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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
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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
|
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
|
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
|
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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Heather Lake Condominiums
![960 VIRGINIA ST 205, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|2 baths
|965 sq ft
|Condo
960 VIRGINIA ST 205, DUNEDIN, FL, 34698
Community: Heather Lake Condominiums
MLS TB8350858 • KELLER WILLIAMS REALTY PORTFOLIO ...
Timber Oaks
![11220 ELDERBERRY DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,347 sq ft
|House
11220 ELDERBERRY DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
MLS W7880718 • NEXTHOME LUXURY REAL ESTATE, Carlo...
Heritage Lake
![4739 CARRINGTON CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,261 sq ft
|Condo
4739 CARRINGTON CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
MLS W7879600 • BHHS FLORIDA PROPERTIES GROUP, Kat...
Heritage Lake
![9444 ROCKBRIDGE CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,335 sq ft
|Condo
9444 ROCKBRIDGE CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
MLS W7878391 • BHHS FLORIDA PROPERTIES GROUP, Kat...
Highland Lakes on Lake Tarpon
![2150 SHELLY DR A, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|918 sq ft
|Condo
2150 SHELLY DR A, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8436293 • CHARLES RUTENBERG REALTY INC, All...
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Village on the Green
![2567 OAKLEAF LN 41B, CLEARWATER, FL, 337..., Clearwater, FL 33763]()
2 beds
|2 baths
|960 sq ft
|Villa
2567 OAKLEAF LN 41B, CLEARWATER, FL, 337...
Community: Village on the Green
MLS TB8381894 • CHARLES RUTENBERG REALTY INC, Kar...
Edgewater Arms
![632 EDGEWATER DR UNIT 238, DUNEDIN, FL, ..., Dunedin, FL 34698]()
2 beds
|2 baths
|1,220 sq ft
|Condo
632 EDGEWATER DR UNIT 238, DUNEDIN, FL, ...
Community: Edgewater Arms
MLS TB8450633 • COASTAL PROPERTIES GROUP INTERNAT...
Village on the Green
![2502 LAURELWOOD DR # 3B, CLEARWATER, FL,..., Clearwater, FL 33763]()
2 beds
|2 baths
|1,058 sq ft
|Villa
2502 LAURELWOOD DR # 3B, CLEARWATER, FL,...
Community: Village on the Green
MLS TB8449853 • CENTURY 21 CIRCLE, Judy Ossian
Heather Ridge
![1417 HEATHER RIDGE BLVD, DUNEDIN, FL, 34..., Dunedin, FL 34698]()
2 beds
|2 baths
|1,324 sq ft
|Condo
1417 HEATHER RIDGE BLVD, DUNEDIN, FL, 34...
Community: Heather Ridge
MLS TB8449515 • DALTON WADE INC, Lisa Suriano
Heritage Lake
![9451 ROCKBRIDGE CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,515 sq ft
|Condo
9451 ROCKBRIDGE CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
MLS TB8446787 • KELLER WILLIAMS REALTY- PALM H, V...
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
![2740 WHITEBRIDGE DR A, PALM HARBOR, FL, ..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,000 sq ft
|Condo
2740 WHITEBRIDGE DR A, PALM HARBOR, FL, ...
Community: Highland Lakes on Lake Tarpon
MLS W7879860 • KELLER WILLIAMS REALTY- PALM H, Er...
Highland Lakes on Lake Tarpon
![1700 HIGHLAND CLUB CT, PALM HARBOR, FL, ..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,280 sq ft
|Villa
1700 HIGHLAND CLUB CT, PALM HARBOR, FL, ...
Community: Highland Lakes on Lake Tarpon
MLS TB8339288 • KELLER WILLIAMS REALTY- PALM H, B...
Timber Oaks
![8131 BUGLE CT 2, PORT RICHEY, FL, 34668, Port Richey, FL 34668]()
2 beds
|2 baths
|1,000 sq ft
|Condo
8131 BUGLE CT 2, PORT RICHEY, FL, 34668
Community: Timber Oaks
MLS S5135327 • LA ROSA REALTY LLC, Antonio Nouer
Village on the Green
![2555 ROYAL PINES CIR # 15A, CLEARWATER, ..., Clearwater, FL 33763]()
2 beds
|2 baths
|1,095 sq ft
|Condo
2555 ROYAL PINES CIR # 15A, CLEARWATER, ...
Community: Village on the Green
MLS TB8419423 • BHHS FLORIDA PROPERTIES GROUP, Pa...
Timber Oaks
![8718 BENTON DR, PORT RICHEY, FL, 34668, Port Richey, FL 34668]()
2 beds
|2 baths
|1,218 sq ft
|House
8718 BENTON DR, PORT RICHEY, FL, 34668
Community: Timber Oaks
MLS W7879940 • TROPIC SHORES REALTY LLC, Jennifer...
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Pinehurst Village
![1701 PINEHURST RD 33E, DUNEDIN, FL, 3469..., Dunedin, FL 34698]()
2 beds
|2 baths
|875 sq ft
|Condo
1701 PINEHURST RD 33E, DUNEDIN, FL, 3469...
Community: Pinehurst Village
MLS TB8398659 • MIHARA & ASSOCIATES INC., Christi...
Village on the Green
![2529 OAKLEAF LN 30A, CLEARWATER, FL, 337..., Clearwater, FL 33763]()
2 beds
|2 baths
|980 sq ft
|Villa
2529 OAKLEAF LN 30A, CLEARWATER, FL, 337...
Community: Village on the Green
MLS TB8448070 • BHHS FLORIDA PROPERTIES GROUP, Pa...
Heritage Springs
![1201 DUSTAN PL, TRINITY, FL, 34655, Trinity, FL 34655]()
3 beds
|2 baths
|2,032 sq ft
|House
1201 DUSTAN PL, TRINITY, FL, 34655
Community: Heritage Springs
MLS W7880565 • EXP REALTY, LLC, James Adams
Heritage Lake
![4636 PORTLAND MANOR DR, NEW PORT RICHEY,..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,552 sq ft
|House
4636 PORTLAND MANOR DR, NEW PORT RICHEY,...
Community: Heritage Lake
MLS TB8450222 • KELLER WILLIAMS TAMPA PROP., Meli...
Pinehurst Village
![1701 PINEHURST RD 3E, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
1 beds
|1 baths
|645 sq ft
|Villa
1701 PINEHURST RD 3E, DUNEDIN, FL, 34698
Community: Pinehurst Village
MLS O6360532 • HOUWZER INC, Daniel Robinson
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 612, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|2 baths
|1,181 sq ft
|Condo
9 HAIG PL 612, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
MLS U8254132 • BHHS FLORIDA PROPERTIES GROUP, Rac...
Pinehurst Village
![1701 PINEHURST RD 9H, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|2 baths
|1,025 sq ft
|Condo
1701 PINEHURST RD 9H, DUNEDIN, FL, 34698
Community: Pinehurst Village
MLS TB8434029 • RE/MAX ELITE REALTY, Dustin Layto...
Heritage Lake
![4720 SHEFFIELD DR # 4720, NEW PORT RICHE..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,204 sq ft
|Condo
4720 SHEFFIELD DR # 4720, NEW PORT RICHE...
Community: Heritage Lake
MLS W7876968 • BHHS FLORIDA PROPERTIES GROUP, Kat...
Esplanade at Starkey Ranch
![3214 FORSYTHIA DR, ODESSA, FL, 33556, Odessa, FL 33556]()
3 beds
|3 baths
|2,385 sq ft
|House
3214 FORSYTHIA DR, ODESSA, FL, 33556
Community: Esplanade at Starkey Ranch
MLS TB8397657 • COMPASS FLORIDA LLC, Eric Dungy
Heather Lake Condominiums
![821 PATRICIA AVE 103, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|1 baths
|935 sq ft
|Condo
821 PATRICIA AVE 103, DUNEDIN, FL, 34698
Community: Heather Lake Condominiums
MLS TB8411737 • LIPPLY REAL ESTATE, Joe Gibbons
Want to learn more about 55+ communities in Holiday?
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Highland Lakes on Lake Tarpon
![2320 SHELLY DR B, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|918 sq ft
|Condo
2320 SHELLY DR B, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS C7515964 • SELLSTATE EXCELSIOR REALTY, Rick P...
Green Dolphin
![1250 S PINELLAS AVE 910, TARPON SPRINGS,..., Tarpon Springs, FL 34689]()
1 beds
|1 baths
|669 sq ft
|Condo
1250 S PINELLAS AVE 910, TARPON SPRINGS,...
Community: Green Dolphin
MLS TB8420142 • ENGEL & VOLKERS TAMPA DOWNTOWN, R...
Heritage Lake
![4756 SHEFFIELD DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,201 sq ft
|Condo
4756 SHEFFIELD DR, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
MLS W7877099 • FLORIDA LUXURY REALTY INC, Jennife...
Highland Lakes on Lake Tarpon
![1609 WHITEBRIDGE DR C, PALM HARBOR, FL, ..., Palm Harbor, FL 34684]()
1 beds
|1 baths
|964 sq ft
|Condo
1609 WHITEBRIDGE DR C, PALM HARBOR, FL, ...
Community: Highland Lakes on Lake Tarpon
MLS G5104168 • BEACON REAL ESTATE & ASSOC, June C...
Green Dolphin
![1306 GOLFVIEW DR # 1306, TARPON SPRINGS,..., Tarpon Springs, FL 34689]()
2 beds
|2 baths
|1,240 sq ft
|Condo
1306 GOLFVIEW DR # 1306, TARPON SPRINGS,...
Community: Green Dolphin
MLS W7877365 • SANDPEAK REALTY, Dick Maxwell
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 Oaks
![11204 PEMBRIDGE CT 5, PORT RICHEY, FL, 3..., Port Richey, FL 34668]()
2 beds
|2 baths
|978 sq ft
|Condo
11204 PEMBRIDGE CT 5, PORT RICHEY, FL, 3...
Community: Timber Oaks
MLS TB8353645 • FUTURE HOME REALTY INC, Dora Orda...
Heritage Springs
![1228 ASHBOURNE CIR, TRINITY, FL, 34655, Trinity, FL 34655]()
3 beds
|2 baths
|1,975 sq ft
|House
1228 ASHBOURNE CIR, TRINITY, FL, 34655
Community: Heritage Springs
MLS W7877607 • RE/MAX CHAMPIONS, Mazin Shehayeb
Green Dolphin
![2201 PINE DR, TARPON SPRINGS, FL, 34689, Tarpon Springs, FL 34689]()
2 beds
|2 baths
|1,320 sq ft
|Villa
2201 PINE DR, TARPON SPRINGS, FL, 34689
Community: Green Dolphin
MLS TB8449469 • AGILE GROUP REALTY, Darren August...
Imperial Pines Condominiums
![3062 EASTLAND BLVD UNIT 402, CLEARWATER,..., Clearwater, FL 33761]()
2 beds
|2 baths
|1,250 sq ft
|Condo
3062 EASTLAND BLVD UNIT 402, CLEARWATER,...
Community: Imperial Pines Condominiums
MLS TB8381828 • COLDWELL BANKER REALTY, Lynne Lei...
Heritage Springs
![1208 FLORA VISTA ST, TRINITY, FL, 34655, Trinity, FL 34655]()
2 beds
|2 baths
|1,793 sq ft
|Villa
1208 FLORA VISTA ST, TRINITY, FL, 34655
Community: Heritage Springs
MLS TB8429879 • CHARLES RUTENBERG REALTY INC, Car...
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Royal Stewart Arms
![9 HAIG PL 806, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
1 beds
|1 baths
|802 sq ft
|Condo
9 HAIG PL 806, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
MLS U8246566 • BHHS FLORIDA PROPERTIES GROUP, Rac...
Beacon Lakes
![4446 CHART CT, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34652]()
2 beds
|2 baths
|1,144 sq ft
|Condo
4446 CHART CT, NEW PORT RICHEY, FL, 3465...
Community: Beacon Lakes
MLS TB8429995 • LPT REALTY, LLC, Cody Harris
Timber Greens
![6622 PINE WALK DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655]()
3 beds
|2 baths
|1,944 sq ft
|House
6622 PINE WALK DR, NEW PORT RICHEY, FL, ...
Community: Timber Greens
MLS W7879281 • CENTURY 21 PALM REALTY, Deborah Ro...
Timber Oaks
![11231 DOLLAR LAKE DR APT 1, PORT RICHEY,..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,210 sq ft
|Condo
11231 DOLLAR LAKE DR APT 1, PORT RICHEY,...
Community: Timber Oaks
MLS L4956369 • BHHS FLORIDA PROPERTIES GROUP, Tin...
Heritage Lake
![4951 GRIST MILL CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,174 sq ft
|House
4951 GRIST MILL CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
MLS TB8427736 • KELLER WILLIAMS REALTY- PALM H, K...
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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The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 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.
