Oldsmar Real Estate

Oldsmar Real Estate

Welcome to Oldsmar, Florida—a hidden gem nestled in the heart of Pinellas County. This charming city, with its rich history and vibrant community spirit, offers a unique blend of suburban tranquility and urban convenience. Founded in 1916, Oldsmar has retained its small-town charm while evolving into a modern hub of activity, making it an ideal place for families, retirees, and young professionals alike.

Oldsmar boasts an enviable location, situated just a short drive from the stunning Gulf Coast beaches and the bustling cities of Tampa and St. Petersburg. Residents enjoy easy access to a variety of recreational activities, including water sports, hiking trails, and picturesque parks. The city is home to the beautiful Oldsmar Park, featuring playgrounds, picnic areas, and scenic walking paths that invite residents to embrace the great outdoors.

The community is known for its friendly atmosphere, with numerous local events and festivals that bring neighbors together throughout the year. Whether it’s the annual Oldsmar Days festival celebrating the city’s heritage or the lively farmers market showcasing local produce, there’s always something happening in this welcoming town.

Oldsmar also prides itself on its excellent schools and family-friendly neighborhoods, making it an attractive option for those seeking a nurturing environment for their children. With a variety of housing options, from charming single-family homes to modern condos, Oldsmar caters to diverse lifestyles and preferences.

Discover the allure of Oldsmar, where you can enjoy a relaxed pace of life while being just moments away from the excitement of Florida’s finest attractions. Come explore and find your perfect home in this delightful city!

Newest Listings in Oldsmar

2 Beds ⋅ 2 Baths ⋅ TB8528578 MLS ⋅ East Lake Woodlands Woodlake BLDG.

EXCEPTIONAL GROUND-FLOOR CORNER UNIT WITH RESORT-STYLE LIFESTYLE AT WOODLAKE RUN! Welcome home to this DESIRABLE 2-BEDROOM, 2-BATHROOM condo offering effortless ONE-LEVEL MAINTENANCE-FREE LIVING in the premier gated community of East Lake Woodlands! Boasting 924 SQ FT OF LIGHT-FILLED LIVING SPACE, this prime END-UNIT LOCATION features an OPEN FLOOR PLAN, modern WOOD LAMINATE AND TILE FLOORING throughout (NO CARPET!), and a bright LIVING/DINING ROOM COMBO ideal for entertaining. Enjoy total peace of mind with recent high-value updates including a New electrical panel (2026), 2023 A/C SYSTEM for ultimate energy efficiency, a BRAND-NEW DISHWASHER, and an in-unit washer/dryer set! Unwind on your PRIVATE COVERED PORCH overlooking tranquil green space and scenic pond views. Step right across the walkway to enjoy the REFRESHING COMMUNITY POOL DIRECTLY ACROSS THE BUILDING! Residents of East Lake Woodlands enjoy world-class amenities including 24/7 GUARDED GATE SECURITY, country club options, golf, tennis, and lush walking trails. The ALL-INCLUSIVE MONTHLY HOA conveniently covers water, sewer, trash, exterior building maintenance, cable TV, pest control, and pool upkeep. Ideally located near TOP-RATED SCHOOLS, DINING, SHOPPING, AND TAMPA INTERNATIONAL AIRPORT—this turn-key property is perfect as a PRIMARY RESIDENCE, WINTER RETREAT, OR INVESTMENT OPPORTUNITY! Schedule your private tour today!

10 Woodlake Place Unit 55, Oldsmar

3 Beds ⋅ 3 Baths ⋅ OM728969 MLS ⋅ 158 BLDG.

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

158 Brent Circle, Oldsmar

3 Beds ⋅ 3 Baths ⋅ TB8532311 MLS ⋅ Na BLDG.

Virtually Staged. Beautiful upscale townhome located in the gated community of Tuscany Woods! This gorgeous property offers 3 bedrooms, two full bathrooms and one half bathroom. Formal entry into large foyer leads to a fabulous open floorplan with lots of natural light, space for entertaining and new luxury vinyl flooring throughout the entire home. The kitchen features a breakfast bar, granite countertops, 42" cabinets and newer stainless steel appliances. 10 foot sliding doors lead out to a screened in patio equipped with a projector with screen and outside the screen enclosure is a second paved patio with space to entertain and garden! Upstairs you'll find the spacious master bedroom with en-suite bathroom featuring gorgeous walk in shower, double vanity, and linen closet. Two more large bedrooms along with a full sized bathroom are also located on the second floor. The laundry area with lots of storage space is on the second floor for your convenience! This community is conveniently located close to beaches, parks, Tampa International Airport, restaurants, shopping and more!

1504 Merlot Court, Oldsmar

4 Beds ⋅ 3 Baths ⋅ TB8531583 MLS

Homes like this rarely become available in the highly sought-after gated community of East Lake Woods. Completely remodeled and situated on over a quarter acre overlooking a tranquil pond, this exceptional residence offers the perfect blend of luxury, comfort, and functionality. From the moment you arrive, you'll appreciate the expansive driveway, oversized three car garage, and impressive curb appeal. As you approach the grand double-door entrance, soaring 12 foot ceilings immediately set the tone for what awaits inside. Step through the front doors and your eyes are instantly drawn to the breathtaking views of the sparkling pool and peaceful pond beyond. The home has been freshly painted inside and out and showcases new luxury waterproof vinyl plank flooring throughout, creating a seamless, modern aesthetic. Designed with both everyday living and entertaining in mind, the home features a desirable three way split floor plan, offering privacy for family members and guests alike. The spacious primary suite is a true retreat, complete with high ceilings, plantation shutters, and a spa-inspired ensuite bathroom. Relax in the freestanding soaking tub or unwind in the oversized walk-in shower featuring a rainfall showerhead and body jets. The luxurious bath also includes dual vanities, a dedicated makeup station, and an illuminated LED mirror. As you continue into the heart of the home, you'll discover a stunning open-concept kitchen and family room designed to impress. The fully remodeled kitchen features brand-new solid wood soft-close cabinetry, Taj Mahal quartz countertops, a cooktop with pot filler, new stainless steel appliances, and exceptional workspace for the home chef. Adjacent to the kitchen is a bright breakfast nook overlooking the pool, as well as a separate butler's pantry perfect for a coffee bar, beverage station, or additional storage. Entertaining is effortless thanks to the beautifully redesigned wet bar, featuring rich dark cabinetry, ambient lighting, a sink, and a built-in wine refrigerator. Just beyond, the expansive family room provides ample space for gatherings of any size. A beautifully renovated guest bathroom off the kitchen features designer tile, a modern vanity, and an LED mirror. Toward the rear of the home, you'll find two additional spacious bedrooms and another fully remodeled bathroom with dual sinks, LED mirrors, and convenient access to the pool. Step outside to your own private backyard oasis. The oversized screened lanai surrounds the sparkling pool and offers the perfect setting for year-round Florida living. The outdoor kitchen is equally impressive, showcasing stunning Brown Fantasy granite countertops, a new built-in grill, and a beverage refrigerator. The finishing touch? Your very own private putting green. Whether you're practicing your short game, entertaining guests, or simply enjoying the peaceful pond views, this backyard is designed to be enjoyed. Every detail of this remarkable home has been thoughtfully updated, creating a truly move-in-ready opportunity in one of the area's most desirable gated communities. Additionally residents have the opportunity to join the on-site Ardea Country Club, optional memberships provide access to championship golf, tennis, pickleball, a resort style lap pool, state of the art fitness center and dining. Minutes from top rated schools, Tampa International and St. Pete-Clearwater airports, award-winning Gulf beaches, professional sports team and more!

35 Greenhaven Trail, Oldsmar

3 Beds ⋅ 2 Baths ⋅ TB8531357 MLS

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 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

2 Beds ⋅ 2 Baths ⋅ TB8530978 MLS

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 ⋅ TB8530417 MLS ⋅ Building 1-Green Condos BLDG.

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

222 Caryl Way, Oldsmar

3 Beds ⋅ 2 Baths ⋅ TB8529582 MLS

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

5250 Pinehurst Court, Oldsmar

3 Beds ⋅ 2 Baths ⋅ TB8530374 MLS

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

Oldsmar

3 Beds ⋅ 2 Baths ⋅ O6425984 MLS

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

3 Beds ⋅ 2 Baths ⋅ TB8529421 MLS

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

80 Summerwinds Lane, Oldsmar

4 Beds ⋅ 4 Baths ⋅ TB8529182 MLS

Welcome to this exceptional 4-bedroom, 4-bathroom pool home located on a corner lot within the gated golf community of East Lake Woodlands in Oldsmar. Offering an impressive 3,441 square feet of living space, this beautiful residence combines elegant interiors, flexible living spaces, and a resort-style outdoor setting. Major updates include a 2021 roof, HVAC systems replaced in 2022 and 2023, and a 2022 water heater, providing peace of mind for years to come. A spacious foyer welcomes you into the home, where soaring vaulted ceilings with stunning wood beams and a wood-burning fireplace create a warm and inviting focal point in the living room. Double sliding doors seamlessly connect the indoor living areas to the screened pool and expansive outdoor entertaining spaces, embracing Florida's sought-after indoor-outdoor lifestyle. The thoughtfully designed split floor plan offers privacy and functionality, including a private fourth bedroom with its own en-suite bathroom, perfect for guests or multi-generational living. The spacious bonus room with built-in shelving provides endless possibilities as a home gym, movie theater, studio, game room, or additional living area. The beautifully appointed kitchen is designed for both everyday living and entertaining, featuring quartzite countertops, stainless steel appliances, a double oven, abundant cabinetry, pantry organizers, and a walk-in pantry for exceptional storage. A charming breakfast nook overlooks the pool, while the formal dining room provides an elegant setting for special gatherings. Wood-look tile flooring extends throughout the main living areas, complemented by crown molding throughout the home. The oversized primary suite serves as a luxurious retreat, featuring two large walk-in closets with custom organizers and a spa-inspired en-suite bathroom complete with a soaking tub, walk-in shower, private water closet, and generous vanity space. The updated shared bathroom showcases a modern double-sink vanity with a marble top, an illuminated mirror, and a shower/tub combination. A spacious laundry room with additional cabinetry adds even more convenience. Step outside to your private oasis. The rebuilt pool features all-new equipment and a heater, allowing for year-round enjoyment. The screened lanai offers abundant space for entertaining, including a covered dining area and convenient pool bath with a shower. New tropical landscaping further enhances the home's curb appeal and atmosphere. Residents of East Lake Woodlands enjoy a prime location close to parks, shopping centers, numerous dining options, and highly rated schools. Optional memberships are available at Ardea Country Club, offering access to golf, tennis, fitness facilities, swimming, social events, and more. This remarkable home offers the perfect combination of luxury, space, and lifestyle in one of Oldsmar's most sought-after communities.

475 Holly Hill Road, Oldsmar

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