Oldsmar Homes with Attached Property Description

Oldsmar Homes with Attached Property Description

Welcome to Oldsmar, Florida – a hidden gem nestled in the heart of Pinellas County that perfectly balances small-town charm with modern conveniences. With its picturesque landscapes, vibrant community life, and proximity to the stunning Gulf Coast, Oldsmar is a place where you can truly feel at home.

Oldsmar boasts a rich history, founded in the early 1900s and named after its founder, a visionary who saw the potential of this beautiful area. Today, it offers a unique blend of outdoor recreation, cultural attractions, and family-friendly amenities. Enjoy scenic walks along the waterfront at Oldsmar's beautiful parks, or take advantage of the numerous biking trails that wind through the lush greenery. The city's commitment to preserving its natural beauty is evident in its well-maintained parks and open spaces, making it a paradise for nature lovers.

When it comes to real estate, Oldsmar features a diverse array of homes, many of which come with attached properties that provide the perfect opportunity for families or those seeking a bit more space. These homes often feature spacious layouts, modern amenities, and beautifully landscaped yards, making them ideal for entertaining or simply enjoying quiet evenings at home. With a strong sense of community and excellent schools, Oldsmar is a perfect choice for families looking to settle down.

In addition, residents enjoy easy access to nearby cities like Tampa and St. Petersburg, ensuring that work and play are always within reach. Whether you're searching for a cozy family home or a spacious retreat, Oldsmar is ready to welcome you with open arms. Come discover your dream home in this delightful Florida town!

Newest Oldsmar Homes with Attached Property Description

3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code

THE KITCHEN SETS THIS ONE APART. Step into a brighter, more open 3-bedroom, 3-bathroom townhome with over 1,800 square feet in the gated waterfront community of Seaside Estates. Bamboo flooring, a fireplace, high ceilings, and a private balcony create a light-filled, open-concept main level. The kitchen was extended 3 feet and the original dropped ceiling was removed, so the space feels tall and open to the living room -- a difference most of the 67 units in this community still don’t have. Quartz counters, new white cabinetry, stainless appliances, and a built-in pantry finish the update. A flexible bedroom on this level works as an office or guest suite. Upstairs, the primary suite offers soaring vaulted ceilings, dual walk-in closets, skylights, its own balcony, and a spacious ensuite, with laundry and a third bedroom with an ensuite bath on the same level. The oversized tandem garage adds storage and sliding-door access to a patio and green space. This building sits closer to the tennis court and main entrance, and farther from the pool noise. Residents share a resort-style pool/spa, tennis, boardwalk, and a floating dock for kayaks and paddleboards, with slips and boat lifts typically available to rent. Inclusive HOA fees cover the roof (2017), water, sewer, trash, and interior fire sprinklers. Just steps from R.E. Olds Park, a 15-acre waterfront park with the city pier, playgrounds, trails, beach volleyball and more, plus convenient access to Gulf Coast beaches, Tampa International Airport, Clearwater, and Tampa/St. Pete. Schedule your showing today!

106 Brent Circle, Oldsmar

4 Beds ⋅ 3 Baths ⋅ Cross Pointe SubDv. ⋅ 34677 Zip Code

Virtually Staged. Welcome to an exceptional 2,736-square-foot luxury home nestled within Cross Pointe, a gated community inside the prestigious guard gated golf community of East Lake Woodlands . Offering 4 bedrooms, 3 baths, a spacious 2-car garage,with workbench area. and bonus space. This beautifully appointed residence blends elegant finishes, thoughtful design, and exceptional outdoor living. Pool access & views from almost every room. Desirable split-bedroom floor plan features soaring ceilings and travertine flooring complemented by engineered hardwood & tile floors. The updated gourmet kitchen is designed for both everyday living and entertaining, featuring Bosch and Frigidaire appliances, (Range has induction cooktop & convection/air fry oven) quartz tops, crisp white cabinetry, and a striking navy island. Breakfast area overlooking pool. The family room offers a warm wood-burning fireplace (updated 2020) and a sophisticated navy wine bar, creating an inviting gathering space. Spacious primary suite includes a comfortable sitting area and sliders that open directly to the screened porch, offering beautiful views of the private pool and backyard . Walk-in closet with organizers. Primary bath has soaking tub, large marble shower, private water closet & dual sink vanities. 3 guest bedrooms, with one having an ensuite bath also providing convenient access to the pool area—perfect for effortless poolside living. Bonus/Flex room with its own A/C (2026) is perfect for an office, hobby room, studio, gym, etc. Outdoor living is truly exceptional. The screened rear porch features paver flooring and overlooks the Saltwater PebbleTec pool , complete with Caribbean blue tile, a charming, soothing waterfall and gazebo. Pool pump & new salt system (2025). An expanded paver patio (2025) extends into the private backyard, providing ample space for entertaining, relaxing, and enjoying the peaceful surroundings. Many updates include tile roof (2019), HVAC (2017), Paver patio (2022), Kitchen updated (2020) with professional kitchen cabinet refinishing (2026), Bosch refrigerator (2025), Frigidaire appliances (2026). All ceiling fans updated (2024 & 2025). Newly textured ceilings (2022), modern lighting. With its luxurious finishes, spacious layout, updated kitchen, resort-style pool, and prime location within two prestigious gated communities, this home offers an exceptional Florida lifestyle with privacy, comfort, and elegance at every turn. Centrally located to Tampa International and St . Pete/Clearwater Airport, award winning beaches, boating and fishing, professional sporting events, historic Dunedin and Safety Harbor, Pinellas and Duke Energy Bike Trails, restaurants, shopping, and hospitals. East Lake Woodlands is a golf community with an optional membership available to the nationally renowned ELW Country Club, featuring outstanding amenities including two championship golf courses, sixteen tennis courts, pickleball, fully-equipped fitness center, lap & freeform pools, splash pad, dining, full social calendar/club, and is also part of ClubCorp/Invited with reciprocal rights to 300+ clubs. Low HOA and NO flood insurance required. A fantastic value! Call today for your private tour!

1723 Captiva Drive, Oldsmar

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Woodlake Run SubDv. ⋅ 34677 Zip Code

PRICE REDUCED!! Call to schedule your private showing of this beautifully furnished 2-bedroom, 2-bath upstairs condominium in the highly desirable gated community of East Lake Woodlands. TOTALLY TURNKEY if you desire Perfectly positioned in a quiet setting, this light-filled home welcomes you with soaring vaulted ceilings and an abundance of natural light streaming through the upper windows, creating a bright and spacious atmosphere you'll love coming home to. Designed for comfortable Florida living, this FULLY FURNISHED condo is move-in ready. Snowbirds and seasonal residents can simply bring their clothes and groceries—everything else is already here, making your Florida getaway effortless. Enjoy refreshing breezes from two private screened patios. Sip your morning coffee as the sun rises or relax in the evening with your favorite beverage while taking in the peaceful surroundings. The screened balcony is accessible from both the spacious living room and the primary bedroom, creating a seamless indoor-outdoor lifestyle. The split-bedroom floor plan offers privacy for both owners and guests. The generous primary suite features a large walk-in closet and a private en-suite bathroom, while the guest bedroom is thoughtfully separated by the guest bath and closets, making it ideal for family and visitors. A convenient laundry closet with a washer and dryer is located on the screened kitchen patio and is easily accessible from both the kitchen and the guest bedroom. East Lake Woodlands is a beautifully maintained 24-hour guard-gated golf community where residents enjoy secure access with resident vehicle passes and a peaceful country club atmosphere. Optional memberships offer golf, tennis, fitness, dining, and social activities. Located at the corner of Tampa Road and East Lake Road, you'll be just minutes from grocery stores, shopping, restaurants, medical facilities, and entertainment, with beautiful Gulf beaches and Tampa International Airport only a short drive away. Whether you're looking for a seasonal retreat or a full-time Florida residence, this exceptional condo offers comfort, convenience, and the carefree lifestyle you've been dreaming about.

124 Woodlake Wynde, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code

Welcome to Gull-Aire Village, one of Pinellas County's most desirable and active 55+ communities! Don't miss this opportunity to own a home in the highly sought-after Gull-Aire Village, where you own the land and enjoy an incredibly affordable HOA fee of just $70 per month. Whether you're looking for a full-time residence, seasonal retreat, or future investment property, this community offers exceptional flexibility with the ability to rent your home after only one year of ownership. Gull-Aire Village is known for its vibrant atmosphere, active social calendar, and unbeatable location. Residents enjoy the convenience of being within walking distance to shopping, entertainment, and dining, including AMC Theatres, Bealls, Marshalls, Earth Fare, PetSmart, and Dollar Tree. Nearby restaurants include Shaker & Peel, Craft Street Kitchen, and Eve's Family Restaurant. Additional conveniences such as Westfield Countryside Mall, Walmart, Publix, and Countryside Hospital are just minutes away. Plus, you'll be approximately 20 minutes from the award-winning beaches and natural beauty of Honeymoon Island and Caladesi Island State Park. Pet friendly with one pet allowed of any size. Experience affordable Florida living in a welcoming community that truly has it all. Schedule your private showing today! Cash only for the ease of the seller.

410 Dolphin Drive S, Oldsmar

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code

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

4 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code

Welcome to 138 Brent Circle in desirable gated Seaside Estates—an exceptional opportunity to own the largest corner townhome in this sought-after waterfront community in Oldsmar. Perfectly positioned to capture panoramic views of Tampa Bay, this residence offers a rare combination of space, scenery, and coastal lifestyle, complete with a private boat slip for easy access to the water. This spacious 4-bedroom, 3-bath home features a thoughtfully designed layout with abundant natural light and comfortable living areas ideal for both everyday living and entertaining. The inviting living room is anchored by a cozy fireplace, creating a warm focal point while showcasing the stunning water views beyond. A second fireplace in the primary bedroom adds an extra layer of comfort and charm, creating a relaxing private retreat. The kitchen offers ample cabinetry and workspace, seamlessly connecting to the dining and living areas for a functional, open feel. Each bedroom provides flexibility for a variety of living arrangements, while the three full bathrooms add convenience and comfort. An oversized garage delivers generous storage and parking space—an added benefit rarely found in townhome living. As a corner unit, the home enjoys enhanced privacy and additional natural light. Step outside and take in the tranquil waterfront setting, where you can relax, entertain, or set out for a day on Tampa Bay directly from your own boat slip. Conveniently located near parks, shopping, dining, and major roadways, this property offers the perfect blend of peaceful coastal living and everyday accessibility. Don’t miss your chance to own a premier waterfront residence in Seaside Estates—schedule your private showing today.

138 Brent Circle, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code

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. ⋅ 34677 Zip Code

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

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