Oldsmar Homes with Association Recreation - Owned Community Features

Oldsmar Homes with Association Recreation - Owned Community Features

Welcome to Oldsmar, Florida—a hidden gem nestled in the heart of Pinellas County. This charming city, located just a stone's throw away from the sparkling Gulf Coast, offers a perfect blend of suburban tranquility and vibrant community life. With its lush parks, scenic waterfront views, and a rich tapestry of local history, Oldsmar invites you to embrace a lifestyle that is both relaxing and engaging.

One of the standout features of Oldsmar is its array of homes within association recreation-owned communities. These neighborhoods provide residents with an exceptional quality of life, complete with well-maintained amenities that foster a sense of belonging. Imagine spending your weekends enjoying the community pool, participating in organized events, or taking leisurely strolls through beautifully landscaped grounds. The additional recreational facilities—such as tennis courts, fitness centers, and playgrounds—ensure that there’s something for everyone, making it easy to connect with neighbors and create lasting friendships.

Oldsmar is not just about beautiful homes; it’s about a vibrant community spirit. With an active calendar of events, from farmers' markets to seasonal festivals, residents can immerse themselves in the local culture. Plus, with easy access to nearby cities like Tampa and Clearwater, you can enjoy the best of both worlds—serene suburban living combined with urban excitement.

If you’re looking for a place that offers a welcoming community, fantastic recreational opportunities, and the beauty of Florida living, Oldsmar is the perfect choice. Come discover your dream home in this delightful city!

Newest Oldsmar Homes with Association Recreation - Owned Community Features

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code

Welcome to 428 Pelican Drive South in Gull-Aire Village, a welcoming 55+ golf cart friendly community in Oldsmar where you can enjoy the Florida lifestyle with room to spread out. This spacious 2-bedroom, 2-bathroom home offers large rooms, an indoor laundry area, and a desirable location toward the back of the community. Whether you’re looking for a full-time Florida residence, a seasonal retreat, or a comfortable place to enjoy your next chapter, this home offers the space and flexibility to make it your own. The generous room sizes provide plenty of opportunity for comfortable living, entertaining, hobbies, or welcoming visiting family and friends. The indoor laundry adds everyday convenience, while the peaceful setting toward the back of the community offers a welcome sense of privacy. It’s a wonderful opportunity to enjoy the ease of community living without giving up the space you desire. Located in Oldsmar, Gull-Aire Village offers the appeal of a Florida community with convenient access to shopping, dining, parks, and the many attractions of the Tampa Bay area. Come discover the possibilities at 428 Pelican Drive South and imagine making this spacious home your own. Gull Aire Village is an active community with an amazing line up of social events, community pool, clubhouse, and lots to do!

428 Pelican Drive S, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code

Welcome Home! Your beautifully updated move-in-ready Florida retreat with a warm, contemporary style awaits you in the heart of Oldsmar. This spacious 2-bedroom, 2-bath home with a den, (possible 3rd bedroom), 2-car garage home is situated on a beautifully landscaped lot, offering privacy, flexibility and plenty of space to enjoy the Florida lifestyle. The open and inviting floor plan features cathedral ceilings and newer, high quality laminate flooring throughout the living room, dining area, foyer, bedrooms, den and hallway. Ceramic tile flooring is featured in the kitchen, dinette, Florida room, laundry room and bathrooms. The well-appointed kitchen is designed for both everyday living and entertaining, featuring quartz countertops, stylish cabinetry, an island, stainless steel appliances - including a refrigerator, range, range hood and microwave - and a convenient pantry closet. The generous primary suite offers two walk-in closets and a private en-suite bathroom with a double sink vanity, walk-in shower and linen closet. The spacious Florida room overlooks the beautifully landscaped private backyard and can be accessed from the dinette area, living room or the primary bedroom. Plantation shutters throughout the dinette area and on the primary bedroom sliding glass door provides privacy. The covered screened-in porch features sleek aluminum railings and durable composite deck flooring providing both style and additional space for relaxing or entertaining. More recent upgrades include a roof replacement (2024), newer A/C system (2022), screened-in porch (2022), and water heater (2022). Nestled in the highly desirable 55+ community of Gull-Aire Village, this golf cart-friendly neighborhood offers exceptional 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.This home features a low monthly HOA fee of just $70 with one pet of any size permitted.The location is truly unbeatable! You're less than a mile from Woodlands Square, offering Bealls, Marshall’s, Ulta, PetSmart, AMC Theatres, Craft Street Kitchen, Shaker & Peel, Eve’s Family Restaurant, and more. Everyday conveniences such as Publix, Target, Walmart Neighborhood Market, and Mease Countryside Hospital are just 2 miles away. Honeymoon Island Beach is approximately 9 miles away, and Tampa International Airport is an easy 15-mile drive.An adjacent walking, running, and biking trail along Canal Way leads directly to picturesque Sheffield Park, providing the perfect setting to enjoy Florida’s outdoor beauty. Whether you’re socializing at the clubhouse, relaxing by the sparkling pool, or simply enjoying the peaceful surroundings, you’ll fall in love with the friendly, welcoming lifestyle of Gull-Aire Village.(Room dimensions are approximate and should be verified by Buyer.)

603 Canal Way, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code

This move-in-ready, well-maintained home is one of the larger homes in this golf-cart-friendly 55+ community and is being sold FURNISHED. The open floor plan features a spacious living room/dining room combination with luxury vinyl plank flooring and attractive plantation shutters, creating a clean, bright and inviting space. The kitchen offers white cabinetry, an updated countertop and a new range. Bathrooms have been updated also. Both bathrooms have been tastefully updated. Tons of storage spaces in the home. Another great feature is the washer and dryer located inside the home, rather than in the outside shed. The screened-in lanai is perfect for enjoying your morning coffee. Several important improvements have already been completed, including replacement windows in 2020, a vapor barrier in 2021 and a LeafGuard gutter system. AC ductwork replaced in 2025 and BRAND NEW WATER HEATER 2026! The Gull-Aire community has so much to offer! You own the land here and enjoy low monthly fees, along with a heated pool and spa, and an active clubhouse with tons of social activities. The location is convenient to just about everything—shopping, restaurants, grocery stores, AMC Theaters, and Mease Countryside Hospital. Woodlands Square Plaza is nearby, with Bealls, Marshalls, PetSmart and plenty of dining options, including Shaker & Peel, Craft Street Kitchen and Eve’s Family Restaurant. Outdoor recreation is close by as well, with walking trails, Chi Chi Rodriguez Golf Club, and pickleball at Sheffield Park. And don’t forget the beach! Beautiful Honeymoon Island is only 15 minutes away. Come see this great home and enjoy all that this convenient location has to offer!

392 Cobia Way, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code

Experience the exceptional lifestyle offered by this immaculate 1989 Jacobsen home—a true gem that blends modern updates with timeless charm. Step inside to a bright, open floor plan featuring soaring cathedral ceilings and elegant luxury tile flooring throughout. The beautifully textured walls and Key West-style plantation shutters add a touch of sophistication, while the newly installed 50-gallon hot water heater ensures efficiency and comfort. The kitchen has been thoughtfully updated with stunning quartz countertops, providing both style and functionality, and the expansive indoor laundry room boasts a brand-new washer and dryer, abundant storage, and convenience for daily chores. Retreat to the spacious primary suite, complete with a generously sized walk-in closet. The remodeled primary bathroom highlights a contemporary walk-in shower and sleek quartz countertop, while the guest bath has been upgraded with a custom shower and vanity for added luxury. Enjoy easy maintenance and impressive curb appeal, thanks to Shark Coating on the porch, driveway, walkway, and main entry. The substantial utility room is ideal for a workshop or extra storage. At the heart of this vibrant community, the clubhouse invites residents to monthly events and offers a wealth of amenities—including a pool table, shuffleboard and bocce ball courts, a heated pool, and a relaxing spa. Engage in regular activities like bingo, card games, and line dancing, fostering a lively and social atmosphere. Navigate the golf cart-friendly streets with ease and enjoy affordable living, with HOA fees at just $70 per month in a meticulously maintained neighborhood. Pet lovers are welcome: one pet of any size is permitted, and a second may be allowed with an emotional support letter from a physician. Ownership includes the land—no lot rent required. Conveniences are right at your doorstep, with AMC Theatres, Bealls, Marshalls, Ulta Beauty, PetSmart, Five Below, and Dollar Store just across the street. Savor a variety of dining options, including Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eve's Family Restaurant. Major retailers like Super Walmart and Publix, as well as Countryside Hospital, are only ten minutes away. Outdoor enthusiasts will appreciate being just ten miles from the breathtaking beaches at Honeymoon Island and Caladesi State Park, plus direct access to a scenic biking and walking trail along the canal. Room measurements are approximate.

214 Dolphin Drive N, Oldsmar

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

3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code

Endless sunsets create this picture-perfect location in Seaside Estates. Resting on the banks of 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. 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 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

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

2 Beds ⋅ 2 Baths ⋅ Meadows Of East Lake Woodlands SubDv. ⋅ 34677 Zip Code

Welcome to 106 Windward Place, a two bedroom two bathroom condominium located in the Meadows at East Lake Woodlands. One of Oldsmar‘s most sought after gated communities. This is a bank owned (REO) property, an excellent opportunity for homeowners, investors, or buyers looking to customize a home of their own taste. The functional floor plan features a spacious, living and dining area, split bedroom, layout, and a private setting within the community. The Meadows offers beautifully maintained grounds, mature landscaping, and a peaceful residential atmosphere. Residents enjoy convenient access to shopping, dining, golf, parks, Tampa International Airport and the Beautiful Gulf beaches. Whether you are searching for a primary residence, seasonal getaway or investment property 106 Windward Place offers outstanding value and the chance to own within the desirable East Lake Woodlands community. Property is being sold as is.

106 Windward Place, Oldsmar

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

"RESORT STYLE LIVING" in East Lake Woodlands! This beautifully maintained 2-bedroom,2-bath condominium offers approximately 1,151 sq ft of comfortable living space in one of Oldsmar’s most desirable gated communities. Major updates provide peace of mind, including flooring, A/C system, hot water heater, dishwasher, washer and dryer, and bedroom carpeting all approximately 3 years old, plus a refrigerator replaced in 2025. The open living and dining areas create an inviting space for entertaining, Move-in ready, thoughtfully designed and updated this home features a spacious layout, abundant natural light, and a screened lanai—perfect for enjoying Florida’s year-round lifestyle. Enjoy the convenience of covered parking and maintenance-free living. Residents enjoy access to a community pool, pool club house, beautifully maintained grounds, and optional country club amenities including golf, tennis, fitness, and social activities. Ideally located near shopping, dining, parks, beaches, Tampa International Airport, and top Pinellas destinations, this condo offers the perfect blend of convenience, value, and resort-style living. Whether you’re looking for a full-time residence, seasonal retreat, or investment opportunity, this East Lake Woodlands gem is one you won’t want to miss!

130 Nancy Drive Unit 37, Oldsmar

2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code

Welcome to effortless Florida living in this beautifully updated, move-in-ready 2-bedroom, 2-bath home located in one of Oldsmar’s most desirable 55+ active adult communities. From the moment you arrive, the pride of ownership is clear. Charming curb appeal, an oversized screened front porch, and a meticulously maintained exterior create the perfect first impression and set the tone for the easy, low-maintenance lifestyle so many active adults and seasonal residents are looking for. Step inside and you’ll immediately notice the thoughtful updates throughout. The true heart of the home is the stunning custom kitchen, designed for both everyday living and entertaining. It features elegant quartz countertops, a farmhouse sink, designer tile backsplash, premium custom cabinetry with dovetail soft-close drawers, and new Kitchen and Laundry flooring. This is a space that’s as beautiful as it is functional. The rest of the home is equally impressive, with upscale finishes including LED recessed puck lighting, crown molding, 2¼-inch baseboards, custom closet systems, and beautiful Bali Blinds that add both style and functionality throughout. The Primary and guest bathroom has also been tastefully renovated, and every room feels bright, welcoming, and exceptionally well cared for. Beyond the cosmetic updates, this home offers true peace of mind with major improvements already completed, including a newer roof (2017), A/C system (2014) with UV light added in 2020, energy-efficient double-pane windows (2014), an upgraded electrical panel with whole-home surge protection, and gutters with gutter guards. A standout feature is the upgraded marine-grade plywood subfloor, a rare detail that speaks to the level of care and quality invested in this home. The lifestyle here is just as appealing. Residents enjoy resort-style amenities with low HOA fees that include a heated pool and spa, clubhouse, library, billiards room, shuffleboard, bocce ball court, and separate men’s and women’s saunas. Boat and RV storage are also available for added convenience. The location is hard to beat. Situated in the heart of Oldsmar, directly across from shopping, dining, banking, entertainment, and everyday conveniences, you’re also just a short drive to Westfield Countryside Mall, Tampa International Airport, scenic parks, Safety Harbor, downtown Tampa, Clearwater, and the world-famous Gulf beaches. This turnkey 55+ retreat offers the perfect combination of comfort, convenience, and carefree Florida living. Schedule your private showing today.

276 Pelican Drive N, Oldsmar

3 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code

Now available in the sought-after 55+ Gull-Aire Village: a meticulously maintained 1995 Jacobsen home, offering over 1,400 square feet of comfortable living space. This inviting residence features three spacious bedrooms and two full bathrooms, with a split floor plan that provides privacy for guests. The home boasts a newly installed TPO roof (2024) that covers the main unit, Florida room, and carport, plus a hot water heater only two years old. Durable laminate flooring flows throughout, enhancing the bright and airy interiors. The generous eat-in kitchen includes an indoor laundry area with washer and dryer, while sliding glass doors lead to the Florida room—conveniently situated at the same level as the main house, eliminating any steps. The primary bathroom is equipped with double sinks and a shower for added comfort. Enjoy the vibrant community lifestyle at the clubhouse, which hosts monthly events and offers amenities such as a pool table, shuffleboard, bocce ball court, heated pool, and spa. Stay active and engaged with regular activities including bingo, cards, and line dancing. Navigating the neighborhood is easy thanks to golf cart-friendly streets! With HOA fees at just $70 per month, experience affordable, carefree living in a beautifully maintained community. This pet-friendly neighborhood welcomes one pet of any size, with a second pet permitted upon receipt of an emotional support letter from a doctor and submitted with your HOA application. Ownership includes the land—no lot rent required. Daily conveniences are just steps away, with AMC Theatres, Bealls, Marshalls, Ulta Beauty, PetSmart, Five Below, and Dollar Store across the street. Dine at popular spots like Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eves Family Restaurant. Major retailers, Super Walmart and Publix, as well as Countryside Hospital, are approximately 10 minutes from your door. Outdoor lovers will appreciate easy access to the scenic biking and walking trail along the canal, as well as the breathtaking beaches of Honeymoon Island and Caladesi State Park just ten miles away. Room sizes are approximate. Do not miss your chance to own this outstanding home in Gull-Aire Village—schedule your showing today!

258 Pelican Drive N, Oldsmar

3 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Cluster Homes SubDv. ⋅ 34677 Zip Code

Back on the market. Fresh and ready to go! Spacious 3-bedroom, 2-bath villa offering 1,385 square feet of comfortable living in desirable East Lake Woodlands. This home features ceramic tile throughout the main living areas and cozy carpet in the bedrooms. The bright living room is lined with sliding glass doors that open to a screened lanai spanning the full length of the villa—perfect for enjoying indoor/outdoor Florida living. The primary bedroom and third bedroom both feature private patio door access to the screened lanai, while ceiling fans in the bedrooms add extra comfort. Enjoy additional outdoor space with a fenced front patio, plus extra storage located on the screened lanai. Your covered carport includes an additional storage unit and comes with one assigned parking space.

260 Michaels Circle, Oldsmar

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