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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
|
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
|
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
|
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
![11150 PARADISE POINT WAY, NEW PORT RICHE..., New Port Richey, FL 34654]()
3 beds
|2 baths
|1,558 sq ft
|House
11150 PARADISE POINT WAY, NEW PORT RICHE...
Community: Summertree
MLS W7880835 • BHHS FLORIDA PROPERTIES GROUP, JIM...
New
Highland Lakes on Lake Tarpon
![3481 MACLAREN DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,076 sq ft
|Villa
3481 MACLAREN DR, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8450327 • COLDWELL BANKER REALTY, Amanda Ju...
New
Timber Oaks
![10600 MIRA VISTA DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,561 sq ft
|House
10600 MIRA VISTA DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
MLS W7880951 • FUTURE HOME REALTY, Justine Manous...
New
Village on the Green
![2561 ROYAL PINES CIR # 14H, CLEARWATER, ..., Clearwater, FL 33763]()
2 beds
|2 baths
|1,095 sq ft
|Condo
2561 ROYAL PINES CIR # 14H, CLEARWATER, ...
Community: Village on the Green
MLS TB8448736 • BULLARD REALTY, Bozena Pniewski
Highland Lakes on Lake Tarpon
![1632 HEATHER PL, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,508 sq ft
|House
1632 HEATHER PL, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8429919 • RAGSDALE RESIDENTIAL REALTY, Sher...
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Questions? Call us:
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Green Dolphin
![1250 S PINELLAS AVE 307, TARPON SPRINGS,..., Tarpon Springs, FL 34689]()
1 beds
|1 baths
|669 sq ft
|Condo
1250 S PINELLAS AVE 307, TARPON SPRINGS,...
Community: Green Dolphin
MLS TB8404353 • CHARLES RUTENBERG REALTY INC, Joh...
Green Dolphin
![3203 GREEN DOLPHIN ST, TARPON SPRINGS, F..., Tarpon Springs, FL 34689]()
2 beds
|2 baths
|895 sq ft
|Villa
3203 GREEN DOLPHIN ST, TARPON SPRINGS, F...
Community: Green Dolphin
MLS TB8375406 • LIPPLY REAL ESTATE, Joe Gibbons
Esplanade at Starkey Ranch
![11111 CALLISIA DR, ODESSA, FL, 33556, Odessa, FL 33556]()
2 beds
|2 baths
|1,689 sq ft
|House
11111 CALLISIA DR, ODESSA, FL, 33556
Community: Esplanade at Starkey Ranch
MLS TB8344460 • FUTURE HOME REALTY INC, Andzelika...
Heritage Springs
![1251 RAMBLING VINE CT, TRINITY, FL, 3465..., Trinity, FL 34655]()
3 beds
|2 baths
|1,814 sq ft
|House
1251 RAMBLING VINE CT, TRINITY, FL, 3465...
Community: Heritage Springs
MLS TB8410011 • KELLER WILLIAMS REALTY- PALM H, M...
Heather Hills Villas
![857 CAMBRIDGE CT, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|1 baths
|863 sq ft
|Condo
857 CAMBRIDGE CT, DUNEDIN, FL, 34698
Community: Heather Hills Villas
MLS TB8418285 • CELTIC REALTY, David Vose
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
![1619 WHITHORN PL D, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684]()
1 beds
|1 baths
|814 sq ft
|Condo
1619 WHITHORN PL D, PALM HARBOR, FL, 346...
Community: Highland Lakes on Lake Tarpon
MLS TB8433122 • GALLERY PROPERTIES INTERNATIONAL,...
Green Dolphin
![1728 GOLFVIEW DR # 1728, TARPON SPRINGS,..., Tarpon Springs, FL 34689]()
2 beds
|2 baths
|1,125 sq ft
|Condo
1728 GOLFVIEW DR # 1728, TARPON SPRINGS,...
Community: Green Dolphin
MLS TB8440465 • LPT REALTY, LLC, Darlene Mauro
Pine Ridge at Palm Harbor
![2687 PINE RIDGE WAY F2, PALM HARBOR, FL,..., Palm Harbor, FL 34684]()
1 beds
|1 baths
|805 sq ft
|Condo
2687 PINE RIDGE WAY F2, PALM HARBOR, FL,...
Community: Pine Ridge at Palm Harbor
MLS TB8422192 • COLDWELL BANKER REALTY, Teri Peco...
Highland Lakes on Lake Tarpon
![2828 SHERBROOKE LN C, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684]()
1 beds
|2 baths
|814 sq ft
|Condo
2828 SHERBROOKE LN C, PALM HARBOR, FL, 3...
Community: Highland Lakes on Lake Tarpon
MLS TB8429395 • PYRAMID REALTY INC., Andrea Grutm...
Timber Oaks
![8723 BENTON DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668]()
2 beds
|2 baths
|1,422 sq ft
|House
8723 BENTON DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
MLS TB8440295 • REAL BROKER, LLC, Ryan Kessell
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Highland Lakes on Lake Tarpon
![3540 CAYMAN CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,325 sq ft
|Villa
3540 CAYMAN CT, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8447215 • BHHS FLORIDA PROPERTIES GROUP, Ta...
Esplanade at Starkey Ranch
![11121 EGERIA DR, ODESSA, FL, 33556, Odessa, FL 33556]()
3 beds
|3 baths
|3,016 sq ft
|House
11121 EGERIA DR, ODESSA, FL, 33556
Community: Esplanade at Starkey Ranch
MLS TB8438313 • LPT REALTY, LLC, Kenneth Gaydos
Highland Lakes on Lake Tarpon
![1012 DUNROBIN DR D, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,230 sq ft
|Villa
1012 DUNROBIN DR D, PALM HARBOR, FL, 346...
Community: Highland Lakes on Lake Tarpon
MLS TB8429536 • KELLER WILLIAMS REALTY- PALM H, V...
Heather Ridge
![1370 HEATHER RIDGE BLVD APT 105, DUNEDIN..., Dunedin, FL 34698]()
1 beds
|1 baths
|815 sq ft
|Condo
1370 HEATHER RIDGE BLVD APT 105, DUNEDIN...
Community: Heather Ridge
MLS TB8402918 • COASTAL PROPERTIES GROUP INTERNAT...
Heritage Springs
![1143 DUSTAN PL, TRINITY, FL, 34655, Trinity, FL 34655]()
3 beds
|2 baths
|1,704 sq ft
|House
1143 DUSTAN PL, TRINITY, FL, 34655
Community: Heritage Springs
MLS W7880858 • FUTURE HOME REALTY, Patti Reading
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.
Imperial Pines Condominiums
![3062 EASTLAND BLVD 105, CLEARWATER, FL, ..., Clearwater, FL 33761]()
2 beds
|2 baths
|1,250 sq ft
|Condo
3062 EASTLAND BLVD 105, CLEARWATER, FL, ...
Community: Imperial Pines Condominiums
MLS TB8439786 • SELECT PROPERTIES INC, Amanda Dye...
Summertree
![11427 TURTLE DOVE PL, NEW PORT RICHEY, F..., New Port Richey, FL 34654]()
3 beds
|2 baths
|1,686 sq ft
|House
11427 TURTLE DOVE PL, NEW PORT RICHEY, F...
Community: Summertree
MLS TB8349353 • COLDWELL BANKER REALTY, Yvette La...
Highland Lakes on Lake Tarpon
![3140 HIGHLANDS BLVD F, PALM HARBOR, FL, ..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|866 sq ft
|Condo
3140 HIGHLANDS BLVD F, PALM HARBOR, FL, ...
Community: Highland Lakes on Lake Tarpon
MLS TB8426127 • RAGSDALE RESIDENTIAL REALTY, Sher...
Highland Lakes on Lake Tarpon
![3532 CAYMAN CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,280 sq ft
|Villa
3532 CAYMAN CT, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8431710 • EXP REALTY LLC, Jessica Christian...
Heritage Lake
![9402 STONEWALL LN, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,646 sq ft
|House
9402 STONEWALL LN, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
MLS W7878140 • RE/MAX CHAMPIONS, Dina Gorby
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Royal Stewart Arms
![7 DUNOON PL APT 306, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|2 baths
|1,141 sq ft
|Condo
7 DUNOON PL APT 306, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
MLS TB8409170 • EXP REALTY LLC, Tanner Tillung
Highland Lakes on Lake Tarpon
![3098 E DORCHESTER DR, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,567 sq ft
|House
3098 E DORCHESTER DR, PALM HARBOR, FL, 3...
Community: Highland Lakes on Lake Tarpon
MLS TB8433251 • RAGSDALE RESIDENTIAL REALTY, Sher...
Highland Lakes on Lake Tarpon
![2880 DOONE CIR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,548 sq ft
|House
2880 DOONE CIR, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8440375 • RAGSDALE RESIDENTIAL REALTY, Sher...
Timber Oaks
![11310 CARRIAGE HILL DR APT 4, PORT RICHE..., Port Richey, FL 34668]()
2 beds
|2 baths
|978 sq ft
|Condo
11310 CARRIAGE HILL DR APT 4, PORT RICHE...
Community: Timber Oaks
MLS W7874068 • TROPIC SHORES REALTY LLC, Connie L...
Pinehurst Village
![1701 PINEHURST RD 4F, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
1 beds
|1 baths
|645 sq ft
|Villa
1701 PINEHURST RD 4F, DUNEDIN, FL, 34698
Community: Pinehurst Village
MLS TB8449935 • COLDWELL BANKER REALTY, Connie Di...
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
![948 VIRGINIA ST APT 107, DUNEDIN, FL, 34..., Dunedin, FL 34698]()
1 beds
|1 baths
|869 sq ft
|Condo
948 VIRGINIA ST APT 107, DUNEDIN, FL, 34...
Community: Heather Lake Condominiums
MLS TB8440923 • KELLER WILLIAMS REALTY PORTFOLIO ...
Pine Ridge at Palm Harbor
![1725 PINE RIDGE WAY E, PALM HARBOR, FL, ..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,177 sq ft
|Villa
1725 PINE RIDGE WAY E, PALM HARBOR, FL, ...
Community: Pine Ridge at Palm Harbor
MLS TB8400753 • SERHANT, Jennifer Spinelli
Timber Oaks
![8130 SAN FELIPE CT, PORT RICHEY, FL, 346..., Port Richey, FL 34668]()
3 beds
|2 baths
|1,670 sq ft
|House
8130 SAN FELIPE CT, PORT RICHEY, FL, 346...
Community: Timber Oaks
MLS W7880629 • RE/MAX SUNSET REALTY, Maria Diaz
Heritage Springs
![12148 ARRON TER, TRINITY, FL, 34655, Trinity, FL 34655]()
2 beds
|2 baths
|1,594 sq ft
|Villa
12148 ARRON TER, TRINITY, FL, 34655
Community: Heritage Springs
MLS TB8417139 • CONCI, REALTORS, Cyndi Olmstead
Timber Oaks
![10733 FALLEN LEAF LN, PORT RICHEY, FL, 3..., Port Richey, FL 34668]()
3 beds
|2 baths
|1,470 sq ft
|House
10733 FALLEN LEAF LN, PORT RICHEY, FL, 3...
Community: Timber Oaks
MLS TB8448504 • REAL BROKER, LLC, Kyle Hensley
Want to learn more about 55+ communities in Holiday?
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Heritage Lake
![9643 NOBLE CT, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,230 sq ft
|House
9643 NOBLE CT, NEW PORT RICHEY, FL, 3465...
Community: Heritage Lake
MLS TB8407746 • LPT REALTY, LLC., Amir Parajuli
Highland Lakes on Lake Tarpon
![2390 SHELLY DR D, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|918 sq ft
|Villa
2390 SHELLY DR D, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8315972 • CHARLES RUTENBERG REALTY INC, Mic...
Imperial Pines Condominiums
![3062 EASTLAND BLVD # D206, CLEARWATER, F..., Clearwater, FL 33761]()
1 beds
|1 baths
|920 sq ft
|Condo
3062 EASTLAND BLVD # D206, CLEARWATER, F...
Community: Imperial Pines Condominiums
MLS TB8442958 • LIPPLY REAL ESTATE, Paul Fernande...
Heritage Lake
![9309 TROWBRIDGE CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655]()
1 beds
|1 baths
|723 sq ft
|House
9309 TROWBRIDGE CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
MLS TB8447631 • MIHARA & ASSOCIATES INC., Denise ...
Heather Lake Condominiums
![946 VIRGINIA ST APT 102, DUNEDIN, FL, 34..., Dunedin, FL 34698]()
2 beds
|1 baths
|1,010 sq ft
|Condo
946 VIRGINIA ST APT 102, DUNEDIN, FL, 34...
Community: Heather Lake Condominiums
MLS TB8412620 • KELLER WILLIAMS REALTY PORTFOLIO ...
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.
