Oldsmar Homes under $500,000

Oldsmar Homes under $500,000

Welcome to Oldsmar, Florida – a hidden gem nestled in the heart of Pinellas County! This vibrant city boasts a unique blend of small-town charm and modern amenities, making it the perfect place for families, retirees, and everyone in between. With its picturesque parks, beautiful waterfronts, and an abundance of recreational activities, Oldsmar offers a lifestyle that is both relaxing and invigorating.

Oldsmar is known for its friendly community spirit and a strong sense of belonging. Residents enjoy a variety of local events throughout the year, from farmers' markets to seasonal festivals that celebrate the city’s rich history. The city’s prime location provides easy access to the stunning beaches of the Gulf Coast, as well as the bustling urban life of nearby Tampa and St. Petersburg.

For those interested in making Oldsmar their home, the real estate market offers fantastic opportunities, particularly for homes under $500,000. Here, you’ll find a diverse selection of properties, from cozy single-family homes to charming townhouses, all designed to suit various lifestyles and budgets. Many homes in Oldsmar feature spacious yards, modern finishes, and proximity to excellent schools, parks, and shopping centers.

Whether you’re looking to settle down or make a savvy investment, Oldsmar’s real estate market is brimming with potential. Explore the available listings today and discover why so many are choosing to call this delightful city home. Embrace the Oldsmar lifestyle – where community meets convenience!

Newest Oldsmar Homes under $500,000

546 Trout Lane, Oldsmar
$449,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village Ph 2b SubDv. ⋅ 34677 Zip Code
55+ community. This is one of the most desirable single family homes in the Gull Aire sub. 2 Bedroom 2 bath with split plan separate Den (no closet). Beautiful open floor plan with gleaming hard wood floors in living and dining area. New hurricane ANDERSON WINDOWS installed in home last year (excluding enclosed porch). Bright and spacious home has an inside laundry, oversized 2 car garage with opener, whole house water purification system and so much more. The community has so much to offer like: Heated pool, lawn care, Bocci, Clubhouse and to many Monthly activities and social events to list Close to shopping, fine dining and everything your heart desires. Don't miss out on this rare opportunity!!!

546 Trout Lane, Oldsmar
1290 Clays Trail Unit 1403, Oldsmar
$469,000
3 Beds ⋅ 3 Baths ⋅ Laurel Oaks At East Lake SubDv. ⋅ 34677 Zip Code
Welcome to true maintenance-free living in the gated golf community of East Lake Woodlands. Simplify your life while still enjoying plenty of room with this move-in ready, spacious 2,700-sq. ft. townhome-style condominium offering 3 bedrooms, 2.5 baths, a versatile first-floor bonus area and sweeping golf course views. The bonus space offers exceptional flexibility and can be used as a home office, exercise room, playroom, media space or den. With high ceilings, crown molding and an inviting open-concept design, this home seamlessly connects the kitchen, dining area and family room creating an ideal setting for everyday living and entertaining. Inviting is the word to describe the well-appointed kitchen featuring wood cabinetry, gleaming granite countertops, expansive breakfast bar with plenty of seating and direct sightlines into the family room with recent updates including new lighting and Frigidaire Gallery refrigerator and Whirlpool microwave (2025). Other updates in 2025 include fresh interior paint, a new LG washer and dryer and new ceiling fans and light fixtures. The efficient 5-ton air-conditioning unit was replaced in 2025 as well providing added peace of mind. As a private retreat, the spacious primary suite affords gorgeous golf course views, wood floors, a large walk-in closet and an additional sitting area perfect for a den, reading nook or home office. The beautifully appointed primary bath features new cabinetry with tower storage, stunning quartz countertops, a freestanding soaking tub and gorgeous tile throughout. Two additional bedrooms provide generous room for family and guests and ample closet space. The secondary bathrooms feature updated cabinetry with quartz countertops in addition to an updated laundry room. Enjoy Florida living on the screened, covered patio, with an additional open area perfect for grilling, outdoor dining and entertaining while taking in the tranquil golf course backdrop. The maintenance-free lifestyle makes it easy to simplify and relax, with just two monthly bills to manage. With the 2025 A/C, electric bills for the owner have typically ranged from $130 to $230 during the summer, while the condo monthly maintenance fee covers comprehensive services including water and sewer, trash and recycling collection, lawn care and maintenance, exterior building maintenance including roof (installed 2020), termite prevention program, cable and internet services, insurance on building structure and escrow reserves. Plus residents also enjoy access to a sparkling community pool! Optional memberships are available for Ardea Country Club, offering access to 2 golf courses, fitness center, tennis and pickleball, a heated lap pool and freeform pool, poolside café, casual dining and a variety of social events and activities. Conveniently located near Tampa International Airport, top-rated schools, medical facilities, beaches and parks, professional sporting events and the many attractions of Tampa Bay, this East Lake Woodlands home delivers comfort, convenience and amenities all with golf course views. Move-in ready and maintenance free means more time to relax when at home or traveling!

1290 Clays Trail Unit 1403, Oldsmar
1801 Mapleleaf Boulevard, Oldsmar
$451,000
3 Beds ⋅ 3 Baths ⋅ Bays End SubDv. ⋅ 34677 Zip Code
Virtually Staged. Light-filled living spaces, a split bedroom plan, and a screened pool create an inviting setting in this four-bedroom, two-bath Oldsmar home with a two-car garage and inside laundry. The living room and dining area offer a separate setting for entertaining or quieter gatherings, while the kitchen and family room combine for everyday living. Large windows, arched architectural details, and beautiful flooring add character and warmth, with opportunities to update finishes and make the spaces your own. The kitchen features light cabinetry, stainless steel appliances, and a breakfast bar for casual meals or conversation with the cook. Its connection to the family room keeps the spaces open and social, while sliding glass doors lead to the screened pool area. The primary bedroom also offers sliding-door access to the pool, and its adjoining bathroom includes dual sinks, a separate tub, and a shower. An inside laundry room with overhead cabinetry adds practical storage. Outside, the pool and screen enclosure set the scene for relaxed afternoons, weekend gatherings, and a refreshing swim at the end of the day. Picture comfortable outdoor seating for morning coffee, a dining spot for casual meals, and your own touches of greenery to bring the space together. Beyond the enclosure, the fenced backyard offers possibilities for garden beds, flowering plants, or a landscaped sitting area. Whether you envision a quiet retreat or a setting for entertaining, the outdoor spaces offer an opportunity to create an extension of the home that reflects your style. Located near Tampa Road and the Curlew Road corridor, the property offers convenient access to shopping, grocery stores, restaurants, and everyday services throughout Oldsmar, nearby Palm Harbor, and the Countryside area. Connections to US 19, McMullen Booth Road, and Hillsborough Avenue provide routes throughout Pinellas County and into Tampa. Outdoor destinations Mobbly Bayou Wilderness Preserve, offering waterfront settings, trails, fishing, and kayaking, while John Chesnut Sr. Park and Philippe Park are each approximately five miles away. Local schools and St. Petersburg College provide nearby educational options. Tampa International Airport is approximately 14 miles away, and St. Pete–Clearwater International Airport is approximately 16.5 miles away. Come explore the layout, outdoor spaces, and possibilities this Oldsmar pool home has to offer. All distances are approximate and vary by route. Buyers to verify school zoning and enrollment availability directly with Pinellas County Schools. All information is believed to be accurate but is not guaranteed. Buyers and agents to verify all facts and information pertinent to their purchase decision.

1801 Mapleleaf Boulevard, Oldsmar
335 Country Club Drive, Oldsmar
$399,500
4 Beds ⋅ 2 Baths ⋅ Oldsmar Country Club Estates SubDv. ⋅ 34677 Zip Code
Welcome home to this beautifully updated 4-bedroom, 2-bath single-family home offering 1,224 square feet of comfortable living space on a spacious lot in a quiet, family-friendly neighborhood. Thoughtfully renovated with numerous upgrades completed in 2025, this home offers the convenience and peace of mind of newer major systems and finishes. Improvements include a new A/C system, water heater, electrical panel, impact-rated hurricane windows and doors, and all new appliances. Luxury vinyl plank flooring flows throughout the main living areas, complemented by new light fixtures and remote-controlled ceiling fans, creating a fresh and welcoming interior. An added neighborhood benefit is that the power lines have been buried underground, contributing to the clean streetscape and eliminating overhead utility lines. Step outside to enjoy the generously sized backyard, newly enclosed with attractive white vinyl fencing?perfect for entertaining, pets, play, or simply relaxing outdoors. The property also offers access to an easement leading to a canal, providing water access suitable for a small boat. For those who enjoy Florida's outdoor lifestyle, the community also features a neighborhood park and two boat launch areas. Centrally located near Mease Morton Plant Hospital, shopping, restaurants, and everyday conveniences, this home combines an established neighborhood.

335 Country Club Drive, Oldsmar
392 Cobia Way, Oldsmar
$178,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Welcome home to your Florida Retreat in Oldsmar! Discover the perfect blend of comfort, convenience and coastal charm in this beautifully maintained, move-in ready, furnished 2-bedroom, 2-bathroom, nestled in the heart of Oldsmar, Florida! Featuring a relaxed coastal vibe, this inviting home offers updated kitchen cabinets, bathroom vanities and showers, laminate flooring throughout, built-in cabinetry in the kitchen and dining areas, and an open-concept layout. The spacious living room and dining areas, complemented by plantation shutters, provide a welcoming setting for entertaining guests or simply relaxing in comfort. The generously sized primary suite features an updated en-suite bathroom, a spacious walk-in closet and a walk-in shower. Additional improvements include double-pane windows throughout, a newer central air conditioning system, water heater and a leaf guard system, backed by a lifetime warranty. 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.)

392 Cobia Way, Oldsmar
145 Poole Place, Oldsmar
$235,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cluster Homes SubDv. ⋅ 34677 Zip Code
Discover the ease of Florida living in this inviting 2-bedroom, 2-bath villa nestled within the gated golf community of East Lake Woodlands in Oldsmar. Offering a comfortable layout, a peaceful setting, and a low-maintenance lifestyle, this home is an excellent opportunity for a full-time residence, seasonal retreat, or anyone looking to enjoy all that the Tampa Bay area has to offer. Inside, the functional floor plan offers comfortable living and dining spaces, with a well-appointed layout designed for both everyday living and entertaining. The two-bedroom, two-bath configuration provides flexibility for guests, a home office, or a dedicated hobby space. Step outside to enjoy your own outdoor space, perfect for a quiet morning coffee or relaxing at the end of the day. Covered parking, additional storage, and convenient guest parking add to the home's everyday appeal. One of the standout advantages of living in Cluster Homes is the maintenance-free lifestyle, with exterior maintenance, grounds care, trash service, and basic cable included. The beautifully landscaped, gated East Lake Woodlands community is known for its natural surroundings and bird sanctuary setting, with sidewalks and walking and biking paths that invite you to slow down and enjoy the scenery. Residents also have the option to join Ardea Country Club, offering two golf courses, swimming pools, tennis courts, an exercise room, and on-site dining through available social and golf memberships. The location makes enjoying Florida's outdoor lifestyle easy, with John Chestnut Park, Oldsmar Park, and Philippe Park in nearby Safety Harbor. When you're ready for a beach day, Caladesi Island State Park and Clearwater Beach are just a drive away. Shopping, restaurants, entertainment, and everyday conveniences are close at hand, while Tampa International Airport and St. Pete-Clearwater International Airport offer convenient options for travel. Enjoy the combination of gated-community living, recreational opportunities, and convenient access to the best of Tampa Bay. Schedule your private showing and discover the lifestyle East Lake Woodlands has to offer!

145 Poole Place, Oldsmar
112 Cypress Court Unit 112, Oldsmar
$149,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code
MOTIVATED SELLER! This 2-bedroom, 2-bath condo in the golf course community of East Lake Woodlands is ready for its next owner. Brand-new LVP flooring was installed in 2026, and a fresh coat of paint is being finished now, so the unit shows bright, clean, and move-in minded. Low-maintenance condo living means more time to enjoy the community, which offers a golf course and a clubhouse right where you live. Location is a big part of the value here. US-19 is minutes away, with quick access to shopping, dining, and the rest of the Tampa Bay area. First-time buyer, downsizer, seasonal resident, or investor, this one fits a lot of plans. The seller is motivated and the price reflects it. Schedule your showing today.

112 Cypress Court Unit 112, Oldsmar
131 Woodlake Wynde, Oldsmar
$159,500
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Woodlake Run SubDv. ⋅ 34677 Zip Code
AMAZING POTENTIAL in East Lake Woodlands, NON-Flood Zone and your Cable, Internet & Water is included in the HOA! This accessible first-floor condo is a fantastic opportunity to create your forever dream space. Located directly across from the heated community pool, this condo bursts with potential and is located in a highly desirable central location within the East Lake Woodlands community. Enjoy both your screened-in front and back patios, providing two comfortable outdoor spaces to relax and enjoy nature without the bugs! Inside, you’ll find tile flooring throughout, a spacious living room and dining room combo with a wet bar, and an open kitchen with plenty of extra counter seating. The washer and dryer are conveniently located right outside the kitchen in the front patio laundry closet, and being on the first floor means easy access with no stairs to navigate. This guard-gated community offers a peaceful setting surrounded by mature landscaping and wildlife, and if you decide to join the Ardea club, the main clubhouse, golf course, and tennis courts are right across the street. The HOA fee includes: Cable TV, Internet, Water, Community Pool, Escrow reserves, Maintenance Exterior, Roof, Grounds Maintenance, Security and Trash. East Lake Woodlands is home to the Adrea Country Club offering a variety of optional memberships for homeowners to join. These exclusive amenities include Two Championship 18-hole Golf Courses, Tennis and Pickleball Courts, Clubhouse Bar, Casual and Fine Dining, Fitness Center, Splash Pad, Swimming Pools, Clubhouse Events and more. Centrally located near top-rated schools, trending restaurants, shopping, movies, parks, Tarpon Lake, Gulf Coast beaches, local hospitals, Tampa Airport and more, you’ll never run out of activities in town!

131 Woodlake Wynde, Oldsmar
1704 Hibiscus Circle S, Oldsmar
$425,000
3 Beds ⋅ 2 Baths ⋅ Harbor Palms-Unit Six SubDv. ⋅ 34677 Zip Code
Welcome to this beautifully remodeled 3-bedroom, 2-bathroom home in Oldsmar, offering a desirable split-bedroom floor plan, modern finishes, and exceptional Florida indoor-outdoor living. Featuring a brand-new roof installed in 2026, hurricane impact windows and doors, tile flooring throughout, and a fully remodeled interior, this home is truly move-in ready. The stunning kitchen features quartz countertops, brand-new cabinetry, stainless steel appliances, and a spacious island with bar seating, creating the perfect spot for casual meals, morning coffee, or entertaining guests. The kitchen seamlessly flows into the spacious family room, surrounded by sliders and windows overlooking the sparkling pool, bringing in an abundance of natural light and creating a beautiful connection between the indoor and outdoor living spaces. The home offers two separate living areas, including a welcoming main living room and a secondary family room, providing plenty of flexibility for entertaining, relaxing, or everyday living. Both bathrooms have been completely remodeled, including the spacious primary suite with a double vanity and walk-in closet. Step outside to your private backyard oasis featuring a freshly resurfaced swimming pool, new pavers, a newly screened pool enclosure, and a brand-new aluminum fence surrounding the property. The pool area also offers convenient direct access to a bathroom, making pool days and entertaining effortless. The freshly remodeled garage adds even more functionality, while a backyard storage shed provides additional space for tools, equipment, and outdoor essentials. With no HOA, you have the freedom and flexibility to enjoy the property your way. Conveniently located in Oldsmar with easy access to Tampa International Airport, Gulf Coast beaches, shopping, dining, parks, and major roadways, this home combines modern upgrades, privacy, and the Florida lifestyle in one exceptional package. Zoned for Oldsmar Elementary, Carwise Middle, and East Lake High School, this is a fantastic opportunity to own a completely updated home in a highly convenient Oldsmar location.

1704 Hibiscus Circle S, Oldsmar
127 Nancy Drive Unit 127, Oldsmar
$205,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Move-In Ready, Renovated First-Floor Condo in East Lake Woodlands! Relax & enjoy effortless Florida living w/ the much-coveted combination of a FIRST-FLOOR, MOVE-IN READY, MAINTENANCE-FREE 2-bedroom, 2-bath condo in the desirable gated golf community of East Lake Woodlands! This beautifully updated home has all the bells & whistles, including granite countertops, shaker-style cabinetry, tiled backsplash, LED lighting, tile & luxury laminate flooring throughout, Maytag washer & dryer, & an inlaid travertine-tiled patio floor. You'll like the peace of mind of a newer HVAC System & water heater (both '21). Be "wowed" w/ the peaceful & tranquil conservation & wooded views from the rear of the home! The excellent floorplan provides an open feel w/ abundant natural light & rear sliders leading to your private covered patio w/ additional storage—a perfect spot to relax & enjoy the natural surroundings. The desirable two-way split-bedroom plan offers both privacy & functionality. The spacious primary suite features an impressive three walk-in closets—one large & two additional closets—along w/ a private bath suite. Both bedrooms feature luxury laminate flooring w/ NO CARPET. Ground-floor living makes everyday access easy, & covered parking adds another level of convenience. Even better, the community swimming pool & clubhouse are located directly across the street, making it easy to enjoy the Florida lifestyle just steps from home. This Condo is NOT in a flood zone (Zone X). For those seeking additional resort & country club amenities, Ardea Country Club offers optional private memberships for addl. fees, incl. access to two 18-hole championship golf courses, tennis & pickleball, fitness center & classes, heated lap & free-form pools, dining, & social events. Membership is separate from the community. East Lake Woodlands offers a premier Oldsmar location convenient to shopping, restaurants, parks, medical facilities, A-rated schools, Tampa International Airport, award-winning Gulf beaches, & the many professional sporting events, concerts & entertainment destinations throughout the Tampa Bay area. Whether you're looking for a full-time residence, seasonal Florida retreat, or investment opportunity, this renovated first-floor condo combines comfort, convenience, peaceful, wooded views & the gated-community lifestyle that makes East Lake Woodlands such a desirable place to call home!

127 Nancy Drive Unit 127, Oldsmar
110 Lakeside Court Unit 110, Oldsmar
$149,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Virtually Staged. Welcome to effortless Florida living in this beautifully updated 2-bedroom, 2-bathroom second-floor condo, ideally situated within the gated community of East Lake Woodlands. Offering a spacious great-room floor plan and a recently remodeled interior, this charming residence combines comfort, convenience, and a relaxed resort-style lifestyle. The inviting kitchen has been upgraded with tile countertops and a contemporary backsplash, creating a stylish and functional space for everyday living and entertaining. The main living areas and bedrooms feature comfortable carpeting, while both bathrooms offer neutral finishes and appointments, providing a versatile backdrop for your personal decorating style. The generously sized primary bedroom offers an abundance of space and features two walk-in closets for exceptional storage. Sliding glass doors provide easy access to the private screened-in porch, where you can unwind with your morning coffee or enjoy a peaceful evening while taking in relaxing views of the expansive green space. The porch also provides convenient access to the laundry closet. Recent improvements include a new hot water heater installed in 2026, offering added peace of mind for the new owner. The condo also includes covered carport parking conveniently located next to the mailbox, making everyday living even more convenient. Residents of this quiet, well-maintained gated community have access to a beautiful community pool, providing the perfect setting for cooling off, relaxing, or entertaining guests. For those seeking an even more elevated country-club lifestyle, residents have the option to join Ardea Country Club for an additional fee. Membership opportunities include access to an impressive array of amenities, including: Two championship 18-hole golf courses, Pickleball and tennis courts, Olympic-style lap pool, Fitness center, On-site restaurant A variety of social activities and events Beyond the community, the location offers exceptional convenience. Enjoy easy access to airports, medical facilities, shopping, restaurants, beautiful Gulf beaches, and a wide variety of entertainment and recreation, all just a short drive away. Whether you're looking for a full-time residence, a seasonal retreat, or a low-maintenance Florida getaway, this lovely East Lake Woodlands condo offers comfort, convenience, and carefree living in a peaceful country-club setting.

110 Lakeside Court Unit 110, Oldsmar
151 Lakeview Way Unit 151, Oldsmar
$189,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Virtually Staged. WATERFRONT, GROUND FLOOR, UPDATED and MOVE-IN READY! Enjoy one of the most peaceful, nature-filled views in the highly sought-after East Lake Woodlands community from this beautifully updated 2-bedroom, 2-bath condo with assigned COVERED PARKING. Step inside to a spacious, open layout with NO CARPET and plenty of natural light. The updated kitchen features NEW GRANITE COUNTERTOPS, NEW CABINETS, a pantry closet, generous storage, and a large breakfast bar overlooking the dining and living areas. The inviting living room features a cozy WOOD-BURNING FIREPLACE, perfect for those occasional cool Florida evenings. Sliding glass doors from BOTH the living room and primary suite open to the tiled lanai, creating a wonderful extension of the living space and the perfect place to enjoy your morning coffee while taking in the tranquil WATERFRONT VIEW and surrounding wildlife. The spacious primary suite features QUARTZ COUNTERTOPS, WALK-IN SHOWER, and a stylish NEW BARN DOOR. The guest bathroom includes a newer vanity, and both bathrooms feature NEW ELONGATED CHAIR-HEIGHT TOILETS installed in 2023. You'll also appreciate the abundance of closet and storage space throughout the home. Additional updates include a NEW A/C IN 2023, NEW BLINDS IN 2023, NEW CEILING FANS, laminate flooring in both bedrooms, and ceramic tile throughout the remainder of the condo, including the lanai. Assigned covered parking is included, along with plenty of additional guest parking. The community HEATED POOL is just a short walk away for year-round enjoyment. East Lake Woodlands offers a beautiful, gated country club setting surrounded by mature landscaping, lakes, and natural Florida scenery. Optional club memberships provide access to additional amenities that may include golf, tennis, fitness, dining, pools, and clubhouse facilities. Conveniently located near shopping, restaurants, parks, beaches, and Tampa International Airport. GROUND FLOOR + WATERFRONT VIEW + UPDATED INTERIOR + COVERED PARKING + NO CARPET = Florida living made easy!

151 Lakeview Way Unit 151, Oldsmar
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