Homes for Sale Between $350,000 to $400,000 in Oldsmar, FL

3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv.

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

$375,000

3 Beds ⋅ 2 Baths ⋅ Shoreview Ph 2 SubDv.

Virtually Staged. Location, location, location — love where you live! This move-in-ready 3-bedroom, 2-bath pool home offers thoughtfully updated living space in the heart of Oldsmar, with an open floor plan and 2-car attached garage. New laminate flooring runs throughout, starting in the light-filled living room just inside the front door. The kitchen opens to the family room, perfect for entertaining. Sliders off the family room open to the pool and fully fenced backyard, extending the living space outdoors. The primary suite includes laminate flooring and an en suite bath with an updated vanity and fixtures. Two secondary bedrooms share a second remodeled bathroom with a tub/shower combination. Additional peace of mind: this home stayed high and dry through the 2024 storms with no reported damage, and comes with a transferable flood insurance policy. Recent updates include, Newer Roof (2020), exterior and interior painting (2026), and lamiinate flooring (2026). Oldsmar is a golf-cart-friendly community with waterfront parks, playgrounds, dog parks, pickleball courts, and year-round events like concerts in the park and seasonal celebrations. You're just blocks from the scenic Tampa Bay shoreline and its beautiful sunrises, close to shopping, dining, golf, and schools — and only 20–25 minutes from Tampa International Airport. An excellent location at an amazing price — Schedule your showing today!

651 Timber Bay Circle E, Oldsmar

$385,000

4 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cluster Homes SubDv.

Welcome to 150 Poole Place, a spacious 4-bedroom, 2-bath villa offering approximately 1,550 square feet of flexible living space in the gated community of East Lake Woodlands. Ideally positioned along the 15th hole of the South Course, this immaculate home offers beautiful golf course views and a peaceful setting that can be enjoyed from multiple areas of the property. Inside, the split-bedroom floor plan provides privacy and versatility, with four bedrooms that can easily accommodate family, guests, a home office, or hobby space. The living room features a decorative electric fireplace that adds character and ambiance, while the kitchen offers generous cabinetry, ample counter space, and all appliances included. An enclosed Florida room expands the living area and creates a comfortable space to relax while overlooking the golf course. French doors, tile flooring throughout, plantation shutters, interior laundry, and ample storage add to the home’s functionality and appeal. Outdoor living continues with patio areas that offer the perfect place for morning coffee, entertaining, or simply enjoying the scenic surroundings. A new water softener system was installed in July 2026. The monthly HOA fee of $490.08 includes internet, cable, building maintenance, roof, and lawn care, providing a convenient low-maintenance lifestyle. East Lake Woodlands is known for its gated setting, mature landscaping, scenic golf course surroundings, and optional country club lifestyle. Golf, tennis, pickleball, swimming, fitness, dining, and social amenities are available through separate club membership. Conveniently located near shopping, restaurants, parks, beaches, airports, and all that the Tampa Bay area has to offer, 150 Poole Place combines space, flexibility, and a desirable golf course setting in one of Oldsmar’s most established communities.

150 Poole Place, Oldsmar

$395,000

3 Beds ⋅ 3 Baths ⋅ Sun Ketch Twnhms At Cypress Lakes SubDv.

Welcome home to this beautifully updated pond front three-bedroom, 2½-bath townhome with a one-car garage in the desirable Sun Ketch community of Oldsmar! Best of all, the low $265/month HOA fee covers exterior maintenance, grounds care, the roof, and offering truly low-maintenance living. Residents also enjoy a community pool just steps from the home, making it easy to relax and enjoy the Florida lifestyle. Step inside to a welcoming foyer with a convenient half bath for guests. Continue into the bright, open-concept main living area, which boasts Travertine tile flooring, and where the beautifully updated kitchen features white cabinetry, quartz countertops, a breakfast bar, ample storage, and a fantastic corner pantry with built-in shelving. The kitchen flows seamlessly into the living and dining room, creating an ideal space for everyday living and entertaining. Pocket sliding doors lead to the screened-in lanai and brick-paver patio, where you can enjoy peaceful pond views and a private, fenced outdoor space. Upstairs, the spacious primary suite is positioned at the front of the home and features vaulted ceilings, an oversized wall closet, and a private en-suite bath with a step-in shower. Down the hall, the beautifully updated guest bath offers a tub/shower combination, while a linen closet provides additional storage. The two secondary bedrooms are located at the rear of the home, with one featuring a sizable walk-in closet and the other offering a generous wall closet. The entire second floor is light and bright with high-volume ceilings and attractive wood-look luxury vinyl plank flooring. Thoughtful storage continues throughout the home, including great under-stair storage, a laundry room with cabinetry, and direct access to the one-car garage. Recent updates in 2023 include quartz kitchen countertops, luxury vinyl plank flooring upstairs, carpeting on the staircase, reglazing of the guest bathtub, four new PGT hurricane rated windows (two double hung in the primary and sliding windows in the rear bedrooms), and a vinyl-coated chain-link fence enclosing the rear patio area overlooking the water. With these improvements already completed, there is truly nothing left to do but move in and start enjoying your new home. Located in a convenient Oldsmar location near Tampa Road, approximately 20 minutes to Tampa International Airport (TPA), St. Pete-Clearwater International Airport (PIE) and popular Honeymoon Island, you’ll also have easy access to restaurants, shopping, and so much more. Add in the community pool, peaceful pond setting, garage, and low-maintenance HOA lifestyle, and this wonderful townhome offers the perfect blend of comfort, convenience, and Florida living. Come see it for yourself!

216 Hemingway Drive, Oldsmar

$365,000

3 Beds ⋅ 2 Baths ⋅ Sheffield Village Ph Ii At Bayside Meadows SubDv.

--SERIOUS SELLER-WILLING TO NEGOTIATE-- Check out this BEAUTIFUL 3-bedroom, 2-bath BLOCK home WITH GARAGE. located on a quiet cul-de-sac in the heart of Oldsmar. BEAUTIFUL HIGH GLOSS TILE FLOORING THROUGHOUT Featuring spacious living areas with vaulted ceilings, a primary bedroom with an ensuite, and a split bedroom layout for added privacy and a rear screened porch perfect for relaxing or entertaining. The home has been thoughtfully upgraded with a new electrical panel (2018), roof (2020), air conditioning system (2021), gutters (2022), garage door (2022), water heater (2022), and water softener tank (2024) Exterior Water Line (2025). along with fresh exterior paint. Situated just steps from Sheffield Park, residents enjoy access to hiking and running trails, tennis and basketball courts, a playground, and a covered pavilion for events. Conveniently close to shopping centers, restaurants, downtown Tampa, the international airport, Clearwater beaches, and St. Pete, this neighborhood offers a peaceful environment with NO HOA fees. This turnkey home combines modern comfort with an unbeatable location—great curb appeal, stop by and take a look you wont be disappointed! MOTIVATED SELLER! SUBMIT YOUR OFFER TODAY!

1909 Castle Bay Court, Oldsmar

$399,000

3 Beds ⋅ 2 Baths ⋅ Heatherwood Unit One Condo SubDv.

Beautifully updated condo in East Lake Woodlands with 3 bedrooms, 2 full baths, 1 car garage and an added BONUS space/office! Right as you enter, notice the entire entryway is newly UPDATED with a custom door, paint, sconce lighting and Stanton carpet up the stairwell. Prepared to be wowed in the living room by the elegant, NEW custom built entertainment center with an electric fireplace. Set your color of choice and it can heat up the room for chilly nights. With the natural light from the 3 skylights, luxury vinyl plank flooring, vaulted ceilings, 2 huge fans on remotes.. this is quite the spot for entertaining. Kitchen features newer leathered granite countertops, wood cabinetry with soft close doors, stainless steel appliances, breakfast bar and new custom drapes. Step outside to the fully screened lanai with adjustable sunshades. Cool off with a new variable speed fan while enjoying all the wildlife East Lake Woodlands as to offer. The owner's suite also has a sliding door to the lanai, 2 closets with ample space, double bathroom vanities, countertops, garden tub and floor-to-ceiling tiled, glass-enclosed shower. Two other bedrooms with large windows share an updated bathroom. Enjoy an upstairs inside laundry with storage space and a bonus room with a convenient wet bar area. This space can be a TV room, office, playroom, sitting room for morning coffee..the ideas are endless. Additional updates include NEW water heater, new epoxy garage floor, remote blinds, water softener and light fixtures. HOA fee includes internet, cable, water, sewer, trash, community pool, exterior maintenance, grounds and insurance. Furniture is also available for purchase. East Lake Woodlands is central to Florida's most famous beaches, shopping, Tampa airport, A-rated schools and numerous dining options. There also is an option to join the Ardea Country Club and have access to 2 championship golf courses, tennis courts, fitness center, clubhouse, dining, swimming pools and social events. Don't miss this opportunity!

208 Clays Trail Unit 208, Oldsmar

$365,000

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

Set on nearly one-third of an acre with NO HOA restrictions, the property offers ample space to enjoy, expand, or customize.. Recent additional updates include a durable metal roof, hurricane-rated windows, and elevated entryways. Inside, the home features an open layout that connects the living, dining, and kitchen areas, creating a comfortable flow for everyday living and entertaining. The private in-law suite has its own entrance, giving the home added versatility for multi-generational living, guests, work-from-home needs, or income-producing possibilities. Seller reports no known flooding of the home. The .3 acre fully fenced backyard is spacious and inviting, with mature landscaping, fruit trees, and a paved patio area ready for an outdoor kitchen, a fire pit or an Accessory Dwelling Unit. A custom-built shed/workshop adds even more usable space for storage, tools, hobbies, or a creative studio.

3087 Duane Avenue, Oldsmar

$399,900

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Patio Homes SubDv.

Welcome to 360 S Woodlands Drive, a beautifully renovated 2-bedroom, 2-bath patio home nestled within the prestigious gated community of East Lake Woodlands in Oldsmar. Offering 24-hour guarded security and a maintenance-free lifestyle, this move-in ready residence combines modern upgrades with exceptional privacy and comfort. NEW ROOF + FLAT ROOF (2025)! NEW AC (2025)! Extensively updated throughout, the home features luxury vinyl plank flooring installed in 2022, a completely remodeled kitchen with granite countertops, premium cabinetry, and stainless steel appliances, along with two beautifully renovated bathrooms featuring updated tilework, granite countertops, and stylish vanities. The spacious primary suite serves as a private retreat with a custom-designed closet and an oversized soaking tub perfect for relaxation. Additional improvements include IMPAC impact windows, a new flat roof installed in December 2021, updated interior doors, and a custom 45-foot paver walkway that extends from the front entrance to the private rear patio, creating an ideal outdoor space for entertaining or enjoying Florida's beautiful weather. The HVAC system was replaced in 2025 for added peace of mind.The monthly HOA fee provides true maintenance-free living and includes lawn care, irrigation, Spectrum cable and internet service with two cable boxes, and exterior painting every five years. Residents also have the option to join East Lake Woodlands Country Club, offering two championship golf courses, tennis courts, swimming pools, fitness facilities, dining, and a vibrant social calendar. Ideally located near shopping, dining, parks, Tampa International Airport, and some of the area's most beautiful Gulf Coast beaches, this exceptional home offers the perfect blend of luxury, convenience, and Florida living. Schedule your private showing today.

360 S Woodlands Drive, Oldsmar

$375,000

3 Beds ⋅ 3 Baths ⋅ Bayside Terrace - Pt Rep SubDv.

NEW PRICE — Exceptional value in one of Oldsmar’s most desirable gated communities! Now offered at $375,000, this beautifully maintained 3-bedroom, 2.5-bath townhome in Bayside Terrace delivers modern, low-maintenance living just minutes from the waterfront charm of Safety Harbor. Built in 2019, the home features a bright, open-concept layout designed for both everyday living and entertaining. The spacious kitchen offers generous counter space and an oversized island that flows seamlessly into the dining and living areas. Upstairs, the primary suite features upgraded custom closets, while an additional bedroom includes a custom Murphy bed—perfect for creating a flexible guest room or home office. Thoughtful upgrades include luxury vinyl flooring, a whole-home water filtration and anti-scale system, and a 1-car garage with EV charger. Step outside to a peaceful patio setting, or enjoy the community’s resort-style pool overlooking Safety Harbor. With guest parking nearby and convenient access to Tampa, Clearwater, St. Petersburg, shopping, dining and recreation, this home offers an ideal combination of location, lifestyle and value at $375,000. Schedule your private showing today!

2013 Sunset Wind Loop, Oldsmar

$355,000

3 Beds ⋅ 2 Baths ⋅ Bayside Meadows Ph Ii SubDv.

One or more photo(s) has been virtually staged. Motivated seller!!! Tucked away on a cul-de-sac, this beautifully maintained single-family home offers comfort, space, and thoughtful upgrades perfect for modern family living. Featuring 3 spacious bedrooms and 2 full bathrooms which one has a jacuzzi, the home boasts an open-concept living and dining area filled with natural light—ideal for both relaxing and entertaining. In addition there are 4 hurricane impact windows; 3 energy efficient which come with covers. New roof just placed in June 2026. Warranty 50 years. HVAC/Water Heater 2024. The primary suite is a true retreat, complete with a walk-in closet and a uniquely designed master bathroom featuring a luxurious Jacuzzi tub, separate shower, and elegant double glass sinks. An additional room provides the perfect space for a home office, study, or flex use. Throughout the home, you’ll find a stylish combination of porcelain tile flooring in the main living areas and durable laminate flooring in the bedrooms, offering both beauty and easy maintenance. There is a swim spa in the backyard; a screen porch for relaxation; a shed and some gardening to work on. Also, house has an attached storage that could be turn into office. Also, in the garage there is an 38amp RV plug.

2009 Peppertree Court, Oldsmar

$399,000

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

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.

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

Homes for Sale in Oldsmar, FL Between $350,000 to $400,000

All Oldsmar, FL Homes for Sale Between $350,000 to $400,000

Joseph Sullivan Real Estate

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