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 vibe and vibrant community spirit, Oldsmar boasts a perfect blend of tranquility and convenience. With its close proximity to the stunning Gulf Coast beaches and a variety of outdoor recreational activities, residents enjoy a lifestyle that celebrates both relaxation and adventure.

Oldsmar is home to a diverse range of amenities, including parks, shopping centers, and dining options that cater to every palate. The city features picturesque waterfront views along the Old Tampa Bay, offering residents the opportunity to partake in boating, fishing, and scenic strolls along the waterfront parks. Families will appreciate the well-maintained schools and community events that foster a strong sense of belonging.

One of the standout features of homes in Oldsmar is the availability of communities with playgrounds, making it an ideal choice for families. These thoughtfully designed neighborhoods not only provide safe and engaging spaces for children to play but also encourage social interactions among neighbors. Picture your little ones laughing and playing in the sun while you enjoy a leisurely afternoon with friends at the nearby picnic areas.

Whether you’re a first-time homebuyer or looking to settle down in a family-friendly environment, Oldsmar offers a range of housing options that cater to various lifestyles. With its warm weather, welcoming community, and fantastic amenities, Oldsmar is the perfect place to call home. Come discover the charm and convenience of this delightful city in sunny Florida!

Newest Oldsmar Homes with Playground Community Features

131 Brent Circle, Oldsmar
$849,900
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
This rare, customized end unit townhome is located on Old Tampa Bay in Oldsmar in the sought after gated community of Seaside Estates. Enjoy breathtaking open water views from any of the floors largely due to the abundance of windows and 3 generous sized patios/decks. Relaxing will come naturally as you gaze out over the green space, seawall and open water. Home features 1834 sf and 3 bedrooms, 3 baths. There are 2 outside parking spaces within a few feet of the attractive entry to the unit. Upon entering the bottom floor you have a foyer and to the left an oversized 2+ car tandem parking garage with an abundance of storage and rear covered patio. Garage also has a vented portable air conditioner and a dehumidifier creating a perfect storage and work area. The ground entry foyer has stairs leading up to the main living area floor where you are greeted with great light from the multi windows and large deck/patio. It is truly a breathtaking view looking out on Old Tampa Bay. This floor features a living room, dining room, updated kitchen (2019), one bedroom with a built-in murphy bed plus desk and a full bath. Ascending one more floor, there is the master suite with sliders leading to a spacious deck, a second en-suite bedroom with its private full bath. There is also a laundry area with double doors for easy access and stackable washer/dryer. Throughout the wooden floors are beautiful with some tile in the wet areas. Multiple outdoor spaces including the ground floor patio plus oversized patios/decks as one on each floor really expand the living space so you can enjoy the Florida lifestyle throughout this open unit. Don't let the multi-stories be an issue as this unit boasts an ELEVATOR installed 2025 to help you move yourself and your belongs easily throughout. As an added bonus, this unit comes with a DEEDED BOAT SLIP located behind the unit at the mouth of the channel. So whether you prefer fishing from the seawall, inshore fishing or shooting out in the Gulf for a little offshore fishing or just pleasure boating maybe to local restaurants/bars such as close by Jack Willie's, you're ready to go! While feeling very private, this unit offers it all . . . privacy yet close to shopping and restaurants for your daily needs.

131 Brent Circle, Oldsmar
1633 Shady Oaks Drive, Oldsmar
$560,000
3 Beds ⋅ 3 Baths ⋅ Eastlake Oaks Ph 3 SubDv. ⋅ 34677 Zip Code
Pool, heated spa, and a 3-car garage in East Lake Oaks. This 3-bedroom, 2.5-bath Oldsmar home pairs a screened outdoor setup with solid updates: roof 2017, AC 2021, and vinyl fence 2021. The two-story layout opens with vaulted ceilings over a combined living and dining room. The kitchen features wood cabinetry, stainless steel appliances, and an eat-in area, and it opens to the family room for easy everyday flow. The remodeled primary bath includes dual sinks, a standalone tub, and a separate shower. Out back, the screened lanai offers covered seating, the heated spa, and the pool, all within a vinyl-fenced yard for added privacy. Community amenities include a pool, playground, and ponds. Harbor Palms Nature Park, Estuary Preserve, and Sheffield Park are nearby for bike trails, disc golf, and tennis. Centrally located near shopping, restaurants, and theaters, with easy drives to downtown Safety Harbor, downtown Dunedin, Tampa, the airports, and Clearwater Beach.

1633 Shady Oaks Drive, Oldsmar
116 Brent Circle, Oldsmar
$405,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
Welcome to Seaside Estates! This is a 3 bedroom, 3 bathroom townhome on the canal with your own private dock. If you’ve been looking for a place to keep your jet ski or kayak right outside your door, this is it. The entry level gives you direct access to the garage, where sliders on the back open right out to the docks. Load up your gear and be on the water in minutes. The second floor features a large living room that opens onto a balcony overlooking the canal. This level also includes the kitchen, a full bathroom, and a bedroom, a great setup for guests or a home office. Head up to the third floor to find two more bedrooms, each with its own ensuite bathroom. The owner’s suite has a private balcony with views of the canal, the perfect spot for morning coffee or evening sunsets. Laundry is conveniently located on this level, right where you need it. This home is ready for a new owner to make it their own. With some fresh paint, new carpet, and your personal touches, you can build equity and create the waterfront retreat you’ve been dreaming of. Opportunities with private dock access like this don’t come along often. Call today to schedule your showing!

116 Brent Circle, Oldsmar
600 Shore Drive E, Oldsmar
$899,000
3 Beds ⋅ 4 Baths ⋅ Tampashores Bay Sec SubDv. ⋅ 34677 Zip Code
Half an acre of direct waterfront on Old Tampa Bay with 108 feet of frontage and a 203-foot-deep lot on Shore Drive E, Oldsmar's most sought-after waterfront street. Open bay views west across the water, a second-floor balcony that showcases spectacular sunset views of Tampa Bay, and a screened pool and spa on a paver deck facing the bay. The existing 1962 two-story block and stucco home, 2,454 sf with 4 full baths, tile roof, and fireplace, flooded in 2024 and has been professionally remediated, with lower-level drywall removed to the flood line. Two paths forward: build new on one of the larger waterfront parcels on the street, or keep and lift. Unique to this property: the seller has been approved for Elevate Florida, the state's FEMA-funded residential elevation program, with an estimated $402,000 in federal funding toward raising the existing home above the floodplain (Structure Elevation), along with adding an additional 800 sqft of under-roof living space. Subject to an owner cost share per the FDEM financial packet. Per the Florida Division of Emergency Management, a new owner may elect to continue the approved project after closing, subject to completing program documentation and assuming program obligations, including a deed restriction requiring NFIP flood insurance for the life of the elevated structure. All figures are estimates from the FDEM financial packet and are subject to change. Buyer to verify all program terms directly with FDEM. No HOA, no CDD. Walkable to Mobbly Bayou Beach Park, RE Olds Park and Veterans Park, and the Oldsmar boat ramp. Minutes to Tampa International Airport and the Gulf beaches. Cash or construction financing. Seller's flood disclosure, remediation documentation, FDEM correspondence, and survey available in attachments.

600 Shore Drive E, Oldsmar
4798 Augusta Avenue, Oldsmar
$565,000
4 Beds ⋅ 3 Baths ⋅ Worthington SubDv. ⋅ 34677 Zip Code
Welcome to 4798 Augusta Ave, located within the desirable East Lake Woodlands community! Enjoy the peace and tranquility of a quiet, serene street where local wildlife sightings add to the charm of the neighborhood. Convenient resident entry provides quick access in and out of the community, making everyday travel a breeze. Inside, luxury vinyl plank flooring installed in 2023 offers a fresh, cohesive look throughout the home. The functioning fireplace adds warmth and character, while the whole-house water softener provides an added layer of everyday comfort. Major updates include a 2015 roof, 2019 A/C, impact-rated sliding glass doors installed in 2021, a rescreened lanai in 2021, and exterior paint completed in 2019 and interior painted in 2024. The home has never flooded. The community also features Ardea Country Club, where members can enjoy access to two 18-hole championship golf courses, a swimming pool, hard and soft tennis courts, pickleball courts, a playground, a gym, and Heron’s Bar and Grille With thoughtful updates, desirable community amenities, and a peaceful setting, this home is ready for its next owner to make it their own!

4798 Augusta Avenue, Oldsmar
1750 Split Fork Drive, Oldsmar
$615,000
4 Beds ⋅ 3 Baths ⋅ Eastlake Oaks Ph 1 SubDv. ⋅ 34677 Zip Code
Virtually Staged. Welcome to this spacious and well-maintained **4-bedroom, 3-bath Oldsmar home offering 2,460 square feet of living space**, a great layout, and plenty of room to spread out. As soon as you enter, the **high vaulted ceilings** create an open, airy feel and showcase the generous living areas throughout the home. Situated on a **larger lot in a quiet neighborhood**, the home also features an approximately **14' x 17' rear addition**, providing valuable extra space and flexibility. This area can function as a **bonus room or 4th bedroom and has its own mini-split system**, making it comfortable and versatile for guests, a home office, playroom, gym, or additional living space. Step outside to the screened pool and enjoy a **gorgeous water view**, creating a peaceful Florida setting that’s perfect for relaxing or entertaining. The home has been **very well kept and maintained**, with additional highlights including a **2018 roof** and a functional floor plan that makes great use of the space. This is a great opportunity to own a spacious home with a pool, water view, larger lot, and flexible living space in a desirable Oldsmar location.

1750 Split Fork Drive, Oldsmar
129 Camphor Circle Unit C, Oldsmar
$155,000
2 Beds ⋅ 2 Baths ⋅ Gardens Of Forest Lakes Condo The SubDv. ⋅ 34677 Zip Code
Welcome to The Gardens of Forest Lakes, one of Oldsmar’s well-kept secret communities. This 2 bedroom 2 bathroom condo is a true move-in ready home. The features and amenities are apparent upon entering this well-decorated unit. The newer luxury vinyl flooring set the stage for a great showing. The living room/dining room combination offers an open & spacious area you can call home. The kitchen was updated to include custom wood cabinets with hydraulic drawers; led area lighting; newer appliances including a brand new refrigerator & a double oven; brand new hot water heater (5/26); deep double steel sink; tile backsplash; granite-looking Formica countertops; Both bathrooms were updated to include wood-like tile; the guest bathroom offers a deep soaker tub; Enjoy the beautiful pond view from both bedrooms and the private balcony; An inside laundry room with a newer washer/dryer combo for your convenience; The master bedroom offers a walk-in closet; The balcony has a storage room for your extra stuff; The community has a recreation center that includes a swimming pool, tennis & racquetball courts, a playground and a fishing pier. Close to shopping, dining, entertainment and more. Schedule your private showing today. You’ll be glad you did.

129 Camphor Circle Unit C, Oldsmar
129 Brent Circle, Oldsmar
$460,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
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
353 Bay Arbor Boulevard, Oldsmar
$550,000
3 Beds ⋅ 2 Baths ⋅ Bay Arbor SubDv. ⋅ 34677 Zip Code
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
133 Sabal Court Unit F, Oldsmar
$119,500
2 Beds ⋅ 2 Baths ⋅ Gardens Of Forest Lakes Condo The SubDv. ⋅ 34677 Zip Code
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
123 Loblolly Court Unit A, Oldsmar
$119,900
2 Beds ⋅ 2 Baths ⋅ Gardens Of Forest Lakes Condo The SubDv. ⋅ 34677 Zip Code
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
205 Martha Lane Unit 205, Oldsmar
$179,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
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
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