Oldsmar Homes under $750,000

Oldsmar Homes under $750,000

Welcome to Oldsmar, Florida – a hidden gem nestled in the heart of Pinellas County! This charming city boasts a unique blend of small-town warmth and modern amenities, making it an ideal place for families, retirees, and anyone looking to embrace the Florida lifestyle. With its lush parks, scenic waterfront, and vibrant community spirit, Oldsmar is not just a place to live; it’s a place to thrive.

Oldsmar is conveniently situated between the bustling cities of Tampa and Clearwater, offering residents easy access to a wealth of shopping, dining, and entertainment options. The city is known for its beautiful parks, such as the expansive Oldsmar Park and the picturesque waterfront along Old Tampa Bay, where residents can enjoy fishing, kayaking, or simply soaking in the stunning sunsets. The community also hosts a variety of events throughout the year, fostering a strong sense of belonging among its residents.

For those seeking a home in this delightful city, Oldsmar offers a fantastic selection of properties under $750,000. Whether you’re looking for a cozy single-family home, a spacious townhouse, or a charming villa, you’ll find an array of options that cater to your lifestyle and budget. Many of these homes feature modern amenities, beautiful landscaping, and are situated in family-friendly neighborhoods, making it easy to find the perfect fit for you.

Discover the warmth and charm of Oldsmar, where your dream home awaits amidst a vibrant community and stunning natural beauty!

Newest Oldsmar Homes under $750,000

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
1558 E Lake Woodlands Parkway, Oldsmar
$739,000
3 Beds ⋅ 2 Baths ⋅ Greenhaven Unit-Four SubDv. ⋅ 34677 Zip Code
Virtually Staged. Discover an updated, move-in ready home with stunning design and finishes that flow beautifully throughout - all set on a desirable corner lot within the gated golf community of East Lake Woodlands. Offering 3 bedrooms, 2 full bathrooms, a 3-car garage and a landscaped, fenced backyard, this inviting home combines comfortable everyday living with a convenient Tampa Bay location. Complemented by abundant natural light, high ceilings, crown molding and an open, welcoming layout, this residence features beautiful hardwood and engineered wood flooring throughout the living areas and bedrooms - so no carpet! The bright living room and dining room combination provides an elegant setting for entertaining with a signature arched window complete with plantation shutters and glass sliders leading to the outdoors. Open to the family room, the updated kitchen provides a seamless space for gatherings and daily living and features stainless steel appliances including double GE convection ovens, induction cooktop, Bosch dishwasher and an expanse of updated cabinetry with convenient pull-outs and Lazy Susan, Cambria quartz countertops, large breakfast bar and pantry storage. Glass sliders and a wood burning fireplace accent the family room and provide an inviting place to relax. With a split floor plan, the primary suite is designed for privacy and pampering, featuring 2 closets with custom built-in cabinetry installed in 2025, glass sliders overlooking the tranquil backyard and a luxurious primary bath with gorgeous tile, large tub and double vanity with granite countertops. The secondary bathroom has been updated with attractive tile finishes and granite countertops as well, providing a polished complement to the home’s interior. Improvements include a Generac home generator with a buried 500-gallon propane tank, a 2023 water heater, 2022 water softener and 2010 tile roof. These updates add practical value and enhance the home’s functionality and peace of mind as well as a location in Zone X, the lower probability flood zone which does not require flood insurance by lenders. Outside, the landscaped corner-lot setting offers a wide driveway for plenty of parking for family and guests, mature trees and a fenced backyard with privacy and room to create a relaxing outdoor retreat. The 3-car garage provides generous parking and additional storage while the home’s layout and surrounding greenery add to its everyday ambiance. East Lake Woodlands offers a gated golf-community setting near top-rated schools, medical facilities, shopping, airports, professional sporting events and the many attractions of the Tampa Bay area. Optional memberships to Ardea Country Club provide access to 2 golf courses, tennis and pickle ball, a fitness center, heated lap pool and free form pool with a poolside café, casual and fine dining and a host of social events and activities.

1558 E Lake Woodlands Parkway, 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
4795 Pebble Brook Drive, Oldsmar
$485,000
2 Beds ⋅ 2 Baths ⋅ Cross Creek - Unit Two SubDv. ⋅ 34677 Zip Code
Warm. Inviting. Bright. A truly move in ready home in the sought out gated community of East Lake Woodlands. This 2 bedroom 2 bath plus den, features granite counters, wood cabinets, plantation shutters, crown molding, inside laundry room, screened lanai, high ceilings formal dining area, dinette in kitchen. Furnishings negotiable. The community itself is gated and offers 2 18 hole golf courses, fitness center, tennis and pickleball courts.

4795 Pebble Brook Drive, Oldsmar
3090 Phoenix Avenue, Oldsmar
$689,000
3 Beds ⋅ 3 Baths ⋅ West Oldsmar Sec 1 SubDv. ⋅ 34677 Zip Code
Imagine waking up to sparkling water views and having the ultimate Tampa Bay lifestyle right in your backyard. Situated in one of the area’s most desirable coastal pockets, this waterfront property offers direct boat access, giving you the freedom to set sail from your private dock and cruise straight to Downtown Tampa or St. Petersburg for dinner and weekend adventures.This is a rare opportunity to secure a prime waterfront canvas and bring your personal vision to life. Whether you dream of crafting a sophisticated coastal retreat or an effortless open-concept sanctuary, this home gives you the freedom to design every detail to your exact taste. Don’t just buy a house—create your dream waterfront lifestyle. Schedule your private tour today and start imagining the possibilities!

3090 Phoenix Avenue, 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
4798 Augusta Avenue, Oldsmar
$575,000
4 Beds ⋅ 3 Baths ⋅ Worthington SubDv. ⋅ 34677 Zip Code
Welcome to 4798 Augusta Ave, located within the desirable East Lake Woodlands community! Enjoy the peace and tranquility of a quiet, serene street where local wildlife sightings add to the charm of the neighborhood. Convenient resident entry provides quick access in and out of the community, making everyday travel a breeze. Inside, luxury vinyl plank flooring installed in 2023 offers a fresh, cohesive look throughout the home. The functioning fireplace adds warmth and character, while the whole-house water softener provides an added layer of everyday comfort. Major updates include a 2015 roof, 2019 A/C, impact-rated sliding glass doors installed in 2021, a rescreened lanai in 2021, and exterior paint completed in 2019 and interior painted in 2024. The home has never flooded. The community also features Ardea Country Club, where members can enjoy access to two 18-hole championship golf courses, a swimming pool, hard and soft tennis courts, pickleball courts, a playground, a gym, and Heron’s Bar and Grille With thoughtful updates, desirable community amenities, and a peaceful setting, this home is ready for its next owner to make it their own!

4798 Augusta Avenue, 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
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