Holiday, FL Homes for Sale under $500,000

One or more photo(s) has been virtually staged. Welcome to 5313 Boardwalk Street — a beautifully updated 3 bedroom, 2.5 bath waterfront home offering incredible value in one of Holiday’s most desirable boating communities. This property experienced no flood damage from past hurricanes, providing peace of mind while enjoying true Florida waterfront living. Major systems have also been updated,

Jonathan Hernandez COLDWELL BANKER REALTY

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

Waterfront Living at its Finest – Nestled in a luxury, family-friendly neighborhood in Holiday, Florida. This stunning 3-bedroom, 2-bath waterfront home with nearly 1,900 sq ft. It offers the perfect blend of comfort, style, and a ultimate Florida boating lifestyle. This property is a true fisherman’s paradise with direct access to the Anclote River and just a short boat ride to the famous Tarpon

Shawn Miller PREMIER REALTY

PRICE REDUCTION!!!!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 everyday

Shawn Miller PREMIER REALTY

PRICED DROPPED! SELLER WILL HELP WITH 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

Whitney Boland SIGNATURE REALTY ASSOCIATES

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

“Attention investors and discerning buyers! This luxury property in Holiday is a once-in-a-lifetime opportunity just 7 min left to the beach! Completely rebuilt in 2026, everything is brand new: windows, doors, roof, air conditioning with modern lineal ducts—all completed in 2026. This home boasts a brand-new 2026 water heater, luxury ceramic bathrooms, and stunning ceramic flooring throughout.

Zuleidys Ares SELLING USA, LLC

PRICE ADJUSTMENT !! Totally renovated 3bedroom 2 bathroom 2 car garage home in quiet community. Roof, HVAC,Water Heater, Flooring, Kitchen and Bathrooms all brand new.Wood cabinets and stone counter tops in Kitchen and Bathrooms. Huge lot with vaulted screened in lanai. Low HOA covers community pool and cable.Come and make this charmer your new home!!!

Maria Gallace Gerelus LUXURY & BEACH REALTY INC

A Private, Park-Like Oasis with Unmatched Amenities Awaits! If you are afraid of nature, this might not be for you. Discover an unparalleled retreat where natural beauty meets modern convenience. Looking out at mature, leafy trees, this remarkable property features a serene pond and small stream. Sit by your firepit or cross over your charming bridge inviting serene moments of quiet reflection.

Bill Whiteside LPT REALTY, LLC

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

Welcome to this beautifully maintained pool home in the gated community of Key Vista, where residents enjoy a wide array of amenities, including a clubhouse, fitness center, tennis and pickleball courts, volleyball courts, a heated pool and spa, a playground, and numerous community events for all ages. As you enter the foyer, you’re greeted by high ceilings, an open floor plan, and abundant

Renee Gialousis COLDWELL BANKER REALTY

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

Unique large secluded property with 4 building lots located in North Pinellas County. Property has a private gated entry, featuring a detached garage, large workshop, storage shed and basketball court. The kitchen has granite countertops with stainless steel appliances and under mount sink. Spacious bathroom. Newer AC and hot water heater. Big patio. Tons of space for boats, trailers, and

Jorge Zea BLUE LIGHTHOUSE REALTY INC