Oldsmar Homes with Pool

Oldsmar Homes with Pool

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 is a delightful blend of natural beauty and modern amenities. This picturesque city is ideally situated between the bustling urban centers of Tampa and Clearwater, making it a perfect retreat for those who seek a balanced lifestyle.

Oldsmar boasts an array of outdoor recreational opportunities, including beautiful parks, scenic waterfronts, and access to the stunning Gulf Coast beaches. The city's commitment to preserving green spaces ensures that residents can enjoy the great outdoors year-round. From hiking and biking trails to serene picnic spots, Oldsmar is a haven for nature lovers and families alike.

When it comes to real estate, Oldsmar offers a diverse selection of homes, with many featuring luxurious pools that invite you to unwind and relax in the warm Florida sun. Imagine coming home to your very own oasis, where you can host summer barbecues, enjoy evening swims, or simply lounge by the poolside with a good book. These homes with pools not only provide a refreshing escape but also enhance your lifestyle, making every day feel like a vacation.

Whether you're a first-time homebuyer, a growing family, or looking to retire in a peaceful environment, Oldsmar has something for everyone. With its friendly community, excellent schools, and convenient access to shopping and dining, this charming city is the perfect place to call home. Explore the possibilities and discover your dream home in Oldsmar today!

Newest Oldsmar Homes with Pool

116 Brent Circle, Oldsmar
$405,000
3 Beds ⋅ 3 Baths ⋅ TB8558582 MLS ⋅ 116 BLDG.
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
129 Caryl Way Unit 129, Oldsmar
$129,900
2 Beds ⋅ 2 Baths ⋅ TB8559342 MLS
Short Sale. UNAPPROVED SHORT SALE – Renovation Opportunity in Highly Desirable East Lake Woodlands! Bring your vision and transform this 2-bedroom, 2-bathroom condo into your ideal Florida retreat! Located within the highly sought-after, guard-gated community of East Lake Woodlands in Oldsmar, this property presents an excellent opportunity for buyers looking to renovate and make it their own. Whether you're searching for a primary residence, seasonal getaway, or investment opportunity, this condo offers plenty of potential. Enjoy the beautiful surroundings of this established community, conveniently located near shopping, dining, entertainment, beaches, and everything the Tampa Bay area has to offer. The HOA fee includes cable TV, high-speed internet, water, sewer, trash collection, exterior maintenance, grounds maintenance, community pool, and reserves, providing added convenience and value. Property is being sold as an unapproved short sale, subject to lender approval. Bring your creativity and take advantage of this opportunity to own in one of Oldsmar's most desirable communities!

129 Caryl Way Unit 129, Oldsmar
1726 Split Fork Drive, Oldsmar
$599,000
4 Beds ⋅ 3 Baths ⋅ TB8559073 MLS
HEAVILY RENOVATED POOL HOME NOT IN A FLOOOD ZONE! Welcome to this beautifully updated 4-bedroom, 2.5-bathroom home offering 2,230 heated square feet of thoughtfully renovated living space. From the moment you step inside, you’ll appreciate the fresh, modern finishes and extensive improvements throughout. The heart of the home is a stunning new gourmet kitchen featuring stylish finishes and designed for both everyday living and entertaining. New luxury vinyl flooring flows throughout the main living areas, complemented by fresh interior paint for a clean, move-in-ready feel. Step outside to your private backyard retreat featuring a brand-new in-ground pool and expansive paver patio, creating the perfect setting for relaxing, entertaining, and enjoying the Florida lifestyle. Additional major updates include a brand-new A/C system and a pool heater, providing valuable peace of mind and enjoyment for the next homeowner. One of the home’s standout advantages is its high-and-dry location above the floodplain, with no flood insurance required. Located in desirable Oldsmar, this home offers convenient access to Tampa Bay and the area’s beautiful waterfront destinations, white-sand Gulf beaches, parks, dining, shopping, and retail. With its central location and extensive renovations already completed, this home delivers the ideal combination of comfort, style, convenience, and Florida outdoor living. Nothing left to do but move in and enjoy! This home will not last long, come see it today!

1726 Split Fork Drive, Oldsmar
1558 E Lake Woodlands Parkway, Oldsmar
$739,000
3 Beds ⋅ 2 Baths ⋅ TB8557574 MLS
Virtually Staged. Discover an updated, move-in ready home with stunning design and finishes that flow beautifully throughout - all set on a desirable corner lot within the gated golf community of East Lake Woodlands. Offering 3 bedrooms, 2 full bathrooms, a 3-car garage and a landscaped, fenced backyard, this inviting home combines comfortable everyday living with a convenient Tampa Bay location. Complemented by abundant natural light, high ceilings, crown molding and an open, welcoming layout, this residence features beautiful hardwood and engineered wood flooring throughout the living areas and bedrooms - so no carpet! The bright living room and dining room combination provides an elegant setting for entertaining with a signature arched window complete with plantation shutters and glass sliders leading to the outdoors. Open to the family room, the updated kitchen provides a seamless space for gatherings and daily living and features stainless steel appliances including double GE convection ovens, induction cooktop, Bosch dishwasher and an expanse of updated cabinetry with convenient pull-outs and Lazy Susan, Cambria quartz countertops, large breakfast bar and pantry storage. Glass sliders and a wood burning fireplace accent the family room and provide an inviting place to relax. With a split floor plan, the primary suite is designed for privacy and pampering, featuring 2 closets with custom built-in cabinetry installed in 2025, glass sliders overlooking the tranquil backyard and a luxurious primary bath with gorgeous tile, large tub and double vanity with granite countertops. The secondary bathroom has been updated with attractive tile finishes and granite countertops as well, providing a polished complement to the home’s interior. Improvements include a Generac home generator with a buried 500-gallon propane tank, a 2023 water heater, 2022 water softener and 2010 tile roof. These updates add practical value and enhance the home’s functionality and peace of mind as well as a location in Zone X, the lower probability flood zone which does not require flood insurance by lenders. Outside, the landscaped corner-lot setting offers a wide driveway for plenty of parking for family and guests, mature trees and a fenced backyard with privacy and room to create a relaxing outdoor retreat. The 3-car garage provides generous parking and additional storage while the home’s layout and surrounding greenery add to its everyday ambiance. East Lake Woodlands offers a gated golf-community setting near top-rated schools, medical facilities, shopping, airports, professional sporting events and the many attractions of the Tampa Bay area. Optional memberships to Ardea Country Club provide access to 2 golf courses, tennis and pickle ball, a fitness center, heated lap pool and free form pool with a poolside café, casual and fine dining and a host of social events and activities.

1558 E Lake Woodlands Parkway, Oldsmar
1290 Clays Trail Unit 1403, Oldsmar
$469,000
3 Beds ⋅ 3 Baths ⋅ TB8552126 MLS ⋅ 1290 BLDG.
Welcome to true maintenance-free living in the gated golf community of East Lake Woodlands. Simplify your life while still enjoying plenty of room with this move-in ready, spacious 2,700-sq. ft. townhome-style condominium offering 3 bedrooms, 2.5 baths, a versatile first-floor bonus area and sweeping golf course views. The bonus space offers exceptional flexibility and can be used as a home office, exercise room, playroom, media space or den. With high ceilings, crown molding and an inviting open-concept design, this home seamlessly connects the kitchen, dining area and family room creating an ideal setting for everyday living and entertaining. Inviting is the word to describe the well-appointed kitchen featuring wood cabinetry, gleaming granite countertops, expansive breakfast bar with plenty of seating and direct sightlines into the family room with recent updates including new lighting and Frigidaire Gallery refrigerator and Whirlpool microwave (2025). Other updates in 2025 include fresh interior paint, a new LG washer and dryer and new ceiling fans and light fixtures. The efficient 5-ton air-conditioning unit was replaced in 2025 as well providing added peace of mind. As a private retreat, the spacious primary suite affords gorgeous golf course views, wood floors, a large walk-in closet and an additional sitting area perfect for a den, reading nook or home office. The beautifully appointed primary bath features new cabinetry with tower storage, stunning quartz countertops, a freestanding soaking tub and gorgeous tile throughout. Two additional bedrooms provide generous room for family and guests and ample closet space. The secondary bathrooms feature updated cabinetry with quartz countertops in addition to an updated laundry room. Enjoy Florida living on the screened, covered patio, with an additional open area perfect for grilling, outdoor dining and entertaining while taking in the tranquil golf course backdrop. The maintenance-free lifestyle makes it easy to simplify and relax, with just two monthly bills to manage. With the 2025 A/C, electric bills for the owner have typically ranged from $130 to $230 during the summer, while the condo monthly maintenance fee covers comprehensive services including water and sewer, trash and recycling collection, lawn care and maintenance, exterior building maintenance including roof (installed 2020), termite prevention program, cable and internet services, insurance on building structure and escrow reserves. Plus residents also enjoy access to a sparkling community pool! Optional memberships are available for Ardea Country Club, offering access to 2 golf courses, fitness center, tennis and pickleball, a heated lap pool and freeform pool, poolside café, casual dining and a variety of social events and activities. Conveniently located near Tampa International Airport, top-rated schools, medical facilities, beaches and parks, professional sporting events and the many attractions of Tampa Bay, this East Lake Woodlands home delivers comfort, convenience and amenities all with golf course views. Move-in ready and maintenance free means more time to relax when at home or traveling!

1290 Clays Trail Unit 1403, Oldsmar
1801 Mapleleaf Boulevard, Oldsmar
$451,000
3 Beds ⋅ 3 Baths ⋅ TB8558659 MLS
Virtually Staged. Light-filled living spaces, a split bedroom plan, and a screened pool create an inviting setting in this four-bedroom, two-bath Oldsmar home with a two-car garage and inside laundry. The living room and dining area offer a separate setting for entertaining or quieter gatherings, while the kitchen and family room combine for everyday living. Large windows, arched architectural details, and beautiful flooring add character and warmth, with opportunities to update finishes and make the spaces your own. The kitchen features light cabinetry, stainless steel appliances, and a breakfast bar for casual meals or conversation with the cook. Its connection to the family room keeps the spaces open and social, while sliding glass doors lead to the screened pool area. The primary bedroom also offers sliding-door access to the pool, and its adjoining bathroom includes dual sinks, a separate tub, and a shower. An inside laundry room with overhead cabinetry adds practical storage. Outside, the pool and screen enclosure set the scene for relaxed afternoons, weekend gatherings, and a refreshing swim at the end of the day. Picture comfortable outdoor seating for morning coffee, a dining spot for casual meals, and your own touches of greenery to bring the space together. Beyond the enclosure, the fenced backyard offers possibilities for garden beds, flowering plants, or a landscaped sitting area. Whether you envision a quiet retreat or a setting for entertaining, the outdoor spaces offer an opportunity to create an extension of the home that reflects your style. Located near Tampa Road and the Curlew Road corridor, the property offers convenient access to shopping, grocery stores, restaurants, and everyday services throughout Oldsmar, nearby Palm Harbor, and the Countryside area. Connections to US 19, McMullen Booth Road, and Hillsborough Avenue provide routes throughout Pinellas County and into Tampa. Outdoor destinations Mobbly Bayou Wilderness Preserve, offering waterfront settings, trails, fishing, and kayaking, while John Chesnut Sr. Park and Philippe Park are each approximately five miles away. Local schools and St. Petersburg College provide nearby educational options. Tampa International Airport is approximately 14 miles away, and St. Pete–Clearwater International Airport is approximately 16.5 miles away. Come explore the layout, outdoor spaces, and possibilities this Oldsmar pool home has to offer. All distances are approximate and vary by route. Buyers to verify school zoning and enrollment availability directly with Pinellas County Schools. All information is believed to be accurate but is not guaranteed. Buyers and agents to verify all facts and information pertinent to their purchase decision.

1801 Mapleleaf Boulevard, Oldsmar
4878 Sherbrook Drive, Oldsmar
$929,900
5 Beds ⋅ 3 Baths ⋅ TB8558220 MLS
Welcome to this beautifully refreshed 5 bedroom, 3 bathroom, 3 car garage pool home nestled within the highly sought-after, gated community of East Lake Woodlands! Offering an exceptional blend of space, comfort, and Florida living, this move in ready residence has recently undergone a stunning makeover and is ready for its new owners! Thoughtfully designed with a desirable three-way split floor plan, this home provides both privacy and functionality, making it ideal for everyday living and entertaining. Upon entering, you're greeted by a spacious formal living and dining area with sliding glass doors that invite you to your private outdoor oasis. The expansive family room seamlessly connects to the kitchen, where soaring ceilings and an abundance of natural light create a bright and inviting atmosphere. The kitchen is an entertainer's dream, featuring quartz counters, stainless steel appliances and a breakfast nook. Retreat to the private primary suite, thoughtfully positioned on its own side of the home, featuring a spacious walk-in closet and an ensuite bathroom complete with dual vanities, a relaxing freestanding soaking tub, a walk-in shower with dual showerheads, and a private water closet. Two additional generously sized bedrooms share a conveniently located bathroom, while a separate area offers another bedroom and adjacent full bathroom. Step outside and experience Florida living at its finest! Your private backyard retreat features a sparkling swimming pool, generous covered entertaining space, and a brand-new outdoor kitchen, creating the perfect setting for weekend barbecues, hosting friends and family, or simply unwinding in your own tropical escape. Additional highlights include a spacious three-car garage offering plenty of room for vehicles, storage, and recreational equipment. Located within the prestigious East Lake Woodlands community, residents enjoy the privacy of gated living surrounded by beautiful landscaping and an established neighborhood atmosphere. Optional country club memberships provide access to an array of amenities, including championship golf, tennis, dining, social events, and recreational activities, with various membership opportunities available to suit your lifestyle. Freshly updated, thoughtfully designed, and perfectly suited for the Florida lifestyle, this East Lake Woodlands gem is ready to welcome you home. Schedule your private showing today!

4878 Sherbrook Drive, Oldsmar
4795 Pebble Brook Drive, Oldsmar
$485,000
2 Beds ⋅ 2 Baths ⋅ TB8557679 MLS
Warm. Inviting. Bright. A truly move in ready home in the sought out gated community of East Lake Woodlands. This 2 bedroom 2 bath plus den, features granite counters, wood cabinets, plantation shutters, crown molding, inside laundry room, screened lanai, high ceilings formal dining area, dinette in kitchen. Furnishings negotiable. The community itself is gated and offers 2 18 hole golf courses, fitness center, tennis and pickleball courts.

4795 Pebble Brook Drive, Oldsmar
10 Windrush Court, Oldsmar
$765,000
3 Beds ⋅ 3 Baths ⋅ TB8558083 MLS
Tucked away on a quiet cul-de-sac, with a BRAND NEW ROOF, this exceptional single-family residence sits on an oversized lot with tranquil pond views, offering a rare blend of privacy, elegance, and resort-style outdoor living. Designed for both relaxation and entertaining, the backyard retreat features an oversized heated swimming pool, expansive screened lanai, and a generous covered outdoor dining area just off the family room—perfect for hosting gatherings or enjoying Florida evenings. A fully equipped outdoor kitchen adds convenience, while automated wind-resistant screens protect the lanai space when needed. Off the primary suite, an additional private covered patio creates the perfect shaded escape. Inside, the recently remodeled kitchen and family room serve as the heart of the home, showcasing granite countertops, rich wood cabinetry, a striking metal tile backsplash, upgraded lighting and fan fixtures, dual microwave/oven, and a cooktop with breakfast bar overlooking the family room. A charming breakfast nook provides additional seating with picturesque views of the pool and outdoor living area. The family room impresses with soaring vaulted ceilings, skylights that flood the space with natural light, a stylish wet bar, and an electric fireplace insert that provides both warmth and ambiance. Both rear guest bedrooms feature engineered “Tiger Eye” wood flooring, fresh paint, and updated ceiling fans. The second bathroom has been tastefully updated with wood cabinetry, stone countertops, and tile flooring. Throughout the home, popcorn ceilings have been removed, giving every room a clean, modern finish. The primary suite offers a luxurious retreat, featuring engineered wood flooring in the bedroom and closet and a beautifully renovated ensuite bath with dual quartz vanities and an elegant open walk-in tile shower. The roof has been enhanced with a Roof Max protective treatment and transferable 5-year warranty, along with a 2015 A/C system. Combining thoughtful upgrades, refined interior spaces, and exceptional outdoor living, this home offers a private cul-de-sac setting with the perfect balance of comfort, style, and Florida lifestyle living. Additional upgrades and features include: • New Decorative carpet inset in the living room • Dining room with engineered wood flooring with newer Bay Window • Convenient guest half-bath • New double front entry doors with a custom tiled walkway and entry accents • Updated landscaping with new garden rock and curbing (2024) • New golf cart garage door ' New Interior and Exterior Painting and MORE! Combining thoughtful upgrades, refined interior spaces, and exceptional outdoor living, this home offers a private cul-de-sac setting with the perfect balance of comfort, style, and Florida lifestyle living.

10 Windrush Court, Oldsmar
131 Cypress Lane Unit 131, Oldsmar
$104,000
2 Beds ⋅ 2 Baths ⋅ TB8557702 MLS ⋅ 131 BLDG.
Bring a vision and a renovation budget. This 2-bedroom, 2-bath condo in Oldsmar is sold as-is, and the price reflects what it needs: a deep clean, new flooring throughout, and cosmetic updates to the kitchen and baths. The location is already here, and the finishes are up to you. Located in Cypress Estates in East Lake Woodlands, minutes from Tampa Road, R.E. Olds Park, and the Oldsmar waterfront, with easy access to Westchase, Clearwater, and Tampa International Airport. A strong fit for investors, renovation-minded homeowners, and anyone looking to build equity through their own work. Sold as-is. Cash or renovation financing recommended.

131 Cypress Lane Unit 131, Oldsmar
392 Cobia Way, Oldsmar
$178,000
2 Beds ⋅ 2 Baths ⋅ TB8557814 MLS
Welcome home to your Florida Retreat in Oldsmar! Discover the perfect blend of comfort, convenience and coastal charm in this beautifully maintained, move-in ready, furnished 2-bedroom, 2-bathroom, nestled in the heart of Oldsmar, Florida! Featuring a relaxed coastal vibe, this inviting home offers updated kitchen cabinets, bathroom vanities and showers, laminate flooring throughout, built-in cabinetry in the kitchen and dining areas, and an open-concept layout. The spacious living room and dining areas, complemented by plantation shutters, provide a welcoming setting for entertaining guests or simply relaxing in comfort. The generously sized primary suite features an updated en-suite bathroom, a spacious walk-in closet and a walk-in shower. Additional improvements include double-pane windows throughout, a newer central air conditioning system, water heater and a leaf guard system, backed by a lifetime warranty. Located in the highly desirable 55+ community of Gull-Aire Village, this golf cart-friendly neighborhood offers an exceptional lifestyle with resort-style amenities including a spacious clubhouse, large, heated pool and spa, library, enclosed shuffleboard court, bocce ball court, and an active calendar of social events and activities. Enjoy the added advantage of owning the land with an affordable monthly HOA fee of just $70. One pet of any size is welcomed and two boat and RV storage areas are available for a low monthly rental fee. You’ll love the unbeatable location is less than a mile from Woodlands Square and just minutes to everyday conveniences. Honeymoon Island Beach is approximately 9 miles away, Mease Countryside Hospital among other health facilities are approximately 2 miles away, St.Pete/Clearwater Int'l Airport is a quick 11-miles away and Tampa Int'l Airport is only a 15-mile drive. For those of you who enjoy the outdoors, the adjacent walking, running, and biking trail along Canal Way leads directly to picturesque Sheffield Park, offering another wonderful way to embrace Florida’s outdoor lifestyle. Whether you’re socializing at the clubhouse, relaxing by the sparkling pool, or simply soaking in the tranquil pond views, you’ll appreciate the welcoming atmosphere and vibrant lifestyle that make Gull-Aire Village such a special place to call home. Don’t miss this opportunity to enjoy affordable Florida living in a desirable, amenity-rich community. Schedule your private tour today!(Room dimensions are approximate and should be verified by the Buyer.)

392 Cobia Way, Oldsmar
112 Cypress Court Unit 112, Oldsmar
$149,900
2 Beds ⋅ 2 Baths ⋅ TB8557703 MLS ⋅ 112 BLDG.
MOTIVATED SELLER! This 2-bedroom, 2-bath condo in the golf course community of East Lake Woodlands is ready for its next owner. Brand-new LVP flooring was installed in 2026, and a fresh coat of paint is being finished now, so the unit shows bright, clean, and move-in minded. Low-maintenance condo living means more time to enjoy the community, which offers a golf course and a clubhouse right where you live. Location is a big part of the value here. US-19 is minutes away, with quick access to shopping, dining, and the rest of the Tampa Bay area. First-time buyer, downsizer, seasonal resident, or investor, this one fits a lot of plans. The seller is motivated and the price reflects it. Schedule your showing today.

112 Cypress Court Unit 112, Oldsmar
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