Location: Oldsmar
Do Not Show Listings
2151 DIAMOND CT, OLDSMAR, FL 34677
$1,350,000188 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,378
Elementary School: Cypress Woods Elementary-PN
High School: East Lake High-PN
Tax Year: 2024
Middle School: Carwise Middle-PN
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)
103 CUTLASS WAY, OLDSMAR, FL 34677
$345,00069 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
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: OPEN HOUSE THIS SUNDAY 1-3 pm!!! 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)
382 ROSALIND LN, OLDSMAR, FL 34677
$822,000288 Days on yellowkey MLS ID: TB8408993
1 Days Off yellowkey (back on 5/1/2026)
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: Under contract-accepting backup offers. 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)
219 BAY ARBOR BLVD, OLDSMAR, FL 34677
$560,00016 Days on yellowkey MLS ID: TB8498550
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1873 Built: 2000Monthly Fee: $100 Tax: $7,973 (2025)Community: Bay Arbor Unit 1ASingle Family
Taxes:$7,973
Remarks: Mrs. Clean lived here!! This beautiful home is ready for its new owners! Vaulted ceilings and an open floorplan welcome you as you step inside. The Living Room is HUGE, a wonderful place for family gatherings and entertaining for holidays and parties. The large Kitchen opens up to the Living Room for an expansion on entertaining space, featuring solid wood cabinets, matching Stainless Steel Frigidaire Appliances, and a large Breakfast Nook. The Formal Dining Room is set right across from the Kitchen, and is the perfect space for formal gatherings and family dinners. It even has a 4.5' x 2.5' nook that would house a China Cabinet or dry bar if desired. This home offers a split plan, providing maximum privacy to the Master Suite, as well as to the "Guest Wing" and other guest bedrooms. The Master Bedroom features a walk-in closet, access to the back patio, and a large en-suite Bathroom with dual vanities, a jetted tub and a standing shower. The "Guest Wing" or "Home Office Wing" is a wonderful layout to suit any needs. It has a bathroom located right off of the Bedroom, and is set apart from the rest of the bedrooms for added privacy. The other 2 Bedrooms are Jack-and-Jill style, both accessing the 3rd Full Bathroom. Large sliders in the Living Room open up to the peaceful back patio, laced in Slate Tile and fully covered. This space is a sanctuary, overlooking a small pond and greenery instead of facing a rear neighbor. The sun rises in the front of this home, so it is easy to enjoy your morning coffee at sun-up, as well as enjoy the sunsets thanks to the shade provided by the natural greenery. The Roof and Water Heater are NEW 2022, and the A/C was replaced in 2021! LOW HOA FEES only $100/month. This community is gated, with a playground and a community pool, as well as sidewalks for your morning jogs or evening walks! What's not to love?? Move right in and make this home your own!! Only a 30-minute drive to Tampa Int'l Airport, a 25-minute drive to Honeymoon Island, and just minutes from shopping, dining, and all you need to live your Florida dream to its fullest! Located in X Zone! That's right, NO FLOOD ZONE!
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Jessica Jurek (727-487-4957)
634 TIMBER BAY CIRCLE W, OLDSMAR, FL 34677
$321,50040 Days on yellowkey MLS ID: TB8489706
0 Days Off yellowkey (back on 4/30/2026)
REDUCED by $3,400 (1.0%) on 04/24/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1056 Built: 1985 Tax: $4,283 (2025)Community: Shoreview Phase 2 Blk 6, Lot 3Single Family
Taxes:$4,283
Elementary School: Oldsmar Elementary-PN
Remarks: Under contract-accepting backup offers. Motivated Seller! Move-In Ready Oldsmar Home! Welcome to this 3-bedroom, 2-bath home home located in the heart of Oldsmar, offering easy access to Tampa, Clearwater, Safety Harbor, and surrounding areas. This move-in ready property combines comfort, convenience, and a great outdoor living space. Inside you'll find a functional layout featuring an interior laundry area with upgraded Washer and Dryer(2023). Other recent upgrades include Refrigerator, Garbage Disposal, and Water Heater(2024) and a new Heat/Air System (2025). Granite and stainless steel in kitchen and updated Bathrooms. Step outside to enjoy a fully fenced, pet-friendly backyard designed for relaxing and entertaining. The outdoor space includes a large screened-in lanai and a spacious wood deck -perfect for barbeques, gatherings, or simply enjoying sunny Florida days. Also Minutes away from R.E. Olds Park which features an Amphitheater, Fishing pier, Picnic shelters, Playgrounds, Sand Volleyball and trails. Also occasionally through the year there are music concerts and festivals! This centrally located home offers the perfect blend of updates, outdoor living, and great accessibility. A great opportunity for buyers seeking comfort, convenience, and a welcoming place to call home. Property also remained safe and dry during the most recent Hurricanes and has never had any flooding issues in prior years either! Schedule your showing today!
Listing is courtesy of: AMERICAN HERITAGE REALTY, INC. (727-726-7272)
Listing Agent: Catherine Katopis (727-656-6862)
1418 WOODSTREAM DR, OLDSMAR, FL 34677
$664,90052 Days on yellowkey MLS ID: TB8485836
REDUCED by $5,000 (0.7%) on 04/30/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2292 Built: 1990Monthly Fee: $470 Tax: $4,098 (2025)Community: Cross Creek Unit 1Single Family
Taxes:$4,098
Remarks: It’s time to LEVEL UP your VIEW with this stunning 4 BEDROOM 2.5 BATH home overlooking serene WATER and CONSERVATION views in the prestigious, gated community of East Lake Woodlands. Water views greet you from the moment you drive up to this new two story masterpiece. Follow the lush landscape to a private entrance that leads you into the grand foyer of your new home. As soon as you enter, you’ll love the clean blend of modern and traditional elements in this immaculately maintained home. Hardwood floors, soaring ceilings and a grand staircase give an impressive first impression. Every room has its own elegance from the den or formal living room overlooking the front yard to the formal dining room with wainscotting and crown molding that connects to the kitchen. The chef in the house will love preparing meals in the updated kitchen with granite countertops, stainless steel appliances and plenty of cherry wood cabinetry for storage. The kitchen overlooks the family room and has an adjoining dining area, so you’re not isolated while entertaining guests. The perfectly polished family room is ideal for cuddling up near the fireplace on cool nights or letting the sunshine in as you and your guests enjoy views of the stunning pool and waterfront. The sliders and french doors open to a stunning Florida paradise just outside your backdoor. Watch birds and wildlife catch their morning breakfast on the preserve while you enjoy a cup of coffee on the screened in lanai. The heated pool features year round enjoyment and is surrounded by travertine tile. This area will quickly become your favorite part of your new home with serene views for as far as the eye can see. When it’s time to retire, find comfort in your primary retreat located on the first floor of the home. This spacious room also features private access to the pool and conservation views, plus an en suite bathroom with his and her walk-in closets. The spa-like bathroom features a walk in shower, huge soaking tub and a huge double sink vanity fit for royalty. Journey upstairs and enjoy striking views of the inside and outside of the house as well as 3 more bedroom retreats and a shared bathroom. Each room has its own charm, whether it’s overlooking the pond in the front of the house or conservation and creek views at the back, your guests will appreciate the comfort and fresh vibe of these spaces. A shared bathroom with updated vanity and tub/shower combo is the perfect space to clean up after a day on the golf course. The gated community of East Lake Woodlands is home to the newly updated Ardea Country Club offering premier exclusive membership for golfing and racquet facilities, fitness center, olympic size pool, spa, and many more optional amenities. The 2 car garage has plenty of space for a golf cart with added storage in the adjoining indoor laundry room. With roof (2022) and water heater (2019), the only thing left to do is LEVEL UP and start enjoying the VIEW!
Listing is courtesy of: TOM TUCKER REALTY (727-692-3997)
Listing Agent: Dave Doherty (727-639-2371)
307 COUNTRY CLUB DR, OLDSMAR, FL 34677
$399,9005 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
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)
1806 FOREST DR, OLDSMAR, FL 34677
$418,000185 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
$239,00045 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)
1802 CHINABERRY DR, OLDSMAR, FL 34677
$375,000195 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
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
$795,00053 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)
313 JEFFERSON AVE S, OLDSMAR, FL 34677
$450,0004 Days 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)
509 CYPRESS VIEW DR, OLDSMAR, FL 34677
$634,00015 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
$350,0009 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)
1820 DRIFTWOOD CIR N, OLDSMAR, FL 34677
$379,900167 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
$849,000100 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)
4953 POINTE CIR, OLDSMAR, FL 34677
$885,0006 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)
1654 BAYHILL DR, OLDSMAR, FL 34677
$570,000200 Days on yellowkey MLS ID: TB8438417
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2320 Built: 1995Monthly Fee: $177 Tax: $5,855 (2024)Community: CreeksideSingle Family
Taxes:$5,855
Remarks: "SELLER OFFERING $6000 TOWARDS CLOSING COSTS" THIS HOME SITS IN THE QUAINT SECLUDED CREEKSIDE COMMUNITY INSIDE THE GATES OF EASTLAKE WOODLANDS, LARGE FAMILY HOME OF 4 BEDROOMS, 2 AND HALF BATHS, 2 CAR GARAGE WITH POOL, YOUR OPEN CONCEPT OF DINING AND LIVING ROOM GREAT FOR THE FAMILY TO GATHER, KITCHEN WITH GRANITE COUNTER TOPS AND UPDATED BACKSPLASH, APPLIANCES TO INCLUDE DISHWASHER OCTOBER 2025, FAMILY ROOM WITH SLIDING GLASS DOORS GOING TO YOUR PERSONAL PARADISE TO ENJOY YOUR SCREENED ENCLOSED PAVED PATIO INGROUND POOL OUT DOORS ANOTHER GREAT ENTERTAINMENT SPACE, THEN OUTSIDE TO SWING AND ENJOY THE WILD LIFE AND DEER AND THE PRIVATE AND QUIET BROOKER CREEK PRESERVE AREA, THEN YOUR BEAUTIFUL STAIRCASE TO YOUR PRIMARY BEDROOM RETREAT WITH LARGE EN-SUITE BATHROOM, INSIDE LAUNDRY ROOM, AC SYSTEM INSTALLED 2021, ROOF 2018. DON'T MISS OUT ON THIS RARE OPPORTUNITY TO OWN THIS MUCH SQUARE FOOTAGE FOR SUCH A GREAT COMMUNITY. POSSIBILITIES ARE ENDLESS!!
Listing is courtesy of: ECKERT REALTY & PROPERTY MGMT (727-240-0668)
Listing Agent: Karen Hutson (727-240-0668)
4766 STONEVIEW CIR, OLDSMAR, FL 34677
$645,00037 Days on yellowkey MLS ID: TB8487161
4 Days Off yellowkey (back on 4/27/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2114 Built: 1993Monthly Fee: $108 Tax: $3,755 (2025)Community: StonebriarSingle Family
Taxes:$3,755
Remarks: Under contract-accepting backup offers. Welcome to an exceptional opportunity in the highly desirable Stonebriar enclave of East Lake Woodlands—where timeless design meets effortless Florida living. This impeccably maintained four-bedroom, two-bath pool home showcases true pride of ownership and offers a seamless blend of comfort, functionality, and style. From the moment you arrive, the home’s pristine condition and inviting curb appeal set the tone. Step through the front door and be immediately captivated by a stunning sightline that draws your eye through the living space to the screened lanai and sparkling pool beyond—an ideal introduction to the indoor-outdoor lifestyle that defines this residence. To the right, the formal dining room offers generous proportions, perfect for hosting gatherings both intimate and grand. Straight ahead, the formal living room provides direct access to the lanai, creating a fluid transition for entertaining and allowing you to fully embrace Florida’s beautiful weather year-round. Privately positioned to the left of the entry, the primary suite is a serene retreat featuring its own access to the lanai. The en suite bath is thoughtfully appointed with a deep soaking tub, step-in shower, and a spacious walk-in closet—delivering both comfort and convenience. At the heart of the home, the updated kitchen is a standout, boasting white shaker cabinetry, stone countertops, and an elegant tile backsplash. A breakfast bar and optional nook space add flexibility, while the open layout flows effortlessly into the family room, complete with a cozy wood-burning fireplace—perfect for relaxed evenings at home. The split-bedroom floor plan enhances privacy, with three additional generously sized bedrooms located toward the rear of the home, each offering ample closet space. The secondary bath features a tub/shower combination and provides direct access to the laundry room and lanai, functioning perfectly as a pool bath. Step outside to your private oasis—an expansive screened lanai featuring a solar heated saltwater pool, ideal for year-round enjoyment. The covered area offers the perfect setting for outdoor dining and lounging, and select patio furnishings are available for purchase, making this space move-in ready for immediate enjoyment. A spacious backyard completes the outdoor experience. With its thoughtful layout, stylish updates, and inviting indoor-outdoor flow, this home is truly ready for its next chapter. Roof 2013, HVAC 2024, Hurricane rated impact windows throughout, new gutters and pool cage rescreening. Don’t miss the opportunity to experience everything this exceptional property has to offer—schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Vanessa Leonard (727-647-2706)
165 MOBBLY BAY DR, OLDSMAR, FL 34677
$1,219,900221 Days on yellowkey MLS ID: TB8430614
REDUCED by $20,000 (1.6%) on 04/21/2026
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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