27

Holiday, FL Homes for Sale under $500,000

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  • /29

    $464,900

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    5253 Boardwalk St, Holiday, FL 34690

    TRUE FLORIDA LIVING AT ITS BEST! Welcome to your waterfront oasis at 5253 Boardwalk Street in Holiday, Florida—where luxury meets lifestyle with direct Gulf access right from your backyard. This stunning 3-bedroom, 2.5-bathroom home has been completely rebuilt and reimagined with high-end finishes and thoughtful design throughout. From the moment you enter, you'll notice the open layout, filled

    Agent Photo

    Gigi Gauthier

    TRUE REALTY GROUP

    (727) 910-5580

    5253 Boardwalk St, Holiday, FL 34690
  • /28

    $450,000

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

    3022 Jackson Dr, Holiday, FL 34691

    Discover this stunning 4-bedroom, 2-bath residence nestled on a peaceful cul-de-sac with no front neighbors, offering unmatched privacy and tranquility. Sitting on over half an acre of land, this property is your perfect canvas to create the lifestyle you’ve always wanted.Soak up the Florida sunshine in your sparkling private pool, an entertainer’s paradise and a family retreat all in

    Rosalia Dieppa Rodriguez HOME PRIME REALTY LLC

    3022 Jackson Dr, Holiday, FL 34691
  • /43

    $445,000

    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft

    2718 Dolphin Watch Ct, Holiday, FL 34691

    Come live in Paradise! This gorgeous ONE-STORY home is located in the desirable community of Key Vista right in the heart of Holiday. Home Sweet Home! This amazing home offers 3 bedrooms, 2 full bathrooms, formal dining area, and a kitchen that opens to a large living. Once inside you will be greeted by an amazing open floor plan with high ceilings and open spaces. Welcome to the kitchen where

    Natalie Bailey MARK SPAIN REAL ESTATE

    2718 Dolphin Watch Ct, Holiday, FL 34691
  • /48

    $445,000

    • 3 Beds
    • 2 Baths
    • 1,647 Sq Ft

    2906 Windridge Dr, Holiday, FL 34691

    Welcome to 2906 Windridge Drive where peace of mind meets luxury living and you can catch morning sunrises over the lake to start your days off right ! This stunning waterfront dream home is proudly situated in a non-flood zone, ensuring that flood insurance is not required. This feature, combined with the home’s elevated position, offers unrivaled security and stability, even through recent

    Christopher Grasso BHHS FLORIDA PROPERTIES GROUP

    2906 Windridge Dr, Holiday, FL 34691
  • /40

    $445,000

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

    2325 Indian Key Dr, Holiday, FL 34691

    Beautifully renovated 4-bed, 3-bath home with a bonus room downstairs for an office!Enjoy brand NEW Flooring throughout, fresh interior & exterior paint, high ceilings.The spacious master suite offers double sinks, a garden tub, walk-in shower, and a HUGE walk-in closet with organizers. Major upgrades include a NEW Kitchen Cabinets & Appliances, NEW 2025 roof, 2023 AC, and 2024 solar

    Anthony Terrell SOUTH CEDAR REAL ESTATE, INC

    2325 Indian Key Dr, Holiday, FL 34691
  • /35

    $445,000

    • 4 Beds
    • 2.5 Baths
    • 2,259 Sq Ft

    3115 Gina Ct, Holiday, FL 34691

    Immaculate 4-Bedroom Home with Loft on Conservation Lot in Gated Community.Welcome to this immaculate 4-bedroom, 2.5-bathroom home with a spacious loft, ideally situated on a corner conservation lot in a desirable gated community. This move-in ready residence offers comfort, style, and peace of mind with NO flood insurance.The home features white kitchen cabinets with granite counter

    Scott Tomlinson FUTURE HOME REALTY INC

    3115 Gina Ct, Holiday, FL 34691
  • /56

    $469,900

    • 3 Beds
    • 3 Baths
    • 2,202 Sq Ft

    1913 Blue River Rd, Holiday, FL 34691

    Lakefront Pool Home in Gated Community – Not in a Flood Zone!Welcome to your private retreat in the heart of Holiday, Florida! This beautifully updated 3-bedroom, 3-bathroom home is located in a gated community and offers the best of Florida living—plus peace of mind, as it's in one of the few areas not located in a flood zone.Inside, you'll find new flooring throughout and a

    Jonathan Fitzgerald CHARLES RUTENBERG REALTY ORLANDO

    1913 Blue River Rd, Holiday, FL 34691
  • /71

    $475,000

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

    2321 Wood Pointe Dr, Holiday, FL 34691

    SELLER GIVING $10,000 TOWARDS BUYERS CLOSING COST! Welcome to 2321 Wood Pointe Drive, a spacious 4-bedroom, 3-bathroom home located in the highly sought-after Key Vista community in Holiday, Florida. This beautifully updated home features a large upstairs man cave/loft space, perfect for entertainment or relaxation. With a NEW ROOF JUST INSTALLED, newer A/C, and an energy-efficient tankless water

    Whitney Boland SIGNATURE REALTY ASSOCIATES

    2321 Wood Pointe Dr, Holiday, FL 34691
  • /43

    $480,000

    • 4 Beds
    • 3 Baths
    • 2,525 Sq Ft

    3138 Deergrass Ct, Holiday, FL 34691

    Short Sale. Welcome to 3138 Deergrass Ct, nestled in the charming Glenwood of Gulf Trace neighborhood. This beautifully designed home offers a spacious and thoughtful layout, perfect for families or those who love to entertain.Step outside to enjoy the mature landscaping that enhances the curb appeal, along with a fully fenced backyard featuring a heated pool and spa—a private oasis for

    Renee Gialousis COLDWELL BANKER REALTY

    3138 Deergrass Ct, Holiday, FL 34691
  • /48

    $469,000

    • 4 Beds
    • 2 Baths
    • 1,955 Sq Ft

    378 Wood Chuck Ave, Tarpon Springs, FL 34689

    This is your opportunity to own a beautifully updated, move-in ready 4-bedroom, 2-bathroom home with a 3-car garage in the highly desirable gated community of Forest Ridge in Tarpon Springs. Offering nearly 2,000 square feet of well-designed living space, this meticulously maintained home blends comfort, style, and function.As you step inside, you’ll immediately notice the high ceilings,

    Renee Gialousis COLDWELL BANKER REALTY

    378 Wood Chuck Ave, Tarpon Springs, FL 34689
  • /34

    $459,990

    • 4 Beds
    • 3 Baths
    • 1,940 Sq Ft

    1839 Sunrise Dunes Ct, Tarpon Springs, FL 34689

    Come to see this beautifully renovation 4 Bedroom 3 Bath property today before it's too late! New Open Floor Kitchen/Bath! New Tile Flooring! New Paint! New roof before closing! New Fenced in patio area and so much more! Have the privacy of Mother in Law suit with a separate exit! NO CDD, Low HOA! This property is located close to all of Florida's beautiful amenities, Tarpon Springs sponge

    Lena Tan BHHS FLORIDA PROPERTIES GROUP

    1839 Sunrise Dunes Ct, Tarpon Springs, FL 34689
  • /26

    $460,000

    • 6 Beds
    • 4 Baths
    • 1,972 Sq Ft

    1839 & 1841 Hacienda Way, Holiday, FL 34690

    Four units in two duplex buildings on one lot. 1839 has an efficiency and a 2-1 unit with central air. 1841 is two 2-1 units both with newer central air in both. All four units are rented month to month. There is plenty of opportunity to rent them long term at higher rental amounts. No sign, do not disturb tenants. Interior inspection of all units available once under contract.

    Mark Wimmer PLLC KELLER WILLIAMS REALTY- PALM H

    1839 & 1841 Hacienda Way, Holiday, FL 34690
  • /66

    $400,000

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

    2651 San Luis Rd, Holiday, FL 34691

    Waterfront home with pool, swim spa, and private sandy beach! This 3BR/2BA home with a 2-car garage features an open floor plan filled with natural light. Enjoy a spacious custom deck, private boat dock, and backyard retreat with an above-ground pool, relaxing swim spa, and enclosed patio. The yard is a tropical paradise with papayas, star fruit, grapevines, and a huge mulberry tree out front.

    Shawn Stanley STANLEY REALTY SERVICES LLC

    2651 San Luis Rd, Holiday, FL 34691
  • /71

    $499,000

    • 4 Beds
    • 3 Baths
    • 2,188 Sq Ft

    2807 Banner Stone Ct, Holiday, FL 34691

    Welcome to this stunning 4-bedroom, 3-bathroom home located in the desirable Key Vista community in Holiday, FL. This spacious single-family residence offers 2,188 sq. ft. of heated living space and a total area of 3,061 sq. ft., situated on a 0.21-acre lot. The home features a welcoming open floorplan with a bright living room, family room, and a generous kitchen perfect for entertaining. The

    Daniela Silvesrtone LPT REALTY, LLC.

    2807 Banner Stone Ct, Holiday, FL 34691
  • /49

    $410,000

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

    3030 Shadow Oaks Dr, Holiday, FL 34690

    Opportunity knocks in Shadow Oaks! This spacious 3-bedroom, 2.5-bath, two-story pool home sits on a desirable corner lot at the end of two dead-end streets, providing ultimate privacy and no through traffic, and offers 2,510 sq. ft. of living space (3,799 total sq. ft. footprint) with an oversized three-car garage for storage, hobbies, or a workshop. The smart layout features a separate laundry

    Erin Gwillim PIECE OF PARADISE REALTY

    3030 Shadow Oaks Dr, Holiday, FL 34690
  • /53

    $494,900

    • 5 Beds
    • 3 Baths
    • 2,500 Sq Ft

    2637 Timacqua Dr, Holiday, FL 34691

    Homes like this don’t last long—come see it for yourself and fall in love! PRICED BELOW MARKET VALUE!! This stunning 5-bedroom, 3-bathroom home sits on a private conservation lot with no rear neighbors, offering exceptional privacy and peaceful nature views. No flood insurance required! Located in a gated community, the home welcomes you with engineered hardwood flooring and a beautiful view of

    Hector Contreras WEICHERT REALTORS EXCLUSIVE PROPERTIES

    2637 Timacqua Dr, Holiday, FL 34691
  • /23

    $499,000

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft

    4233 Flora Ave, Holiday, FL 34691

    Live and Work on Site! Versatile Commercial Property with Home, Office, and Workshop Don’t miss this unique opportunity to own a mixed-use property zoned C2 and R1, perfectly suited for entrepreneurs looking to live and operate a business on-site. Situated on a spacious 1⁄2 acre lot just behind Home Depot, this property offers incredible visibility and convenience. The property features a

    Max Upchurch UPCHURCH REALTY LLC

    4233 Flora Ave, Holiday, FL 34691
  • /37

    $489,900

    • 3 Beds
    • 2 Baths
    • 2,196 Sq Ft

    3311 Hearthstone Ct, Holiday, FL 34691

    Your Private Retreat with New Roof & Entertainer’s Backyard! Welcome to a move-in ready 3-bedroom, 2-bath home located in a peaceful, well-kept neighborhood. This beautifully maintained residence features a brand-new shingle roof, a thoughtfully designed open floor plan, and a fully fenced backyard with a caged pool perfect for entertaining year-round.Inside, you’ll find two spacious

    Patrycja Henderson LUXURY & BEACH REALTY INC

    3311 Hearthstone Ct, Holiday, FL 34691
  • /41

    $424,000

    • 4 Beds
    • 2 Baths
    • 2,869 Sq Ft

    2030 Norfolk Dr, Holiday, FL 34691

    Lakefront Living at Its Finest Spacious & Updated Home on Lake Conley. Enjoy peaceful waterfront living in this beautifully maintained expansive ten room home featuring 4-bedroom, 2 bath + great room, offering 2, 869 sq ft of upgraded comfort in the desirable community of Holiday Lake Estates. Step inside to discover a bright and open layout featuring tile flooring throughout (2021), vaulted

    Alex Ciumasu TAMPA4U.COM REALTY,LLC

    2030 Norfolk Dr, Holiday, FL 34691
  • /53

    $420,000

    • 4 Beds
    • 3 Baths
    • 2,202 Sq Ft

    2654 Banner Stone Ct, Holiday, FL 34691

    Fresh and beautiful, move-in ready 4 Bedroom 3 Bathroom home with a Conservation View in Key Vista. There is NO CDD fee and includes TONS OF UPGRADES and UPDATES! Full ROOF replacement in 2023 and there is Beautiful Bamboo Hardwood Flooring in the main living areas. When you walk in you will notice the nice remodel and excellent window placement allowing for plenty of natural light. The open

    Paul Farr AGILE GROUP REALTY

    2654 Banner Stone Ct, Holiday, FL 34691
  • /41

    $410,000

    • 4 Beds
    • 2 Baths
    • 2,027 Sq Ft

    2511 Indian Key Dr, Holiday, FL 34691

    One or more photo(s) has been virtually staged. PRICE IMPROVEMENT | NEW ROOF INSTALLED | MOTIVATED SELLER | $2,000+ RENTAL POTENTIAL!Welcome to this beautifully maintained 4-bedroom, 2-bath home with over 2,000 sq ft of living space, an extended 2-car garage, and a brand-new roof just installed for peace of mind. Located in a gated, resort-style community, this home features two primary

    Sandra Keroles COLDWELL BANKER REALTY

    2511 Indian Key Dr, Holiday, FL 34691
  • /74

    $440,000

    • 3 Beds
    • 2.5 Baths
    • 2,620 Sq Ft

    2614 Hawk Roost Ct, Holiday, FL 34691

    (MOTIVATED SELLER) Immaculate Move-In Ready Home in Sought-After Key Vista Community!Nestled on a peaceful cul-de-sac in the gated Key Vista community, this beautifully maintained 3-bedroom, 2.5-bath single-family home offers the perfect blend of comfort, style, and thoughtful upgrades. From the moment you enter, you'll appreciate the open-concept layout, ideal for both entertaining and

    Javi Lopez-Munoz SMITH & ASSOCIATES REAL ESTATE

    2614 Hawk Roost Ct, Holiday, FL 34691
  • /41

    $419,990

    • 3 Beds
    • 2 Baths
    • 2,027 Sq Ft

    2641 Big Pine Dr, Holiday, FL 34691

    NEW PRICE! Welcome to your dream home in the highly sought-after Key Vista Community of Holiday, FL! This stunning property boasts three spacious bedrooms, two bathrooms, and a versatile flex room that can easily serve as an additional bedroom, office, or entertainment space. As you step outside, you'll be captivated by the serene pond views and breathtaking sunsets from the covered back porch,

    Sarahi Terreforte Rivera REAL BROKER, LLC

    2641 Big Pine Dr, Holiday, FL 34691
  • /4

    $449,900

    • Land
    • 8.75 Acres
    • $51,417 per Acre

    1318 Classic Dr, Holiday, FL 34691

    BIGGEST WATERFRONT LOT in the Holiday market. This 8.75 acre lot sits on 6.75 acres lake, 2 acres land and priced to sell. Property is being sold for Cash "As is". Zoned for R4 the property in near Lake Nash situated in Lake Holiday Estates neighborhood. Geared towards Land Flippers, Developers and builders.

    Scott Fader JOSEPH WALTER REALTY LLC

    1318 Classic Dr, Holiday, FL 34691
  • /8

    $427,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    2713 San Luis Rd, Holiday, FL 34691

    Under Construction. Welcome to 2713 San Luis Rd, Holiday, FL – your opportunity to own a brand-new, modern home with the chance to make it uniquely yours! Currently under construction, this stunning 3-bedroom, 2-bathroom home with a spacious 2-car garage offers contemporary design and endless potential.Why wait for the perfect home to appear when you can create it? The builder is offering

    Giancarlo Gonzalez 3 POINT REAL ESTATE SOLUTION

    2713 San Luis Rd, Holiday, FL 34691
  • /19

    $437,700

    • 5 Beds
    • 3 Baths
    • 3,134 Sq Ft

    2707 Wood Pointe Dr, Holiday, FL 34691

    Auction Property. AUCTION. This affordable ranch home offers 5 beds, 3 baths, separate living and dining areas, and an open kitchen. Enjoy your outdoor space on the large covered patio, with an attached Lanai and in ground pool. The home offers a 3 car garage and ample space to relax and entertain. Property is sold as-is with NO property disclosure or inspection reports. Make this one your dream

    Andrea Butcher Thomas REALHOME SERVICE & SOLUTIONS INC

    2707 Wood Pointe Dr, Holiday, FL 34691
  • /39

    $435,000

    • 4 Beds
    • 2 Baths
    • 2,110 Sq Ft

    1948 Wood Brook St, Tarpon Springs, FL 34689

    Step into your dream home where space meets comfort and enjoy peace of mind with no flood insurance required! This spacious residence boasts a versatile split floor plan adorned with stunning vaulted ceilings throughout. It's the perfect backdrop for family living and entertaining friends. Key Features include four comfortable Bedrooms & Two Full Baths. Plenty of room for everyone, giving you the

    Ray Mullins FLORIDA HOMES REALTY & MORTGAGE

    1948 Wood Brook St, Tarpon Springs, FL 34689

Home Trends in Holiday, FL

Housing Trends

Median Sale Price
$235,935
Median Single Family Sale Price
$245,000
Median Townhouse Sale Price
$279,000
Median 2 Bedroom Sale Price
$140,000
Median 1 Bedroom Sale Price
$122,250
Average Price Per Sq Ft
$199
Number of Homes for Sale
257
Last 12 months Home Sales
776
Months of Supply
4.00
Median List Price
$258,450
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-2%
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