Displaying: For Sale
Location: Oldsmar
Property Type(s): Single Family
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Oldsmar - 107 properties found
619 TIMBER BAY CIR E, OLDSMAR, FL 34677
$400,0005 Days on yellowkey MLS ID: TB8521146
0 Days Off yellowkey (back on 6/20/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1232 Built: 1983 Tax: $4,130 (2025)Community: Shoreview Ph ISpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,130
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
Remarks: Under contract-accepting backup offers. Former AirBNB is move in ready for Investor or Primary Home Owners! Smart buyers, take note: this move-in ready 3BR/2BA pool home has been thoughtfully updated: fresh interior and exterior paint (2026), a brand-new electrical panel (2026), hurricane-rated windows (2021), replaced ductwork (2021), gutters (2022), and an HVAC system (2018) maintained on a twice-yearly service plan. Sentricon termite protection is in place and serviced annually. Solar panels (2021) keep energy costs low and an EV charging outlet rounds out the practical extras.comes with an assumable flood insurance policy at the highest available coverage level, and you're stepping into meaningful savings from day one. Tucked behind conservation wetlands (Oldsmar Trail) with no rear neighbors — ever — this home offers a level of privacy and natural beauty that's hard to find at any price. Sip your morning coffee on the covered lanai while overlooking your private pool and the peaceful green belt beyond. The fully fenced, pool-ready backyard is made for Florida living — whether that means weekend entertaining or a quiet evening watching the sun set over the wetlands. A storage shed adds handy extra space for tools, pool equipment, or gear. Homes offering this combination of financial incentives, low-maintenance updates, and natural privacy don't come along often. Schedule your private tour today.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Colette Hughes (813-380-6583)
611 TANGERINE DR, OLDSMAR, FL 34677
$345,00026 Days on yellowkey MLS ID: TB8513141
REDUCED by $10,000 (2.8%) on 06/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1382 Built: 1980 Tax: $1,040 (2025)Community: Harbor Palms Unit ElevenSingle Family
Taxes:$1,040
Elementary School: None
High School: None
Middle School: None
Remarks: $5,000 seller credit offered to buyers!!Welcome to 611 Tangerine Drive a well-maintained 3-bedroom, 2-bathroom home located in one of Oldsmar’s most desirable and centrally located communities. Featuring a highly sought-after split floor plan, spacious living areas, and major system upgrades already completed, this home offers the perfect combination of comfort, functionality, and opportunity for a new owner to make the space their own over time. Inside, you’ll find tile flooring throughout the entire main living space, creating a clean, cohesive, and low-maintenance living environment. The split layout provides excellent separation between the primary suite and guest bedrooms, offering both privacy and flexibility for families, guests, or work-from-home living. The spacious primary suite features dual closets along with a beautifully updated master bathroom that adds a more modern touch to the home. The kitchen is equipped with stainless steel appliances and offers excellent functionality with ample cabinet and storage space, while still leaving room for future personalization and design possibilities to match your own style and vision. Several major improvements have already been completed for long-term peace of mind, including full-home repiping, a whole-house water softener and filtration system, and a durable Solar Shield metal roof designed for longevity, efficiency, and reduced maintenance for many years to come. The home has also never FLOODED! This provides additional confidence for future ownership. Outside, the screened-in porch creates the perfect place to relax and enjoy Florida’s year-round weather, while the newer fencing surrounds the backyard and offers both privacy and space for entertaining, pets, or outdoor enjoyment. A spacious two-car garage and abundant storage throughout the home further enhance everyday convenience. Located in the heart of Oldsmar, this property offers outstanding access to everything that makes the Tampa Bay area so desirable. Tampa International Airport, Clearwater Beach, Safety Harbor, Dunedin, and downtown Tampa are all within a convenient drive. Oldsmar is known for its excellent school district, strong community atmosphere, waterfront parks, scenic trails, playgrounds, nature preserves, and outdoor recreation. With its ideal location, major mechanical upgrades, flexible layout, and endless potential to further enhance and customize over time, 611 Tangerine Drive presents an exceptional opportunity in one of northern Pinellas County’s most sought-after communities.
Listing is courtesy of: AMERICAN HERITAGE REALTY, INC. (727-726-7272)
Listing Agent: Sid Vehabovic (727-657-4349)
1811 FOREST DR, OLDSMAR, FL 34677
$439,0005 Days on yellowkey MLS ID: TB8520312
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2142 Built: 1973 Tax: $1,463 (2024)Community: Harbor Palms-Unit ThreeSpa: NoSingle Family
Taxes:$1,463
Tax Year: 2024
Remarks: Nestled in the heart of Oldsmar, this location offers the perfect blend of small-town charm, outdoor recreation, and everyday convenience that makes living in Harbor Palms so desirable. Situated HIGH AND DRY with NO history of flooding, residents enjoy being just minutes from the waterfront parks and trails along Tampa Bay, including R.E. Olds Park, Veterans Memorial Park, and the scenic Upper Tampa Bay Trail. Whether you're spending the day kayaking, biking, fishing, or enjoying one of the area's many community events, Oldsmar embraces an active Florida lifestyle while maintaining a welcoming neighborhood feel. This beautifully renovated 3-bedroom, 2-bathroom POOL home offers over 2,100 square feet of thoughtfully designed living space. From the moment you arrive, the inviting curb appeal sets the stage for the upgrades found throughout the home. Luxury vinyl plank flooring flows seamlessly from room to room, creating a modern and cohesive feel. The front living room transitions effortlessly into the dining area and spacious family room, where a cozy fireplace flanked by built-in shelving serves as the focal point. The centrally located galley-style kitchen is sure to impress with quartz countertops, stainless steel appliances, a statement vent hood, crisp white cabinetry, and a stylish backsplash. The oversized owner's suite offers a private retreat complete with a large walk-in closet and an ensuite bathroom featuring floor-to-ceiling tile and a walk-in shower. Two additional bedrooms are conveniently located near the beautifully updated guest bathroom. A dedicated mudroom with washer and dryer hookups adds extra functionality and storage space. Step outside to the screened-in lanai overlooking the sparkling in-ground pool, creating the perfect setting for relaxing or entertaining guests. Major updates include a new roof and AC in 2024, providing peace of mind for years to come. One of the biggest advantages of living here is the incredible convenience and abundance of nearby amenities. Harbor Palms Nature Park is just steps away and features a kayak launch, scenic boardwalk, walking trails, and an 18-hole disc golf course. Sheffield Park is also nearby with basketball and tennis courts, baseball and softball fields, and a dog park. Centrally located between Tampa, Clearwater, and Palm Harbor, residents enjoy easy access to Tampa International Airport, award-winning Gulf beaches, shopping, dining, entertainment, Mease Countryside Hospital, Tampa Bay Downs, and the Oldsmar BMX Supercross Track. With beautiful parks, a strong sense of community, and a prime Tampa Bay location, it's easy to see why Oldsmar continues to be one of the area's most sought-after places to call home. Schedule your showing today!
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Tiana Lake (727-688-5565)
347 COUNTRY CLUB DR, OLDSMAR, FL 34677
$429,000133 Days on yellowkey MLS ID: TB8475491
REDUCED by $20,000 (4.5%) on 04/05/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1280 Built: 1967 Tax: $1,515 (2024)Community: Oldsmar Country Club Estates Sec 1 RepSingle Family
Taxes:$1,515
Remarks: "Move-In Ready"... Freshly Painted and Beautifully completely Refurbished Single Family Pool Home, (3) Bedrooms, (2) Baths with plenty of storage space, vehicles, boat and golf cart(s) parking. Luxury vinyl flooring throughout this split plan homes interior, picturesque French Door views to the pool and lanai deck, all new kitchen appliances and home systems installed. An expansive corner lot property with plenty of green space, fenced yard and mature landscaping. Enjoy your Florida Lifestyle with family and social gatherings within the updated interior decor or outside in the screened pool and lanai deck area. We'll look forward to your visit.
Listing is courtesy of: PEOPLE'S CHOICE REALTY SVC LLC (813-933-0677)
Listing Agent: Frank Fundora (813-361-2505)
1924 MONTEGO CT, OLDSMAR, FL 34677
$359,90014 Days on yellowkey MLS ID: TB8517782
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1269 Built: 1980 Tax: $5,005 (2025)Community: Bayside Meadows-Phase ISingle Family
Taxes:$5,005
Remarks: **SUPER STARTER HOME!!** What a fantastic house for the price! From the moment you arrive, you’ll be wowed by the striking curb appeal. The freshly painted exterior is complemented by a newer roof and landscaping, with a 30-year dimensional shingle roof installed in 2024 and a transferable 10-year warranty. Inside, the spacious, open floor plan is just as impressive, starting with a leaded glass front door. This move-in ready home has been updated throughout, featuring a tiled great room with a lighted ceiling fan and a large front window that fills the space with natural light. The eat-in kitchen offers a cozy dinette, updated soft-close cabinetry, stainless steel appliances, recessed lighting, and tile countertops with backsplash. Down the hall are three bedrooms, all with lighted ceiling fans and new carpet. The primary ensuite boasts an updated bathroom with a walk-in shower and new hardware, while the guest bath offers resort-style features. Step through the back sliding glass door to a screened lanai with tile floors—perfect for relaxing or entertaining. The modest fenced backyard has fresh mulch and is easy to maintain. With a new A/C installed in 2022 and a prime location near trendy restaurants, shopping, AMC Woodlands Movies, and just minutes from Tampa, the airport, or the beach, this home truly has it all—don’t miss it! (house has never had any issues with flooding in 20 years owner has owned it)
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Shay Adelman (727-458-3702)
208 CUTLASS WAY, OLDSMAR, FL 34677
$350,00061 Days on yellowkey MLS ID: TB8501214
REDUCED by $20,000 (5.4%) on 04/29/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 2015Monthly Fee: $285 Tax: $3,417 (2025)Community: Hayes Park VillageSingle Family
Taxes:$3,417
Elementary School: Forest Lakes Elementary-PN
Remarks: 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 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.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Jennifer Kashtan (813-310-7200)
435 LAKEVIEW DR, OLDSMAR, FL 34677
$475,00090 Days on yellowkey MLS ID: TB8489554
REDUCED by $14,000 (2.9%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1570 Built: 1984Monthly Fee: $35 Tax: $6,675 (2025)Community: Manors Of Forest Lakes TheSpa: YesSingle Family
Taxes:$6,675
Remarks: Welcome to Forest Lakes and this beautifully appointed, immaculately maintained 3-bedroom, 2-bath, 2-car garage home offering 1,569 square feet of living space. Nestled in an exceptional school district, this home has been lovingly cared for and is truly immaculate. It features soaring vaulted ceilings, a cozy fireplace, and French doors leading to a large backyard retreat. The gorgeous kitchen with granite, newer stainless steel appliances, and pantry overlooks both the living room and the pool, which is fully screened and features a child-proof fence for added security. The master bedroom offers a private en-suite bath, providing a tranquil retreat. Other highlights for this house include a new 200 amp electrical panel with whole home surge protector, new switches and recepticals throughout and a dedicated 50 amp E.V. car charger. A four-year-old roof, with newer windows, and a new garage door, makes Florida living a breeze. Outside, enjoy the large pool area and spa with a new pump, timer, and automatic cleaner, a fire pit, and a host of amenities. An oversized garage also features a dedicated electric outlet for your vehicle, a washer and dryer, and a newer water heater. The community offers a lakefront playground, a barbecue area, a fishing dock, and courts for basketball, tennis, and racquetball. With very low monthly HOA fees and a large community pool, this move-in-ready home is a true gem. Don’t miss out! Nothing else to do but move in!
Listing is courtesy of: COLDWELL BANKER REALTY (727-581-9411)
Listing Agent: Kim Krenek (727-262-3181)
355 VENTURA DR, OLDSMAR, FL 34677
$625,00034 Days on yellowkey MLS ID: TB8510293
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1938 Built: 2001Monthly Fee: $100 Tax: $5,919 (2025)Community: Bay ArborSingle Family
Taxes:$5,919
Remarks: Virtually Staged. Welcome to this beautifully maintained and completely updated four-bedroom, two-bathroom home located in the gated community of Bay Arbor. Situated on a premium lot with tranquil pond views and no rear neighbors, this exceptional property is directly across the street from the community pool, offering both convenience and scenic surroundings. Thoughtfully renovated from floor to ceiling, this stunning residence blends modern upgrades with comfortable Florida living. Major updates, including a 2020 remodel featuring updated bathrooms, kitchen, Pergo laminate flooring throughout, and upgraded 5 ¼-inch baseboards. Additional enhancements include custom kitchen window seating added in 2020, USB outlets in the kitchen, exterior painting in 2020 with a 10-year warranty, gutters and patio birdcage added in 2020, a 2023 water softener, 2019 water heater, EV outlet, and extensive hurricane protection, including 2025 impact windows, front French door hurricane fabric protection, and a 2011 hurricane impact-rated rear patio French door. The roof was replaced in 2020 and includes a 50-year warranty. Step inside through the inviting foyer entry and immediately notice the high ceilings, abundant natural light, and stylish wood-look flooring flowing throughout the home. The spacious kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances, a beverage fridge, extensive cabinetry for storage, Corian countertops, and a cozy breakfast nook with built-in bench seating. The kitchen opens seamlessly to the dining area and expansive living room highlighted by vaulted ceilings and an open, airy feel. The oversized primary suite offers a relaxing retreat with a large walk-in closet and a beautifully updated private bathroom complete with a dual-sink vanity, soaking tub, glass-enclosed shower, updated fixtures, and private water closet. The additional bedrooms are all generously sized and equipped with ceiling fans for added comfort. Enjoy Florida living year-round from the large screened-in lanai overlooking the fenced backyard and peaceful pond views. Residents of Bay Arbor enjoy access to a community pool and a prime location close to popular dining spots, shopping centers, golf courses, parks, movie theaters, and outdoor recreation. Conveniently situated near Tampa International Airport, Mobbly Bayou Beach Park, Honeymoon Island State Park, Upper Tampa Bay Park Nature Center, AMC Woodlands Square 20, and Tampa Bay Downs, this home offers the perfect blend of privacy, convenience, and lifestyle. Schedule your showing today!
Listing is courtesy of: EXP REALTY LLC (866-308-7109)
Listing Agent: Robert Paolini (727-365-8335)
848 CHRISTINA CIR, OLDSMAR, FL 34677
$560,00039 Days on yellowkey MLS ID: TB8509369
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1756 Built: 1994Monthly Fee: $68 Tax: $4,544 (2025)Community: Bay's EndSpa: YesSingle Family
Taxes:$4,544
Remarks: Tucked away in the desirable enclave of Bay’s End, this stunning contemporary two-story residence blends upscale coastal living with exceptional indoor-outdoor entertaining. From the moment you enter, soaring ceilings, an open-concept design, and abundant natural light create a warm yet sophisticated atmosphere. Rich wood-look luxury vinyl flooring flows seamlessly throughout the home, enhancing its modern coastal appeal. At the heart of the home is a beautifully designed island kitchen featuring elegant wood cabinetry, gleaming quartz countertops, and stainless steel appliances. The kitchen opens effortlessly to the spacious living and dining areas, highlighted by a striking wood-burning fireplace and views of the tropical pool and spa retreat. The main-level owner’s suite is a private sanctuary complete with a walk-in closet and an expansive spa-inspired bathroom filled with natural light, featuring a luxurious vanity, soaking tub with shower. A convenient half bath, interior laundry room, and attached two-car garage complete the first floor. Upstairs, you’ll find two additional bedrooms, a full bath, and a versatile den/media room perfect for a home office, playroom, or entertainment space. Step outside through sliding glass doors to your own private resort-style oasis. The screened lanai surrounds an entertaining-sized pool with waterfall and spa, framed by towering palm trees and lush tropical landscaping. By night, the spectacular pool and landscape lighting transform the backyard into a truly magical setting. Situated on nearly a quarter-acre, the enormous privacy-fenced backyard offers endless possibilities — currently serving as the ultimate playground for soccer, baseball, basketball, and golf. Exceptional savings with the solar panels, installed in 2020. Seller will pay the financing in full at closing. This exceptional Bay’s End home combines style, comfort, and resort-inspired living in one unforgettable package. Opportunities like this don’t last long.
Listing is courtesy of: RIZZO & ASSOCIATES INC (727-894-4400)
Listing Agent: Philip Rizzo (727-656-4400)
50 WILLOWOOD LN, OLDSMAR, FL 34677
$1,499,900131 Days on yellowkey MLS ID: TB8475420
Bed: 5 Bath: 4.5 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
Remarks: **4 Bedrooms + Office + Flex Room (Potential 6th Bedroom) | Private Entrance to Flex Space | 4.5 Baths | Massive Upstairs Loft | Wet Bar in Family Room | Nearly 2,000 SF Screened Pool & Lanai Area | Full Pool Bath | Gated East Lake Woodlands Community | Minutes to Beaches, Airports, Shopping & Dining** Rarely does a home offer this level of space, flexibility, and privacy in Deerpath, in the highly sought-after East Lake Woodlands community. Tucked away on 1.4 acres a quiet cul-de-sac with no rear neighbors within this gated neighborhood, 50 Willowood Lane presents an exceptional opportunity for buyers seeking a versatile floor plan that can adapt to virtually any lifestyle. With 4 true bedrooms, a dedicated office, and an additional flex room with a private entrance, this home comfortably lives as a 4-, 5-, or even 6-bedroom residence. Whether you need a home office, guest suite, in-law accommodations, gym, playroom, or multi-generational living space, the possibilities are endless. Upstairs, two bedrooms share a Jack-and-Jill bath and are complemented by an expansive loft—perfect for a media room, study area, game room, or secondary family room. The spacious, light-filled interior offers an open-concept layout designed for both everyday living and entertaining. Generous living and dining spaces flow seamlessly into the well-appointed kitchen, featuring abundant cabinetry, ample workspace, and an ideal setup for gathering with family and friends. The primary suite serves as a private retreat with an en-suite bath and generous closet space, while the home's thoughtful layout provides comfort and privacy throughout. Outdoor living is equally impressive, with nearly 2,000 square feet of screened pool and lounge space creating a true backyard oasis. The pool is refinished as is the pool decking with gorgeous herringbone travertine to match the herringbone Turkish tile floors throughout the main level. Complete with a full pool bath, this expansive area is ideal for entertaining, relaxing, and enjoying Florida's year-round sunshine. Located within the desirable East Lake Woodlands community, residents enjoy optional access to golf, tennis, fitness, and country club amenities while remaining conveniently close to top-rated schools, Tampa International Airport, shopping, dining, and the Gulf Coast's award-winning beaches. A rare combination of size, flexibility, and location in one of Oldsmar's most desirable gated communities! Call or text to schedule a private tour.
Listing Agent: Melissa Pranzo (646-509-7350)
3071 HURON AVE, OLDSMAR, FL 34677
$469,90038 Days on yellowkey MLS ID: TB8507555
REDUCED by $30,000 (6.0%) on 06/18/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1680 Built: 1987 Tax: $5,919 (2025)Community: West Oldsmar Sec 1Single Family
Remarks: Must see this amazing home in one of Oldsmar's best kept secret neighborhoods on the sparkling shores of Old Tampa Bay! This 3-bedroom, 2.5-bath multi-level designed home has been FULLY RENOVATED with real class blending coastal charm with PRISTINE UPDATES in every room. Above the Oversized 2-car garage, get ready to be impressed by the high ceilings, all NEW WINDOWS, DOORS & light filled living spaces amongst the refinished oak hardwood & gorgeous porcelain ceramic tile flooring throughout. NEW ROOF 2024! STAIRS & DECKS REFURBISHED! The STUNNING KITCHEN has QUARTZ countertops & stainless steel appliances opening into the living and grand dining rooms with french doors onto the enormous covered deck. It's perfect for entertaining and family time. Upstairs you find 3 good sized bedrooms and 2 full bathrooms. The primary suite features french doors to its own private balcony along with a spa inspired ensuite bathroom featuring a luxurious freestanding tub & separate shower that feels straight from a boutique retreat. Not only is this home perfect for all your year round outdoor activities, you can even cozy up by the wood burning fireplace during cold times. The 2 car garage offers exceptional storage space for all the extras, while the oversized back yard opens the door to endless possibilities to make it your new tropical paradise with room for a pool, gardens, boat or RV parking, and even a potential in-law suite. Just minutes from several Waterfront Parks (R.E. Olds Park is biking distance), Scenic trails, Boat ramps, Fishing, Tennis, Pickle ball, Golfing, Tampa Bay Downs, Shopping, Restaurants, and Top Rated Schools in this location, you truly have it all! Possible owner financing available.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Diana Beattie (727-417-7021)
50 KELLEYS TRL, OLDSMAR, FL 34677
$949,00049 Days on yellowkey MLS ID: TB8504781
REDUCED by $50,000 (5.0%) on 06/18/2026
Bed: 4 Bath: 4.0 Gar: 3 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)
442 EVERGREEN DR, OLDSMAR, FL 34677
$355,0008 Days on yellowkey MLS ID: TB8517079
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1190 Built: 1979 Tax: $5,386 (2025)Community: Harbor Palms Unit Eleven Lot 451Single Family
Taxes:$5,386
Remarks: Welcome to 442 Evergreen Drive, perfectly situated in one of Oldsmar's most desirable neighborhoods! This beautifully maintained residence offers the ideal combination of comfort, style, and Florida charm. Filled with abundant natural light, the spacious interior features a thoughtfully designed floor plan that seamlessly blends everyday living with effortless entertaining. Step outside and discover your own private backyard retreat, complete with a screened-in porch that provides the perfect setting for morning coffee, weekend gatherings, or simply unwinding after a long day. Freshly painted inside and out, this move-in-ready home showcases pride of ownership throughout and provides a fresh, inviting atmosphere from the moment you enter. Enjoy peace of mind knowing many of the home's major components have already been updated, including a Roof (2018), HVAC System (2018), Windows & Doors (2021), and Garage Door (2018). Conveniently located near beautiful parks, top-rated dining, shopping, entertainment, and the stunning Gulf beaches, this exceptional property offers the best of the Florida lifestyle. Whether you're looking for your first home, a growing family residence, or a place to enjoy your next chapter, 442 Evergreen Drive is ready to welcome you home. Showcasing exceptional maintenance, valuable updates, and a desirable screened-in porch for year-round enjoyment, this wonderful property offers a rare opportunity to enjoy comfortable Florida living in a prime Oldsmar location.
Listing Agent: Sheri Boesch (727-776-3422)
1811 DRIFTWOOD CIR S, OLDSMAR, FL 34677
$359,90096 Days on yellowkey MLS ID: TB8488580
REDUCED by $10,100 (2.7%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1248 Built: 1973 Tax: $1,036 (2025)Community: Harbor Palms-Unit TwoSingle Family
Taxes:$1,036
Remarks: Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of Oldsmar! Offering 1,248 sq ft of well-designed living space, this move-in-ready property features a functional layout, abundant natural light, and modern updates throughout. Enjoy spacious living and dining areas that flow seamlessly, perfect for both everyday living and entertaining. The kitchen offers ample cabinetry and workspace, while the bedrooms are generously sized for comfort and flexibility. Conveniently located near parks, shopping, dining, and major roadways, this home provides easy access to Tampa, Clearwater, and surrounding areas. Don’t miss this opportunity to own a well-maintained home in a desirable location!
Listing Agent: Julio Vasquez (727-404-8889)
316 COUNTRY CLUB DR, OLDSMAR, FL 34677
$325,00040 Days on yellowkey MLS ID: TB8508856
REDUCED by $3,900 (1.2%) on 06/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1344 Built: 1960 Tax: $616 (2025)Community: Oldsmar Country Club Estates Sec 3Single Family
Taxes:$616
Remarks: Yes! This beautifully renovated mid-century modern block home actually looks this good in person - no AI staging here! Located in the desirable NO HOA community of Oldsmar Country Club Estates. Timeless character with modern upgrades are inside this 3 bedrooms, 2 bathrooms. Under the exposed beams is 1,344 square feet of thoughtfully updated living space. The fully renovated kitchen features elegant quartz countertops, 42” upper cabinets, and stainless steel appliances, creating a stylish and functional space for everyday living and entertaining. Don't let the floor to ceiling windows fool you eco-friendly design allows a low-cost energy bill. Additional highlights and upgrades include: newer vinyl windows, a 2017 roof, 2023 ductless mini-split system, 2023 hot water heater, and updated electrical in 2025 for added peace of mind. Step outside to enjoy the fully fenced backyard, perfect for pets, entertaining, or relaxing in privacy. The attached carport provides convenient covered parking and additional storage flexibility. Ideally situated just yards from the Oldsmar Boat Ramp with direct access to Tampa Bay, this golf cart-friendly community offers the perfect Florida lifestyle. R.E. Olds Park is a 15-acre dog- friendly waterfront park featuring a 400 -foot fishing pier, playgrounds, picnic shelters, an amphitheater, and trails with scenic views of Tampa Bay. Named after automotive pioneer Ransom E. Olds, the park hosts numerous community events and offers amenities like volleyball, tennis & pickleball courts & restrooms. With no HOA restrictions, park the boats, RV’s and work trucks with ease. This property is ideal for a first-time homebuyer, seasonal resident, or as an income-producing short-term rental investment opportunity. Annual Flood quote $2,653.34
Listing is courtesy of: TMWRK BROKERAGE LLC (727-277-9032)
Listing Agent: Faith Walston (813-303-1239)
2151 DIAMOND CT, OLDSMAR, FL 34677
$1,350,000240 Days on yellowkey MLS ID: TB8440175
0 Days Off yellowkey (back on 6/16/2026)
REDUCED by $39,000 (2.8%) on 04/21/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3850 Built: 1998Monthly Fee: $142 Tax: $9,378 (2024)Community: Diamond CrestSpa: YesSingle Family
Taxes:$9,378
Remarks: Under contract-accepting backup offers. Welcome to 2151 Diamond Court ~ Where luxury meets everyday comfort and style. This beautifully updated residence in the exclusive, gated community of Diamond Crest at East Lake Woodlands offers stunning water and conservation views and a thoughtfully designed 3-way split floor plan with a dedicated front office. From the moment you step inside, you’ll notice the meticulous attention to detail. The spacious, NEWLY RENOVATED GOURMET KITCHEN features custom cabinetry, quartz countertops, Café Platinum Collection appliances (including double wall ovens with air fryer and 36” induction cook-top), and a show-stopping triple frosted glass pantry door. The kitchen opens seamlessly to the expansive great room where a 60”, three-sided glass linear fireplace and floor-to-ceiling picture window frame the serene natural backdrop. Nearly every major improvement has already been completed for peace of mind — including a BRAND NEW TILE ROOF, PGT LOW-E IMPACT WINDOWS, luxury plank flooring throughout, and a NEW PANORAMIC-VIEW SCREENED LANAI enclosure that beautifully extends your indoor living outdoors. Enjoy unobstructed views of lush conservation and tranquil water, making this home perfect for both relaxing and entertaining. The primary suite is generously sized with large windows that bring the outdoors in, while each guest wing offers privacy and comfort. All bathrooms have been tastefully remodeled, and remote-operated window treatments and ceiling fans add to the home’s thoughtful conveniences. Outside your front door, discover the newly re-imagined Ardea Country Club, offering championship golf, state-of-the-art racquet facilities, expanded dining, resort-style amenities, and engaging spaces for all ages. Membership is optional — simply visit the clubhouse for details. Location is unbeatable — tucked in a quiet, private setting yet just 20–25 minutes to Tampa International Airport, award-winning Gulf beaches, and the vibrant dining and shopping of both Tampa and Clearwater. This home truly has it all — luxury, convenience, and a view you’ll never tire of. Come experience it in person.
Listing is courtesy of: RE/MAX ELITE REALTY (727-785-7653)
Listing Agent: Michelle Johncola (727-515-2415)
364 VENTURA DR, OLDSMAR, FL 34677
$599,90014 Days on yellowkey MLS ID: TB8517197
1 Days Off yellowkey (back on 6/16/2026)
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2237 Built: 2001Monthly Fee: $100 Tax: $9,325 (2025)Community: Bay ArborSingle Family
Taxes:$9,325
Remarks: Under contract-accepting backup offers. Tucked behind the gates of Bay Arbor, 364 Ventura Drive stands out from the moment you arrive with turret-style architecture, arched windows, a paver entry, and a 3-car garage that give this home a level of character and curb appeal that feels different from the typical Florida two-story. Inside, soaring cathedral and vaulted ceilings create an open, airy feel with natural light carrying through both levels, while the main living areas offer flexible spaces divided by a fireplace, giving you room for a formal dining area, sitting room, home office, or whatever best fits your lifestyle. The kitchen opens to the main living area, keeping the layout connected and practical for everyday living, entertaining, and everything in between. Upstairs, all three bedrooms are tucked away from the main living spaces, along with a second-floor loft/den that adds even more flexibility for a reading nook, desk space, play area, or quiet retreat. The spacious primary suite includes a walk-in closet and private en-suite bath, and with 2,218 square feet, the home offers a layout that feels intentional, functional, and easy to live in. Out back, the covered patio and deck overlook a peaceful conservation area with mature trees and no rear neighbors, creating a setting that feels private and relaxing. Major systems have also been thoughtfully updated, including a 2024 AC condenser, 2022 air handler, 2025 water heater, and 2016 roof. Located one home away from the community pool and playground, in Flood Zone X, and with convenient access to shopping, dining, Tampa International Airport, and the Gulf beaches, this home offers presence, privacy, and a location that keeps you close to everything Tampa Bay has to offer.
Listing is courtesy of: TREASURED HOME COLLECTION (727-210-3282)
Listing Agent: Angel Bueno (727-437-6583)
10 ARBOR LN, OLDSMAR, FL 34677
$669,00019 Days on yellowkey MLS ID: TB8516041
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2318 Built: 1979Monthly Fee: $148 Tax: $9,038 (2025)Community: East Lake WoodlandsSpa: YesSingle Family
Taxes:$9,038
Remarks: Beautiful 4-bedroom, 2-bathroom pool home on a corner lot with views of the 5th hole in East Lake Woodlands. Offering a desirable split-bedroom floor plan, open living areas, and a screened pool and spa, this home combines comfort, functionality, and an exceptional golf course setting. Inside, you'll find a spacious split-bedroom floor plan featuring vaulted ceilings, exposed wood beams, and an open layout designed for both everyday living and entertaining. The inviting living room centers around a cozy fireplace, creating a warm gathering space for family and friends. The kitchen offers abundant teak wood cabinetry with convenient pull-out drawers, stainless steel appliances, a breakfast nook, and thoughtful updates that enhance both style and functionality. The outdoor living area is truly exceptional. A screened-in pool and spa overlook the golf course, while multiple seating and dining areas provide the perfect setting for entertaining guests or enjoying peaceful evenings outdoors. This home has been extensively updated and meticulously cared for. Major improvements include a new roof and gutters in 2022, a new HVAC system in 2025, exterior paint, updated exterior lighting, wired landscape lighting, removal of popcorn ceilings, replacement of eaves with anti-rot wood, and the addition of a skylight. The pool and spa systems have also been upgraded with a new pool filter, pool pump, pool sweep, pool equipment, propane tanks, and a new heater and pump for the spa. Interior enhancements include lifting and leveling the living room floor, installation of waterproof flooring in the living room and laundry room, a new kitchen sink and faucet, updated kitchen electrical, new garbage disposal, dishwasher, refrigerator, laundry room utility tub, and multiple lighting improvements throughout the home. Comfort has been enhanced with six new interior ceiling fans and remote-controlled lanai fans. The primary suite features a beautifully updated bathroom with new cabinetry, countertops, sinks, mirrors, faucet, toilet, lighting, and custom blinds. The guest bathroom has also been refreshed with updated lighting and a new toilet. Additional upgrades throughout the home include new blinds, new door knobs and locks, an outlet for a built-in beverage refrigerator, a new dining room chandelier, and a custom banquette in the kitchen. With its golf course setting, extensive upgrades, resort-style outdoor living, and prime location within East Lake Woodlands, this home offers a rare opportunity to enjoy Florida living at its finest. East Lake Woodlands is a deed-restricted, gated community offering exceptional amenities including golf, pickleball, tennis courts, a community pool, and a clubhouse. Ideally located, this home is approximately 25 minutes from Tampa International Airport, 20 minutes from St. Pete-Clearwater International Airport, 30 minutes from Clearwater Beach, and 35 minutes from Honeymoon Island. Enjoy easy access to a variety of nearby restaurants, shopping, and everyday conveniences. Don’t miss your opportunity to own this exceptional home—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Julio Morales (813-507-5191)
313 JEFFERSON AVE S, OLDSMAR, FL 34677
$415,00056 Days on yellowkey MLS ID: TB8502786
REDUCED by $15,000 (3.5%) on 06/15/2026
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: 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)
165 MOBBLY BAY DR, OLDSMAR, FL 34677
$1,124,900273 Days on yellowkey MLS ID: TB8430614
REDUCED by $25,000 (2.2%) on 06/15/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3945 Built: 2012Monthly Fee: $183 Tax: $8,887 (2024)Community: Estuary Of Mobbly BaySpa: YesSingle Family
Taxes:$8,887
Remarks: Wow!! Picture perfect model home located in the exclusive gated community of ‘Estuary of Mobbly Bay’. This home boasts 5 large bedrooms, plus a den/office, plus an upstairs bonus room, 4 full baths and a 3-car garage... Nearly 4,000 sq.ft. of grandeur! The moment you walk through the commanding solid wood front door you are greeted to excellence!!! A true “family home” with separate formal living and dining areas. The kitchen and family room are perfectly positioned as an entertainer’s dream! The kitchen includes a cook top, wall oven/microwave, granite counters and a designer tile back splash. The desirable double island layout allows for a substantial breakfast bar in addition to an eat-in area. And this wide-open space overlooks the huge family room accented by magnificent French doors and views of a beautiful outdoor living space! Of course, the splendor extends outside!! There is a large pavered lanai & beautifully designed pool, with a ‘sun shelf’ and raised hot tub!! The remainder of the main living level claims 4 of the 5 bedrooms. All generously sized with large windows revealing a light & bright setting. The primary retreat is fit for royalty and has upgrades galore! Crown molding, ensuite w center set soaking tub and a massive double-entry ‘walk in’ shower! All bathrooms are elegantly designed and completed with striking finishes! A bonus living space and the 5th bedroom with an additional full bath are found upstairs. Absolutely perfect for a nanny or in-law quarters or a fitting design for a large family! Infinite upgrades! Pride of ownership and exquisite taste prevail in this stunning home near to shopping, restaurants, Tampa International Airport and the famed Gulf beaches!! This one has it all! A true must see!!
Listing Agent: Nancy Leslie (727-789-5555)
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