Refine Search
Sort by
258 Pelican Drive N, Oldsmar
$252,000
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

1815 Driftwood Circle S, Oldsmar
$414,900
3 Beds ⋅ 2 Baths ⋅ Harbor Palms-Unit Two SubDv. ⋅ 34677 Zip Code
This beautifully renovated three-bedroom, two-bath home sits in the heart of Oldsmar at the top of Tampa Bay. Fully updated inside and out, it offers a gorgeous new kitchen with stainless steel appliances, soft-close cabinets, leather-finished granite countertops, charming breakfast nook and even a premium electronic touchless kitchen faucet. All three bedrooms are thoughtfully spaced apart for extra privacy, with the spacious master suite featuring a massive California-style walk-in closet, serene backyard views, and a stunning bathroom with a walk-in shower. The open-concept living area flows into a roomy bonus space at the back of the house, highlighted by tandem ceiling fans. French doors open to a fully fenced backyard that is big enough for a future pool and there's even a poured slab ready for a shed. A large utility room with laundry features a utility sink and offers entry into the two-car garage that has a new hurricane-rated door and My-Q Wi-Fi opener. The home is completed by brand new impact resistant double-paned windows (that can get you discounts on insurance) and French doors as this reno was very thorough with every surface being refreshed including all of the ceilings, walls, plumbing and insulation. Situated in the heart of Oldsmar, this location offers quick and easy access to the beautiful Pinellas Beaches, the vibrant city of Tampa, and its own array of fantastic dining, top-notch schools, and great shopping. This home is definitely worth seeing!

1815 Driftwood Circle S, Oldsmar

2034 Montego Court, Oldsmar
$204,900
1 Beds ⋅ 1 Baths ⋅ Bayside Meadows Ph Ii SubDv. ⋅ 34677 Zip Code
Welcome to this spacious 1,028 sq ft villa in the desirable Bayside Meadows community of Oldsmar. This beautifully updated home offers the comfort and privacy of villa living with a one-car garage, fenced backyard, and screened lanai—perfect for enjoying Florida’s year-round outdoor lifestyle. The thoughtfully designed interior features a kitchen overlooking the living area, a cozy wood-burning fireplace, convenient wet bar, updated bathroom, newer washer and dryer, and beautiful hardwood and luxury vinyl flooring throughout. The spacious layout provides plenty of room for relaxing, entertaining, or creating your own comfortable retreat. Enjoy the convenience of a low-maintenance community with a pool and HOA fees that include lawn care. The private fenced backyard and screened lanai create a peaceful outdoor space for morning coffee, entertaining guests, or simply enjoying the Florida weather. Pets are welcome, and long-term rentals are permitted, providing added flexibility for future owners. Conveniently located near parks, shopping, dining, and recreation, including nearby Sheffield Park, with easy access to Tampa, Clearwater, and the surrounding Tampa Bay area. This villa is a great fit for first-time buyers, downsizers, seasonal residents, investors, or anyone seeking an easy-care Florida lifestyle in a convenient Oldsmar location.

2034 Montego Court, Oldsmar

10 Lesley Lane, Oldsmar
$279,000
2 Beds ⋅ 2 Baths ⋅ Quail Forest Cluster Homes SubDv. ⋅ 34677 Zip Code
Welcome to 10 Lesley Lane, located in the gated community of Quail Forest, nestled within the private country club community of East Lake Woodlands. This beautifully maintained end-unit villa offers serene pond views and a thoughtfully designed split-bedroom floor plan for added privacy and comfort. Major updates provide peace of mind, including a new roof (2022), HVAC (2023), and water heater (2018). The spacious, fully updated kitchen is a true highlight, featuring new cabinetry, sleek quartz countertops, and stainless steel appliances, perfect for both everyday living and entertaining. The layout flows effortlessly into the living and dining areas, all filled with natural light and peaceful water views. Enjoy your morning coffee or unwind in the evening on the charming front patio. Additional conveniences include one assigned carport and plenty of guest parking for visitors. Residents of East Lake Woodlands have access to two championship golf courses, consistently ranked among the top 5 in the entire Tampa Bay area, along with optional country club amenities. Ideally located near shopping, dining, parks, and just a short drive to Tampa International Airport and the Gulf beaches, this home offers the perfect blend of lifestyle and location. Don’t miss your opportunity to own in one of Oldsmar’s most desirable communities!

10 Lesley Lane, Oldsmar

108 Brent Circle, Oldsmar
$374,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
Welcome to coastal lifestyle living in one of Oldsmar’s most desirable gated waterfront communities called Seaside Estates. This beautifully maintained home offers the perfect blend of comfort, convenience, and outdoor living just minutes from Tampa Bay. Step inside to an open-concept floor plan filled with natural light, high ceilings, and spacious living areas designed for both everyday living and entertaining. Sliding glass doors create a seamless connection between indoor and outdoor spaces, while the private patio provides the perfect setting for relaxing evenings. The home features a spacious primary suite with ensuite bath, additional guest accommodations, and a flexible office or study space ideal for remote work or hobbies. The open kitchen flows naturally into the main living area, creating an inviting atmosphere for gatherings. Additional highlights include walk-in closets, a cozy fireplace, and an oversized tandem garage offering plenty of storage. Recent improvements include a new A/C system 2022 and water heater installed 2025, with roof updates completed in 2017, offering peace of mind for future homeowners. Residents enjoy exceptional community amenities including scenic waterfront boardwalks, fishing pier, kayak and small-boat access, and peaceful water views where dolphins and manatees are frequently seen. Walking trails, parks, playgrounds, and picnic areas create a relaxing park-like setting within the neighborhood. Conveniently located near Tampa International Airport, downtown Tampa, Ybor City, shopping, dining, and Gulf beaches, this home offers the perfect balance of tranquility and accessibility. Experience the best of Florida coastal living in Oldsmar.

108 Brent Circle, Oldsmar

1505 Sunset Wind Loop, Oldsmar
$380,000
3 Beds ⋅ 3 Baths ⋅ Bayside Terrace SubDv. ⋅ 34677 Zip Code
This beautiful townhouse (NEVER FLOODED) is located in the highly desirable waterfront gated community of Bayside Terrace. The home offers three bedrooms and two and a half bathrooms with a modern, open layout designed for comfortable living and entertaining. The 9 foot ceilings enhance the spacious feel and allow natural light to flow throughout the home. There is no immediate rear neighbor, providing added privacy and a more open feel from the lanai. Grilling is allowed in the backyard area, giving you the ability to enjoy outdoor cooking and entertaining. The home has been meticulously kept and shows true pride of ownership. It also includes a private 1 car garage for secure parking and additional storage. Upon entering, you immediately notice the ultra-modern feel and the exceptionally well-maintained condition of the property. The spacious kitchen features an extra-large island that is so generously sized it feels like it has its own zip code, along with an under-mount sink, quartz countertops, stainless steel appliances, and a walk-in pantry. The main living area has tile flooring throughout, creating a clean and seamless look, and opens to a screened-in lanai with brick pavers for easy indoor and outdoor living. Upstairs, the upgraded Berber-carpeted staircase with elegant railing leads to a loft area and all bedrooms. The primary suite is generously sized and includes multiple walk-in closets and a beautifully designed en-suite bathroom. Bedrooms two and three each feature carpeting and their own walk-in closets, offering excellent storage and flexibility. The home also includes hurricane shutters stored in the garage, providing added storm protection and peace of mind. Bayside Terrace offers resort-style amenities including a waterfront infinity heated salt-water pool, a covered pavilion overlooking the water, a cabana, two BBQ grills, a gas fire pit, a fitness center, clubhouse, and a dock with kayak and canoe launch access. The gated entrance and deed restrictions add an extra layer of privacy and security, while the waterfront setting allows residents to enjoy Florida sunsets and an active coastal lifestyle. Please view two videos: Tour 1 & Tour 2.

1505 Sunset Wind Loop, Oldsmar

50 Willowood Lane, Oldsmar
$1,499,900
6 Beds ⋅ 5 Baths ⋅ Deerpath Unit One SubDv. ⋅ 34677 Zip Code
Tucked away on a quiet cul-de-sac inside the gated East Lake Woodlands community, this 4,475-square-foot home offers something that's becoming increasingly difficult to find in Tampa Bay: **property and privacy.** Situated on 1.4 wooded acres with no rear neighbors, you'll enjoy peaceful conservation views from nearly every room, along with a 2,000-square-foot screened pool and outdoor entertaining area designed for everything from quiet mornings with coffee to weekend gatherings with family and friends. Yet you're never far from the conveniences of everyday life. Boot Ranch shopping, including Publix, Target, and Walmart Neighborhood Market, is just 7 minutes away. East Lake Middle and High School are within 12 minutes, and restaurants, shopping, and entertainment are all close by. Inside, the home offers an incredibly flexible floor plan with room for just about every lifestyle. The main level features the primary suite, a dedicated office (or fifth bedroom), formal dining room, second bedroom with a full bath, spacious laundry room, family room, game room, and a private in-law suite with its own entrance—ideal for multigenerational living, long-term guests, or a home business. Recently painted throughout, the main living areas showcase beautiful Turkish herringbone tile flooring, soaring ceilings reaching nearly 25 feet, and abundant natural light with tranquil views of the conservation beyond. At the center of the home is a kitchen designed for gathering. Granite countertops, stainless steel appliances, custom cabinetry, a prep sink and island, breakfast bar, pantry, and built-in desk provide exceptional functionality, while the oversized breakfast area comfortably accommodates an eight-person table. The kitchen flows seamlessly into the family room, where a wood-burning fireplace and wet bar create the perfect setting for entertaining. Upstairs, you'll find two generously sized bedrooms connected by a Jack-and-Jill bath, along with an oversized loft overlooking the family room below. Whether you envision a media room, game room, home gym, or second family room, the possibilities are endless. Additional walk-in storage provides plenty of space to stay organized. Residents enjoy the security of East Lake Woodlands' 24-hour manned gate, along with the added privacy of the gated Deerpath enclave. Optional membership to East Lake Woodlands Country Club offers golf, tennis, fitness, dining, and social amenities just minutes from your front door. Homes offering this much space, privacy, flexibility, and location rarely become available. Schedule your private tour and experience it for yourself.

50 Willowood Lane, Oldsmar

83 Pelican Drive N, Oldsmar
$195,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Discover exceptional value in Gull-Aire Village, a vibrant 55+ community, with this meticulously maintained home ready for its next owner. Move right in! this sale includes all furnishings and contents, including a 60-inch TV, for a seamless transition. Enjoy peace of mind with a host of recent upgrades: In March of 2024 a brand-new shingle roof, 11 new hurricane windows, and 11 new solar panels for energy efficiency were installed. Additional improvements include a new carport roof in 2025, a hot water heater installed in February 2026, updated flooring in the back bedroom (July 2025), and a modern A/C unit (September 2020). A vapor barrier was replaced in 2010.Convenience abounds with inside laundry and a relaxing screened porch. There is a utility room for storage or bikes. Gull Aire Village offers outstanding amenities, including a lively clubhouse, library, pool table, shuffleboard courts, bocce ball court, and a large, heated pool and spa. Residents enjoy a rich calendar of planned activities and the freedom of a golf cart-friendly neighborhood. The affordable HOA fee is just $70 per month. Pet lovers are welcome. One pet of any size is permitted, and a second pet is allowed with an Emotional Support letter from your primary physician. Best of all, you own the land. This ideal location places you across the street from popular destinations like AMC Theatres, Beall's, Marshall's, Pet Smart, Dollar Store, Ulta Beauty, and an array of dining options including Craft Street Kitchen, Country Pizza Italian Grill, Shaker and Peel, Chipotle, Mandolas, and Eve's Family Restaurant. Essential services such as Super Walmart, Publix, and Countryside Hospital are just a 15-minute drive away, while the stunning beaches of Honeymoon Island and Caladesi State Parks are approximately ten miles from your doorstep. All room measurements are approximate and should be verified by the buyer. Do not wait!

83 Pelican Drive N, Oldsmar

140 Brent Circle, Oldsmar
$499,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
Short Sale. Seller Motivated! Asking price is under last appraisal value. Assumable mortgage for qualified buyers. 6.25 interest rate. Come take a look at this beautiful 3 bedroom, 3 bath bay front townhome overlooking Old Tampa Bay and Safety Harbor. Seaside Estates is a gated community, located in the heart of Oldsmar, which offers may options for access to the water, as well as major thoroughfares. 3 Car tandem garage that walks out to a beautiful view, the common area and boat docks. Stainless Steel appliances, wood flooring, renovated spare bathrooms, and spacious balconies from the great room, and the primary bedroom as well. A wood burning fireplace is also located in the primary bedroom for those cozy nights overlooking the water. The spacious floor plan beautiful water views. Seaside estates is a golf cart-friendly community, offering amenities such tennis and pickleball courts, a swimming pool and Jacuzzi. There is a dock area that offers fishing opportunities and houses the particular residents that own boat docks. Located on a few minutes away from waterfront public parks, recreational facilities, and restaurants. 20 events annually are hosted by the community annually, with monthly dinners strategically planned around the scenic Tampa Bay. This neighborhood is just minutes from downtown Oldsmar and Safety Harbor which have a variety of restaurants, nightlife, street and music festivals, walking and biking trails, kayaking, Seaside estates is also pet friendly. 20 min to Caladesi State Park and the pristine Honeymoon Island and 20 minutes to Tampa Airport and 30 minutes to downtown Clearwater. Come take a look at this waterfront gem. Some of these photos have been virtually staged.

140 Brent Circle, Oldsmar

403 Blue Marlin Drive, Oldsmar
$167,900
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Welcome to your new home in the highly sought-after 55+ Gull-Aire Village! Perfectly situated on a spacious corner lot, this charming Jacobsen manufactured residence offers both comfort and convenience within walking distance to the community pool and clubhouse. Constructed in 1993, it features durable ¾ inch plywood subfloors with laminate, carpet, and tile flooring throughout. Enjoy the versatility of the enclosed Florida room, equipped with central air and heat as well as a custom fan system—ideal for hobbies and creative projects. Recent upgrades include a new hot water heater installed in 2018 and beautifully renovated bathrooms completed in 2020. Further improvements include new windows, a front door, siding, and insulation added in 2013.The kitchen is outfitted with sleek 2019 stainless-steel appliances including a refrigerator and dishwasher. A new air conditioning system installed in 2016. A roof-over was added in 2005, and an inside laundry area comes complete with a washer and dryer for your convenience. The vibrant clubhouse is the heart of the community, hosting monthly events and providing amenities such as a pool table, shuffleboard, bocce ball court, and a heated pool and spa. There are also regular activities to keep you engaged and active, including yoga, bingo, cards, and line dancing. The golf cart-friendly streets make getting around a breeze! With HOA fees at just $70 per month, you will enjoy affordable living in a wonderfully maintained neighborhood. This pet-friendly community allows one pet of any size, and a second pet is permitted with a doctor's note for emotional support. Best of all, ownership includes the land—no lot rent! Everyday conveniences are just steps away, with AMC Theatres, Bealls, Marshalls, PetSmart, Five Below, and Dollar Store across the street, as well as popular dining options like Shaker & Peel, Craft Street Kitchen, Mandola's, Country Pizza Italian Grill, and Eve's Family Restaurant. Major retailers such as Super Walmart and Publix, along with Countryside Hospital, are only minutes from your door. For outdoor enthusiasts, the stunning beaches of Honeymoon Island and Caladesi State Park are just ten miles away, and a scenic biking and walking trail along the canal offers easy access from within the community. Room sizes are approximate. Do not miss your chance to enjoy the best of Oldsmar living in one of the area's most desirable communities!

403 Blue Marlin Drive, Oldsmar

347 Canal Way, Oldsmar
$198,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Welcome to Gull-Aire Village, a 55+ PET-Friendly and Golf Cart Friendly community in the Heart of Oldsmar! Gull-Aire Village is a Land-Owned community, meaning YOU OWN THE LAND! not just the home. A Very unique property with No rear neighbors. This home comes FULLY FURNISHED! and Features A NEWER ROOF (only 3yrs Old) Newer WINDOWS and Doors, New Flooring(2025) and Vapor Barrier (2025) New Water Heater(2025) Newer AC(2022) Newer Samsung Washer and Dryer(2024) This 2-bedroom, 2-bath home is situated on a serene canal view lot and offers the perfect blend of comfort, convenience, and Florida charm. Inside, you'll find a bright and spacious living area, a functional kitchen with plenty of cabinet space, and a screened Florida room where you can relax and enjoy peaceful water views. Split bedroom plan, the primary bedroom features an En-Suite bath, and one additional bedroom for guests, hobbies, or a home office. Beautifully landscaped. Air conditioned Florida room that is not included in the square footage 14 x15. Additional glass enclosed porch on rear of home 10 x14. Good sized utility too. With a Low-cost monthly HOA fee of Only $60 a month, it’s an affordable option for those seeking an active lifestyle. Community amenities include a Heated Pool, Spa, Active Clubhouse with a Library and Pool Table, Shuffleboard courts, Bocce ball court and a calendar of Social Events. Just cross the street and there are wonderful Restaurants, Shopping, and a movie theater! You can walk to AMC theatres, Beall’s, Marshall’s, Dollar Store and Restaurants. Just minutes to Westfield Mall, Target, a Super Walmart, Publix and Countryside Hospital. A walking/running/biking trail is located adjacent to Canal Way, which takes you directly to picturesque Sheffield Park, which is a lovely place with trails to walk, play disc golf, PICKLEBALL, or go to the Dog Park. There is also a playground for the grandkids. You can walk along the path of the Tarpon outfall canal, on the west edge of Gull-Aire Village, and enjoy all the Florida wildlife, including the occasional Manatee sighting. Very Close to Dunedin and Safety Harbor! Less than 30mins to Tampa International Airport. Only 20 minutes to Honeymoon Island Beach and Caladesi State Parks. Come Enjoy the Florida Life-Style with this Low Maintenance home!!

347 Canal Way, Oldsmar

106 Lakeside Court, Oldsmar
$145,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Price Lowered! Such a Great Value! This Condo is located within the Gated community of East Lake Woodlands. This unit is on the second floor and features an eat in kitchen, living/dining room with sliders out to the screened lanai, split bedroom plan, the primary suite has a walk-in closet, a secondary closet and a linen closet. The primary bath has a step in shower. The guest suite has a bath off the hallway. The laundry closet is located on the lanai & includes a washer/dryer. Covered parking 1 space under carport. Unit is located across from the Pool! This unit needs your attention & priced to offset reno to make it your own. Great rental, primary residence or winter getaway..No waiting period for a buyer to rent the condo. Excellent opportunity!

106 Lakeside Court, Oldsmar

How much is your home worth?

Get instant property value now!