Oldsmar Homes with Bay View Water Frontage

Oldsmar Homes with Bay View Water Frontage

Welcome to Oldsmar, Florida—a hidden gem nestled in the heart of Pinellas County, where the warmth of the sun meets the tranquil embrace of the waterfront. Known for its charming small-town vibe and vibrant community, Oldsmar is a delightful blend of natural beauty and modern conveniences. With its proximity to the stunning Gulf Coast, residents enjoy an array of outdoor activities, from boating and fishing to hiking and biking along scenic trails.

One of the most captivating features of Oldsmar is its stunning homes with bay view waterfrontage. Imagine waking up each morning to the gentle sound of waves lapping against the shore, with breathtaking views of the bay right outside your window. These waterfront properties offer not just a home, but a lifestyle—a chance to immerse yourself in the serene beauty of nature while enjoying the comforts of modern living.

Oldsmar's real estate market boasts a variety of homes that cater to different tastes and budgets, all while providing easy access to the shimmering waters of Tampa Bay. Whether you're seeking a cozy bungalow or a luxurious estate, there's something for everyone in this picturesque community.

In addition to its natural allure, Oldsmar is conveniently located near top-rated schools, shopping centers, and dining options, making it an ideal place for families, retirees, and everyone in between. Come and discover the charm of Oldsmar, where your dream home by the water awaits!

Newest Oldsmar Homes with Bay View Water Frontage

$349,000
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.

604 Chestnut Street, Oldsmar
$559,000
5 Beds ⋅ 3 Baths ⋅ Oldsmar Rev Map SubDv. ⋅ 34677 Zip Code
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.

604 Chestnut Street, Oldsmar
$379,900
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
THE KITCHEN SETS THIS ONE APART. Step into a brighter, more open 3-bedroom, 3-bathroom townhome with over 1,800 square feet in the gated waterfront community of Seaside Estates. Bamboo flooring, a fireplace, high ceilings, and a private balcony create a light-filled, open-concept main level. The kitchen was extended 3 feet and the original dropped ceiling was removed, so the space feels tall and open to the living room -- a difference most of the 67 units in this community still don’t have. Quartz counters, new white cabinetry, stainless appliances, and a built-in pantry finish the update. A flexible bedroom on this level works as an office or guest suite. Upstairs, the primary suite offers soaring vaulted ceilings, dual walk-in closets, skylights, its own balcony, and a spacious ensuite, with laundry and a third bedroom with an ensuite bath on the same level. The oversized tandem garage adds storage and sliding-door access to a patio and green space. This building sits closer to the tennis court and main entrance, and farther from the pool noise. Residents share a resort-style pool/spa, tennis, boardwalk, and a floating dock for kayaks and paddleboards, with slips and boat lifts typically available to rent. Inclusive HOA fees cover the roof (2017), water, sewer, trash, and interior fire sprinklers. Just steps from R.E. Olds Park, a 15-acre waterfront park with the city pier, playgrounds, trails, beach volleyball and more, plus convenient access to Gulf Coast beaches, Tampa International Airport, Clearwater, and Tampa/St. Pete. Schedule your showing today!

106 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
$510,000
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
$475,000
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. NO OUTSTANDING ASSESSMENTS.

117 Brent Circle, Oldsmar
$399,000
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
$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
$725,000
4 Beds ⋅ 3 Baths ⋅ Oldsmar Rev Map SubDv. ⋅ 34677 Zip Code
One or more photo(s) has been virtually staged. PRICE ADJUSTMENT August 30th $33k below Zestimate. 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
$484,700
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
$545,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
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. 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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