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 natural beauty, thriving community, and convenient amenities.

Known for its picturesque landscapes, Oldsmar boasts a prime location near the stunning Gulf of Mexico, allowing residents to enjoy breathtaking sunsets and endless opportunities for outdoor recreation. The city is also surrounded by several pristine parks, offering hiking trails, picnic spots, and playgrounds for families to enjoy.

Oldsmar is proud to offer a strong sense of community, with a variety of events and activities throughout the year. From local festivals and farmers markets to art exhibitions and live performances, there is always something happening in this vibrant city. Residents can also take advantage of the city's recreational facilities, including sports fields, tennis courts, and a state-of-the-art fitness center.

In terms of amenities, Oldsmar has everything you need within easy reach. The city is home to a range of shopping centers, restaurants, and entertainment options, ensuring that residents have access to all their daily needs. Additionally, Oldsmar is conveniently located near major highways, making it easy to explore the surrounding areas and enjoy all that Florida has to offer.

Whether you're looking for a peaceful place to retire or a family-friendly community to settle down in, Oldsmar has it all. With its beautiful surroundings, strong sense of community, and convenient amenities, it's no wonder why so many people choose to call Oldsmar home.

Newest Listings in Oldsmar

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

Welcome to 4953 Pointe Cir, a stunning 4-bedroom, 3-bathroom single-family home located in the Cross Pointe subdivision of East Lake Woodlands, one of the most sought-after golf course communities in the Tampa Bay area. This 2,513 sq. ft. home features the perfect layout, open concept, lush landscaping, a heated pool and spa with a screened enclosure, and a 3-car garage. As you step inside, you'll be greeted by an inviting floor plan perfect for both entertaining and everyday living. The primary bedroom is a true sanctuary, boasting an en suite bathroom with dual closets, providing ample storage space. The additional three bedrooms are spacious and versatile, making them ideal for guests, family, or a home office. Enjoy resort-style living in your own backyard with a heated pool and spa, all enclosed within a screened lanai for year-round enjoyment. The home’s lush landscaping provides privacy and enhances the outdoor ambiance. Located in the exclusive gated community of Cross Pointe, residents enjoy the comfort, safety, and sense of community that this neighborhood offers. For those seeking an active lifestyle, the Ardea Country Club—within East Lake Woodlands—offers optional membership that includes access to two championship 18-hole golf courses, tennis and pickleball courts, a fitness center, multiple pools, and a clubhouse with restaurants. This home’s prime Oldsmar location makes commuting to Tampa, St. Pete, and the surrounding areas a breeze. It’s also conveniently close to a variety of shops, restaurants, and entertainment, and zoned for top-rated Pinellas County schools. Don’t miss the chance to live in one of the most exclusive communities in Tampa Bay! Schedule your private showing today and experience the best of East Lake Woodlands living.

4953 Pointe Circle, 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 an exceptional floor plan, perfect for the active Florida lifestyle. The nearly 1,300 square-foot home features a large kitchen with ample cabinetry and a breakfast bar, seamlessly flowing into the family and dining areas with wood floors and sliders leading to a screened lanai. The Villa includes 6-panel interior doors, tile baths, and an interior laundry closet. Located in the heart of Oldsmar, this rare opportunity places you within walking distance to the Oldsmar Trail, connecting to Sheffield Park, Safety Harbor, and Mobbly Bay, offering beautiful sunsets, nature walks, and wildlife. The community includes ground maintenance and a pristine swimming pool for just $110/month HOA. You'll also enjoy nearby amenities such as tennis courts, athletic fields, playgrounds, shopping, dining, and world-class beaches. This Villa is truly a gem, offering both convenience and the best of Florida living.

2002 Sheffield Court, Oldsmar

3 Beds ⋅ 1 Baths ⋅ Oldsmar Rev Map SubDv. ⋅ 34677 Zip Code

Discover this beautifully updated 3-bedroom, 1-bathroom home, perfectly situated on a spacious 7,453 sq. ft. lot. Boasting 1,022 sq. ft. of thoughtfully designed living space, this single-story bungalow features an open, light-filled floor plan. The fully fenced backyard borders a peaceful nature reserve, ensuring no future development behind the home. Located just two blocks from R.E. Olds Park with its fishing pier and vibrant city events, and within walking distance to Oldsmar Elementary. No HOA, no CDD—enjoy complete freedom in this prime location. Schedule your private tour today!

306 Chestnut Street, Oldsmar

3 Beds ⋅ 2.5 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code

MOVE-IN READY!!! Bayside Terrace Townhome built in 2018. Well-Maintained, in excellent condition. First floor primary bedroom with ensuite bathroom and laundry. Open, Eat-In Kitchen with quartz counters. Spacious first floor living room with adjacent half-bath overlooking a screened, brick-paved lanai. The second floor features an oversized multi-purpose family room, two bedrooms with walk-in closets, and a shared bathroom with dual sinks and tub-shower combo. This community is impeccably located near downtown Oldsmar and just 6 miles from Safety Harbor. Retail, restaurants, and parks abound. Situated on beautiful Old Hillsborough Bay, Bayside Terrace features a resort-style infinity pool, upscale clubhouse with fitness center, a kayak launch, a fire pit, and a fishing dock. Bring your kayaks and SUP's and store them in the two-car garage with the existing elevated storage straps. This is a unique opportunity to own in a WATERFRONT community.

1107 Mango Court, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Country Club Add To Oldsmar Rev SubDv. ⋅ 34677 Zip Code

Your Florida home awaits!!! This Gorgeous, totally remodeled 3/3/1 is a perfect home is historic Oldsmar. Bring your golf cart to this active FL community. This block home sits high on an elevated lot overlooking the sparkling bay waters from its front door. The just over quarter acre pie-shaped lot leaves you plenty of room for activities. No HOA/CDD or deed restrictions. Walking through the front door you are greeted by an open living room/ kitchen floor plan. Newly repainted interior with matching oil rubbed bronze fixtures/hardware. Walking into the kitchen you are welcomed by newly done ship lapped walls, quartz counter tops and gleaming stainless steel appliances. All rooms are cooled individually with its own mini split unit giving excellent energy efficiency. All three bathrooms have been remodeled with contemporary black slate hex tiles and brand new vanities. The master bedroom/bathroom is fit for a king. Brand new energy efficient rear slider. All windows in this home have been updated for impact resistance and have Bay window shutters. Walking out back, you are perched upon a handsome plasti-wood deck that extends the entire length of the home. Great for cook-outs! Out back is a paved seating area with a fire pit for the Florida winter nights. Even the garage was remodeled with an enclosed laundry room that is also air conditioned. Camera system conveys with the home as well as all appliances. Convenient to Tampa and St Pete and minutes from world-class beaches. East Lake High School zoned

100 Kilsythe Street, Oldsmar

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code

Live your best life in the highly sought-after, gated community of Eastlake Woodlands! This beautifully updated 1st-floor condo offers breathtaking lakefront views and a spacious open layout. As you step inside, you'll notice the stylish plantation shutters, gorgeous transom windows in the Florida room, along with the other Hurricane impact windows to ensure safety and efficiency. Kitchen is completely updated with recessed lighting, stone countertops, and wood cabinets that allow ample storage. Updated floors flow throughout the main living area creating a cohesive feel. The master suite is a true retreat, featuring three closets for ample storage and an ensuite bathroom. Wake up to peaceful lake views or finish your day relaxing in the screened-in Florida room, where you'll also find a convenient laundry closet with a washer and dryer. Other important features: BRAND new AC, and updated electrical panel. Eastlake Woodlands is an active, vibrant community with two 18 hole golf courses and Country club, brand new clubhouse, fitness center, many pools to choose from and lots of walking trails for you and your pets. With quick access to two international airports, major sports arenas, and some of the world’s best beaches, this location has it all! Plus, enjoy the convenience of nearby shopping and dining options.

167 Lakeview Way Unit 167, Oldsmar

4 Beds ⋅ 2.5 Baths ⋅ Eastlake Oaks Ph 1 SubDv. ⋅ 34677 Zip Code

Welcome to this **stunning 4-bedroom, 2.5-bathroom** home, located in one of **Oldsmar’s most desirable neighborhoods**. Thoughtfully designed, this two-story home offers over **2200 square feet** of beautifully functional living space, blending style with modern convenience. This home is located just minutes from **top-rated schools**, **shopping**, **dining**, and **Tampa International Airport**. With easy access to **Pinellas** and **Pasco counties**, you’re never far from beaches, parks, and cultural activities. Upon entering, you’re greeted by an open, light-filled floor plan that’s perfect for easy indoor-outdoor living. To your left is a cozy sitting room, ideal for relaxing or welcoming guests. The heart of the home is the gourmet kitchen and how it seamlessly flows into the spacious living area. It features **stone countertops**, **real wood cabinetry**, and premium stainless steel appliances. The living area is perfect for entertaining or everyday family life. Large **sliding glass doors** lead to a private **in-ground pool** within a **screened lanai**, creating the ideal space for relaxing and entertaining. Upstairs, a versatile **loft space** offers flexibility for a second living area, home office, or playroom. The **master suite** is a peaceful retreat with large windows and a **luxurious en-suite bathroom** complete with a **walk-in shower**, **soaking tub**, and **dual vanities**. It’s your own personal sanctuary. Three additional upstairs bedrooms offer generous space and ample storage and the full bathroom off the hallway adds convenience for all. Beyond the pool, a **fully fenced yard** provides privacy and room for pets or extra entertaining. The **three-car garage** offers ample space for vehicles, storage, or a workshop. Plus, **solar panels** help minimize monthly expenses, making the home energy-efficient and cost-effective. Offering the best in **Florida luxury living**, this home combines elegant design, outdoor comfort, and sustainable living. Schedule a private showing today and make this exceptional property yours! https://my.matterport.com/show/?m=4bLsqEmEhSy&brand=0&mls=1&

1600 Gray Bark Drive, Oldsmar

3 Beds ⋅ 2.5 Baths ⋅ Hayes Park Village SubDv. ⋅ 34677 Zip Code

This Meticulously Kept 3 bedroom, 2.5 bath Detached Townhouse offers a Unique Blend of Modern Southern Elegance along with Modern Convenience. Located in the Heart of Oldsmar Florida, (and Much Like the Previous Sales Agent Proclaimed) … It Captures the Similarity and, is Reminiscent of Old Southern Cities like Charleston. Located in the Boutique Community of Hayes Park Village, this is a True Gem. Offering a perfect Combination of Historic Allure, Contemporary Comfort, and Timeless Architectural Charm.! . Now… Upon arrival, you’ll step onto the Beauty of Well-Maintained Grounds, and Immediately be Greeted by the Tranquility of this Unique Boutique Community. With the Amenities for Relaxing Around the Firepit within a Sereen Surrounding of Lavish Greenery and Amazingly Enchanting Ambiance of Well-Kept Surroundings. You’ll find Yourself in an Atmosphere of Memorable Times and Friendly Neighbors. With a Freshly Painted Exterior to add to this Beautiful Townhomes' Interior, the Inside of this Townhouse is a Perfect Blend of Sophistication and Functionality. The 3 Bedrooms allow Ample Space for Relaxation and Room for Comfort, while the Bathrooms are Designed with Modern Details in Mind. With Open Concept Living Areas, and Perfect Lighting it Creates a Welcoming Atmosphere for Both Daily Living and Entertaining Family and Guests Alike. This Townhome Guarantees a Comfortable and Stylish Living Experience with a Connection to the Rich History of Southern Architecture. Take Advantage of Your Opportunity to Own this Detached Townhome, among the Few, in Charming Oldsmar. And Make New Beginnings Come True.!

320 Vista Cruiser Lane, Oldsmar

Tampashores Hotel Plaza Sec SubDv. ⋅ 34677 Zip Code

I present you this residential land with a privileged location since is a corner lot. It offers you everything you need for both future investment or to develop the house of your dreams. Create a unique home tailored to your lifestyle, making the most of the potential of the lot in a safe environment, without HOA or CDD restrictions. Don't miss this unique opportunity.

113 Shore Drive Place, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code

This meticulously maintained, partially furnished 2 bedroom/2 bathroom home is move-in ready! The home features cathedral ceilings, an updated kitchen complete with stainless steel appliances, pantry closet, cozy breakfast nook, a bright and sunny Florida room that could double as a den due to the upgraded windows and adds 144 sf of air conditioned space for a total of 1,172 sf, updated bathrooms complete with sky lights and in-house laundry closet with front loading washer/dryer. The furniture included is as follows: Gray leather sofa and loveseat with reclining features, dinette set with 4 chairs as shown in the dining area, table with 2 chairs as shown in the breakfast nook in the kitchen, bar stools at the peninsula, bed/mattress, wicker dresser, mirror and chest as shown in the guest bathroom and vinyl wicker table with 4 chairs and umbrella in the screened patio. Upgrades include Trane a/c system (2021), double-pane windows throughout (2016), exterior door replacement (2015). Other upgrades throughout the entire home include stylish laminate plank flooring, interior doors and lighting fixtures and fans. Other features include screened patio, spacious driveway for ample parking that extends to an open air side patio, (all of which have premium pavers installed) and 2 storage sheds 10’ x 10’ and 5’ x 7’. Gull-Aire Village is a 55+ golf cart friendly community that offers an enormous clubhouse, a large heated pool and spa, library, enclosed shuffleboard court, bocce ball court along with a wide variety of planned activities and social events. You own the land that this beautiful home is situated on. On top of all of the above, the HOA monthly fee is only $50.00!! One dog, cat or bird is permitted. Gull-Aire Village is conveniently located less than 1 mile from Woodlands Square where you will find Bealls, Marshall’s, Ulta, PetSmart, Dollar Tree, AMC Theater, Craft Street Kitchen, Shaker & Peel, Eve’s Family Restaurant along with other service oriented businesses. Mease Countryside Hospital and Medical Arts Building, Publix, Target, Walmart Neighborhood Market and more are conveniently located approx 2 miles away. Walmart Superstore is approx 3 miles away, Honeymoon Island Beach is approx 9 miles away and the Tampa International Airport is approx 15 miles away. A walking/running/biking trail is located adjacent to Canal Way, which takes you directly to picturesque Sheffield Park. Whether you are participating in one or more of the many activities offered at the Gull Aire Village clubhouse or just relaxing by the beautiful sparkling pool or spa, you are sure to enjoy the peaceful, friendly Gull-Aire Village atmosphere! Room dimensions are approximate and to be verified by Buyer.

291 Tarpon Lane, Oldsmar

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code

East Lake Woodlands Condominium for sale. 2 bedrooms and 2 bathrooms. This unit is freshly painted and ready for your personal touches. Best priced unit in the community to allow for updates. Enjoy a serene pond view from your screened balcony. East Lake Woodland is a beautifully kept, gated community located within Oldsmar close to restaurants, entertainment, shopping, golf, movie theatre and more. Make your appointment today!

276 Cypress Lane, Oldsmar

4 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code

HIGH AND DRY!! NO STORM SURGE /WATER DAMAGE TO HOME FROM HURRICANE HELENE!! BEAUTIFUL WATERFRONT TOWNHOME IN THE GATED COMMUNITY OF BAYSIDE TERRACE! RARE OPPORTUNITY, THESE LARGER TOWNHOMES WITH 2587 SQ FT RARELY COME ON THE MARKET, AND VERY FEW ON THE WATER! Spectacular WATER & SUNSET VIEWS from the entire downstairs! The owner renovated the 4th bedroom into an office/den to take even more advantage of the water views, making this a ONE OF A KIND OPEN FLOORPLAN. (You can easily turn it back into a bedroom if needed, with french doors or a barn style door.) You will LOVE the spacious great room with HIGH CEILINGS and luxurious feel. The kitchen is an entertainers dream, with a HUGE ISLAND, seating for 4 at the breakfast bar, and a side buffet counter/bar with BEAUTIFUL GLASS FRONT CABINETRY, walk in pantry, granite counter tops, stainless steel appliances, custom lighting, and FARM SINK. Enjoy the tranquility of the covered, screened, raised lanai that offers a serene view of the water/conservation and did I mention gorgeous sunsets? The lanai is also hot tub ready with an upgraded power source for that purpose! A gorgeous, iron staircase leads up to a HUGE bonus room, perfect for game night! The owners suite is upstairs and has an amazing view from the bedroom and the bathroom!! The master bath has stunning granite countertops, SPLIT VANITIES, a soaking tub, and separate shower. Also a HUGE walk in closet and separate water closet for privacy. Split bedroom floor plan offers two more bedrooms and another full bath upstairs. Extra 57k in builder upgrades, include a security system, water softener, lighting, ELECTRIC SHADES in master and office, upgraded power source on lanai to add a spa, extended island, upgraded cabinets and more! This is townhome living at it's best! Sunrise to sunset, enjoy the RESORT like amenities that include gas BBQ grills, dining tables, A WELL EQUIPPED GYM, gas fire pit, pier, fishing, KAYAK STORAGE LAUNCH and BEAUTIFUL INFINITY POOL, all waterfront on the bay! YOUR FURRY FRIENDS ARE WELCOME here without weight or breed restrictions (please refer to current HOA docs to verify) BRING YOUR KAYAK, and launch from the dock area, where there is also storage for the kayaks as well! Such an awesome outdoor area, with lots to do! What more could you want? Gated community, green space, guest parking, security cameras 24/7, pet stations and secure mailboxes. So much to do nearby, with Safety harbor shopping and festivals, world famous Safety Harbor Spa within 5 minutes, Countryside mall, movies, restaurants, and more! GREAT LOCATION, with easy access to both sides of the bay and Less than 15 miles to famous Clearwater Beach, Honeymoon & Caladesi Island State Parks and both Tampa Int'l airport, and ST Pete/Clearwater airport!! WATERFRONT MAINTENENCE FREE LIVING AND EXCEPTIONAL AMENITIES make this a perfect place to call home! Monthly HOA fees include water, trash, cable, WIFI, internet, exterior painting, roof and grounds maintenance! Nothing for you to do but enjoy that view and the Florida lifestyle!! Measurements are estimated, must be verified for accuracy.

9009 Palm Key Avenue, Oldsmar

Start Your Search