Oldsmar Homes for Sale

Oldsmar Homes for Sale

Welcome to Oldsmar, Florida – a delightful gem nestled in the heart of Pinellas County, where the charm of small-town living meets the vibrancy of coastal life. With its picturesque parks, scenic waterfront views, and a warm community spirit, Oldsmar offers an idyllic setting for families, retirees, and everyone in between.

Just a stone's throw away from the stunning Gulf Coast beaches, Oldsmar boasts a strategic location that provides easy access to the bustling cities of Tampa and St. Petersburg. Residents enjoy a perfect blend of tranquility and convenience, with a variety of shopping, dining, and recreational options right at their fingertips. The city is also home to several beautiful parks, including the expansive Oldsmar Sports Complex and the serene Mobbly Bayou Wilderness Preserve, perfect for outdoor enthusiasts and families alike.

If you're looking to make Oldsmar your home, you’ll be pleased to know that there are a variety of homes for sale in this charming city. From cozy single-family residences to modern townhouses, the real estate options cater to diverse tastes and budgets. Many properties feature lush landscaping, spacious yards, and proximity to top-rated schools, making it an ideal place to raise a family.

Whether you’re searching for a peaceful retreat or an active lifestyle, Oldsmar has something for everyone. Explore the homes for sale today and discover the opportunity to become part of this welcoming community. Your dream home awaits in Oldsmar, where every day feels like a vacation!

Newest Oldsmar Homes for Sale

4 Beds ⋅ 3 Baths ⋅ Cross Pointe SubDv. ⋅ 34677 Zip Code

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

3 Beds ⋅ 2 Baths ⋅ Fountains At Cypress Lakes Ii-A The SubDv. ⋅ 34677 Zip Code

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 ⋅ Bayside Meadows-Phase I SubDv. ⋅ 34677 Zip Code

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

3 Beds ⋅ 1 Baths ⋅ Shoreview Ph 2 SubDv. ⋅ 34677 Zip Code

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 ⋅ Harbor Palms-Unit Five SubDv. ⋅ 34677 Zip Code

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 ⋅ Oldsmar Revised Map SubDv. ⋅ 34677 Zip Code

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 ⋅ Oldsmar Revised Map SubDv. ⋅ 34677 Zip Code

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 ⋅ Sheffield Village At Bayside Meadows SubDv. ⋅ 34677 Zip Code

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

3 Beds ⋅ 2 Baths ⋅ Sheffield Village Ph Ii At Bayside Meadows SubDv. ⋅ 34677 Zip Code

--SERIOUS SELLER-WILLING TO NEGOTIATE-- Check out this BEAUTIFUL 3-bedroom, 2-bath BLOCK home WITH GARAGE. located on a quiet cul-de-sac in the heart of Oldsmar. BEAUTIFUL HIGH GLOSS TILE FLOORING THROUGHOUT Featuring spacious living areas with vaulted ceilings, a primary bedroom with an ensuite, and a split bedroom layout for added privacy and a rear screened porch perfect for relaxing or entertaining. The home has been thoughtfully upgraded with a new electrical panel (2018), roof (2020), air conditioning system (2021), gutters (2022), garage door (2022), water heater (2022), and water softener tank (2024) Exterior Water Line (2025). along with fresh exterior paint. Situated just steps from Sheffield Park, residents enjoy access to hiking and running trails, tennis and basketball courts, a playground, and a covered pavilion for events. Conveniently close to shopping centers, restaurants, downtown Tampa, the international airport, Clearwater beaches, and St. Pete, this neighborhood offers a peaceful environment with NO HOA fees. This turnkey home combines modern comfort with an unbeatable location—great curb appeal, stop by and take a look you wont be disappointed! MOTIVATED SELLER! SUBMIT YOUR OFFER TODAY!

1909 Castle Bay Court, Oldsmar

4 Beds ⋅ 3 Baths ⋅ Greenhaven Unit Two SubDv. ⋅ 34677 Zip Code

Homes like this rarely become available in the highly sought-after gated community of East Lake Woods. Completely remodeled and situated on over a quarter acre overlooking a tranquil pond, this exceptional residence offers the perfect blend of luxury, comfort, and functionality. From the moment you arrive, you'll appreciate the expansive driveway, oversized three car garage, and impressive curb appeal. As you approach the grand double-door entrance, soaring 12 foot ceilings immediately set the tone for what awaits inside. Step through the front doors and your eyes are instantly drawn to the breathtaking views of the sparkling pool and peaceful pond beyond. The home has been freshly painted inside and out and showcases new luxury waterproof vinyl plank flooring throughout, creating a seamless, modern aesthetic. Designed with both everyday living and entertaining in mind, the home features a desirable three way split floor plan, offering privacy for family members and guests alike. The spacious primary suite is a true retreat, complete with high ceilings, plantation shutters, and a spa-inspired ensuite bathroom. Relax in the freestanding soaking tub or unwind in the oversized walk-in shower featuring a rainfall showerhead and body jets. The luxurious bath also includes dual vanities, a dedicated makeup station, and an illuminated LED mirror. As you continue into the heart of the home, you'll discover a stunning open-concept kitchen and family room designed to impress. The fully remodeled kitchen features brand-new solid wood soft-close cabinetry, Taj Mahal quartz countertops, a cooktop with pot filler, new stainless steel appliances, and exceptional workspace for the home chef. Adjacent to the kitchen is a bright breakfast nook overlooking the pool, as well as a separate butler's pantry perfect for a coffee bar, beverage station, or additional storage. Entertaining is effortless thanks to the beautifully redesigned wet bar, featuring rich dark cabinetry, ambient lighting, a sink, and a built-in wine refrigerator. Just beyond, the expansive family room provides ample space for gatherings of any size. A beautifully renovated guest bathroom off the kitchen features designer tile, a modern vanity, and an LED mirror. Toward the rear of the home, you'll find two additional spacious bedrooms and another fully remodeled bathroom with dual sinks, LED mirrors, and convenient access to the pool. Step outside to your own private backyard oasis. The oversized screened lanai surrounds the sparkling pool and offers the perfect setting for year-round Florida living. The outdoor kitchen is equally impressive, showcasing stunning Brown Fantasy granite countertops, a new built-in grill, and a beverage refrigerator. The finishing touch? Your very own private putting green. Whether you're practicing your short game, entertaining guests, or simply enjoying the peaceful pond views, this backyard is designed to be enjoyed. Every detail of this remarkable home has been thoughtfully updated, creating a truly move-in-ready opportunity in one of the area's most desirable gated communities. Additionally residents have the opportunity to join the on-site Ardea Country Club, optional memberships provide access to championship golf, tennis, pickleball, a resort style lap pool, state of the art fitness center and dining. Minutes from top rated schools, Tampa International and St. Pete-Clearwater airports, award-winning Gulf beaches, professional sports team and more!

35 Greenhaven Trail, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Oldsmar Country Club Estates Sec 3 SubDv. ⋅ 34677 Zip Code

Florida living at it's best. This fully renovated beautiful solid block home is located in the very desirable Oldsmar Country Club Estates neighborhood and is across the street from the bay and just down the street from three waterfront parks, Veterans Memorial Park, R.E. Olds Park and from Mobbly Bayou Beach Park. This charming house boasts a split bedroom open floor plan. It has a giant sun room/all day room connected to the back of the house with plenty of windows surrounding it. The owner is selling personal items to get ready for the sale of the home and they show as clutter in the pictures, so I might be posting new pictures soon. These pictures don't do this wonderful home justice. Wait till you see this huge kitchen with it's quartz countertops, stainless steel appliances and very spacious wood cabinets. There are fruit trees in the back yard which include mango trees and sweet sop trees. The garage is air conditioned and heated. This home is conveniently located only 15-20 minutes from Tampa International Airport and only minutes to downtown Tampa and to some of the best beaches in the US, great restaurants, shopping, theaters and hotels. There are also tennis courts, a zip line, hiking trails, kayaking and paddle boarding, the neighborhood boat ramp, an organic garden, the public library and lots of shops all walking distance from the house.

331 Shore Drive E, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Parcel B - The Pinnacle SubDv. ⋅ 34677 Zip Code

RARELY AVAILABLE VILLA OPPORTUNITY IN PRIVATE PINNACLE COMMUNITY OF EAST LAKE WOODLANDS. "THIS IS A MAINTENANCE FREE COMMUNITY." WALK THRU DOUBLE GLASS ENTRY DOORS TO FOYER THAT OPENS TO LIVING ROOM. LIGHT AND BRIGHT EXPANDED FAMILY ROOM AND KITCHEN OFFERS QUIET VIEWS OF CONSERVATION AND GOLF COURSE AREA. NEWLY EXPANDED LANAI WITH PARORAMIC BIRDCAGE SCREENING. KITCHEN OVER LOOKS FAMILY ROOM HAS CENTER ISLAND AND WOOD CABINETRY, BUILT-IN PANTRY, GRANITE COUNTER TOPS AND ALL STAINLESS-STEEL APPLIANCES. SEPARATE DINING ROOM WITH EASY ACCESS FROM THE KITCHEN. MASTER BEDROOM WITH TWO WALK-IN CLOSETS AND MASTER BATH WITH FREE STAND TUB, SEPARATE STALL SHOWER, PRIVATE TOILET CLOSET, DOUBLE SINK VANTY WITH GRANITE COUNTER AND CUSTOM TILE. OFFICE WITH DOUBLE DOOR ENTRY CAN ALSO BE USED AS THIRD BEDROOM WITH CLOSET. SECLUDED SECOND BEDROOM IS PERFECT FOR GUESTS WITH ADJOINING BATH. INSIDE LAUNDRY ROOM WITH UTILITY SINK AND EXTRA STORAGE. GARAGE HAS EXTRA STORAGE AND SPACE FOR TWO CARS. THIS SEPTACULAR HOME LOCATED ON A PRIVATE CUL-DE-SAC. FOR SOCIAL ENJOYMENT YOU CAN RELAX IN THE COMMUNITY POOL. CLUBHOUSE MEMBERSHIP IS ALSO AVAILABLE FOR TENNIS AND GOLF. CLOSE TO BEACHES, SHOPPING, HOSPITALS, AND AIRPORTS. THIS IS WAITING FOR YOU!

5250 Pinehurst Court, Oldsmar

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