Explore Homes for Sale in Oldsmar, FL

Discover Oldsmar, FL Homes for Sale

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Explore the diverse selection of homes for sale in Oldsmar, Florida. From waterfront properties to cozy family homes, discover your dream residence with Joseph Sullivan Real Estate. Begin your Oldsmar home search here and experience the vibrant lifestyle this community offers.

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Exploring the Oldsmar Real Estate Market

Oldsmar presents a unique real estate landscape, characterized by its blend of established neighborhoods and new construction. Finding the right home requires navigating this diverse market with expertise and a keen understanding of local trends. Joseph Sullivan Real Estate is here to guide you through the process.

Understanding Oldsmar's Neighborhoods

Oldsmar's neighborhoods each possess distinct character and charm. From the scenic views of waterfront communities to the family-friendly atmosphere of residential areas, understanding these nuances is key to finding the perfect home that matches your lifestyle. Explore the unique appeal of each neighborhood to discover where you truly belong.

Types of Homes for Sale in Oldsmar

The homes for sale in Oldsmar range from single-family houses to condos, townhouses, and luxury estates. Each property type offers a different living experience, and understanding the distinctions is essential to making an informed decision. Let's explore the various options available.

Single-Family Homes in Oldsmar

Single-family homes provide space, privacy, and a sense of community. These properties often feature spacious yards, multiple bedrooms, and various amenities. As you explore single-family homes in Oldsmar, consider your lifestyle needs and desired location to find the perfect fit.

Condos and Townhouses in Oldsmar

Condos and townhouses offer a low-maintenance lifestyle with access to shared amenities. These properties are often more affordable than single-family homes and provide a great option for those seeking convenience and community. Explore the diverse condo and townhouse options available in Oldsmar.

Navigating the Home Buying Process in Oldsmar

Buying a home involves several steps, from securing financing to negotiating the purchase agreement. Understanding each stage of the process is vital for a smooth and successful transaction. Joseph Sullivan Real Estate provides guidance and support every step of the way.

Finding the Right Home for You

Finding the right home requires careful consideration of your needs, budget, and desired location. As you browse homes for sale in Oldsmar, consider your priorities and work with a qualified real estate agent to narrow down your search and find the perfect property.

Newest Homes for Sale in Oldsmar, FL

4 Beds ⋅ 2 Baths ⋅ Manors Of Forest Lakes The SubDv.

Welcome to your private retreat in the heart of Oldsmar. Located in the desirable Longwood community, this beautifully maintained home offers the perfect blend of comfort, charm, and Florida living. Surrounded by mature landscaping and peaceful streets, 549 Longwood Circle features spacious living areas, abundant natural light, and an inviting layout ideal for both entertaining and everyday living. Step outside to enjoy a relaxing backyard setting with room to unwind, host gatherings, or create your own outdoor oasis. Conveniently located near top-rated schools, parks, shopping, dining, and the Gulf beaches, this home delivers both privacy and accessibility. Whether you're looking for a full-time residence or a seasonal getaway, this property is an incredible opportunity to own a piece of paradise in one of Tampa Bay’s most sought-after communities.

549 Longwood Circle, Oldsmar

4 Beds ⋅ 4 Baths ⋅ Turtle Creek Unit-One SubDv.

Welcome to an exceptional residence at 50 Kelleys Trail, nestled within the prestigious gated enclave of Turtle Creek within East Lake Woodlands in Oldsmar. This refined home embodies effortless elegance and elevated Florida living, offering a seamless blend of sophistication, comfort, and privacy. From the moment you enter, you’re greeted by soaring ceilings, abundant natural light, and thoughtfully designed living spaces that create an inviting yet upscale atmosphere. The open-concept layout flows beautifully, ideal for both intimate gatherings and grand entertaining. The kitchen serves as the heart of the home, featuring generous workspace, ample cabinetry, and a layout designed for both functionality and style. The primary suite is a true retreat, offering a serene escape with spacious proportions and a well-appointed en-suite bath. Step outside to your private outdoor setting, where you can unwind in tranquility or entertain guests while enjoying Florida’s year-round sunshine. Whether relaxing or hosting, this space offers the perfect backdrop for a luxury lifestyle. Located within one of Oldsmar’s most sought-after golf course communities, residents of East Lake Woodlands have access to optional resort-style amenities, including championship golf, tennis, fitness, and social experiences. Ideally positioned near upscale dining, boutique shopping, top-rated schools, Tampa International Airport, and the Gulf Coast’s renowned beaches, this home offers both convenience and exclusivity. Experience refined living in one of Oldsmar’s premier communities—schedule your private showing today.

50 Kelleys Trail, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Meadows Condo Unit Two At East Lake Woodlands The SubDv.

Strategically repositioned in the market with an improved price, this beautiful 2-bedroom, 2-bathroom condo in Oldsmar offers buyers an excellent opportunity to enjoy comfort, convenience, and a desirable Florida lifestyle. The residence features a functional floor plan with comfortable living spaces, well-proportioned bedrooms, two full bathrooms, hurricane-impact-resistant windows and sliding glass doors, and access to a community pool. Included services add even more convenience and value. Ideally located near major roadways, the property provides an easy commute to Tampa, Clearwater, and surrounding areas. Shopping, dining, entertainment, healthcare, and other everyday essentials are all nearby. Countryside Mall offers a variety of retailers and services, while local dining options include Starbucks, Chick-fil-A, and numerous neighborhood favorites. Mease Countryside Hospital is also conveniently located nearby, and Tampa International Airport is easily accessible for frequent travelers. Several important improvements have already been completed, including a new water heater in 2025, an A/C system installed in 2022, a refrigerator replaced in 2022, hurricane-impact-resistant windows and sliding glass doors installed in 2021, a microwave replaced in 2020, and a roof installed in 2019. With its convenient location, community amenities, valuable improvements, and newly enhanced price, this Oldsmar condo is ready for its next owner. Schedule your private showing today and discover everything this property has to offer!

202 Meadow Lane Unit 50, Oldsmar

Oldsmar Rev Map SubDv.

This office building and vacant lot can be combined for a price of $1,200,000 with the contiguous for sale property at 200 Lee St. that has a tenant occupied house. Both properties have a total of 33,806 sf (MOL) land with 350ft frontage on State St E. Both properties have an Oldsmar TCCN zoning designation (Town Center Commercial Neighborhood District). A unique and prime redevelopment opportunity across from the proposed Oldsmar Town Center, near by the City Hall, the Chamber of Commerce, the Galleria and the Odeon Town Home Square. Easy access to Tampa, St Pete/ Clearwater Int'l airports, shopping, food, hospitals, hotels and beaches. Sellers are very motivated and open for all combined or separate listing offers.

200 E State Street E, Oldsmar

2 Beds ⋅ 1 Baths ⋅ Oldsmar Rev Map SubDv.

This tenant occupied house can be combined for a price of $1,200,000 with the contiguous property for sale at 200 State St E. consisting of an office building and a vacant lot. Both properties have a total of 33,806 sf (MOL) land with 350 ft frontage on State St E. Both properties have an Oldsmar TCCN zoning designation (Town Center Commercial Neighborhood District). A unique and prime redevelopment opportunity across from the proposed Oldsmar Town Center, near by the City Hall, Chamber of Commerce, the Galleria and Odeon Town Home Square. easy access to Tampa, St Pete/ Clearwater Int'l airports, shopping, restaurants, hotels, beaches and hospitals. Sellers are very motivated and open for any combined or separate listing offers.

200 Lee Street, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Gull-Aire Village SubDv.

Welcome to refined Florida living in this luxurious 3-bedroom, 3-bath split floor plan residence located in the highly desirable 55+ community of Gull-Aire Village. Thoughtfully upgraded with both style and function in mind, this move-in ready home offers a rare and versatile layout featuring TWO PRIVATE ENSUITES—perfect for hosting guests or creating dual primary retreats. The interior showcases elevated finishes, including a beautifully updated kitchen with granite countertops and new appliances, premium bathroom fixtures, and designer lighting throughout. The home continues to impress with new luxury vinyl plank (LVP) flooring throughout, delivering a seamless blend of style, durability, and effortless maintenance. The home also features new subflooring and all-new siding, reflecting exceptional attention to detail and lasting quality. Designed for effortless living, the property features keyless entry, two dedicated storage spaces, a spacious two-car carport, and golf cart parking. An added outlet for a future mini-split system on the porch provides the opportunity to create a comfortable indoor-outdoor retreat tailored to your lifestyle. For added peace of mind, the home includes a 200-amp electrical panel, all new wiring, and completely updated plumbing throughout, along with newer impact windows, a tankless water heater, and a newer A/C system (approximately 4 years old), blending modern efficiency with comfort and security. Set within the vibrant and amenity-rich Gull-Aire Village community, residents enjoy resort-style amenities including a heated pool, clubhouse, shuffleboard, and an active social calendar. Conveniently located near pristine Gulf Coast beaches, dining, shopping, and medical facilities, this home offers both luxury and lifestyle. This is a rare opportunity to own a truly fabulous, move-in ready, and beautifully upgraded home in one of the area’s most sought-after communities.

193 Blue Marlin Drive, Oldsmar

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

Virtually Staged. Welcome home to this beautifully maintained 2-bedroom, 2-bathroom villa nestled in the highly desirable, gated community of East Lake Woodlands. Designed with both comfort and functionality in mind, this home features a desirable split-bedroom floor plan, offering privacy for both owners and guests, with a conveniently located shared bathroom for the secondary bedroom. Step inside and be greeted by a spacious living area perfect for entertaining, complete with a dedicated dining room and a stylish wet bar—ideal for hosting gatherings or enjoying a quiet evening at home. The well-appointed kitchen offers a full appliance package, abundant cabinetry, and ample counter space, making meal preparation a breeze. The generously sized primary suite serves as a relaxing retreat, featuring a walk-in closet and an updated en-suite bathroom with a large walk-in shower. An additional expansive family room provides even more flexible living space, perfect for a media room, home office, or casual lounging area. Enjoy seamless indoor-outdoor living as you step through sliding glass doors into your private, fenced courtyard—an inviting space to savor your morning coffee or unwind in the evening. Residents of East Lake Woodlands have the option to enjoy resort-style amenities, including a premier golf course, tennis courts, fitness center, dining, and a vibrant calendar of social events (membership optional). Conveniently located near shopping, dining, entertainment, and medical facilities, this home offers the perfect blend of tranquility and accessibility. Don’t miss your opportunity to make this exceptional villa your own—schedule your private showing today!

230 Balsam Drive, Oldsmar

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

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv.

Virtually Staged. Welcome to this two-bedroom, two-bath condominium in Oldsmar, offering 1,054 square feet and a flexible opportunity for investors, first-time buyers or seasonal residents. This residence is vacant and ready for immediate occupancy or renovation. The interior reflects the original condition, presenting a value-add opportunity for customization. The primary bedroom includes a walk-in closet, and the layout supports functional living and dining spaces. Recent updates include an air-conditioning system installed in 2025, along with a washer, dryer and refrigerator replaced in 2024. This property is well-suited for buyers seeking to personalize a residence or secure an investment with long-term potential. Conveniently near shopping, dining and commuter routes, supporting full-time and seasonal living.

130 Cypress Lane Unit 130, Oldsmar

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

Welcome to 120 Evelyn Ct, Oldsmar, FL 34677, a beautifully maintained villa located within the highly desirable East Lake Woodlands community, one of the most sought-after neighborhoods in Pinellas County and the Tampa Bay area. This home offers a wonderful opportunity for buyers seeking low-maintenance living in a prime Oldsmar location. This immaculate villa has been very well maintained through the years and is ready for move-in, while also allowing the next owner the opportunity to update and personalize over time. The home features a thoughtfully designed floor plan with spacious living areas and generously sized bedrooms, creating a comfortable and functional living environment. The primary suite includes a walk-in closet and private ensuite bathroom, providing privacy and convenience. The additional bedroom is also well-sized, making the home ideal for guests, seasonal living, or a home office. One of the standout features of this property is the large sunroom/lanai, offering a bright and inviting space that can be enjoyed year-round. Whether you’re relaxing with your morning coffee or entertaining guests, this versatile area adds valuable living space and enhances the overall flow of the home. Important updates include an HVAC system installed in 2015, a new electrical panel installed in 2022, and a newer water heater, providing peace of mind for the next owner. The property also includes covered parking and ample storage space, adding convenience for everyday living. The home is fairly priced based on recent comparable sales within the East Lake Woodlands community, making it a strong opportunity in today’s Oldsmar real estate market. East Lake Woodlands is known for its beautiful surroundings, mature landscaping, and central location within Pinellas County. Residents enjoy easy access to shopping, restaurants, parks, golf courses, and everyday conveniences. The property is also conveniently located with an estimated 30-minute drive to Tampa International Airport, as well as a similar drive to many of Pinellas County’s award-winning Gulf Coast beaches. If you are searching for a villa in Oldsmar within East Lake Woodlands, 120 Evelyn Ct offers a combination of location, comfort, and value in one of the Tampa Bay area’s most desirable communities. Schedule your private showing today and discover everything this well-maintained Oldsmar villa in East Lake Woodlands has to offer.

120 Evelyn Court, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Quail Forest Cluster Homes SubDv.

Virtually Staged. Welcome to 10 Lesley Lane, located in the gated community of Quail Forest, nestled within the private country club community of East Lake Woodlands. This beautifully maintained end-unit villa offers serene pond views and a thoughtfully designed split-bedroom floor plan for added privacy and comfort. Major updates provide peace of mind, including a new roof (2022), HVAC (2023), and water heater (2022). The spacious, fully updated kitchen is a true highlight, featuring new cabinetry, sleek quartz countertops, and stainless steel appliances, perfect for both everyday living and entertaining. The layout flows effortlessly into the living and dining areas, all filled with natural light and peaceful water views. Enjoy your morning coffee or unwind in the evening on the charming front patio. Additional conveniences include one assigned carport and plenty of guest parking for visitors. Residents of East Lake Woodlands have access to two championship golf courses, consistently ranked among the top 5 in the entire Tampa Bay area, along with optional country club amenities. Ideally located near shopping, dining, parks, and just a short drive to Tampa International Airport and the Gulf beaches, this home offers the perfect blend of lifestyle and location. Don’t miss your opportunity to own in one of Oldsmar’s most desirable communities!

10 Lesley Lane, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Hayes Park Village SubDv.

NEW PRICE! Location, location, location is the key to finding the perfect home - and this one delivers on every level. If you have been searching for a place that blends character, convenience, and community, look no further. This charming 3-bedroom home with an attached garage, sits in the picturesque neighborhood of Hayes Park Village, a community that feels like a slice of the French Quarter right here in Florida. Nestled in the heart of the City of Oldsmar, this home offers the best of old-world-charm with modern comfort. Oldsmar is a great City known for having more parks per sq. mile than any other city in the state along with excellent schools and an abundance of activities for all ages. Also, the home of Tampa Bay Downs and Tampa Bay Skating Academy. It is a place where community pride runs deep and quality of life comes naturally. The homes inviting wrap-around porch sets the tone from the moment you arrive. Enjoy your morning coffee as you look out to the neighborhood courtyard complete with a welcoming fire pit, creating the perfect setting for neighborhood gatherings. Inside the home, gleaming hardwood floors flow through an open concept living space that feels both spacious and cozy. The kitchen is beautifully appointed with granite countertops and 36" cabinets and a center island that anchors the room- ideal for cooking, entertaining or simply enjoying daily life. A convenient first floor powder room adds practicality for guest and family alike. The master suite opens to a second floor balcony that overlooks the lake and Richard B. Rogers Park. The Master bedroom also features a tray ceiling with crown molding and an upgraded bathroom with frameless glass shower enclosure and a walk-in closet. Two additional ample sized bedrooms and a guest bath complete the upstairs. THIS HOME HAS BEEN WELL MAINTAINED; ROOF IS JUST OVER A YEAR OLD AND THE AC IS JULY OF 2025, WATER HEATER REPLACED IN 2024. The PERFECT LOCATION connects TAMPA to PINELLAS COUNTY. Close commute to Tampa International Airport and International Mall. Within minutes of Clearwater and downtown Safety Harbor, Approximately 30 minutes to the Gulf Coast Beaches.Current owner pays $1081 for FLOOD INS. Policy is transferable to new Buyer. NEVER FLOODED.

208 Cutlass Way, Oldsmar

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