In the early 20th century, Oldsmar began as a planned community with roots in the automotive industry. Today, it is a small town between downtown Tampa and Clearwater. Oldsmar is a community of convenience with waterfront living in the center of the Tampa Bay. City parks and hiking trails sit in rich marsh ecosystems on the ocean. Being only a short drive from multiple cities, this town has access to some of Florida's best schools and most exciting attractions. Despite the action happening nearby, Oldsmar has the homey atmosphere of a small town with a population of around 13,600 and events that bring the community together.
Relax and take in the sun at Mobbly Beach in Oldsmar.
Kids are excited to play in the parks of Oldsmar.
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Oldsmar parks system and the trail
“Oldsmar boasts more parks per square mile than any other city in the State of Florida, with about 40% of its land dedicated to either a park or preserve,” says Debb Vitraelli, Public Communications Supervisor of Oldsmar. “For context, the average city has less than 10%, according to the Trust for Public Land. Parks provide measurable health benefits from direct contact with nature, opportunities for physical activity and social interaction during our many events.” The Oldsmar Trail is a ten-mile nature walk beginning at the Oldsmar Sports Complex and moving down the coast through eight of the city’s ten parks. The trail includes an ambient path on a wooden bridge through Cypress Forest and quiet swamps in Moccasin Creek. R.E. Olds Park is a peaceful spot with a long wooden fishing pier, a large playground, walking trails and an outdoor amphitheater. Veterans Memorial Park has a waterfront view with outdoor exercise equipment and a pavilion. On warm days, residents can visit the Mobbly Bayou Beach Park, a small beach with sunset views.
Oldsmar has a few pickleball leagues for anybody to join.
The Oldsmar trail runs through Oldsmar, and connects with many other locations.
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Flea Market, Days and Nights and Oktoberfest
The Oldsmar Flea Market claims to be the “largest flea market in the south,” with over 280 vendors open mornings from Wednesday through Sundays. The Oldsmar Days and Nights festival is an annual event with beer gardens, live rock 'n' roll and classic car shows. Oktoberfest takes place in Oldsmar and has authentic German beer and cuisine.
Several local bands perform at Bands and Brews by the Bay in Oldsmar.
Bands and Brews by the Bay has a great car show.
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Travel between cities on Tampa Road
Tampa Road runs through the heart of town, taking traffic 11 miles west on State Street to Clearwater or 16 miles east to downtown Tampa. The Tampa International Airport is only 11 miles southeast. The Pinellas Suncoast Transit Authority (PTSA) bus system provides public transportation with stops along Tampa Road. Ferries take passengers on daily trips across the bay to islands. Boats are a popular mode of transportation as the Old Tampa Bay touches the shore.
Pinellas County Schools, top-tier education
The school district in Oldsmar is Pinellas County Schools. According to Niche, Pinellas County is the best school district in the Tampa area, with an A-minus overall Niche grade. In the top 10 of Florida's most diverse school districts, Pinellas encompasses the western peninsula, stretching down through St. Petersburg and the Gulf islands. Palm Harbor University High School is located eight miles northwest and has an overall Niche grade of A. It is rated the 2nd best high school in the county and in the top 100 best public high schools for STEM in Florida. The Primrose School of Oldsmar is an education and daycare center for infants and toddlers. Center Academy Palm Harbor has an excellent special education program for kids with distinctive learning requirements.
East Lake High School has 2,326 students in grades PK, 9-12.
Joseph L. Carwise Middle has 1,155 students in grades 6-8.
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Farmstead estates and luxurious multifamily communities
Real estate in Oldsmar dates back to the 1920s when many single-family homes were rebuilt after a hurricane. Housing styles in Oldsmar include ranch-style homes with hipped roofs, single-story craftsman builds and sprawling farmstead estates. Homes sit on generous green lots with palm trees covered in Spanish moss. Many higher-end homes have in-ground pools. Townhouses and waterfront condos are set up in luxurious communities around town. Homes in Oldsmar typically sell after only 38 days on the market compared to the national average of 42 days. Based on data from the last 12 months, homes sell at an average price of $438,730, down 6% from the average home sale price over the previous year.
Many higher-end homes have in-ground pools and sit on generous green lots with palm trees in Oldsmar.
Single-family ranch style houses are a dime a dozen in Oldsmar.
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Retail and local attractions
Residents will find a large selection of local shops, restaurants and box stores along Tampa Road. Groceries can be found at ALDI and Walmart Supercenter, both located in the shopping center off Forest Lakes Boulevard. The city is redeveloping a downtown area with shops, restaurants and residential space on an 8-acre site next to City Hall. The goal of this development is to stimulate the local economy and make the area more sustainable while maintaining its small-town charm.
Just east of Oldsmar is the Tampa Bay Downs. Established in 1926, this thoroughbred horse racing track has a poker room and a golf practice area for residents looking to try their luck. HorsePower is a nonprofit farm and animal sanctuary where kids can interact with goats and go horseback riding. Thrill seekers can venture to Empower Adventures Tampa Bay to zipline 60 feet above the or traverse an aerial obstacle course. The Tampa Bay Skating Academy offers figure skating and hockey lessons to newcomers, and it has a public ice rink.
The Aldi store in Oldsmar, offers great deals on produce for customers.
Tampa Bay Downs in Oldsmar is a world class horse track with a Derby qualifier.
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Other information
Oldsmar has a B rating from CrimeGrade, making it safer than the average city. The crime rate includes 8.2 property crimes reported per 1,000 residents during a standard year and 2.1 violent crimes reported per 1,000 residents. Violent crimes are infrequent in Oldsmar. Based on the number of crimes reported, the northern part of town is the safest. Based on a Flood Insurance Study by the Federal Emergency Management Agency (FEMA), much of southern Oldsmar is subject to flood risks. The area south of Tampa Road has a 26% chance of flooding over the next 30 years. The city participates in the National Flood Insurance Program and encourages residents to do the same. Some neighborhoods have a disaster plan that meets their distinctive needs based on where they are in town, so it’s important for residents to stay informed about weather, safety precautions and the flood risk on their property. The ALERT Pinellas emergency notification will inform participating residents of severe weather and mandatory evacuations.
Written By
Hannah Rainey
Photography Contributed By
David Hall
Video By
Scott Wiggins
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GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Oldsmar, FL sell after 61 days on the market compared to the national average of 52 days. The median sale price for homes in Oldsmar, FL over the last 12 months is $370,000, down 8% from the median home sale price over the previous 12 months.
OPPORTUNITY KNOCKS In this POTENTIAL-FILLED 4 BEDROOM 2.5 BATH- PRIME TAMPA BAY LOCATION!Rare opportunity in sought-after Tampa Bay location just ONE BLOCK from beautiful waterfront and R.E. Olds Park! This spacious multi-level home offers tremendous potential for the right buyer with vision. Featuring four bedrooms, 2.5 baths, and an impressive 3-car garage with workshop space, this
Fully updated and move-in ready 3-bedroom, 2.5-bath townhome in highly desirable Hayes Park Village. Built in 2016, this home offers modern finishes throughout, including luxury plank vinyl flooring, updated bathrooms, granite countertops, stainless steel appliances, and wood cabinetry. Crown molding adds an elegant touch to the downstairs living area, while modern lighting and ceiling fans are
Welcome home to Kingsmill at East Lake Woodlands, a highly sought-after community in Oldsmar, Florida. Enter this exquisite, gated community that beautifully blends refined living with a sense of serene retreat. Nestled among lush nature preserves and world-class golf courses, this community offers residents an unparalleled lifestyle of privacy, elegance and leisure. With its prime location near
Welcome to this Beautifully UPDATED 1296 sq ft, 2-bedroom, 2-bath villa with VAULTED CEILINGS and Stunning 24" CERAMIC TILE THROUGHOUT with a Bright OPEN floor plan. The Kitchen features GRANITE Countertops, WOOD Cabinets, and STAINLESS STEEL APPLIANCES. BOTH BATHROOMS have been tastefully UPDATED, and a convenient INSIDE LAUNDRY closet includes a NEW Washer purchased in 2025 (conveys with sale).
This spacious, contemporary residence offers the perfect blend of luxury and comfort, whether you're looking for a permanent home or a winter getaway. Every detail has been thoughtfully upgraded, featuring custom cabinetry, a beautiful leaded glass front door, sleek stainless-steel appliances, and a spacious kitchen island. Enjoy modern conveniences like a front-loader full-size washer and dryer,
Charming 2-bedroom, 2-bath villa in the desirable Sheffield Village at Bayside Meadows community. Spacious layout with vaulted ceilings and fenced yard perfect for relaxing or entertaining. Affordable HOA around $100/month covers maintenance. Built in 1986 with solid bones, this home offers great potential for first-time buyers or investors looking for a well-priced opportunity in Oldsmar. Don’t
Gated East Lake Woodlands golf community this private Greenhaven subdivision residence features a 3-way split bedroom floor plan with 4 bedrooms, 3 bathrooms, a 3 car garage with a private oversized yard and screened enclosed pool and spa. Front double leaded glass doors, formal living and dining; kitchen and family room combination; inside utility; office off front entry hall; primary bedroom
Stunning Waterview Condo in the Gated Community of East Lake Woodlands! Experience low-maintenance, resort-style living with serene pondviews in this beautifully updated, ground-floor residence located in one of the area’s most coveted gated communities. Light and airy throughout,this stylish home features durable plank tile flooring and a desirable split-bedroom layout, perfectly blending
Nicely updated two-story townhome with a one-car garage, available for rent starting October 1st! All bedrooms are carpeted and upstairs. The primary suite has its own bathroom. Both guest rooms share the full hall bathroom which offers a tub and single sink. Downstairs, the kitchen adjoins the family room which features sliders to the screened lanai that overlooks conservation and a pond!
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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
