Oldsmar Homes with Bay Front Water Frontage

Oldsmar Homes with Bay Front Water Frontage

Welcome to Oldsmar, Florida—a hidden gem nestled in the heart of Pinellas County, where the charm of small-town living meets the beauty of nature. This vibrant city, conveniently located between Tampa and St. Petersburg, offers an inviting atmosphere perfect for families, retirees, and everyone in between. With its picturesque parks, delightful local shops, and a strong sense of community, Oldsmar has become a sought-after destination for homebuyers looking to embrace the Florida lifestyle.

One of the most enchanting features of Oldsmar is its stunning bay front waterfront properties. Imagine waking up to the gentle sound of waves lapping against the shore, with panoramic views of the sparkling waters of Tampa Bay right from your window. Homes with bay front waterfrontage in Oldsmar offer not just a place to live, but a lifestyle characterized by tranquility and outdoor adventure. Whether you enjoy boating, fishing, or simply soaking in the sun, these properties provide direct access to a myriad of aquatic activities.

Oldsmar is also known for its well-maintained parks and recreational facilities, perfect for families and nature enthusiasts. The city's commitment to preserving its natural beauty is evident in the lush landscapes and vibrant wildlife that surround you. With a strong sense of community and a rich array of amenities, Oldsmar is not just a place to call home—it's a way of life. Explore the captivating waterfront properties and discover the serene charm that awaits you in Oldsmar, where your dream home is just a bay breeze away!

Newest Oldsmar Homes with Bay Front Water Frontage

3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code

Endless sunsets create this picture perfect location in Seaside Estates, situated on 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. Upstairs on 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 suite 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 ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code

Imagine coming home to breathtaking waterfront surroundings, resort-style amenities, and maintenance-free living in one of Tampa Bay's most desirable gated communities. Welcome to Bayside Terrace, where this beautifully upgraded 3-bedroom, 2.5-bath townhome with a 1-car garage offers the perfect blend of luxury, convenience, and coastal lifestyle. Ideally situated just steps from the community pool and clubhouse, this move-in-ready residence features one of the community's most desirable locations with peaceful courtyard views and easy access to all the amenities. Designed for today's lifestyle, the open-concept floor plan showcases soaring ceilings, abundant natural light, and elegant wood-look tile flooring throughout the main living areas. The chef-inspired kitchen is the centerpiece of the home, featuring stunning quartz countertops, custom all-wood cabinetry with pull-out shelving, a large quartz preparation island, designer lighting, a walk-in pantry, stylish backsplash, and premium stainless steel appliances including a double oven range and French door refrigerator. Whether entertaining guests or enjoying quiet evenings at home, this space was designed to impress. The spacious great room flows seamlessly onto the covered and screened lanai, creating an inviting indoor-outdoor living experience overlooking a tranquil courtyard. It's the perfect setting for morning coffee, evening cocktails, or simply relaxing after a day on the water. Upstairs, a versatile loft provides flexible living space that easily serves as a home office, media room, fitness area, or second family room. The luxurious owner's suite offers a true retreat with an oversized walk-in closet, dual vanities, linen storage, and a beautifully Upstairs, a versatile loft provides flexible living space that easily serves as a home office, media room, fitness area, or second family room. The luxurious owner's suite offers a true retreat with an oversized walk-in closet, dual vanities, linen storage, and a beautifully appointed frameless glass shower. Two additional bedrooms each feature walk-in closets, ceiling fans, and upgraded carpeting with premium padding for exceptional comfort. Living in Bayside Terrace means enjoying a true Florida waterfront lifestyle. Residents have exclusive access to a resort-style swimming pool, fitness center, clubhouse, fishing pier, kayak launch, and direct access to the beauty of Tampa Bay. Whether you enjoy kayaking, fishing, walking along the waterfront, or simply watching spectacular sunsets, every day feels like a vacation. Perfectly positioned between Hillsborough and Pinellas Counties, this exceptional location offers convenient access to Tampa International Airport, St. Pete-Clearwater International Airport, downtown Tampa, St. Petersburg, award-winning Gulf beaches, waterfront dining, shopping, entertainment, and major employers. Whether you're searching for a waterfront townhome, a gated community with resort amenities, a low-maintenance primary residence, a second home, or a Florida retreat close to Tampa and the Gulf Coast, this exceptional property offers everything today's buyers are looking for. Experience waterfront living at its finest. Schedule your private showing today and discover why Bayside Terrace continues to be one of Tampa Bay's most sought-after communities.

2410 Arch Avenue, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code

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

5 Beds ⋅ 4 Baths ⋅ Country Club Add To Oldsmar Rev SubDv. ⋅ 34677 Zip Code

Unique opportunity to own a one-of-a-kind, beautiful property on Safety Harbour Bay with Direct access to Tampa Bay. Renovation by Herman Builders. The stunning modern completely updated home features: contemporary, Open and spacious Gourmet Chef's Kitchen High-end chef-quality appliances, with double ovens, fireplace Oversized Island loads of cabinets, storage , the home has natural stone floors throughout. Full water views across the entire back of the home large glass doors leading out to your beautiful contemporary pool. Boat Docs for keeping your boat and easy access to Tampa Bay for the deep water fishing. The home features mother-in-law's quarters separate from the main home. With kitchenette, and private entrance . On the main floor, there are also three Guest or family bedrooms a bonus space, laundry room , lots of storage. The Private owner's suite features a large spa bathroom fabulous walk-in closets with grand views of Safety Harbor bay. Conveniently located near airport and downtown with the best schools in Tampa.

412 Shore Drive E, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code

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.

117 Brent Circle, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Oldsmar Country Club Estates Sec 1 SubDv. ⋅ 34677 Zip Code

Some photos have be virtually staged. Beautifully renovated 3 bedroom 2 bath in desirable Oldsmar neighborhood. Spacious floorplan with a large living area at the front allows flexibily for furniture. The kitchen has a modern feel with and all appliances. Both baths have been tastefully upgraded in a contemporty style and home is move in ready. Convenient inside laudry room is a special feature. You'll love the separate shed and large yard. This home is conveniently located by 2 parks and a public boat ramp.Restaurants, shopping and airport are nearby for your convenience.

343 Shore Drive E, Oldsmar

4 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code

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 ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code

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 ⋅ Oldsmar Rev Map SubDv. ⋅ 34677 Zip Code

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 ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code

NEW PRICE!!! Enjoy all the features this home has to offer at a more attractive price. The perfect opportunity for buyers ready to make a move! Welcome to this stunning gated luxury townhome in the highly sought-after waterfront community of Seaside Estates! This beautifully maintained residence offers an exceptional blend of comfort, style, and coastal living. The open-concept main level features gorgeous bamboo hardwood flooring, a cozy fireplace, and a private balcony with scenic views, while the expanded kitchen (extended by 3 feet in 2021) provides extra functional space for everyday living and entertaining. This spacious floor plan includes 3 full baths and a flexible main-level third bedroom perfect for a home office, study, or guest retreat. The impressive primary suite features a private balcony, soaring ceilings, dual walk-in closets, and a spa-like bath, while bedroom two offers an ensuite bath and tranquil water views of Tampa Bay. The oversized 2–3 car tandem garage offers abundant storage and sliding doors to a ground-level patio with access to the dog walking trail. Residents enjoy a resort-style pool and spa, tennis courts, scenic boardwalk, and a community day dock with direct Tampa Bay access for kayaking or small boats, all just minutes to top dining, shopping, beaches, Tampa International Airport, and only a short walk to R.E. Olds Waterfront Park. Extensive updates include bamboo flooring (2021), kitchen expansion (2021), updated light fixtures and interior paint (2021), roof (2017), A/C (2013), water heater (2019), new toilets (2025), new faucets (2026), new washer (2025), blinds including electric living room blinds (2016), balcony floors painted (2025), balcony railing painted (2024), and quality appliances including GE washer (2024), GE cooktop (2021), LG refrigerator (2021), Bosch microwave drawer (2021), Blomberg dishwasher with panel (2021), and Hauslane range hood (2021). Immaculate and move-in ready — schedule your private showing today!

106 Brent Circle, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Country Club Add To Oldsmar Rev SubDv. ⋅ 34677 Zip Code

STUNNING TAMPA BAY VIEWS! UPDATED OLDSMAR SPLIT-LEVEL WITH RV/BOAT PAD! Breathtaking Tampa Bay views await in this updated, elevated home in one of Oldsmar’s most desirable neighborhoods! Just steps from the water, this 3-bedroom, 2-bath residence offers the perfect blend of peace of mind and outdoor living. The split-level design ensures durability, with a spacious 2-car garage on the ground level and all living areas elevated. Major upgrades include a new roof, a newer water heater (<5 years), and a renovated primary suite featuring a walk-in closet. The kitchen shines with stylish quartz countertops, and a large first floor laundry room. Step outside to your fully fenced, level backyard—ideal for entertaining or relaxing in the screened-in porch. The property includes a dedicated RV or Boat pad. Enjoy an incredible lifestyle within walking distance or take your golf cart to the waterfront parks, nature trails, pickleball courts, a fishing pier, and playgrounds. Located in a top-rated school district. This home is the complete package.

317 Shore Drive E, Oldsmar

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

Searching for a low-maintenance waterfront escape in Tampa Bay? Whether you’re looking for a full-time residence, seasonal escape, or the perfect “Lock Up & Go” second home, this property offers the ideal blend of low-maintenance living and resort-style amenities. An added bonus — the flood insurance is ASSUMABLE to new buyers at currently only $1,101 annually. The HOA includes cable, internet, water, trash, roof and grounds maintenance, and gated access, leaving electricity as the only additional utility needed. This rare oversized waterfront unit stands out as one of the few in the community with expanded water views from the main living areas, creating a brighter, more open feel throughout the home. Enjoy stunning bay and conservation views from the kitchen, dining, living room, and even the primary suite upstairs. High ceilings and an open-concept layout make the home feel spacious and inviting, while the upgraded kitchen was designed with entertaining in mind. Features include an extended island, side coffee/bar station with glass-front cabinetry, spacious walk-in pantry, and over $57,000 in builder upgrades throughout the home. Upstairs, the waterfront owner’s suite feels like a private retreat with beautiful water views, dual vanities, soaking tub, separate shower, and an oversized walk-in closet. Two additional bedrooms plus a generous bonus room provide flexible space for a media room, game room, second living area, or hosting guests. The oversized upstairs laundry room located just off the primary suite adds everyday convenience. Downstairs, the current office can easily be converted back into a fourth bedroom if desired. Step outside to your screened lanai and enjoy peaceful mornings or sunset evenings overlooking the water. Bayside Terrace offers RESORT-STYLE amenities including an infinity pool overlooking Old Tampa Bay, waterfront fire pit, fitness center, outdoor grills, kayak launch and storage, and a waterfront pier perfect for fishing or relaxing by the water. LOCATION, LOCATION, LOCATION — conveniently located just minutes to downtown Oldsmar, approximately 10 minutes to Safety Harbor, 20 minutes to Dunedin and Honeymoon Island, 25 minutes to Tampa International Airport, and 30 minutes to Clearwater Beach. This is waterfront living designed for both everyday enjoyment and effortless second-home ownership. You truly have to see it in person.

9009 Palm Key Avenue, Oldsmar

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