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Holiday, FL Homes for Sale with Private Pool

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  • /52

    $415,000

    • 3 Beds
    • 2 Baths
    • 1,683 Sq Ft

    2817 Plantain Dr, Holiday, FL 34691

    Welcome home to 2817 Plantain Dr! This beautifully maintained home, located inside the gated 55+ Key Vista Villas community, is perfectly situated between two preservation areas teeming with awe-inspiring Florida wildlife. Inside, the home shows like a model with soaring ceilings, crown molding, wide-plank luxury vinyl flooring, and an abundance of natural light throughout. The open layout

    Agent Photo

    Christina Probeyahn

    COASTAL PROPERTIES GROUP INTERNATIONAL

    (727) 607-6761

    2817 Plantain Dr, Holiday, FL 34691
  • /39

    $259,999

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft

    3309 Jackson Dr, Holiday, FL 34691

    Welcome to 3309 Jackson Dr., Holiday, FL – A Charming Pool Home in the Tahitian Development Discover this inviting 2-bedroom, 1-bathroom pool home in Holiday, Florida, located in the desirable Tahitian Development of Pasco County, just minutes from Gulf beaches, waterfront parks, restaurants, shopping, and everyday conveniences. This well-maintained single-family home offers comfortable living,

    Agent Photo

    Lance Willard

    CHARLES RUTENBERG REALTY INC

    (727) 594-5922

    3309 Jackson Dr, Holiday, FL 34691
  • /19

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,399 Sq Ft

    1326 Flotilla Dr, Holiday, FL 34690

    Waterfront Pool Home with Dock | Private Preserve Views | Move-In ReadyWelcome to 1326 Flotilla Dr — a beautifully updated waterfront pool home offering the Florida lifestyle buyers are searching for, with tranquil, private views overlooking protected preserve land. This peaceful setting provides a rare sense of privacy while still enjoying direct water access.Inside, the home features

    Agent Photo

    Tara Veprovsky

    COMPASS FLORIDA LLC

    (727) 607-0105

    1326 Flotilla Dr, Holiday, FL 34690
  • /100

    $1,145,000

    • 6 Beds
    • 5.5 Baths
    • 5,360 Sq Ft

    1238 Flotilla Dr, Holiday, FL 34690

    Welcome to this one-of-a-kind exclusive waterfront home pool home in Holiday, set on 1.18 acres at the end of a quiet cul-de-sac on the Anclote River, with water on three sides and approximately 630 feet of waterfront. Surrounded by beautiful moss-draped oak trees, the property offers a private and scenic setting with incredible potential. Featuring Spanish and Mediterranean-inspired

    Ruth Primeau CHARLES RUTENBERG REALTY INC

    1238 Flotilla Dr, Holiday, FL 34690
  • /33

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,942 Sq Ft

    3931 Holiday Lake Dr, Holiday, FL 34691

    Some properties offer a house. This one offers a whole world. Set along the shores of Lake Nash in Holiday's established Holiday Lakes neighborhood, this three-bedroom, two-bath home comes with something you simply cannot replicate — nearly five acres of submerged land, a piece of the lake itself, all conveyed with the sale. Bring your binoculars: sometimes white and blue herons wade at the

    Norma Vargas EXP REALTY LLC

    3931 Holiday Lake Dr, Holiday, FL 34691
  • /43

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 2,510 Sq Ft

    3030 Shadow Oaks Dr, Holiday, FL 34690

    Your next chapter begins now! 3030 Shadow Oaks Drive is ready for you to make it uniquely yours. This 3-bedroom, 2.5-bath, two-story pool home sits on a corner lot with minimal traffic. You’ll enjoy 2,510 sq. ft. of living (3,799 sq. ft. total) with an oversized three-car garage, ideal for a workshop or extra storage. Inside, vaulted ceilings complement a living room with a fireplace and sliders

    Erin Gwillim BHHS FLORIDA PROPERTIES GROUP

    3030 Shadow Oaks Dr, Holiday, FL 34690
  • /44

    $288,500

    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft

    5646 Andrea Dr, Holiday, FL 34690

    Welcome to your new home! Located in Holiday FL with no Hoa, CDD, and Not in a Flood Zone. East of USHighway 19. 3 bedrooms and 2 bath 1 car garage and a pool. Large Kitchen with plenty of wood cabinets,Corian counter tops and open to the great room. This space is amazing for those who enjoy family and friendsover to watch their favorite teams. Tile covers most of the entire house

    Michael Andrade F I GREY & SON RESIDENTIAL

    5646 Andrea Dr, Holiday, FL 34690
  • /37

    $349,900

    • 2 Beds
    • 2 Baths
    • 1,519 Sq Ft

    3409 Springfield Dr, Holiday, FL 34691

    Lovely setting on a spring-fed lake. Enjoy the spectacular sunsets and cool evening breezes off the lake as you sit in the bug-free zone of your caged pool yard. This unique home is one of the largest in the neighborhood, at over 1500+ square feet. Excellent floorplan with split bedrooms and lots of living space laid out with a separate living room, dining room, and family room. A very

    octavia Cheveresan RE/MAX ACTION FIRST OF FLORIDA

    3409 Springfield Dr, Holiday, FL 34691
  • /20

    $549,000

    • 3 Beds
    • 3 Baths
    • 2,218 Sq Ft

    3025 Sheppards Crook Ct, Holiday, FL 34691

    One or more photo(s) has been virtually staged. Step into a sun filled oasis! Updated 3 bedroom, 3 bath, pool home offering tranquil, peaceful views; with a rare opportunity to live in a intimate private gated community. Home is full of natural light. Move-in ready, lovingly maintained. New roof, New water heater, New air conditioner, New flooring, updated baths, updated kitchen. Solar panel keep

    Brad Reddick AZURE WATERFRONT REALTY, LLC

    3025 Sheppards Crook Ct, Holiday, FL 34691
  • /84

    $1,295,000

    • 3 Beds
    • 3 Baths
    • 3,234 Sq Ft

    3114 Bluff Blvd, Holiday, FL 34691

    Discover the charm of Florida’s Gulf Coast in this beautifully crafted waterfront home, set along Rocky Creek within the private and sought-after Bailey’s Bluff neighborhood. Tucked away on a peaceful street, the property showcases wide-open water views, stunning sunsets, and easy access to the Gulf, making it an excellent choice for boating enthusiasts and those seeking a relaxed coastal

    Michael Morton HOMEFRONT REALTY

    3114 Bluff Blvd, Holiday, FL 34691
  • /37

    $469,000

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft

    2706 Sierra Vista Way, Holiday, FL 34691

    Welcome home to the sought-after Key Vista community of Holiday! Perfectly positioned on a large corner lot, this beautifully maintained three-bedroom, two-bathroom residence offers the ideal blend of comfort and Florida outdoor living. Enjoy added peace of mind with major updates, including a 2018 Carrier AC system with a 2-stage air handler, a 2020 roof, and a GeoSpring hybrid water heater with

    Jeffrey Borham EXP REALTY LLC

    2706 Sierra Vista Way, Holiday, FL 34691
  • /37

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,967 Sq Ft

    3206 Pinon Dr, Holiday, FL 34691

    One or more photo(s) has been virtually staged. Welcome to this beautifully updated pool home in Holiday Lake Estates! This 3-bedroom, 2-bath home features a bright, open layout with a fully renovated kitchen with shaker cabinets, quartz countertops and new stainless steel appliances, new. Enjoy remodeled bathrooms with a double vanity in the primary suite, new luxury vinyl plank flooring and

    Philip Shaw LEERDAM PROPERTIES INC.

    3206 Pinon Dr, Holiday, FL 34691
  • /72

    $450,000

    • 4 Beds
    • 2 Baths
    • 1,837 Sq Ft

    3022 Jackson Dr, Holiday, FL 34691

    Welcome to this 4-bedroom, 2-bath, solar-powered, pool home offering plenty of comfortable living space on the water. The property also features its own dock right in the backyard, providing direct access to Lake Conley. Inside, the home offers a bright, open feel with abundant natural light, a neutral color palette, and luxury vinyl plank flooring throughout the living areas. The kitchen is

    William Perez LPT REALTY, LLC

    3022 Jackson Dr, Holiday, FL 34691
  • /28

    $349,900

    • 2 Beds
    • 2 Baths
    • 1,540 Sq Ft

    5844 Riddle Rd, Holiday, FL 34690

    Situated on an oversized lot, this well-maintained 2-bedroom, 2-bath home offers a functional layout, flexible outdoor space, and the Florida lifestyle buyers are looking for. The home features a desirable split floor plan, with two spacious bedrooms—each offering its own en-suite bathroom, providing privacy and convenience. Both bathrooms are well-sized and fully functional. A standout feature

    Mark Berdelle REAL BROKER, LLC

    5844 Riddle Rd, Holiday, FL 34690
  • /21

    $319,999

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft

    1715 Kenilworth St, Holiday, FL 34691

    Welcome to 1715 Kenilworth Street in Holiday, Florida, a beautifully renovated home offering modern updates, functional living spaces, and the added benefit of no HOA restrictions. This move-in-ready property features refreshed interiors, contemporary finishes, and a layout designed for both everyday comfort and easy entertaining. The spacious backyard includes a private pool, creating the

    Alejandro Conti LPT REALTY, LLC

    1715 Kenilworth St, Holiday, FL 34691
  • /88

    $1,859,900

    • 4 Beds
    • 4 Baths
    • 3,412 Sq Ft

    1906 Gulfview Dr, Holiday, FL 34691

    Stunning Ocean views from this waterfront paradise. The opportunity has arisen to acquire the former home of the renowned local artist Elaine Hahn and AIA emeritus architect Byron G McIntyre. Located in the sought-after Bailey’s Bluff community, this stunning 4-bedroom, 4-bath elevated home offers 3,412 square feet of coastal living with panoramic water views throughout and 160 feet of private

    Nicholas Horton BANNER INT'L REAL ESTATE

    1906 Gulfview Dr, Holiday, FL 34691
  • /53

    $849,900

    • 3 Beds
    • 2.5 Baths
    • 2,583 Sq Ft

    2138 Bayou Dr, Holiday, FL 34691

    One or more photo(s) has been virtually staged. Open access to the Gulf!! Experience elevated waterfront living in this elegant 3 bed/2 bath residence with a versatile bonus room, thoughtfully designed to blend architectural charm, refined finishes, and seamless indoor–outdoor flow, all in the sought after Baileys Bluff Estates! The generously sized secondary bedrooms offer ample closet space and

    Vanessa Leonard KELLER WILLIAMS REALTY- PALM H

    2138 Bayou Dr, Holiday, FL 34691
  • /49

    $390,000

    • 3 Beds
    • 2 Baths
    • 1,301 Sq Ft

    2651 San Luis Rd, Holiday, FL 34691

    Welcome to this well-maintained lakefront home on Lake Conley in Pasco County, sitting high and dry in a non-flood zone on a street lined with new construction. This 3-bedroom, 2-bath home offers 1,301 square feet of living space, with 2,271 total including a generous screened lanai with panoramic water views. The updated kitchen features modern finishes, ample cabinetry, and great counter space,

    DAVID CITRO PALM PARADISE REALTY GROUP

    2651 San Luis Rd, Holiday, FL 34691
  • /63

    $345,000

    • 4 Beds
    • 2 Baths
    • 1,635 Sq Ft

    2615 Almond Dr, Holiday, FL 34691

    Move-in ready renovated home! This 4-bedroom, 2-bath property features a fully updated kitchen with modern cabinets, granite countertops, and updated appliances. Water-resistant vinyl flooring in the main areas and new carpet in the family room for added comfort. The home also offers new impact windows and doors, new insulation for improved efficiency and energy savings. The backyard includes a

    Yenislei Machado HOME PRIME REALTY LLC

    2615 Almond Dr, Holiday, FL 34691
  • /51

    $539,900

    • 4 Beds
    • 3 Baths
    • 1,761 Sq Ft

    1166 Chancellor Dr, Holiday, FL 34690

    Stunning fully remodeled 4-bedroom, 3-bath waterfront home offering privacy, functionality, and true Gulf-access living. This exceptional property has remained high and dry with no flooding during recent storms, providing peace of mind along with an unbeatable natural setting. Set along a scenic bend of the river, the backyard overlooks a private island preserve—meaning no rear neighbors, just

    Shawn Poole SNAP REALTY LLC

    1166 Chancellor Dr, Holiday, FL 34690
  • /24

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,587 Sq Ft

    3625 Richboro Dr, Holiday, FL 34691

    This beautifully updated 3-bedroom, 2-bath home features a spacious, open layout perfect for everyday living and entertaining. Enjoy ceramic tile floors throughout, remodeled bathrooms, and a modern kitchen with granite countertops and stainless steel appliances. The primary bathroom features dual sinks and granite finishes, adding a touch of elegance.Step outside to your private backyard

    Maria Ospina PEOPLE'S TRUST REALTY

    3625 Richboro Dr, Holiday, FL 34691
  • /33

    $269,800

    • 3 Beds
    • 2 Baths
    • 1,326 Sq Ft

    3349 Overland Dr, Holiday, FL 34691

    TROPICAL POOL & POND PARADISE HOME FEATURING A SPARKLING SWIMMING POOL, 3 BEDROOMS, 2 BATHROOMS AND A LARGE COVERED LANAI AND SCREEN-ENCLOSED POOL-DECK. NEW ROOF, NEW KITCHEN, NEW AC, NEW APPLIANCES, QUARTZ COUNTERSTOPS, NEW LUXURY WATERPROOF VINYL PLANK FLOORS, new electrical panel, new pool pump and new cartridge filter! All new interior paint and fixtures. Beautiful curb appeal with a spacious

    Joseph Buchi DENNIS REALTY & INV. CORP.

    3349 Overland Dr, Holiday, FL 34691
  • /93

    $1,449,000

    • 4 Beds
    • 4 Baths
    • 4,204 Sq Ft

    3143 Pineview Dr, Holiday, FL 34691

    Welcome to your dream waterfront estate in the sought-after Baileys Bluff community! This stunning custom mini mansion is perched high and dry with no HOA, offering unparalleled privacy and luxury. Enjoy direct Gulf access with a new dock equipped with electric and water, a seawall, and a serene backyard oasis featuring a lagoon-style saltwater pool, spa, waterfall, expansive Belgard paver deck,

    Jennifer Tobey RE/MAX CHAMPIONS

    3143 Pineview Dr, Holiday, FL 34691
  • /59

    $265,000

    • 3 Beds
    • 2 Baths
    • 1,577 Sq Ft

    4233 Darlington Rd, Holiday, FL 34691

    Move-in ready pool home! 3BR/2BA, 2,648 SF heated with private pool. Excellent location. Minutes to beaches, shopping & dining. Don’t miss this turnkey opportunity! PRICE FIRM. DON'T SEND ANY OFFER UNDER AKING PRICE

    Francisco Rojas GLOBAL FORTUNE REALTY LLC

    4233 Darlington Rd, Holiday, FL 34691
  • /66

    $629,900

    • 4 Beds
    • 3.5 Baths
    • 3,553 Sq Ft

    5657 Oceanic Rd, Holiday, FL 34690

    Welcome to 5657 Oceanic Rd in Holiday, Florida a quiet, well-established neighborhood with no flood zone. Situated on an oversized lot, this unique property offers flexibility, space, and privacy rarely found in the area.The home features two dedicated office spaces, ideal for remote work, a home-based business, or creative studios. A standout 1,900-square-foot garage provides exceptional

    Nicole Volentine DALTON WADE INC

    5657 Oceanic Rd, Holiday, FL 34690
  • /37

    $349,999

    • 2 Beds
    • 2 Baths
    • 2,278 Sq Ft

    1414 Grand Blvd, Holiday, FL 34690

    NEW ROOF JUST PUT ON AUGUST 2025,NEW FANS, AND THE INSIDE PAINTED! NEWER ELECTRIC, WINDOWS, WATER HEATER, AND AN 11 YEAR OLD AC THAT HAS BEEN INSPECTED AND WORKS GREAT ! CHARMING 2-BEDROOM 2-BATH POOL HOME WITH STUNNING VIEWS OF LAKE BELCHER. IT DID NOT FLOOD DURING THE STORMS LAST YEAR AND HAS ENDLESS POTENTIAL! THIS IS A RARE OPPORTUNITY TO HAVE A DEEP WATERWAY RIGHT OUT OF YOUR BACK DOOR WITH

    Jeanine Affetto RE/MAX CHAMPIONS

    1414 Grand Blvd, Holiday, FL 34690
  • /48

    $525,000

    • 4 Beds
    • 2.5 Baths
    • 2,395 Sq Ft

    2653 Sierra Vista Way, Holiday, FL 34691

    Make sure to check out the Virtual Tour for a 3D Model w/ Walkthrough, Floor Plan w/ Measurements, Video, & more! Welcome to 2653 Sierra Vista Way located in the stunning Key Vista Community! The Community offers so many amenities for their residences including a Game Room, Event Space, Heated Community Pool & Hot Tub, Volleyball Court, Tennis Court, Weight Room & MORE! This exquisite 4-bedroom,

    Joshua Hanoud EXP REALTY LLC

    2653 Sierra Vista Way, Holiday, FL 34691
  • /23

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,519 Sq Ft

    3105 Pinon Dr, Holiday, FL 34691

    Auction Property. Short Sale. * * FANTASTIC OPPORTUNITY * * Welcome to this 3-bedroom, 2-bath POOL HOME located in the heart of Holiday, FL. This home offers the perfect blend of comfort, style, and indoor-outdoor living. Step inside to find a bright, open floor plan with abundant natural light, spacious living and dining areas, and a thoughtfully designed layout ideal for both everyday living

    Matthew Brashear RE/MAX ELITE REALTY

    3105 Pinon Dr, Holiday, FL 34691
  • /48

    $50,000

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    505 Barbara Way, Tarpon Springs, FL 34689

    Welcome to The Meadows, a vibrant 55+ resort-style community in the heart of Tarpon Springs. This beautifully updated 2-bedroom, 2-bath manufactured home offers comfort, convenience, and an affordable path to ownership. Recent renovations include a new front deck, 2021 water heater, updated water lines, vapor barrier with screened skirting, and upgraded kitchen and bath fixtures. The spacious

    Cara Keelin

    505 Barbara Way, Tarpon Springs, FL 34689

Home Trends in Holiday, FL

Housing Trends

Median Sale Price
$235,000
Median Single Family Sale Price
$242,000
Median Townhouse Sale Price
$279,000
Median 2 Bedroom Sale Price
$125,000
Median 1 Bedroom Sale Price
$105,000
Average Price Per Sq Ft
$196
Number of Homes for Sale
214
Last 12 months Home Sales
724
Months of Supply
3.50
Median List Price
$250,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
0%
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