Oldsmar Homes with Two Story Style

Oldsmar Homes with Two Story Style

Welcome to the charming city of Oldsmar, located in Pinellas County, Florida. Known for its picturesque landscapes and friendly community, Oldsmar is a hidden gem waiting to be discovered.

One of the unique features of homes in Oldsmar is the abundance of two-story style properties. These homes offer spacious layouts and a classic design that exudes elegance and character. Whether you're looking for a cozy family home or a stylish retreat, Oldsmar has a variety of two-story homes to suit your needs.

Living in Oldsmar means enjoying a relaxed lifestyle with easy access to beautiful beaches, parks, and recreational activities. The city also boasts a vibrant downtown area with shops, restaurants, and entertainment options for residents to explore.

With its convenient location in the heart of Pinellas County, Oldsmar provides easy access to major highways, making it a great choice for commuters and those looking to explore the surrounding areas.

If you're searching for a home that combines style, comfort, and charm, look no further than Oldsmar. Discover the beauty and warmth of this welcoming city and find your perfect two-story home in this delightful community.

Newest Oldsmar Homes with Two Story Style

5 Beds ⋅ 4 Baths ⋅ TB8534625 MLS

Exceptional builder or investor opportunity in a prime Oldsmar location! Situated on an oversized 11,347 sq. ft. lot directly across from scenic R.E. Olds Park, this property offers partial water views of Tampa Bay, park views, and outstanding redevelopment or renovation potential. The existing structure includes a 3-bedroom, 2-bath upper level plus two 1-bedroom, 1-bath lower-level units, offering multiple possibilities for redevelopment or renovation (buyer to verify permitted use). Additional features include a 2-car carport and a concrete block storage building. Enjoy a golf cart-friendly community with walking trails, fishing pier, playgrounds, picnic shelters, and year-round events just across the street. Cash offers only. Property is being sold As Is with no repairs. Conveniently located with easy access to Tampa, St. Petersburg, Tampa International Airport, and Gulf beaches.

613 Chestnut Street, Oldsmar

2 Beds ⋅ 3 Baths ⋅ TB8534362 MLS ⋅ N/A BLDG.

Welcome to this 2-bedroom, 2.5-bath townhome located in the desirable gated community of Countryside Key in the heart of Oldsmar. This spacious floor plan features two primary suites upstairs, each with its own private bathroom, while the convenient half bath downstairs is perfect for guests. Enjoy an open living and dining area with plenty of natural light and a private screened patio ideal for relaxing or entertaining. The seller is offering a concession toward new flooring and/or appliances, providing a great opportunity to personalize the home to your own style. Residents of Countryside Key enjoy access to a community pool, tennis courts, and beautifully maintained grounds, all just minutes from shopping, dining, parks, top-rated schools, Tampa International Airport, and the beaches.

366 Countryside Key Boulevard, Oldsmar

3 Beds ⋅ 2 Baths ⋅ TB8530374 MLS ⋅ 208 BLDG.

Beautifully updated condo in East Lake Woodlands with 3 bedrooms, 2 full baths, 1 car garage and an added BONUS space/office! Right as you enter, notice the entire entryway is newly UPDATED with a custom door, paint, sconce lighting and Stanton carpet up the stairwell. Prepared to be wowed in the living room by the elegant, NEW custom built entertainment center with an electric fireplace. Set your color of choice and it can heat up the room for chilly nights. With the natural light, luxury vinyl plank flooring, vaulted ceilings, 2 huge fans on remotes.. this is quite the spot for entertaining. Kitchen features newer leathered granite countertops, wood cabinetry with soft close doors, stainless steel appliances, breakfast bar and new custom drapes. Step outside to the fully screened lanai with adjustable sunshades. Cool off with a new variable speed fan while enjoying all the wildlife East Lake Woodlands as to offer. The owner's suite also has a sliding door to the lanai, 2 closets with ample space, double bathroom vanities, countertops, garden tub and floor-to-ceiling tiled, glass-enclosed shower. Two other bedrooms with large windows share an updated bathroom. Enjoy an upstairs inside laundry with storage space and a bonus room with a convenient wet bar area. This space can be a TV room, office, playroom, sitting room for morning coffee..the ideas are endless. Additional updates include NEW water heater, new epoxy garage floor, remote blinds, and light fixtures. HOA fee includes internet, cable, water, sewer, trash, community pool, exterior maintenance, grounds and insurance. Furniture is also available for purchase. East Lake Woodlands is central to Florida's most famous beaches, shopping, Tampa airport, A-rated schools and numerous dining options. There also is an option to join the Ardea Country Club and have access to 2 championship golf courses, tennis courts, fitness center, clubhouse, dining, swimming pools and social events. Don't miss this opportunity!

208 Clays Trail Unit 208, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8529492 MLS ⋅ 2410 BLDG.

Imagine coming home to breathtaking waterfront surroundings, resort-style amenities, and maintenance-free living in one of Tampa Bay's most desirable gated communities. Welcome to Bayside Terrace, where this beautifully upgraded 3-bedroom, 2.5-bath townhome with a 1-car garage offers the perfect blend of luxury, convenience, and coastal lifestyle. Ideally situated just steps from the community pool and clubhouse, this move-in-ready residence features one of the community's most desirable locations with peaceful courtyard views and easy access to all the amenities. Designed for today's lifestyle, the open-concept floor plan showcases soaring ceilings, abundant natural light, and elegant wood-look tile flooring throughout the main living areas. The chef-inspired kitchen is the centerpiece of the home, featuring stunning quartz countertops, custom all-wood cabinetry with pull-out shelving, a large quartz preparation island, designer lighting, a walk-in pantry, stylish backsplash, and premium stainless steel appliances including a double oven range and French door refrigerator. Whether entertaining guests or enjoying quiet evenings at home, this space was designed to impress. The spacious great room flows seamlessly onto the covered and screened lanai, creating an inviting indoor-outdoor living experience overlooking a tranquil courtyard. It's the perfect setting for morning coffee, evening cocktails, or simply relaxing after a day on the water. Upstairs, a versatile loft provides flexible living space that easily serves as a home office, media room, fitness area, or second family room. The luxurious owner's suite offers a true retreat with an oversized walk-in closet, dual vanities, linen storage, and a beautifully Upstairs, a versatile loft provides flexible living space that easily serves as a home office, media room, fitness area, or second family room. The luxurious owner's suite offers a true retreat with an oversized walk-in closet, dual vanities, linen storage, and a beautifully appointed frameless glass shower. Two additional bedrooms each feature walk-in closets, ceiling fans, and upgraded carpeting with premium padding for exceptional comfort. Living in Bayside Terrace means enjoying a true Florida waterfront lifestyle. Residents have exclusive access to a resort-style swimming pool, fitness center, clubhouse, fishing pier, kayak launch, and direct access to the beauty of Tampa Bay. Whether you enjoy kayaking, fishing, walking along the waterfront, or simply watching spectacular sunsets, every day feels like a vacation. Included with all of these amenities, the HOA offers exterior property insurance, high speed internet, cable tv, maintenance of exterior and pool, 24 virtual guard gate, common area taxes plus water, sewer and trash. Perfectly positioned between Hillsborough and Pinellas Counties, this exceptional location offers convenient access to Tampa International Airport, St. Pete-Clearwater International Airport, downtown Tampa, award-winning Gulf beaches, waterfront dining, shopping, and major employers. Whether you're searching for a waterfront townhome, a gated community with resort amenities, a low-maintenance primary residence, a second home, or a Florida retreat close to Tampa and the Gulf Coast, this exceptional property offers everything today's buyers are looking for. Schedule your private showing today and discover why Bayside Terrace continues to be one of Tampa Bay's most sought-after communities.

2410 Arch Avenue, Oldsmar

4 Beds ⋅ 3 Baths ⋅ TB8527516 MLS

Welcome to 1745 Oak Pond Court! Welcome to 1745 Oak Pond Court, a beautiful home located in the sought-after East Lake Oaks community. Situated on a quiet street with a premium lot, this home offers comfort, style, and numerous recent upgrades. The interior and exterior have been freshly painted, and the screened lanai has been recently updated. Some major updates include a new water heater installed in 2022, a new air-conditioning system installed in 2023, new carpeting on the stairs completed in May 2026, and stair railings that were sanded and freshly painted in May 2026. The primary bathroom was completely remodeled in 2022 and features a relaxing jetted tub, updated vanity, shower, tile flooring and walls, surround-sound speakers, and mood lighting in the ceiling. A luxurious outdoor kitchen was installed in 2025 and includes a grill, granite countertop, stainless-steel sink, and stainless-steel storage for all your entertaining needs. Additional improvements completed in June 2026 include freshly painted pool patio and garage floor. The kitchen was updated in 2022 with new cabinets and granite countertops, while wood-look laminate flooring was installed throughout the downstairs living areas. Conveniently located near Tampa International Airport, shopping, nature trails, and excellent restaurants, this home is also just twenty minutes from Honeymoon Island Beach. This move-in-ready home combines thoughtful upgrades, a prime location, and Florida living at its best!

1745 Oak Pond Court, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8526165 MLS ⋅ 50-100 BLDG.

Experience resort-style living in this beautifully renovated 2-bedroom + loft, 2-bath condominium offering approximately 1,600 square feet of bright, open living space. Perfectly positioned overlooking tranquil water and the golf course, this exceptional home combines modern updates with soaring architectural details in one of Oldsmar's most desirable communities. The impressive great room welcomes you with dramatic vaulted ceilings, abundant natural light, and a striking spiral staircase leading to a versatile loft—ideal for a home office, media room, or guest space. The remodeled kitchen features crisp white cabinetry, quartz countertops, stainless steel appliances, recessed lighting, and a breakfast bar that opens seamlessly to the living and dining areas. The spacious primary suite offers peaceful water views, private access to the screened lanai, a custom walk-in closet, and a beautifully renovated en-suite bath complete with a luxurious oversized walk-in shower and dual vanities. The generous second bedroom is located near the updated guest bath, providing privacy for family or visitors. Step outside to the expansive screened lanai and enjoy picturesque views of the pond and golf course—the perfect setting for your morning coffee or relaxing evenings. Features You'll Love 2 Bedrooms + Spacious Loft 2 Fully Updated Bathrooms Approximately 1,600 Sq. Ft. Soaring Vaulted Ceilings Dramatic Spiral Staircase Beautifully Renovated Kitchen with Quartz Counters Stainless Steel Appliances Luxury Vinyl Plank Flooring Throughout Custom Walk-In Closet Oversized Primary Shower with Designer Tile Full-Size Washer & Dryer Large Screened Lanai Water & Golf Course Views Assigned Covered Parking Located just minutes from shopping, restaurants, parks, Tampa International Airport, and some of the area's best beaches, this move-in-ready home offers the perfect blend of comfort, style, and convenience. Schedule your private showing today and discover everything this exceptional Oldsmar home has to offer! Newer AC 3/2022.

60 St Andrews Place Unit 60, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8526089 MLS ⋅ N/A BLDG.

Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome (NEVER FLOODED) in one of Oldsmars most desirable waterfront gated communities. This move-in-ready home offers comfort, convenience and low-maintenance resort style living. The open-concept layout is designed for both everyday comfort and effortless entertaining, featuring a spacious living and dining area filled with natural light. Inside features new carpeting in all bedrooms, new ceiling fans throughout, in wall pest system and a recently serviced HVAC system. The open layout is perfect for everyday living and entertaining. Enjoy the screened-in lanai, ideal for relaxing, gardening, or morning coffee. The pet-friendly community offers sidewalks and green space for outdoor enjoyment. HOA covers water, trash, cable, high-speed internet, exterior maintenance, and 24-hour virtual guard service, providing exceptional value and ease of living. Community amenities include a fitness center and resort-style pool overlooking the Bay. Conveniently located near shopping, dining, parks, Gulf beaches, top-rated schools and both Tampa International and PIE airports. Assumable Mortgage Available! *If qualified* Whether you're searching for a primary residence, or luxury vacation home, this exceptional resort style townhouse community delivers a low-maintenance lifestyle, comfort, and location in one impressive package.

1309 Sunset Wind Loop, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8512390 MLS

Virtually Staged. Welcome to this inviting single-family home in the sought-after Kingsmill neighborhood of East Lake Woodlands—a premier gated community celebrated for its security, lush Florida landscapes, and vibrant lifestyle. Offering 2,453 square feet of living space, this beautifully updated residence features a grand total of three bedrooms, two full bathrooms, and a modernized half bath. Inside, the interior features soaring cathedral ceilings, fresh flooring, and brand-new carpeting. The main level hosts a formal dining room and an open kitchen that flows effortlessly into a spacious great room, complete with a cozy gas-burning fireplace. The primary suite is conveniently situated on the main floor, boasting a stunning, fully remodeled bathroom. Upstairs, discover the remaining bedrooms—including a flexible third bedroom created by walling in the former loft space, making it ideal for a quiet home office or guest room—alongside another full bath. Outside, the large backyard overlooks a peaceful pond and features an inground pool and spa under a brand-new screen enclosure, complemented by a built-in outdoor kitchen setup. Living here means embracing the East Lake Woodlands lifestyle. Residents can enjoy miles of scenic nature and biking trails, while a variety of optional club memberships unlock access to championship golf courses, a premier tennis and pickleball complex, resort-style swimming pools, and a private clubhouse with fine dining and social events. Located in the heart of Oldsmar, this property is also just minutes from excellent shopping, dining, highly rated schools, and pristine Gulf Coast beaches. Don’t miss the opportunity to make this Kingsmill gem your own. Schedule a private tour today to experience this beautiful pond-front retreat firsthand!

586 Kingsmill Court, Oldsmar

5 Beds ⋅ 4 Baths ⋅ TB8512698 MLS

Unique opportunity to own a one-of-a-kind, beautiful property on Safety Harbour Bay with Direct access to Tampa Bay. Renovation by Herman Builders. The stunning modern completely updated home features: contemporary, Open and spacious Gourmet Chef's Kitchen High-end chef-quality appliances, with double ovens, fireplace Oversized Island loads of cabinets, storage , the home has natural stone floors throughout. Full water views across the entire back of the home large glass doors leading out to your beautiful contemporary pool. Boat Docs for keeping your boat and easy access to Tampa Bay for the deep water fishing. The home features mother-in-law's quarters separate from the main home. With kitchenette, and private entrance . On the main floor, there are also three Guest or family bedrooms a bonus space, laundry room , lots of storage. The Private owner's suite features a large spa bathroom fabulous walk-in closets with grand views of Safety Harbor bay. Conveniently located near airport and downtown with the best schools in Tampa.

412 Shore Drive E, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8514350 MLS ⋅ 202 BLDG.

AS IS – Owner selling due to health concerns! This spacious 3-bedroom, 2.5 bath, townhome in the highly desirable community of Sun Ketch Townhomes of Cypress Lakes needs some cosmetic attention, but the structure and amenities are already there: vaulted ceilings, an inside laundry room, a kitchen pantry, a walk-in bathtub in the primary bathroom, and an enclosed porch, and much more. A new A/C unit was installed in October 2017. The HOA Fee is only $240 monthly. HOA Documents are available for review - contact the listing agent.

202 Hemingway Drive, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8510265 MLS

One or more photo(s) has been virtually staged. Welcome to your private retreat in the gated community of Bay Arbor! Major Upgrades Include: New Roof (2022), New AC (2026), New Hurricane impact Windows and Doors (2024), New Screen Patio Screen Enclosure (2024), and much more! Nestled on a spacious wooded homesite, this beautifully maintained two-story home offers over 3,000 square feet of thoughtfully designed living space blending comfort, privacy, and everyday convenience. Porcelain tile and wood-like flooring throughout- No carpet. From the moment you step inside, you’re greeted by soaring ceilings, an open staircase, and an abundance of natural light. The formal living and dining rooms create the perfect setting for entertaining guests or hosting holiday gatherings. At the heart of the home, the spacious Updated kitchen with quartz countertops, stainless steel appliances and flows effortlessly into the inviting family room, all overlooking tranquil wooded views that bring a sense of peace and serenity indoors. Whether you're enjoying a quiet evening at home or entertaining, this layout was designed for both relaxation and connection. Upstairs, the primary suite serves as a true escape featuring an updated spa-inspired ensuite bath with dual sink vanity, soaking tub, and a step-in shower. Two additional generously sized bedrooms offer ample closet space and share a beautifully appointed bathroom. A large upstairs bonus room provides endless flexibility, ideal as a media room, second living area, home office, playroom, or gym. Step outside to your screened patio and enjoy the beauty of your private fenced backyard oasis surrounded by mature trees and nature views. It’s the perfect place for morning coffee, evening sunsets, or weekend gatherings. Located just minutes from Tampa, award-winning Gulf beaches, airports, major highways, top-rated schools, shopping, dining, and entertainment, this exceptional home offers the perfect balance of peaceful living and city convenience. Rarely does a home combine space, privacy, location, and lifestyle so effortlessly. Schedule your private showing today! HOA is $600 semi-annually and includes the Community Pool and playground.

380 Rosalind Lane, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8502559 MLS ⋅ Na BLDG.

Nature lovers! Enjoy the abundant wildlife and tranquil creek/preserve views from the patio and 2nd floor balcony of this fabulous townhome nestled in the heart of East Lake Woodlands, among the premier gated country club communities in northern Pinellas County! The primary suite—created by combining what was originally two bedrooms—feels exceptionally spacious, with plenty of room to unwind, and it can easily be reconfigured if a total of 3 bedrooms are needed. Many terrific features, including a huge great-room floor plan, roof (2025).... all in 2024: new luxury vinyl plank flooring in main areas, new kitchen cabinets/ granite countertops along with all new appliances, kitchen lights, washer/dryer, hot water heater, water softener, A/C (2018), painting exterior will be done July 2026, designated carport with storage, very large screened lanai, and so much more! Fantastic location, close to award winning beaches, airports, Pinellas Trail, golf courses, tennis club, St Pete, Tampa, restaurants, hospitals, and shopping! Don't pass up this special gem of a home in a special community at a great price! ***FYI, Zillow has not updated 2025 property tax of $2149, property is homesteaded and carries through for next homesteaded buyer***

110 Ingrid Place, Oldsmar

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