Oldsmar Homes with Two Story Property Description

Oldsmar Homes with Two Story Property Description

Welcome to Oldsmar, Florida, a hidden gem nestled in the heart of Pinellas County! This charming city is perfectly situated between the vibrant cities of Tampa and Clearwater, offering residents the best of both worlds: a serene suburban lifestyle with easy access to the bustling urban amenities. Oldsmar is renowned for its beautiful parks, scenic waterfront views along Old Tampa Bay, and a warm, welcoming community spirit that makes it an ideal place to call home.

Oldsmar boasts a variety of housing options, but one of the most sought-after styles is the two-story home. These spacious properties offer an abundance of living space, perfect for families or those who love to entertain. With multiple levels, two-story homes provide an ideal layout that allows for privacy and separation between living and sleeping areas. Imagine hosting gatherings in your expansive living room while guests can enjoy the open-concept kitchen, all while your family enjoys their own retreat upstairs.

Many of Oldsmar's two-story homes come equipped with modern amenities, including gourmet kitchens, luxurious master suites, and beautiful outdoor spaces. Picture yourself sipping coffee on a private balcony, taking in the stunning views of the lush greenery that surrounds you. With a variety of styles and price points, there’s a perfect two-story home waiting for you in Oldsmar.

Experience the charm and convenience of Oldsmar, where your dream two-story home awaits. Discover the perfect blend of community, comfort, and style in this delightful Florida city!

Newest Oldsmar Homes with Two Story Property Description

$229,500
2 Beds ⋅ 3 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
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
$355,000
3 Beds ⋅ 3 Baths ⋅ Tuscany Woods Preserve SubDv. ⋅ 34677 Zip Code
Virtually Staged. Beautiful upscale townhome located in the gated community of Tuscany Woods! This gorgeous property offers 3 bedrooms, two full bathrooms and one half bathroom. Formal entry into large foyer leads to a fabulous open floorplan with lots of natural light, space for entertaining and new luxury vinyl flooring throughout the entire home. The kitchen features a breakfast bar, granite countertops, 42" cabinets and newer stainless steel appliances. 10 foot sliding doors lead out to a screened in patio equipped with a projector with screen and outside the screen enclosure is a second paved patio with space to entertain and garden! Upstairs you'll find the spacious master bedroom with en-suite bathroom featuring gorgeous walk in shower, double vanity, and linen closet. Two more large bedrooms along with a full sized bathroom are also located on the second floor. The laundry area with lots of storage space is on the second floor for your convenience! This community is conveniently located close to beaches, parks, Tampa International Airport, restaurants, shopping and more!

1504 Merlot Court, Oldsmar
$409,500
3 Beds ⋅ 2 Baths ⋅ Heatherwood Unit One Condo SubDv. ⋅ 34677 Zip Code
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 epoxy garage floor, remote blinds, and light fixtures. 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!

Oldsmar
$450,000
3 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code
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. Perfectly positioned between Hillsborough and Pinellas Counties, this exceptional location offers convenient access to Tampa International Airport, St. Pete-Clearwater International Airport, downtown Tampa, St. Petersburg, award-winning Gulf beaches, waterfront dining, shopping, entertainment, 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. Experience waterfront living at its finest. 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
$599,000
4 Beds ⋅ 3 Baths ⋅ Eastlake Oaks Ph 4 SubDv. ⋅ 34677 Zip Code
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
$299,900
2 Beds ⋅ 2 Baths ⋅ St Andrews Condo SubDv. ⋅ 34677 Zip Code
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
$437,500
3 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code
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
$787,000
3 Beds ⋅ 4 Baths ⋅ Wellington Estates SubDv. ⋅ 34677 Zip Code
Welcome to luxury living in the highly sought-after Wellington Estates community of Oldsmar. This stunning ENERGY STAR® certified residence offers over 3,000 square feet of thoughtfully designed living space featuring 3 bedrooms, a private den/office, 3.5 bathrooms, and an expansive bonus room that can easily serve as a media room, game room, home gym, or fourth bedroom. The home also includes a spacious 3-car garage and a resort-style outdoor living area. A dramatic two-story foyer with a designer crystal chandelier sets the tone upon entry. The open-concept floor plan showcases soaring ceilings, elegant crown molding, plantation shutters, and abundant natural light throughout. The gourmet kitchen is the centerpiece of the home, featuring rich espresso cabinetry, quartz countertops, stainless steel appliances, double ovens, a large center island, and a spacious dining area that seamlessly connects to the great room—perfect for entertaining. The spacious primary suite offers a luxurious retreat with a custom walk-in closet and spa-inspired bath complete with dual vanities, a soaking tub, and a walk-in shower. Upstairs, the oversized bonus room provides exceptional flexibility for today's lifestyle needs while the additional bedrooms offer comfort and privacy for family and guests. Step outside to your private backyard oasis featuring a screened-in pool with tranquil rock waterfall feature and an impressive outdoor kitchen complete with granite countertops, built-in grill, refrigerator, and ample prep space—ideal for year-round Florida entertaining. Mature landscaping and privacy hedges create a peaceful setting for relaxation and gatherings. Additional highlights include hurricane shutters, reclaimed water irrigation, in-wall pest defense system, abundant storage, and premium finishes throughout. Located just minutes from top-rated schools, shopping, dining, parks, beaches, and Tampa International Airport, this exceptional Wellington Estates home combines luxury, comfort, and convenience in one remarkable package.

743 Wellington Court, Oldsmar
$585,000
3 Beds ⋅ 3 Baths ⋅ Kingsmill SubDv. ⋅ 34677 Zip Code
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
$2,699,000
5 Beds ⋅ 4 Baths ⋅ Country Club Add To Oldsmar Rev SubDv. ⋅ 34677 Zip Code
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
$316,000
3 Beds ⋅ 3 Baths ⋅ Sun Ketch Twnhms At Cypress Lakes SubDv. ⋅ 34677 Zip Code
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
$339,900
3 Beds ⋅ 3 Baths ⋅ Tuscany Woods South SubDv. ⋅ 34677 Zip Code
HERE IT IS! Located in the highly desirable Tuscany Woods community in Oldsmar, this impeccably maintained 3-bedroom, 2.5-bath townhome offers the perfect combination of comfort, convenience, and pride of ownership. Lovingly cared for by the original owner, this beautifully maintained home is truly move-in ready. Step inside to find fresh interior paint, like-new carpet, elegant crown molding downstairs, and custom trimmed windows throughout. The beautifully appointed kitchen features granite countertops, wood cabinetry, stainless steel appliances, and a stylish backsplash, creating the perfect blend of functionality and design. The nicely appointed floor plan features spacious living areas and a screened-in back porch overlooking a small yard — perfect for relaxing or entertaining. Every detail of this home reflects immaculate condition and thoughtful upkeep. Major updates include an HVAC system replaced in 2022, offering peace of mind for years to come. Located in a gated community with no flood insurance required, the HOA provides exceptional value by including water, sewer, trash, roof maintenance, exterior paint, lawn care, and landscaping. Situated within an A-rated school district and just minutes from top dining, shopping, Tampa International Airport, and the world-renowned Gulf beaches, Oldsmar continues to be one of the Tampa Bay area’s most sought-after locations. Don’t miss this rare opportunity to own a meticulously maintained home in a prime location!

606 Cabernet Way, Oldsmar
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