Oldsmar Homes with Playground Community Features

Oldsmar Homes with Playground Community Features

Welcome to Oldsmar, Florida, a hidden gem nestled in the heart of Pinellas County. Known for its charming small-town atmosphere and vibrant community spirit, Oldsmar offers residents a unique blend of suburban tranquility and access to urban amenities. With its picturesque parks, beautiful waterfront views along Old Tampa Bay, and a variety of recreational activities, this city is perfect for families, retirees, and everyone in between.

One of Oldsmar's standout features is its family-friendly neighborhoods, particularly those with playground community features. Imagine living just steps away from a well-equipped playground where your children can laugh, play, and make lifelong friends. These communities are designed to foster connections among families, providing safe spaces for kids to explore and enjoy the outdoors.

In addition to playgrounds, Oldsmar boasts an array of amenities, including scenic walking trails, sports facilities, and community events that bring neighbors together. The city’s commitment to maintaining green spaces and recreational areas ensures that residents can enjoy a healthy and active lifestyle year-round.

Oldsmar's convenient location also means you’re just a short drive away from the beautiful Gulf Coast beaches, vibrant shopping districts, and cultural attractions of nearby cities like Tampa and St. Petersburg. Whether you’re looking for a cozy single-family home or a spacious townhouse, Oldsmar’s real estate market offers a variety of options to fit your needs.

Discover the charm of Oldsmar today and find your perfect home in this welcoming community where family and fun come first!

Newest Oldsmar Homes with Playground Community Features

3 Beds ⋅ 3 Baths ⋅ TB8545646 MLS ⋅ 0000 BLDG.

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

3 Beds ⋅ 3 Baths ⋅ TB8541656 MLS

HUGE PRICE IMPROVEMENT - WATERVIEWS from All 3 Floors, This UPDATED 3Bed 3Bath townhome is situated in the exclusive gated community of SEASIDE ESTATES in picturesque and historic Oldsmar. Nestled within a Townhome Complex of 67 units, this particular unit stands out as truly unique. The magnificent sunsets are breathtaking. The kitchen has STONE COUNTERTOPS, STAINLESS STEEL APPLIANCES, and offers ease with the CENTRAL VACUUM SYSTEM. Additional highlights include custom-built shelving in both His and Her Primary Closets. The primary suite, located on the third level, boasts a generously sized UPDATED BATHROOMS. The spacious floor plan ensures ample natural light and stunning water views. Enjoy the Florida lifestyle in this golf cart-friendly community, offering amenities such as a swimming pool, Jacuzzi and tennis/pickleball courts. The dock area provides good fishing opportunities, and the residence is only a few minutes away from waterfront public parks, shopping, restaurants, and various recreational facilities. The community hosts more than 20 events annually, with monthly dinners strategically planned around the scenic Tampa Bay. Minutes from downtown Oldsmar and Safety Harbor which offer a variety of restaurants, nightlife, street and music festivals, walking and biking trails, kayaking, This complex is PET FRIENDLY. 20 minutes to Tampa Airport and 30 minutes to downtown Clearwater and world-famous Clearwater Beach, 20 min to Caladesi State Park and the pristine Honeymoon Island.

129 Brent Circle, Oldsmar

3 Beds ⋅ 2 Baths ⋅ TB8543834 MLS

MOVE-IN READY in the gated Bay Arbor community of Oldsmar! This beautifully updated 3-bedroom, 2-bath home is ready for its new owners. Major improvements have already been taken care of, including a brand-new roof, screened patio and fresh interior and exterior paint, allowing you to move in and enjoy from day one. The desirable split-bedroom floor plan offers privacy and an easy flow for everyday living. The open kitchen and family room combination creates a welcoming central gathering space, while the spacious primary suite offers a separate office or sitting area, providing the flexibility for a home office, reading room, or private retreat. The primary bath features dual vanities, a separate shower, and a relaxing Jacuzzi tub. Step outside to the screened-in patio and enjoy peaceful conservation views in a private backyard setting. With no rear neighbors, this is a wonderful place to unwind while enjoying the Florida outdoors. Additional features include an inside laundry room with washer and dryer included, a two-car garage, and plenty of storage. Located within the gated Bay Arbor community, residents enjoy access to a community pool and playground along with beautifully maintained neighborhood grounds. The Oldsmar location offers convenient access to shopping, restaurants, parks, recreation, Tampa International Airport, and major roadways, with easy access to both Pinellas and Hillsborough County. A well-maintained home, a desirable gated community, a peaceful conservation setting, and the big-ticket updates already completed—this one is truly ready for its next chapter.

353 Bay Arbor Boulevard, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8544496 MLS ⋅ Sabal Ct #F BLDG.

RARE FIRST-FLOOR, FULLY REMODELED 2 BED / 2 BATH CONDO IN OLDSMAR, PRICED TO STAND OUT. No stairs and no renovation project waiting for you. This move-in-ready 915 sq. ft. condo has been thoughtfully updated throughout with wood-look flooring, fresh neutral finishes and a bright, open living and dining area that opens directly to a private covered patio. The updated kitchen features shaker-style cabinetry with plenty of storage, quartz countertops, stainless steel appliances, modern hardware and a decorative tile backsplash. The spacious primary suite includes a large walk-in closet and updated ensuite bath with a tiled walk-in shower. The second bedroom is generously sized with excellent closet space, and the second full bath has also been updated with modern tile and a tub/shower combination. An interior laundry area with stacked washer and dryer adds another convenience rarely found at this price point. Gardens of Forest Lakes offers community amenities including a pool, tennis and basketball courts, playground, park and fishing dock, with convenient access to shopping, dining, parks, Tampa, Clearwater, Gulf beaches and Tampa International Airport. First floor, fully updated, two full baths, interior laundry and competitively priced within the community. This one is ready for its next owner.

133 Sabal Court Unit F, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8536224 MLS ⋅ 17 BLDG.

MOVE-IN READY FIRST-FLOOR, 2-BEDROOM, 2-BATH CONDO with BOTH BATHROOMS COMPLETELY REMODELED IN 2026, a BRAND-NEW WATER HEATER (AUGUST 2026), NEW AC (2021), NEW ELECTRICAL PANEL (2024) and an extensive list of recent improvements! Located in The Gardens of Forest Lakes, this light and bright ground-floor residence offers comfortable, low-maintenance living with no stairs and a peaceful setting surrounded by mature landscaping and expansive green space. Step inside to a freshly painted interior with tile flooring throughout, spacious living and dining areas, and sliding glass doors that open directly to the covered patio and lawn beyond. The kitchen offers abundant cabinetry, generous counter space, a breakfast/pass-through bar and a new microwave installed in May 2026. Both bathrooms have been completely renovated in 2026, including new insulation and drywall. The primary bath showcases a stylish new vanity and beautifully tiled walk-in shower, while the second bath features a new vanity and tub/shower combination. Both bedrooms are generously sized with ample closet space, and an interior laundry area adds everyday convenience. Additional 2026 improvements include new Sherwin-Williams paint throughout the entire condo including walls, ceilings, trim and doors, serviced windows and sliding doors with new locks, screens and sash caps, new closet doors, new window blinds and sliding-door verticals, new ceiling A/C vent covers, new hallway linen closet shelving, and new switch and outlet plate covers. Beyond the condo, enjoy an impressive array of community amenities in a scenic lakefront recreational setting. Forest Lakes offers a large community swimming pool and spa, tennis courts, basketball, racquetball/handball courts, playground, picnic and grilling areas, and a waterfront dock overlooking the lake. Mature trees, tropical landscaping and generous green spaces create an inviting setting throughout the community. With extensive recent improvements already completed, first-floor convenience and outstanding recreational amenities, this Oldsmar condo offers an exceptional opportunity for a primary residence, seasonal getaway, low-maintenance Florida home or great rental income opportunity. Great location close to Beaches, Parks, and Tampa International airport. Schedule your private showing today!

123 Loblolly Court Unit A, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8536581 MLS ⋅ 2 BLDG.

Welcome to this beautiful 2-bedroom, 2-bathroom ground-floor condo in the highly sought-after East Lake Woodlands community. Built in 1979 with durable masonry construction and a slab foundation, this charming residence offers the perfect blend of comfort, character, and convenience. Enjoy peaceful pond views from the rear of the home while being surrounded by the outstanding amenities this master-planned community has to offer, including golf courses, nature trails, swimming pools, and a clubhouse. Ideally located between Hillsborough and Pinellas Counties, you'll have easy access to an incredible selection of shopping, dining, entertainment, and Gulf Coast attractions. Inside, timeless elegance shines through with beautiful oak flooring, a cozy wood-burning fireplace, and a convenient pass-through from the kitchen to the living area, creating an open and inviting space for everyday living or entertaining. The in-unit utility closet includes a washer and dryer for added convenience, while the generous closet space provides exceptional storage rarely found in condominium living. A covered parking space located directly in front of the unit makes unloading groceries and staying dry during Florida's afternoon showers a breeze. Whether you're looking for a year-round residence, a seasonal retreat, or an investment opportunity, this exceptional condo offers the best of maintenance-free living in one of the area's most desirable gated communities. Come experience the beauty and lifestyle of East Lake Woodlands and make 205 Martha Lane your new home!

205 Martha Lane Unit 205, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8534748 MLS

Investor special with exceptional upside! This concrete block 2-bedroom, 2-bath, 2-car garage home is priced to sell and offers outstanding renovation potential. Situated on a nicely sized lot with beautiful lake views and no rear neighbors, the fully fenced backyard has plenty of room for a pool. The home has an updated electrical panel. The HVAC system was updated in 2019. The roof was last replaced in 2009. The office provides approximately 270 additional square feet beyond the heated living area, offering flexible space for a home office, hobby room, or future expansion. (The second bathroom is located in the garage.) Enjoy a great central location just a short walk to Sheffield Park and Harbor Palms Nature Park, featuring walking trails, a boardwalk, fishing pier, and kayak launch. No HOA and convenient access to Tampa, St. Petersburg, Gulf beaches, shopping, dining, and Tampa International Airport. Cash offers only. Property is being sold As Is with no repairs.

704 Lemonwood Drive, Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8514567 MLS ⋅ 133 BLDG.

Virtually Staged. CASH PURCHASE ONLY. Perfect Rental/Investment Property Tucked into the trees of The Gardens of Forest Lakes, this 915 sq ft second-floor 2-bedroom, 2-bath condo pairs an open-concept living and dining layout with a private deck overlooking a quiet, wooded backdrop. Laminate flooring runs throughout for a clean, low-maintenance feel, and all appliances are included for a true move-in or rent-ready opportunity. The monthly fee covers trash, exterior maintenance, exterior insurance plus access to Forest Lakes community amenities including the pool, tennis and racquetball courts, park, and playground, all set among mature landscaping. One assigned parking space conveys. With a recent rent of $1,695/month, this is a strong fit for investors or buyers seeking an affordable Pinellas County footprint. Pet-friendly with HOA approval. Ideally positioned in Oldsmar, the city with more parks per square mile than any other in Florida, with Mobbly Bayou Wilderness Preserve, Mobbly Beach Park, and the 10-mile Oldsmar Trail nearby, plus easy reach to Tampa, Clearwater, St. Pete, Gulf beaches, dining, and shopping. A smart blend of nature, convenience, and value. Note: second-floor walk-up; no elevator.

133 Sabal Court Unit G, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8513394 MLS ⋅ 120 BLDG.

Come and tour this cozy 3 bedroom, 3 bathroom waterfront townhouse and you will quickly see how easy it is to embrace the lifestyle that makes Florida living so desirable. This 1834 sq ft, 3 level townhouse delivers comfortable maintenance free living in a space where you can be in for years to come. Soak in endless water views as you sip your morning coffee or unwind with a good book, from 2 balconies to choose from. Sky lights brighten up multiple spaces in the home capturing natural night. Enjoy a slice of your own paradise with this sensible buy!” Not only does it give you endless water views, private tennis courts, playground, community pool area, this gated community also Includes your own deeded dock with a new seawall. The garage can fit up to 3 vehicles providing abundant storage. NO OUTSTANDING ASSESSMENTS.

117 Brent Circle, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8510265 MLS

One or more photo(s) has been virtually staged. Seller offering $5,000 towards Buyer closing costs and/or pre-paids. 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

2 Beds ⋅ 2 Baths ⋅ TB8509741 MLS ⋅ 12 BLDG.

Welcome to this beautifully maintained condo in the heart of desirable East Lake Woodlands! Offering a spacious and inviting layout, this residence provides the perfect blend of comfort, convenience, and relaxed Florida living. LOW HOAs and fantastic amenities that include a full size pool, a kiddy pool, tennis/basketball/raquetball courts, and a playground. This light and bright unit features an open floor plan with generous living and dining areas, perfect for entertaining or relaxing at home. The kitchen offers ample cabinet and counter space with a functional layout ideal for everyday living. The primary suite includes a private bath and spacious closet space, while additional bedrooms provide flexibility for guests, family, or a home office. Great location near Honeymoon Island, RE Olds Park, Tampa International Airport, bike and walking trails, dog parks, shopping, restaurants, live theater, museums, and activities in downtown St. Pete and Tampa.

131 Sabal Court Unit E, Oldsmar

4 Beds ⋅ 3 Baths ⋅ TB8485835 MLS

One or more photo(s) has been virtually staged. PRICE ADJUSTMENT August 30th $33k below Zestimate. Gorgeous water views of Old Tampa Bay from this custom-built, original-owner home in a prime Oldsmar location, directly across from popular R.E. Olds Park with its amphitheater, fishing pier, playgrounds, sand volleyball and annual fireworks you can enjoy from your front porch. The resort-style backyard features a large in ground pool with spa, kiddie pool, spillover fountain and fiberoptic lighting, all within a screened enclosure with covered area for dining and parties would cost well over $100k to install today. A spacious concrete pad doubles as a basketball court and offers room to store a boat or add a shed, plus parking for 2 cars under carports and a deep driveway that has accommodated 10+ vehicles, with overflow available at the park. Upstairs, the main living level welcomes you through double hurricane-rated doors to beautiful Brazilian hand-scraped wood floors, abundant windows, and an eat-in kitchen with granite counters and arched opening to the living room, along with a formal dining room. An office or bedroom on this level opens via sliding glass doors to a balcony overlooking the pool, and a convenient half bath completes the floor. The bedroom level begins with a newer washer/dryer closet for easy access to all bedrooms. The primary suite offers stunning water views from sliders, the third-level deck and multiple windows, and its ensuite bath was updated in 2017 with new cabinetry, tile and quartz counters; the second full bath was also updated. Major updates include a 2016 roof and 2023 A/C, making this well-maintained home ideal for both everyday living and large gatherings.

402 Shore Drive W, Oldsmar

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