Oldsmar Real Estate

Oldsmar Real Estate

Welcome to Oldsmar, Florida, a hidden gem nestled in the heart of Pinellas County. This charming city, located just a stone's throw from the sparkling Gulf of Mexico, offers a unique blend of small-town charm and modern amenities, making it an ideal choice for families, retirees, and everyone in between.

Oldsmar is renowned for its vibrant community spirit and rich history, dating back to its founding in 1916. The city is named after the Oldsmobile brand, a nod to its automotive heritage, and today, it boasts a picturesque downtown area filled with delightful shops, restaurants, and parks. Residents and visitors alike can enjoy the scenic views along the waterfront of Old Tampa Bay, where recreational opportunities abound, from fishing and boating to leisurely strolls along the waterfront trails.

The city's commitment to preserving green spaces is evident in its numerous parks, including the expansive R.E. Olds Park, which features picnic areas, playgrounds, and beautiful nature trails. Oldsmar is also home to the popular Oldsmar Flea Market, a bustling hub where you can find everything from antiques to fresh produce.

With its convenient location, Oldsmar offers easy access to major highways, making it a breeze to explore nearby attractions such as the beautiful beaches of Clearwater and St. Pete, as well as the vibrant cultural scene in Tampa. Whether you're looking for a serene place to call home or a lively community to explore, Oldsmar welcomes you with open arms and an abundance of opportunities. Come discover why so many are proud to call this charming city their home!

Newest Listings in Oldsmar

$370,000
3 Beds ⋅ 2 Baths ⋅ Sheffield Village Ph Ii At Bayside Meadows SubDv. ⋅ 34677 Zip Code
--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
$250,000
2 Beds ⋅ 2 Baths ⋅ St Andrews Condo SubDv. ⋅ 34677 Zip Code
Discover this beautifully remodeled GROUND-FLOOR END UNIT in the highly sought-after Saint Andrews community of East Lake Woodlands. INCLUDED IN RENT is water, sewer, trash, cable, pool, & internet. Located just steps from the community pool, one of the largest in the area, this condo offers resort-style living. East Lake Woodlands is home to top-rated schools and an optional Ardea Country Club membership, providing access to two championship golf courses, 12 tennis courts, a pickleball complex, a fitness center, and an on-site restaurant. Overlooking the 18th hole of the North Course, this move-in ready condo offers breathtaking golf course views and a beautifully updated interior. Recent upgrades include new shaker kitchen cabinets, granite countertops, luxury vinyl plank flooring in both bedrooms, fresh interior paint, and stylish light fixtures. The spacious kitchen features ample storage and a cozy breakfast nook, while the open living and dining area is filled with natural light from oversized sliding glass doors leading to a screened porch overlooking the course. The split-bedroom floor plan provides privacy, and the primary suite includes a walk-in closet, double vanity, soaking tub, and private porch access. Relax on the screened lanai and enjoy peaceful golf course views, beautiful sunsets, and Florida's natural beauty. With modern updates, an ideal layout, and an unbeatable location, this condo offers the perfect blend of comfort and convenience

121 Lindsay Lane Unit 31, Oldsmar
$229,500
2 Beds ⋅ 3 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
Welcome to this 2-bedroom, 2.5-bath townhome located in the desirable gated community of Countryside Key in the heart of Oldsmar. This spacious floor plan features two primary suites upstairs, each with its own private bathroom, while the convenient half bath downstairs is perfect for guests. Enjoy an open living and dining area with plenty of natural light and a private screened patio ideal for relaxing or entertaining. The seller is offering a concession toward new flooring and/or appliances, providing a great opportunity to personalize the home to your own style. Residents of Countryside Key enjoy access to a community pool, tennis courts, and beautifully maintained grounds, all just minutes from shopping, dining, parks, top-rated schools, Tampa International Airport, and the beaches.

366 Countryside Key Boulevard, Oldsmar
$149,900
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
Maintenance free condo living within the prestigious gates of East Lake Woodlands! Pride of ownership abounds in this well maintained first floor unit offering just under 1,100 sq ft of fine Florida living with 2 bedrooms, 2 bathrooms and a convenient covered carport. Open concept floor plan with a great room that combines living and dining spaces ideal for family gatherings and entertaining. Living and entertaining space is extended outside with sliding glass doors leading to a lanai looking out on the community’s well-manicured green spaces. A serene setting for morning coffee or afternoon cocktails. The lanai also houses a convenient storage closet. The spacious kitchen includes an eat-in area and features tile flooring. The appliances include a ceran top range, built-in microwave, refrigerator (5 yrs old) and dishwasher. Privacy prevails with an ideal split bedroom layout. The primary bedroom is located just off the living room and offers generous storage boasting 2 walk-in closets and an additional wall closet and the room offers a sliding glass door to the lanai. The ensuite features a single vanity with dressing area and a walk-in shower. The secondary bedroom is located on the opposite side of the home and features laminate flooring, a wall closet & ceiling fan. The hall bathroom is designed with a single vanity and a tub/shower combination. The hallway laundry closet is perfectly situated for ideal convenience, and the seller is generously including the washer and dryer. Additional features include AC 2022, WH 2022. The HOA includes exterior and grounds maintenance, community pool, water, sewer, trash, cable, internet. This condo is just steps away from the community pool! The home is zoned for exceptional schools and near to all, restaurants, shopping, medical and of course the famed Gulf beaches are nearby. The recently renovated Ardea Country Club lies within the gates of East Lake Woodlands. The club offers several levels of membership and has an impressive array of amenities including 2 championship golf courses, 2 resort style heated pools, 12 pickleball courts, 14 clay tennis courts, state-of-the-art fitness center, restaurant and bar. Magnificent home in a convenient location… carefree Florida living!

129 Nancy Drive, Oldsmar
$188,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Woodlake Run SubDv. ⋅ 34677 Zip Code
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, Oldsmar
$530,000
3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code
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
$355,000
3 Beds ⋅ 3 Baths ⋅ Tuscany Woods Preserve SubDv. ⋅ 34677 Zip Code
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
$1,149,900
4 Beds ⋅ 3 Baths ⋅ Greenhaven Unit Two SubDv. ⋅ 34677 Zip Code
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
$450,000
3 Beds ⋅ 2 Baths ⋅ Oldsmar Country Club Estates Sec 3 SubDv. ⋅ 34677 Zip Code
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
$247,000
2 Beds ⋅ 2 Baths ⋅ Gull-Aire Village SubDv. ⋅ 34677 Zip Code
Experience the charm of Gull-Aire Village 55+ in this beautifully renovated home, ready for its next owners. Boasting a spacious 1,320 square feet with stylish laminate flooring throughout, this residence is perfect for entertaining and comfortable living. The split-bedroom layout ensures privacy for both you and your guests, while both bathrooms feature luxurious walk-in showers for added convenience. The Chefs kitchen is a culinary delight, featuring an inviting island, sleek granite countertops, and an abundance of cabinets for optimal storage. Adjacent to the kitchen, the dining area impresses with built-in cabinetry, ideal for a coffee bar or entertaining bar. Elegant barn doors lead from the dining area into the cozy family room, where the indoor laundry—complete with washer and dryer—offers practicality and ease. Carport offers side-by-side parking. Embrace an active lifestyle at the vibrant clubhouse, the heart of the community, events and offering amenities such as a pool table, shuffleboard, bocce ball court, and a heated pool and spa. Stay engaged with regular activities. Golf cart-friendly streets make navigating the neighborhood effortless! Enjoy affordable living with HOA fees at only $70 per month. Bring one pet of any size, and a second pet is allowed with a doctor's note for emotional support. Best of all, you own the land. Conveniences are at your fingertips, like AMC Theatres, Bealls, Marshalls, PetSmart, Five Below, and Dollar Store just across the street. Savor local flavors at Shaker & Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eve's Family Restaurant. Essential retailers such as Super Walmart and Publix, along with Countryside Hospital, are only minutes away. Outdoor enthusiasts will love the proximity to the stunning beaches of Honeymoon Island and Caladesi State Park, just ten miles away. A scenic biking and walking trail along the canal are easily accessible from within the community. Room sizes are approximate. Do not miss your chance to experience the best of Oldsmar living in one of the area’s most sought-after communities.

407 Dolphin Drive S, Oldsmar
$216,000
2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code
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
$665,000
3 Beds ⋅ 2 Baths ⋅ Parcel B - The Pinnacle SubDv. ⋅ 34677 Zip Code
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
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