Location: Oldsmar
Do Not Show Listings
1811 FOREST DR, OLDSMAR, FL 34677
$459,90045 Days on yellowkey MLS ID: TB8491038
REDUCED by $4,100 (0.9%) on 05/08/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2142 Built: 1973 Tax: $6,771 (2025)Community: Harbor Palms-Unit ThreeSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,771
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
Remarks: SELLERS ARE OFFERING $5000 CREDIT TOWARDS BUYER'S CLOSING COSTS AND ARE VERY MOTIVATED!!! Come enjoy your next recently updated pool home located in Oldsmar with an open living room and dining room that feature vinyl floors throughout the entire interior of the home! This home attributes natural light throughout the whole house and makes a perfect setup for a family and gatherings. Come see your stylish kitchen that has built-in stainless appliances, marble countertops, and a natural stone ledger backsplash that enjoys a bar setup to host company with the pool easily accessible just steps away through the glass doors to the outside. The interior has been recently painted along with a new A/C Unit installed in 2025 so you have no problem getting a break from the heat. For your peace of mind, the roof along with the hot water heater were replaced in 2024. Delightfully, you are in close proximity to Sheffield Park and is a short drive to well known Philippe Park. If you don't want to go anywhere then there is a screened-in pool for your enjoyment without ever leaving the house. The seller has a recently passed 4 point inspection in July of 2025 and cuts down on uncertainty for the next owner of this home.
Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)
Listing Agent: Brian Mathay (813-482-6097)
50 WILLOWOOD LN, OLDSMAR, FL 34677
$1,499,90086 Days on yellowkey MLS ID: TB8475420
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4172 Built: 1987Monthly Fee: $240 Tax: $8,709 (2024)Community: Deerpath Unit OneSingle Family
Taxes:$8,709
Elementary School: Cypress Woods Elementary-PN
Tax Year: 2024
Remarks: Tucked away on a quiet lane in the highly desirable East Lake Woodlands community, this beautifully updated residence at 50 Willowood Ln offers exceptional space, flexibility, and privacy—perfect for today’s modern lifestyle. Featuring 4-6 bedrooms: 4 true bedrooms PLUS a dedicated office (5th bedroom) and an additional flex room with its own private entrance (ideal as a 6th bedroom, guest suite, or in-law space), this home provides endless possibilities. Of note, two bedrooms are located upstairs, with a jack-and-jill bath and massive loft area, also with infinite uses for entertaining, studying, working, gaming or an additional family room. Step inside to discover a light-filled, open-concept layout with generous living and dining areas designed for both everyday comfort and entertaining. The spacious kitchen flows seamlessly into the main living space and offers ample cabinetry, counter space, and a functional layout for the home chef. The primary suite is a private retreat, complete with an en-suite bath and ample closet space, while the secondary bedrooms are well-sized and thoughtfully positioned. The separate office provides the perfect work-from-home setup, and the versatile flex room—with its own entrance—adds incredible value and adaptability. Enjoy Florida living outdoors with a serene backyard setting, with almost 2,000sf of screened-in pool/lounge space, perfect for relaxing or entertaining. Located within the gated East Lake Woodlands community, residents enjoy access to golf, tennis, and country club amenities (optional membership), all while being just minutes from top-rated schools, shopping, dining, and Gulf Coast beaches. Key Highlights include 4 Bedrooms + Office (5th Bedroom Option) + Flex Room (6th Bedroom Option with Private Entrance), a Flexible floor plan with a multitude of options. This home is located in a sought-after double-gated community, convenient to beaches, airports, shopping, and dining. This is a rare opportunity to own a highly adaptable home in one of Oldsmar’s most coveted neighborhoods—schedule your private showing today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Melissa Pranzo (646-509-7350)
470 HICKORYNUT AVE, OLDSMAR, FL 34677
$765,00060 Days on yellowkey MLS ID: TB8485715
REDUCED by $30,000 (3.8%) on 05/08/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2922 Built: 1987Monthly Fee: $110 Tax: $10,515 (2025)Community: East Lake WoodlandsSpa: YesSingle Family
Taxes:$10,515
Remarks: One or more photo(s) has been virtually staged. Located inside the highly desirable gated community of East Lake Woodlands, this spacious 4-bedroom, 2.5-bath residence offers an expansive 2,922 sq ft of living space on an oversized lot with peaceful water views. Step inside to soaring ceilings and an open, light-filled floor plan designed for both everyday living and entertaining. The home features expansive living areas including a formal living and dining room and a large family room with fireplace. New Luxury Vinyl Plank flooring installed in 2026 runs throughout the main living areas, creating a modern and cohesive look, while new carpet installed in 2026 adds comfort to the guest bedrooms. The updated kitchen features granite countertops and stainless-steel appliances, flowing seamlessly into the main living space and breakfast area—perfect for gatherings and everyday living. The spacious primary suite offers direct access to the pool area along with a private bath and generous closet space. Enjoy Florida living at its best with a screened pool and lanai overlooking a tranquil pond, providing both privacy and relaxing water views. The home also features fresh exterior paint completed in 2026 and a 3-car garage, all situated on a generous homesite within this established golf-course community. Residents of East Lake Woodlands have the option to join the Ardea Country Club, a recently renovated club offering two championship golf courses, tennis and pickleball courts, fitness facilities, resort-style pool, and multiple dining venues. The club provides a vibrant social calendar and family-friendly amenities, creating a true country club lifestyle right inside the community. Located just minutes from shopping, dining, top-rated schools, and major commuter routes, this home offers convenient access to Tampa International Airport, Gulf beaches, and the best of the Tampa Bay area. Close to all the Tampa Bay Area has to offer; Championship golf courses, Tampa International Airport, NHL, NFL, MLB events, Grand Prix, PGA events, fine dining, concerts, parks, biking trails, BMX events, and more. Begin Your Paradise Life Today.
Listing is courtesy of: PARADISE LIFE REALTY (727-698-2996)
Listing Agent: Lou Tutko (727-698-2996)
3073 DUANE AVE, OLDSMAR, FL 34677
$455,000265 Days on yellowkey MLS ID: TB8417476
REDUCED by $4,000 (0.9%) on 05/08/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2122 Built: 1973 Tax: $1,936 (2024)Community: West Oldsmar Sec 1Single Family
Taxes:$1,936
Elementary School: None
High School: None
Middle School: None
Remarks: Located in a quiet and friendly Come and see this beautiful house with a lot of potential. No HOA ,It has a spacious master bedroom with an in-suite bathroom and a large walk-in closet. Outside, you’ll find a large detached porch with big storage, perfect for storing a golf cart, bikes, kayaks, or motorcycles—or transform it into two bedroom, gym, or office or a party place . The backyard is a standout, surrounded by trees that keep the home cooler and energy bills lower. It’s perfect for relaxing or entertaining. . Enjoy gorgeous sunsets or cast a line off the nearby pier at one of the area’s best parks. Buyer and/or buyers agent to verify all room sizes. Seller will pay a coverage flood insurance for the first year.
Listing is courtesy of: S P O R T REALTY GROUP INC. (813-452-8301)
Listing Agent: Madelin Martinez (813-359-7784)
709 LEMONWOOD DR, OLDSMAR, FL 34677
$345,00087 Days on yellowkey MLS ID: TB8475735
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1667 Built: 1973 Tax: $4,799 (2024)Community: Harbor Palms-Unit FiveSingle Family
Taxes:$4,799
Remarks: Welcome to this well-maintained 3-bedroom, 2-bath home offering 1,667 square feet of comfortable living space on a spacious 60x100 lot, located on a quiet street in desirable Oldsmar. This home features newer appliances, a 2025 hot water heater, and a 2022 AC system, providing peace of mind for years to come. Inside, you’ll find new carpet in Bedrooms 2 and 3, along with a bright and functional layout that includes both a living room and family room with a wood-burning fireplace, perfect for relaxing or entertaining. The kitchen is enhanced with a new slider and updated windows in the living room and family room, allowing for abundant natural light and easy access to the backyard. An inside laundry room adds everyday convenience. Enjoy the tranquility of the neighborhood while having direct access to Harbor Palms Nature Park, offering walking and biking trails just steps away. Ideally located less than 20 minutes from Clearwater Beach, with nearby shopping, dining, and major roadways, this home delivers the perfect blend of comfort, location, and Florida lifestyle. Schedule your private showing today—this Oldsmar opportunity won’t last!
Listing is courtesy of: PEOPLE'S CHOICE REALTY SVC LLC (813-933-0677)
Listing Agent: Jay Hundt Pa (813-765-9438)
204 BENGAL CIR, OLDSMAR, FL 34677
$715,00065 Days on yellowkey MLS ID: O6388593
REDUCED by $20,000 (2.7%) on 05/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2429 Built: 2013Monthly Fee: $65 Tax: $5,728 (2025)Community: Bungalow Bay EstatesSpa: YesSingle Family
Taxes:$5,728
Elementary School: Oldsmar Elementary-PN
Remarks: Stunning custom home with luxury upgrades, thoughtful design, and handicap-friendly features throughout. Perfectly designed for entertaining, this home blends elegant finishes with comfortable indoor-outdoor living. A grand foyer welcomes you into the spacious great room where a wall of three-pane sliding glass doors fully tucks away, seamlessly connecting the living space to the covered patio and pool area. The gourmet chef’s kitchen features granite countertops, high-end appliances, custom cabinetry, designer lighting, and a large island with seating and additional storage. A generous walk-in pantry closet provides excellent storage and functionality. The home is wired for sound with built-in surround speakers in the living room and screened porch, plus audio ports throughout the house so speakers can easily be connected in every room. The luxurious primary suite features a tray ceiling and three oversized walk-in closets, one currently used as a private office. The spa-like primary bath includes wraparound dual vanities, an air-jetted soaking tub, and a spacious shower with rain shower head and therapy jets. The suite also offers direct access to the patio and pool. Designed with accessibility in mind, the home includes extra-wide doorways for wheelchair access and a zero-threshold primary shower. Step outside to your private backyard retreat with a heated saltwater pool and spa featuring PebbleTec finish and a self-cleaning pop-up system, all set within a beautiful paver deck and screened porch with generous ceiling fans—perfect for year-round Florida living. Additional highlights include central vacuum, oversized laundry room, an oversized two-car garage with workshop space and service door, PVC privacy fencing, and irrigation on reclaimed water. Major updates provide peace of mind: New AC (March 2026), roof replaced late 2025, and water heater replaced late 2025. Conveniently located near waterfront parks, shopping, Tampa International Airport, and the beautiful Pinellas County beaches. Home has never flooded-high and dry!
Listing is courtesy of: GILLEN & ASSOCIATES (321-947-0912)
Listing Agent: Cynthia Weclew (813-507-7818)
4738 PEBBLE BROOK DR, OLDSMAR, FL 34677
$535,000125 Days on yellowkey MLS ID: TB8460875
2 Days Off yellowkey (back on 5/7/2026)
REDUCED by $14,000 (2.6%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1938 Built: 1996Monthly Fee: $470 Tax: $4,041 (2025)Community: Cross Creek - Unit TwoSingle Family
Taxes:$4,041
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy a Relaxing Lifestyle in the desirable Gated, Golf Community of East Lake Woodlands and the convenience of Less Maintenance responsibilities! This home provides Privacy and Stunning Water Views with a Large, Covered Screened Lanai to enjoy that morning cup of coffee or evening glass of wine. Plus it’s situated in the preferred Zone X so no flood insurance is required. An added bonus is the Cul de Sac location and longer driveway for more parking for family and guests. Volume Ceilings, Crown Molding and an Open Concept highlight a versatile floor plan featuring 2 Bedrooms plus an Office or Den - complete with Custom Paneling, Spacious Desk and Bookcase and even the Luxury of a Wood Burning Fireplace! Open to the generous 28’ x 18’ Great Room, the bright Kitchen features an Eat-In Breakfast Area, Bay Windows with Plantation Shutters, Double Ovens, French Door Fridge and plenty of storage. The Primary Suite features 2 Walk-In Closets complete with Custom Built-in Shelving and Pull-Down Clothing Racks and a Large Bath with Dual Vanities, Large Soaking Tub and Separate Shower. Relax since the reasonable HOA fee includes Lawn Maintenance with Mowing, Fertilizing and Mulching, Cable TV and Internet, Trash and Recycling Collection, a Sparkling Community Pool and Spa for Cross Creek residents, Escrow Reserves, Pressure Cleaning of Roofs and Exterior Painting every 7 years. Home Updates include New Water Heater in Dec. 2025, New Tile Roof in 2019, A/C Unit New in 2018. Washer and Dryer included in the sale plus Manual and Remote-Controlled Exterior Hurricane Shutters and a Generac Generator. This long-time owner had no issues with the 2024 Hurricanes. Enjoy that Gorgeous View and put your touches on this home since this amazing price takes updating into account. All this in a Great Location convenient to Tampa International Airport, beautiful Beaches, Medical Facilities, Professional Sporting Events and Fine Dining. A variety of memberships to Ardea Country Club are available for additional fees and include access to 2 Golf Courses, a Fitness Center, Heated Lap Pool and Freeform Pool, Pickle Ball and Tennis plus Dining and a host of Activities and Events!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Claudia Tweed (727-433-4596)
1204 FORESTWOOD DR, OLDSMAR, FL 34677
$315,00016 Days on yellowkey MLS ID: O6402042
0 Days Off yellowkey (back on 5/7/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1186 Built: 1984Monthly Fee: $35 Tax: $2,622 (2025)Community: Hamlets Of Forest Lakes TheSpa: NoSingle Family
Taxes:$2,622
Remarks: Picture yourself at 1204 Forestwood Dr, a residence recently refreshed with fresh interior paint and new appliances throughout. A cozy fireplace adds comfort, complementing the kitchen's all stainless steel appliances. The exterior features a covered patio that extends to a fully fenced in backyard. Ready to enjoy stylish updates and outdoor living. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
413 COUNTRY CLUB DR, OLDSMAR, FL 34677
$379,90037 Days on yellowkey MLS ID: O6396122
REDUCED by $5,000 (1.3%) on 05/07/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1323 Built: 1959 Tax: $3,829 (2024)Community: Oldsmar Country Club Estates Sec 2Single Family
Taxes:$3,829
Remarks: Welcome to this stunning, fully renovated 3-bedroom, 2-bathroom waterfront home located in the highly desirable Oldsmar Country Club Estates. Situated on a spacious 0.21-acre lot with no HOA, this property offers a rare opportunity to enjoy true Florida living with direct water access. Follow the scenic water trail right from your backyard all the way out to Tampa Bay, making this a dream for kayaking, paddleboarding, and outdoor enthusiasts. From the moment you arrive, you’ll be drawn in by the beautiful curb appeal, manicured landscaping, and inviting exterior. Inside, luxury vinyl tile flooring flows throughout the home, complemented by an open, modern layout filled with natural light. The renovated kitchen features stainless steel appliances, quartz countertops, and ample cabinetry, perfectly blending style and functionality. The primary suite offers a spa-like retreat with an updated bathroom, modern vanity, designer lighting, and a tiled walk-in shower. Sliding doors lead to an expansive backyard where tranquil waterfront views set the stage for relaxing evenings, entertaining, and unforgettable sunsets. Beyond the home, enjoy an unbeatable lifestyle where you can walk, bike, or even take your golf cart to nearby attractions including Mobbly Bayou Beach Park, a public boat launch to Tampa Bay, Tampa Bay Pickleball, Veterans Park, Bicentennial Park, RE Olds Park, and more. You’re also just minutes from local favorites like Empower Adventures Zip Line and the Oldsmar Organic Community Garden. With Tampa International Airport only about 20 minutes away, convenience meets lifestyle in this exceptional property. This is a rare chance to own a fully updated waterfront home with no HOA in one of Oldsmar’s most established and sought-after communities.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Julian Jackson (301-272-4192)
400 SHORE DR E, OLDSMAR, FL 34677
$1,000,00078 Days on yellowkey MLS ID: TB8478151
3 Days Off yellowkey (back on 5/7/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1890 Built: 1957 Tax: $3,995 (2025)Community: Country Club Add To Oldsmar RevSingle Family
Taxes:$3,995
Remarks: Under contract-accepting backup offers. The Ultimate Waterfront Canvas: 150ft of Panoramic Bay Frontage. Secure a legacy-grade homesite on one of the most expansive waterfront lots in Oldsmar. Situated on almost ¾ acre on the prettiest street in Oldsmar, 400 Shore Drive E offers a rare 150 feet of direct, unobstructed frontage on Safety Harbor. This is a premier opportunity for a visionary buyer or elite builder to bypass the limitations of existing construction and design a bespoke custom estate from the ground up. While the current structure is a teardown (sold as-is), its presence provides a significant footprint and potential impact fee advantages for your new architectural masterpiece. Experience total privacy and some of the most breathtaking, wide-water sunset views found anywhere in the Tampa Bay region. Just minutes from the refined trails of RE Olds Park and the area’s top dining, this location perfectly balances secluded coastal living with urban convenience. Don’t just buy a home—build a landmark on the water’s edge.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Crystal Tipton, Mrs (813-436-7229)
1802 CHINABERRY DR, OLDSMAR, FL 34677
$375,000202 Days on yellowkey MLS ID: TB8439498
5 Days Off yellowkey (back on 5/7/2026)
INCREASED by $6,000 (1.6%) on 04/30/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1358 Built: 1972 Tax: $865 (2024)Community: Harbor Palms-Unit OneSpa: NoSingle Family
Taxes:$865
Remarks: Easily 3 Bedroom (EVEN 4) - Total Renovation - Block/Slab Home - Large Indoor Laundry - 2 Car Garage - New Roof - New AC - New Water Heater - New Kitchen - Solid Wood Cabinets - Solid Surface Counters - New Bathrooms - New Floors - Interior and Exterior Paint - Landscaping - Large Fenced Yard -
Listing is courtesy of: FOXX AND ASSOCIATES (877-538-6868)
Listing Agent: Dan Nease (727-354-2222)
420 CYPRESS VIEW DR, OLDSMAR, FL 34677
$485,0003 Days on yellowkey MLS ID: TB8505264
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1870 Built: 1998Monthly Fee: $140 Tax: $4,405 (2025)Community: Preserve At Cypress Lakes Ph I TheSingle Family
Taxes:$4,405
Remarks: Welcome to your private slice of paradise in Oldsmar! Updates include a 2026 AC, 2026 Roof, and 2021 Water Heater for peace of mind. This beautifully maintained three-bedroom, three-bathroom pool home offers the perfect blend of comfort and Florida living - nestled on a premium lot with preserve views, no rear or side neighbors, and only one neighboring home for added privacy. Additional updates include whole-house water and air filtration added in 2025, and the home was painted in 2021. From the moment you arrive, you’ll be greeted by easy-to-maintain tropical landscaping that enhances the home’s curb appeal. Step inside to a light and bright interior featuring a welcoming front living room with a cozy fireplace and crown molding that continues throughout the home. High ceilings create an open, airy feel as you move through the thoughtfully designed layout. The spacious kitchen is conveniently located to your right and is well-equipped with abundant cabinetry, a separate pantry for extra storage, and a charming breakfast nook. A laundry room sits just off the kitchen for added convenience. The kitchen opens seamlessly to the main living area, where wood-look vinyl flooring, a ceiling fan, and views of the pool make it the perfect space to relax or entertain. The primary suite is generously sized with high ceilings, wood-look vinyl flooring, and an attached bathroom featuring a dual-sink vanity, soaking tub, and separate glass-enclosed shower. Additional bedrooms are comfortably sized and include ceiling fans, offering flexibility for family, guests, or a home office. Step outside and truly embrace the Florida lifestyle. The screened-in pool area is surrounded by a serene, tree-lined preserve, creating a peaceful and private outdoor retreat. Enjoy a covered space ideal for dining, grilling, or simply lounging poolside year-round. Located near highly rated schools, as well as a variety of dining and shopping options, this home offers both convenience and tranquility in one desirable package. Schedule your showing today!
Listing is courtesy of: EXP REALTY LLC (866-308-7109)
Listing Agent: Jeffrey Borham, Pa (866-308-7109)
382 FOUNTAINVIEW CIR, OLDSMAR, FL 34677
$520,0004 Days on yellowkey MLS ID: TB8499334
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1875 Built: 1995Monthly Fee: $95 Tax: $5,232 (2025)Community: Fountains At Cypress Lakes TheSingle Family
Taxes:$5,232
Remarks: Welcome home to this stunning, move-in ready 4 bedroom, 2 bath split floor plan in one of Oldsmar's most sought-after neighborhoods - and zoned for some of the top-rated schools in the area. From the moment you walk in, you'll notice the difference that thoughtful, high-quality updates make. Soaring vaulted ceilings and elegant columns greet you in the formal living room, while French doors open to a versatile den or 4th bedroom. The heart of the home is a beautifully updated gourmet kitchen featuring shaker-style soft-close cabinetry, quartz countertops, subway tile backsplash, stainless steel appliances, a breakfast bar, and a sunny breakfast nook ... all flowing naturally into the family room and out to the screened porch through a slider, perfect for that indoor-outdoor Florida lifestyle. The primary suite is a true retreat, complete with a spa-inspired bath boasting dual sinks, quartz countertops, and a step-in shower. Two additional bedrooms share a well-appointed bath. Throughout the home you'll find brand new engineered hardwood and LVP flooring, freshly painted interiors, popcorn ceilings removed, and updated baths - every detail has been addressed. And the big ticket items? All taken care of. Brand new roof (May, 2026), newer appliances, new garage door motor, new back pavers, and a fully fenced lot with complete privacy,fresh landscaping, and a freshly painted exterior in warm, natural tones that give the home incredible curb appeal. This is the one you've been waiting for — all the charm, all the updates, and an unbeatable Oldsmar location close to Gulf beaches, parks, golf courses, shopping, and Tampa International Airport.
Listing Agent: Marianne Knowles (813-720-9201)
313 JEFFERSON AVE S, OLDSMAR, FL 34677
$449,00011 Days on yellowkey MLS ID: TB8502786
REDUCED by $1,000 (0.2%) on 05/07/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1841 Built: 1940 Tax: $4,298 (2025)Community: Oldsmar Rev MapSingle Family
Taxes:$4,298
Remarks: Seller is willing to contribute up to $9,000 toward buyer closing costs and/or allowable credits with an acceptable offer. Open House: Saturday, May 9th, from 1:00 PM to 3:00 PM. Fully renovated and move-in ready, this 3-bedroom, 2-bath home features 1,841 square feet of updated living space in a desirable area of Oldsmar. Recent improvements include a brand-new roof, new windows, fresh paint, brand-new appliances, and a fully refurbished HVAC system, creating a true turnkey opportunity. Inside, the home offers a spacious living area filled with natural light, a covered front porch, and an upstairs bonus room that can function well as a home office, playroom, guest area, kids room, or other flexible living space. The upstairs bonus room was not included in the total bedroom count. Situated on a double lot, the property includes ample outdoor space with room for a shed, carport, or future improvements. Conveniently located near parks, schools, shopping, dining, and other local amenities, this home brings together style, comfort, and convenience in one well-updated property. A clean 4-point inspection, wind mitigation report, WDO report, and recent appraisal are available. The recent appraisal came in at $475,000.
Listing is courtesy of: GRAYSTONE REAL ESTATE (727-201-4011)
Listing Agent: Bradley Dreher (863-346-0500)
50 KELLEYS TRL, OLDSMAR, FL 34677
$1,200,0004 Days on yellowkey MLS ID: TB8504781
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3240 Built: 1993Monthly Fee: $185 Tax: $7,792 (2025)Community: Turtle Creek Unit-OneSingle Family
Taxes:$7,792
Remarks: Welcome to an exceptional residence at 50 Kelleys Trail, nestled within the prestigious gated enclave of Turtle Creek within East Lake Woodlands in Oldsmar. This refined home embodies effortless elegance and elevated Florida living, offering a seamless blend of sophistication, comfort, and privacy. From the moment you enter, you’re greeted by soaring ceilings, abundant natural light, and thoughtfully designed living spaces that create an inviting yet upscale atmosphere. The open-concept layout flows beautifully, ideal for both intimate gatherings and grand entertaining. The kitchen serves as the heart of the home, featuring generous workspace, ample cabinetry, and a layout designed for both functionality and style. The primary suite is a true retreat, offering a serene escape with spacious proportions and a well-appointed en-suite bath. Step outside to your private outdoor setting, where you can unwind in tranquility or entertain guests while enjoying Florida’s year-round sunshine. Whether relaxing or hosting, this space offers the perfect backdrop for a luxury lifestyle. Located within one of Oldsmar’s most sought-after golf course communities, residents of East Lake Woodlands have access to optional resort-style amenities, including championship golf, tennis, fitness, and social experiences. Ideally positioned near upscale dining, boutique shopping, top-rated schools, Tampa International Airport, and the Gulf Coast’s renowned beaches, this home offers both convenience and exclusivity. Experience refined living in one of Oldsmar’s premier communities—schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
549 LONGWOOD CIR, OLDSMAR, FL 34677
$525,0004 Days on yellowkey MLS ID: A4692285
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1344 Built: 1984Monthly Fee: $30 Tax: $5,336 (2025)Community: Manors Of Forest Lakes TheSingle Family
Taxes:$5,336
Remarks: Welcome to your private retreat in the heart of Oldsmar. Located in the desirable Longwood community, this beautifully maintained home offers the perfect blend of comfort, charm, and Florida living. Surrounded by mature landscaping and peaceful streets, 549 Longwood Circle features spacious living areas, abundant natural light, and an inviting layout ideal for both entertaining and everyday living. Step outside to enjoy a relaxing backyard setting with room to unwind, host gatherings, or create your own outdoor oasis. Conveniently located near top-rated schools, parks, shopping, dining, and the Gulf beaches, this home delivers both privacy and accessibility. Whether you're looking for a full-time residence or a seasonal getaway, this property is an incredible opportunity to own a piece of paradise in one of Tampa Bay’s most sought-after communities.
Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)
Listing Agent: Susan Kolesnikov (916-272-9177)
602 BAY LAKE TRL, OLDSMAR, FL 34677
$375,0009 Days on yellowkey MLS ID: TB8503595
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1554 Built: 1983 Tax: $937 (2025)Community: Shoreview Ph ISingle Family
Taxes:$937
Remarks: Located in the Shoreview community of Oldsmar, this home offers a great combination of location, schools, and potential. Zoned for highly rated schools, this home is a smart choice for buyers looking to get into a strong school district while still having the opportunity to make it their own. Set on a peaceful homeowner-owned lake, the property features a private pool and relaxing water views—perfect for everyday living or entertaining. Inside, the home offers a desirable split floor plan for added privacy, a spacious primary suite with a walk-in closet, and an additional flex space/den ideal for a home office, playroom, or second living area. It’s ready for updates, making it ideal for buyers who want to customize and add value over time. You’re just minutes from R.E. Olds Park on Shore Drive, where you can enjoy festivals, outdoor concerts with fireworks over the water, a fishing pier, and beautiful sunset views. The area is also surrounded by waterfront parks offering bike and kayak trails, pickleball, basketball and tennis courts, walking and jogging paths, playgrounds, picnic areas, a small beach, and even a community garden. In addition to all the outdoor amenities, the home is conveniently located near great restaurants, shopping, Tampa International Airport, and the area’s award-winning Gulf beaches. And for peace of mind, the property is high and dry and did not have hurricane flooding or damage. If you’ve been looking for a home in a great location with room to make it your own, this one is definitely worth seeing. Please note: No sight unseen, assignable, or seller financing offers will be considered.
Listing is courtesy of: BRAINARD REALTY (813-922-2891)
Listing Agent: Sandra Santos Garbutt (727-418-1593)
436 LAFAYETTE BLVD, OLDSMAR, FL 34677
$700,000283 Days on yellowkey MLS ID: TB8412856
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2695 Built: 1994 Tax: $10,665 (2024)Community: Oldsmar Rev MapSingle Family
Taxes:$10,665
Remarks: One or more photo(s) has been virtually staged. Must see this 4 bedroom/2.5 bath home with almost 2700 Sq/Ft on one of the highest/majestic lots in downtown Oldsmar! Relax by the wood fireplace with your family in the comfortable living room! Entertain guests, make a fire-pit area, or start your own garden in the expansive backyard with Lanai! Lot is almost a half acre! Fantastic kitchen with granite countertops, stainless steel appliances, plenty of wood cabinets/countertop space and breakfast bar! Large master bedroom with enormous walk-in closet and newly updated master bath with soaking tub, his-and-her sinks and high end stone tile throughout! Take the private glass vacuum elevator to the second floor! Also a dining area, family room and office! Some additional upgrades include: High ceilings, sprinkler system, hurricane windows, whole house instant hot water, water softener/filter system, updated flooring throughout, vinyl fencing, smart-home switches/recessed lighting, updated 2 car garage, block home. Short walk to Bicentennial Park that has a dog park, playground, tennis/basketball/pickleball courts. Also near boat launch, hiking/biking trails, library, fishing pier, museum and schools. Home had no hurricane/water damage! Oldsmar is located centrally in north Pinellas County and is a short drive to world class gulf beaches, Tampa International Airport, sporting venues, theater, shopping, restaurants and much, much more!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Dillon Currier (727-919-4214)
509 CYPRESS VIEW DR, OLDSMAR, FL 34677
$624,90022 Days on yellowkey MLS ID: TB8496854
REDUCED by $9,100 (1.4%) on 05/06/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2084 Built: 1998Monthly Fee: $140 Tax: $4,902 (2025)Community: Preserve At Cypress Lakes Ph I TheSingle Family
Taxes:$4,902
Remarks: REDUCED - SELLER MOTIVATED - PRICED TO SELL ... Plus -Enjoy peace of mind with a seller-provided 1-year Home Warranty. OVERSIDED - FULLY FENCED CORNER LOT in highly desirable area/community of Oldsmar - Preserve At Cypress Lake. 4 Bedrooms, 2 Full Bathrooms, no carpeting, only wide-plank flooring & ceramic tile throughout. Separate Living/Dining Room area (currently being used for home Theatre/Office set up). Enjoy another separate Gathering Room. Large Eat-In Kitchen has Breakfast Bar opening to Gathering Room - perfect for entertaining or everyday living. Stainless Steel Appliances, Granite Counters, Pantry, Roll-Out Cabinetry. Connects to inside Laundry Room includes Washer/Dryer. Primary Bedroom large enough for King size Bedding, large Walk-In Closet. Private Ensuite full Bathroom with separate Shower, Garden Tub and Dual Sinks. Other 3 Bedrooms are adequately sized and share another full Bathroom. Closets are equipped with custom closet systems. Plantation Shutters on formal Living Room, Dining Room and Kitchen windows. The outdoors will not disappoint. Screened Lanai features amazing Pool for all your recreation, relaxation & oversized extra Patio space - all under the screened area. Enjoy additional entertaining or everyday living space with grassed area in back yard and another large Paver Patio - perfect for Grilling, Fire Pit, taking in the sun or sitting under an umbrella. Roof installed in 2017. New Hot Water Heater in 2025. Location is SUPBERB ... close to Forest Lakes Elementary, YMCA, Cypress Forest Recreation Center/Waterpark-Spray Park Splash Pad. Enjoy the nearby Nature Trail, Restaurants, Stores, Oldsmar Flea Market, BMX Complex, Oldsmar Hockey Complex, Ball Parks, convenient to Airport, directly down Tampa Road to all the happenings in Dunedin Main Street, Honeymoon Island and all the other Beaches in the area. Enjoy the holiday festivities this community has sponsored - riding on a horse drawn wagon to view neighborhood houses that have decorated. OLDSMAR & Preserve At Cypress Lakes is the place to be !!!
Listing is courtesy of: FLORIDA HOME REALTY GROUP, LLC (813-523-2280)
Listing Agent: Phyllis Clark (813-523-2280)
307 COUNTRY CLUB DR, OLDSMAR, FL 34677
$385,95012 Days on yellowkey MLS ID: TB8502335
REDUCED by $13,950 (3.5%) on 05/06/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1670 Built: 1960 Tax: $3,567 (2025)Community: Oldsmar Country Club Estates Sec 3Single Family
Taxes:$3,567
Remarks: One or more photo(s) has been virtually staged. HONEY STOP THE CAR! THIS IS THE ONE! LOCATION LOCATION LOCATION! Welcome to this FULLY RENOVATED, PRIME OLDSMAR LOCATION. This RARE OPPORTUNITY is a 3 Bed 2 Bath Home that checks every box for buyers looking for a move-in-ready property and investors searching for a smart opportunity in one of Tampa Bay’s fastest-growing hidden gems. This fully updated residence has been transformed from top to bottom with the modern finishes today’s buyers are chasing. From the moment you walk in, you’ll notice the attention to detail from tile flooring, a beautifully renovated kitchen with stylish cabinetry, upgraded countertops, modern fixtures, refreshed bathrooms, and finishes that make this feel like home. Every inch has been thoughtfully improved so the next owner can simply move in and enjoy. The layout offers the perfect blend of functionality and comfort with spacious living areas, generously sized bedrooms, and plenty of natural light throughout. Step outside and you’ll find ample outdoor space perfect for entertaining, relaxing, or creating your own backyard oasis. But what truly makes this property special is location. Situated in the heart of Oldsmar, you’re minutes from everything to love about the area including Waterfront parks and trails including R.E. Olds Park and Veterans Memorial Park, Close to Toronto Blue Jays spring training games at TD Ballpark, Easy access to shopping, dining, and entertainment throughout Oldsmar, Safety Harbor, and Tampa. Convenient commute to Tampa International Airport, Clearwater beaches, and major employers. Near golf courses, pickleball courts, breweries, and the vibrant charm that continues to make Oldsmar one of Tampa Bay’s most desirable places to live. Whether you’re a first-time homebuyer looking for a turnkey home, someone relocating to Florida, or an investor searching for a high-demand rental opportunity in a rapidly appreciating area, this property delivers. Homes this updated in Oldsmar at this price point don’t last. And opportunities like this? They attract attention fast. Schedule your showing before everyone else does, because this one is built to sell quickly.
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Mark Fazzini (727-485-9981)
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