Oldsmar Homes with Pool Community Features

Oldsmar Homes with Pool Community Features

Welcome to Oldsmar, Florida, a hidden gem nestled in the heart of Pinellas County! This charming city, known for its serene landscapes and vibrant community, offers a perfect blend of suburban tranquility and urban convenience. With its picturesque parks, scenic waterfront views, and a plethora of outdoor activities, Oldsmar is an ideal place for families, retirees, and anyone seeking a laid-back lifestyle with easy access to the bustling cities of Tampa and St. Petersburg.

One of the standout features of Oldsmar is its inviting homes with pool community options. Imagine coming home to your own private oasis, where you can unwind in your backyard pool while enjoying the warm Florida sunshine. These homes are designed not just for living but for creating memorable moments with family and friends. Many of these properties boast spacious layouts, modern amenities, and beautifully landscaped yards that enhance the overall charm of the community.

Residents of Oldsmar enjoy a plethora of recreational activities, from biking along the scenic trails of the Oldsmar Trail to taking part in community events at the nearby parks. The city’s commitment to fostering a vibrant community spirit is evident in its local festivals, farmers' markets, and various social gatherings that bring neighbors together.

If you’re searching for a place that combines the comfort of home with the allure of a tight-knit community, Oldsmar’s homes with pool community features are waiting for you. Embrace the Florida lifestyle and make Oldsmar your new home today!

Newest Oldsmar Homes with Pool Community Features

127 Camphor Drive Unit E, Oldsmar
$114,900
2 Beds ⋅ 2 Baths ⋅ SubDv. ⋅ 34677 Zip Code
Welcome to The Gardens of Forest Lakes! This spacious FIRST-FLOOR, 2-BEDROOM, 2-BATH CONDO offers comfortable, low-maintenance Florida living with no stairs, TILE FLOORING THROUGHOUT and BEAUTIFUL POND VIEWS! Nestled in a peaceful setting surrounded by mature landscaping and lush greenery, this light and bright residence offers a wonderful combination of comfort, convenience and scenic surroundings. Step inside to a living and dining area with plenty of space to relax or entertain. Sliding glass doors lead to a covered patio overlooking the tranquil pond, creating the perfect spot to enjoy your morning coffee, watch the wildlife or simply unwind while taking in the peaceful water views. The kitchen offers ample cabinetry, generous counter space and a convenient breakfast/pass-through bar that opens to the main living area. The primary bedroom features a private ensuite bathroom and walk-in closet, while the second bedroom provides flexibility for guests, a home office or additional living space & adjacent guest bath. An interior laundry area adds everyday convenience. With tile flooring throughout and a functional floor plan, this condo provides a great opportunity to add your own personal touches while enjoying its desirable first-floor location and picturesque setting. Beyond the condo, residents can enjoy an impressive array of community amenities in a scenic lakefront 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 atmosphere throughout the community. Conveniently located in the heart of Oldsmar, close to shopping, dining, parks, beautiful Gulf beaches and Tampa International Airport. Whether you're searching for a primary residence, seasonal getaway or investment opportunity, this first-floor condo with beautiful pond views offers an excellent opportunity to enjoy the Florida lifestyle. Schedule your private showing today!

127 Camphor Drive Unit E, 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
1829 Foxboro Court, Oldsmar
$825,000
3 Beds ⋅ 2 Baths ⋅ Cross Pointe SubDv. ⋅ 34677 Zip Code
Welcome to your private retreat in the much sought-after gated, golf community of East Lake Woodlands. Beautifully renovated and move-in ready, this three-bedroom plus alcove, two-bath pool home is ideally positioned on a serene cul-de-sac with a beautifully landscaped lot, exceptional privacy and spacious yard. From the moment you arrive, the home’s high ceilings and abundant natural light create a bright and welcoming atmosphere. The open-concept seamlessly connects the living room and dining room making everyday living and entertaining effortless with a stunning view of the pool area and lush setting. The family room opens directly to the kitchen and features a wood-burning fireplace and plantation shutters. Designed for both style and function, the kitchen was updated in 2026 with signature finishes such as upgraded Latte Luxe quartz countertops, beautiful glass tile backsplash, an island with breakfast bar seating and Samsung Bespoke stainless steel appliances, including convection oven. Enjoy a spa-like escape with the luxurious primary bathroom renovated in 2026 with elegant creamy quartz countertops, dual vanities, backlit mirrors, a stunning walk-in shower and a sitting area all with bright natural light and exquisite chandelier – plus feel totally pampered with a custom closet featuring built-ins complete with well-designed accessory and jewelry drawers. With views of the sparkling pool and abundant greenery, the two secondary bedrooms offer comfortable accommodations, glass sliders and access to a well-appointed bath with calming tones, large vanity and walk-in shower and access to the pool area. The second bedroom even includes additional flexible space that can be used as a small office, study area or hobby space. Step outside to a serene view from the gorgeous covered and screened patio. The inviting pool and spa, highlighted with cream, beige, charcoal pavers, creates a relaxing setting for morning coffee, gatherings or quiet evenings while enjoying privacy. This outdoor space truly feels like a peaceful retreat and is ideal for enjoying the Florida lifestyle. Recent improvements provide added peace of mind and modern convenience. New landscaping and all new interior and exterior painting completed in 2025. Additional notable updates include the tile roof replaced in 2020, new gutters with leaf guards installed in 2024, water heater replaced in 2022 and new pool heater installed in 2025. Updates extend to the laundry room as well for added convenience and functionality complete with 2026 LG washer and dryer included in the sale. Also in 2026, the home was enhanced with a new security and lighting system, a new front-door security entry lock and a smart garage-door opener and new irrigation control panel in 2025. East Lake Woodlands offers a desirable location convenient to Tampa International Airport, top-rated schools, medical facilities, beautiful beaches and parks, professional sporting events and the area’s many dining, shopping, and entertainment destinations. Optional memberships to Ardea Country Club are available and provide access to two golf courses, fitness center, heated lap pool, a freeform pool with poolside café, tennis and pickleball, casual and fine dining and a wide array of events. With thoughtful renovations, a cul-de-sac location, premier landscaping and easy-maintenance finishes, this home allows you to truly relax in a tranquil setting and enjoy the many updates that have been completed!

1829 Foxboro Court, 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
129 Caryl Way Unit 129, Oldsmar
$129,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
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
1558 E Lake Woodlands Parkway, Oldsmar
$739,000
3 Beds ⋅ 2 Baths ⋅ Greenhaven Unit-Four SubDv. ⋅ 34677 Zip Code
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 ⋅ Laurel Oaks At East Lake SubDv. ⋅ 34677 Zip Code
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
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
4795 Pebble Brook Drive, Oldsmar
$485,000
2 Beds ⋅ 2 Baths ⋅ Cross Creek - Unit Two SubDv. ⋅ 34677 Zip Code
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
392 Cobia Way, Oldsmar
$178,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
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 ⋅ East Lake Woodlands Cypress Estates SubDv. ⋅ 34677 Zip Code
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
131 Woodlake Wynde, Oldsmar
$154,500
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Woodlake Run SubDv. ⋅ 34677 Zip Code
AMAZING POTENTIAL in East Lake Woodlands, NON-Flood Zone and your Cable, Internet & Water is included in the HOA! This accessible first-floor condo is a fantastic opportunity to create your forever dream space. Located directly across from the heated community pool, this condo bursts with potential and is located in a highly desirable central location within the East Lake Woodlands community. Enjoy both your screened-in front and back patios, providing two comfortable outdoor spaces to relax and enjoy nature without the bugs! Inside, you’ll find tile flooring throughout, a spacious living room and dining room combo with a wet bar, and an open kitchen with plenty of extra counter seating. The washer and dryer are conveniently located right outside the kitchen in the front patio laundry closet, and being on the first floor means easy access with no stairs to navigate. This guard-gated community offers a peaceful setting surrounded by mature landscaping and wildlife, and if you decide to join the Ardea club, the main clubhouse, golf course, and tennis courts are right across the street. The HOA fee includes: Cable TV, Internet, Water, Community Pool, Escrow reserves, Maintenance Exterior, Roof, Grounds Maintenance, Security and Trash. East Lake Woodlands is home to the Adrea Country Club offering a variety of optional memberships for homeowners to join. These exclusive amenities include Two Championship 18-hole Golf Courses, Tennis and Pickleball Courts, Clubhouse Bar, Casual and Fine Dining, Fitness Center, Splash Pad, Swimming Pools, Clubhouse Events and more. Centrally located near top-rated schools, trending restaurants, shopping, movies, parks, Tarpon Lake, Gulf Coast beaches, local hospitals, Tampa Airport and more, you’ll never run out of activities in town!

131 Woodlake Wynde, Oldsmar
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