Location: Oldsmar , 34677
Do Not Show Listings
1418 WOODSTREAM DR, OLDSMAR, FL 34677
$664,90054 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,098
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
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
$399,9007 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
Elementary School: Oldsmar Elementary-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)
472 TROUT LN, OLDSMAR, FL 34677
$195,900398 Days on yellowkey MLS ID: TB8369073
REDUCED by $10,000 (4.9%) on 04/30/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1998Monthly Fee: $70 Tax: $3,420 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$3,420
Elementary School: None
High School: None
Middle School: None
Remarks: Gull-Aire Village. 55+ community. Welcome to this 1998 Jacobsen home, built to newer standards and offering the perfect blend of comfort and convenience. This spacious residence features a desirable split floor plan with three bedrooms, providing ample privacy for family or guests. The chef’s kitchen is a true highlight, boasting high-quality Kraft Maid Cabinetry with custom pull-outs for effortless organization and use. A convenient washer and dryer hookup is tucked away in a kitchen closet, maximizing space and functionality. Enjoy easy-care ceramic tile and laminate flooring throughout the home. The A/C and hot water heater were both replaced approximately five years ago, ensuring peace of mind and energy efficiency. Step into the enclosed, air-conditioned Florida room at the front of the house—perfect for relaxing year-round with its stylish tile flooring. There is also a screened porch on the side, ideal for enjoying Florida’s beautiful weather. Custom concrete curbs and pavers add curb appeal, while the generously sized utility room offers excellent storage—great for bikes or hobbies. The community is vibrant and welcoming, featuring a socially active clubhouse, library, pool table, shuffleboard, Bocce ball court, and a heated pool and spa. Monthly planned activities at the clubhouse include yoga, pool exercise, bingo, cards, and line dancing, so there is always something to do. The neighborhood is golf cart friendly for added convenience. HOA fees are just $70.00 per month. Gull-Aire Village is pet friendly—you can have one pet of any size. If you have two pets, one is permitted, and the second is allowed with an emotional support letter from your doctor. You own your land here, offering security and peace of mind. Location is unbeatable! Across the street, from the community you will find AMC Theatres, Bealls, Marshalls, PetSmart, Five Below, and the Dollar Store for all your shopping needs. Great dining options nearby include Shaker and Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eve’s Family Restaurant. You are just minutes from Super Walmart, Publix, and Countryside Hospital. The stunning beaches of Honeymoon Island and Caladesi State Park are just ten miles away, perfect for weekend getaways. Outdoor enthusiasts will love the biking/walking trail along the canal, with two convenient access points from Gull-Aire. Room sizes are approximate; buyers should verify measurements. Do not miss the opportunity to own this home in a sought-after, amenity-rich community!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Jayne Phoenix (727-433-1411)
1806 FOREST DR, OLDSMAR, FL 34677
$418,000187 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
Tax Year: 2024
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)
291 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677
$249,900111 Days on yellowkey MLS ID: TB8463435
REDUCED by $8,100 (3.1%) on 04/30/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1110 Built: 1996Monthly Fee: $454 Tax: $2,205 (2025)Community: Countryside KeyTownhouse
Taxes:$2,205
Remarks: Welcome to the highly sought-after gated community of Countryside Key, ideally located in the heart of Oldsmar! This well-maintained home offers wood laminate flooring, a convenient ground-level laundry closet, and a screened-in lanai with an additional storage closet—perfect for relaxed Florida living. The kitchen opens seamlessly to the dining and living areas, creating an inviting open-concept layout ideal for everyday living and entertaining. Upstairs, you’ll find a desirable split floor plan featuring vaulted ceilings and two spacious, carpeted bedroom suites, each with its own private bath. Residents of Countryside Key enjoy a wealth of amenities, including a secure gated entrance, community pool, tennis courts, and a car wash station. Boat and RV parking are also available. Low monthly HOA fees cover cable, internet, phone, water, sewer, trash, exterior building maintenance, and exterior insurance—offering both convenience and peace of mind. Recent updates include new shut-off valves and a 2024 water heater. Ideally situated near airports, dining, shopping, entertainment, sports venues, and Florida’s award-winning Gulf beaches. Don’t miss this opportunity—schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
507 SHORE DR E, OLDSMAR, FL 34677
$239,00047 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
$375,000197 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
$795,00055 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)
130 CYPRESS LN #130, OLDSMAR, FL 34677
$160,0007 Days on yellowkey MLS ID: TB8502597
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980Monthly Fee: $571 Tax: $2,571 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$2,571
Remarks: One or more photo(s) has been virtually staged. Welcome to this two-bedroom, two-bath condominium in Oldsmar, offering 1,054 square feet and a flexible opportunity for investors, first-time buyers or seasonal residents. This residence is vacant and ready for immediate occupancy or renovation. The interior reflects the original condition, presenting a value-add opportunity for customization. The primary bedroom includes a walk-in closet, and the layout supports functional living and dining spaces. Recent updates include an air-conditioning system installed in 2025, along with a washer, dryer and refrigerator replaced in 2024. This property is well-suited for buyers seeking to personalize a residence or secure an investment with long-term potential. Conveniently near shopping, dining and commuter routes, supporting full-time and seasonal living.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (813-217-5288)
Listing Agent: Maria Azuaje (317-371-0935)
313 JEFFERSON AVE S, OLDSMAR, FL 34677
$450,0006 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)
3664 MERIDEN AVE, OLDSMAR, FL 34677
$399,90011 Days on yellowkey MLS ID: W7885202
1 Days Off yellowkey (back on 4/29/2026)
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1940 Built: 1983 Tax: $4,602 (2025)Community: West Oldsmar Sec 1Apartment
Taxes:$4,602
Remarks: Under contract-accepting backup offers. Prime income-producing duplex in Oldsmar offering strong returns and true turnkey condition. This fully renovated property at 3664 Meriden Ave features two 2-bedroom, 2-bath units, each extensively upgraded with modern, low-maintenance finishes designed to attract and retain quality tenants. Both units have been remodeled from top to bottom, minimizing near-term capital expenditures and providing immediate operational efficiency. Updates include a new roof to be installed prior to closing, new windows and sliders, new subfloors, new luxury vinyl flooring, new tall baseboards, both contemporary kitchens with brand new cabinets, quartz countertops, tile backsplash, new faucets, new SS microwave, the renovated baths include new flooring, fixtures, new vanities, new stone countertops, new lighting, new bath fans, new tile work in the shower and new tub and tile work, the bedrooms have new lighting and ceiling fans and new closet doors that are paired with fresh interior finishes of new texture and paint throughout—positioning the asset competitively within the local rental market. Located in a high-demand rental corridor, the property supports projected rents of $1,795 per unit, delivering solid cash flow potential with upside through continued rent growth. Ideal for investors seeking a stabilized asset with minimal deferred maintenance and strong tenant appeal. Strategically positioned near major employment hubs, retail, and commuter routes, this duplex benefits from consistent rental demand and long-term appreciation potential. Perfect for both seasoned investors and those looking to enter the multifamily space with a low-maintenance, high-demand asset.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Robert Bello, Jr (609-743-0650)
172 LAKEVIEW WAY #172, OLDSMAR, FL 34677
$165,00025 Days on yellowkey MLS ID: TB8496591
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1980 Tax: $3,644 (2024)Community: East Lake Woodlands CondoCondo
Taxes:$3,644
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 2 bedroom, 2 bathroom second-floor condo located in the highly desirable gated community of East Lake Woodlands. This immaculate home features upgraded luxury vinyl plank flooring throughout and offers a serene, peaceful pond view perfect for relaxing mornings or evenings. Residents enjoy access to an exceptional lifestyle with two championship 18-hole golf courses, 14 Har-Tru tennis courts, and a stunning country club. Ideally situated near world-class beaches, scenic nature parks and preserves, and with convenient access to shopping and dining, this home is the perfect opportunity to embrace the best of the Florida lifestyle.
Listing is courtesy of: CENTURY 21 INTEGRA (800-593-7653)
Listing Agent: Becki Server (727-835-9696)
120 EVELYN CT, OLDSMAR, FL 34677
$289,0009 Days on yellowkey MLS ID: TB8501596
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1450 Built: 1979Monthly Fee: $490 Tax: $5,156 (2025)Community: East Lake Woodlands Cluster HomesVilla
Taxes:$5,156
Remarks: Welcome to 120 Evelyn Ct, Oldsmar, FL 34677, a beautifully maintained villa located within the highly desirable East Lake Woodlands community, one of the most sought-after neighborhoods in Pinellas County and the Tampa Bay area. This home offers a wonderful opportunity for buyers seeking low-maintenance living in a prime Oldsmar location. This immaculate villa has been very well maintained through the years and is ready for move-in, while also allowing the next owner the opportunity to update and personalize over time. The home features a thoughtfully designed floor plan with spacious living areas and generously sized bedrooms, creating a comfortable and functional living environment. The primary suite includes a walk-in closet and private ensuite bathroom, providing privacy and convenience. The additional bedroom is also well-sized, making the home ideal for guests, seasonal living, or a home office. One of the standout features of this property is the large sunroom/lanai, offering a bright and inviting space that can be enjoyed year-round. Whether you’re relaxing with your morning coffee or entertaining guests, this versatile area adds valuable living space and enhances the overall flow of the home. Important updates include an HVAC system installed in 2015, a new electrical panel installed in 2022, and a newer water heater, providing peace of mind for the next owner. The property also includes covered parking and ample storage space, adding convenience for everyday living. The home is fairly priced based on recent comparable sales within the East Lake Woodlands community, making it a strong opportunity in today’s Oldsmar real estate market. East Lake Woodlands is known for its beautiful surroundings, mature landscaping, and central location within Pinellas County. Residents enjoy easy access to shopping, restaurants, parks, golf courses, and everyday conveniences. The property is also conveniently located with an estimated 30-minute drive to Tampa International Airport, as well as a similar drive to many of Pinellas County’s award-winning Gulf Coast beaches. If you are searching for a villa in Oldsmar within East Lake Woodlands, 120 Evelyn Ct offers a combination of location, comfort, and value in one of the Tampa Bay area’s most desirable communities. Schedule your private showing today and discover everything this well-maintained Oldsmar villa in East Lake Woodlands has to offer.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Lance Willard Llc (727-487-1894)
240 CYPRESS LN #240, OLDSMAR, FL 34677
$229,90067 Days on yellowkey MLS ID: TB8481270
REDUCED by $25,000 (9.8%) on 04/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980 Tax: $3,193 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$3,193
Remarks: Welcome to 240 Cypress Lane in Oldsmar, where effortless Florida living meets refined, turnkey luxury with tranquil water views and a premier golf lifestyle just moments away. This fully furnished, completely renovated second-floor residence offers the perfect blend of comfort, style, and security, high and dry with no flood insurance required. Step inside to a bright, open-concept layout enhanced by brand-new high-impact windows and sliders, allowing natural light to pour in while providing peace of mind year-round. The heart of the home is a stunning, fully updated kitchen, complete with modern cabinetry, sleek countertops, and all-new appliances, ideal for both entertaining and everyday living. Every detail has been thoughtfully upgraded, including new flooring, designer lighting, new electrical panel, and a New A/C system delivering a truly move-in ready experience. Enjoy peaceful pond and water views from your living space, creating a relaxing and private setting that captures the essence of Florida living. Residents also enjoy access to a heated community pool, offering a resort-style atmosphere just steps from your door, perfect for unwinding any time of year. The home also includes dedicated covered carport parking, adding both convenience and value. Perfectly positioned, this home is nestled near East Lake Woodlands Country Club, now known as Ardea Country Club, a premier golf destination in Oldsmar. The club features two newly renovated 18-hole championship courses, the North and South Courses, and recently completed an $11 million transformation, enhancing every aspect of the experience, including the golf courses, tennis facilities, and clubhouse. Located less than 30 minutes from world-class Gulf beaches, as well as Tampa International Airport (TPA) and St. Pete-Clearwater International Airport (PIE), this home offers both convenience and an unbeatable lifestyle. HOA dues provide exceptional value and convenience, including Cable TV, Internet, Community Pool, exterior maintenance, grounds maintenance, sewer, trash, and water, allowing for truly low-maintenance living. Whether you’re seeking a full-time residence, seasonal retreat, or investment opportunity, this home delivers low-maintenance living with high-end upgrades in one of Oldsmar’s most desirable locations. You’ve seen the rest, now own the best.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nick Wimperis (651-472-1506)
208 CUTLASS WAY, OLDSMAR, FL 34677
$350,00011 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 Agent: Jennifer Kashtan (813-310-7200)
1820 DRIFTWOOD CIR N, OLDSMAR, FL 34677
$379,900169 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)
1505 SUNSET WIND LOOP, OLDSMAR, FL 34677
$390,00064 Days on yellowkey MLS ID: W7883526
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1667 Built: 2018Monthly Fee: $580 Tax: $5,187 (2025)Community: Bayside TerraceTownhouse
Taxes:$5,187
Remarks: This beautiful townhouse (NEVER FLOODED) is located in the highly desirable waterfront gated community of Bayside Terrace. The home offers three bedrooms and two and a half bathrooms with a modern, open layout designed for comfortable living and entertaining. The 9 foot ceilings enhance the spacious feel and allow natural light to flow throughout the home. There is no immediate rear neighbor, providing added privacy and a more open feel from the lanai. Grilling is allowed in the backyard area, giving you the ability to enjoy outdoor cooking and entertaining. The home has been meticulously kept and shows true pride of ownership. It also includes a private 1 car garage for secure parking and additional storage. Upon entering, you immediately notice the ultra-modern feel and the exceptionally well-maintained condition of the property. The spacious kitchen features an extra-large island that is so generously sized it feels like it has its own zip code, along with an under-mount sink, quartz countertops, stainless steel appliances, and a walk-in pantry. The main living area has tile flooring throughout, creating a clean and seamless look, and opens to a screened-in lanai with brick pavers for easy indoor and outdoor living. Upstairs, the upgraded Berber-carpeted staircase with elegant railing leads to a loft area and all bedrooms. The primary suite is generously sized and includes multiple walk-in closets and a beautifully designed en-suite bathroom. Bedrooms two and three each feature carpeting and their own walk-in closets, offering excellent storage and flexibility. The home also includes hurricane shutters stored in the garage, providing added storm protection and peace of mind. Bayside Terrace offers resort-style amenities including a waterfront infinity heated salt-water pool, a covered pavilion overlooking the water, a cabana, two BBQ grills, a gas fire pit, a fitness center, clubhouse, and a dock with kayak and canoe launch access. The gated entrance and deed restrictions add an extra layer of privacy and security, while the waterfront setting allows residents to enjoy Florida sunsets and an active coastal lifestyle. Please view two videos: Tour 1 & Tour 2.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Eric Jenkins, Pa (727-409-3484)
1362 E LAKE WOODLANDS PKWY, OLDSMAR, FL 34677
$849,000102 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)
238 PELICAN DR N, OLDSMAR, FL 34677
$199,000414 Days on yellowkey MLS ID: TB8360914
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1286 Built: 1983Monthly Fee: $70 Tax: $2,285 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$2,285
Remarks: This home is in highly desirable 55+ Gull-Aire Village! This beautifully updated Palm Harbor home boasts 1,286 square feet of comfortable living space with two generous bedrooms and two modern baths. The open floor plan is perfect for entertaining family and friends, while the freshly painted interior and brand-new luxury wide-width, high-traffic vinyl plank flooring with new baseboards add a touch of sophistication throughout. The hall bath features a stunning new white wood vanity with marble top, new brushed nickel faucets, a mirrored medicine cabinet, LED lighting, and elegant custom wainscoting. The main suite bath is equally impressive, offering double white wood vanities with marble tops, (2) mirrored medicine cabinets, LED lighting, and custom wainscoting for a spa-like retreat. Both bathrooms are equipped with new shut-off valves for peace of mind. The chef’s kitchen is outfitted with a brand-new range, stainless steel refrigerator, dishwasher, range hood, and bright LED lighting. You will appreciate the spacious pantry and convenient, inside washer/dryer hookup. Relax in the inviting living room with an electric fireplace or enjoy the sunshine year-round in the spacious Florida room with acrylic windows. Additional storage is provided by a utility room—perfect for bikes and lawn equipment. The home also features a newer vapor barrier and metal roof-over. Gull-Aire Village offers incredible amenities including a socially active clubhouse, library, pool table, shuffleboard, Bocce ball court, and a heated pool & spa. There are planned events at the clubhouse every month, plus regular activities such as yoga, bingo, cards, and line dancing. The community is golf cart friendly, and the HOA is just $70.00 per month. Pet lovers rejoice—one pet of any size is welcomed, and if you have two pets, the additional pet will need an emotional support letter from the Buyers doctor for approval. You own your own land! Conveniently located across the street from AMC Theatres, Beall’s, Marshalls, PetSmart, Five Below, and Dollar Store, with a variety of restaurants including Shaker and Peel, Craft Street Kitchen, Mandolas, Country Pizza Italian Grill, and Eve’s Family Restaurant just steps away. You are only minutes from Super Walmart, Publix, and Mease Countryside Hospital. For nature lovers, the stunning beaches of Honeymoon Island and Caladesi State Parks are about ten miles away, and a scenic biking/walking trail along the canal offers two access points from Gull-Aire Village. Room sizes are approximate and should be verified by the Buyer. Do not miss your chance to own this move-in ready gem—schedule your showing today and experience all that Gull-Aire Village living has to offer!
600 S WOODLANDS DR, OLDSMAR, FL 34677
$409,99946 Days on yellowkey MLS ID: TB8488468
REDUCED by $15,001 (3.5%) on 04/12/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1952 Built: 1979Monthly Fee: $490 Tax: $4,813 (2025)Community: East Lake Woodlands Cluster HomesVilla
Taxes:$4,813
Remarks: One or more photo(s) has been virtually staged. This beautifully updated 3-bedroom, 2-bath attached villa style home is nestled in the highly sought-after Eastlake Woodlands community, offering serene preserve views in the front from your private fenced in patio and peaceful wooded and golf course views in the back. The home features a carport with a storage closet and a thoughtfully designed split-bedroom floor plan. Recent upgrades include all-new impact windows (2023), Roof (2020) a new air conditioner (2022), new washer & dryer (2022), remodeled entryway and bathrooms (2023), new blinds (2022), and remote-controlled ceiling fans throughout (2022). The living and dining areas showcase elegant crown molding, while the updated 150-amp electrical panel ensures modern efficiency. The kitchen boasts wood cabinetry, granite countertops, a glass mosaic backsplash, and stainless steel appliances. Laminate flooring extends throughout the home, with ceramic tile in the wet areas for added durability. The spacious primary suite offers a walk-in closet, access to the bonus room, and a luxurious bath with dual sinks, wood cabinetry, granite counters, and a step-in glass shower. The third bedroom also features a walk-in closet, built-in storage, and a slider to the bonus room, while the secondary bath includes a newer tile surround for the tub/shower and a stylish vanity with a granite countertop. Dont forget the huge, expansive bonus room that adds incredible flexibility for a family room, office, or hobby space. Perfectly blending comfort and style, this home delivers move-in-ready elegance in a premier location.
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)
Listing Agent: Jarod Brewer (727-647-1379)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.