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Waterfront Homes for Sale in Oldsmar, FL

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Welcome to your dedicated resource for waterfront homes for sale in Oldsmar, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Oldsmar, FL agents, Joseph Sullivan Real Estate specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the waterfront properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Waterfront Homes for Sale in Oldsmar, FL

3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv.

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.

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 ⋅ 2 Baths ⋅ Shoreview Ph 2 SubDv.

BACK ON THE MARKET – PREVIOUS BUYERS FINANCING FELL THROUGH! Opportunity awaits at this charming 3-bedroom, 2-bath ranch-style home situated on a peaceful pond in Oldsmar. Built in 1984, this single-story residence offers a comfortable floor plan, abundant natural light, a two-car garage, and a beautiful setting beneath mature shade trees. Step outside and discover what makes this property special. The backyard overlooks the pond, creating a tranquil setting surrounded by mature trees and established landscaping. The screened lanai provides additional outdoor living space and is the perfect place to enjoy your morning coffee, entertain friends, or simply relax while taking in the peaceful waterfront views. Inside, the home offers a functional layout with plenty of opportunity to update and personalize the space to your taste. Whether you're an owner-occupant looking to create your ideal home or a buyer searching for a property with sweat-equity potential, 627 Timber Bay offers an excellent foundation and an increasingly hard-to-find combination of location, lot, and waterfront setting.Adding even more value, a NEW ROOF WAS INSTALLED IN 2026, taking care of one of the home's most significant improvements. Conveniently located in Oldsmar, with easy access to shopping, dining, parks, schools, and major roadways connecting Tampa, Clearwater, and the surrounding Tampa Bay area. Waterfront setting. New roof. Mature trees. Screened outdoor living. Two-car garage. Tremendous potential. Bring your vision and make 627 Timber Bay your own. Schedule your showing today and come experience the setting and possibilities this property has to offer.

627 Timber Bay Circle W, Oldsmar

3 Beds ⋅ 2 Baths ⋅ West Oldsmar Sec 1 SubDv.

Welcome to this unique elevated waterfront 3 bedroom, 2 bathroom, oversized 2 car garage home located at 3858 Shore Boulevard that offers close to 1,600 square feet of living space and has an additional 600+ square foot in-law suite / ADU situated in the laid back town of Oldsmar, Florida. This serene waterfront property offers the perfect balance of peaceful living and convenient access to local attractions and is nestled between Tampa and Clearwater. Residents here enjoy a tranquil, private environment, starting mornings with fresh coastal breezes on a private porch or deck, and spending evenings watching sunsets from a kayak or boat. This elevated, two-story home, topped with a 2025 roof, showcases an expansive layout filled with radiant natural light and soaring vaulted ceilings. The interior ambiance is both airy and welcoming, anchored by a charming wood-burning fireplace. The heart of the home is a sun-drenched, open-concept great room and kitchen, equipped with stainless steel appliances, granite surfaces, a propane stove, and a tankless water heater, all showcased by floor-to-ceiling windows. The generous primary suite acts as a private retreat, featuring an ensuite bathroom with a garden tub, dual vanities, and a separate shower, alongside a private deck offering stunning vistas. The main living quarters are elevated to stay secure and dry even in severe weather, while expansive windows frame views of dolphins, manatees and unique local birds. Enjoy the outdoors from a variety of living areas such as decks, patios and screened-in porches, or cast a line from your own floating dock and set out from your private boat ramp; the canal can handle bigger boats and provides direct access to all of Tampa Bay and the St. Petersburg shoreline just beyond your property. A paved driveway provides generous parking and leaves ample room for extra recreational vehicles like boats and RVs and there is plenty of room for a pool. Downstairs there is an extra-large garage for two cars alongside a spacious 600+ square foot ADU, also serving as a mother-in-law suite, which features a separate private entry and is equipped with a bathroom, sink and refrigerator. Set on a quiet cul-de-sac that ensures outstanding seclusion, this home occupies a spacious lot of almost a third of an acre within a highly acclaimed school zone. It is just 20 to 30 minutes away from downtown Tampa, Clearwater and the finest beaches on the Gulf Coast. Within walking distance is the delightful R.E. Olds Park, known for its regular monthly festivals and community gatherings. Downtown Safety Harbor, with its restaurants and entertainment options, can be reached by bicycle or by boat, and both the stunning Phillippe Park and Mobbly Beach Park are under three miles away, also conveniently accessible by bike or water. The city of Oldsmar itself stands out for several reasons: it operates its own reverse osmosis water plant, it is the location of the Tampa Bay Skating Academy ice rink, and it has the highest concentration of parks per square mile in Florida, with approximately 40 percent of its area preserved as parks and nature reserves. Those who love the outdoors will appreciate the ten-mile Oldsmar Trail, which passes through eight of the city's ten parks and provides countless chances for recreation and discovering nature. Do not miss your chance to live the Florida lifestyle you have always wanted — book your private showing of this exceptional property today!

3858 Shore Boulevard, Oldsmar

West Oldsmar Sec 1 SubDv.

NICE WATERFRONT BUILDABLE LOT! LOCATED ON MOCCASIN CREEK WITH EASY ACCESS TO THE BAY! CREEK FRONTAGE IS 50 FEET! NO HOA! LOW TAXES! SHORT DISTANCE TO HONEYMOON ISLAND, PALM HARBOR, BEST GULF BEACHES, SHOPPING, RESTAURANTS & TAMPA INTERNATIONAL AIRPORT! PARTIALLY CLEARED! BUY TODAY AND BUILD AT ANY TIME!

Phoenix Avenue, Oldsmar

4 Beds ⋅ 3 Baths ⋅ East Lake Woodlands SubDv.

One or more photo(s) has been virtually staged. NEW PRICE. SERIOUS VALUE. Located inside the highly desirable gated community of Ardea / East Lake Woodlands, this spacious 4-bedroom, 2.5-bath residence offers an expansive 2,922 sq ft of living space on an oversized lot with peaceful water views. Step inside to soaring ceilings and an open, light-filled floor plan designed for both everyday living and entertaining. The home features expansive living areas including a formal living and dining room and a large family room with fireplace. New Luxury Vinyl Plank flooring installed in 2026 runs throughout the main living areas, creating a modern and cohesive look, while new carpet installed in 2026 adds comfort to the guest bedrooms. The updated kitchen features granite countertops and stainless-steel appliances, flowing seamlessly into the main living space and breakfast area—perfect for gatherings and everyday living. The spacious primary suite offers direct access to the pool area along with a private bath and generous closet space. Enjoy Florida living at its best with a screened pool and lanai overlooking a tranquil pond, providing both privacy and relaxing water views. The home also features fresh exterior paint completed in 2026 and a 3-car garage, all situated on a generous homesite within this established golf-course community. Residents of East Lake Woodlands have the option to join the Ardea Country Club, a recently renovated club offering two championship golf courses, tennis and pickleball courts, fitness facilities, resort-style pool, and multiple dining venues. The club provides a vibrant social calendar and family-friendly amenities, creating a true country club lifestyle right inside the community. Located just minutes from shopping, dining, top-rated schools, and major commuter routes, this home offers convenient access to Tampa International Airport, Gulf beaches, and the best of the Tampa Bay area. Close to all the Tampa Bay Area has to offer; Championship golf courses, Tampa International Airport, NHL, NFL, MLB events, Grand Prix, PGA events, fine dining, concerts, parks, biking trails, BMX events, and more. Begin Your Paradise Life Today.

470 Hickorynut Avenue, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv.

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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