Oldsmar Homes with Pool Amenities

Oldsmar Homes with Pool Amenities

Welcome to Oldsmar, Florida—a hidden gem nestled in the heart of Pinellas County. With its rich history, vibrant community, and stunning natural landscapes, Oldsmar offers a perfect blend of small-town charm and modern conveniences. Just a stone's throw away from the beautiful Gulf Coast, residents enjoy easy access to pristine beaches, lush parks, and a variety of recreational activities, making it an ideal place for families and outdoor enthusiasts alike.

One of the standout features of Oldsmar is its diverse array of homes, particularly those boasting luxurious pool amenities. Imagine stepping into your backyard oasis, where a sparkling pool awaits, providing a refreshing escape from the Florida sun. These homes not only offer a place to cool off but also serve as the perfect setting for entertaining friends and family, hosting summer barbecues, or simply enjoying a serene evening under the stars.

Oldsmar's real estate market features a variety of properties, from cozy single-family homes to spacious estates, all equipped with the sought-after pool amenities that enhance your living experience. Whether you're seeking a tranquil retreat or a lively social hub, you'll find homes that cater to your every need.

With its friendly atmosphere, excellent schools, and a plethora of dining and shopping options, Oldsmar is more than just a place to live—it's a community where you can thrive. Explore the available homes with pool amenities today and discover why Oldsmar is the perfect place to call home!

Newest Oldsmar Homes with Pool Amenities

380 Rosalind Lane, Oldsmar
$569,999
3 Beds ⋅ 3 Baths ⋅ Bay Arbor SubDv. ⋅ 34677 Zip Code
Virtually Staged. PRICED TO SELL!!! Make your appointment now as it will sell quickly at this price! Plus this house has 400 sq. ft. MORE than most homes on market in the neighborhood and there are no back yard neighbors! Enjoy the comfort and character of this beautifully maintained 3 bedroom, 2.5 bath home tucked away on a quiet cul-de-sac in the gated Bay Arbor community of Oldsmar. Set on a wooded lot with no rear neighbors, this inviting two-story home blends classic architectural details with modern updates and thoughtful touches throughout. Recent improvements include a NEW AC (2026), NEW ROOF (2022), NEW screen enclosure (2024) and Impact-Resistant Hurricane Windows (2022)! This house is ready to move in with all the major updates necessary for peace of mind!. Inside, high ceilings and an open upstairs overlook create an airy sense of space, while porcelain tile and wood flooring, decorative chandeliers, and a gorgeous dark-stained staircase add character and style. The main floor offers a combination living and dining room, along with a spacious kitchen, dinette, and family room combination designed for everyday living and entertaining. The updated kitchen features clean, crisp cabinetry in a functional U-shaped layout, quartz countertops, stainless steel appliances, and a convenient breakfast bar with additional seating. Just beyond, sliding glass doors connect the family room to the partially covered, screened patio, where decorative brick pavers create an inviting outdoor space to relax or gather with friends and family. Beyond the patio, a large vinyl-fenced backyard backs to a wooded setting, providing added privacy and a peaceful backdrop. Upstairs, a spacious bonus room or loft provides additional flexibility for a media room, home office, or second living area. The conveniently located laundry room and all three bedrooms are also on the second floor. The generously sized primary suite features a walk-in closet and an updated, spa-like ensuite bath complete with a dual-sink vanity, soaking tub, and separate shower. Two additional spacious bedrooms share a full guest bathroom and shower. Bay Arbor offers a desirable gated neighborhood setting with a community pool, playground, and recreational facilities, while the surrounding Oldsmar area provides plenty of opportunities to enjoy the outdoors. Nearby attractions include Mobbly Bayou Wilderness Preserve and Mobbly Beach Park, along with miles of walking and biking trails, waterfront recreation, and local dining and shopping. With its combination of thoughtful updates, versatile living spaces, private backyard setting, and convenient location, this home offers a wonderful opportunity to enjoy all that Oldsmar and the Tampa Bay area have to offer!

380 Rosalind Lane, Oldsmar
166 Manta Circle, Oldsmar
$234,900
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Spacious 1992 Jacobsen home with 1,444 square feet of living area, now available in the desirable 55+ Gull-Aire Village community. Ideally located on Manta Circle, this home features an open floor plan that is perfect for entertaining, a bonus room suitable for a home office or den, a large indoor laundry room, and new baseboards throughout. Recent updates include a TPO roof and windows installed in 2020, a new water heater installed in 2025, and a new air-conditioning system installed in 2019 with a warranty contract through 2028. The exterior was freshly painted in October 2026. Additional features include two storage sheds for bikes, tools, or workshop space and a welcoming screened porch at the front of the home. Gull-Aire Village offers an active, well-maintained, pet-friendly community with a vibrant clubhouse, heated pool and spa, pool table, shuffleboard, bocce ball court, bingo, card games, line dancing, and other regular activities. Golf-cart-friendly streets make getting around the neighborhood easy and enjoyable. The HOA fee is just $70 per month, and ownership includes the land—there is no lot rent. Conveniently located across from AMC Theatres, Bealls, Marshalls, Ulta Beauty, PetSmart, Five Below, and Dollar Store, with numerous dining options nearby, including Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eves Family Restaurant. Super Walmart, Publix, and Countryside Hospital are approximately 10 minutes away. Enjoy easy access to a scenic canal-side biking and walking trail within the community, as well as the beautiful beaches of Honeymoon Island and Caladesi State Park, approximately ten miles away. Room sizes are approximate.

166 Manta Circle, Oldsmar
303 Vaudeville Row, Oldsmar
$666,625
3 Beds ⋅ 4 Baths ⋅ Odeon SubDv. ⋅ 34677 Zip Code
Under Construction. The Soprano is a three-story townhome offering modern luxury in the heart of Downtown Oldsmar. Thoughtfully designed for a flexible lifestyle, this beautifully appointed residence features luxury vinyl plank flooring throughout the entire home, including all staircases, creating a seamless design. The first floor welcomes you to a spacious two-car garage and a unique live/work space perfect for a home office, fitness room, or guest space. The first-floor half bath also has the option to convert into a full bathroom, adding more flexibility. The main living level showcases an expansive open-concept design with a spacious living and dining area flowing effortlessly into a gourmet kitchen. The space features a large center island, quartz countertops, gray cabinetry, tile backsplash, and Kohler fixtures. A generous flex room and full bath provide possibilities for a home office, fitness space, or media room. Two spacious outdoor living spaces create additional space for hosting or relaxing. The third floor offers a primary suite complete with a walk-in closet, private balcony, and spa-inspired bath featuring floor-to-ceiling tile, quartz countertops, and gray cabinetry. Two additional bedrooms share a well-appointed full bath with designer finishes, while a conveniently located laundry room adds everyday convenience. This home is under construction, and the photos shown are of a previously built home. For more details, please contact our sales team.

303 Vaudeville Row, Oldsmar
109 Lakeside Drive, Oldsmar
$199,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Welcome to this stunning, ground floor 2 bedroom to 2 bath condo in a guarded and gated community of East Lake Woodlands, where you can enjoy a maintenance-free Florida living at its best. Step inside and discover the seamless combination of quality updates with comfort. The spacious living and dining areas flow seamlessly together, creating an inviting, open atmosphere perfect for entertaining or simply relaxing at home. The well-appointed kitchen features a breakfast nook, convenient breakfast bar with a pass-through to the dining area, making both casual meals and gatherings a breeze. The desirable split-bedroom floor plan provides privacy, while the generously sized primary suite is a true retreat, featuring THREE walk-in closets! Additional highlights include plantation shutters throughout, living room fireplace, and an enclosed, all-weather Florida room overlooking a pond. Imagine starting your mornings with coffee while enjoying the serene water views or unwinding in the evening surrounded by nature. Enjoy the convenience of a lock-and-leave Florida lifestyle, with monthly condo fees covering basic cable, internet, water, sewer, and trash removal. Less time worrying about maintenance means more time enjoying everything Florida has to offer! Nestled within the well-established East Lake Woodlands community, residents enjoy the comfort of guarded entry. For those seeking an active, resort-inspired lifestyle, optional membership to Ardea Country Club offers access to golf, tennis, pickleball, fitness facilities, clubhouse amenities, and more. Location is another standout feature! Conveniently situated near shopping, restaurants, parks, entertainment, and everyday essentials, with easy access to Tampa International Airport and St. Pete-Clearwater International Airport. Whether you're looking for a full-time residence or a seasonal Florida getaway, this exceptional ground-floor condo checks all the boxes! Beautiful updates, spacious living, pond views, and a sought-after gated community make this an opportunity you won't want to miss. Come experience the charm, comfort, and convenience of East Lake Woodlands living!

109 Lakeside Drive, Oldsmar
238 Pelican Drive N, Oldsmar
$196,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Virtually Staged. Discover the perfect blend of comfort, convenience and coastal charm in this beautifully maintained, move-in ready, 2-bedroom, 2-bathroom, nestled in the heart of Oldsmar, Florida! Featuring a relaxed coastal vibe, this inviting home offers spacious living, dining and kitchen areas, newer stainless-steel appliances, updated bathroom vanities, beautiful laminate flooring, updated subflooring throughout, fresh paint throughout, a newer vapor barrier, and an open-concept layout. The generously sized primary suite features a spacious walk-in closet, an en-suite bathroom, with a separate garden-like tub, a separate water closet with walk-in shower creating a comfortable space to unwind. 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.)

238 Pelican Drive N, Oldsmar
411 Vaudeville Row, Oldsmar
$586,746
3 Beds ⋅ 3 Baths ⋅ Odeon SubDv. ⋅ 34677 Zip Code
Under Construction. The Baritone is an elegant three-story townhome offering modern luxury and versatility in the heart of Downtown Oldsmar. Thoughtfully designed for today's lifestyle, this beautifully appointed residence features luxury vinyl plank flooring throughout the entire home, including all staircases, creating a seamless design from top to bottom. A welcoming covered front porch and foyer entry lead to a garage and additional covered parking. The main living level showcases an expansive open-concept design with a spacious living and dining area flowing effortlessly into a gourmet kitchen. The space features a large center island, quartz countertops, gray cabinetry, a tile backsplash, pot filler, and striking Kohler fixtures. A generous flex room and full bath on this level provide possibilities for a home office, fitness space, or media room. The third floor offers a luxurious primary suite complete with a walk-in closet and spa-inspired bath featuring floor-to-ceiling tile, quartz countertops, gray cabinetry, and sleek Kohler fixtures. Two additional bedrooms share a well-appointed full bath with designer finishes and Kohler faucets, while a conveniently located laundry room adds everyday convenience. This home is under construction, and the photos shown are of a previously built home. For more details or to schedule a visit, please contact our sales team.

411 Vaudeville Row, Oldsmar
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
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
151 Lakeview Way Unit 151, Oldsmar
$189,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Virtually Staged. WATERFRONT, GROUND FLOOR, UPDATED and MOVE-IN READY! Enjoy one of the most peaceful, nature-filled views in the highly sought-after East Lake Woodlands community from this beautifully updated 2-bedroom, 2-bath condo with assigned COVERED PARKING. Step inside to a spacious, open layout with NO CARPET and plenty of natural light. The updated kitchen features NEW GRANITE COUNTERTOPS, NEW CABINETS, a pantry closet, generous storage, and a large breakfast bar overlooking the dining and living areas. The inviting living room features a cozy WOOD-BURNING FIREPLACE, perfect for those occasional cool Florida evenings. Sliding glass doors from BOTH the living room and primary suite open to the tiled lanai, creating a wonderful extension of the living space and the perfect place to enjoy your morning coffee while taking in the tranquil WATERFRONT VIEW and surrounding wildlife. The spacious primary suite features QUARTZ COUNTERTOPS, WALK-IN SHOWER, and a stylish NEW BARN DOOR. The guest bathroom includes a newer vanity, and both bathrooms feature NEW ELONGATED CHAIR-HEIGHT TOILETS installed in 2023. You'll also appreciate the abundance of closet and storage space throughout the home. Additional updates include a NEW A/C IN 2023, NEW BLINDS IN 2023, NEW CEILING FANS, laminate flooring in both bedrooms, and ceramic tile throughout the remainder of the condo, including the lanai. Assigned covered parking is included, along with plenty of additional guest parking. The community HEATED POOL is just a short walk away for year-round enjoyment. East Lake Woodlands offers a beautiful, gated country club setting surrounded by mature landscaping, lakes, and natural Florida scenery. Optional club memberships provide access to additional amenities that may include golf, tennis, fitness, dining, pools, and clubhouse facilities. Conveniently located near shopping, restaurants, parks, beaches, and Tampa International Airport. GROUND FLOOR + WATERFRONT VIEW + UPDATED INTERIOR + COVERED PARKING + NO CARPET = Florida living made easy!

151 Lakeview Way Unit 151, Oldsmar
389 Tranquil Court, Oldsmar
$179,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Just listed in 55+ Gull-Aire Village! Experience peaceful living in a quiet location surrounded by friendly neighbors. The open floor plan highlights stylish laminate, vinyl, and newly upgraded carpet flooring, complemented by newer stainless-steel appliances and high-end front-load washer and dryer. Enjoy peace of mind with a new AMS roof-over installed in July 2022, a new A/C from 2020, and a new vapor barrier added in 2017. The spacious living room features a built-in bar, perfect for entertaining guests or relaxing at home. With mobile home titles retired in August 2021, there are no transfer costs for the new owner. This vibrant community offers a clubhouse at its center, hosting monthly events and amenities including a pool table, shuffleboard, bocce ball courts, a heated pool, and a spa. Residents can participate in activities like bingo, card games, and line dancing, fostering an active and social lifestyle. Golf cart-friendly streets make neighborhood travel both easy and enjoyable. Enjoy affordable living with HOA fees of only $70 per month in a meticulously maintained community. Pet owners are welcome—one pet of any size is allowed, and a second pet may be permitted with an emotional support letter from a physician. Ownership includes the land, so you will not have to worry about lot rent. Convenience is right at your doorstep, with AMC Theatres, Bealls, Marshalls, Ulta Beauty, PetSmart, Five Below, and Dollar Store just across the street. Dining options abound, including Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eves Family Restaurant. Major retailers such as Super Walmart and Publix, along with Countryside Hospital, are only ten minutes away. Outdoor lovers will appreciate being just ten miles from the breathtaking beaches at Honeymoon Island and Caladesi State Park, as well as direct access to a scenic biking and walking trail along the canal. Room measurements are approximate.

389 Tranquil Court, Oldsmar
82 Pelican Drive N, Oldsmar
$179,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Welcome to Gull-Aire Village 55+, where this well-maintained 1993 Jacobsen home is ready for its new owner. Ideally located within walking distance of restaurants, shopping, and everyday conveniences, this home offers both comfort and convenience. Recent updates include a TPO roof installed by All Weather Roofing in August 2020, a new dishwasher installed in December 2024, and a new exterior 150-amp electrical panel with updated grounding installed in September 2018.The kitchen includes a convenient breakfast bar, perfect for enjoying morning coffee or entertaining guests. Both bathrooms have updated cabinetry, and the hall bathroom features a tiled shower. This home has an interior laundry with washer and dryer. Enjoy the desirable front screened porch, conveniently located at the same level as the home with no steps. The vibrant clubhouse serves as the heart of the community offering monthly events and amenities including a pool table, shuffleboard, bocce ball court, heated pool and spa. Residents can also participate in regular activities such as bingo, card games, and line dancing. Golf-cart-friendly streets make navigating the neighborhood easy and enjoyable. With HOA fees of just $70 per month, Gull-Aire Village offers affordable living in a well-maintained, pet-friendly community. One pet of any size is permitted, and a second pet is allowed with an emotional support letter from a doctor. Best of all, ownership includes the land, so there is no lot rent. Convenience is right across the street with AMC Theatres, Bealls, Marshalls, Ulta Beauty, PetSmart, Five Below, and Dollar Store nearby. Dining options include Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eves Family Restaurant. Super Walmart, Publix, and Countryside Hospital are approximately 10 minutes away. Outdoor enthusiasts will appreciate being just ten miles from the beautiful beaches of Honeymoon Island and Caladesi State Park, as well as having easy access to a scenic canal-side biking and walking trail from within the community. Room sizes are approximate.

82 Pelican Drive N, Oldsmar
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