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
Interested in learning more about homes in this area?
Reach out to
James Wheeler,
an experienced agent in this area.
GreatSchools:
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On average, homes in Oldsmar, FL sell after 75 days on the market compared to the national average of 54 days. The median sale price for homes in Oldsmar, FL over the last 12 months is $370,000, down 7% from the median home sale price over the previous 12 months.
One or more photo(s) has been virtually staged. Enjoy easy Florida living in this beautifully updated 2-bedroom, 2-bath second-floor condo in the heart of Oldsmar. The home features luxury flooring throughout, a new HVAC system, and a comfortable open layout designed for both relaxing and entertaining. Step onto your private balcony overlooking peaceful green space — the perfect spot for morning
One or more photo(s) has been virtually staged. Priced to sell! Welcome to this charming first-floor 2 bedroom, 2 bath condo located in the heart of Oldsmar. This bottom-unit residence features a front-facing patio, perfect for enjoying your morning coffee or relaxing in the evenings. The condo offers newer appliances and a functional floor plan with great natural light throughout. An excellent
Perfection and CHARM has arrived in popular Oldsmar, FL. This AMAZING 6 bedroom, 3 full bathroom two-story corner lot home is nothing short of dreamy. With a full privacy fence, new exterior paint and new carpet, a spacious screened in lanai WITH HURRICANE/SAFE ROOM, you can not let this pass you by. Step inside to a majestic entryway and a floor plan with a purpose. To your right, you have a
PRICE REDUCTION! Now priced below value, this is your chance to own this incredible Key West style pool home on an oversized conservation lot in highly desirable Oldsmar. Located on a cul de sac with no through traffic on nearly an acre of land, with lush tropical landscaping backing up to forested conservation for added privacy. At the main entry is an inviting wraparound porch. Step inside the
Virtually Staged some photos. Price Reduction!! Attention all Golfers and Tennis players Dream in East Lake Woodlands that showcases 2 Championship 18 hold golf courses and 14 HAR-Tru tennis courts with no membership required!!.Newly remolded Patio Home with 2 bedroom 2 full bathroom with possible office/dining area in the Golf Course Community of East Lake Woodlands. This meticulously maintained
Experience coastal luxury and step into a lifestyle of refinement in this stunning 3-bedroom, 2.5-bath, 2 car garage townhome, nestled within the impressive gated waterfront enclave of Bayside Terrace! Curb appeal draws you into an open-concept layout designed for seamless entertaining with 10’ ceilings and beautiful tile flooring. The gourmet kitchen is a showstopper, featuring tons of cabinets,
INCREDIBLE VALUE FOR THIS SPACIOUS HOME. The Time is NOW to own your place in the Florida sun. This contemporary residence offers the perfect blend of luxury and comfort, whether you're looking for a permanent home or a winter getaway. Enjoy modern conveniences like the island kitchen, vaulted ceilings, a front-loader full-size washer and dryer, electric window blinds, and a newer roof and A/C
Wake up to million-dollar views, and unwind with spectacular sunsets - this is the waterfront lifestyle you've been waiting for. This updated 4-bedroom, 3-bath pool home sits directly on Tampa Bay on an oversized lot along iconic Shore Drive in Oldsmar. Enjoy panoramic water views across the Bay from a home that's high and dry - built on an elevated slab that has never flooded, eliminating the
No rear neighbors. Backs up to Briar Creek and trees. This lovely home is in a great quiet location and allows a cat or a dog up to 25 pounds. It has newer windows, new HVAC Jan 20/2025, replaced subfloors and installed luxury vinyl, replaced electrical panel Jan 2026, repaired vapor barrier & plumbing underneath & raised HVAC ducts that were hanging down. A 4 Point Inspection was done Jan 2026
One or more photo(s) has been virtually staged. Located inside the highly desirable gated community of East Lake Woodlands, this spacious 4-bedroom, 2.5-bath residence offers an expansive 2,922 sq ft of living space on an oversized lot with peaceful water views.Step inside to soaring ceilings and an open, light-filled floor plan designed for both everyday living and entertaining. The home
One or more photo(s) has been virtually staged. NO HOA! MARVELOUS WATER VIEW FROM YOUR BALCONY! Beautiful 2BR 2.5BA two-story townhouse in Oldsmar, FL. Master bedroom has French doors that open to a wonderful water view right in your backyard....enjoy the view of two lakes and a creek with stunning wildlife! Best of all, you get to rest assured that your property is high and dry, NO WATER
The Prettiest Home in Gull Aire – Turn-Key Perfection!Welcome to the crown jewel of Gull Aire, widely considered the most beautiful home in the entire community. This meticulously renovated 3-bedroom, 2-bathroom residence has been reimagined inside and out to offer the perfect blend of modern luxury and cozy community charm. If you are a social-seeking senior looking for a vibrant lifestyle
Welcome to 358 Lake Way in Gull-Aire Village, a desirable 55+ active golf cart community in Oldsmar where you own the land and enjoy a low $70/month HOA. This beautifully maintained 1998 Jacobson home offers 3 bedrooms, 2 bathrooms, and 1,296 sq ft of heated living space with over $40,000 in upgrades and improvements completed since 2023. Step inside to a bright and inviting interior featuring
Welcome to elevated living in the heart of Oldsmar! This beautifully maintained 3-bedroom, 2.5-bath townhome by Taylor Morrison blends modern style, thoughtful upgrades, and a peaceful natural setting — all within a gated community. Step inside to a bright, open layout perfect for everyday living and entertaining. The stunning kitchen is a true centerpiece, featuring stainless steel appliances,
PRICE IMPROVEMENT! LUXURY MEETS UNBEATABLE VALUE. Skip the rehab and move right in to the most updated waterfront townhome in the gated community of Seaside Estates. This beautifully maintained three-story home radiates pride of ownership and offers three bedrooms, three bathrooms, and over 1,800 square feet of thoughtfully designed living space. Premium features include IMPACT WINDOWS, IMPACT
Welcome to this beautifully maintained 2-bedroom, 1.5-bath townhouse, located in the heart of Oldsmar. Step inside to a spacious open-concept living and dining area, perfect for both relaxing and entertaining. The remodeled kitchen is a chef’s delight, featuring new, sleek cabinetry, attractive countertops, and all appliances included, making meal prep a breeze. The first floor boasts stylish
Updated 2-Bedroom, 2-Bath Ground Floor Condo with Patio in Gated East Lake Woodlands! This beautifully updated 2-bedroom, 2-bath condo is located in the desirable gated community of East Lake Woodlands. Featuring newer HVAC and a hot water heater (just 3 years old), this home offers modern comfort with luxury vinyl flooring throughout, including the screened lanai. The open-concept great room
Welcome to Aventine at Forest Lakes! Inside your new pet-friendly one, two, or three-bedroom apartment for rent, youll find everything you need for comfortable and convenient apartment living in Oldsmar, Florida. Each apartment comes with a fully-equipped kitchen, screened-in patios/balconies, plenty of closet space, air conditioning, and washer/dryer hookups for your convenience and comfort. At
Fully Furnished, Completely Renovated, Short Term Rental available 4/20/2026-11/20/2026. Enjoy peaceful mornings and serene evenings on your private patio overlooking the water in this immaculate 2 Bedroom / 2 Bathroom / 1 Car Garage First Floor Condo. This property is light and bright with a large great room and open kitchen. The recently renovated kitchen features white cabinets, stainless
East Lake Club Apartments is a place you can really call home. From the time you walk in for a tour until the day you move out we strive to make you feel comfortable and happy. Our gated community is located in the heart of Oldsmar, just minuets away from everything you need. Please feel free to give us a call, or stop by in person for more information on our property. We look forward to meeting
Back unit of a duplex, completely renovated, bathroom, kitchen, floors, paint and ceilings. Inside Laundry room W/D hook up. No dishwasher. Near cul-de-sac. quiet neighborhood. Large back yard view. Parking pad fits 2 cars. Great area to live in, close to everything: shopping, airport (20 min ride), restaurants and beaches. NO pets, NO drugs allowed. Clean background check + no eviction history,
Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,
Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2329.90. That covers your base rent, $2185.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet
Welcome to this impeccably maintained 3 bedroom, 2.5 bath residence in the highly sought-after Hayes Park Village in Oldsmar. Offering approximately 1,392 square feet of thoughtfully designed living space, this home showcases a beautifully renovated kitchen with contemporary finishes, ceramic flooring on the first floor, and carpet flooring on the second floor. The split-bedroom floor plan and
Welcome to 2024 Sheffield Ct, a charming single-story residence that perfectly balances classic style with modern convenience. This home offers 1,296 square feet of living space, featuring a thoughtful layout with 2 spacious bedrooms and 2 full bathrooms. Step inside to discover a bright and airy interior characterized by beautiful wood-style flooring and an abundance of natural light. The
Call to see this East Lake Woodlands Finest 2 Bedroom 2 Bath cute downstairs corner condo with almost everything new. Including most of the windows. Treat yourself to elegance in this remodeled Kitchen with LOTS of cupboard space and Quartz counters. New cabinets and lighting. Walk in to see the beautiful flooring throughout the condo. The large Master Bedroom has 3 closets and room for a King
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