Single Family Homes for Sale in Oldsmar, FL

3 Beds ⋅ 2 Baths ⋅ Manors Of Forest Lakes The Ph 2 SubDv.

Welcome to this beautifully updated three-bedroom home in Forest Lakes, offering comfortable living spaces and thoughtful improvements throughout. The updated kitchen, completed in 2025, provides a fresh and inviting space that leads to the home’s spacious living and dining areas, ideal for everyday living and entertaining. The primary bedroom has also been updated, creating a comfortable retreat for the new owner. Go outside to enjoy a large, fully fenced yard and screened patio area, offering plenty of space for outdoor dining, relaxing, pets or play. The garage previously converted gives additional interior flex living space. The area has added central air and heat, which adds to the square footage of the home. Major updates provide peace of mind, including a new roof in 2025, fresh exterior paint in 2025 and hurricane windows. With the key improvements completed, this home is move-in ready and offers the opportunity for a new owner to settle in with minimal additional updates, ready to welcome its next living adventure. It has access to recreational park, close to beaches, shopping and zoned for desirable schools including Eastlake High School.

819 Jacaranda Drive, Oldsmar

$269,000

2 Beds ⋅ 1 Baths ⋅ Oldsmar Rev Map SubDv.

Welcome home to this beautifully renovated 2-bedroom, 1-bath property in desirable Oldsmar, Florida! This move-in-ready home has been completely updated from top to bottom. The kitchen features updated cabinetry, countertops, and finishes, creating a stylish and functional space for everyday living. The bathroom has also been redone with fresh, modern touches. Throughout the home, you'll find all-new flooring that gives the interior a clean, cohesive feel. Major updates include a brand-new metal roof and new AC system, providing important upgrades for comfort and long-term value. With its fresh renovations and convenient Oldsmar location, this home is an excellent opportunity for a first-time buyer, downsizer, or investor.

200 Fairfield Street, Oldsmar

$344,900

3 Beds ⋅ 1 Baths ⋅ Harbor Palms-Unit One SubDv.

A beautifully maintained home in the desirable Sheffield Village area of Oldsmar, this property offers comfort, convenience, and the welcoming charm the community is known for. Located on a quiet cul-de-sac, 415 Maplewood Cir features a bright, open layout with spacious living areas perfect for everyday living and entertaining. The home’s interior is filled with natural light, highlighted by well-kept finishes and a functional floor plan. Complete with granite countertops, the kitchen anchors the living space, offering plenty of storage and easy access to the dining and family areas. Generously sized bedrooms provide privacy and flexibility for guests, family, or a home office. Step outside to enjoy a peaceful backyard with room to relax, garden, or create your ideal outdoor space. Mature landscaping and the neighborhood’s tree-lined streets add to the home’s inviting appeal. Residents of this Oldsmar location enjoy quick access to parks, top-rated schools, shopping, dining, and major commuter routes, making it easy to reach Tampa, Clearwater, and the Gulf beaches. With its combination of location, comfort, and community charm, this Maplewood Circle home is an excellent opportunity in one of Oldsmar’s most established neighborhoods. This home was high and dry during recent storms. Come check this one out today.

415 Maplewood Circle, Oldsmar

$830,700

4 Beds ⋅ 3 Baths ⋅ Cross Pointe SubDv.

Virtually Staged. Welcome to an exceptional 2,736-square-foot luxury home nestled within Cross Pointe, a gated community inside the prestigious guard gated golf community of East Lake Woodlands . Offering 4 bedrooms, 3 baths, a spacious 2-car garage,with workbench area. and bonus space. This beautifully appointed residence blends elegant finishes, thoughtful design, and exceptional outdoor living. Pool access & views from almost every room. Desirable split-bedroom floor plan features soaring ceilings and travertine flooring complemented by engineered hardwood & tile floors. The updated gourmet kitchen is designed for both everyday living and entertaining, featuring Bosch and Frigidaire appliances, (Range has induction cooktop & convection/air fry oven) quartz tops, crisp white cabinetry, and a striking navy island. Breakfast area overlooking pool. The family room offers a warm wood-burning fireplace (updated 2020) and a sophisticated navy wine bar, creating an inviting gathering space. Spacious primary suite includes a comfortable sitting area and sliders that open directly to the screened porch, offering beautiful views of the private pool and backyard . Walk-in closet with organizers. Primary bath has soaking tub, large marble shower, private water closet & dual sink vanities. 3 guest bedrooms, with one having an ensuite bath also providing convenient access to the pool area—perfect for effortless poolside living. Bonus/Flex room with its own A/C (2026) is perfect for an office, hobby room, studio, gym, etc. Outdoor living is truly exceptional. The screened rear porch features paver flooring and overlooks the Saltwater PebbleTec pool , complete with Caribbean blue tile, a charming, soothing waterfall and gazebo. Pool pump & new salt system (2025). An expanded paver patio (2025) extends into the private backyard, providing ample space for entertaining, relaxing, and enjoying the peaceful surroundings. Many updates include tile roof (2019), HVAC (2017), Water Heater (9/2026), Paver patio (2022), Kitchen updated (2020) with professional kitchen cabinet refinishing (2026), Bosch refrigerator (2025), Frigidaire appliances (2026). All ceiling fans updated (2024 & 2025). Newly textured ceilings (2022), modern lighting. With its luxurious finishes, spacious layout, updated kitchen, resort-style pool, and prime location within two prestigious gated communities, this home offers an exceptional Florida lifestyle with privacy, comfort, and elegance at every turn. Centrally located to Tampa International and St . Pete/Clearwater Airport, award winning beaches, boating and fishing, professional sporting events, historic Dunedin and Safety Harbor, Pinellas and Duke Energy Bike Trails, restaurants, shopping, and hospitals. East Lake Woodlands is a golf community with an optional membership available to the nationally renowned ELW Country Club, featuring outstanding amenities including two championship golf courses, sixteen tennis courts, pickleball, fully-equipped fitness center, lap & freeform pools, splash pad, dining, full social calendar/club, and is also part of ClubCorp/Invited with reciprocal rights to 300+ clubs. Low HOA and NO flood insurance required. A fantastic value! Call today for your private tour!

1723 Captiva Drive, Oldsmar

$489,000

4 Beds ⋅ 2 Baths ⋅ Oldsmar Rev Map SubDv.

Pristine Updated 4-Bedroom home in the Heart of Oldsmar. Discover exceptional value in this 4-bedroom, 2-bath home, thoughtfully updated with quality finishes and modern features throughout. Located in downtown Oldsmar, this move-in-ready home combines stylish updates, comfortable living spaces, and an outstanding location in downtown Oldsmar. From the moment you arrive, the inviting front porch and beautifully refreshed landscaping create a warm first impression. The exterior features durable HARDIE BOARD SIDING accented by fixed-mount shutters, while NEW sod and landscaping enhance the front yard. Inside, you'll find an impressive list of recent updates, including NEW solid wood kitchen cabinets, NEW stainless steel appliances, NEW fixtures, NEW luxury laminate flooring, NEW lighted ceiling fans, and lighting throughout. The kitchen is finished with stunning NEW quartz countertops that overlook the dining and living areas, creating an open and inviting space for everyday living and entertaining. A convenient coffee bar adds both style and function to the dining area. The AC and condenser were totally overhauled (2020) and updated. Vaulted and tray ceilings enhance the spacious feel of the home. The flexible front bedroom offers an ideal space for a HOME OFFICE or sitting room. Bedroom 3 enjoys PRIVACY IN ITS' OWN HALLWAY and features an adjoining bathroom and walk-in closet. Bedroom 4 is generously sized, bright, and airy. The SPACIOUS PRIMARY SUITE provides abundant natural light and a vaulted ceiling. The primary bathroom includes a roomy linen closet and walk-in closet, offering excellent storage and convenience. The garage features extra-high ceilings, providing valuable POTENTIAL FOR OVERHEAD STORAGE and maximizing usable space. Beyond the home, enjoy everything that makes Oldsmar such a DESIRABLE PLACE TO LIVE. You'll be minutes from beautiful parks, playgrounds, biking and walking trails, schools, restaurants, historical museum, ZIP-line adventures, and more. Downtown Oldsmar offers a unique golf-cart-friendly community atmosphere along with an impressive array of recreation and entertainment. Residents enjoy access to a world-class BMX racing facility, approximately 10 miles of bike paths, movie theater, ice skating rink, fishing pier, eleven beautiful parks, waterfront event areas and stages, a boat ramp, athletic facilities, numerous restaurants, and highly regarded schools, including Oldsmar Elementary's K–8 campus. With almost half of Oldsmar's land area dedicated to green space and parks, this home offers more than beautiful updates—it offers an exceptional lifestyle. Quality updates, thoughtful design, abundant storage, and a convenient Oldsmar location make this a home that delivers outstanding value

508 Washington Avenue, Oldsmar

$310,000

3 Beds ⋅ 1 Baths ⋅ Shoreview Ph 2 SubDv.

CHARMING 3 bed, 1 bath impeccable home in downtown Oldsmar area. NEW interior doors, NEW stove, NEW baseboards, NEW bathroom vanity, lighting, mirror,, NEW remote control ceiling fans with lights, NEW carriage lights (front and back) NEW GFCI outlets, NEW paint interior, exterior, NEW paint garage, patio, NEWER windows and slider with integral blinds (2023, 2026), HWH 2025, DISHWASHER 2023, MICROWAVE 2022, ROOF 2022. Use your imagination with the oversized patio for a total outside living experience; large fenced yard. This home is located a short distance from Mobbly Bayou waterfront park, RE Olds park with fishing pier, event and picnic areas, playgrounds, volleyball, and Bicentennial Park with tennis and pickleboard courts, shaded walking paths, and home to Adventure Zip Line Tours. Shopping, restaurants, theater, athletic facilities, museum, school and library all only minutes away. WORLD CLASS BEACHES and TAMPA INTERNATIONAL AIRPORT are both nearby. Zoned for Oldsmar Elementary School (A rated) and NOW a K through 8 school. This home is HIGH AND DRY! Motivated Seller!

650 Timber Bay Circle W, Oldsmar

$259,900

2 Beds ⋅ 2 Baths ⋅ Harbor Palms-Unit Five SubDv.

Investor special with exceptional upside! This concrete block 2-bedroom, 2-bath, 2-car garage home is priced to sell and offers outstanding renovation potential. Situated on a nicely sized lot with beautiful lake views and no rear neighbors, the fully fenced backyard has plenty of room for a pool. The home has an updated electrical panel. The HVAC system was updated in 2019. The roof was last replaced in 2009. The office provides approximately 270 additional square feet beyond the heated living area, offering flexible space for a home office, hobby room, or future expansion. (The second bathroom is located in the garage.) Enjoy a great central location just a short walk to Sheffield Park and Harbor Palms Nature Park, featuring walking trails, a boardwalk, fishing pier, and kayak launch. No HOA and convenient access to Tampa, St. Petersburg, Gulf beaches, shopping, dining, and Tampa International Airport. Cash offers only. Property is being sold As Is with no repairs.

704 Lemonwood Drive, Oldsmar

$299,900

5 Beds ⋅ 4 Baths ⋅ Oldsmar Revised Map SubDv.

Exceptional builder or investor opportunity in a prime Oldsmar location! Situated on an oversized 11,347 sq. ft. lot directly across from scenic R.E. Olds Park, this property offers partial water views of Tampa Bay, park views, and outstanding redevelopment or renovation potential. The existing structure includes a 3-bedroom, 2-bath upper level plus two 1-bedroom, 1-bath lower-level units, offering multiple possibilities for redevelopment or renovation (buyer to verify permitted use). Additional features include a 2-car carport and a concrete block storage building. Enjoy a golf cart-friendly community with walking trails, fishing pier, playgrounds, picnic shelters, and year-round events just across the street. Cash offers only. Property is being sold As Is with no repairs. Conveniently located with easy access to Tampa, St. Petersburg, Tampa International Airport, and Gulf beaches.

613 Chestnut Street, Oldsmar

$299,900

3 Beds ⋅ 2 Baths ⋅ Oldsmar Revised Map SubDv.

Investor special with exceptional upside! This 3-bedroom, 2-bath, 1-car garage home sits on a spacious quarter-acre corner lot directly across from scenic R.E. Olds Park, offering water views, walking trails, playgrounds, a fishing pier, picnic shelters, volleyball courts, seasonal events, and a dog park. The home features a split-bedroom floor plan with a primary suite that includes a walk-in closet, en-suite bath with a step-in shower, and sliding glass doors leading to a patio. The guest bath offers a tub/shower combination. The roof was replaced in 2016. Double-pane sliding glass doors open to two patios overlooking the park. No HOA or deed restrictions—bring your boat, RV, or golf cart! Great central location with convenient access to Tampa and St. Petersburg.

204 Shore Drive W, Oldsmar

$365,000

3 Beds ⋅ 2 Baths ⋅ Sheffield Village Ph Ii At Bayside Meadows SubDv.

--SERIOUS SELLER-WILLING TO NEGOTIATE-- Check out this BEAUTIFUL 3-bedroom, 2-bath BLOCK home WITH GARAGE. located on a quiet cul-de-sac in the heart of Oldsmar. BEAUTIFUL HIGH GLOSS TILE FLOORING THROUGHOUT Featuring spacious living areas with vaulted ceilings, a primary bedroom with an ensuite, and a split bedroom layout for added privacy and a rear screened porch perfect for relaxing or entertaining. The home has been thoughtfully upgraded with a new electrical panel (2018), roof (2020), air conditioning system (2021), gutters (2022), garage door (2022), water heater (2022), and water softener tank (2024) Exterior Water Line (2025). along with fresh exterior paint. Situated just steps from Sheffield Park, residents enjoy access to hiking and running trails, tennis and basketball courts, a playground, and a covered pavilion for events. Conveniently close to shopping centers, restaurants, downtown Tampa, the international airport, Clearwater beaches, and St. Pete, this neighborhood offers a peaceful environment with NO HOA fees. This turnkey home combines modern comfort with an unbeatable location—great curb appeal, stop by and take a look you wont be disappointed! MOTIVATED SELLER! SUBMIT YOUR OFFER TODAY!

1909 Castle Bay Court, Oldsmar

$445,000

3 Beds ⋅ 2 Baths ⋅ Oldsmar Country Club Estates Sec 3 SubDv.

Florida living at it's best. This fully renovated beautiful solid block home is located in the very desirable Oldsmar Country Club Estates neighborhood and is across the street from the bay and just down the street from three waterfront parks, Veterans Memorial Park, R.E. Olds Park and from Mobbly Bayou Beach Park. This charming house boasts a split bedroom open floor plan. It has a giant sun room/all day room connected to the back of the house with plenty of windows surrounding it. The owner just had the main front door and the rear door replaced with new high impact doors. The owner is selling personal items to get ready for the sale of the home and they show as clutter in the pictures, so I might be posting new pictures soon. These pictures don't do this wonderful home justice. Wait till you see this huge kitchen with it's quartz countertops, stainless steel appliances and very spacious wood cabinets. There are fruit trees in the back yard which include mango trees and sweet sop trees. The garage is air conditioned and heated. This home is conveniently located only 15-20 minutes from Tampa International Airport and only minutes to downtown Tampa and to some of the best beaches in the US, great restaurants, shopping, theaters and hotels. There are also tennis courts, a zip line, hiking trails, kayaking and paddle boarding, the neighborhood boat ramp, an organic garden, the public library and lots of shops all walking distance from the house.

331 Shore Drive E, Oldsmar

$439,000

3 Beds ⋅ 2 Baths ⋅ Tampashores Hotel Plaza Sec SubDv.

Welcome to the TAMPA BAY LIFESTYLE WITHOUT THE WATERFRONT PRICE TAG. This beautifully fully remodeled 3-bedroom, 2-bath home offers the rare combination of modern updates, an incredible location, and exceptional flexibility for homeowners and investors alike. Completely renovated from top to bottom, this move-in-ready home features an open-concept floor plan with luxury vinyl plank flooring throughout, quartz countertops, updated cabinetry, stainless steel appliances, designer fixtures, and beautifully renovated bathrooms. Natural light fills the spacious living areas, creating a bright and inviting atmosphere perfect for everyday living and entertaining. Location is everything, and this one is hard to beat. Situated next to one of Oldsmar’s beautiful waterfront parks and just steps from the fishing pier, playground, walking trails, and scenic Tampa Bay shoreline, this home offers a lifestyle that is difficult to replicate at this price point. Enjoy easy access to dining, shopping, marinas, downtown Safety Harbor, Dunedin, Clearwater, and some of the area’s most popular beaches. Nearby attractions including Tampa Bay Downs, waterfront festivals, and outdoor recreation make this an exceptional place to live, vacation, or invest. Whether you’re looking for a primary residence, first-time home, second home, seasonal retreat, or income-producing investment property, this home offers exceptional flexibility to fit your goals. Currently operating as a successful SHORT-TERM RENTAL/AIRBNB (furniture negotiable). The property provides immediate income-producing potential and an opportunity for investors to capitalize on Oldsmar’s growing demand for vacation and extended-stay accommodations. Recent short-term rental performance included approximately $3,000 in gross rental revenue during a recent five-night stay. Additional highlights include a 2024 roof, no HOA, and convenient access to Tampa, Clearwater, St. Petersburg, Tampa International Airport, shopping, dining, and some of the area’s most popular beaches. Experience the charm of Oldsmar and enjoy the perfect blend of comfort, convenience, and coastal lifestyle. Schedule your private showing today.

102 Shore Drive E, Oldsmar

Single Family Homes for Sale in Oldsmar, FL

All Single Family Homes for Sale in Oldsmar, FL

Joseph Sullivan Real Estate

Search

Resources

About