Oldsmar Homes with Private Pool type

Oldsmar Homes with Private Pool type

Welcome to Oldsmar, Florida—a hidden gem nestled in the heart of Pinellas County. With its charming small-town vibe and picturesque landscapes, Oldsmar offers a unique blend of suburban tranquility and vibrant community spirit. Located just minutes from the stunning Gulf Coast beaches and the bustling cities of Tampa and Clearwater, residents enjoy the best of both worlds: serene living with easy access to urban amenities.

Oldsmar is renowned for its lush parks, scenic trails, and a rich array of recreational activities. Whether you're exploring the beautiful waterfront of Old Tampa Bay or enjoying a family day at one of the local parks, there’s always something to do. The city also boasts a lively downtown area filled with delightful shops, restaurants, and cultural events that foster a strong sense of community.

For those seeking the ultimate in luxury and relaxation, Oldsmar is home to an exquisite selection of residences featuring private pools. Imagine stepping into your own backyard oasis, where you can unwind after a long day or host unforgettable gatherings with family and friends. Homes with private pools in Oldsmar range from charming single-family houses to modern estates, each offering a unique blend of comfort and style.

With its welcoming atmosphere and beautiful homes, Oldsmar is the perfect place to create lasting memories. Discover your dream home with a private pool in this idyllic city, where every day feels like a vacation!

Newest Oldsmar Homes with Private Pool type

1726 Split Fork Drive, Oldsmar
$599,000
4 Beds ⋅ 3 Baths ⋅ Eastlake Oaks Ph 1 SubDv. ⋅ 34677 Zip Code
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
1801 Mapleleaf Boulevard, Oldsmar
$451,000
3 Beds ⋅ 3 Baths ⋅ Bays End SubDv. ⋅ 34677 Zip Code
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 ⋅ Cross Pointe SubDv. ⋅ 34677 Zip Code
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
10 Windrush Court, Oldsmar
$765,000
3 Beds ⋅ 3 Baths ⋅ Greenhaven Unit One SubDv. ⋅ 34677 Zip Code
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
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
1704 Hibiscus Circle S, Oldsmar
$425,000
3 Beds ⋅ 2 Baths ⋅ Harbor Palms-Unit Six SubDv. ⋅ 34677 Zip Code
Welcome to this beautifully remodeled 3-bedroom, 2-bathroom home in Oldsmar, offering a desirable split-bedroom floor plan, modern finishes, and exceptional Florida indoor-outdoor living. Featuring a brand-new roof installed in 2026, hurricane impact windows and doors, tile flooring throughout, and a fully remodeled interior, this home is truly move-in ready. The stunning kitchen features quartz countertops, brand-new cabinetry, stainless steel appliances, and a spacious island with bar seating, creating the perfect spot for casual meals, morning coffee, or entertaining guests. The kitchen seamlessly flows into the spacious family room, surrounded by sliders and windows overlooking the sparkling pool, bringing in an abundance of natural light and creating a beautiful connection between the indoor and outdoor living spaces. The home offers two separate living areas, including a welcoming main living room and a secondary family room, providing plenty of flexibility for entertaining, relaxing, or everyday living. Both bathrooms have been completely remodeled, including the spacious primary suite with a double vanity and walk-in closet. Step outside to your private backyard oasis featuring a freshly resurfaced swimming pool, new pavers, a newly screened pool enclosure, and a brand-new aluminum fence surrounding the property. The pool area also offers convenient direct access to a bathroom, making pool days and entertaining effortless. The freshly remodeled garage adds even more functionality, while a backyard storage shed provides additional space for tools, equipment, and outdoor essentials. With no HOA, you have the freedom and flexibility to enjoy the property your way. Conveniently located in Oldsmar with easy access to Tampa International Airport, Gulf Coast beaches, shopping, dining, parks, and major roadways, this home combines modern upgrades, privacy, and the Florida lifestyle in one exceptional package. Zoned for Oldsmar Elementary, Carwise Middle, and East Lake High School, this is a fantastic opportunity to own a completely updated home in a highly convenient Oldsmar location.

1704 Hibiscus Circle S, Oldsmar
583 Longwood Court, Oldsmar
$509,999
3 Beds ⋅ 2 Baths ⋅ Manors Of Forest Lakes The SubDv. ⋅ 34677 Zip Code
Welcome to your own private Florida retreat in desirable Oldsmar! This spacious 3-bedroom, 2-bath home with a 2-car garage sits on over a quarter acre, offering plenty of room to relax, entertain in your enclosed sunroom, and enjoy the Florida lifestyle. Step outside to your private backyard oasis featuring a sparkling swimming pool and relaxing hot tub, under a large screened enclosure—perfect for cooling off on sunny afternoons, unwinding after a long day, or entertaining family and friends year-round. The generous homesite provides added privacy and outdoor space rarely found in many neighborhoods. Inside, the well-designed floor plan offers comfortable living spaces, three generously sized bedrooms, and two full baths, making the home ideal for everyday living or entertaining. The attached 2-car garage provides ample parking and additional storage. Conveniently located in Oldsmar, with easy access to Tampa, Clearwater, Tampa International Airport, shopping, dining, parks, recreation, and the beautiful Gulf Coast beaches. Enjoy the perfect combination of space, location, and resort-style outdoor living. Don't miss the opportunity to make this Oldsmar pool home your own—schedule your private showing today!

583 Longwood Court, Oldsmar
950 Waverly Street, Oldsmar
$699,000
3 Beds ⋅ 2 Baths ⋅ Country Club Add To Oldsmar Rev SubDv. ⋅ 34677 Zip Code
LOOKS LIKE IT CAME STRAIGHT OFF HGTV! Welcome to this GORGEOUS, COMPLETELY REMODELED POOL HOME situated on an incredible 1.01-ACRE LOT in Oldsmar! Offering 3 bedrooms, 2 baths and over 2,000 SQ FT of beautifully updated living space, this stunning home has been transformed from top to bottom with stylish finishes, thoughtful upgrades and major improvements already completed. From the moment you step inside, you’ll love the fresh, modern feel. The beautifully remodeled kitchen features NEW SOLID WOOD CABINETRY, NEW QUARTZ COUNTERTOPS, NEW STAINLESS STEEL APPLIANCES, INCLUDING AN OVEN WITH AIR FRY SETTING, and plenty of space for cooking and entertaining. NEW LUXURY VINYL PLANK AND TILE FLOORING flows throughout the home, complemented by NEW LIGHTING, NEW PLUMBING FIXTURES AND FRESH INTERIOR PAINT. The spacious split-bedroom floor plan offers multiple living areas, including a family room, great room and separate formal dining room, while the impressive STONE WOOD-BURNING FIREPLACE adds warmth and character. Retreat to the private primary suite featuring a spacious walk-in closet and a STUNNING SPA-LIKE BATHROOM, beautifully remodeled to create a relaxing, luxurious escape. And the updates don’t stop with the beautiful interior! This home also features a NEW ROOF, NEW GUTTERS, NEW ELECTRICAL PANEL, TWO NEW HVAC SYSTEMS AND FRESH EXTERIOR PAINT, giving you the benefit of extensive improvements both inside and out. Step outside and discover your own PRIVATE FLORIDA OASIS! The REFINISHED IN-GROUND POOL overlooks the expansive property surrounded by mature trees, creating an incredible setting for entertaining, relaxing or simply enjoying the outdoors. Enjoy easy access to BEACHES, AIRPORTS, SHOPPING, DINING, PARKS, RECREATION and everything the Tampa Bay area has to offer. THIS IS THE ONE YOU'VE BEEN WAITING FOR—SCHEDULE YOUR PRIVATE SHOWING TODAY!

950 Waverly Street, Oldsmar
1750 Split Fork Drive, Oldsmar
$625,000
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
1813 Driftwood Circle N, Oldsmar
$404,000
3 Beds ⋅ 2 Baths ⋅ Harbor Palms-Unit Two SubDv. ⋅ 34677 Zip Code
Welcome home to this beautifully remodeled 3 bedroom, 2 bath pool home in the heart of Oldsmar! Completely updated in 2025, this move-in ready home offers a bright, open floor plan with luxury vinyl flooring throughout and a desirable split- bedroom layout. The beautifully updated kitchen features quartz countertops, new stainless steel appliances, ample cabinetry and open design perfect for everyday living and entertaining. Both bathrooms have been tastefully remodeled with fresh, modern finishes. The spacious living area is highlighted by a beautiful brick wood-burning fireplace, adding warmth and character to the home. An inside laundry room adds everyday convenience, while the oversized one-car garage provides additional parking and storage, At the back of the home, a large Florida room overlooks the pool and provides the perfect space for relaxing or entertaining, with a new hurricane-impact sliding glass door providing easy access to the outdoor living area. Step outside to your own private Florida retreat featuring a sparkling pool and a large, fully fenced backyard with plenty of room to relax, entertain and enjoy the outdoors. A backyard shed provides additional storage for tools, pool equipment and more. Ideally located in Oldsmar with convenient access to shopping, dining, recreation and area beaches, plus approximately 20 minutes to Tampa International Airport. Beautifully updates, perfectly located and ready for its next owner-this charming Oldsmar pool home is one you wont wnt to miss!

1813 Driftwood Circle N, Oldsmar
1332 Preservation Way, Oldsmar
$1,700,000
4 Beds ⋅ 4 Baths ⋅ Preserve, The SubDv. ⋅ 34677 Zip Code
Pre-Construction. To be built. TO-BE-BUILT CUSTOM HOME- An exceptional opportunity to build your dream home in the prestigious East Lake Woodlands community. Located within The Preserve, this proposed custom residence is situated on a beautiful homesite in a double-gated, private golf community, offering an unparalleled combination of privacy, security, and an exceptional lifestyle. This proposed custom home offers approximately 3,530 square feet of heated living space and 4,465 square feet total under roof, featuring 4 bedrooms, 4 full bathrooms, a private den, and a 2-car garage. The thoughtfully designed floor plan showcases spacious living areas and a modern custom-home concept designed to complement this exceptional homesite. The property is offered as a to-be-built custom home package, including the lot. The floor plan, renderings, and images are provided as a representation of the proposed residence and are intended to showcase the potential of this custom-home opportunity. However you can choose the paint, finishes, cabinets and flooring. OR----- Create your own home, floorplan, size, dimensions and layout! Minimum square footage is 3500sf. Please note: This is a proposed home and has not yet been constructed. Floor plans, renderings, dimensions, finishes, features, and specifications are conceptual and subject to change. Final design, construction, selections, and approvals are subject to builder, buyer, architectural review, association requirements, and applicable governmental approvals. A rare opportunity to secure a beautiful homesite and create a brand-new custom residence in one of Oldsmar's most desirable communities.

1332 Preservation Way, Oldsmar
4951 Augusta Avenue, Oldsmar
$584,900
3 Beds ⋅ 3 Baths ⋅ Worthington SubDv. ⋅ 34677 Zip Code
Virtually Staged. Welcome to 4951 Augusta Avenue, a spacious two-story pool home situated on a desirable corner lot in the gated East Lake Woodlands community. Offering approximately 2,316 square feet, this well-maintained residence features 3 bedrooms, 2.5 bathrooms, a versatile upstairs loft, a formal living room, and a 2-car garage. A grand two-story entrance welcomes you into a bright interior with soaring vaulted ceilings and abundant natural light. The formal living and dining areas provide an elegant setting for entertaining, while the comfortable main living space offers plenty of room for everyday relaxation. Upstairs, the open loft can serve as a home office, media area, game room, or additional lounge space. Step outside to your private screened swimming pool and covered patio—an ideal setting for entertaining, outdoor dining, or relaxing while enjoying Florida’s year-round sunshine. The screened enclosure provides additional comfort, while the corner lot offers extra outdoor space and privacy. Ideally located near Tampa Road, East Lake Road, and McMullen Booth Road, the property offers convenient access to Oldsmar, Palm Harbor, Safety Harbor, Clearwater, Westchase, and Tampa. Shopping, restaurants, medical facilities, Tampa Bay Downs, Countryside Mall, parks, nature preserves, and recreational trails are all nearby. Gulf beaches, Honeymoon Island, Tarpon Springs, and Tampa International Airport are also within easy reach. East Lake Woodlands Country Club offers golf, tennis, pickleball, fitness, swimming, dining, and social activities through optional membership. Enjoy private pool living, flexible interior space, and a central Tampa Bay location within an established gated community.

4951 Augusta Avenue, Oldsmar
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