Location: Oldsmar
Do Not Show Listings
307 COUNTRY CLUB DR, OLDSMAR, FL 34677
$399,9002 Days on yellowkey MLS ID: TB8502335
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1670 Built: 1960 Tax: $3,567 (2025)Community: Oldsmar Country Club Estates Sec 3Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,567
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
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)
2272 WARWICK DR, OLDSMAR, FL 34677
$725,0002 Days on yellowkey MLS ID: TB8502055
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2512 Built: 1995Monthly Fee: $133 Tax: $3,084 (2025)Community: Warwick HillsSpa: NoSingle Family
Taxes:$3,084
Elementary School: Cypress Woods Elementary-PN
Remarks: Welcome to 2272 Warwick Drive—where timeless elegance meets effortless Florida living. This well-maintained one-story home offers four spacious bedrooms, three full baths, a sparkling screened-in pool and a three-car garage. From the moment you arrive, stately columns and a grand double-door entry set the tone for what’s inside—soaring volume ceilings and an open, light-filled layout designed for both comfortable living and stylish entertaining. The living room is a true focal point, featuring a custom-built wall unit that adds both character and functionality. Peace of mind comes easy with a long list of recent updates, including a new HVAC system, water heater, and pool pump (2025), plus a resurfaced pool (2022) and new pool screens (2024). The beautifully updated eat-in kitchen is the heart of the home, featuring attractive maple cabinetry, granite countertops, a large center island and white appliances—including a new refrigerator (2026) and microwave (2025). Retreat to the oversized primary suite with its own sitting area—your private sanctuary—complete with a remodeled bath showcasing granite counters and refreshed cabinetry. Step outside and unwind in your private backyard oasis, where the pavered patio and screened pool overlooks the berm with no rear neighbors. Located in the exclusive Warwick Hills enclave within East Lake Woodlands, a 24/7 gated, resort-style community spanning 2,200 acres. Membership options available at the newly renovated Ardea Country Club. Indulge in championship golf, premier racquet facilities, a resort-style pool, fitness center, dining, and more. All of this, plus top-rated A schools and an unbeatable Oldsmar location just minutes to shopping, dining, parks, the Pinellas Trail, and Tampa International Airport—makes this home truly exceptional.
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Marcy Daniels (727-560-8080)
2151 DIAMOND CT, OLDSMAR, FL 34677
$1,350,000185 Days on yellowkey MLS ID: TB8440175
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
Tax Year: 2024
Remarks: 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)
1806 FOREST DR, OLDSMAR, FL 34677
$418,000182 Days on yellowkey MLS ID: TB8442794
1 Days Off yellowkey (back on 4/30/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1539 Built: 1973 Tax: $4,086 (2024)Community: Harbor PalmsSingle Family
Taxes:$4,086
Remarks: Under contract-accepting backup offers. Welcome to this beautifully remodeled home filled with natural light and modern charm. The open-concept floor plan features a spacious living area with brand new windows throughout the house, the new designed kitchen offers new cabinetry beautiful countertops, new stainless-steel appliances, and a breakfast bar the flows seamlessly into the dining and living spaces, interior laundry room with new cabinets and new washer & dryer. New central air condition and ductwork, new ceiling lights and fans, new flooring throughout the house. The primary bedroom includes a large closet and a stylish new bathroom with a glass - enclosed shower-tub combo, modern finishes. Two additional bedrooms provide versatility for guess, a home office, and the second new full bath is bright and modern. All interior doors are new so it is the front door and garage door, new interior and exterior paint, new wood fence, new landscape. this home is a perfect blend of comfort and value.
Listing Agent: Mena Reyes (727-789-5555)
507 SHORE DR E, OLDSMAR, FL 34677
$239,00042 Days on yellowkey MLS ID: TB8488465
2 Days Off yellowkey (back on 4/2/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1237 Built: 1972 Tax: $1,158 (2025)Community: Tampashores Bay SecSingle Family
Taxes:$1,158
Remarks: Under contract-accepting backup offers. Don’t miss this exceptional opportunity to build your dream home on a spacious homesite with beautiful views of Tampa Bay. Situated on a generous, nearly 1/3-acre lot measuring approximately 75 x 175, this property is being offered at land value—perfect for new construction. Located on a street experiencing exciting growth, with several newly built homes already completed and more underway, this is an ideal setting for your custom residence. The community offers an outstanding lifestyle with amenities including parks, playgrounds, a fishing pier, and a dog park. The property is also zoned for A-rated schools, adding to its long-term value and appeal. Conveniently located with easy access to Tampa International Airport, as well as a variety of restaurants, shopping, and entertainment options. Plus, you’re just a short drive from some of America’s most renowned beaches. Whether you’re a builder, investor, or future homeowner, this is a rare chance to secure a premium lot in a desirable waterfront area.
Listing is courtesy of: ENGEL & VOLKERS BELLEAIR (727-461-1000)
Listing Agent: Chris Stivers (727-542-5729)
382 ROSALIND LN, OLDSMAR, FL 34677
$822,000285 Days on yellowkey MLS ID: TB8408993
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3273 Built: 2001Monthly Fee: $100 Tax: $8,003 (2024)Community: Bay ArborSpa: YesSingle Family
Taxes:$8,003
Elementary School: Forest Lakes Elementary-PN
Remarks: NEW YEAR; NEW PRICE! Welcome to 382 Rosalind Ln., an extraordinary home in the exclusive gated community of Bay Arbor in Oldsmar. This thoughtfully upgraded and impeccably maintained residence offers over 4,000 square feet of elegant living space, combining luxury, privacy, and smart-home functionality. Situated on a quiet cul-de-sac and backed by a peaceful conservation lot, the home features soaring ceilings, abundant natural light, Italian marble-look tile, a formal living and dining room, a spacious office, and a beautifully updated full bath. The open-concept main living area opens to a stunning screened-in patio with a heated spa, pool, waterfall, and wooded views — ideal for relaxation and entertaining. The chef’s kitchen boasts cherry cabinetry, granite countertops, stainless steel appliances, purified water, wine storage, a breakfast bar, and an eat-in nook. Upstairs you'll find four spacious bedrooms and a soundproofed 18' x 20' media room, easily converted into a second primary suite or flex space. The luxurious primary suite includes two walk-in closets, a spa-style bathroom with soaking tub and walk-in shower. The fully fenced backyard oasis includes a new outdoor luxury kitchen, pet turf, and smart-controlled pool and spa with a waterfall and fountain feature. Additional upgrades include new pool equipment, attic insulation, UV air purification, custom shutters, new water heater, full security system, vinyl fencing, lightning and surge protection, new AC unit upstairs, and more. Just 20 minutes from Tampa International Airport and close to top beaches, this rare gem delivers the ultimate in Florida luxury living.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Stephanie Eisenbach (813-468-0230)
1802 CHINABERRY DR, OLDSMAR, FL 34677
$375,000192 Days on yellowkey MLS ID: TB8439498
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
Elementary School: None
High School: None
Middle School: None
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)
470 HICKORYNUT AVE, OLDSMAR, FL 34677
$795,00050 Days on yellowkey MLS ID: TB8485715
REDUCED by $20,000 (2.5%) on 04/02/2026
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)
105 KILSYTHE ST, OLDSMAR, FL 34677
$305,000Listed 04/30/2026 7:18AM MLS ID: TB8502588
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1036 Built: 1981 Tax: $4,256 (2025)Community: Shoreview Ph ISingle Family
Taxes:$4,256
Remarks: One or more photo(s) has been virtually staged. HIGH & DRY with no storm damage and NO HOA—this beautifully updated 3-bedroom, 2-bath Oldsmar gem delivers exceptional value, peace of mind and an unbeatable Florida lifestyle. Featuring an open great room plan ideal for entertaining, this move-in ready home showcases fresh interior and exterior paint, an updated kitchen with newer cabinetry, granite counters and designer backsplash, renovated baths, 2024 roof, newer windows, spacious screened lanai, fenced backyard and oversized storage shed. Live where others vacation—walk, bike or take your golf cart to nearby waterfront parks, fishing pier, pickleball, boat launch access to Tampa Bay, scenic trails, playgrounds and community events including Mobbly Bayou Wilderness Preserve, R.E. Olds Park, Veterans Memorial Park, Bicentennial Park and the Upper Tampa Bay Trail. Just minutes to charming downtown Safety Harbor (8 minutes) and Dunedin (15 minutes) for dining, festivals and waterfront charm, approximately 20 minutes to Tampa International Airport and 25–30 minutes to world-famous Clearwater Beach (25 minutes). Rare opportunity to own a fully updated home in one of Oldsmar’s most established and sought-after neighborhoods where convenience, recreation and coastal living meet—hard to find this level of updates, lifestyle and value in one package.
Listing is courtesy of: FLORIDA EXECUTIVE REALTY (813-908-8500)
Listing Agent: Dave Maks (813-679-3445)
313 JEFFERSON AVE S, OLDSMAR, FL 34677
$450,0001 Day on yellowkey MLS ID: TB8502786
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 includes a spacious living area filled with natural light, a charming front porch, and an upstairs additional room that can function well as a home office, playroom, guest area, or other flexible living space. 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. Roof is brand new HVAC recently fully refurbished Property has a covered front porch. Clean 4-point, wind mit report, WDO report, and recent appraisal in hand. (Value came back at $475k) Bonus room up stairs (loft/playroom or kids room). Was NOT considered in the 3bed total bedroom count.
Listing is courtesy of: GRAYSTONE REAL ESTATE (727-201-4011)
Listing Agent: Bradley Dreher (863-346-0500)
395 WINGATE CIR, OLDSMAR, FL 34677
$575,000161 Days on yellowkey MLS ID: TB8450027
REDUCED by $15,000 (2.5%) on 04/29/2026
Bed: 5 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2827 Built: 2001Monthly Fee: $100 Tax: $9,963 (2025)Community: Bay ArborSingle Family
Taxes:$9,963
Remarks: Lowest Listed Price Per Square Foot for this community. Picture Perfect Bay Arbor, a gated community. (Approved plans to extend fence in backyard) The School District zoned for this home has two A and one B+ rated schools and zoned for Palm Harbor University IB program. Just a mile walk or golf card ride through the community to just outside the gates brings you to the local First Watch, Beef O' Bradys, Aveda, Tijuanna Flats, and Hot Tuna Sushi. The communities natural surroundings, abundant with community green-space, wildlife, and a community Pool & Playground. A 3 car garage, paver driveway & paver path to the front porch greets you out front. The foyer immediately opens up to high ceilings, filled with natural light. The laundry room and the flex room/5th bedroom, media room, office, and/or den are available on the first level. A Breakfast Bar, generous amounts of counter space, and stainless steel appliances for the kitchen. The Breakfast Nook has a large pantry space and overlooks the fenced backyard. The Primary Bedroom and Bedrooms 2-4 are an easy trip up with the two-side staircase. The Primary Bedroom fits a King Size Bed, 2 Walk-in Closets, Glass shower, Garden Tub, and Dual Vanities. You will appreciate the 240sq.ft. rear screened patio leading to your shady, vinyl fenced yard. Your peace of mind knowing the Roof was installed in 2022 and the dual zone A/C system is 2018 and 2012. Convenient to the Tampa airport, Mobbly Bayou Beach Park, Honeymoon Island, UTBP Nature Center, AMC Woodlands Square 20, Tampa Bay Downs. Come enjoy the true Florida Lifestyle!
Listing is courtesy of: STOFEL & ASSOCIATES REALTY (727-350-0373)
Listing Agent: Joey Torres (727-415-7017)
509 CYPRESS VIEW DR, OLDSMAR, FL 34677
$634,00012 Days on yellowkey MLS ID: TB8496854
REDUCED by $15,000 (2.3%) on 04/27/2026
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 ... 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)
208 CUTLASS WAY, OLDSMAR, FL 34677
$350,0006 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
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)
103 CUTLASS WAY, OLDSMAR, FL 34677
$345,00066 Days on yellowkey MLS ID: TB8479354
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 2016Monthly Fee: $255 Tax: $6,017 (2025)Community: Hayes Park VillageSingle Family
Taxes:$6,017
Remarks: Welcome to this impeccably maintained 3 bedroom, 2.5 bath residence in the highly sought-after Hayes Park Village in Oldsmar. Offering approximately 1,392 square feet of thoughtfully designed living space, this home showcases a beautifully renovated kitchen with contemporary finishes, ceramic flooring on the first floor, and carpet flooring on the second floor. The split-bedroom floor plan and abundant natural light create a bright, open atmosphere that is both welcoming and functional. Step outside to a covered porch overlooking a breathtaking pond and a serene conservation area behind it —providing exceptional privacy. Combining generous living space, peaceful privacy, and an unbeatable location, this exceptional home is ready to welcome YOU!
Listing is courtesy of: FLORIDA COMMERCIAL GROUP (813-935-9600)
Listing Agent: Leyla Mohebbi (813-359-7999)
316 COUNTRY CLUB DR, OLDSMAR, FL 34677
$329,00078 Days on yellowkey MLS ID: TB8475078
REDUCED by $10,000 (2.9%) on 04/15/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1344 Built: 1960 Tax: $562 (2025)Community: Oldsmar Country Club Estates Sec 3Single Family
Taxes:$562
Remarks: Yes! These are the real pictures of what this home REALLY looks like! No virtual staging here - these photos are of the REAL DEAL found inside this move-in ready, renovated mid-century modern home located in the heart of Oldsmar. Stop searching and start packing because this rare architectural gem is PRICED UNDER APPRAISAL. Why pay waterfront prices, when this home sits yards away from boat ramp access to Moobly Bay & Safety Harbor. With NO HOA, park your toys with ease - boats, RVs, trailers, golf carts and work trucks. Opportunities to own a move-in ready Mid-Century Modern masterpiece rarely arise. This is your chance to secure instant equity in this 3 bedroom, 2 bathroom property that seamlessly blends iconic design with today's high-end, low-maintenance lifestyle. This residence is a masterclass in quintessential mid-century style, defined by soaring exposed beams, expansive windows that flood the home with natural light, and terrazzo flooring. The split-floor plan offers three spacious bedrooms and two stylishly updated bathrooms. Bedrooms are large enough to fit two full-size beds, with plenty of room to walk-around. Stylish updated bathrooms bring the color of the outdoors into this modern design. At the heart of the home, the recently renovated kitchen features sleek modern finishes, 42-inch upper cabinets, quartz countertops, stainless steel appliances, and high-end cabinetry, making it as functional as it is beautiful. The potential for forced appreciation here is unmatched. A massive, versatile bonus room provides the perfect footprint for a dedicated home office, secondary living area, or quick conversion into an attached apartment or mother-in-law suite for multi-generational living or rental income. Furthermore, the expansive carport offers a ready-made foundation to create a fourth bedroom or enclosed family room, potentially adding over 400 square feet of air conditioned living space to your investment. Outside, the fully fenced backyard serves as a private oasis for entertaining or pets. All major systems have been updated, providing complete peace of mind. This property has also performed well as a short-term rental, making it an ideal choice for savvy investors or snowbirds seeking flexible income. The lifestyle offered here is second to none, located just yards from the Oldsmar Boat Ramp with direct access to Tampa Bay for world-class fishing and water sports. Enjoy a bike-friendly community with rapid access to RE Olds Park, the Oldsmar Trail, and the historic horse track. You are steps away from pickleball, tennis, and the vibrant events that make this neighborhood one of the most beloved in the region. This is a rare opportunity to own architectural history with significant modern updates WITHOUT the premium waterfront price tag. Because this home is priced to move immediately, it will not last. Schedule your private showing today before this below-appraisal deal disappears. Bring your offers!
Listing is courtesy of: SELLSTATE COASTAL REALTY (813-940-0101)
Listing Agent: Faith Walston (813-303-1239)
1820 DRIFTWOOD CIR N, OLDSMAR, FL 34677
$379,900164 Days on yellowkey MLS ID: TB8447176
0 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1528 Built: 1973 Tax: $1,160 (2024)Community: Harbor Palms-Unit TwoSpa: NoSingle Family
Taxes:$1,160
Remarks: Under contract-accepting backup offers. GREAT BUY ON THIS WONDERFUL 3 BEDROOM POOL HOME LOCATED IN THE DESIRABLE HARBOR PALMS SUBDIVISION. THE HOME FEATURES AN EXCELLENT SPLIT-BEDROOM FLOOR PLAN, A SPACIOUS LIVING ROOM, A COMFORTABLE FAMILY ROOM, AND GENEROUSLY SIZED BEDROOMS. ENJOY A SCREENED-IN POOL AND AN OVERSIZED ONE-CAR GARAGE. RECENT UPDATES INCLUDE A NEW A/C (2022), NEW ELECTRICAL PANEL (2023), AND A ROOF INSTALLED IN 2012. WITH INTERIOR UPDATES, THIS ADORABLE, COZY HOME CAN BECOME EXACTLY WHAT YOU’RE LOOKING FOR. NO FLOOD DAMAGE FROM RECENT STORMS. GREAT OLDSMAR LOCATION CLOSE TO MAJOR SHOPPING, GROCERY STORES, AREA BEACHES, PARKS, AND MORE!
Listing is courtesy of: SELECT PROPERTIES INC (727-934-4099)
Listing Agent: Frank Acerra (727-410-9849)
1362 E LAKE WOODLANDS PKWY, OLDSMAR, FL 34677
$849,00097 Days on yellowkey MLS ID: TB8467569
3 Days Off yellowkey (back on 4/29/2026)
REDUCED by $30,000 (3.4%) on 04/07/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2650 Built: 1992Monthly Fee: $207 Tax: $11,111 (2024)Community: Greenhaven Unit ThreeSpa: YesSingle Family
Taxes:$11,111
Remarks: Under contract-accepting backup offers. Welcome home to a rare blend of privacy, space, and resort-style living in this stunning four-bedroom, two-and-a-half-bath residence, nestled on two secluded acres within the exclusive 22-home enclave of Greenhaven II, a sought after gated community in Oldsmar. This exceptional property offers the tranquility of a private retreat while remaining close to Tampa International Airport, top dining and shopping destinations, professional sports and concert venues, and world-class Gulf beaches. From the moment you arrive, you’ll feel how special this home truly is. Inside, abundant natural light pours through large windows, illuminating tile flooring throughout and an open, airy layout designed for both everyday comfort and effortless entertaining. The open-concept kitchen and family room serve as the heart of the home—perfect for morning coffee, lively gatherings, and relaxed evenings—while separate living and dining spaces provide added flexibility for hosting or quiet moments. Step outside and embrace the best of Florida indoor-outdoor living. A heated pool and spa offer year-round enjoyment, whether you’re entertaining on the weekends, unwinding after a long day, or simply soaking in the peaceful surroundings of your expansive, private lot. The primary suite is a serene retreat featuring his-and-hers closets, while thoughtful updates—including a 2018 roof and a 2020 HVAC system—add confidence and peace of mind. Optional membership at the on-site ARDEA Country Club unlocks an impressive array of amenities, including golf, tennis, pickleball, a lap pool, fitness center, restaurant, and a full calendar of social, holiday, and private events for family and guests. Homes offering this level of privacy, acreage, and exclusivity within a gated setting are truly rare. This isn’t just a place to live—it’s a place to slow down, entertain, and fully enjoy the Florida lifestyle. Schedule your private showing today!
Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)
Listing Agent: Ian Deran (813-508-7118)
1802 FOREST DR, OLDSMAR, FL 34677
$365,000163 Days on yellowkey MLS ID: O6361686
0 Days Off yellowkey (back on 3/28/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1607 Built: 1973 Tax: $2,998 (2024)Community: Harbor Palms-Unit ThreeSpa: NoSingle Family
Taxes:$2,998
Remarks: Welcome to Highly Sought-After Harbor Palms! This stunning 3-bedroom, 2-bathroom POOL home offers true Florida living at its finest with a private inground pool, spacious layout, and exceptional indoor-outdoor flow. Step inside and you’re greeted by a bright and inviting living room featuring a cozy fireplace and skylight, creating a warm, welcoming ambiance. The formal dining room—complete with tile flooring and a convenient butler’s pantry—is perfect for hosting everything from intimate dinners to large gatherings. The well-appointed kitchen boasts abundant cabinetry and extensive counter space. The kitchen opens directly to the family room, where French doors frame picturesque views of the sparkling pool and screened lanai, making it a true entertainer’s delight. Enjoy everyday convenience with an interior laundry room, complete with a huge walk-in pantry and direct access to the garage. After a long day, retreat to the spacious primary suite, featuring a generous walk-in closet. The additional bedrooms are impressively sized, each offering great storage. Step outside to your own private oasis! The fenced backyard, storage shed, and refreshing pool make it easy to enjoy outdoor living year-round. Located just minutes from Sheffield Park, the Gulf Beaches, world-class golf, gourmet dining, downtown Tampa, and Tampa International Airport, this home offers the perfect blend of comfort, convenience, and the Florida lifestyle you’ve been dreaming of. This Harbor Palms gem truly has it all—don’t miss your chance to call it home!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Jeff Jones (205-902-3584)
311 VISTA CRUISER LN, OLDSMAR, FL 34677
$350,000157 Days on yellowkey MLS ID: TB8450597
REDUCED by $5,000 (1.4%) on 04/28/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1547 Built: 2015Monthly Fee: $248 Tax: $3,551 (2024)Community: Hayes Park VillageSingle Family
Taxes:$3,551
Remarks: What else could you want ... This charming 3-bedroom, 2.5-bath home offers the perfect blend of style, comfort, and peace of mind. Outfitted with hurricane shutters, impact windows, and a hurricane-rated garage door, the home ensures lasting security while sitting just moments from parks and walking trails. A brick-paved walkway and covered front porch create a warm welcome, leading into an inviting open-concept living, dining, and kitchen space adorned with elegant diagonal tile flooring, crown molding, and wide baseboards. The kitchen shines with 42" ebony cabinets, rounded granite countertops, a stylish tile backsplash, a spacious island perfect for casual dining, and a generous walk-in pantry. Your half bath is conveniently located off the hallway that also leads to your oversized 2-car garage. Upstairs, the primary suite feels like a private retreat, offering tray ceilings, a walk-in closet, and an en suite bath featuring an oversized step-in shower, private water closet, and dual-sink vanity. Step through your private door to a covered balcony—an ideal spot for morning coffee or evening breezes. Two additional bedrooms share a charming Jack-and-Jill bath, while the upstairs laundry room with shelving adds everyday practicality. The abundant guest parking make hosting effortless, and the community fire pit invites cozy gatherings and neighborhood connection. Enjoy yard maintenance and water included in your HOA, city-style living in an exceptional location just minutes from top-rated schools, parks, a spray park off Pine, beautiful beaches, Tampa International Airport, and a wide array of dining and shopping—including Walmart and Starbucks just a stone’s throw away. All furniture is negotiable, making this a beautifully simple, move-in-ready opportunity. Come check it out You will also enjoy Oldsmar living offering so much - tons of eateries, parks, zip line fun, pickleball courts, walking trails and so much more!
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Vanessa Leonard (727-647-2706)
4953 POINTE CIR, OLDSMAR, FL 34677
$885,0003 Days on yellowkey MLS ID: TB8502016
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2513 Built: 1997Monthly Fee: $142 Tax: $11,677 (2025)Community: Cross PointeSpa: YesSingle Family
Taxes:$11,677
Remarks: This newly renovated 4 bedroom 3 bath home is nestled in a quiet, cozy part of the elite Cross Pointe neighborhood located in the highly sought after Eastlake Woodlands development. From the moment you walk through the door, you’ll notice the attention to detail and inviting atmosphere that make this home truly special. Natural light, functional spaces, and stylish touches create a setting that’s both elegant and comfortable. Enjoy the amenities of Ardea Golf, Tennis, and Social club. This gem will not last long - schedule a viewing today.
Listing is courtesy of: HOME SOLD REALTY LLC (833-700-2782)
Listing Agent: Camilo Perez (833-700-2782)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.