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 ⋅ 3 Baths ⋅ East Lake Woodlands SubDv.

One or more photo(s) has been virtually staged. NEW PRICE. SERIOUS VALUE. Located inside the highly desirable gated community of Ardea / East Lake Woodlands, this spacious 4-bedroom, 2.5-bath residence offers an expansive 2,922 sq ft of living space on an oversized lot with peaceful water views. Step inside to soaring ceilings and an open, light-filled floor plan designed for both everyday living and entertaining. The home features expansive living areas including a formal living and dining room and a large family room with fireplace. New Luxury Vinyl Plank flooring installed in 2026 runs throughout the main living areas, creating a modern and cohesive look, while new carpet installed in 2026 adds comfort to the guest bedrooms. The updated kitchen features granite countertops and stainless-steel appliances, flowing seamlessly into the main living space and breakfast area—perfect for gatherings and everyday living. The spacious primary suite offers direct access to the pool area along with a private bath and generous closet space. Enjoy Florida living at its best with a screened pool and lanai overlooking a tranquil pond, providing both privacy and relaxing water views. The home also features fresh exterior paint completed in 2026 and a 3-car garage, all situated on a generous homesite within this established golf-course community. Residents of East Lake Woodlands have the option to join the Ardea Country Club, a recently renovated club offering two championship golf courses, tennis and pickleball courts, fitness facilities, resort-style pool, and multiple dining venues. The club provides a vibrant social calendar and family-friendly amenities, creating a true country club lifestyle right inside the community. Located just minutes from shopping, dining, top-rated schools, and major commuter routes, this home offers convenient access to Tampa International Airport, Gulf beaches, and the best of the Tampa Bay area. Close to all the Tampa Bay Area has to offer; Championship golf courses, Tampa International Airport, NHL, NFL, MLB events, Grand Prix, PGA events, fine dining, concerts, parks, biking trails, BMX events, and more. Begin Your Paradise Life Today.

470 Hickorynut Avenue, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv.

This beautiful townhouse (NEVER FLOODED) is located in the highly desirable waterfront gated community of Bayside Terrace. The home offers three bedrooms and two and a half bathrooms with a modern, open layout designed for comfortable living and entertaining. The 9 foot ceilings enhance the spacious feel and allow natural light to flow throughout the home. There is no immediate rear neighbor, providing added privacy and a more open feel from the lanai. Grilling is allowed in the backyard area, giving you the ability to enjoy outdoor cooking and entertaining. The home has been meticulously kept and shows true pride of ownership. It also includes a private 1 car garage for secure parking and additional storage. Upon entering, you immediately notice the ultra-modern feel and the exceptionally well-maintained condition of the property. The spacious kitchen features an extra-large island that is so generously sized it feels like it has its own zip code, along with an under-mount sink, quartz countertops, stainless steel appliances, and a walk-in pantry. The main living area has tile flooring throughout, creating a clean and seamless look, and opens to a screened-in lanai with brick pavers for easy indoor and outdoor living. Upstairs, the upgraded Berber-carpeted staircase with elegant railing leads to a loft area and all bedrooms. The primary suite is generously sized and includes multiple walk-in closets and a beautifully designed en-suite bathroom. Bedrooms two and three each feature carpeting and their own walk-in closets, offering excellent storage and flexibility. The home also includes hurricane shutters stored in the garage, providing added storm protection and peace of mind. Bayside Terrace offers resort-style amenities including a waterfront infinity heated salt-water pool, a covered pavilion overlooking the water, a cabana, two BBQ grills, a gas fire pit, a fitness center, clubhouse, and a dock with kayak and canoe launch access. The gated entrance and deed restrictions add an extra layer of privacy and security, while the waterfront setting allows residents to enjoy Florida sunsets and an active coastal lifestyle. Please view two videos: Tour 1 & Tour 2.

1505 Sunset Wind Loop, Oldsmar

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

Located in East Lake Woodlands this quiet private second-story unit offers serene views overlooking the golf course and has a bright welcoming interior. Thoughtfully remodeled throughout, the home features abundant cabinet space, newer appliances, and major system upgrades including air conditioner and furnace. The unit has been tastefully finished with beautiful Florida-style decor, creating a light and relaxed atmosphere, perfect for full-time living or a seasonal retreat. Enjoy privacy, natural light and tranquil surroundings. Pool recently renovated and heated. Furnishings included if desired. Room measurements are estimated. Buyer agent and buyer to verify

104 E Cypress Court Unit 104, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Hayes Park Village SubDv.

Welcome to this impeccably maintained 3 bedroom, 2.5 bath residence in the highly sought-after Hayes Park Village in Oldsmar. Offering approximately 1,392 square feet of thoughtfully designed living space, this home showcases a beautifully renovated kitchen with contemporary finishes, ceramic flooring on the first floor, and carpet flooring on the second floor. The split-bedroom floor plan and abundant natural light create a bright, open atmosphere that is both welcoming and functional. Step outside to a covered porch overlooking a breathtaking pond and a serene conservation area behind it —providing exceptional privacy. Combining generous living space, peaceful privacy, and an unbeatable location, this exceptional home is ready to welcome YOU!

103 Cutlass Way, Oldsmar

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

Nestled in the highly deisrable City of Oldsmar, this home has been tastefuly renovated. You'll love the updated kitchen with new stainless steel appliances, stone counter top and lovely build in desk. This modern kitchen has beautiful black cabinets, double sink, new range, refrigerator, dishwasher, and microwave. There are new ceiling fans throughout the home and plenty of decorator lighting. The master suite has it's own bath and modern shower. It is a beauty. The secondary bath is very modern with decorator fixtures and lighted mirror, all done very tastefully. This shower has beautiful ceramic tile and modern features. There is spacious great room and separate dining room which is leading to the perfect entertaining back yard. There are 2 decks, brick pavers and it features a jacuzzi tub. You'll love the separate shed for storage and fenced in yard. There is plenty of room for your toys with gated entry to the back yard. No CDD or HOA fees here but there are several parks and a boat ramp in the neighborhood. Move in ready and a must see.

416 Country Club Drive, Oldsmar

6 Beds ⋅ 5 Baths ⋅ Deerpath Unit One SubDv.

Tucked away on a quiet cul-de-sac inside the gated East Lake Woodlands community, this 4,475-square-foot home offers something that's becoming increasingly difficult to find in Tampa Bay: **property and privacy.** Situated on 1.4 wooded acres with no rear neighbors, you'll enjoy peaceful conservation views from nearly every room, along with a 2,000-square-foot screened pool and outdoor entertaining area designed for everything from quiet mornings with coffee to weekend gatherings with family and friends. Yet you're never far from the conveniences of everyday life. Boot Ranch shopping, including Publix, Target, and Walmart Neighborhood Market, is just 7 minutes away. East Lake Middle and High School are within 12 minutes, and restaurants, shopping, and entertainment are all close by. Inside, the home offers an incredibly flexible floor plan with room for just about every lifestyle. The main level features the primary suite, a dedicated office (or fifth bedroom), formal dining room, second bedroom with a full bath, spacious laundry room, family room, game room, and a private in-law suite with its own entrance—ideal for multigenerational living, long-term guests, or a home business. Recently painted throughout, the main living areas showcase beautiful Turkish herringbone tile flooring, soaring ceilings reaching nearly 25 feet, and abundant natural light with tranquil views of the conservation beyond. At the center of the home is a kitchen designed for gathering. Granite countertops, stainless steel appliances, custom cabinetry, a prep sink and island, breakfast bar, pantry, and built-in desk provide exceptional functionality, while the oversized breakfast area comfortably accommodates an eight-person table. The kitchen flows seamlessly into the family room, where a wood-burning fireplace and wet bar create the perfect setting for entertaining. Upstairs, you'll find two generously sized bedrooms connected by a Jack-and-Jill bath, along with an oversized loft overlooking the family room below. Whether you envision a media room, game room, home gym, or second family room, the possibilities are endless. Additional walk-in storage provides plenty of space to stay organized. Residents enjoy the security of East Lake Woodlands' 24-hour manned gate, along with the added privacy of the gated Deerpath enclave. Optional membership to East Lake Woodlands Country Club offers golf, tennis, fitness, dining, and social amenities just minutes from your front door. Homes offering this much space, privacy, flexibility, and location rarely become available. Schedule your private tour and experience it for yourself.

50 Willowood Lane, Oldsmar

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

"Move-In Ready"... Freshly Painted and Beautifully completely Refurbished Single Family Pool Home, (3) Bedrooms, (2) Baths with plenty of storage space, vehicles, boat and golf cart(s) parking. Luxury vinyl flooring throughout this split plan homes interior, picturesque French Door views to the pool and lanai deck, all new kitchen appliances and home systems installed. An expansive corner lot property with plenty of green space, fenced yard and mature landscaping. Enjoy your Florida Lifestyle with family and social gatherings within the updated interior decor or outside in the screened pool and lanai deck area. We'll look forward to your visit.

347 Country Club Drive, Oldsmar

Prime Vacant Lot – Oldsmar, FL - Exceptional opportunity to build in a prime Oldsmar location just one block from waterway to Safety Harbor. This cleared and leveled vacant lot is ideally situated near top-rated schools, parks, restaurants, and the charming downtown of Safety Harbor. Convenient access to Tampa International Airport and major roadways makes commuting a breeze. Located in an area experiencing new single-family home construction, this lot offers excellent potential for a custom residence or investment build. This lot features a pre-existing driveway allowing access to the road, connection to water, sewer and access to power grid. Enjoy a quiet neighborhood setting with proximity to outdoor recreation, waterfront activities, and everyday conveniences. Don’t miss this rare chance to secure a buildable lot in a desirable and growing community. Ideal for buyers looking to create their dream home in a well-established area with strong long-term value.

503 Buckingham Avenue W, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gardens Of Forest Lakes Condo The SubDv.

This beautifully maintained 2 bedroom, 2 bath condo in fantastic Gardens of Forest lakes, offers perfect blend of comfort and convenience. As you step inside, you will be greeted by an open floor plan that seamlessly connects the living and kitchen areas. Kitchen features granite countertops, wood cabinets. The dining area opens to a charming balcony overlooking trees and it is perfect for relaxing after a busy day. Both bedrooms are very spacious with nice size closets. In unit laundry room. Second floor end unit. The Gardens of Forest Lakes community offers pool, park, playground, tennis and racquetball courts, picnic spots, lake access, and a large dock for fishing. Great location easy commute to Tampa & Pinellas. Close to shopping, beaches and entertainment. No age restriction, Owner can lease with no waiting period. The condo is ideal for a first time home buyer or as an addition to your investment portfolio. Do Not Miss Out on this unit that offers the perfect blend of comfort.

134 Sycamore Lane Unit H, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Country Club Add To Oldsmar Rev SubDv.

STUNNING TAMPA BAY VIEWS! UPDATED OLDSMAR SPLIT-LEVEL WITH RV/BOAT PAD! Breathtaking Tampa Bay views await in this updated, elevated home in one of Oldsmar’s most desirable neighborhoods! Just steps from the water, this 3-bedroom, 2-bath residence offers the perfect blend of peace of mind and outdoor living. The split-level design ensures durability, with a spacious 2-car garage on the ground level and all living areas elevated. Major upgrades include a new roof, a newer water heater (<5 years), and a renovated primary suite featuring a walk-in closet. The kitchen shines with stylish quartz countertops, and a large first floor laundry room. Step outside to your fully fenced, level backyard—ideal for entertaining or relaxing in the screened-in porch. The property includes a dedicated RV or Boat pad. Enjoy an incredible lifestyle within walking distance or take your golf cart to the waterfront parks, nature trails, pickleball courts, a fishing pier, and playgrounds. Located in a top-rated school district. This home is the complete package.

317 Shore Drive E, Oldsmar

2 Beds ⋅ 3 Baths ⋅ Emerald Bay SubDv.

Heart of Oldsmar convenient to restaurants, shopping and Tampa. 2 Story, 2 Bedroom / 2.5 Bathroom Townhome in Oldsmar, AC 7/23, newer luxury vinyl flooring and newer paint.

62 Emerald Bay Drive, Oldsmar

Oldsmar Rev Map SubDv.

Virtually Staged. DOUBLE LOT!!! Rare opportunity to own a fantastic piece of land in the heart of Oldsmar, Florida! This versatile property offers subdivision potential, allowing the parcel to be divided and sold individually—ideal for builders, investors, or buyers looking to create custom homes in a growing and highly desirable area. Located near top-rated local schools, this property places you right in the center of everything Oldsmar has to offer. Enjoy easy access to Oldsmar’s many parks, scenic outdoor spaces, zip-lining adventures, the popular Oldsmar Flea Market, and a variety of restaurants, shopping, and recreational options. Nature lovers will appreciate the abundance of nearby trails and waterfront parks, while convenience seekers will love the quick access to major roadways. Perfectly positioned between Tampa and Clearwater, this location provides seamless access to even more dining, entertainment, beaches, and employment hubs—offering the best of both suburban charm and city convenience. Whether you’re looking to develop, invest, or build, this property presents a unique opportunity in one of Pinellas County’s most dynamic and well-connected communities. Don’t miss your chance to bring your vision to life in Oldsmar!

311 Washington Avenue, Oldsmar

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