Oldsmar Homes under $500,000

Oldsmar Homes under $500,000

Welcome to Oldsmar, Florida, a hidden gem nestled in the heart of Pinellas County. Known for its charming small-town feel and vibrant community spirit, Oldsmar offers a unique blend of suburban tranquility and easy access to the bustling activities of the Tampa Bay area. With stunning parks, scenic waterfront views, and a variety of dining and shopping options, this city is perfect for families, retirees, and young professionals alike.

Oldsmar is renowned for its beautiful outdoor spaces, including the picturesque Oldsmar City Park and the serene waterfront along the Old Tampa Bay. Residents can enjoy a plethora of recreational activities, from boating and fishing to hiking and biking along scenic trails. The city's commitment to community events fosters a welcoming atmosphere, making it easy to connect with neighbors and friends.

For those seeking a home in this idyllic city, Oldsmar offers an impressive selection of properties priced under $500,000. Whether you're looking for a cozy single-family home, a modern townhouse, or a charming condo, you'll find a variety of options that cater to different lifestyles and budgets. These homes often feature spacious layouts, updated amenities, and beautiful outdoor spaces, perfect for enjoying the Florida sunshine.

With its prime location, friendly community, and affordable housing options, Oldsmar is the perfect place to call home. Discover the charm of Oldsmar and explore the wonderful homes waiting for you in this delightful city!

Newest Oldsmar Homes under $500,000

300 State Street E Unit 326, Oldsmar

300 State Street E Unit 326, Oldsmar

2 Beds ⋅ 3 Baths ⋅ Oldsmar Galleria SubDv. ⋅ 34677 Zip Code

Virtually Staged. Discover elevated living in the heart of Oldsmar! Welcome to this spacious, move-in-ready PENTHOUSE condo at Oldsmar Galleria, offering 1,553 square feet of living space, 2 bedrooms, 2.5 bathrooms, and a distinctive two-level floor plan. One of the largest floor plans in the building, this residence stands out with its impressive HIGH CEILINGS, abundant natural light, and bright, open living spaces that create an inviting sense of comfort and openness. The main living level features a spacious open-concept layout, ideal for everyday living and entertaining. The kitchen is equipped with stainless steel appliances, generous cabinet space, and a convenient breakfast bar. Upstairs, both bedrooms offer the privacy of their own ensuite bathrooms, providing a comfortable and functional arrangement. Additional highlights include a NEW A/C SYSTEM (2026), in-unit laundry, one assigned parking space, and convenient elevator access to the third floor. LOCATION IS EVERYTHING! Situated in the heart of Oldsmar, this condo places you within a short distance of local coffee shops and restaurants, with convenient access to shopping, parks, Tampa, Clearwater, and the beautiful Gulf Coast beaches. Enjoy the convenience of a central Tampa Bay location while embracing a low-maintenance Florida lifestyle.

300 State Street E Unit 326, Oldsmar

1609 Vineyard Lane, Oldsmar

1609 Vineyard Lane, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Tuscany Woods Preserve SubDv. ⋅ 34677 Zip Code

Virtually Staged. Welcome to this inviting two-story townhome featuring 3 bedrooms, 2 full bathrooms, 1 half bathroom, and 1,525 square feet of living space! Built in 2017, this home offers a functional floor plan with comfortable living areas perfect for everyday living and entertaining. The spacious layout provides plenty of flexibility, while the attached 1-car garage offers convenient parking and additional storage space. Enjoy the benefits of townhome living with a low-maintenance lot and plenty of potential to make this space your own. Whether you're looking for your next home or an investment opportunity, this property has plenty to offer. Schedule your showing today! One or more photos have been virtually staged.

1609 Vineyard Lane, Oldsmar

559 Dove Terrace S, Oldsmar

559 Dove Terrace S, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village Ph 2c SubDv. ⋅ 34677 Zip Code

Virtually Staged. Enjoy TRANQUIL POND AND CONSERVATION VIEWS from this beautifully remodeled home! An OPEN FLOOR PLAN with VAULTED CEILINGS frames unobstructed views of nature from most rooms, while PLANTATION SHUTTERS throughout add a classic touch. The cedar-lined FLORIDA ROOM, complete with shades and an awning, is the perfect spot for morning coffee or unwinding at sunset. Recent updates include 42-INCH ALL-WOOD CABINETS, GRANITE counters, and STAINLESS STEEL APPLIANCES, plus newer LAMINATE FLOORING throughout. Major systems are already done for you: roof replaced in 2019, primary bath and laundry renovated in 2021, HURRICANE WINDOWS installed in 2023, A/C in 2018, and hurricane straps on the garage door. The water is purified with a reverse osmosis system provided by the county. Some furnishings available separately. Life in GULL AIRE VILLAGE, an active 55+ community, centers on the heated pool, spa, clubhouse, library, shuffleboard, bocce, and pool table, with golf-cart-friendly streets and a paved walking path along the Tarpon outflow canal connecting to the Oldsmar Trail. Shopping, restaurants, the AMC theater, Bealls, Marshalls, and Richards Foodporium are all within walking distance, and Westfield Countryside Mall, Publix, Walmart, and Countryside Hospital are just minutes away. On weekends, the Gulf beaches await. Honeymoon Island and Caladesi Island State Park are an easy drive, with both airports close by. Peaceful water views, a turnkey list of updates, and a welcoming 55+ community: your relaxed Florida lifestyle starts here!

559 Dove Terrace S, Oldsmar

238 Pelican Drive N, Oldsmar

238 Pelican Drive N, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code

Virtually Staged. Discover the perfect blend of comfort, convenience and coastal charm in this beautifully maintained, move-in ready, 2-bedroom, 2-bathroom, nestled in the heart of Oldsmar, Florida! Featuring a relaxed coastal vibe, this inviting home offers spacious living, dining and kitchen areas, newer stainless-steel appliances, updated bathroom vanities, beautiful laminate flooring, updated subflooring throughout, fresh paint throughout, a newer vapor barrier, and an open-concept layout. The generously sized primary suite features a spacious walk-in closet, an en-suite bathroom, with a separate garden-like tub, a separate water closet with walk-in shower creating a comfortable space to unwind. Located in the highly desirable 55+ community of Gull-Aire Village, this golf cart-friendly neighborhood offers an exceptional lifestyle with resort-style amenities including a spacious clubhouse, large, heated pool and spa, library, enclosed shuffleboard court, bocce ball court, and an active calendar of social events and activities. Enjoy the added advantage of owning the land with an affordable monthly HOA fee of just $70. One pet of any size is welcomed and two boat and RV storage areas are available for a low monthly rental fee. You’ll love the unbeatable location is less than a mile from Woodlands Square and just minutes to everyday conveniences. Honeymoon Island Beach is approximately 9 miles away, Mease Countryside Hospital among other health facilities are approximately 2 miles away, St.Pete/Clearwater Int'l Airport is a quick 11-miles away and Tampa Int'l Airport is only a 15-mile drive. For those of you who enjoy the outdoors, the adjacent walking, running, and biking trail along Canal Way leads directly to picturesque Sheffield Park, offering another wonderful way to embrace Florida’s outdoor lifestyle. Whether you’re socializing at the clubhouse, relaxing by the sparkling pool, or simply soaking in the tranquil pond views, you’ll appreciate the welcoming atmosphere and vibrant lifestyle that make Gull-Aire Village such a special place to call home. Don’t miss this opportunity to enjoy affordable Florida living in a desirable, amenity-rich community. Schedule your private tour today! (Room dimensions are approximate and should be verified by the Buyer.)

238 Pelican Drive N, Oldsmar

608 Timber Bay Circle E, Oldsmar

608 Timber Bay Circle E, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Shoreview Ph I SubDv. ⋅ 34677 Zip Code

Welcome home to this beautifully maintained and thoughtfully updated 3-bedroom, 2-bath residence in the heart of Oldsmar! Offering the perfect blend of comfort, character, and peace of mind, this home is ready for its next owners to move right in and start enjoying the Florida lifestyle. With NO HOA fees, this property offers added peace of mind along with valuable updates throughout. The roof was replaced in 2020 and features hurricane straps, while additional improvements include select insulated windows, an impact-resistant bathroom window and patio doors (2019), an insulated impact garage door, and a new electrical panel in 2023. Beautiful oak hardwood flooring, installed in 2022 with sound-reducing underlayment, adds warmth and timeless appeal throughout the home. The kitchen is full of character, featuring gorgeous Silestone Copper Mist waterfall countertops, slate tile flooring, and a newer sink. Both bathrooms have also been tastefully updated with modern finishes, creating a comfortable, refreshed feel throughout. One of the home's standout features is the air-conditioned ented garage, offering wonderful flexibility for extra storage, a workshop, hobbies, or a space to make your own. Step outside and enjoy your morning coffee on the front porch, relax in the screened lanai, or unwind in your own private backyard retreat. Need room for your toys? The additional front parking pad is ideal for a boat, golf cart, or RV! Located in a golf cart-friendly community, you'll love being just minutes from local parks, boat ramps, kayak launches, and Oldsmar's popular community events. Tampa International Airport is approximately 12 miles away, making travel convenient while allowing you to enjoy the comfort and charm of your own neighborhood. No HOA fees, meaningful upgrades, inviting outdoor spaces, and a location that makes enjoying Florida easy! This home truly deserves a closer look! The sellers are motivated and ready to make a deal, creating an excellent opportunity for the next fortunate homeowner to make this special property their own. Come see all that Oldsmar has to offer. You may just find the home you've been waiting for!

608 Timber Bay Circle E, Oldsmar

105 Palmetto Court, Oldsmar

105 Palmetto Court, Oldsmar

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code

Just what you have been waiting for....! FIRST floor, pet friendly (up to 40 pounds), condo located in Cypress Estates III of the popular gated community of East Lake Woodlands Country Club, a community that has been designed to enhance your lifestyle. Direct entrance takes you to open views of the dining and living room area out thru the sliding doors to your screened lanai overlooking a park like setting view. This home has been carefully maintained and has a split bedroom plan and the primary bedroom offers two closets, ensuite bath with updated sink vanity and newer tiled shower in the primary bath. Spacious guest bedroom with wall closet. The laundry closet is located off your lanai with washer/dryer. There is a community pool just down from the condo, one covered parking space and other available guest spaces. Optionally, you could join the Ardea (formerly the East Lake Woodlands) Country Club for use of their facilities that will include Clubhouse, two Championship 18 hole golf courses, additional heated pools, tennis courts, fitness center and Clubhouse restaurants and social gatherings. Minutes away from Countryside Mall and the sandy beaches of Honeymoon Island along with parks, restaurants and entertainment. This is a gated, golf cart friendly community (must be street legal), which is handy to run over to the nearby shopping plaza for some of your everyday needs. Location is everything! It is approximately 15 miles from Tampa Airport and less than 10 miles to the beach. For more information about the community and the area go to the East Lake Woodlands website.

105 Palmetto Court, Oldsmar

261 Woodlake Wynde Unit 261, Oldsmar

261 Woodlake Wynde Unit 261, Oldsmar

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Woodlake Run SubDv. ⋅ 34677 Zip Code

This beautifully updated home features a modern kitchen, a convenient wet bar perfect for entertaining, and access to an abundance of community amenities. Enjoy a blend of comfort, style, and convenience, with opportunities for relaxation and recreation. Whether entertaining guests or enjoying a quiet evening at home, this home provides a welcoming setting for everyday living. Schedule your private showing today!

261 Woodlake Wynde Unit 261, Oldsmar

1703 Ironwood Court E, Oldsmar

1703 Ironwood Court E, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Harbor Palms-Unit Six SubDv. ⋅ 34677 Zip Code

Welcome to 1703 Ironwood Court E, a beautifully renovated single-story home located in the desirable Harbor Palms community of Oldsmar! Offering 2 spacious bedrooms, 2 full bathrooms, 1,064 square feet of living space, and an attached one-car garage, this move-in-ready property combines modern updates, comfort, and an excellent location. Step inside and discover a bright, inviting interior featuring beautiful tile flooring, elegant crown molding, updated finishes, and an open, functional layout designed for everyday living and entertaining. The stylish living area offers abundant natural light, while the thoughtfully updated kitchen features modern cabinetry, contemporary finishes, and convenient access to the main living spaces. Both bathrooms feature attractive modern finishes, creating a fresh, comfortable atmosphere throughout the home. The bedrooms offer plenty of versatility for a primary retreat, guest accommodation, or home office. MAJOR HOME FEATURES INCLUDE A DURABLE TILE ROOF, CENTRAL AIR CONDITIONING, AND DOCUMENTED HVAC AND INTERIOR RENOVATION WORK COMPLETED IN 2025. Additional improvements include updated flooring, interior finishes, and other renovations that add to the home's appeal. Situated on an approximately 6,000-square-foot lot, the property offers generous outdoor space with a private backyard, an outdoor patio area, and room to relax, entertain, or create your ideal Florida outdoor retreat. NO HOA AND NO CDD FEES! Enjoy the flexibility of homeownership without mandatory association fees. Conveniently located near beautiful parks, shopping, restaurants, schools, and major roadways, with easy access to Tampa, Clearwater, Safety Harbor, and the stunning Gulf Coast beaches. Whether you're searching for your primary residence, a comfortable Florida retreat, or an investment opportunity, this renovated Oldsmar home has so much to offer. Schedule your private showing today and discover everything this wonderful property has to offer!

1703 Ironwood Court E, Oldsmar

127 Camphor Drive Unit E, Oldsmar

127 Camphor Drive Unit E, Oldsmar

2 Beds ⋅ 2 Baths ⋅ SubDv. ⋅ 34677 Zip Code

Welcome to The Gardens of Forest Lakes! This spacious FIRST-FLOOR, 2-BEDROOM, 2-BATH CONDO offers comfortable, low-maintenance Florida living with no stairs, TILE FLOORING THROUGHOUT and BEAUTIFUL POND VIEWS! Nestled in a peaceful setting surrounded by mature landscaping and lush greenery, this light and bright residence offers a wonderful combination of comfort, convenience and scenic surroundings. Step inside to a living and dining area with plenty of space to relax or entertain. Sliding glass doors lead to a covered patio overlooking the tranquil pond, creating the perfect spot to enjoy your morning coffee, watch the wildlife or simply unwind while taking in the peaceful water views. The kitchen offers ample cabinetry, generous counter space and a convenient breakfast/pass-through bar that opens to the main living area. The primary bedroom features a private ensuite bathroom and walk-in closet, while the second bedroom provides flexibility for guests, a home office or additional living space & adjacent guest bath. An interior laundry area adds everyday convenience. With tile flooring throughout and a functional floor plan, this condo provides a great opportunity to add your own personal touches while enjoying its desirable first-floor location and picturesque setting. Beyond the condo, residents can enjoy an impressive array of community amenities in a scenic lakefront setting. Forest Lakes offers a large community swimming pool and spa, tennis courts, basketball, racquetball/handball courts, playground, picnic and grilling areas, and a waterfront dock overlooking the lake. Mature trees, tropical landscaping and generous green spaces create an inviting atmosphere throughout the community. Conveniently located in the heart of Oldsmar, close to shopping, dining, parks, beautiful Gulf beaches and Tampa International Airport. Whether you're searching for a primary residence, seasonal getaway or investment opportunity, this first-floor condo with beautiful pond views offers an excellent opportunity to enjoy the Florida lifestyle. Schedule your private showing today!

127 Camphor Drive Unit E, Oldsmar

116 Brent Circle, Oldsmar

116 Brent Circle, Oldsmar

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

Welcome to Seaside Estates! This is a 3 bedroom, 3 bathroom townhome on the canal with your own private dock. If you’ve been looking for a place to keep your jet ski or kayak right outside your door, this is it. The entry level gives you direct access to the garage, where sliders on the back open right out to the docks. Load up your gear and be on the water in minutes. The second floor features a large living room that opens onto a balcony overlooking the canal. This level also includes the kitchen, a full bathroom, and a bedroom, a great setup for guests or a home office. Head up to the third floor to find two more bedrooms, each with its own ensuite bathroom. The owner’s suite has a private balcony with views of the canal, the perfect spot for morning coffee or evening sunsets. Laundry is conveniently located on this level, right where you need it. This home is ready for a new owner to make it their own. With some fresh paint, new carpet, and your personal touches, you can build equity and create the waterfront retreat you’ve been dreaming of. Opportunities with private dock access like this don’t come along often. Call today to schedule your showing!

116 Brent Circle, Oldsmar

129 Caryl Way Unit 129, Oldsmar

129 Caryl Way Unit 129, Oldsmar

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code

Short Sale. UNAPPROVED SHORT SALE – Renovation Opportunity in Highly Desirable East Lake Woodlands! Bring your vision and transform this 2-bedroom, 2-bathroom condo into your ideal Florida retreat! Located within the highly sought-after, guard-gated community of East Lake Woodlands in Oldsmar, this property presents an excellent opportunity for buyers looking to renovate and make it their own. Whether you're searching for a primary residence, seasonal getaway, or investment opportunity, this condo offers plenty of potential. Enjoy the beautiful surroundings of this established community, conveniently located near shopping, dining, entertainment, beaches, and everything the Tampa Bay area has to offer. The HOA fee includes cable TV, high-speed internet, water, sewer, trash collection, exterior maintenance, grounds maintenance, community pool, and reserves, providing added convenience and value. Property is being sold as an unapproved short sale, subject to lender approval. Bring your creativity and take advantage of this opportunity to own in one of Oldsmar's most desirable communities!

129 Caryl Way Unit 129, Oldsmar

404 Lakeview Drive, Oldsmar

404 Lakeview Drive, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Manors Of Forest Lakes The SubDv. ⋅ 34677 Zip Code

Welcome to Forest Lakes, where beautiful lake views and a wonderful community setting come together! This beautiful completely renovated 3-bedroom, 2-bath home offers 1,550 square feet of inviting living space, a 2-car garage, and a generous lakefront lot spanning over a quarter acre. From the moment you step inside, you’ll appreciate the fresh, modern feel, gorgeous tile flooring throughout, and designer finishes that give the home a polished, cohesive look. The remodeled kitchen is sure to be a favorite gathering spot, featuring quartz countertops, brand-new stainless steel appliances, a spacious island with breakfast bar seating, and a pantry for added storage. Whether preparing a meal or entertaining friends, this thoughtfully designed space offers both style and functionality. New windows throughout the home bring in abundant natural light, creating a bright and welcoming atmosphere. The primary suite offers a relaxing retreat, complete with a private en-suite bathroom featuring a step-in shower. Sliding glass doors open directly from the bedroom to the backyard, where peaceful lake views provide a lovely backdrop to start your day or unwind in the evening. The second bathroom is equally inviting, with a vanity offering generous counter space, a bathtub, and elegant gold accents that add a touch of sophistication. Major improvements include a new roof, water heater and HVAC system, offering added peace of mind for the next owner. And the location is just as appealing! Situated only one house away from the community amenities, you’ll have easy access to the neighborhood swimming pool, fishing pier, tennis, basketball and handball courts, playground, and picnic areas—all for a low $35 monthly fee. Located in an exceptional school district, Forest Lakes is also convenient to shopping, dining, and entertainment in Oldsmar, with easy access to both sides of Tampa Bay. Tampa International Airport and St. Pete-Clearwater International Airport are also just a short drive away. With its stylish renovations, thoughtful details, sun-filled interiors, and beautiful lakefront setting, this home offers a wonderful opportunity to enjoy the best of Forest Lakes living. Schedule your showing today!

404 Lakeview Drive, Oldsmar

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