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Holiday, FL 55+ active adult communities & homes for sale
26 communities near Holiday
274 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
- $400Ks
Highland Lakes on Lake Ta..., Palm Harbor, FL
Resale Only
|
55+ age-restricted
|
Built 1977 - 1989
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2,454 homes
4.7 rating (13 reviews)
![Heritage Springs]()
$300Ks
- $500Ks
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
5 rating (1 reviews)
![Timber Oaks]()
<$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]()
$300Ks
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
- $900Ks
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
- $400Ks
Royal Stewart Arms, Dunedin, FL
Resale Only
|
55+ age-restricted
|
Built 1968 - 1975
|
449 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 (1 reviews)
![Village on the Green]()
$100Ks
- $200Ks
Village on the Green, Clearwater, FL
Resale Only
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55+ age-restricted
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Built 1978 - 1981
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448 homes
<$100k
- $200Ks
Green Dolphin, Tarpon Springs, FL
Resale Only
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55+ age-restricted
|
Built 1974 - 1990
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315 homes
$300Ks
- $400Ks
Anchorage, Palm Harbor, FL
Resale Only
|
55+ age-restricted
|
Built 1972 - 1979
|
279 homes
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5 rating (1 reviews)
![Pine Ridge at Palm Harbor]()
$100Ks
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
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55+ age-restricted
|
Built 1973 - 1976
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240 homes
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
|
209 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
Heather Lake Condominiums, Dunedin, FL
Resale Only
|
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
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55+ age-restricted
|
Built 1985 - 1985
|
181 homes
$300Ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 1983
|
148 homes
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$100Ks
- $200Ks
Linkside Village, Port Richey, FL
Resale Only
|
55+ age-restricted
|
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
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.
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
Timber Greens
![6543 PINE WALK DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,380 sq ft
|Villa
6543 PINE WALK DR, NEW PORT RICHEY, FL, ...
Community: Timber Greens
MLS W7880794 • RE/MAX CHAMPIONS, Diane s Hawk-Jum...
Esplanade at Starkey Ranch
![11295 JUGLANS DR, ODESSA, FL, 33556, Odessa, FL 33556]()
3 beds
|3 baths
|2,305 sq ft
|House
11295 JUGLANS DR, ODESSA, FL, 33556
Community: Esplanade at Starkey Ranch
MLS TB8437457 • CHARLES RUTENBERG REALTY INC, Ama...
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...
Timber Oaks
![8140 SAN FELIPE CT, PORT RICHEY, FL, 346..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,510 sq ft
|House
8140 SAN FELIPE CT, PORT RICHEY, FL, 346...
Community: Timber Oaks
MLS W7878436 • PARADISE WEST REALTY, INC, Claudia...
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Heritage Springs
![12202 ARRON TER, TRINITY, FL, 34655, Trinity, FL 34655]()
2 beds
|2 baths
|1,873 sq ft
|House
12202 ARRON TER, TRINITY, FL, 34655
Community: Heritage Springs
MLS TB8424270 • FLORIDA EXECUTIVE REALTY, Stephan...
Timber Oaks
![11211 ROLLINGWOOD DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,465 sq ft
|House
11211 ROLLINGWOOD DR, PORT RICHEY, FL, 3...
Community: Timber Oaks
MLS TB8440332 • RE/MAX CHAMPIONS, Colleen Nolan
Highland Lakes on Lake Tarpon
![3283 HILARY CIR 2C, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,000 sq ft
|Villa
3283 HILARY CIR 2C, PALM HARBOR, FL, 346...
Community: Highland Lakes on Lake Tarpon
MLS T3537352 • FUTURE HOME REALTY INC, Gissel Fon...
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
Download the Ultimate 55+ Homebuying Guide
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Summertree
![11446 SINATRA CT, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34654]()
3 beds
|2 baths
|1,597 sq ft
|House
11446 SINATRA CT, NEW PORT RICHEY, FL, 3...
Community: Summertree
MLS W7881668 • RE/MAX CHAMPIONS, Lynette Krull
Timber Oaks
![11516 VERSAILLES LN, PORT RICHEY, FL, 34..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,166 sq ft
|Condo
11516 VERSAILLES LN, PORT RICHEY, FL, 34...
Community: Timber Oaks
MLS W7877499 • LATIMER & ASSOCIATES REALTY, Dave ...
Heather Lake Condominiums
![940 VIRGINIA ST 105, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
1 beds
|1 baths
|683 sq ft
|Condo
940 VIRGINIA ST 105, DUNEDIN, FL, 34698
Community: Heather Lake Condominiums
MLS TB8459889 • MARK SPAIN REAL ESTATE, Roxanne M...
Heather Lake Condominiums
![841 PATRICIA AVE 306, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|2 baths
|934 sq ft
|Condo
841 PATRICIA AVE 306, DUNEDIN, FL, 34698
Community: Heather Lake Condominiums
MLS TB8457688 • SELECT PROPERTIES INC, Amanda Dye...
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Edgewater Arms
![632 EDGEWATER DR 433, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|2 baths
|1,425 sq ft
|Condo
632 EDGEWATER DR 433, DUNEDIN, FL, 34698
Community: Edgewater Arms
MLS TB8448114 • COLDWELL BANKER REALTY, Denis Rom...
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 SOUTH TAMPA, Jodi...
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
Beacon Lakes
![3838 LANYARD CT, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34652]()
2 beds
|2 baths
|1,144 sq ft
|Condo
3838 LANYARD CT, NEW PORT RICHEY, FL, 34...
Community: Beacon Lakes
MLS W7875781 • RE/MAX CHAMPIONS, Sue Salm
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
![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...
Heritage Lake
![4814 GRIST MILL CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,174 sq ft
|Villa
4814 GRIST MILL CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
MLS W7880057 • BHHS FLORIDA PROPERTIES GROUP, Kat...
Highland Lakes on Lake Tarpon
![3201 MCMATH DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,332 sq ft
|Villa
3201 MCMATH DR, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8414809 • AGILE GROUP REALTY, Darren August...
Highland Lakes on Lake Tarpon
![2834 THISTLE CT, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,529 sq ft
|House
2834 THISTLE CT, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8427823 • FUTURE HOME REALTY INC, Lisa DesC...
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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...
Highland Lakes on Lake Tarpon
![899 CLELAND CT A, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,230 sq ft
|Condo
899 CLELAND CT A, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8455060 • COLDWELL BANKER REALTY, Amanda Ju...
Green Dolphin
![1250 S PINELLAS AVE 804, TARPON SPRINGS,..., Tarpon Springs, FL 34689]()
1 beds
|1 baths
|565 sq ft
|Condo
1250 S PINELLAS AVE 804, TARPON SPRINGS,...
Community: Green Dolphin
MLS TB8430818 • COLDWELL BANKER REALTY, Renee Gia...
Summertree
![12200 PUTTER GREEN CT, NEW PORT RICHEY, ..., New Port Richey, FL 34654]()
3 beds
|2 baths
|1,719 sq ft
|Villa
12200 PUTTER GREEN CT, NEW PORT RICHEY, ...
Community: Summertree
MLS OM715465 • LPT REALTY, LLC., Kristie Dimaraki...
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 FORBES PL 512, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|2 baths
|1,181 sq ft
|Condo
9 FORBES PL 512, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
MLS W7873759 • RE/MAX CHAMPIONS, Ashley Quaife
Timber Oaks
![8619 GOLD PINE DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,658 sq ft
|House
8619 GOLD PINE DR, PORT RICHEY, FL, 3466...
Community: Timber Oaks
MLS W7881379 • RE/MAX ALLIANCE GROUP, April Noven...
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...
Pinehurst Village
![1701 PINEHURST RD 10F, DUNEDIN, FL, 3469..., Dunedin, FL 34698]()
2 beds
|2 baths
|1,025 sq ft
|Condo
1701 PINEHURST RD 10F, DUNEDIN, FL, 3469...
Community: Pinehurst Village
MLS TB8418797 • SOUTHERN LIFE REALTY, Mary White
Timber Oaks
![10819 LOS SANTOS DR, PORT RICHEY, FL, 34..., Port Richey, FL 34668]()
2 beds
|2 baths
|1,107 sq ft
|House
10819 LOS SANTOS DR, PORT RICHEY, FL, 34...
Community: Timber Oaks
MLS TB8371597 • DALTON WADE INC, Douglas Brown
Want to learn more about 55+ communities in Holiday?
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Esplanade at Starkey Ranch
![11599 CALLISIA DR, ODESSA, FL, 33556, Odessa, FL 33556]()
2 beds
|2 baths
|1,689 sq ft
|House
11599 CALLISIA DR, ODESSA, FL, 33556
Community: Esplanade at Starkey Ranch
MLS W7880552 • RE/MAX ALLIANCE GROUP, Denise Wool...
Esplanade at Starkey Ranch
![11426 JUGLANS DR, ODESSA, FL, 33556, Odessa, FL 33556]()
3 beds
|2 baths
|1,931 sq ft
|House
11426 JUGLANS DR, ODESSA, FL, 33556
Community: Esplanade at Starkey Ranch
MLS W7878845 • BHHS FLORIDA PROPERTIES GROUP, Lis...
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 Lake
![9404 ROCKBRIDGE CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655]()
2 beds
|2 baths
|1,227 sq ft
|Condo
9404 ROCKBRIDGE CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
MLS W7881223 • FLORIDA LUXURY REALTY INC, Jennife...
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.
Briar Patch
![6506 REMUS DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34653]()
2 beds
|2 baths
|964 sq ft
|Villa
6506 REMUS DR, NEW PORT RICHEY, FL, 3465...
Community: Briar Patch
MLS TB8334345 • 54 REALTY LLC, Kari Hazeltine
Heritage Springs
![1055 BLYTH HILL CT, TRINITY, FL, 34655, Trinity, FL 34655]()
2 beds
|2 baths
|1,609 sq ft
|Villa
1055 BLYTH HILL CT, TRINITY, FL, 34655
Community: Heritage Springs
MLS TB8420686 • KELLER WILLIAMS REALTY- PALM H, C...
Highland Lakes on Lake Tarpon
![1109 MADEIRA DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684]()
2 beds
|2 baths
|1,165 sq ft
|Villa
1109 MADEIRA DR, PALM HARBOR, FL, 34684
Community: Highland Lakes on Lake Tarpon
MLS TB8447125 • PEOPLE'S TRUST REALTY, Regina Vit...
Edgewater Arms
![634 EDGEWATER DR 348, DUNEDIN, FL, 34698, Dunedin, FL 34698]()
2 beds
|2 baths
|1,265 sq ft
|Condo
634 EDGEWATER DR 348, DUNEDIN, FL, 34698
Community: Edgewater Arms
MLS TB8446572 • COLDWELL BANKER REALTY, Denis Rom...
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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...
Highland Lakes on Lake Tarpon
![2722 SHERBROOKE LN D, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684]()
1 beds
|2 baths
|814 sq ft
|Condo
2722 SHERBROOKE LN D, PALM HARBOR, FL, 3...
Community: Highland Lakes on Lake Tarpon
MLS TB8404316 • EXP REALTY LLC, Heather Terflinge...
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?
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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.
© 2026 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: Jan 09, 2026.
This application does not include information on all of the properties available for sale at this time.
