Oldsmar Homes with Three+ Story Style

Oldsmar Homes with Three+ Story Style

Welcome to Oldsmar, Florida—a hidden gem nestled in the heart of Pinellas County! Known for its charming small-town vibe, Oldsmar offers a delightful blend of natural beauty and urban conveniences. With its scenic parks, picturesque waterfront, and a thriving community spirit, it's no wonder that residents find joy in calling this vibrant city home.

Oldsmar is strategically located between Tampa and Clearwater, providing easy access to stunning Gulf Coast beaches, world-class dining, and exciting entertainment options. The city's commitment to preserving its natural landscapes is evident in the numerous parks and recreational areas, perfect for outdoor enthusiasts and families alike. Whether you enjoy hiking, biking, or simply taking a leisurely stroll, Oldsmar's lush surroundings offer something for everyone.

For those seeking a unique living experience, Oldsmar boasts an impressive selection of three-plus story homes that redefine modern living. These stunning residences are designed with elegance and functionality in mind, often featuring spacious layouts, panoramic views, and luxurious amenities. Imagine waking up to breathtaking sunrises from your private balcony or hosting gatherings in your expansive living spaces. With ample room for family and friends, these homes are perfect for creating lasting memories.

Living in a three-plus story home in Oldsmar means embracing a lifestyle of comfort and convenience. With close proximity to top-rated schools, shopping centers, and recreational facilities, everything you need is just a stone's throw away. Discover the charm of Oldsmar and explore the possibilities that await you in this enchanting city—your dream home is just around the corner!

Newest Oldsmar Homes with Three+ Story Style

3 Beds ⋅ 3 Baths ⋅ OM728969 MLS ⋅ 158 BLDG.

Endless sunsets create this picture-perfect location in Seaside Estates. Resting on the banks of Old Tampa Bay, where everyday living feels like a vacation. This townhome has 3 bedrooms, 3 bathrooms, and 1,834 square feet of thoughtfully designed living space. The main living level, high ceilings, skylights, and oversized windows frame breathtaking open-water views and unforgettable sunsets. A spacious bedroom with a full bath is also located on this level, ideal for guests or flexible living. The top floor is home to the owner’s retreat, complete with a private balcony, double walk-in closets, a garden tub, separate shower, and dual vanities. An additional bedroom with a full bath and a conveniently located laundry area complete the upper level. The first level features a tandem 3 car garage offering enough space to store your water toys and vehicles. There is newly installed epoxy flooring, extra storage under the stairs, and a covered patio perfect for a grill. A deeded boat slip with a new 7000lb. electric lift is right outside the unit. Just steps from the pool, spa, and tennis courts, this community invites an active waterfront lifestyle. Launch a kayak into nearby mangroves, stroll the expansive boardwalk while watching dolphins and manatees, or enjoy the heated pool, playground, picnic areas, and harbor views. With minimal pet restrictions and HOA fees that include roof, exterior paint, water, sewer, exterior insurance, trash and amenities, living here is truly effortless. Located in the heart of Oldsmar, you’re just steps from R.E. Olds Park, a 15-acre waterfront park offering sweeping views of Tampa Bay. From seasonal festivals and community events to a 400-foot fishing pier and playground, this vibrant park is truly an extension of your neighborhood. With Pinellas beaches, Tampa International Airport, and downtown Tampa all nearby, you’ll enjoy easy access to everything the Tampa Bay area has to offer.

158 Brent Circle, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8504789 MLS ⋅ Seaside Estates BLDG.

Are you dreaming of your own stylish urban OASIS surrounded by nature yet minutes from everywhere you want to be? Experience effortless coastal living in this exceptional waterfront townhome, perfectly designed for those who appreciate space, light and direct access to the water. Featuring two private boat slips, this residence offers a RARE opportunity to keep your vessels close and enjoy days on the water at a moment's notice. Inside, the home unfolds into an open, light-filled floor plan enhanced by soaring high ceilings and expansive windows that invite natural light throughout the day. The seemless flow between living, dining, and kitchen spaces creates an ideal setting for both RELAXED everyday LIVING and entertaining. Water views provide a constantly changing backdrop, adding a sense of CALM and CONNECTION to the outdoors. The generous layout offers flexibility for hosting family and guests, while the airy ceiling heights add architectural drama and a sense of openness rarely found in townhome living. Whether you're enjoying quiet mornings with coffee by the water or gathering with friends after a day on the boat, this home adapts effortlessly to your lifestyle. Outdoor living is just as compelling, with immediate access to the waterfront and your own boat slips just steps away - perfect for boating, paddleboarding, or sunset cruises. This is a home that blends convenience and luxury, offering the maintenance ease of a townhome with the experience of a private gated waterfront retreat. Ideally suited as a primary residence or a refined second home, this property delivers the best of waterfront living - space, light, and direct access to the water- all in one elegant package.

119 Brent Circle, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8513394 MLS ⋅ 120 BLDG.

Come and tour this cozy 3 bedroom, 3 bathroom waterfront townhouse and you will quickly see how easy it is to embrace the lifestyle that makes Florida living so desirable. This 1834 sq ft, 3 level townhouse delivers comfortable maintenance free living in a space where you can be in for years to come. Soak in endless water views as you sip your morning coffee or unwind with a good book, from 2 balconies to choose from. Sky lights brighten up multiple spaces in the home capturing natural night. Enjoy a slice of your own paradise with this sensible buy!” Not only does it give you endless water views, private tennis courts, playground, community pool area, this gated community also Includes your own deeded dock with a new seawall. The garage can fit up to 3 vehicles providing abundant storage. NO OUTSTANDING ASSESSMENTS.

117 Brent Circle, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8507555 MLS

Must see this amazing home in one of Oldsmar's best kept secret neighborhoods on the sparkling shores of Old Tampa Bay! This 3-bedroom, 2.5-bath multi-level designed home has been FULLY RENOVATED with real class blending coastal charm with PRISTINE UPDATES in every room. Above the Oversized 2-car garage, get ready to be impressed by the high ceilings, all NEW WINDOWS, DOORS & light filled living spaces amongst the refinished oak hardwood & gorgeous porcelain ceramic tile flooring throughout. NEW ROOF 2024! STAIRS & DECKS REFURBISHED! The STUNNING KITCHEN has QUARTZ countertops & stainless steel appliances opening into the living and grand dining rooms with french doors onto the enormous covered deck. It's perfect for entertaining and family time. Upstairs you find 3 good sized bedrooms and 2 full bathrooms. The primary suite features french doors to its own private balcony along with a spa inspired ensuite bathroom featuring a luxurious freestanding tub & separate shower that feels straight from a boutique retreat. Not only is this home perfect for all your year round outdoor activities, you can even cozy up by the wood burning fireplace during cold times. The 2 car garage offers exceptional storage space for all the extras, while the oversized back yard opens the door to endless possibilities to make it your new tropical paradise with room for a pool, gardens, boat or RV parking, and even a potential in-law suite. Just minutes from several Waterfront Parks (R.E. Olds Park is biking distance), Scenic trails, Boat ramps, Fishing, Tennis, Pickle ball, Golfing, Tampa Bay Downs, Shopping, Restaurants, and Top Rated Schools in this location, you truly have it all!

3071 Huron Avenue, Oldsmar

4 Beds ⋅ 3 Baths ⋅ TB8496402 MLS ⋅ 138 BLDG.

Welcome to 138 Brent Circle in desirable gated Seaside Estates—an exceptional opportunity to own the largest corner townhome in this sought-after waterfront community in Oldsmar. Perfectly positioned to capture panoramic views of Tampa Bay, this residence offers a rare combination of space, scenery, and coastal lifestyle, complete with a private boat slip for easy access to the water. This spacious 4-bedroom, 3-bath home features a thoughtfully designed layout with abundant natural light and comfortable living areas ideal for both everyday living and entertaining. The inviting living room is anchored by a cozy fireplace, creating a warm focal point while showcasing the stunning water views beyond. A second fireplace in the primary bedroom adds an extra layer of comfort and charm, creating a relaxing private retreat. The kitchen offers ample cabinetry and workspace, seamlessly connecting to the dining and living areas for a functional, open feel. Each bedroom provides flexibility for a variety of living arrangements, while the three full bathrooms add convenience and comfort. An oversized garage delivers generous storage and parking space—an added benefit rarely found in townhome living. As a corner unit, the home enjoys enhanced privacy and additional natural light. Step outside and take in the tranquil waterfront setting, where you can relax, entertain, or set out for a day on Tampa Bay directly from your own boat slip. Conveniently located near parks, shopping, dining, and major roadways, this property offers the perfect blend of peaceful coastal living and everyday accessibility. Don’t miss your chance to own a premier waterfront residence in Seaside Estates—schedule your private showing today.

138 Brent Circle, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8483935 MLS ⋅ 108 BLDG.

Welcome to coastal lifestyle living in one of Oldsmar’s most desirable gated waterfront communities called Seaside Estates. This beautifully maintained home offers the perfect blend of comfort, convenience, and outdoor living just minutes from Tampa Bay. Step inside to an open-concept floor plan filled with natural light, high ceilings, and spacious living areas designed for both everyday living and entertaining. Sliding glass doors create a seamless connection between indoor and outdoor spaces, while the private patio provides the perfect setting for relaxing evenings. The home features a spacious primary suite with ensuite bath, additional guest accommodations, and a flexible office or study space ideal for remote work or hobbies. The open kitchen flows naturally into the main living area, creating an inviting atmosphere for gatherings. Additional highlights include walk-in closets, a cozy fireplace, and an oversized tandem garage offering plenty of storage. Recent improvements include a new A/C system 2022 and water heater installed 2025, with roof updates completed in 2017, offering peace of mind for future homeowners. Residents enjoy exceptional community amenities including scenic waterfront boardwalks, fishing pier, kayak and small-boat access, and peaceful water views where dolphins and manatees are frequently seen. Walking trails, parks, playgrounds, and picnic areas create a relaxing park-like setting within the neighborhood. Conveniently located near Tampa International Airport, downtown Tampa, Ybor City, shopping, dining, and Gulf beaches, this home offers the perfect balance of tranquility and accessibility. Experience the best of Florida coastal living in Oldsmar.

108 Brent Circle, Oldsmar

4 Beds ⋅ 3 Baths ⋅ TB8485835 MLS

One or more photo(s) has been virtually staged. HUGE PRICE ADJUSTMENT JULY 18TH. Gorgeous water views of Old Tampa Bay from this custom-built, original-owner home in a prime Oldsmar location, directly across from popular R.E. Olds Park with its amphitheater, fishing pier, playgrounds, sand volleyball and annual fireworks you can enjoy from your front porch. The resort-style backyard features a large in ground pool with spa, kiddie pool, spillover fountain and fiberoptic lighting, all within a screened enclosure with covered area for dining and parties would cost well over $100k to install today. A spacious concrete pad doubles as a basketball court and offers room to store a boat or add a shed, plus parking for 2 cars under carports and a deep driveway that has accommodated 10+ vehicles, with overflow available at the park. Upstairs, the main living level welcomes you through double hurricane-rated doors to beautiful Brazilian hand-scraped wood floors, abundant windows, and an eat-in kitchen with granite counters and arched opening to the living room, along with a formal dining room. An office or bedroom on this level opens via sliding glass doors to a balcony overlooking the pool, and a convenient half bath completes the floor. The bedroom level begins with a newer washer/dryer closet for easy access to all bedrooms. The primary suite offers stunning water views from sliders, the third-level deck and multiple windows, and its ensuite bath was updated in 2017 with new cabinetry, tile and quartz counters; the second full bath was also updated. Major updates include a 2016 roof and 2023 A/C, making this well-maintained home ideal for both everyday living and large gatherings.

402 Shore Drive W, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8462407 MLS ⋅ 116 BLDG.

Elevated Gated Community. WATERFRONT 3 bedrooms, 3 full baths plus a tandem 2-3 car garage with sliders to a first, second and third floor patios, the patios overlook the dock and boat slip that come with the townhome. The kitchen is open to the dining and family rooms. One bedroom and full bath is located on the main level, while the master suite, and the 3rd bedroom both with full bathrooms are located on the top floor along with the laundry closet. The oversized master features two walk-in closets and floor to ceiling windows with sliders out to one of two private balconies in the home. The master bath has a walk-in shower, garden tub, and dual sinks. High ceilings throughout the home. A must see! Seller is motivated! LET'S MAKE A DEAL!

116 Brent Circle, Oldsmar

3 Beds ⋅ 3 Baths ⋅ O6357016 MLS ⋅ 140 BLDG.

Seller Motivated! Asking price is under last appraisal value. Come take a look at this beautiful 3 bedroom, 3 bath bay front townhome overlooking Old Tampa Bay and Safety Harbor. Seaside Estates is a gated community, located in the heart of Oldsmar, which offers may options for access to the water, as well as major thoroughfares. 3 Car tandem garage that walks out to a beautiful view, the common area and boat docks. This unit owns Slip 12, with a cover and brand new $17,000 boat lift. One of two grandfathered in with covered biminy top. Stainless Steel appliances, wood flooring, renovated spare bathrooms, and spacious balconies from the great room, and the primary bedroom as well. A wood burning fireplace is also located in the primary bedroom for those cosy nights overlooking the water. The spacious floor plan beautiful water views. Seaside estates is a golf cart-friendly community, offering amenities such tennis and pickelball courts, a swimming pool and Jacuzzi. There is a dock area that offers fishing opportunities and houses the particular residents that own boat docks. Located on a few minutes away from waterfront public parks, recreational facilities, and restaurants. 20 events annually are hosted by the community annually, with monthly dinners strategically planned around the scenic Tampa Bay. This neighborhood is just minutes from downtown Oldsmar and Safety Harbor which have a variety of restaurants, nightlife, street and music festivals, walking and biking trails, kayaking, Seaside estates is also pet friendly. 20 min to Caladesi State Park and the pristine Honeymoon Island and 20 minutes to Tampa Airport and 30 minutes to downtown Clearwater. Come take a look at this waterfront gem. Some of these photos have been virtually staged.

140 Brent Circle, Oldsmar

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