Oldsmar Homes with True Pool - Private

Oldsmar Homes with True Pool - Private

Welcome to Oldsmar, Florida – a hidden gem nestled in the heart of Pinellas County! Known for its charming small-town atmosphere, Oldsmar offers a delightful blend of suburban tranquility and vibrant community life. With its picturesque parks, scenic waterfront, and a rich history that dates back to the early 1900s, this city is perfect for families, retirees, and everyone in between.

One of the standout features of Oldsmar is its commitment to outdoor living. Residents enjoy easy access to numerous parks, trails, and recreational areas, making it an ideal location for those who appreciate an active lifestyle. The nearby Tampa Bay provides opportunities for boating, fishing, and other water activities that enhance the coastal living experience.

For those searching for their dream home, Oldsmar boasts a variety of properties, including stunning homes with private pools. Imagine stepping into your own backyard oasis, where you can unwind in your True Pool, surrounded by lush landscaping and the soothing sounds of water. These private pools offer not just a place to cool off on those warm Florida days, but also a perfect setting for entertaining friends and family or simply enjoying a quiet evening under the stars.

Whether you're drawn to the vibrant community events, the natural beauty, or the charm of Oldsmar’s neighborhoods, this city has something for everyone. Discover the joys of Oldsmar living and find your perfect home with a True Pool – where relaxation and recreation come together in your personal paradise. Welcome home!

Newest Oldsmar Homes with True Pool - Private

4 Beds ⋅ 3 Baths ⋅ Greenhaven Unit Two SubDv. ⋅ 34677 Zip Code

Homes like this rarely become available in the highly sought-after gated community of East Lake Woods. Completely remodeled and situated on over a quarter acre overlooking a tranquil pond, this exceptional residence offers the perfect blend of luxury, comfort, and functionality. From the moment you arrive, you'll appreciate the expansive driveway, oversized three car garage, and impressive curb appeal. As you approach the grand double-door entrance, soaring 12 foot ceilings immediately set the tone for what awaits inside. Step through the front doors and your eyes are instantly drawn to the breathtaking views of the sparkling pool and peaceful pond beyond. The home has been freshly painted inside and out and showcases new luxury waterproof vinyl plank flooring throughout, creating a seamless, modern aesthetic. Designed with both everyday living and entertaining in mind, the home features a desirable three way split floor plan, offering privacy for family members and guests alike. The spacious primary suite is a true retreat, complete with high ceilings, plantation shutters, and a spa-inspired ensuite bathroom. Relax in the freestanding soaking tub or unwind in the oversized walk-in shower featuring a rainfall showerhead and body jets. The luxurious bath also includes dual vanities, a dedicated makeup station, and an illuminated LED mirror. As you continue into the heart of the home, you'll discover a stunning open-concept kitchen and family room designed to impress. The fully remodeled kitchen features brand-new solid wood soft-close cabinetry, Taj Mahal quartz countertops, a cooktop with pot filler, new stainless steel appliances, and exceptional workspace for the home chef. Adjacent to the kitchen is a bright breakfast nook overlooking the pool, as well as a separate butler's pantry perfect for a coffee bar, beverage station, or additional storage. Entertaining is effortless thanks to the beautifully redesigned wet bar, featuring rich dark cabinetry, ambient lighting, a sink, and a built-in wine refrigerator. Just beyond, the expansive family room provides ample space for gatherings of any size. A beautifully renovated guest bathroom off the kitchen features designer tile, a modern vanity, and an LED mirror. Toward the rear of the home, you'll find two additional spacious bedrooms and another fully remodeled bathroom with dual sinks, LED mirrors, and convenient access to the pool. Step outside to your own private backyard oasis. The oversized screened lanai surrounds the sparkling pool and offers the perfect setting for year-round Florida living. The outdoor kitchen is equally impressive, showcasing stunning Brown Fantasy granite countertops, a new built-in grill, and a beverage refrigerator. The finishing touch? Your very own private putting green. Whether you're practicing your short game, entertaining guests, or simply enjoying the peaceful pond views, this backyard is designed to be enjoyed. Every detail of this remarkable home has been thoughtfully updated, creating a truly move-in-ready opportunity in one of the area's most desirable gated communities. Additionally residents have the opportunity to join the on-site Ardea Country Club, optional memberships provide access to championship golf, tennis, pickleball, a resort style lap pool, state of the art fitness center and dining. Minutes from top rated schools, Tampa International and St. Pete-Clearwater airports, award-winning Gulf beaches, professional sports team and more!

35 Greenhaven Trail, Oldsmar

4 Beds ⋅ 4 Baths ⋅ East Lake Woodlands SubDv. ⋅ 34677 Zip Code

Welcome to this exceptional 4-bedroom, 4-bathroom pool home located on a corner lot within the gated golf community of East Lake Woodlands in Oldsmar. Offering an impressive 3,441 square feet of living space, this beautiful residence combines elegant interiors, flexible living spaces, and a resort-style outdoor setting. Major updates include a 2021 roof, HVAC systems replaced in 2022 and 2023, and a 2022 water heater, providing peace of mind for years to come. A spacious foyer welcomes you into the home, where soaring vaulted ceilings with stunning wood beams and a wood-burning fireplace create a warm and inviting focal point in the living room. Double sliding doors seamlessly connect the indoor living areas to the screened pool and expansive outdoor entertaining spaces, embracing Florida's sought-after indoor-outdoor lifestyle. The thoughtfully designed split floor plan offers privacy and functionality, including a private fourth bedroom with its own en-suite bathroom, perfect for guests or multi-generational living. The spacious bonus room with built-in shelving provides endless possibilities as a home gym, movie theater, studio, game room, or additional living area. The beautifully appointed kitchen is designed for both everyday living and entertaining, featuring quartzite countertops, stainless steel appliances, a double oven, abundant cabinetry, pantry organizers, and a walk-in pantry for exceptional storage. A charming breakfast nook overlooks the pool, while the formal dining room provides an elegant setting for special gatherings. Wood-look tile flooring extends throughout the main living areas, complemented by crown molding throughout the home. The oversized primary suite serves as a luxurious retreat, featuring two large walk-in closets with custom organizers and a spa-inspired en-suite bathroom complete with a soaking tub, walk-in shower, private water closet, and generous vanity space. The updated shared bathroom showcases a modern double-sink vanity with a marble top, an illuminated mirror, and a shower/tub combination. A spacious laundry room with additional cabinetry adds even more convenience. Step outside to your private oasis. The rebuilt pool features all-new equipment and a heater, allowing for year-round enjoyment. The screened lanai offers abundant space for entertaining, including a covered dining area and convenient pool bath with a shower. New tropical landscaping further enhances the home's curb appeal and atmosphere. Residents of East Lake Woodlands enjoy a prime location close to parks, shopping centers, numerous dining options, and highly rated schools. Optional memberships are available at Ardea Country Club, offering access to golf, tennis, fitness facilities, swimming, social events, and more. This remarkable home offers the perfect combination of luxury, space, and lifestyle in one of Oldsmar's most sought-after communities.

475 Holly Hill Road, Oldsmar

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

3 Beds ⋅ 2 Baths ⋅ Harbor Palms-Unit One SubDv. ⋅ 34677 Zip Code

Welcome to one of Oldsmar's hidden gems! This beautifully maintained 3-bedroom, 2-bath pool home is nestled in the highly desirable Harbor Palms neighborhood, offering the perfect combination of location, comfort, and the Florida lifestyle. The bright split-floor plan features premium laminate and tile flooring, a spacious living room with French doors leading to your private backyard oasis, a formal dining room with a picture window, and a beautifully appointed kitchen with granite countertops, wood cabinetry, and stainless-steel appliances, to include a Point of use Reverse Osmosis Water Purification System. The interior laundry room includes the washer, dryer, and ample storage cabinets. The spacious primary suite offers dual walk-in closets and a beautifully updated en-suite bath with quartz countertops, soft-close cabinetry, and a custom-tiled walk-in shower. Step outside to the screened, covered lanai overlooking a sparkling pool with a tranquil waterfall. The pool is equipped with a child safety fence, which is included with the home. The oversized, fully fenced backyard offers plenty of room to entertain, relax, or enjoy Florida's year-round sunshine. Ideally located just a short walk or bike ride to the neighborhood's beloved Sheffield Park, featuring playgrounds. You'll also enjoy being just 25 minutes from Honeymoon Island and Tampa International and St. Pete-Clearwater airports, and only minutes from shopping, dining, and everyday conveniences. Opportunities like this in Oldsmar are rare—don't miss your chance to own this move-in-ready Florida retreat.

416 Maplewood Drive, Oldsmar

5 Beds ⋅ 3 Baths ⋅ Turtle Creek Unit-One SubDv. ⋅ 34677 Zip Code

Experience exceptional golf course living at Eastlake Woodlands, Premier Turtle Creek Subdivision, where privacy, sophistication, and stunning views of the Ardea Country Club North Course Signature Hole #10 await you in this stylish, previous model home 5-bedroom, 3-bath home with a 3-car garage. Set within a gated community, this former model residence greets you with an impressive marble foyer and sweeping vistas of the greens. Inside, high ceilings, newly painted interiors, and a spacious floor plan cater to both entertaining guests and everyday comfort. The gourmet kitchen is equipped with stainless steel appliances, pristine tile countertops, a roomy pantry, center island, and bar seating that connects seamlessly to the inviting gathering room and breakfast nook. The expansive gathering area showcases dramatic vaulted ceilings, a fireplace, a wet bar, and windows that perfectly frame the peaceful golf course backdrop. Step outdoors to your own tranquil retreat—a large paver lanai featuring a pool, spa, and panoramic screened enclosure—ideal for relaxation or hosting friends. The elegant primary suite includes a cozy sitting alcove, workspace, custom walk-in closet, and a luxurious en-suite bath with marble finishes, garden tub, walk-in shower, and private water closet. The home’s split bedroom design offers flexibility, including a versatile office or fifth bedroom with French doors, built-in features, and numerous upgrades such as new garage doors (2018), fireplace conversion (2024), and updated hall bathrooms. Located in the sought-after Turtle Creek neighborhood, this property sits safely outside flood zones and has remained undamaged by storms. Eastlake Woodlands provides access to premier amenities through membership at the renovated Ardea Country Club, offering championship-level golf, tennis, pickleball, swimming, and fitness facilities. All of this convenience is just moments from excellent schools, shopping, dining, beautiful beaches, and Tampa International Airport. Room measurements are approximate. Be sure to explore the 3-D and virtual tours, floor plan and aerial drone photography, to fully appreciate all this remarkable home has to offer!

85 Kelleys Trail, Oldsmar

3 Beds ⋅ 3 Baths ⋅ Aberdeen Unit One SubDv. ⋅ 34677 Zip Code

Virtually Staged. A premier lot and location like this is so rare to find! Absolutely stunning describes this home’s pristine, sweeping golf course and water views with a magnificent lot perfectly positioned and affording much sought-after privacy from neighboring homes – creating a serene backdrop for relaxation and elegant entertaining. Nestled in the beautiful Aberdeen subdivision, this residence is located within the desirable gated golf community of East Lake Woodlands. Longing for a golf course lot but worried about fencing? A very special feature is the masonry wall enclosure located on the side of the home and measuring 50 feet long and 3 feet high - perfect for pets, a garden, play area or to create your own putting green - lots of possibilities to fit your individual needs! Stepping inside you are greeted with soaring volume ceilings, expansive living spaces, neutral tones throughout and transom windows and glass sliders inviting natural light while seamlessly connecting the interiors to the resort-style outdoor setting. A showcase gas fireplace anchors the family room complete with wet bar, adding sophistication and warmth, while the thoughtfully designed split floor plan offers exceptional privacy for owners and guests alike with 3 bedrooms plus an office/den that can be converted to a 4th bedroom. The kitchen blends style and function with stainless steel appliances, granite countertops, abundant cabinetry, a breakfast bar and ample eat-in area where golf course panorama can be enjoyed daily. Retreat to the primary suite with serene views and spacious bathroom with dual vanities, soaking tub, walk-in shower and 2 sizable closets. The expansive outdoor retreat is designed to impress, featuring a large sparkling pool and spa, generous covered lounging and dining areas and a well-appointed outdoor kitchen with gas grill. This lot is located in the preferred Zone X which does not require flood insurance and the owners had no issues during the 2024 hurricanes. Additional peace of mind comes with two Trane A/C units replaced in 2025, including 5-ton and 2-ton units. Major $7,500 investment in irrigation system renovation and brand new sod in front lawn all ready for new owners! Offering an enviable combination of privacy, luxury, indoor-outdoor living, and picturesque views, this East Lake Woodlands residence presents a rare opportunity to enjoy an elevated lifestyle in one of the area’s most desirable gated golf communities. Optional memberships are available for a wide array of amenities with Ardea Country Club including 2 golf courses, tennis and pickle ball, fitness center, heated lap and free form pools, dining and social events. All this in a premier location convenient to Tampa International Airport, medical facilities, A-rated schools, award-winning beaches as well as professional sporting events, concerts, fine dining and more in the Tampa Bay area. Premier privacy and stunning views are hard to come by - you can enjoy waking up to this incredible scenery and make this home truly your own at this exceptional price.

4995 Camberley Lane, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Bays End SubDv. ⋅ 34677 Zip Code

Roof 2026!! Welcome to Bays End, a hidden gem community offering a peaceful setting with convenient access to everything the area has to offer. This well-maintained 3-bedroom, 2-bathroom home features a spacious and inviting layout. Enter to an open living room that flows into the dining area. The updated kitchen showcases beautiful cabinetry, generous storage, and plenty of workspace. The heart of the home is the family room, with vaulted ceilings and a fireplace create a warm and open space. The spacious primary suite offers walk-in closets and a tastefully updated en-suite bathroom. Split plan with two bedrooms and a bathroom. Step outside to your own private backyard retreat featuring a pool, spa, paver patio, and fully fenced yard—perfect for relaxing, entertaining, or enjoying Florida's year-round sunshine.

854 Christina Circle, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Fountains At Cypress Lakes Ii-B SubDv. ⋅ 34677 Zip Code

Welcome Home to this highly sought-after and well established community of The Fountains At Cypress Lakes. MOVE IN READY! Offering Privacy, serenity, and modern upgrades, this residence is a rare find. Enjoy peaceful comfortable living on the expansive screened in lanai and pool overlooking lush landscaping and stone walk-ways, towering trees, Pond, and Conservation area. Secluded Park-like setting. Enjoy the views as you enjoy the wildlife sightings. Three bedroom split plan with a separate Study/Bonus room. The bonus room adjoins the main living areas with double entry doors, and back door to pool area. Dining room and Great room with direct access to the lanai. through the double glass door. Gourmet kitchen features plenty of space for eat-in area, solid counter tops, pantry closet, and Breakfast bar, and custom wood cabinetry. You will enjoy entertaining in this open concept home. Accent walls and insets to showcase your artwork and or special pieces. Beautiful flooring throughout. Inside Utility room with extra shelving. Double wide baseboards throughout. Large primary suite with 2 walk-in closets. Primary bath with sunken tub, and separate walk-in shower with designer tile and custom glass shower doors. Shutters on all windows. Oversized 3 car garage with workbench, and custom overhead storage rack. This neighborhood is tucked away and Minutes to all shopping, restaurants, and convenient to all medical facitlities, hospitals and Tampa Airport. Golfcourse's and beaches close by. Well maintained and pride of ownership.

392 Tavernier Circle, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Worthington SubDv. ⋅ 34677 Zip Code

Welcome to 859 Inverry Drive in the highly sought-after East Lake Woodlands community of Oldsmar! Beautifully renovated from top to bottom, this exceptional pool home combines modern updates, timeless style, and Florida living at its finest. From the moment you arrive, you'll be captivated by the home's exceptional curb appeal, mature landscaping, and inviting presence. Step inside to discover a completely updated interior featuring luxury flooring, a stunning remodeled kitchen, and beautifully renovated bathrooms. Every detail has been thoughtfully designed to create a move-in-ready home that feels both elegant and comfortable. The spacious floor plan provides an ideal setting for everyday living and entertaining, while large windows fill the home with natural light. The chef-inspired kitchen showcases stylish finishes, updated cabinetry, and modern appliances, making it the heart of the home. Step outside to your private backyard retreat where a sparkling pool awaits. Surrounded by lush landscaping, the outdoor living space offers the perfect setting for relaxing, hosting guests, or enjoying year-round Florida sunshine. Located in the desirable East Lake Woodlands community, this exceptional home provides convenient access to shopping, dining, parks, golf, and top-rated schools. With extensive renovations already completed, all that's left to do is move in and enjoy. Don't miss your opportunity to own this beautifully updated pool home in one of Oldsmar's most desirable neighborhoods!

859 Inverry Drive, Oldsmar

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

3 Beds ⋅ 2 Baths ⋅ Harbor Palms-Unit Three SubDv. ⋅ 34677 Zip Code

Nestled in the heart of Oldsmar, this location offers the perfect blend of small-town charm, outdoor recreation, and everyday convenience that makes living in Harbor Palms so desirable. Situated HIGH AND DRY with NO history of flooding, residents enjoy being just minutes from the waterfront parks and trails along Tampa Bay, including R.E. Olds Park, Veterans Memorial Park, and the scenic Upper Tampa Bay Trail. Whether you're spending the day kayaking, biking, fishing, or enjoying one of the area's many community events, Oldsmar embraces an active Florida lifestyle while maintaining a welcoming neighborhood feel. This beautifully renovated 3-bedroom, 2-bathroom POOL home offers over 2,100 square feet of thoughtfully designed living space. From the moment you arrive, the inviting curb appeal sets the stage for the upgrades found throughout the home. Luxury vinyl plank flooring flows seamlessly from room to room, creating a modern and cohesive feel. The front living room transitions effortlessly into the dining area and spacious family room, where a cozy fireplace flanked by built-in shelving serves as the focal point. The centrally located galley-style kitchen is sure to impress with quartz countertops, stainless steel appliances, a statement vent hood, crisp white cabinetry, and a stylish backsplash. The oversized owner's suite offers a private retreat complete with a large walk-in closet and an ensuite bathroom featuring floor-to-ceiling tile and a walk-in shower. Two additional bedrooms are conveniently located near the beautifully updated guest bathroom. A dedicated mudroom with washer and dryer hookups adds extra functionality and storage space. Step outside to the screened-in lanai overlooking the sparkling in-ground pool, creating the perfect setting for relaxing or entertaining guests. Major updates include a new roof and AC in 2024, providing peace of mind for years to come. One of the biggest advantages of living here is the incredible convenience and abundance of nearby amenities. Harbor Palms Nature Park is just steps away and features a kayak launch, scenic boardwalk, walking trails, and an 18-hole disc golf course. Sheffield Park is also nearby with basketball and tennis courts, baseball and softball fields, and a dog park. Centrally located between Tampa, Clearwater, and Palm Harbor, residents enjoy easy access to Tampa International Airport, award-winning Gulf beaches, shopping, dining, entertainment, Mease Countryside Hospital, Tampa Bay Downs, and the Oldsmar BMX Supercross Track. With beautiful parks, a strong sense of community, and a prime Tampa Bay location, it's easy to see why Oldsmar continues to be one of the area's most sought-after places to call home. Schedule your showing today!

1811 Forest Drive, Oldsmar

4 Beds ⋅ 3 Baths ⋅ Turtle Creek Unit-Three SubDv. ⋅ 34677 Zip Code

If you've been searching for a home that checks every box, this one is worth a serious look. Tucked inside the guard-gated East Lake Woodlands community — known for its canopied streets, two championship golf courses, pickle ball and tennis courts, and home to Ardea Country Club — this 4-bedroom, 3-bath pool home sits on nearly a full acre and has been genuinely well cared for. Equipped with a whole-house solar system - means electric bills that are almost laughably low — most months you're paying little more than the base statement fee. Pair that with a whole-home water filtration system, water softener, two brand-new AC units (April 2025 and March 2026), a tile roof replaced in 2019, and two water heaters also replaced in 2019, and you're looking at a home where the expensive stuff has already been done. At 3,189 square feet, the layout gives everyone room to breathe. The great room is the kind of space that feels both impressive and livable, and the split floor plan keeps the primary suite — complete with walk in closets and a sitting area — separate from the other bedrooms. Tile flooring runs throughout the entire home, so there's no carpet to worry about. The kitchen is built for real use: breakfast bar, convection oven, cooktop, and quality appliances, all with stone counters. Out back, the pool and lanai open up to a quiet, private setting that makes it easy to forget the rest of the world exists. Top-rated schools, easy access to Tampa, and a short drive to the Gulf beaches round out a package that's hard to replicate at this price point.

4931 Turtle Creek Trail, Oldsmar

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