Oldsmar Real Estate

Oldsmar Real Estate

Welcome to Oldsmar, a charming city located in Pinellas County, Florida. Nestled in the heart of the Sunshine State, Oldsmar offers a perfect blend of small-town charm and modern amenities.

Known for its picturesque landscapes and friendly community, Oldsmar is an ideal place to call home. The city is conveniently located near the stunning Gulf Coast beaches, making it a haven for outdoor enthusiasts and beach lovers. Whether you enjoy sunbathing, swimming, or engaging in water sports, you'll find plenty of opportunities to soak up the sun and enjoy the crystal-clear waters.

Oldsmar also boasts a thriving economy and a diverse range of employment opportunities. The city is home to several major corporations, including Nielsen, a global data and measurement company, which has its headquarters here. This provides residents with a variety of job prospects and contributes to the overall economic stability of the area.

In addition to its natural beauty and economic opportunities, Oldsmar offers a range of recreational activities for residents and visitors alike. The city is home to several parks, trails, and golf courses, providing ample opportunities for outdoor recreation. Additionally, Oldsmar hosts various community events throughout the year, including festivals, concerts, and farmers' markets, ensuring there's always something exciting happening in town.

With its prime location, strong community spirit, and abundant recreational opportunities, Oldsmar is a city that truly offers the best of both worlds. Whether you're looking to settle down, raise a family, or retire in a peaceful yet vibrant community, Oldsmar has something to offer everyone.

Newest Listings in Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8537217 MLS

Beautifully updated 2-bed, 2-bath home with brand-new luxury flooring in the highly sought-after Gull-Aire Village—complete with a FREE GOLF CART included with the sale. This property comes with the land, meaning absolutely NO LOT RENT, offering exceptional long-term value. Step inside to discover fresh designer paint, and tastefully renovated bathrooms that elevate the home’s modern, move-in-ready appeal. The screened-in front porch provides a peaceful spot to unwind and enjoy the Florida breeze. Gull-Aire Village is an active 55+ community known for its vibrant lifestyle, featuring a large, heated pool, spacious clubhouse, and a full calendar of social activities. The location is unbeatable—just moments from grocery stores, retail shopping, restaurants, entertainment, and everything Oldsmar has to enjoy. Move-in ready—enjoy your golf cart and start enjoying the Florida lifestyle. Please note: photos show the previous flooring; new laminate is being installed throughout.

116 Dolphin Drive S, Oldsmar

4 Beds ⋅ 3 Baths ⋅ TB8536934 MLS

Nestled within a gated neighborhood inside an exclusive gated golf course community, this exceptional single-family home offers the perfect blend of privacy, space, and luxury. Situated on an expansive lot of about 1/3 of an acre, the property enjoys a serene preserve backdrop, creating a peaceful setting with a spacious backyard and plenty of room to relax, entertain, or create your dream outdoor retreat. Thoughtfully designed with flexibility and comfort in mind, this spacious residence features four bedrooms, three full bathrooms, and a dedicated office, providing abundant space for a growing family, multiple home offices, hobby rooms, or welcoming guests with ease. High and Tray ceilings enhance the home's open, airy feel, while engineered wood flooring throughout the main living areas adds warmth, style, and timeless appeal. The heart of the home is the expansive family room and kitchen combination, designed for both everyday living and effortless entertaining. A cozy dining nook complements the generous snack bar, offering ample seating for family and friends. The kitchen is enhanced by taller cabinetry featuring distinctive glass inserts and decorative accent lighting with multiple color options, adding both elegance and personality. Anchoring the family room is a striking wood-burning fireplace featuring a custom mantel with an updated stacked-stone surround, creating a warm and inviting focal point for gatherings or quiet evenings at home. Step outside to your own private resort-style oasis. The expansive screened lanai, rescreened in 2023, surrounds a beautifully renovated pool and entertaining area. A Pebble Tec pool finish, sun shelf, dramatic stacked-stone waterfall, elegant travertine pool deck, and updated wet bar—all completed in 2023—create an exceptional outdoor living experience. The oversized three-car garage is equally impressive, featuring a professionally finished Spartacote Sparta-Chip floor for a clean, upscale appearance. Additional upgrades include Wi-Fi-enabled garage door openers and a hurricane-rated garage door, both installed in 2018, providing modern convenience and peace of mind. This meticulously maintained home has been extensively updated, allowing the next owner to move in with confidence. Significant improvements include a new roof (2019), hurricane-rated windows and doors (2022), remodeled hall and pool bathrooms (2017), replacement chimney cap (2024), hot water heater (2024), water softener (2025), and numerous thoughtful enhancements throughout. These investments not only enhance the home's beauty but also provide exceptional value, efficiency, and long-term peace of mind. Located within one of the area's premier gated golf course communities, this home offers the opportunity to enjoy an exceptional lifestyle, with golf and social memberships available for purchase separately. Combining generous living spaces, extensive upgrades, luxurious indoor and outdoor amenities, and an outstanding homesite, this remarkable residence is a rare opportunity to experience the very best of Florida living.

4987 Cross Pointe Drive, Oldsmar

Presenting a rare opportunity to acquire a well-positioned property in the heart of Oldsmar. This offering combines excellent visibility with approximately 300ft frontage on SR 580 and is easily accessible with the signalized corner and permitted DOT ingress and egress. The location benefits from continued development along retail corridors and continually growing residential communities in the area. The property features multiple zonings allowing for a variety of potential uses spanning office, retail, restaurant and residential. This property provides the flexibility to meet a range of investment strategies along with the potential for seller financing making it more accessible for a wide range of investors.

205 Chestnut Street, Oldsmar

3 Beds ⋅ 2 Baths ⋅ TB8536647 MLS

Discover your own slice of Florida paradise with this charming three-bedroom, two-bathroom home, perfectly situated in the highly sought-after community of The Fountains at Cypress Lakes in Oldsmar. Boasting a private, sparkling in-ground pool, this beautiful home is conveniently in walking distance of the local elementary school, and easy access to local shops, restaurants, local airports and beautiful Florida beaches. This community has so much to do! Enjoy the many parks, nearby ice-skating arena. pickleball courts, childrens spray park, Oldsmar Sports Complex and local movie theater. The sports complex is home to Oldsmar BMX and Oldsmar Little League. Step inside to a thoughtfully designed floor plan that maximizes comfort and functionality. Enjoy beautiful newly installed Luxury Vinyl Plank through out the home with a transferable warranty! The spacious living areas provide ample room for both daily living and hosting guests. The well-appointed kitchen is perfect for preparing meals, while the inviting bedrooms offer a peaceful retreat at the end of the day. New cellular blinds just installed. The primary suite includes 2 walk-in closets and an en-suite bathroom for added convenience and privacy. The windows in the home have solar film which reduce heat and UV rays, increase privacy and improve energy efficiency. There is a newly installed hot water heater with a transferable warranty. The HVAC is equipped with a HEPA filter, UV light and Guardian device that kills bacteria, mold and viruses in the duct work. The attic has extra insulation which also helps improve the home's energy efficiency. The sparkling pool has a Stonescape surface for enhanced durability and a comfortable non-slip surface, and pavers for the pool deck complete the sophisticated look complementing the overall design of the backyard. The two-car garage is equipped with a back-up battery for the door opener for added peace of mind. The true highlight of this home is the private backyard oasis. Imagine spending sunny Florida afternoons lounging by your own pool or relaxing on the beautiful lanai with your morning coffee, enjoying the tranquility and greenery of your backyard. With the home backing up to conservation, you'll often be treated to the delightful sight of deer, egrets, ibis, sandhill cranes, hawks and songbirds in your backyard, adding a unique touch of wildlife to your everyday life. The Fountains at Cypress Lakes is a well-maintained community known for its pride of ownership and manicured landscapes. Residents enjoy a low annual HOA fee and no CDD fees, making it an attractive option for homeowners. Don't miss out! Schedule your showing today!

333 Tavernier Drive, Oldsmar

3 Beds ⋅ 2 Baths ⋅ TB8528046 MLS

Welcome home to this charming 3-bedroom, 2-bathroom home with a 2-car garage, ideally located in the desirable Bayside Meadows community with NO HOA or CDD fees. From the moment you step inside, you'll appreciate the open layout featuring a spacious living room that flows seamlessly into the dining area, creating the perfect space for both everyday living and entertaining. Just beyond the dining room is the well-appointed kitchen, complete with beautiful granite countertops, ample cabinetry, and a full appliance package, making meal preparation both convenient and enjoyable. Sliding glass doors lead to the backyard, offering plenty of space for outdoor entertaining, gardening, pets, or simply relaxing. The yard is partially fenced, providing added privacy while still allowing room to personalize the outdoor space. The two secondary bedrooms are generously sized and share a full bathroom with a tub/shower combination. The spacious primary suite serves as a peaceful retreat and features a private en-suite bathroom. Living in Oldsmar means enjoying an exceptional Florida lifestyle with nearby attractions including Tampa Bay Downs, the Oldsmar Ice Sports Complex, Sheffield Park, the Oldsmar BMX Supercross Track, Mobbly Bayou Beach Park, and the scenic Mobbly Bayou Wilderness Preserve. You'll also appreciate the home's convenient location near shopping, dining, entertainment, medical facilities, and major roadways, making commuting to Tampa, Clearwater, and the surrounding areas a breeze. Don't miss your opportunity to make this wonderful home your own. Schedule your private showing today!

1916 Hudson Court, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8536581 MLS ⋅ 2 BLDG.

Welcome to this beautiful 2-bedroom, 2-bathroom ground-floor condo in the highly sought-after East Lake Woodlands community. Built in 1979 with durable masonry construction and a slab foundation, this charming residence offers the perfect blend of comfort, character, and convenience. Enjoy peaceful pond views from the rear of the home while being surrounded by the outstanding amenities this master-planned community has to offer, including golf courses, nature trails, swimming pools, and a clubhouse. Ideally located between Hillsborough and Pinellas Counties, you'll have easy access to an incredible selection of shopping, dining, entertainment, and Gulf Coast attractions. Inside, timeless elegance shines through with beautiful oak flooring, a cozy wood-burning fireplace, and a convenient pass-through from the kitchen to the living area, creating an open and inviting space for everyday living or entertaining. The in-unit utility closet includes a washer and dryer for added convenience, while the generous closet space provides exceptional storage rarely found in condominium living. A covered parking space located directly in front of the unit makes unloading groceries and staying dry during Florida's afternoon showers a breeze. Whether you're looking for a year-round residence, a seasonal retreat, or an investment opportunity, this exceptional condo offers the best of maintenance-free living in one of the area's most desirable gated communities. Come experience the beauty and lifestyle of East Lake Woodlands and make 205 Martha Lane your new home!

205 Martha Lane Unit 205, Oldsmar

3 Beds ⋅ 1 Baths ⋅ TB8536069 MLS

CHARMING 3 bed, 1 bath impeccable home in downtown Oldsmar area. NEW interior doors, NEW stove, NEW baseboards, NEW bathroom vanity, lighting, mirror,, NEW remote control ceiling fans with lights, NEW carriage lights (front and back) NEW GFCI outlets, NEW paint interior, exterior, NEW paint garage, patio, NEWER windows and slider with integral blinds (2023, 2026), HWH 2025, DISHWASHER 2023, MICROWAVE 2022, ROOF 2022. Use your imagination with the oversized patio for a total outside living experience; large fenced yard. This home is located a short distance from Mobbly Bayou waterfront park, RE Olds park with fishing pier, event and picnic areas, playgrounds, volleyball, and Bicentennial Park with tennis and pickleboard courts, shaded walking paths, and home to Adventure Zip Line Tours. Shopping, restaurants, theater, athletic facilities, museum, school and library all only minutes away. WORLD CLASS BEACHES and TAMPA INTERNATIONAL AIRPORT are both nearby. Zoned for Oldsmar Elementary School (A rated) and NOW a K through 8 school. This home is HIGH AND DRY!

650 Timber Bay Circle W, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8535936 MLS

163 Dolphin Drive, Oldsmar, FL Welcome to one of the standout homes in Gull-Aire Village, Oldsmar's highly sought-after 55+ community. Situated on a desirable corner lot, this beautifully renovated 2-bedroom, 2-bathroom home combines modern style with comfortable, low-maintenance living. From the moment you arrive, you'll appreciate the spacious two-car carport, attractive curb appeal, and thoughtful updates throughout. Inside, the open-concept floor plan creates an inviting space where the living room, family room, dining area, and beautifully remodeled kitchen with quartz counters and stainless steel appliances flow seamlessly together—ideal for everyday living or entertaining family and friends. The kitchen serves as the heart of the home with its contemporary finishes, generous workspace, and open sightlines to the main living areas and plenty of bright lighting. Both bedrooms are well-proportioned, and the updated bathrooms reflect the same quality craftsmanship found throughout the home. Outdoor living is just as impressive. The covered rear patio has been thoughtfully designed and is ready for your dream outdoor kitchen, creating the perfect setting for relaxing, dining, or hosting gatherings year-round. An attached storage shed provides plenty of room for tools, hobbies, seasonal décor, or golf cart accessories. Life in Gull-Aire Village offers more than just a beautiful home—it offers an exceptional lifestyle. Residents enjoy a vibrant calendar of social events, clubs, activities, and community gatherings throughout the year, making it easy to meet neighbors and stay engaged. The community's golf cart-friendly streets make it convenient and enjoyable to travel to the clubhouse, amenities, and visit with friends. Conveniently located near shopping, restaurants, medical facilities, parks, beautiful Gulf Coast beaches, Tampa International Airport, and the charming downtowns of Oldsmar, Safety Harbor, and Dunedin, you'll have easy access to everything the Tampa Bay area has to offer. If you've been searching for a move-in ready home where every detail has already been completed, 163 Dolphin Drive is an exceptional opportunity. Beautifully updated, thoughtfully designed, and located in one of Oldsmar's most welcoming communities, this home is truly one of Gull-Aire Village's finest.

163 Dolphin Drive E, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8534748 MLS

Investor special with exceptional upside! This concrete block 2-bedroom, 2-bath, 2-car garage home is priced to sell and offers outstanding renovation potential. Situated on a nicely sized lot with beautiful lake views and no rear neighbors, the fully fenced backyard has plenty of room for a pool. The home has an updated electrical panel. The HVAC system was updated in 2019. The roof was last replaced in 2009. The office provides approximately 270 additional square feet beyond the heated living area, offering flexible space for a home office, hobby room, or future expansion. (The second bathroom is located in the garage.) Enjoy a great central location just a short walk to Sheffield Park and Harbor Palms Nature Park, featuring walking trails, a boardwalk, fishing pier, and kayak launch. No HOA and convenient access to Tampa, St. Petersburg, Gulf beaches, shopping, dining, and Tampa International Airport. Cash offers only. Property is being sold As Is with no repairs. Can be purchased individually or as part of a package with MLS #TB8366557 (613 Chestnut St.) and MLS #TB8366564 (204 Shore Dr. W.), all offered by the same seller.

704 Lemonwood Drive, Oldsmar

5 Beds ⋅ 4 Baths ⋅ TB8534625 MLS

Exceptional builder or investor opportunity in a prime Oldsmar location! Situated on an oversized 11,347 sq. ft. lot directly across from scenic R.E. Olds Park, this property offers partial water views of Tampa Bay, park views, and outstanding redevelopment or renovation potential. The existing structure includes a 3-bedroom, 2-bath upper level plus two 1-bedroom, 1-bath lower-level units, offering multiple possibilities for redevelopment or renovation (buyer to verify permitted use). Additional features include a 2-car carport and a concrete block storage building. Enjoy a golf cart-friendly community with walking trails, fishing pier, playgrounds, picnic shelters, and year-round events just across the street. Cash offers only. Property is being sold As Is with no repairs. Can be purchased individually or as part of a package with MLS #TB8366525 (704 Lemonwood Dr.) and MLS #TB8366564 (204 Shore Dr. W.), all offered by the same seller. Conveniently located with easy access to Tampa, St. Petersburg, Tampa International Airport, and Gulf beaches.

613 Chestnut Street, Oldsmar

3 Beds ⋅ 2 Baths ⋅ TB8534439 MLS

Investor special with exceptional upside! This 3-bedroom, 2-bath, 1-car garage home sits on a spacious quarter-acre corner lot directly across from scenic R.E. Olds Park, offering water views, walking trails, playgrounds, a fishing pier, picnic shelters, volleyball courts, seasonal events, and a dog park. The home features a split-bedroom floor plan with a primary suite that includes a walk-in closet, en-suite bath with a step-in shower, and sliding glass doors leading to a patio. The guest bath offers a tub/shower combination. The roof was replaced in 2016. Double-pane sliding glass doors open to two patios overlooking the park. No HOA or deed restrictions—bring your boat, RV, or golf cart! Great central location with convenient access to Tampa and St. Petersburg. Can be purchased individually or as part of a package with MLS #TB8366557 (613 Chestnut St.) and MLS #TB8366525 (704 Lemonwood Dr.), with all three Oldsmar properties offered by the same seller.

204 Shore Drive W, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8535233 MLS

This spacious and well maintained 2-bedroom, 2-bath end unit Villa offers a comfortable floor plan and easy, worry-free living right in the heart of Oldsmar. With nearly 1,300 square feet and vaulted ceilings, the home features all tile flooring throughout, a large kitchen with plenty of cabinetry and a breakfast bar, plus an open family/dining area. The living room includes a cozy fireplace, creating a warm focal point for the space. Sliders lead to an enclosed porch, perfect for relaxing or enjoying morning coffee. An interior laundry closet adds everyday convenience. Major system upgrades provide excellent long-term value and peace of mind: • New roof (2021) • New HVAC (2024) • New water heater (2024) • New electrical panel (2024) • Impact windows (2016) • Sliding glass door (2018). A rare and highly desirable bonus is the two assigned covered parking spaces steps from your front door—a standout feature in this community and a true benefit for owners. Community amenities include a sparkling pool, and you’re just down the street from Sheffield Park, featuring tennis and basketball courts, a playground, dog park, fishing, disc golf, exercise stations, walking paths, and more. With low HOA fees of $110/month, including lawn maintenance, you’ll have plenty of time to enjoy the pool and Oldsmar’s interconnected parks. You’re also steps from Harbor Palms Nature Park and Preserve and the Oldsmar Trail, an 11-mile trail popular with bicyclists and joggers —perfect for nature walks, wildlife viewing, and beautiful sunsets. Nearby conveniences include athletic fields, shopping, dining, and world class beaches. This Villa is a well-cared for home with major updates already completed, offering comfort, convenience, and the best of Florida living.

2060 Sheffield Court, Oldsmar

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