14

Holiday, FL Homes for Sale under $800,000

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  • /17

    $699,900

    $79K PRICE DROP
    • Land
    • 5 Acres
    • $139,980 per Acre

    0 Silhouette Ln Unit MFRTB8320392, Holiday, FL 34691

    Discover a rare opportunity to own 5 pristine acres on Lake Conley, just minutes away from Tarpon Springs and the World Famous Sponge Docks. With abundant wildlife and natural beauty, this vacant land is the perfect canvas for creating your dream home or private compound. Zoned AR5 and positioned with favorable future land use, this property offers both flexibility and potential for custom

    Agent Photo

    Michael Pappas

    PAPPAS REAL ESTATE LLC

    0 Silhouette Ln Unit MFRTB8320392, Holiday, FL 34691
  • /31

    $799,000

    • Land
    • 1.46 Acres
    • $547,260 per Acre

    0 Flotilla Dr Unit MFRTB8498330, Holiday, FL 34690

    Total of 1.4675 acres, 2 parcels of land. Owner will not sell properties individually. Nestled on the shimmering Anclote River in prime territory in Holiday, Florida. Situated on a waterway that leads out to the Gulf. Located on a coveted cul-de-sac, 200 feet of water frontage is retained by an existing seawall and encircled by trees for privacy. The property has direct views of a conservation

    Agent Photo

    David Crawford

    RE/MAX ACTION FIRST OF FLORIDA

    0 Flotilla Dr Unit MFRTB8498330, Holiday, FL 34690
  • /34

    $599,990

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

    1238 Flotilla Dr, Holiday, FL 34690

    PRICED TO SELL * HERE'S ANOTHER OPPORTUNITY TO PURCHASE THIS UNIQUE AND MAGNIFICENT WATERFRONT HOME, SURROUNDED ON THREE SIDES BY SPECTACULAR WATER VIEWS * THIS HOME WITH SPANISH AND MEDITTERANEAN ARCHITECTURE, FEATURES SUCH AS BEAMED CEILINGS AND ARCHED OPENINGS THROUGHOUT IS VERY SPACIOUS AND HAS AN ATTRACTIVE LAYOUT ON TWO FLOORS * TWO MASTER BEDROOMS, EACH ACCESSED BY TWO SEPARATE STAIRWAYS

    Theresa Legatti CHARLES RUTENBERG REALTY INC

    1238 Flotilla Dr, Holiday, FL 34690
  • /44

    $575,000

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

    1914 Oswego Dr, Holiday, FL 34691

    Welcome to this beautiful 5 bedroom 3 bathroom two-story home located in the highly desirable community of Key Vista. Upon entry you immediately feel welcome and at home with the large formal dining area and front living area with electric fireplace. The large kitchen boasts tall cabinetry and plenty of counter space with amazing views of the tree line that reflects along the waters edge. One

    Jason Scott INVESTMENT FLORIDA REALTY LLC

    1914 Oswego Dr, Holiday, FL 34691
  • /5

    $799,000

    • Land
    • 10.47 Acres
    • $76,313 per Acre

    5001 Whippoorwill Dr, Holiday, FL 34690

    West of Grand Blvd. at the end of Whippoorwill Dr. Forested Property, Suitable for a Private Estate Home,(Compound), Water feature, Paved Access, Utilities Available

    John Grey FI GREY & SON INC COMMERCIAL

    5001 Whippoorwill Dr, Holiday, FL 34690
  • /37

    $524,900

    $25K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,429 Sq Ft

    1908 Oswego Dr, Holiday, FL 34691

    This stunning 5 bedroom 3 bathroom home sits on a serene and tranquil pond in the heart of the exclusive gated community of Key Vista. This well maintained property features a luxurious kitchen with stunning granite counter tops, extra large island, and beautiful wood cabinets. Stylish wood plantation shutters throughout adds the perfect compliment. You and your guests will enjoy the massive 3

    Jason Scott INVESTMENT FLORIDA REALTY LLC

    1908 Oswego Dr, Holiday, FL 34691
  • /9

    $799,000

    • Land
    • 15,246 Sq Ft
    • $2,282,857 per Acre

    000 Bluff Blvd, Holiday, FL 34691

    "BUILD YOUR DREAM HOME" on this exceptional Gulf-front property featuring 80 feet of direct water frontage and an impressive 206-foot depth. Perfectly positioned in the highly sought-after community of Baileys Bluff, this rare homesite is nestled within a true nature sanctuary, offering privacy, tranquility, and breathtaking coastal beauty. From your newly constructed home, you’ll enjoy

    Steve DeMatos RE/MAX ALLIANCE GROUP

    000 Bluff Blvd, Holiday, FL 34691
  • /63

    $579,000

    Open Sun 2PM - 4PM $21K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,367 Sq Ft

    3020 Sheppards Crook Ct, Holiday, FL 34691

    "Luxury Living in an Exclusive Gated Community" Experience coastal elegance in this custom-built executive residence, privately situated on a quiet cul-de-sac within an exclusive gated community. Offering 2,367 square feet of thoughtfully designed living space, this exceptional three-story home combines luxury, comfort, and functionality with partial Gulf views from multiple balconies. From the

    Steve DeMatos RE/MAX ALLIANCE GROUP

    3020 Sheppards Crook Ct, Holiday, FL 34691
  • /48

    $525,000

    $80K PRICE DROP
    • 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
  • /77

    $799,000

    $51K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 2,280 Sq Ft

    2030 Gulfview Dr, Holiday, FL 34691

    "Gulf Access Waterfront Home in Historic Baileys Bluff Estates" A rare opportunity to own a true waterfront gem with your own private boat ramp! Enjoy a quick 2-minute boat ride to the open Gulf and just 10 minutes more to Anclote Island—perfect for boating, fishing, and island adventures. This beautifully maintained 2-bedroom, 2-bath split floor plan home offers an open and inviting layout ideal

    Steve DeMatos RE/MAX ALLIANCE GROUP

    2030 Gulfview Dr, Holiday, FL 34691
  • /56

    $509,000

    $16K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,047 Sq Ft

    3318 Pineview Dr, Holiday, FL 34691

    NEVER FLOODED DURING HURRICANE HELENE! This is a rare opportunity to own a Gulf-access waterfront home that offers both an exceptional boating lifestyle and added peace of mind. According to the seller, the home has never experienced flooding or water intrusion, making it an outstanding choice for buyers seeking waterfront living with confidence. Nestled in the highly desirable Baileys Bluff

    Steve DeMatos RE/MAX ALLIANCE GROUP

    3318 Pineview Dr, Holiday, FL 34691
  • /57

    $550,000

    • 4 Beds
    • 3 Baths
    • 2,462 Sq Ft

    2309 Swordfish Ave, Holiday, FL 34691

    Welcome to 2309 Swordfish Ave, a beautifully maintained 4-bedroom, 3-bathroom, 2,462-square-foot single-story home situated on a spacious 10,320-square-foot lot in the desirable Gulfwinds community of Holiday, Florida. Offering an ideal combination of comfortable living space, thoughtful updates, privacy, and exceptional outdoor amenities, this home is designed for both everyday living and

    Gregory Palumbo KELLER WILLIAMS REALTY- PALM HARBOR

    2309 Swordfish Ave, Holiday, FL 34691
  • /60

    $575,000

    $35K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,857 Sq Ft

    3225 Glenwood Cir, Holiday, FL 34691

    Welcome to this spacious 4-bedroom, 3-bath pool home offering approximately 2,857 square feet of comfortable living space in the desirable Gulf Trace community of Holiday. Designed with both everyday living and entertaining in mind, the home features a split-bedroom floor plan, an expansive family room with a cozy fireplace, a generous kitchen with abundant cabinetry, a bright breakfast nook, a

    Jocelyn Carbonelli VANDERLEELIE & ASSOC.RE ESTATE

    3225 Glenwood Cir, Holiday, FL 34691
  • /68

    $539,999

    $60K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,589 Sq Ft

    1291 Blackrush Dr, Tarpon Springs, FL 34689

    This spacious 2-story home offers 4 bedrooms, 2.5 bathrooms, and approximately 2,589 square feet of thoughtfully designed living space.Step inside to soaring ceilings and an inviting open floor plan that flows seamlessly from formal living and dining areas to a generous family room. The updated kitchen features granite counters, tile backsplash, and stainless-steel appliances, perfect for

    Matthew Hughes CHARLES RUTENBERG REALTY ORLANDO

    1291 Blackrush Dr, Tarpon Springs, FL 34689

Home Price Trends

Median Sale Price
$229,900
Median Single Family Sale Price
$240,000
Median Townhouse Sale Price
$260,000
Median 2 Bedroom Sale Price
$210,000
Median 1 Bedroom Sale Price
$114,900
Average Price Per Sq Ft
$193
Number of Homes for Sale
239
Last 12 months Home Sales
624
Months of Supply
4.60
Median List Price
$250,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-2%
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