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 allure of waterfront paradise. Situated just minutes from the bustling cities of Tampa and St. Petersburg, Oldsmar offers a unique blend of tranquility and accessibility, making it an ideal place to call home.

Oldsmar boasts a rich history, with roots dating back to the early 1900s. Today, it’s a vibrant community known for its beautiful parks, scenic trails, and family-friendly atmosphere. The city is surrounded by stunning natural landscapes, including the picturesque Old Tampa Bay, which provides residents with breathtaking views and endless recreational opportunities. Whether you enjoy fishing, boating, or simply soaking in the sun, the bay front waterfront homes in Oldsmar are a perfect sanctuary for water enthusiasts.

Imagine waking up to the gentle sound of waves lapping against your dock and sipping your morning coffee while watching the sunrise over the bay. Homes with bay front waterfrontage in Oldsmar offer not only stunning vistas but also a lifestyle filled with outdoor adventures. With a variety of properties ranging from charming cottages to luxurious estates, there’s something for everyone in this idyllic waterfront community.

Explore the friendly neighborhoods of Oldsmar, where you’ll find a strong sense of community and a plethora of local amenities, including shops, restaurants, and entertainment options. Whether you’re looking to settle down or invest in a vacation home, Oldsmar's waterfront properties promise a serene escape and a vibrant lifestyle. Discover your slice of paradise in Oldsmar today!

Newest Oldsmar Homes with Bay Front Water Frontage

131 Brent Circle, Oldsmar
$849,900
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
This rare, customized end unit townhome is located on Old Tampa Bay in Oldsmar in the sought after gated community of Seaside Estates. Enjoy breathtaking open water views from any of the floors largely due to the abundance of windows and 3 generous sized patios/decks. Relaxing will come naturally as you gaze out over the green space, seawall and open water. Home features 1834 sf and 3 bedrooms, 3 baths. There are 2 outside parking spaces within a few feet of the attractive entry to the unit. Upon entering the bottom floor you have a foyer and to the left an oversized 2+ car tandem parking garage with an abundance of storage and rear covered patio. Garage also has a vented portable air conditioner and a dehumidifier creating a perfect storage and work area. The ground entry foyer has stairs leading up to the main living area floor where you are greeted with great light from the multi windows and large deck/patio. It is truly a breathtaking view looking out on Old Tampa Bay. This floor features a living room, dining room, updated kitchen (2019), one bedroom with a built-in murphy bed plus desk and a full bath. Ascending one more floor, there is the master suite with sliders leading to a spacious deck, a second en-suite bedroom with its private full bath. There is also a laundry area with double doors for easy access and stackable washer/dryer. Throughout the wooden floors are beautiful with some tile in the wet areas. Multiple outdoor spaces including the ground floor patio plus oversized patios/decks as one on each floor really expand the living space so you can enjoy the Florida lifestyle throughout this open unit. Don't let the multi-stories be an issue as this unit boasts an ELEVATOR installed 2025 to help you move yourself and your belongs easily throughout. As an added bonus, this unit comes with a DEEDED BOAT SLIP located behind the unit at the mouth of the channel. So whether you prefer fishing from the seawall, inshore fishing or shooting out in the Gulf for a little offshore fishing or just pleasure boating maybe to local restaurants/bars such as close by Jack Willie's, you're ready to go! While feeling very private, this unit offers it all . . . privacy yet close to shopping and restaurants for your daily needs.

131 Brent Circle, Oldsmar
3090 Phoenix Avenue, Oldsmar
$689,000
3 Beds ⋅ 3 Baths ⋅ West Oldsmar Sec 1 SubDv. ⋅ 34677 Zip Code
Imagine waking up to sparkling water views and having the ultimate Tampa Bay lifestyle right in your backyard. Situated in one of the area’s most desirable coastal pockets, this waterfront property offers direct boat access, giving you the freedom to set sail from your private dock and cruise straight to Downtown Tampa or St. Petersburg for dinner and weekend adventures.This is a rare opportunity to secure a prime waterfront canvas and bring your personal vision to life. Whether you dream of crafting a sophisticated coastal retreat or an effortless open-concept sanctuary, this home gives you the freedom to design every detail to your exact taste. Don’t just buy a house—create your dream waterfront lifestyle. Schedule your private tour today and start imagining the possibilities!

3090 Phoenix Avenue, Oldsmar
3825 Shore Boulevard, Oldsmar
$1,915,000
4 Beds ⋅ 4 Baths ⋅ West Oldsmar Sec 1 SubDv. ⋅ 34677 Zip Code
Pre-Construction. To be built. ***Pre-Construction Waterfront Opportunity | Oldsmar, Florida Build Your Vision on Wide-Open Tampa Bay A rare opportunity to create a brand-new luxury waterfront residence overlooking the wide-open waters of Tampa Bay. This pre-construction offering combines an exceptionally Large Oldsmar waterfront homesite with a thoughtfully designed three-level residence created to maximize the views, outdoor living, and Florida waterfront lifestyle. The proposed home features approximately 3,700 square feet of cooled living space with 4 bedrooms, 3.5 bathrooms, and a four-car tandem garage. The three-level design features concrete block construction and an open great-room floor plan with a spacious kitchen, oversized center island, dining area, and expansive living space designed to take advantage of the Open Tampa Bay setting. Covered porches and balconies extend the living areas outdoors, while the upper-level primary suite is positioned to capture the waterfront views. Buyers will also have the opportunity to personalize the home with a choice of beautiful exterior architectural styles, including West Indies, Coastal Contemporary, and Modern Mediterranean. Additional options include a residential elevator and custom pool package at an additional cost. Following the proposed lot split, the homesite is estimated to provide approximately 90 feet of street frontage, 180 feet of depth, and an impressive 99 feet of waterfront frontage on wide-open Tampa Bay. The waterfront land is to be purchased separate from the cost of constructing the home but can be packaged together with a CP Loan allowing buyers to secure the homesite and then move forward with their selected home design, finishes, and available options. All 3 lots are offered at an asking price of $466k each. The build cost is estimated at $1,449,000 without optional Elevator Package (+$80k) & Pool Package (+120K). This Package is for Lot 6 Blk 8 only. *Supplied Home Construction Virtual Renderings are for example only*

3825 Shore Boulevard, Oldsmar
3825 Shore Boulevard, Oldsmar
$1,349,000
West Oldsmar Sec 1 SubDv. ⋅ 34677 Zip Code
Virtually Staged. RARE OPEN TAMPA BAY WATERFRONT OPPORTUNITY — 1.2 ACRES WITH 302 FEET OF WATERFRONT! Opportunities like this are exceptionally hard to find. Situated directly on the wide-open waters of Tampa Bay, this remarkable 1.2-acre waterfront property offers an impressive 302 feet of waterfront frontage and endless possibilities for a homeowner, builder, or investor. This property provides the flexibility to create one spectacular waterfront estate or subdivide into three separate residential lots, presenting an outstanding opportunity to build three custom or spec homes. The sellers are also willing to sell the lots individually, creating additional flexibility for buyers and builders. Imagine designing your dream home on an expansive waterfront homesite with panoramic Tampa Bay views, generous outdoor living areas, a resort-style pool, and plenty of room to create your own private waterfront retreat. For builders and investors, the ability to potentially develop three separate waterfront residences creates a unique opportunity in a market where large waterfront parcels are increasingly difficult to find. Whether your vision is one extraordinary waterfront estate, multiple luxury residences, or an investment development, this property offers the size, frontage, views, and flexibility to make it happen. 1.2 Acres | 302' of Tampa Bay Waterfront | Potential for 3 Lots each measuring 93ft front, 180ft depth, 101ft on water. A truly rare opportunity to secure a substantial piece of Tampa Bay waterfront and bring your vision to life. *The owner has an updated survey pkg ready to submit for separating this one large parcel into 3 evenly split lots

3825 Shore Boulevard, Oldsmar
3010 Palm Key Avenue, Oldsmar
$388,500
2 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code
Welcome to waterfront living at its best! Located on beautiful Old Tampa Bay, this exceptional community offers a relaxed Florida lifestyle with amenities designed for everyday enjoyment and entertaining. Gather with friends around the gas firepit, share a meal beneath the pavilion with two grills, or relax in the large heated infinity pool while taking in beautiful water views. Stay active in the fully equipped gymnasium, fish from the pier extending into the bay, or launch a kayak for an afternoon on the water. The electronically gated entrance provides added security. Ideally situated directly across from the pool, this residence truly stands out. Beautiful landscaping and lush greenery welcome you at the entrance, while thoughtful enhancements continue throughout, including a gleaming epoxy-finished garage floor and garden-like screened porch. The porch creates a wonderful outdoor retreat for morning coffee, relaxing evenings, or entertaining guests. Inside, beauty and functionality continue. The entire first floor features beautiful tile flooring for a polished appearance and easy maintenance. In 2024, all recessed lighting was upgraded to LED bulbs, with downstairs lights featuring dimmers and amber-light options for the perfect ambiance. Even the spacious walk-in pantry has automatic lighting that illuminates the generous storage space when the door opens. The open-concept main living area is perfect for entertaining and everyday life, offering space for a full dining table and casual dining at the granite breakfast bar. Numerous light-gray cabinets provide abundant storage, complemented by a convenient coffee bar and mini-mudroom near the garage entrance. The living area flows effortlessly through pocket sliders to the screened porch, creating a wonderful indoor-outdoor living experience. A conveniently located half bath completes the first floor, while Custom Nantucket remote-control shades provide privacy and light control. Upstairs, a generous flex room offers incredible versatility as a den, second family room, playroom, home office, or temporary third bedroom. The nearby laundry room adds convenience. The primary suite offers a peaceful retreat with an expansive granite double-sink vanity, abundant storage, glass-enclosed shower, beautiful natural light, decorative tray ceiling, and custom walk-in closet with built-in shelving. Custom Nantucket remote shades complete the space. The spacious second bedroom is equally inviting, with natural light, decorative tray ceiling, and exceptional storage. Two closets, including a very large walk-in, provide plenty of room. The second full bath features wood cabinetry, pull-out drawers, granite countertop, and glass-enclosed shower. Additional upgrades include a new electrical panel installed in 2024 and gutters added in 2021 along with the undercounter lighting and downstairs crown molding. The location offers convenient access to Tampa, area airports, major shopping, restaurants, beautiful beaches, and more. With its waterfront setting, resort-style amenities, thoughtful upgrades, flexible living spaces, and outstanding location, this home offers an exceptional opportunity to enjoy the Florida lifestyle.

3010 Palm Key Avenue, Oldsmar
604 Chestnut Street, Oldsmar
$319,000
Oldsmar Rev Map SubDv. ⋅ 34677 Zip Code
Vacant lot for sale. 300 yds from Tampa Bay and 2 blocks from an "A" rated Elementary School. Seller will consider clearing the property if the buyer purchases this lot and the lot next to it with existing structure. Water view!

604 Chestnut Street, Oldsmar
604 Chestnut Street, Oldsmar
$524,000
5 Beds ⋅ 3 Baths ⋅ Oldsmar Rev Map SubDv. ⋅ 34677 Zip Code
MOTIVATED SELLER! Will consider owner financing or partial property trade. Charming older block home. 5 bedroom 3 bath ranch style home in Historic Part of Oldsmar. 300 yds from Tampa Bay and 2 blocks from an "A" rated Elementary School. Home has several upgrades but needs a little TLC. Home sits on 2 lots, and the vacant Lot 13 is available for separate purchase at $349k. You can purchase the house on Lot 12 only for $449k and a leaseback of Lot 13. Water view lots!!

604 Chestnut Street, Oldsmar
129 Brent Circle, Oldsmar
$460,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
HUGE PRICE IMPROVEMENT - WATERVIEWS from All 3 Floors, This UPDATED 3Bed 3Bath townhome is situated in the exclusive gated community of SEASIDE ESTATES in picturesque and historic Oldsmar. Nestled within a Townhome Complex of 67 units, this particular unit stands out as truly unique. The magnificent sunsets are breathtaking. The kitchen has STONE COUNTERTOPS, STAINLESS STEEL APPLIANCES, and offers ease with the CENTRAL VACUUM SYSTEM. Additional highlights include custom-built shelving in both His and Her Primary Closets. The primary suite, located on the third level, boasts a generously sized UPDATED BATHROOMS. The spacious floor plan ensures ample natural light and stunning water views. Enjoy the Florida lifestyle in this golf cart-friendly community, offering amenities such as a swimming pool, Jacuzzi and tennis/pickleball courts. The dock area provides good fishing opportunities, and the residence is only a few minutes away from waterfront public parks, shopping, restaurants, and various recreational facilities. The community hosts more than 20 events annually, with monthly dinners strategically planned around the scenic Tampa Bay. Minutes from downtown Oldsmar and Safety Harbor which offer a variety of restaurants, nightlife, street and music festivals, walking and biking trails, kayaking, This complex is PET FRIENDLY. 20 minutes to Tampa Airport and 30 minutes to downtown Clearwater and world-famous Clearwater Beach, 20 min to Caladesi State Park and the pristine Honeymoon Island.

129 Brent Circle, Oldsmar
158 Brent Circle, Oldsmar
$490,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
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
102 Shore Drive E, Oldsmar
$424,000
3 Beds ⋅ 2 Baths ⋅ Tampashores Hotel Plaza Sec SubDv. ⋅ 34677 Zip Code
Welcome to the TAMPA BAY LIFESTYLE WITHOUT THE WATERFRONT PRICE TAG. This beautifully fully remodeled 3-bedroom, 2-bath home offers the rare combination of modern updates, an incredible location, and exceptional flexibility for homeowners and investors alike. Completely renovated from top to bottom, this move-in-ready home features an open-concept floor plan with luxury vinyl plank flooring throughout, quartz countertops, updated cabinetry, stainless steel appliances, designer fixtures, and beautifully renovated bathrooms. Natural light fills the spacious living areas, creating a bright and inviting atmosphere perfect for everyday living and entertaining. Location is everything, and this one is hard to beat. Situated next to one of Oldsmar’s beautiful waterfront parks and just steps from the fishing pier, playground, walking trails, and scenic Tampa Bay shoreline, this home offers a lifestyle that is difficult to replicate at this price point. Enjoy easy access to dining, shopping, marinas, downtown Safety Harbor, Dunedin, Clearwater, and some of the area’s most popular beaches. Nearby attractions including Tampa Bay Downs, waterfront festivals, and outdoor recreation make this an exceptional place to live, vacation, or invest. Whether you’re looking for a primary residence, first-time home, second home, seasonal retreat, or income-producing investment property, this home offers exceptional flexibility to fit your goals. Currently operating as a successful SHORT-TERM RENTAL/AIRBNB (furniture negotiable). The property provides immediate income-producing potential and an opportunity for investors to capitalize on Oldsmar’s growing demand for vacation and extended-stay accommodations. Recent short-term rental performance included approximately $3,000 in gross rental revenue during a recent five-night stay. Additional highlights include a 2024 roof, no HOA, and convenient access to Tampa, Clearwater, St. Petersburg, Tampa International Airport, shopping, dining, and some of the area’s most popular beaches. Experience the charm of Oldsmar and enjoy the perfect blend of comfort, convenience, and coastal lifestyle. Schedule your private showing today.

102 Shore Drive E, Oldsmar
117 Brent Circle, Oldsmar
$445,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
PRICE IMPROVEMENT! Waterfront Living at Its Best! Live the Florida lifestyle you’ve been dreaming of in this inviting 3-bedroom, 3-bathroom waterfront townhouse offering 1,834 square feet of comfortable, maintenance-free living across three levels. With beautiful water views, two private balconies, and a thoughtfully designed layout, this home is the perfect place to relax, entertain, and enjoy the best of coastal living. Start your mornings overlooking the water, unwind with a good book, or simply take in the peaceful surroundings. Skylights bring in an abundance of natural light, creating a bright and welcoming atmosphere throughout the home. Located within a desirable gated community, this waterfront retreat offers an impressive collection of amenities, including private tennis courts, a playground, and a community pool. Even better, the property includes your own deeded dock and a new seawall, making it easy to embrace the waterfront lifestyle right from your doorstep. The spacious garage accommodates up to three vehicles, offering exceptional parking flexibility and not just additional storage but the ability to create your own home gym space and or workshop. With endless water views, desirable community amenities, and the added value of a deeded dock and new seawall, this is an opportunity to enjoy the Florida lifestyle in a home designed for years of enjoyment. NO OUTSTANDING ASSESSMENTS. Now offered with a price improvement—come see the possibilities and make this waterfront retreat your own!

117 Brent Circle, Oldsmar
108 Brent Circle, Oldsmar
$374,000
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
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