Oldsmar Homes with 8-12 Months Minimum lease

Welcome to Oldsmar, a charming city located in Pinellas County, Florida. Known for its beautiful landscapes, friendly community, and convenient location, Oldsmar is a fantastic place to call home.

If you're considering living in Oldsmar, you'll be pleased to know that there are plenty of housing options available, including homes with 8-12 months minimum lease agreements. This flexibility is perfect for those who are looking for a temporary living arrangement or want to test out the area before committing to a long-term lease.

Whether you're interested in a cozy apartment, a spacious single-family home, or a townhouse with all the amenities, Oldsmar has something for everyone. From modern properties with updated features to more traditional homes with character, you're sure to find a place that suits your style and budget.

In addition to its housing options, Oldsmar offers a variety of recreational activities, shopping destinations, and dining establishments for residents to enjoy. With easy access to nearby beaches, parks, and cultural attractions, there's always something to see and do in this vibrant city.

Come and discover all that Oldsmar has to offer. From its welcoming community to its diverse real estate options, this city has everything you need to live a comfortable and fulfilling life.

Newest Oldsmar Homes with 8-12 Months Minimum lease

$245,000

2 Beds ⋅ 2 Baths ⋅ Sheffield Village At Bayside Meadows SubDv. ⋅ 34677 Zip Code ⋅ TB8535233 MLS ⋅ Active Status

This spacious and well maintained 2-bedroom, 2-bath end unit Villa offers a comfortable floor plan and easy, worry-free living right in the heart of Oldsmar. With nearly 1,300 square feet and vaulted ceilings, the home features all tile flooring throughout, a large kitchen with plenty of cabinetry and a breakfast bar, plus an open family/dining area. The living room includes a cozy fireplace, creating a warm focal point for the space. Sliders lead to an enclosed porch, perfect for relaxing or enjoying morning coffee. An interior laundry closet adds everyday convenience. Major system upgrades provide excellent long-term value and peace of mind: • New roof (2021) • New HVAC (2024) • New water heater (2024) • New electrical panel (2024) • Impact windows (2016) • Sliding glass door (2018). A rare and highly desirable bonus is the two assigned covered parking spaces steps from your front door—a standout feature in this community and a true benefit for owners. Community amenities include a sparkling pool, and you’re just down the street from Sheffield Park, featuring tennis and basketball courts, a playground, dog park, fishing, disc golf, exercise stations, walking paths, and more. With low HOA fees of $110/month, including lawn maintenance, you’ll have plenty of time to enjoy the pool and Oldsmar’s interconnected parks. You’re also steps from Harbor Palms Nature Park and Preserve and the Oldsmar Trail, an 11-mile trail popular with bicyclists and joggers —perfect for nature walks, wildlife viewing, and beautiful sunsets. Nearby conveniences include athletic fields, shopping, dining, and world class beaches. This Villa is a well-cared for home with major updates already completed, offering comfort, convenience, and the best of Florida living.

2060 Sheffield Court, Oldsmar

$229,500

2 Beds ⋅ 3 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code ⋅ TB8534362 MLS ⋅ Active Status ⋅ N/A BLDG.

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

$1,149,900

4 Beds ⋅ 3 Baths ⋅ Greenhaven Unit Two SubDv. ⋅ 34677 Zip Code ⋅ TB8531583 MLS ⋅ Active Status

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

$665,000

3 Beds ⋅ 2 Baths ⋅ Parcel B - The Pinnacle SubDv. ⋅ 34677 Zip Code ⋅ TB8529582 MLS ⋅ Active Status

RARELY AVAILABLE VILLA OPPORTUNITY IN PRIVATE PINNACLE COMMUNITY OF EAST LAKE WOODLANDS. "THIS IS A MAINTENANCE FREE COMMUNITY." 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

$299,900

2 Beds ⋅ 2 Baths ⋅ St Andrews Condo SubDv. ⋅ 34677 Zip Code ⋅ TB8526165 MLS ⋅ Active Status ⋅ 50-100 BLDG.

Experience resort-style living in this beautifully renovated 2-bedroom + loft, 2-bath condominium offering approximately 1,600 square feet of bright, open living space. Perfectly positioned overlooking tranquil water and the golf course, this exceptional home combines modern updates with soaring architectural details in one of Oldsmar's most desirable communities. The impressive great room welcomes you with dramatic vaulted ceilings, abundant natural light, and a striking spiral staircase leading to a versatile loft—ideal for a home office, media room, or guest space. The remodeled kitchen features crisp white cabinetry, quartz countertops, stainless steel appliances, recessed lighting, and a breakfast bar that opens seamlessly to the living and dining areas. The spacious primary suite offers peaceful water views, private access to the screened lanai, a custom walk-in closet, and a beautifully renovated en-suite bath complete with a luxurious oversized walk-in shower and dual vanities. The generous second bedroom is located near the updated guest bath, providing privacy for family or visitors. Step outside to the expansive screened lanai and enjoy picturesque views of the pond and golf course—the perfect setting for your morning coffee or relaxing evenings. Features You'll Love 2 Bedrooms + Spacious Loft 2 Fully Updated Bathrooms Approximately 1,600 Sq. Ft. Soaring Vaulted Ceilings Dramatic Spiral Staircase Beautifully Renovated Kitchen with Quartz Counters Stainless Steel Appliances Luxury Vinyl Plank Flooring Throughout Custom Walk-In Closet Oversized Primary Shower with Designer Tile Full-Size Washer & Dryer Large Screened Lanai Water & Golf Course Views Assigned Covered Parking Located just minutes from shopping, restaurants, parks, Tampa International Airport, and some of the area's best beaches, this move-in-ready home offers the perfect blend of comfort, style, and convenience. Schedule your private showing today and discover everything this exceptional Oldsmar home has to offer! Newer AC 3/2022.

60 St Andrews Place Unit 60, Oldsmar

$548,000

3 Beds ⋅ 2 Baths ⋅ Bays End SubDv. ⋅ 34677 Zip Code ⋅ TB8521571 MLS ⋅ Active Status

Roof 2026!! Welcome to Bays End, a hidden gem community offering a peaceful setting with convenient access to everything the area has to offer. This well-maintained 3-bedroom, 2-bathroom home features a spacious and inviting layout. Enter to an open living room that flows into the dining area. The updated kitchen showcases beautiful cabinetry, generous storage, and plenty of workspace. The heart of the home is the family room, with vaulted ceilings and a fireplace create a warm and open space. The spacious primary suite offers walk-in closets and a tastefully updated en-suite bathroom. Split plan with two bedrooms and a bathroom. Step outside to your own private backyard retreat featuring a pool, spa, paver patio, and fully fenced yard—perfect for relaxing, entertaining, or enjoying Florida's year-round sunshine.

854 Christina Circle, Oldsmar

$569,900

3 Beds ⋅ 2 Baths ⋅ Kingsmill SubDv. ⋅ 34677 Zip Code ⋅ TB8515993 MLS ⋅ Active Status

Welcome to Kingsmill in the highly sought-after East Lake Woodlands community! LISTED BELOW APPRAISED VALUE! This beautifully maintained waterfront home features 3 bedrooms, 2 bathrooms, and a 2-car garage, and has been lovingly cared for by its original owner. From the moment you arrive, you'll be impressed by the home's private cul-de-sac location and newly paved driveway. Step inside to discover luxury vinyl flooring that flows seamlessly throughout the main living areas and bedrooms. High ceilings and natural light create an open, airy atmosphere throughout the home. The spacious living and dining room combination is highlighted by a cozy fireplace, creating the perfect setting for both everyday living and entertaining. The kitchen features wood cabinetry, solid-surface countertops, a tile backsplash, brand new matching GE stainless steel appliances, and a breakfast nook overlooking the water. A full pocket sliding glass door opens to the lanai, allowing you to fully enjoy the tranquil lake views. The primary suite is a true retreat, offering water views and private access to the screened porch through sliding glass doors. The ensuite bathroom features dual vanities, a garden tub, a walk-in tiled shower, tile flooring, and two walk-in closets. The secondary bedrooms provide ample storage with built-in closets, while the guest bathroom includes tile flooring, a wood vanity with a solid-surface countertop, and a walk-in tiled shower. Additional features include an indoor laundry room with brand new washer and dryer included, a freshly painted garage floor, a 2021 roof, 2026 water heater, and 2017 HVAC system. Enjoy maintenance-free living with low monthly HOA fees that include lawn maintenance and trash service. Located within the gated East Lake Woodlands community, residents have the option to join Ardea Country Club, which offers exceptional amenities including two championship 18-hole golf courses, a fitness center, restaurant, swimming pools, tennis courts, racquet sports facilities, and more. Conveniently located near shopping, dining, airports, and some of Florida's most beautiful beaches, this home offers the perfect combination of comfort, convenience, and resort-style living. Don't miss this opportunity—schedule your private showing today!

4856 Westchester Court, Oldsmar

$350,000

3 Beds ⋅ 3 Baths ⋅ Hayes Park Village SubDv. ⋅ 34677 Zip Code ⋅ TB8501214 MLS ⋅ Active Status

NEW PRICE! Location, location, location is the key to finding the perfect home - and this one delivers on every level. If you have been searching for a place that blends character, convenience, and community, look no further. This charming 3-bedroom home with an attached garage, sits in the picturesque neighborhood of Hayes Park Village, a community that feels like a slice of the French Quarter right here in Florida. Nestled in the heart of the City of Oldsmar, this home offers the best of old-world-charm with modern comfort. Oldsmar is a great City known for having more parks per sq. mile than any other city in the state along with excellent schools and an abundance of activities for all ages. Also, the home of Tampa Bay Downs and Tampa Bay Skating Academy. It is a place where community pride runs deep and quality of life comes naturally. The homes inviting wrap-around porch sets the tone from the moment you arrive. Enjoy your morning coffee as you look out to the neighborhood courtyard complete with a welcoming fire pit, creating the perfect setting for neighborhood gatherings. Inside the home, gleaming hardwood floors flow through an open concept living space that feels both spacious and cozy. The kitchen is beautifully appointed with granite countertops and 36" cabinets and a center island that anchors the room- ideal for cooking, entertaining or simply enjoying daily life. A convenient first floor powder room adds practicality for guest and family alike. The master suite opens to a second floor balcony that overlooks the lake and Richard B. Rogers Park. The Master bedroom also features a tray ceiling with crown molding and an upgraded bathroom with frameless glass shower enclosure and a walk-in closet. Two additional ample sized bedrooms and a guest bath complete the upstairs. THIS HOME HAS BEEN WELL MAINTAINED; ROOF IS JUST OVER A YEAR OLD AND THE AC IS JULY OF 2025, WATER HEATER REPLACED IN 2024. The PERFECT LOCATION connects TAMPA to PINELLAS COUNTY. Close commute to Tampa International Airport and International Mall. Within minutes of Clearwater and downtown Safety Harbor, Approximately 30 minutes to the Gulf Coast Beaches.Current owner pays $1081 for FLOOD INS. Policy is transferable to new Buyer. NEVER FLOODED.

208 Cutlass Way, Oldsmar

$189,900

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code ⋅ TB8485863 MLS ⋅ Active Status ⋅ East Lakes BLDG.

Welcome home to peaceful, easy living in the heart of East Lake Woodlands. This beautifully updated 2-bedroom, 2-bathroom condo features brand-new waterproof laminate flooring throughout the main living areas for a modern, low-maintenance feel, with cozy carpet exclusively in the bedrooms. Enjoy ultimate peace of mind with a newer HVAC system (only 15 months old). Brand new water heater and new brand new AC 2026 for both. Dishwasher does not work. The spacious primary suite serves as a true retreat, highlighted by an impressive three walk-in closets, providing exceptional storage rarely found in condo living. Residents can enjoy tranquil surroundings and unwind at the community pool, creating a relaxed Florida lifestyle. Conveniently located in Oldsmar, this home offers easy access to shopping, dining, beautiful Gulf beaches, and Tampa International Airport, making commuting and travel effortless.

303 Martha Lane Unit 303, Oldsmar

$450,000

3 Beds ⋅ 3 Baths ⋅ Seaside Estates SubDv. ⋅ 34677 Zip Code ⋅ TB8462407 MLS ⋅ Active Status ⋅ 116 BLDG.

Elevated Gated Community. WATERFRONT 3 bedrooms, 3 full baths plus a tandem 2-3 car garage with sliders to a first, second and third floor patios, the patios overlook the dock and boat slip that come with the townhome. The kitchen is open to the dining and family rooms. One bedroom and full bath is located on the main level, while the master suite, and the 3rd bedroom both with full bathrooms are located on the top floor along with the laundry closet. The oversized master features two walk-in closets and floor to ceiling windows with sliders out to one of two private balconies in the home. The master bath has a walk-in shower, garden tub, and dual sinks. High ceilings throughout the home. A must see! Seller is motivated! LET'S MAKE A DEAL!

116 Brent Circle, Oldsmar

$829,000

4 Beds ⋅ 4 Baths ⋅ Warwick Hills SubDv. ⋅ 34677 Zip Code ⋅ TB8419306 MLS ⋅ Active Status

PRICE ADJUSTMENT! Buy now to get settled in over the summer! Welcome to Warwick Hills within the Eastlake Woodlands community! Two-story residence awaits on a large corner lot. A stately presence greets you with elegant landscaping. Side-entry 3-car garage & extended driveway. Step inside through double doors into the grand foyer. Formal living and dining rooms, as well as a spacious family room featuring a wood-burning fireplace. Sliding glass doors open up to the lanai and pool. The kitchen and family room blend seamlessly with an open floor plan, highlighted by wood cabinets, granite counter tops, island, wet bar, and multiple pantries. Ideal floor plan for everyday living and entertaining. Relaxing views of the pool & spa with tropical landscaping. A versatile office on the main floor can easily serve as a 5th bedroom. Full-size laundry room.All bedrooms on 2nd floor. Upstairs, the grand primary suite welcomes you with double-door entry and a private sitting area. Two walk-in closets and a renovated bathroom featuring soaking tub, dual vanities, private water closet, and new glass-enclosure. The 2nd floor also features 3 additional bedrooms and 2 more full baths. Property improvements include exterior painted (2023), interior painted (2026) roof (2022), A/C units (2018 & 2019). Hurricane shutters for windows & doors. Ardea Country Club: Residents can take advantage of golf, tennis, dining, and social memberships. With easy access to Hillsborough and Pasco counties, this centrally located home is just minutes to shopping, dining, top-rated schools, and all that the Tampa Bay area has to offer.

2328 Warwick Drive, Oldsmar

$199,900

2 Beds ⋅ 2 Baths ⋅ East Lake Woodlands Condo SubDv. ⋅ 34677 Zip Code ⋅ TB8366634 MLS ⋅ Active Status ⋅ Building 1 BLDG.

Here is your opportunity to purchase a great condo in the popular East lake Woodlands development. This beautiful 2 bedroom, 2 full bath condo has plentiful closet space, the primary bedroom has 3! Unit has its own washer and dryer located in the enclosed porch just off the living room. All furniture is included! Both bathrooms have been remodeled along with the kitchen. The kitchen has quartz countertops, new cabinets and stainless appliances. You also get one covered parking spot under the carport. Plenty of guest parking. Walking distance to the pool. Close to schools, shopping, dining and the movie theaters. New acrylic windows and new screens will be installed on the porch by the end of May.

113 Nina Way Unit 113, Oldsmar

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