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Holiday, FL Homes for Sale with Private Pool

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  • /16

    $437,000

    • 3 Beds
    • 3 Baths
    • 2,694 Sq Ft

    3040 Sheppards Crook Ct, Holiday, FL 34691

    Lowest Listing in neighborhood!! Don't let this opportunity pass you by**Quiet gated community with fewer than ten homes. This property offers a peaceful retreat on an expansive lot. The home features an open floor plan with split bedrooms for privacy and a lovely in-ground pool, ideal for relaxation and outdoor fun. While it could use some updating, it is competitively priced, providing an

    Agent Photo

    Nancy Yialouris

    Y GROUP REALTY

    (727) 617-3888

    3040 Sheppards Crook Ct, Holiday, FL 34691
  • /55

    $599,000

    • 6 Beds
    • 3 Baths
    • 3,086 Sq Ft

    6653 Mineral Springs Rd, Holiday, FL 34690

    Welcome to your upgraded oasis in the heart of New Port Richey!Built in 2020 and packed with modern features, this spacious 6-bedroom, 3-bathroom home offers over 3,000 square feet of heated living space and a 2-car garage—ideal for large households or multigenerational living. Nestled on just over a quarter acre of fully fenced property, there’s room for everyone (including the pups!). Step

    Angie Haddon LPT REALTY, LLC

    6653 Mineral Springs Rd, Holiday, FL 34690
  • /47

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,429 Sq Ft

    3133 Pineview Dr Unit 2, Holiday, FL 34691

    Price Repositioning- Great Opportunity! Charming Old Florida Waterfront Retreat in Sought-After Baileys Bluff Estates! NO Flooding – NO Storm Damage – Elevated Lot! Step into the tranquil charm of Old Florida living in this beautifully maintained, single-story waterfront gem in desirable Baileys Bluff Estates. Perched on a high, never-flooded lot with a finished floor elevation of 11 feet, this

    Marcy Daniels COLDWELL BANKER REALTY

    3133 Pineview Dr Unit 2, Holiday, FL 34691
  • /49

    $459,900

    • 3 Beds
    • 2 Baths
    • 2,069 Sq Ft

    2924 Windridge Dr, Holiday, FL 34691

    **BRAND NEW ROOF TO BE INSTALLED BEFORE CLOSING**Come check out the most sought-after Community of Gulf Trace! This stunning 3-bedroom, 2-bath, 2-car garage, pool home is your Florida dream come true! NO flood insurance required! High & dry! The property offers lush landscaping, great curb appeal, and an incredible pond and water fountain view that will leave you breathless! Step through the

    Cortney Bain CHARLES RUTENBERG REALTY INC

    2924 Windridge Dr, Holiday, FL 34691
  • /14

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,334 Sq Ft

    4307 Woodfield Ave, Holiday, FL 34691

    One or more photo(s) has been virtually staged. Welcome to this better-than-new POOL home in Holiday, FL! With modern upgrades and a spacious layout, this home offers everything you need for comfortable living. Offering 3-bedrooms, 2-bathrooms and a 1-CAR GARAGE. The open-concept layout seamlessly connects the kitchen, living, and dining areas. The GOURMET KITCHEN features NEWER STAINLESS-STEEL

    Stephanie Cruz PRIME REALTY OF FL LLC

    4307 Woodfield Ave, Holiday, FL 34691
  • /65

    $499,900

    • 5 Beds
    • 3 Baths
    • 2,429 Sq Ft

    2310 Wood Pointe Dr, Holiday, FL 34691

    WELCOME TO YOUR NEW OASIS IN KEY VISTAAre you searching for a home that's spacious enough for a growing family or multi-generational living? Nestled in the desirable Key Vista community, this stunning 5-bedroom, 3-bathroom home is ready to impress. Designed for both entertaining and comfortable living, this property seamlessly blends functionality with style. FEATURE-RICH INTERIORSAs you step

    Maggie Loving FUTURE HOME REALTY INC

    2310 Wood Pointe Dr, Holiday, FL 34691
  • /48

    $629,900

    • 4 Beds
    • 3 Baths
    • 3,024 Sq Ft

    3136 Sandhill Dr, Holiday, FL 34691

    Welcome to this spacious 4-bedroom, 3-bathroom + office executive pool home with over 3,000 square feet of thoughtfully designed living space. Elevated ceilings, large windows, and multiple glass sliders throughout the home create a bright, welcoming atmosphere with peaceful pond views. The living room and dining room are at the front of the home for ideal formal entertaining. At the heart of the

    Dean Ribble RE/MAX REALTEC GROUP INC

    3136 Sandhill Dr, Holiday, FL 34691
  • /48

    $383,000

    • 3 Beds
    • 2 Baths
    • 1,930 Sq Ft

    1102 Springtime Dr, Holiday, FL 34691

    Welcome Home to Your Rare Find in Holiday Lakes West! Discover this spacious 3-bedroom, 2-bedroom, 2 car garage, screen enclosed pool home with a huge bonus room! Inside, the open-concept kitchen with quartz countertop shines with a large center island, perfect for entertaining. Relax outdoors with two screened-in porches- one in the cozy front courtyard and another overlooking the sparkling

    Roger Fruits HOMEFRONT REALTY

    1102 Springtime Dr, Holiday, FL 34691
  • /38

    $459,900

    • 3 Beds
    • 2 Baths
    • 2,055 Sq Ft

    5771 Catskill Rd, Holiday, FL 34690

    Location, location, location and Breathtaking views from this 2 story beautiful home. Living room with Cathedral ceilings and marble faced fireplace. Large kitchen and dining area with skylights and water views. This property sits on the Anclote River and Lake Diane. Huge master bedroom with walk in closet and more water views! Swimming pool with newer screens overlooks the lake. Newer 2 year

    Grace Pineyro COLDWELL BANKER FIGREY&SONRES

    5771 Catskill Rd, Holiday, FL 34690
  • /56

    $475,000

    • 3 Beds
    • 2 Baths
    • 2,167 Sq Ft

    3457 Foxhall Dr, Holiday, FL 34691

    PRICE REDUCTION, beautiful and elegant layout, large scaled home boasting open floor plan with living room/dining area combination, huge decorative front window, architectural shelving, crown molding and wall to wall sliders across the back of the house opens to the large pool and lanai area with views to the gardens and fruit trees that will delight any gardener. The living/dining room opens to

    Sten and Denise Tallarida FUTURE HOME REALTY INC

    3457 Foxhall Dr, Holiday, FL 34691
  • /31

    $330,000

    • 2 Beds
    • 2 Baths
    • 1,468 Sq Ft

    5905 Berkford Dr, Holiday, FL 34690

    Welcome to this beautifully maintained home in the peaceful Shadow Oaks community of Holiday, tucked away on a quiet dead-end street. Bring your boat or RV—this property includes a separate driveway equipped with a 30-amp outlet and water hookup, so you can store your toys right at home. Inside, you’ll find an open split-bedroom floor plan that offers both functionality and privacy, with premium

    Shayna Teator MARK SPAIN REAL ESTATE

    5905 Berkford Dr, Holiday, FL 34690
  • /9

    $270,000

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

    3309 Rock Valley Dr, Holiday, FL 34691

    This is a nice 2 bedroom, 2 bathroom home. Great for a rental investment in a good neighbourhood. The property has a new roof on it as of 2023. The kitchen cabinets and countertop were just replaced. It has new tile flooring in the kitchen as well. The property has a salt water pool. The pool was redone 4 years ago with a 2 year old pool heater. There is a powered shed in the back yard. One of

    Youbel Montesino LPT REALTY, LLC

    3309 Rock Valley Dr, Holiday, FL 34691
  • /32

    $249,000

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

    3633 Richboro Dr, Holiday, FL 34691

    Welcome home to this fabulous, well-loved and maintained pool home! Freshly painted and cleaned, 2 bedroom, 2 bath +bonus room 1 car garage with NO HOA and NO CDD fees home, located on a quiet street in Beacon Square. The spacious new kitchen features, newer stainless steel appliances and pass through windows to the finished porch where you can enjoy family gatherings while watching family

    Natalya Halprin CHARLES RUTENBERG REALTY INC

    3633 Richboro Dr, Holiday, FL 34691
  • /71

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,216 Sq Ft

    3514 Truman Dr, Holiday, FL 34691

    Welcome to your Beautiful Pool Home! Don't miss this opportunity to enjoy the South Pasco location (easy commute to Pinellas County). This desirable home has 2 ample size bedrooms, a full bath in the house and a full bath in the garage. You will love the open floor plan with the large kitchen open to the large living room and dining room. The floorplan is flexible to have dining/living space

    Christine Knighton SMITH & ASSOCIATES REAL ESTATE

    3514 Truman Dr, Holiday, FL 34691
  • /20

    $247,499 Open Sat 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,216 Sq Ft

    3302 Eisenhower Dr, Holiday, FL 34691

    Motivated Seller – Charming 3-Bedroom Home in the Aloha Garden community of Holiday, FL!This well-maintained 3-bedroom, 2-bathroom home offers modern updates and great potential. Enjoy peace of mind with a brand new electric panel with 3 year warranty, newer roof (2022), along with updated carpet, vinyl flooring, and blinds. The exterior is freshly painted, adding to its curb appeal. Relax in the

    Sydney Klehm REAL BROKER, LLC

    3302 Eisenhower Dr, Holiday, FL 34691
  • /23

    $289,000

    • 2 Beds
    • 2 Baths
    • 1,306 Sq Ft

    3438 Bigelow Dr, Holiday, FL 34691

    2BR/2BA with SWIMMING POOL in Holiday, Florida! NO FLOOD ZONE for your peach of mind! Peace of mind comes with a BRAND NEW SHINGLE ROOF – replaced in March 2025, ensuring durability and reliability for years to come. Welcome to your personal oasis just minutes to the Gulf Beaches! Step inside to discover a spacious and OPEN CONCEPT FLOOR PLAN with a bright, airy atmosphere, offering a seamless

    Brad Uline EXP REALTY LLC

    3438 Bigelow Dr, Holiday, FL 34691
  • /35

    $229,500 Open Sat 11AM - 1PM

    • 4 Beds
    • 2 Baths
    • 1,134 Sq Ft

    3340 Columbus Dr, Holiday, FL 34691

    Welcome to your charming retreat in Holiday, FL! This delightful 4 bedroom, 2 bathroom home offers a spacious and updated kitchen featuring stainless steel appliances and elegant granite countertops ideal for cooking and entertaining. The master suite boasts a private bath with a custom designed, oversized walk-in shower for a spa-like experience. Enjoy peace of mind with a newer AC and roof,

    Mark Fazzini RE/MAX REALTEC GROUP INC

    3340 Columbus Dr, Holiday, FL 34691
  • /77

    $1,400,000

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

    3114 Bluff Blvd, Holiday, FL 34691

    Luxury Waterfront Living in Bailey’s Bluff!THIS HOME HAS NEVER EXPERIENCED FLOODING FROM ANY STORM OR HURRICANE, making it a solid and reliable investment.Discover unparalleled coastal living in this custom-built waterfront home on Rocky Creek in the highly sought-after secluded Bailey’s Bluff neighborhood. Nestled on a quiet street, this stunning property offers breathtaking water views,

    Rose Winters LPT REALTY, LLC

    3114 Bluff Blvd, Holiday, FL 34691
  • /42

    $325,000

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

    1414 Grand Blvd, Holiday, FL 34690

    LARGE PRICE IMPROVEMENT! CHARMING 2-BEDROOM 2-BATH POOL HOME WITH STUNNING VIEWS OF LAKE BELCHER AND ENDLESS POTENTIAL!THIS SPACIOUS 2278 SQ FT HEATED HOME SITS ON A GENEROUS, FENCED, QUARTER ACRE LOT AND OFFERS THE PERFECT BLEND OF CONVENIENCE,COMFORT, AND OPPORTUNITY. FEATURING TWO MASTER SUITES AND A SPLIT - BEDROOM FLOOR PLAN, THIS PROPERTY BOASTS A LARGE PATIO WITH BEAUTIFUL VIEWS

    Jeanine Affetto RE/MAX CHAMPIONS

    1414 Grand Blvd, Holiday, FL 34690
  • /61

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,988 Sq Ft

    1214 Stover Ct, Holiday, FL 34691

    CHARMING LAKEFRONT HOME ON LAKE NASH! This original-owner home is nestled on a quiet cul-de-sac and offers nearly 75 feet of waterfront living. New roof 7/2023. PGT hurricane proof double pained windows. There is a covered back porch where you can relax and enjoy serene lake views. A utility room with a washer and dryer adds convenience, while the fenced-in yard provides privacy and includes an

    Dorothy Petrisin Success Property Management In

    1214 Stover Ct, Holiday, FL 34691
  • /40

    $1,997,000

    • 3 Beds
    • 3 Baths
    • 3,041 Sq Ft

    1903 Gulfview Dr, Holiday, FL 34691

    Nestled in a prime location with 171 FEET OF WATER FRONTAGE and its UNOBSTRUCTED GULF VIEWS AND DIRECT ACCESS from the brand-new BOAT DOCK this home is truly unmatched. From the moment you arrive, the paved driveway leads to an impressive seven-car garage, setting the stage for a remarkable residence. Access to the main living area is effortless with the choice of a grand front staircase or the

    Dalton Robinson THE MAGNOLIA GROUP OF FLORIDA

    1903 Gulfview Dr, Holiday, FL 34691
  • /30

    $315,000

    • 3 Beds
    • 1.5 Baths
    • 1,401 Sq Ft

    3628 Holiday Lake Dr, Holiday, FL 34691

    This stunning 3-bedroom, 2-bath property offers the perfect blend of comfort and style. From the moment you step inside, you'll be greeted by an open-concept layout with abundant natural light, creating a warm and inviting atmosphere.The spacious living area flows seamlessly into an updated kitchen, complete with stainless steel appliances, granite countertops, and ample storage. The

    Fabiola Gutierrez COLDWELL BANKER REALTY

    3628 Holiday Lake Dr, Holiday, FL 34691
  • /50

    $589,999

    • 5 Beds
    • 4 Baths
    • 3,072 Sq Ft

    1919 Blue River Rd, Holiday, FL 34691

    Welcome to your dream home! This expansive 5-bedroom, 4-bath beauty boasts over 3,072 sq ft of living space, offering both luxury and comfort. Situated in a serene community with a private pond view, over a quarter acre lot, and no backyard neighbors, this home provides the perfect retreat for relaxation and entertaining. The gourmet kitchen features newer, top-of-the-line stainless steel

    Erica Antonakos QUICKSILVER REAL ESTATE GROUP

    1919 Blue River Rd, Holiday, FL 34691
  • /39

    $279,000

    • 3 Beds
    • 2 Baths
    • 1,723 Sq Ft

    1333 Normandy Blvd, Holiday, FL 34691

    Welcome to 1333 Normandy Blvd, a charming 3-bedroom, 2-bathroom home nestled in the heart of Holiday Lake Estates. This delightful residence offers a split floor plan, providing privacy and comfort for all family members.As you step inside, you’ll be greeted by a spacious kitchen featuring a breakfast bar—perfect for casual dining and morning coffee. The kitchen seamlessly flows into the

    Nicki Vogiatzis PREMIERE PROPERTIES

    1333 Normandy Blvd, Holiday, FL 34691
  • /22

    $470,000

    • 4 Beds
    • 2 Baths
    • 2,384 Sq Ft

    3633 Nettle Creek Ct, Holiday, FL 34691

    ***Motivated seller - Seller willing to contribute up to $10,000 towards buyer's closing costs.*** Discover your dream home in this beautiful spacious 4 bedroom 2 bathroom property. Nestled in a well-maintained and welcoming neighborhood, this home immediately stands out with its curb appeal and inviting atmosphere. Conveniently located close to the beaches, this property offers over 2,300 sq.

    Peter Yang DALTON WADE INC

    3633 Nettle Creek Ct, Holiday, FL 34691
  • /56

    $300,000

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

    3105 Pinon Dr, Holiday, FL 34691

    **CLEAN HOME INSPECTION REPORT - 2 YEAR BUYER’S CHOICE HOME WARRANTY - PLUS NEGOTIABLE INTEREST RATE BUY DOWN!!** Step into your perfect Florida retreat with this incredible 3-bedroom, 2-bathroom home! Motivated sellers have priced this beauty to move fast, so don’t miss your chance to make it yours.Inside, you’ll find an open floor plan filled with natural light and beautiful tile flooring

    Kristina Gabrielsen LPT REALTY, LLC.

    3105 Pinon Dr, Holiday, FL 34691
  • /56

    $699,900

    • 3 Beds
    • 3.5 Baths
    • 2,367 Sq Ft

    3020 Sheppards Crook Ct, Holiday, FL 34691

    Executive Style Custom-Built home in Private Gated Community will impress all of your friends and associates! Massive curb appeal! Gorgeous stamped concrete driveways, three story home with 4 travertine balconies and oversized 3 car garage with workshop and full bath. This offers a perfect blend of modern elegance and timeless appeal. and meticulously maintained, this home is ready to welcome its

    Jonathan Minerick HOMECOIN.COM

    3020 Sheppards Crook Ct, Holiday, FL 34691
  • /29

    $315,000

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

    3349 Overland Dr, Holiday, FL 34691

    One or more photo(s) has been virtually staged. Welcome to this charming and well-maintained 3-bedroom, 2-bathroom home located in the heart of Holiday, FL. Offering a spacious layout, a private backyard, and numerous recent updates, this home is the perfect blend of comfort and convenience. Key Features: Open & Bright Layout: The inviting floor plan features generous living spaces, including a

    Carlos Carrion Ortiz SOUTH CEDAR REAL ESTATE, INC

    3349 Overland Dr, Holiday, FL 34691
  • /48

    $480,000

    • 4 Beds
    • 3 Baths
    • 2,547 Sq Ft

    3612 Covington Dr, Holiday, FL 34691

    This spacious 4 bedroom, 3 bath, pool home sits on a lot overlooking a large tranquil pond with an abundance of wildlife and nature's beauty. This home has new solar panels that will be paid off in full at closing, and an Electric Vehicle charging station already installed! The double door entry leads to a three way split floor plan with high ceilings throughout. The view of the pool and pond is

    Larry Geiger ROBERT SLACK LLC

    3612 Covington Dr, Holiday, FL 34691
  • /84

    $684,900

    • 5 Beds
    • 4 Baths
    • 3,124 Sq Ft

    2533 Wood Pointe Dr, Holiday, FL 34691

    $10,000 price reduction, Nestled in the desirable, gated community of Key Vista, this exquisite 5-bedroom, 4-bathroom executive pool home with a 3-car garage offers both luxury and comfort. It's an exceptional value with NO CDD fees and an affordable HOA.Located just minutes from the water, this coastal gem offers a serene, picturesque lifestyle. All of the home's bedrooms and bathrooms

    Mena Antanios TRINITY REALTY

    2533 Wood Pointe Dr, Holiday, FL 34691
  • /74

    $189,900

    • 2 Beds
    • 2 Baths
    • 1,318 Sq Ft

    3849 Staysail Ln, Holiday, FL 34691

    One or more photo(s) has been virtually staged. The only opportunity to own a beautifully fully renovated first floor unit! Brand new everything!! Top of the line appliances, AC, water heater, ceramic tiles and engineering flooring throughout whole unit, all new tall cabinets in kitchen and baths with beautiful granite and very unique back splash in the kitchen. Modern colors to bring in the

    Anna Pikula RE/MAX MARKETING SPECIALISTS

    3849 Staysail Ln, Holiday, FL 34691
  • /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
  • /2

    $150,000

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

    4233 Darlington Rd, Holiday, FL 34691

    Auction Property. ***Auction will run April 21-May 1st*This 3 bedrooms and 2 bathrooms house is ready for its new owner or investor. Property has a tenant. . A buyer's premium of 5% is required. MUST preregister on the auction site prior to being approved to bid on the auction online! You may schedule an appointment to view and perform due diligence on the property prior to the auction close.

    Tony Kelly A BETTER LIFE REALTY

    4233 Darlington Rd, Holiday, FL 34691
  • /17

    $1,100,000

    • 4 Beds
    • 3 Baths
    • 2,787 Sq Ft

    5903 Cachette de Riviera Ct, New Port Richey, FL 34655

    HIGH & DRY, GULF ACCESS!! This stunning waterfront pool home is nestled on a cul-de-sac with over half an acre of beautifully manicured landscape. Located in the exclusive and very private gated community of Riviera, your slice of paradise awaits! The home boasts not one but TWO composite docks where you can enjoy breathtaking views of the Anclote River and incredible sunsets. The 8000 lb

    Jose Echevarria Jr. RIVIERA REALTY ASSOCIATES INC

    5903 Cachette de Riviera Ct, New Port Richey, FL 34655
  • /38

    $85,000

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    490 Becky Way, Tarpon Springs, FL 34689

    No Flood or Wind Damage Here. This Home is Located in a Non-Flood Zone in The Highly Sought After Meadows Community in Tarpon Springs. Enjoy the Luxury and Convenience of Tarpon Springs without the Worry of Flooding. New Hurricane Straps Were Installed on This Home in 2024. Brand New Heating and Air Conditioning System. This Home Has Recently Been Remodeled. New Luxury Vinyl Plank Floors

    Lisa Thomas American Mobile Home Sales of Tampa Bay, Inc.

    490 Becky Way, Tarpon Springs, FL 34689

Home Trends in Holiday, FL

Housing Trends

Median Sale Price
$237,000
Median Single Family Sale Price
$245,000
Median Townhouse Sale Price
$288,495
Median 2 Bedroom Sale Price
$149,900
Median 1 Bedroom Sale Price
$127,000
Average Price Per Sq Ft
$201
Number of Homes for Sale
250
Last 12 months Home Sales
693
Months of Supply
4.30
Median List Price
$255,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-3%
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