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

$199,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Welcome to this beautiful 2-bedroom, 2-bathroom ground-floor condo in the highly sought-after East Lake Woodlands community. Built in 1979 with durable masonry construction and a slab foundation, this charming residence offers the perfect blend of comfort, character, and convenience. Enjoy peaceful pond views from the rear of the home while being surrounded by the outstanding amenities this master-planned community has to offer, including golf courses, nature trails, swimming pools, and a clubhouse. Ideally located between Hillsborough and Pinellas Counties, you'll have easy access to an incredible selection of shopping, dining, entertainment, and Gulf Coast attractions. Inside, timeless elegance shines through with beautiful oak flooring, a cozy wood-burning fireplace, and a convenient pass-through from the kitchen to the living area, creating an open and inviting space for everyday living or entertaining. The in-unit utility closet includes a washer and dryer for added convenience, while the generous closet space provides exceptional storage rarely found in condominium living. A covered parking space located directly in front of the unit makes unloading groceries and staying dry during Florida's afternoon showers a breeze. Whether you're looking for a year-round residence, a seasonal retreat, or an investment opportunity, this exceptional condo offers the best of maintenance-free living in one of the area's most desirable gated communities. Come experience the beauty and lifestyle of East Lake Woodlands and make 205 Martha Lane your new home!

205 Martha Lane Unit 205, Oldsmar
$300,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
163 Dolphin Drive, Oldsmar, FL Welcome to one of the standout homes in Gull-Aire Village, Oldsmar's highly sought-after 55+ community. Situated on a desirable corner lot, this beautifully renovated 2-bedroom, 2-bathroom home combines modern style with comfortable, low-maintenance living. From the moment you arrive, you'll appreciate the spacious two-car carport, attractive curb appeal, and thoughtful updates throughout. Inside, the open-concept floor plan creates an inviting space where the living room, family room, dining area, and beautifully remodeled kitchen with quartz counters and stainless steel appliances flow seamlessly together—ideal for everyday living or entertaining family and friends. The kitchen serves as the heart of the home with its contemporary finishes, generous workspace, and open sightlines to the main living areas and plenty of bright lighting. Both bedrooms are well-proportioned, and the updated bathrooms reflect the same quality craftsmanship found throughout the home. Outdoor living is just as impressive. The covered rear patio has been thoughtfully designed and is ready for your dream outdoor kitchen, creating the perfect setting for relaxing, dining, or hosting gatherings year-round. An attached storage shed provides plenty of room for tools, hobbies, seasonal décor, or golf cart accessories. Life in Gull-Aire Village offers more than just a beautiful home—it offers an exceptional lifestyle. Residents enjoy a vibrant calendar of social events, clubs, activities, and community gatherings throughout the year, making it easy to meet neighbors and stay engaged. The community's golf cart-friendly streets make it convenient and enjoyable to travel to the clubhouse, amenities, and visit with friends. Conveniently located near shopping, restaurants, medical facilities, parks, beautiful Gulf Coast beaches, Tampa International Airport, and the charming downtowns of Oldsmar, Safety Harbor, and Dunedin, you'll have easy access to everything the Tampa Bay area has to offer. If you've been searching for a move-in ready home where every detail has already been completed, 163 Dolphin Drive is an exceptional opportunity. Beautifully updated, thoughtfully designed, and located in one of Oldsmar's most welcoming communities, this home is truly one of Gull-Aire Village's finest.

163 Dolphin Drive E, Oldsmar
$245,000
2 Beds ⋅ 2 Baths ⋅ Sheffield Village At Bayside Meadows SubDv. ⋅ 34677 Zip Code
This spacious and well maintained 2-bedroom, 2-bath end unit Villa offers a comfortable floor plan and easy, worry-free living right in the heart of Oldsmar. With nearly 1,300 square feet and vaulted ceilings, the home features all tile flooring throughout, a large kitchen with plenty of cabinetry and a breakfast bar, plus an open family/dining area. The living room includes a cozy fireplace, creating a warm focal point for the space. Sliders lead to an enclosed porch, perfect for relaxing or enjoying morning coffee. An interior laundry closet adds everyday convenience. Major system upgrades provide excellent long-term value and peace of mind: • New roof (2021) • New HVAC (2024) • New water heater (2024) • New electrical panel (2024) • Impact windows (2016) • Sliding glass door (2018). A rare and highly desirable bonus is the two assigned covered parking spaces steps from your front door—a standout feature in this community and a true benefit for owners. Community amenities include a sparkling pool, and you’re just down the street from Sheffield Park, featuring tennis and basketball courts, a playground, dog park, fishing, disc golf, exercise stations, walking paths, and more. With low HOA fees of $110/month, including lawn maintenance, you’ll have plenty of time to enjoy the pool and Oldsmar’s interconnected parks. You’re also steps from Harbor Palms Nature Park and Preserve and the Oldsmar Trail, an 11-mile trail popular with bicyclists and joggers —perfect for nature walks, wildlife viewing, and beautiful sunsets. Nearby conveniences include athletic fields, shopping, dining, and world class beaches. This Villa is a well-cared for home with major updates already completed, offering comfort, convenience, and the best of Florida living.

2060 Sheffield Court, Oldsmar
$250,000
2 Beds ⋅ 2 Baths ⋅ St Andrews Condo SubDv. ⋅ 34677 Zip Code
Discover this beautifully remodeled GROUND-FLOOR END UNIT in the highly sought-after Saint Andrews community of East Lake Woodlands. Located just steps from the community pool, one of the largest in the area, this condo offers resort-style living. East Lake Woodlands is home to top-rated schools and an optional Ardea Country Club membership, providing access to two championship golf courses, 12 tennis courts, a pickleball complex, a fitness center, and an on-site restaurant. Overlooking the 18th hole of the North Course, this move-in ready condo offers breathtaking golf course views and a beautifully updated interior. Recent upgrades include new shaker kitchen cabinets, granite countertops, luxury vinyl plank flooring in both bedrooms, fresh interior paint, and stylish light fixtures. The spacious kitchen features ample storage and a cozy breakfast nook, while the open living and dining area is filled with natural light from oversized sliding glass doors leading to a screened porch overlooking the course. The split-bedroom floor plan provides privacy, and the primary suite includes a walk-in closet, double vanity, soaking tub, and private porch access. Relax on the screened lanai and enjoy peaceful golf course views, beautiful sunsets, and Florida's natural beauty. With modern updates, an ideal layout, and an unbeatable location, this condo offers the perfect blend of comfort and convenience

121 Lindsay Lane Unit 31, Oldsmar
$229,500
2 Beds ⋅ 3 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
Welcome to this 2-bedroom, 2.5-bath townhome located in the desirable gated community of Countryside Key in the heart of Oldsmar. This spacious floor plan features two primary suites upstairs, each with its own private bathroom, while the convenient half bath downstairs is perfect for guests. Enjoy an open living and dining area with plenty of natural light and a private screened patio ideal for relaxing or entertaining. The seller is offering a concession toward new flooring and/or appliances, providing a great opportunity to personalize the home to your own style. Residents of Countryside Key enjoy access to a community pool, tennis courts, and beautifully maintained grounds, all just minutes from shopping, dining, parks, top-rated schools, Tampa International Airport, and the beaches.

366 Countryside Key Boulevard, Oldsmar
$149,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Maintenance free condo living within the prestigious gates of East Lake Woodlands! Pride of ownership abounds in this well maintained first floor unit offering just under 1,100 sq ft of fine Florida living with 2 bedrooms, 2 bathrooms and a convenient covered carport. Open concept floor plan with a great room that combines living and dining spaces ideal for family gatherings and entertaining. Living and entertaining space is extended outside with sliding glass doors leading to a lanai looking out on the community’s well-manicured green spaces. A serene setting for morning coffee or afternoon cocktails. The lanai also houses a convenient storage closet. The spacious kitchen includes an eat-in area and features tile flooring. The appliances include a ceran top range, built-in microwave, refrigerator (5 yrs old) and dishwasher. Privacy prevails with an ideal split bedroom layout. The primary bedroom is located just off the living room and offers generous storage boasting 2 walk-in closets and an additional wall closet and the room offers a sliding glass door to the lanai. The ensuite features a single vanity with dressing area and a walk-in shower. The secondary bedroom is located on the opposite side of the home and features laminate flooring, a wall closet & ceiling fan. The hall bathroom is designed with a single vanity and a tub/shower combination. The hallway laundry closet is perfectly situated for ideal convenience, and the seller is generously including the washer and dryer. Additional features include AC 2022, WH 2022. The HOA includes exterior and grounds maintenance, community pool, water, sewer, trash, cable, internet. This condo is just steps away from the community pool! The home is zoned for exceptional schools and near to all, restaurants, shopping, medical and of course the famed Gulf beaches are nearby. The recently renovated Ardea Country Club lies within the gates of East Lake Woodlands. The club offers several levels of membership and has an impressive array of amenities including 2 championship golf courses, 2 resort style heated pools, 12 pickleball courts, 14 clay tennis courts, state-of-the-art fitness center, restaurant and bar. Magnificent home in a convenient location… carefree Florida living!

129 Nancy Drive, Oldsmar
$530,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
Endless sunsets create this picture perfect location in Seaside Estates, situated on Old Tampa Bay, where everyday living feels like a vacation. This townhome has 3 bedrooms, 3 bathrooms, and 1,834 square feet of thoughtfully designed living space. Upstairs on the main living level, high ceilings, skylights, and oversized windows frame breathtaking open-water views and unforgettable sunsets. A spacious bedroom with a full bath is also located on this level, ideal for guests or flexible living. The top floor is home to the owner’s suite retreat, complete with a private balcony, double walk-in closets, a garden tub, separate shower, and dual vanities. An additional bedroom with a full bath and a conveniently located laundry area complete the upper level. The first level features a tandem 3 car garage offering enough space to store your water toys and vehicles. There is newly installed epoxy flooring, extra storage under the stairs, and a covered patio perfect for a grill. A deeded boat slip with a new 7000lb. electric lift is right outside the unit. Just steps from the pool, spa, and tennis courts, this community invites an active waterfront lifestyle. Launch a kayak into nearby mangroves, stroll the expansive boardwalk while watching dolphins and manatees, or enjoy the heated pool, playground, picnic areas, and harbor views. With minimal pet restrictions and HOA fees that include roof, exterior paint, water, sewer, exterior insurance, trash and amenities, living here is truly effortless. Located in the heart of Oldsmar, you’re just steps from R.E. Olds Park, a 15-acre waterfront park offering sweeping views of Tampa Bay. From seasonal festivals and community events to a 400-foot fishing pier and playground, this vibrant park is truly an extension of your neighborhood. With Pinellas beaches, Tampa International Airport, and downtown Tampa all nearby, you’ll enjoy easy access to everything the Tampa Bay area has to offer.

158 Brent Circle, Oldsmar
$247,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Experience the charm of Gull-Aire Village 55+ in this beautifully renovated home, ready for its next owners. Boasting a spacious 1,320 square feet with stylish laminate flooring throughout, this residence is perfect for entertaining and comfortable living. The split-bedroom layout ensures privacy for both you and your guests, while both bathrooms feature luxurious walk-in showers for added convenience. The Chefs kitchen is a culinary delight, featuring an inviting island, sleek granite countertops, and an abundance of cabinets for optimal storage. Adjacent to the kitchen, the dining area impresses with built-in cabinetry, ideal for a coffee bar or entertaining bar. Elegant barn doors lead from the dining area into the cozy family room, where the indoor laundry—complete with washer and dryer—offers practicality and ease. Carport offers side-by-side parking. Embrace an active lifestyle at the vibrant clubhouse, the heart of the community, events and offering amenities such as a pool table, shuffleboard, bocce ball court, and a heated pool and spa. Stay engaged with regular activities. Golf cart-friendly streets make navigating the neighborhood effortless! Enjoy affordable living with HOA fees at only $70 per month. Bring one pet of any size, and a second pet is allowed with a doctor's note for emotional support. Best of all, you own the land. Conveniences are at your fingertips, like AMC Theatres, Bealls, Marshalls, PetSmart, Five Below, and Dollar Store just across the street. Savor local flavors at Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eve's Family Restaurant. Essential retailers such as Super Walmart and Publix, along with Countryside Hospital, are only minutes away. Outdoor enthusiasts will love the proximity to the stunning beaches of Honeymoon Island and Caladesi State Park, just ten miles away. A scenic biking and walking trail along the canal are easily accessible from within the community. Room sizes are approximate. Do not miss your chance to experience the best of Oldsmar living in one of the area’s most sought-after communities.

407 Dolphin Drive S, Oldsmar
$216,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Welcome home to this beautifully updated second-floor condo located in the highly sought-after, gated community of East Lake Woodlands with picturesque golf course views. Known for its peaceful surroundings and resort-style living, this community offers both comfort and convenience in an ideal setting. You are greeted by a new storm door before stepping inside to discover a bright and airy interior filled with natural light. This move-in-ready residence has been thoughtfully upgraded with an amazing eat-in kitchen featuring new quartz countertops, a closet pantry, newer appliances (only two - four years old), and Wi-Fi-compatible dishwasher and range—perfect for everyday living and entertaining alike with a convenient pass-through window to the dining area. Fresh interior paint and new LVP and tile flooring flow seamlessly throughout the home, complemented by energy-efficient LED lighting, ceiling fans, and updated bathrooms for a clean, modern, and cohesive design. The home also features upgraded, HOA-approved Stainmaster LVP underlayment for the LVP flooring, providing enhanced comfort and sound reduction. The air conditioning system is equipped with a UV light for improved air purification and indoor air quality. The spacious primary bedroom offers three closets, including two walk-in closets, a separate dressing area, and an updated en-suite bathroom with a walk-in tiled shower and glass door. The guest bedroom features generous wall closets. A brand-new washer and dryer are scheduled to be installed in mid-August and are conveniently located in the hall closet near the guest quarters. Generous storage and ample closet space add to the home's functionality and overall comfort. Enjoy the added privacy of a second-floor location while taking advantage of the exceptional lifestyle within East Lake Woodlands. The community pool and Condo 2 Clubhouse are just across the parking lot! Pets are welcome, and the monthly maintenance fee provides outstanding value and ease of living. If you're ready to explore, the location is fantastic. Nearby, Ardea Country Club offers optional private memberships with two heated swimming pools, two 18-hole championship golf courses, tennis and pickleball courts, a fitness center, clubhouse, restaurants, and a full calendar of social activities. The condo is also conveniently located near Westfield Countryside Mall, shopping, restaurants, entertainment, the beautiful beaches of Honeymoon Island, and numerous parks and walking trails for a relaxed Florida lifestyle. You'll also enjoy easy access to the charming downtown districts of Tarpon Springs, Dunedin, and Safety Harbor for even more dining, shopping, and entertainment.

222 Caryl Way, Oldsmar
$665,000
3 Beds ⋅ 2 Baths ⋅ Parcel B - The Pinnacle SubDv. ⋅ 34677 Zip Code
RARELY AVAILABLE VILLA OPPORTUNITY IN PRIVATE PINNACLE COMMUNITY OF EAST LAKE WOODLANDS. "THIS IS A MAINTENANCE FREE COMMUNITY." WALK THRU DOUBLE GLASS ENTRY DOORS TO FOYER THAT OPENS TO LIVING ROOM. LIGHT AND BRIGHT EXPANDED FAMILY ROOM AND KITCHEN OFFERS QUIET VIEWS OF CONSERVATION AND GOLF COURSE AREA. NEWLY EXPANDED LANAI WITH PARORAMIC BIRDCAGE SCREENING. KITCHEN OVER LOOKS FAMILY ROOM HAS CENTER ISLAND AND WOOD CABINETRY, BUILT-IN PANTRY, GRANITE COUNTER TOPS AND ALL STAINLESS-STEEL APPLIANCES. SEPARATE DINING ROOM WITH EASY ACCESS FROM THE KITCHEN. MASTER BEDROOM WITH TWO WALK-IN CLOSETS AND MASTER BATH WITH FREE STAND TUB, SEPARATE STALL SHOWER, PRIVATE TOILET CLOSET, DOUBLE SINK VANTY WITH GRANITE COUNTER AND CUSTOM TILE. OFFICE WITH DOUBLE DOOR ENTRY CAN ALSO BE USED AS THIRD BEDROOM WITH CLOSET. SECLUDED SECOND BEDROOM IS PERFECT FOR GUESTS WITH ADJOINING BATH. INSIDE LAUNDRY ROOM WITH UTILITY SINK AND EXTRA STORAGE. GARAGE HAS EXTRA STORAGE AND SPACE FOR TWO CARS. THIS SEPTACULAR HOME LOCATED ON A PRIVATE CUL-DE-SAC. FOR SOCIAL ENJOYMENT YOU CAN RELAX IN THE COMMUNITY POOL. CLUBHOUSE MEMBERSHIP IS ALSO AVAILABLE FOR TENNIS AND GOLF. CLOSE TO BEACHES, SHOPPING, HOSPITALS, AND AIRPORTS. THIS IS WAITING FOR YOU!

5250 Pinehurst Court, Oldsmar
$399,000
3 Beds ⋅ 2 Baths ⋅ Heatherwood Unit One Condo SubDv. ⋅ 34677 Zip Code
Beautifully updated condo in East Lake Woodlands with 3 bedrooms, 2 full baths, 1 car garage and an added BONUS space/office! Right as you enter, notice the entire entryway is newly UPDATED with a custom door, paint, sconce lighting and Stanton carpet up the stairwell. Prepared to be wowed in the living room by the elegant, NEW custom built entertainment center with an electric fireplace. Set your color of choice and it can heat up the room for chilly nights. With the natural light, luxury vinyl plank flooring, vaulted ceilings, 2 huge fans on remotes.. this is quite the spot for entertaining. Kitchen features newer leathered granite countertops, wood cabinetry with soft close doors, stainless steel appliances, breakfast bar and new custom drapes. Step outside to the fully screened lanai with adjustable sunshades. Cool off with a new variable speed fan while enjoying all the wildlife East Lake Woodlands as to offer. The owner's suite also has a sliding door to the lanai, 2 closets with ample space, double bathroom vanities, countertops, garden tub and floor-to-ceiling tiled, glass-enclosed shower. Two other bedrooms with large windows share an updated bathroom. Enjoy an upstairs inside laundry with storage space and a bonus room with a convenient wet bar area. This space can be a TV room, office, playroom, sitting room for morning coffee..the ideas are endless. Additional updates include new epoxy garage floor, remote blinds, and light fixtures. Furniture is also available for purchase. East Lake Woodlands is central to Florida's most famous beaches, shopping, Tampa airport, A-rated schools and numerous dining options. There also is an option to join the Ardea Country Club and have access to 2 championship golf courses, tennis courts, fitness center, clubhouse, dining, swimming pools and social events. Don't miss this opportunity!

Oldsmar
$425,000
3 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Pinewinds SubDv. ⋅ 34677 Zip Code
One look and you'll be sold! This beautifully maintained, move-in-ready villa offers the perfect combination of comfort, privacy, and convenience. Featuring three bedrooms, two bathrooms, and an attached two-car garage, this home is sure to check all the boxes. Step inside to a spacious Great Room with soaring cathedral ceilings and a cozy wood-burning fireplace, creating the perfect space for relaxing or entertaining. The home's thoughtful layout and meticulous upkeep make it truly move-in ready. One of this property's most outstanding features is its premium location on one of the most private lots in all of East Lake Woodlands. With no rear neighbors, you'll enjoy exceptional privacy while overlooking a tranquil pond and wooded preserve. Start your mornings with coffee or unwind in the evenings with a glass of wine on the private screened lanai as you take in the peaceful views. Located on a quiet cul-de-sac in the desirable Pinewinds community within the gated East Lake Woodlands neighborhood, this home offers both security and a relaxed lifestyle. Residents enjoy convenient access to shopping, dining, beautiful Gulf beaches, medical facilities, parks, Tampa International Airport, and St. Pete–Clearwater International Airport. The HOA handles exterior maintenance, lawn care, and the community pool, allowing you to enjoy a true low-maintenance, resort-style lifestyle year-round. Whether you're searching for a full-time residence, a seasonal retreat, or a vacation getaway, this exceptional villa is an outstanding opportunity. Priced to sell, this home won't stay on the market for long. Schedule your private showing today before it's gone!

80 Summerwinds Lane, Oldsmar
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