Location: Oldsmar , 34677
Do Not Show Listings
375 WELLINGTON AVE, OLDSMAR, FL 34677
$1,299,00011 Days on yellowkey MLS ID: TB8492687
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2624 Built: 1993 Tax: $14,951 (2025)Community: Country Club Add To Oldsmar RevSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,951
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to your modern dream home—completely reimagined with a full 2024 designer remodel where no detail was overlooked. From the baseboards to the custom designer air vents, every finish has been thoughtfully curated and impeccably executed. The gourmet kitchen is a true showpiece, featuring full custom cabinetry with lighted drawers, newer appliances, and stunning high-end Essenza Quartzite waterfall countertops—an architectural statement rarely found outside luxury homes. Throughout the second and third floors, you’ll find polished 32x32 porcelain Onyx tile, complemented by sleek single-panel glass interior doors, designer chrome hardware, and all-new outlets, switches, and striking modern glass light fixtures and chandeliers. Every bathroom has been fully renovated with floating vanities, vessel sinks, LED mirrors, smart toilets, and all new fixtures and finishes. The primary suite offers a true retreat, featuring a dramatic three-sided gas fireplace that flows into a spa-inspired en suite with a custom concrete vanity by a local artist, freestanding soaking tub, and walk-in shower. The staircase is a statement in itself, finished with Calacatta Sunset quartz and floating frameless glass railings with chrome accents, echoed throughout the home’s balconies. Anchoring the main living space is a breathtaking 20-foot LED-lit accent wall—an unforgettable focal point that defines the home’s modern design. Situated on a full acre in the heart of Oldsmar, this property offers both luxury and freedom with no HOA. Flood insurance is approximately $800/year and transferable. The ground level features a versatile game room, gym, or flex space that opens to an expansive 1,400 sq ft paver pool deck with a two-story screened enclosure, outdoor kitchen & gorgeous pool & spa combo—perfect for entertaining and enjoying Florida living year-round. AC(2023), ROOF (2022), ELECTRIC PANEL (2023), HURRICANE RATED WINDOWS & SLIDERS (2017), POOL PUMP (2024), TANKLESS WATER HEATER (2018). Store your boat or RV on your one acre fully fenced and gated private lot. Close proximity to three waterfront parks, Pickleball, boat and kayak launch, fishing pier, restaurants, Tampa, International Airport, and the most beautiful beaches in the world. This home was meticulously designed and must be seen to be appreciated.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Jenny Neumeyer (727-482-2656)
2020 DOVER CT, OLDSMAR, FL 34677
$255,00021 Days on yellowkey MLS ID: TB8486084
3 Days Off yellowkey (back on 4/3/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1143 Built: 1983Monthly Fee: $160 Tax: $588 (2025)Community: Bayside Meadows Ph IiVilla
Taxes:$588
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Middle School: Carwise Middle-PN
Remarks: Under contract-accepting backup offers. Updated Villa in Oldsmar with Low HOA, 2024 HVAC, updated kitchen and baths, Hurricane impact window and sliders & heated Community Pool. Welcome to 2020 Dover Ct in Oldsmar, Florida—an updated 2-bedroom, 2-bath villa with a 1-car garage, ideally positioned on a quiet cul-de-sac in one of Oldsmar’s most convenient locations. Offering 1,143 square feet of thoughtfully designed living space, this home blends comfort, functionality, and low-maintenance Florida living. Recent updates provide peace of mind, including a 2024 A/C system, new duct work 2022, hurricane-rated sliders 2022, updated hurricane-rated windows 2019, garage door 2023, and beautifully refreshed kitchen and flooring with new tile extending through the hallway and into the bathrooms, updated bathrooms. Step inside through the welcoming foyer to find a light and bright interior with volume ceilings and a spacious great room with Luxury Vinyl Plank flooring is centered around a charming wood-burning fireplace—perfect for cozy Florida evenings. The updated eat-in kitchen is designed for both everyday living and entertaining, featuring abundant counter space, a flat cooktop range, stainless steel refrigerator, breakfast bar, large cabinet pantry, and the added convenience of an under-counter washer and dryer. The split-bedroom layout offers privacy, with the secondary bedroom and full bath located near the front of the home, while the primary suite is tucked away and features sliding glass doors leading to the Florida room, a large linen closet, and an updated en-suite bath with a step-in shower. Enjoy relaxing mornings or evening breezes on your Florida room that overlooking your backyard—ideal for enjoying Florida’s year-round outdoor lifestyle. With low HOA fees of just $160/month, residents enjoy true maintenance-free living including lawn care, community pool access, annual tree trimming, pressure washing of sidewalks once a year, maintenance of the rear fence behind the villa, and reclaimed water for irrigation—saving you both time and money while keeping the community beautifully maintained. Location is everything, and this home delivers—just minutes from shopping, dining, movie theaters, hospitals, medical facilities and everyday conveniences, with easy access to Tampa Road, US-19, and McMullen Booth Road for quick commutes to Tampa, Clearwater, and St. Petersburg. Outdoor enthusiasts will appreciate nearby parks, trails, and waterfront areas, including Upper Tampa Bay Park, the Oldsmar Trail, and quick access to the Courtney Campbell Causeway. World-famous Gulf beaches, Tampa International Airport, and St. Pete-Clearwater Airport are all within an easy drive. This is your opportunity to own an updated villa in Oldsmar with low maintenance, strong value, and a prime location—schedule your private showing today and start living the Florida lifestyle.
Listing is courtesy of: EXP REALTY (727-449-9276)
Listing Agent: Kathie Lea (727-422-9455)
465 HOLLY HILL RD, OLDSMAR, FL 34677
$650,00029 Days on yellowkey MLS ID: TB8486777
0 Days Off yellowkey (back on 3/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2324 Built: 1985Monthly Fee: $148 Tax: $3,265 (2025)Community: East Lake WoodlandsSingle Family
Taxes:$3,265
Remarks: Under contract-accepting backup offers. Stunning 3BR/2BA + Bonus Room, Pool Home in Gated East Lake Woodlands – Move-In Ready Resort-Style Living Beautifully updated, turnkey pool residence in the prestigious gated golf community of East Lake Woodlands, Oldsmar, FL. This highly desirable Tampa Bay suburb offers tree-lined streets, top-rated schools (zoned for East Lake area schools), optional private club access (championship golf, tennis, pickleball, fitness, dining & social events), and quick access to TPA airport (~15 min), pristine beaches (~10 miles to Honeymoon Island), shopping, and dining. -FEATURES & RECENT UPDATES - Fully remodeled kitchen (2026): soft-close solid wood white shaker cabinets, Carrera AZe quartz counters, under-cabinet lighting - Fresh Benjamin Moore interior paint throughout (2026); exterior paint (2024) - Luxury vinyl plank flooring in main living areas (2025) - Popcorn ceilings removed (2025) - New roof (2025) - Miami-Dade skylights (2025) - New appliances: dishwasher (2026), washer/dryer (2025), refrigerator (2023) - New A/C (2020) with new compressor (2025) - Screened lanai resurfaced (2024) - RainBird irrigation serviced (2025) - Hurricane-rated garage door & opener (2022) and impact-resistant sliding glass doors (2020) Step into your private backyard oasis featuring a sparkling pool and spacious screened lanai—perfect for year-round Florida entertaining and relaxation. Flood Zone: X (no flood insurance required) Community: Gated, golf & social club optional, top-rated schools. A rare combination of thoughtful recent renovations, timeless appeal, and unbeatable location. Don't miss this paradise in one of Tampa Bay's most sought-after communities!
1001 STARBOARD CT, OLDSMAR, FL 34677
$534,90013 Days on yellowkey MLS ID: TB8492967
0 Days Off yellowkey (back on 4/3/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1928 Built: 2019Monthly Fee: $580 Tax: $5,109 (2025)Community: Bayside TerraceTownhouse
Taxes:$5,109
Remarks: Under contract-accepting backup offers. WATERFRONT CORNER UNIT with very LOW, TRANSFERABLE Flood Policy! Don’t miss this once-in-a-lifetime opportunity to own the highly sought-after SANTA ROSA CORNER MODEL in the gated waterfront community of Bayside Terrace. This is the only model of its kind currently available, offering stunning water views of Tampa Bay, unmatched privacy, and an abundance of natural light throughout. This upgraded 3 bedroom, 2.5 bathroom, 2 car garage townhome has been meticulously maintained with attention to every detail. As a corner unit, it enjoys extra windows and sunlight, creating a bright and inviting atmosphere from the moment you walk in. Soaring 18 foot ceilings and an open floor plan showcase breathtaking water and sunset views from the entire main living area. The modern kitchen is both functional and elegant, featuring granite countertops, stainless steel appliances, under cabinet lighting, ample cabinetry, a large island, and a spacious walk-in pantry. Tile flooring spans the main living areas, while upgraded luxury vinyl plank flooring flows through the primary suite, stairs, and entire upstairs, combining style with easy maintenance. Additional upgrades include plantation shutters, sliding blinds, and a water filtration system. Step outside to your private screened lanai and enjoy spectacular sunsets over the bay, all while watching dolphins swim by. The first floor primary suite is a true retreat, offering coffered ceilings, serene water views, a spacious walk-in closet, and a conveniently located laundry area inside the master closet. The spa-like en suite includes dual sinks, a granite vanity, and a walk in shower. Upstairs, a large loft provides a flexible space for a game room, media room, home office, or family room, with partial water views. The two additional bedrooms are generously sized, each with walk-in closets, and share a beautifully updated full bathroom that is perfect for family or guests. The two car garage includes extra shelving and space for kayak storage. Hurricane shutters are included, and this home has never experienced storm surge or water damage from Hurricane Helene, offering rare peace of mind on the water. Bayside Terrace offers resort-style, maintenance-free living with a heated salt water infinity pool, fitness center, clubhouse, fire pit, BBQ area, and a waterfront dock with kayak and canoe launch. Ideally located near Tampa International and St Pete airports, award winning beaches, shopping, dining, and just minutes from Safety Harbor, Dunedin, and Honeymoon Island. Washer and dryer convey. This is a rare, one-of-a-kind opportunity, and the only Santa Rosa Corner Model currently available with the master room downstairs. Schedule your private showing today and secure your dream waterfront home before it’s gone.
Listing is courtesy of: TOM TUCKER REALTY (727-692-3997)
Listing Agent: Dave Doherty (727-639-2371)
240 CYPRESS LN #240, OLDSMAR, FL 34677
$254,90046 Days on yellowkey MLS ID: TB8481270
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
Elementary School: Forest Lakes Elementary-PN
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)
416 COUNTRY CLUB DR, OLDSMAR, FL 34677
$385,00059 Days on yellowkey MLS ID: TB8475710
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1293 Built: 1959 Tax: $644 (2025)Community: Oldsmar Country Club Estates Sec 2Single Family
Taxes:$644
Remarks: Nestled in the highly deisrable City of Oldsmar, this home has been tastefuly renovated. You'll love the updated kitchen with new stainless steel appliances, stone counter top and lovely build in desk. This modern kitchen has beautiful black cabinets, double sink, new range, refrigerator, dishwasher, and microwave. There are new ceiling fans throughout the home and plenty of decorator lighting. The master suite has it's own bath and modern shower. It is a beauty. The secondary bath is very modern with decorator fixtures and lighted mirror, all done very tastefully. This shower has beautiful ceramic tile and modern features. There is spacious great room and separate dining room which is leading to the perfect entertaining back yard. There are 2 decks, brick pavers and it features a jacuzzi tub. You'll love the separate shed for storage and fenced in yard. There is plenty of room for your toys with gated entry to the back yard. No CDD or HOA fees here but there are several parks and a boat ramp in the neighborhood. Move in ready and a must see.
Listing is courtesy of: MURRAY BELL REAL ESTATE LLC (813-629-8202)
Listing Agent: Jenny Meers (813-748-8112)
110 DEERPATH DR, OLDSMAR, FL 34677
$1,199,90091 Days on yellowkey MLS ID: TB8462357
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4246 Built: 1991Monthly Fee: $263 Tax: $10,446 (2024)Community: Deerpath Unit OneSingle Family
Taxes:$10,446
Elementary School: Cypress Woods Elementary-PN
Tax Year: 2024
Remarks: Simply sensational in prestigious Deerpath of East Lake Woodlands!! Enter through double leaded glass entry doors to this spectacular, sprawling executive residence! 4,246 sq. ft. of exceptionally well-planned design and custom built to precise detail. Soaring ceilings with four bedrooms, plus a study that could be a 5th bedroom and 3.5 baths… elegantly designed! Privacy prevails on this gorgeous, wooded home site surrounded by lush landscaping. Enter the grand foyer and take in the refined view of three sets of French doors with lovely transom windows looking out on the lanai and pool area. The formal living and dining areas highlight the gorgeous architecture of the home and the sunken living room is beautifully designed with plant shelves and lighted niches! The 5th bedroom is currently used as an office. It has its own set of French doors and boasts custom built-in desk and shelving with granite counters and desktop. A convenient half bath completes the entry area and leads to the magnificent kitchen! Wow! An entertainer’s dream! Ingenious design with prep space and cabinetry galore! Designer quartz counters are stunning! Large center island as well as a breakfast bar and butler’s pantry with beverage fridge in addition to a generous sized eat-in breakfast room. Stainless appliances include a 4-door refrigerator. Huge walk-in pantry! Lovely bead board accents with chair railing, gorgeous pendant lighting…designer lighting throughout the home! The kitchen overlooks the large family room centered by a travertine faced wood burning fireplace and walk-in bar with sink. The primary retreat is nothing short of fabulous! Large sitting area, romantic 2-way wood burning fireplace and totally updated spa-like ensuite bath with massive counter space, separate sink areas, whirlpool tub, walk in shower with designer tile work, water closet, Venetian finish on walls and a massive walk-in closet. Secondary bedrooms are vast and have large wall closets or walk-in closet space! The shared bath space is creatively redesigned with fashionable updates and substantial counter space accented by double sinks with splendid oiled bronze hardware. And the additional full bath/pool bath boasts the most recent upgrades with the same designer granite counters and a beautifully tiled, glass enclosed walk-in shower. All bathrooms are stylishly upgraded. Entertaining and family space is extended outdoors to the grand lanai and pool area! Gorgeous pool with spillover spa and vaulted screen enclosure looks out on a lushly landscaped and private wooded paradise! The convenient pool bath has been recently, renovated with designer touches. And a poolside kitchen area with sink completes the setting and allows for ultimate entertaining! Truly a must see. Endless upgrades and details! All found within the gates of the fabulous East Lake Woodlands Country Club community… A+ rated schools, close to everything, medical, shopping, parks, restaurants, TIA and gorgeous Gulf beaches! An extraordinary find!
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Nancy Leslie (727-789-5555)
165 MOBBLY BAY DR, OLDSMAR, FL 34677
$1,239,900202 Days on yellowkey MLS ID: TB8430614
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3945 Built: 2012Monthly Fee: $183 Tax: $8,887 (2024)Community: Estuary Of Mobbly BaySingle 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!!
9009 PALM KEY AVE, OLDSMAR, FL 34677
$674,90097 Days on yellowkey MLS ID: TB8461356
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2587 Built: 2018Monthly Fee: $580 Tax: $6,740 (2025)Community: Bayside TerraceTownhouse
Taxes:$6,740
Remarks: Seller is offering a $5,000 CREDIT towards closing costs or an interest rate buy down! — Experience elevated WATERFRONT LIVING in this beautifully upgraded townhome located within the gated community of Bayside Terrace. This spacious waterfront townhome presents a rare opportunity and an added bonus is that the flood insurance is ASSUMABLE to new buyers for currently $1,101 annually. Enjoy a low maintenance lifestyle and even a lock up and go ability if it's your second home as the HOA INCLUDES: cable, internet, water, trash, roof and grounds maintenance, gated access, with electricity as the only additional utility needed. This rare, oversized waterfront unit in this community is one of a kind as it has expanded water views from the main floor that most other units do not have. It also provides additional natural lighting in the unit. Enjoy these stunning bay views from the kitchen, living, dining and primary bedroom spaces. High ceilings and an open-concept floor plan make this space feel expansive while the upgraded kitchen is designed for both everyday living and entertaining. Featuring an extended island, side bar/coffee station with glass-front cabinetry, and a spacious walk-in pantry. This unit has OVER $57k IN BUILDER UPGRADES making it a truly unique unit. Upstairs, the waterfront owner’s suite offers a serene retreat with water views and a spa-inspired en suite bath complete with a soaking tub, separate shower, dual vanities, and a very large walk-in closet. Two additional bedrooms and a generous bonus room provide flexible living options for a media room, game room, or play space. An oversized laundry room conveniently located near the primary suite upstairs, so no need to drag clothes downstairs. The fourth bedroom is downstairs and is currently configured as a home office but can easily be converted back to a bedroom if desired. Enjoy peaceful mornings and sunset views from the screened lanai overlooking the water, or take advantage of the RESORT STYLE AMENITIES Bayside Terrace is known for, including an infinity pool overlooking Old Tampa Bay, fitness center, outdoor grills, fire pit, kayak launch and storage, and a waterfront pier ideal for fishing and relaxation. LOCATION, LOCATION, LOCATION -- Ideally situated just minutes from downtown Oldsmar, approximately 10 minutes from Safety Harbor, 20 minutes from Honeymoon Island and Dunedin, 25 minutes to Tampa International Airport, and 30 minutes from Clearwater Beach. You have to see this in person!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Nisa Gonzalez Smook (813-400-3680)
507 SHORE DR E, OLDSMAR, FL 34677
$239,00026 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)
271 HEMINGWAY DR, OLDSMAR, FL 34677
$385,000211 Days on yellowkey MLS ID: TB8426952
REDUCED by $4,000 (1.0%) on 04/02/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1452 Built: 1998Monthly Fee: $265 Tax: $1,157 (2024)Community: Sun Ketch Twnhms At Cypress LakesTownhouse
Taxes:$1,157
Remarks: One or more photo(s) has been virtually staged. Welcome to this inviting 3-bedroom, 2.5-bath townhome with a private garage, perfectly set on a premier conservation lot, in the quaint Oldsmar community of Sun Ketch Townhomes of Cypress Lakes. Step inside to find brand-new luxury vinyl plank flooring and a bright, open layout. The spacious great room features sliding glass doors leading to a sunroom, expanding your living area while offering serene views of the conservation! The kitchen is both functional and stylish, with white cabinetry, solid-surface countertops, tile flooring, a breakfast bar and a closet pantry. For added convenience, the inside laundry room—complete with full-size Bosch washer and dryer—is located just off the kitchen. Upstairs, the primary suite impresses with vaulted ceilings, a walk-in closet and a private bath, while the additional bedrooms are well-sized for family, guests, or office space. Enjoy the saltwater, community pool, a low HOA fee of only $265 per month and the unbeatable location! Oldsmar is the gateway to Tampa, offering easy access to shopping, dining, parks, Tampa Skating Academy, and highly rated schools including Forest Lakes Elementary, Carwise Middle, and East Lake High. Plus, Tampa International Airport is less than 30 minutes away!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Marcy Daniels (727-560-8080)
219 CYPRESS CT #219, OLDSMAR, FL 34677
$185,000103 Days on yellowkey MLS ID: TB8460111
1 Days Off yellowkey (back on 4/2/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980Monthly Fee: $586 Tax: $2,893 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$2,893
Remarks: Under contract-accepting backup offers. Welcome to East Lake Woodlands – Cypress Estates, a gated golf course community offering maintenance-free Florida living. This updated ground-floor corner unit is move-in ready and perfectly positioned at the end of a quiet street for added privacy. This 2-bedroom, 2-bath condo features an open, airy floor plan with high ceilings and abundant natural light. Enjoy peaceful views from your screened-in porch overlooking a tranquil pond, ideal for relaxing and enjoying Florida wildlife. The spacious kitchen is designed for both function and style, featuring solid wood cabinetry, granite countertops, pantry, lazy Susan, recessed lighting, and ceiling fan. The primary suite offers two walk-in closets and a private en-suite bath with a walk-in shower and granite vanity. The guest bedroom includes brand-new luxury vinyl plank flooring (2025) and a large built-in closet. The second bath features a tub/shower combo, granite counters, and updated lighting. Recent Updates Include: ?? Electric Panel (2020) ?? HVAC (2021) ?? New Water Heater & Dishwasher ?? Updated Lighting & Bathrooms ?? LVP Flooring (2025 – Guest Bedroom) Additional features include assigned covered parking and access to a solar-heated community pool. The monthly HOA covers water, sewer, trash, cable, and internet, providing exceptional value. Located in the heart of Palm Harbor, just minutes from top-rated schools, shopping, dining, golf, and Gulf beaches, with easy access to Tampa International Airport, Downtown Dunedin, Honeymoon Island, and Clearwater Beach. Ideal for full-time residents, seasonal living, or investment—schedule your private showing today!
Listing is courtesy of: ORANGE GROVE PROPERTY SOLUTIONS (727-336-3202)
Listing Agent: Tara Cook (727-336-3202)
1705 IRONWOOD CT E, OLDSMAR, FL 34677
$330,00032 Days on yellowkey MLS ID: TB8486052
REDUCED by $5,000 (1.5%) on 04/02/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1206 Built: 1973 Tax: $1,600 (2025)Community: Harbor Palms-Unit SixSingle Family
Taxes:$1,600
Remarks: Welcome to this beautifully renovated 2-bedroom, 2-bathroom home—perfect for first-time buyers or those looking to downsize without sacrificing comfort. The stunning kitchen, remodeled last year, features elegant quartz countertops and new stainless steel appliances, creating a modern and inviting space for cooking and entertaining. Just off the kitchen, you'll find a very spacious area that can easily serve as a family room, home office, or versatile flex space to suit your lifestyle. Step outside to enjoy the large backyard—perfect for relaxing, gardening, or hosting gatherings. Situated on a quiet street, this cozy yet stylish home is truly move-in ready. According to the owners, the A/C was replaced in August 2018 and the roof was replaced in June 2025, providing added peace of mind for the new owner. Don’t miss this opportunity to own a beautifully updated home with modern finishes and plenty of space to enjoy.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Aned Pantoja (813-264-7754)
504 FEDERAL ST, OLDSMAR, FL 34677
$1,280,000190 Days on yellowkey MLS ID: TB8427180
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2961 Built: 2026 Tax: $1,498 (2024)Community: Oldsmar Rev MapSingle Family
Taxes:$1,498
Remarks: This stunning new three-story residence by Danva Construction perfectly blends modern luxury with resilient, high-end design. Located at 504 Federal Street in the desirable waterfront community of Oldsmar, this home is built for peace of mind with a solid concrete block structure, pilings, impact-resistant windows, and a durable TPO roof, all backed by a comprehensive builder warranty. The exterior is finished in Sherwin Williams Chantilly Lace, creating a clean, modern curb appeal enhanced by professional landscaping and a signature magnolia tree. Inside, the open-concept layout features soaring ceilings, porcelain tile flooring, and a gourmet kitchen that serves as a true showpiece. The kitchen is complete with a waterfall island, designer backsplash, and premium Bosch 800-series appliances. The luxurious primary suite offers a spa-inspired retreat with a freestanding soaking tub and porcelain tiled walls. Indoor-outdoor living shines with a second-floor porcelain tile balcony and a covered lanai. Note that some images are virtually staged to show the home's potential. BUYER INCENTIVES: Take advantage of an $80,000 pool credit to be installed after closing by a vendor of the buyer's choice (ask for details; restrictions apply). Additionally, secure an interest rate buy-down when using our preferred lender, Revolution Mortgage. Perfectly positioned just one block from Tampa Bay and five minutes to Mobbly Bayou Beach Park, this home offers a lifestyle of privacy and convenience. Oldsmar is a charming waterfront community known for its parks and trails, with effortless access to Tampa International Airport (under 20 mins), Downtown Tampa (30 mins), and the world-famous beaches of Clearwater. The location is a true paradise for outdoor enthusiasts and urban commuters alike. You are steps away from the Upper Tampa Bay Trail, offering miles of scenic cycling and jogging paths. Just minutes away, the historic downtown Oldsmar district provides an array of boutique dining, local craft breweries, and community events like the annual Oldsmar Days. For shopping, the International Plaza and Bay Street are a short drive away, offering world-class retail experiences. Nature lovers will appreciate being adjacent to the Mobbly Bayou Wilderness Preserve, featuring over 400 acres of kayaking, hiking, and even a zip-line adventure park. Golfers can enjoy proximity to several championship courses including the nearby East Lake Woodlands Country Club. Whether you are catching a flight for business or spending a Saturday at Honeymoon Island State Park, this central location puts the very best of the Florida Gulf Coast right at your doorstep. This rare opportunity combines elevated finishes and resilient materials in a highly sought-after location.This rare opportunity combines elevated finishes and resilient materials in a highly sought-after location. All financing information is for illustrative purposes only and not a commitment to extend credit.
Listing is courtesy of: ENGEL & VOLKERS TAMPA DOWNTOWN (813-863-1986)
Listing Agent: Virginia Torres Bond (813-352-2933)
470 HICKORYNUT AVE, OLDSMAR, FL 34677
$795,00034 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 WoodlandsSingle 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)
2044 SHEFFIELD CT, OLDSMAR, FL 34677
$190,000494 Days on yellowkey MLS ID: TB8327277
4 Days Off yellowkey (back on 11/10/2025)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1986Monthly Fee: $110 Tax: $1,603 (2023)Community: Sheffield Village At Bayside MeadowsVilla
Taxes:$1,603
High School: Countryside High-PN
Tax Year: 2023
Remarks: Under contract-accepting backup offers. Short Sale. High and dry with NEW ROOF and NEW HVAC!! Welcome to this charming 2-bedroom, 2-bathroom single-family villa, offering a perfect blend of comfort and style. As you enter, you'll be greeted by volume ceilings that create an open, airy atmosphere throughout the home. The spacious kitchen features beautiful granite countertops and wood cabinets, providing both elegance and functionality. Stainless steel appliances complete the modern kitchen, making it ideal for cooking and entertaining. Relax or entertain in your private enclosed patio or enjoy your own private yard, fully enclosed by a vinyl fence for added privacy and security. This home also boasts a new roof and a new HVAC system, ensuring peace of mind for years to come. Located just a short walk from the community pool, this villa is in a highly desirable school district, making it a fantastic option for families. Best of all, the HOA fees are only $110/month, offering incredible value for the community. Don’t miss the opportunity to make this wonderful home yours!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Christopher Grasso (727-379-2376)
204 WINDWARD PL #36, OLDSMAR, FL 34677
$195,00013 Days on yellowkey MLS ID: A4686982
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 879 Built: 1984 Tax: $3,166 (2025)Community: Meadows Condo At East Lake WoodlandsCondo
Taxes:$3,166
Remarks: Welcome to 204 Windward Place #36, a well-maintained and move-in-ready condo located in the desirable East Lake Woodlands community in Oldsmar, Florida. This residence offers a comfortable layout with abundant natural light and a private outdoor space ideal for relaxing or enjoying morning coffee. The interior has been thoughtfully maintained, providing a clean and inviting living environment suitable for a primary residence, seasonal use, or investment. Assigned parking is included, along with convenient guest parking. East Lake Woodlands is a gated community offering a secure and established setting with mature landscaping and scenic surroundings. Optional membership opportunities are available at the nearby Ardea Country Club, which features golf, tennis, fitness, pool, and dining amenities. Conveniently located near Tampa, Clearwater, and St. Petersburg, this property provides easy access to Gulf beaches, shopping, dining, medical facilities, and Tampa International Airport. This property presents an excellent opportunity for buyers seeking low-maintenance living in a well-located Pinellas County community. Schedule your private showing today.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Robert Dinan (941-993-7455)
3087 DUANE AVE, OLDSMAR, FL 34677
$350,000172 Days on yellowkey MLS ID: TB8441582
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1969 Tax: $4,131 (2024)Community: West Oldsmar Sec 1Single Family
Taxes:$4,131
Remarks: Back on the market due to buyer’s financing. THIS HOME NEVER FLOODED! Welcome to this move-in-ready home located in one of West Oldsmar’s most desirable neighborhoods, offering comfort, functionality, and thoughtful design. Situated on nearly one-third of an acre, this property provides generous outdoor space, privacy, and flexibility. The home features solar panels that significantly reduce monthly electric costs, often resulting in utility credits. Additional improvements include a metal roof, hurricane-rated windows, and elevated entryways. Water-management enhancements such as a front culvert drain, French drains, and a sump pump are in place to support effective drainage. Seller reports no known flooding of the home; buyers to verify all information. Inside, the open-concept layout connects the main living areas seamlessly, creating an ideal setting for everyday living and entertaining. The home also includes a spacious in-law suite with a private entrance, offering flexibility for guests, multi-generational living, or a home office. The fully fenced backyard features mature landscaping, a variety of fruit trees, and a paved patio area with space to customize an outdoor kitchen or firepit. A custom-built shed/workshop provides additional storage or can be used for hobbies, creative space, or a studio. Conveniently located near Gulf Coast beaches, parks, shopping, and downtown Dunedin, Clearwater, and St. Petersburg, this home offers peaceful residential living with easy access to area amenities. No HOA restrictions. Preferred lender offering a 1/1 interest rate buydown (subject to buyer qualification and lender terms). Schedule your private showing today.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (813-908-8788)
Listing Agent: Yhotzmine Fields (813-613-0411)
4007 PALM KEY AVE, OLDSMAR, FL 34677
$639,000189 Days on yellowkey MLS ID: TB8435073
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2587 Built: 2019Monthly Fee: $580 Tax: $7,398 (2024)Community: Bayside TerraceTownhouse
Taxes:$7,398
Remarks: Walk in the front door and look straight out to the water. Head out to the screened-in back porch to hang out and enjoy the views, from dolphins and mother duck with her ducklings, to the pink & orange glowing sunsets. This unit comes with floodplain X zoning tied to the title, which means you’re grandfathered in, and the cheap flood insurance is transferable to you (less than $800/yr.). Soaring ceilings, open floor plan, hard floors throughout, and a finished garage with a high-end epoxy floor that makes it feel like you’re parking in a showroom. Built in 2019, it looks and feels fresh and new. 1st floor bedroom with water views (great for guests!). Large media room upstairs with numerous possibilities. It could be a game room. It could be a gym or just a TV area. 3 bedrooms upstairs, including the master. The master bath overlooks the water with an oversized tub, a walk-in shower, dual vanities, and a custom walk-in closet. DirectTV, Frontier internet, water, recycling, and trash (2x/week) are included in the monthly HOA fee. The unit is far enough away from the gate, where you won't hear the road noise of 580. Bayside Terrace offers an array of amenities, including an infinity-edge swimming pool, BBQ area, a gym, a fire-pit, and a community dock with kayak, paddleboard, and canoe launch. This exceptional townhome provides the perfect blend of luxury, comfort, and Florida's natural beauty
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Jacob Gross (727-303-2063)
1704 HIBISCUS CIR N, OLDSMAR, FL 34677
$389,00056 Days on yellowkey MLS ID: TB8476647
0 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1430 Built: 1981 Tax: $6,573 (2025)Community: Harbor Palms Unit 6 ASingle Family
Taxes:$6,573
Remarks: Under contract-accepting backup offers. BACK ON THE MARKET!!! Seller offering $5,000 credit to buyer - make it yours!!!! Welcome to this inviting Florida home designed for comfortable living and effortless outdoor enjoyment. The highlight of the property is the private, screened-in pool and expansive patio, surrounded by mature tropical landscaping that creates a peaceful setting ideal for relaxing or entertaining year-round. Inside, the home offers a functional, open layout with seamless indoor–outdoor flow from the main living areas to the pool and patio. Tile flooring throughout the main living spaces provides durability and easy maintenance, well suited for Florida living. The updated kitchen is well-appointed with ample cabinetry, generous counter space, stainless steel appliances (including a double oven range) and granite countertops, with an open connection to the dining and living areas making everyday living and entertaining easy and comfortable. The primary suite features a spa-inspired bathroom complete with a freestanding clawfoot tub and separate shower, creating a calm retreat at the end of the day. The garage has been converted to provide additional flexible space with storage, suitable for a third bedroom, home office, or bonus room. A dedicated laundry room adds everyday convenience. Additional features include owned solar panels, newer windows, and sliding glass doors. This home combines privacy, functionality, and true Florida outdoor living - a great opportunity for buyers seeking space, comfort, and a backyard designed to be enjoyed.
Listing is courtesy of: REALTY ONE GROUP BEYOND (727-900-7174)
Listing Agent: Chris Ziebell (727-900-7174)
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