD # 1421, DUNEDIN,..., Dunedin, FL 34698]()
2 beds
|1 baths
|1,077 sq ft
|Villa
1421 HEATHER RIDGE BLVD # 1421, DUNEDIN,...
Community: Heather Ridge
MLS TB8437628 • RE/MAX ACTION FIRST OF FLORIDA, M...
Imperial Pines Condominiums
![3076 EASTLAND BLVD 210, CLEARWATER, FL, ..., Clearwater, FL 33761]()
2 beds
|2 baths
|1,250 sq ft
|Condo
3076 EASTLAND BLVD 210, CLEARWATER, FL, ...
Community: Imperial Pines Condominiums
MLS TB8406002 • REALTY ONE GROUP EPIC, Jung Choi
Briar Patch
![6421 REMUS DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34653]()
2 beds
|2 baths
|964 sq ft
|Villa
6421 REMUS DR, NEW PORT RICHEY, FL, 3465...
Community: Briar Patch
MLS OM705359 • EXP REALTY LLC, Lelah Hughes
Want to learn more about 55+ communities in Holiday?
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Highland Lakes on Lake Tarpon
![1605 WHITEBRIDGE DR B, PALM HARBOR, FL, ..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,000 sq ft
|Condo
1605 WHITEBRIDGE DR B, PALM HARBOR, FL, ...
Community: Highland Lakes on Lake Tarpon
MLS TB8444503 • COASTAL PROPERTIES GROUP INTERNAT...
Esplanade at Starkey Ranch
![3239 FORSYTHIA DR, ODESSA, FL, 33556, Odessa, FL 33556]()
3 beds
|3 baths
|2,368 sq ft
|House
3239 FORSYTHIA DR, ODESSA, FL, 33556
Community: Esplanade at Starkey Ranch
MLS TB8438442 • RE/MAX REALTEC GROUP INC, Shirley...
Timber Oaks
![11403 VERSAILLES LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,171 sq ft
|Condo
11403 VERSAILLES LN, PORT RICHEY, FL, 34...
Community: Timber Oaks
MLS W7880404 • NEXTHOME LUXURY REAL ESTATE, Cynth...
Highland Lakes on Lake Tarpon
![3115 MISSION GROVE DR, PALM HARBOR, FL, ..., Palm Harbor, FL 34684]()
1 beds
|1 baths
|636 sq ft
|Villa
3115 MISSION GROVE DR, PALM HARBOR, FL, ...
Community: Highland Lakes on Lake Tarpon
MLS TB8342770 • COLDWELL BANKER REALTY, Patricia ...
Highland Lakes on Lake Tarpon
![3499 CEDAR LN, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,230 sq ft
|Villa
3499 CEDAR LN, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8437763 • EXP REALTY LLC, Jeffrey Borham
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 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?
Want to learn more about 55+ communities in Holiday?
318
homes
near Holiday
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© 2025 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: Nov 29, 2025.
This application does not include information on all of the properties available for sale at this time.
