Location: Oldsmar
Do Not Show Listings
218 CARYL WAY, OLDSMAR, FL 34677
$198,00042 Days on yellowkey MLS ID: TB8499124
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1979 Tax: $2,995 (2025)Community: East Lake Woodlands CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,995
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
Remarks: Welcome home to this beautifully updated second-floor condo located in the highly sought-after, gated community of East Lake Woodlands with golf course views. Known for its peaceful surroundings and resort-style living, this community offers both comfort and convenience in an ideal setting. Step inside to discover a bright and airy interior filled with natural light. This move-in-ready residence has been thoughtfully upgraded with a brand-new eat-in kitchen, featuring new white wood cabinetry, quartz countertops, and new appliances—perfect for everyday living and entertaining alike with pass thru window into the dining area. Fresh interior paint and new flooring flow seamlessly throughout the home, complemented by energy-efficient LED lighting, new ceiling fans and updated bathroom vanities for a clean, modern, and cohesive design. Primary bedroom with two walk in closets, separate dressing area and walk in shower with glass door in primary bathroom. Guest bedroom with wall closets. Washer and dryer are located in closet off hall near guest quarters. Generous storage and ample closet space add to the home’s functionality and overall comfort. Enjoy the added privacy of a second-floor location while taking advantage of the exceptional lifestyle within the East Lake community. The community pool and Condo 2 Clubhouse is just across the parking lot! Pets are welcome and the monthly maintenance fee provides an outstanding value and ease of living. If you are ready to explore, the location of the condo is fantastic - starting with the nearby community heated pools (two of them) or visit/join Ardea Country Club that offers two 18 hole golf courses, their own pools, tennis, pickleball, fitness center, Clubhouse, restaurants and activities. Your condo is an easy commute to Westfield Countryside Mall, area shopping, various restaurants and entertainment plus the sandy beaches of Honeymoon Island along with local parks and walking trails for your low stress lifestyle. More dining and shopping in the surrounding downtown areas of Tarpon Springs, Dunedin and Safety Harbor.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Karen Sewell (727-542-4467)
1502 WOODSTREAM DR, OLDSMAR, FL 34677
$689,000242 Days on yellowkey MLS ID: TB8428089
2 Days Off yellowkey (back on 4/17/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2234 Built: 1996Monthly Fee: $470 Tax: $5,116 (2024)Community: Cross Creek - Unit TwoSingle Family
Taxes:$5,116
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Welcome to this exceptional, move-in ready home in Cross Creek, located within the gated, golf community of East Lake Woodlands. Boasting a most desirable, one-story floor plan with 2,234 sq. ft. interior, this residence features 3 bedrooms plus an office or den, 2 full baths, and a spacious 2-car garage. Enjoy a great combination of low maintenance convenience and the privacy of a single family home with gorgeous conservation and water views. This inviting residence welcomes you with beautiful hardwood flooring, high ceilings, plantation shutters and an open great room plan that flows seamlessly from the updated kitchen into the living space. The kitchen features a bright eat-in breakfast area with bay windows and showcases tile floors, crisp white cabinets, gleaming granite countertops, stainless steel appliances and large pantry. The primary suite offers a luxurious, updated bathroom with dual vanities accented with granite, massive walk-in shower, gorgeous tile floors and 2 closets. Pocket doors provide open access to the den to wake up to those peaceful water views or to enjoy a cozy setting ideal for reading or watching television. Two additional bedrooms are located on the other end of the home and are generously sized with ample closet space and a guest bath with attractive vanity with granite and soft neutral tones. Step outside from glass sliders in the great room or den to the seamless outdoor retreat with stunning pavered lanai with your own private, sparkling pool overlooking that serene scenery — perfect for relaxing! Enjoy the outdoors with both covered and open lounging areas, all within a screened enclosure and offering fantastic water views. Long-time owner has had no issues with storms. Updates include a new roof in 2019, water heater (2019) and 4-ton A/C unit (2019). A dedicated laundry room comes complete with plenty of storage, deep tub sink and washer and dryer included in the sale. Relax knowing the HOA fee covers lawn maintenance, trimming and mulching, basic cable TV and internet, trash and recycling collection, access to community pool and spa, pressure cleaning of roofs and even exterior painting every 7 years! In addition, there are a variety of optional memberships to choose from for the recently-renovated Ardea Country Club with 2 golf courses, fitness center, heated lap pool and freeform pool, poolside café, pickleball and tennis, dining and events. All this in a great location convenient to Tampa International Airport, beautiful beaches, medical facilities, parks, professional sporting events and more.
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Claudia Tweed (727-433-4596)
122 CARYL WAY #122, OLDSMAR, FL 34677
$214,00085 Days on yellowkey MLS ID: TB8481510
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1979Monthly Fee: $560 Tax: $2,781 (2025)Community: East Lake WoodlandsCondo
Taxes:$2,781
Remarks: Move right into this beautifully updated first-floor condo located in the highly desirable gated community of East Lake Woodlands in Oldsmar. Offering comfort, convenience, and low-maintenance living, this bright and inviting home features abundant natural light and a functional open layout perfect for everyday living. The home includes an updated kitchen with modern cabinetry and stainless steel appliances, along with fresh interior paint and ceramic tile flooring throughout for a clean, modern feel. Hurricane impact windows provide added safety and energy efficiency, while elegant French doors from the living room open to the patio, allowing for seamless indoor-outdoor living and plenty of natural light. Ample closet space and additional storage add to the home's comfort and functionality. This pool-facing unit offers convenient access to the community pool, creating a relaxing setting just steps from your door. Residents also enjoy nearby championship golf courses, along with optional clubhouse membership that provides additional amenities, dining, and social activities. The HOA fee includes water, trash, cable, and internet, making ownership both simple and cost-effective. Conveniently located close to shopping, restaurants, parks, Gulf beaches, and major commuting routes, this property is ideal as a primary residence, seasonal home, or investment opportunity. Don't miss your chance to own in one of Oldsmar's most sought-after gated communities - schedule your showing today.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Mo Khan (954-998-3336)
120 BRENT CIR, OLDSMAR, FL 34677
$520,00068 Days on yellowkey MLS ID: TB8484780
0 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 1834 Built: 2004Monthly Fee: $473 Tax: $8,930 (2025)Community: Seaside EstatesTownhouse
Taxes:$8,930
Elementary School: Oldsmar Elementary-PN
Remarks: Under contract-accepting backup offers. Are you dreaming of your own stylish urban OASIS surrounded by nature yet minutes from everywhere you want to be? Experience effortless coastal living in this exceptional waterfront townhome, perfectly designed for those who appreciate space, light and direct access to the water. Featuring two private boat slips, this residence offers a RARE opportunity to keep your vessels close and enjoy days on the water at a moment's notice. Inside, the home unfolds into an open, light-filled floor plan enhanced by soaring high ceilings and expansive windows that invite natural light throughout the day. The seemless flow between living, dining, and kitchen spaces creates an ideal setting for both RELAXED everyday LIVING and entertaining. Water views provide a constantly changing backdrop, adding a sense of CALM and CONNECTION to the outdoors. The generous layout offers flexibility for hosting family and guests, while the airy ceiling heights add architectural drama and a sense of openness rarely found in townhome living. Whether you're enjoying quiet mornings with coffee by the water or gathering with friends after a day on the boat, this home adapts effortlessly to your lifestyle. Outdoor living is just as compelling, with immediate access to the waterfront and your own boat slips just steps away - perfect for boating, paddleboarding, or sunset cruises. This is a home that blends convenience and luxury, offering the maintenance ease of a townhome with the experience of a private gated waterfront retreat. Ideally suited as a primary residence or a refined second home, this property delivers the best of waterfront living - space, light, and direct access to the water- all in one elegant package.
Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)
Listing Agent: Darren Booth (813-310-0196)
112 CYPRESS CT #112, OLDSMAR, FL 34677
$189,90052 Days on yellowkey MLS ID: TB8494664
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980Monthly Fee: $587 Tax: $2,592 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Taxes:$2,592
Remarks: Welcome to 112 Cypress Ln in the highly sought-after East Lake Woodlands / Cypress Estates community in Oldsmar. This charming 2-bedroom, 2-bath condo offers comfortable Florida living in a peaceful, gated setting with access to a community pool and beautifully maintained grounds. The home features a functional split floor plan, in-unit laundry, and a private screened patio — perfect for enjoying your morning coffee or unwinding in the evenings. Residents of East Lake Woodlands enjoy access to a range of community amenities, including a clubhouse, golf course, tennis courts, and multiple pool areas, creating a resort-style living experience right in your neighborhood. Ideally located just minutes from shopping, dining, entertainment, and major roadways, this property provides easy access to Clearwater, Tampa, St. Petersburg, and the Gulf Coast beaches. Oldsmar is known for its parks, community events, and convenient lifestyle, making this an excellent option for full-time residents or seasonal living. Property is also available for lease or lease option.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Wil Sanders (813-380-6048)
1598 LOCKMEADE PL, OLDSMAR, FL 34677
$999,90064 Days on yellowkey MLS ID: TB8490836
2 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3300 Built: 1995Monthly Fee: $243 Tax: $8,700 (2025)Community: Aberdeen Unit TwoSingle Family
Taxes:$8,700
Remarks: Under contract-accepting backup offers. Exquisite Estate Home in the Prestigious Aberdeen Enclave of East Lake Woodlands...Located within the highly sought-after, gated community of East Lake Woodlands and the exclusive Aberdeen enclave, this beautifully appointed residence offers refined living in one of the area’s most desirable neighborhoods. Positioned on an oversized 0.33-acre cul-de-sac lot, this approximately 3,300-square-foot home blends timeless elegance, quality craftsmanship, and thoughtful design. The home welcomes you with a dramatic two-story foyer featuring a sweeping volute staircase with wood spindles. Elegant black and white Carrera marble harlequin tile flooring enhances the entry and formal dining room, while rich 8-inch distressed hickory flooring flows through the kitchen and family room. The spacious layout offers 4 bedrooms plus a dedicated study/den, 3 full bathrooms, and 1 half bath. Oversized upstairs bedrooms provide comfortable accommodations for family and guests. For added protection and efficiency, the home also features 12 newly installed impact windows across the front of the home and in all three upstairs bedrooms, providing enhanced storm protection, energy efficiency, and peace of mind. At the center of the home is a gourmet kitchen designed for both everyday living and entertaining. Features include granite countertops, a solid wood center island, custom Ash wood cabinetry, stainless steel appliances, and a Monogram four-burner gas range with griddle and vent hood. A large walk-in pantry and counter-height breakfast bar add convenience, while a stylish built-in mini bar with a wine cooler enhances the home’s entertaining appeal. A two-sided gas fireplace connects the kitchen and family room, creating a warm and inviting atmosphere. The luxurious primary suite serves as a private retreat with sliding doors opening to the patio. A grand gas fireplace with a custom mantel adds character, while the spa-inspired bathroom features dual vanities, a private water closet, a walk-in shower with dual showerheads, and a stunning clawfoot soaking tub positioned in a bay window beneath a chandelier. Expansive walk-in closets with custom built-ins complete the suite. Outdoor living is equally impressive. The backyard showcases an oversized pool with automation, solar heating, and a spillover spa with optional propane heating. Travertine pavers surround the pool area, and the covered screened patio provides multiple seating and entertaining spaces. Mature landscaping and decorative accent planters create a private resort-style setting. The irrigation system utilizes reclaimed water. Additional highlights include a barrel tile roof (2013), brick-paver driveway, oversized three-car garage, large laundry and mudroom, updated HVAC systems with UV lights (2016 and 2019), a water softener system, and a 100-gallon propane tank serving the pool, spa, and range. Most solar panels have been replaced within the past four years, and the exterior was freshly painted in 2017. This exceptional property offers a rare combination of elegance, space, and modern updates in a premier gated community. Conveniently located near top-rated schools, golf, shopping, and dining, it provides the ideal setting for both everyday living and entertaining. Schedule your private showing and experience everything this remarkable East Lake Woodlands home has to offer.
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Nancy Leslie (727-789-5555)
347 CANAL WAY, OLDSMAR, FL 34677
$199,000224 Days on yellowkey MLS ID: TB8436926
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1080 Built: 1980Monthly Fee: $60 Tax: $2,609 (2024)Community: Gull-Aire VillageMobile Home
Taxes:$2,609
Remarks: HUGE Price DROP!! Welcome to Gull-Aire Village, a 55+ PET-Friendly and Golf Cart Friendly community in the Heart of Oldsmar! Gull-Aire Village is a Land-Owned community, meaning YOU OWN THE LAND! not just the home. A Very unique property with No rear neighbors. This home comes FULLY FURNISHED! and Features A NEWER ROOF (only 3yrs Old) Newer WINDOWS and Doors, New Flooring(2025) and Vapor Barrier (2025) New Water Heater(2025) Newer AC(2022) Newer Samsung Washer and Dryer(2024) This 2-bedroom, 2-bath home is situated on a serene canal view lot and offers the perfect blend of comfort, convenience, and Florida charm. Inside, you'll find a bright and spacious living area, a functional kitchen with plenty of cabinet space, and a screened Florida room where you can relax and enjoy peaceful water views. Split bedroom plan, the primary bedroom features an En-Suite bath, and one additional bedroom for guests, hobbies, or a home office. Beautifully landscaped. Air conditioned Florida room that is not included in the square footage 14 x15. Additional glass enclosed porch on rear of home 10 x14. Good sized utility too. With a Low-cost monthly HOA fee of Only $60 a month, it’s an affordable option for those seeking an active lifestyle. Community amenities include a Heated Pool, Spa, Active Clubhouse with a Library and Pool Table, Shuffleboard courts, Bocce ball court and a calendar of Social Events. Just cross the street and there are wonderful Restaurants, Shopping, and a movie theater! You can walk to AMC theatres, Beall’s, Marshall’s, Dollar Store and Restaurants. Just minutes to Westfield Mall, Target, a Super Walmart, Publix and Countryside Hospital. A walking/running/biking trail is located adjacent to Canal Way, which takes you directly to picturesque Sheffield Park, which is a lovely place with trails to walk, play disc golf, PICKLEBALL, or go to the Dog Park. There is also a playground for the grandkids. You can walk along the path of the Tarpon outfall canal, on the west edge of Gull-Aire Village, and enjoy all the Florida wildlife, including the occasional Manatee sighting. Very Close to Dunedin and Safety Harbor! Less than 30mins to Tampa International Airport. Only 20 minutes to Honeymoon Island Beach and Caladesi State Parks. Come Enjoy the Florida Life-Style with this Low Maintenance home!!
Listing Agent: Asher Walli (727-744-7466)
2270 CHRISTY LN, OLDSMAR, FL 34677
$1,250,000100 Days on yellowkey MLS ID: TB8477474
2 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3993 Built: 1996Monthly Fee: $181 Tax: $11,849 (2025)Community: Turtle Creek Unit-ThreeSpa: YesSingle Family
Taxes:$11,849
Remarks: Under contract-accepting backup offers. Welcome to luxury living in the desirable Gated, Golf Community of East Lake Woodlands! This stunning home in Turtle Creek has a Premium Conservation Setting and features 4 Bedrooms plus Office/Den and Bonus Room, 4.5 Baths all on One-Story with the exception of the bonus room. Perfectly nestled on a picturesque Cul-de-Sac, tranquility and privacy are yours. Enjoy the best of both worlds with a serene, fenced back yard that’s easy to maintain while having the privacy of Deep Conservation beyond on this Expansive 1.95-acre lot. Plus this home is located in the preferred Zone X so No flood insurance is required! The wide Side Load Garage measuring 28’ x 22’ and large Pavered Driveway provide generous parking and set the tone for a stately entrance accented with Travertine along front and side. Step inside to Open Living Room and Dining Room elegance with Soaring Volume Ceilings, Stunning Crown Molding and Dramatic Windows that create an inviting ambiance. Flexibility abounds with this Floor Plan with the Office/Den and Bonus Room providing plenty of options to best fit your family’s needs now and in the future. And the Three-way Split bedroom layout gives everyone their own space. Need a 5th Bedroom? No problem, the front Office/Den is generously sized and features a closet plus gorgeous windows. The Open Concept continues to the Kitchen and Family Room ideal for entertaining small or large gatherings of family and friends. Stainless Steel Appliances including Oversized Fridge, Gas Range and loads of Storage highlight this kitchen in addition to its large Center Island with Prep Sink, Walk-In Pantry and Breakfast Bar for lots of seating. Retreat to the luxurious Primary Suite which occupies the entire right wing of the home and includes an Additional Sitting Area complete with Cozy Gas Fireplace and a Spa-like Primary Bathroom with long Dual Vanity, Deep Soaking Tub and all Neutral Creamy Tones - your personal oasis. This home also boasts a convenient shared bathroom for bedrooms 2 and 3 plus another separate 4th bedroom and bath. Outdoor Living and all that privacy is accentuated with the Gorgeous Pool and Spa with Electric and Gas Heaters respectively, impressive Covered and Screened Lanai and Extensive Pavers which carry through to the side walkway spanning the length of the home. Upgrades include Tankless Water heater installed in 2026, New Trane A/C for main portion of the house in 2021, Bosch Dishwasher in 2025, Electric Pool Heater in 2021, Reverse Osmosis System, Tile Roof in 2013, Aluminum Fencing and Mini-Split A/C in Garage. Plus 2023 Samsung Washer and Dryer are included in the sale. Relax and take advantage of Optional Memberships to Ardea Country Club including Resort-Style Amenities such as 2 Golf Courses, Fitness Center, Heated Lap Pool and Freeform Pool, Poolside Café, Pickleball and Tennis, Dining and a host of Events. Located conveniently to Tampa International Airport, Top-rated schools, Beautiful Beaches, Medical Facilities, Parks and Outstanding Dining, this exceptional home offers the perfect blend of Luxury, Convenience and Lifestyle. Don’t miss your opportunity to own this East Lake Woodlands gem!
112 BRENT CIR, OLDSMAR, FL 34677
$499,000144 Days on yellowkey MLS ID: TB8461018
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 1834 Built: 2004Monthly Fee: $473 Tax: $4,946 (2025)Community: Seaside EstatesTownhouse
Taxes:$4,946
Remarks: PRICE IMPROVEMENT! LUXURY MEETS UNBEATABLE VALUE. Skip the rehab and move right in to the most updated waterfront townhome in the gated community of Seaside Estates. This beautifully maintained three-story home radiates pride of ownership and offers three bedrooms, three bathrooms, and over 1,800 square feet of thoughtfully designed living space. Premium features include IMPACT WINDOWS, IMPACT SLIDERS, and PLANTATION SHUTTERS, providing extra security, energy savings, and a whisper-quiet interior. Inside, this immaculate townhouse shines with high ceilings, skylights, an open-concept layout, luxury waterproof flooring, and modern updates in the kitchen and all three bathrooms. The inclusive HOA fee covers your roof (replaced in 2017), water, sewer, trash, and fire sprinklers, making this one of the most affordable and low-maintenance lifestyles available. The DEEDED SLIP is perfect for kayaks, jet skis, or a flats boat. Complete with a new AC (2023), 3-car garage, and resort-style pool/spa/tennis, every detail is covered. Located in the heart of Oldsmar, you’ll enjoy easy access to all the best of the Tampa Bay area, including sparkling Gulf Coast beaches, Tampa International Airport, Westshore, Clearwater, and Tampa/St Pete. You’re also just steps away from R.E. Olds Park, a 15-acre waterfront park with the city pier, amphitheater, playgrounds, trails, beach volleyball and more. Whether it’s your primary residence or Florida getaway, this waterfront gem delivers the lifestyle you’ve been waiting for. Schedule your showing today!
Listing Agent: James Wheeler, Pa (813-285-1229)
108 DOLPHIN DR E, OLDSMAR, FL 34677
$319,00087 Days on yellowkey MLS ID: TB8482185
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1372 Built: 1982Monthly Fee: $70 Tax: $2,959 (2025)Community: Gull-Aire VillageManufactured Home
Taxes:$2,959
Remarks: The Prettiest Home in Gull Aire – Turn-Key Perfection! Welcome to the crown jewel of Gull Aire, widely considered the most beautiful home in the entire community. This meticulously renovated 3-bedroom, 2-bathroom residence has been reimagined inside and out to offer the perfect blend of modern luxury and cozy community charm. If you are a social-seeking senior looking for a vibrant lifestyle in a golf-cart-friendly neighborhood, your search ends here. Step across the delightful front porch, which serves as your new favorite spot for morning coffee and easy socialization with passing neighbors, and into an interior that feels brand new. Luxury vinyl plank flooring flows seamlessly throughout the entire open floor plan, leading you into a living room anchored by a stunning built-in electric fireplace that acts as the ultimate focal point for cozy evenings. Have plenty of space for guests with a rare third bedroom that can serve as an office. The heart of the home is a chef’s dream kitchen featuring an expansive central island perfect for baking, crafting or entertaining. This upgraded space boasts premium finishes, modern appliances, and abundant storage, along with a unique laundry pass-through that adds effortless convenience to your daily routine. Beyond the doorstep, Gull Aire Village offers resort-style living with remarkably low HOA fees. You will enjoy access to the sparkling community pool and a clubhouse packed with amenities, all easily accessible by golf cart. This turn-key, move-in ready home is perfectly positioned in close proximity to top-tier shopping, local dining favorites, and endless entertainment options. This is more than just a house; it is a total lifestyle upgrade waiting for its next owner.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Jackie Little (813-453-8960)
375 WELLINGTON AVE, OLDSMAR, FL 34677
$1,299,00056 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
Taxes:$14,951
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 Agent: Jenny Neumeyer (727-482-2656)
465 HOLLY HILL RD, OLDSMAR, FL 34677
$650,00074 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!
416 COUNTRY CLUB DR, OLDSMAR, FL 34677
$385,000104 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)
2044 SHEFFIELD CT, OLDSMAR, FL 34677
$190,000539 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)
380 WELLINGTON AVE, OLDSMAR, FL 34677
$1,155,000413 Days on yellowkey MLS ID: TB8373443
Bed: 4 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 3420 Built: 1992 Tax: $6,112 (2024)Community: Country Club Add To Oldsmar RevSingle Family
Taxes:$6,112
Remarks: PRICE REDUCTION! Now priced below value, this is your chance to own this incredible Key West style pool home on an oversized conservation lot in highly desirable Oldsmar. Located on a cul de sac with no through traffic on nearly an acre of land, with lush tropical landscaping backing up to forested conservation for added privacy. At the main entry is an inviting wraparound porch. Step inside the welcoming foyer to a soaring vaulted ceiling in the great room, which also features a wood burning fireplace and two sets of French doors leading to screened back porches and beyond to a huge rear deck that spans the length of the house and overlooks the large free form pool and spa. The primary suite has two walk-in closets and a remodeled bathroom (2023) with two vanities, a whirlpool tub, tiled walk-in shower, and water closet. The remodeled gourmet kitchen (2022) features stainless steel appliances, Viking dual fuel range with pot filler and vent hood, quartz counters, plentiful cabinetry, and a large island with wine fridge and copper top (durable and naturally anti-microbial/anti-bacterial). Off the kitchen is a half bathroom, a laundry room with utility sink and extra pantry storage, and a wet bar/coffee nook with even more pantry storage. Upstairs are two spacious bedrooms, a loft/office area, and updated hall bathroom (2023). At the top of the house is a railed rooftop platform offering stunning views out to Tampa Bay. The ground floor features covered parking for at least 4 vehicles, spacious storage/workshop areas, and a garage apartment/in-law suite with a bedroom, living/game room, kitchenette, and full bathroom. The circular driveway, side driveway, and large parking pad provide abundant parking for guests, boats, RV, etc. No HOA or CDD. Oldsmar is a waterfront golf cart community known for wonderful parks, quality of life, A rated schools, and convenient access to Tampa International Airport, Gulf beaches, shopping, dining, and more. Schedule your private showing today! As an added bonus, the seller has an assumable government loan at just 2.75%! Call agent for details.
115 WINDWARD PL #15, OLDSMAR, FL 34677
$180,00062 Days on yellowkey MLS ID: TB8490824
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 879 Built: 1984Monthly Fee: $431 Tax: $2,768 (2025)Community: Meadows Condo At East Lake WoodlandsCondo
Taxes:$2,768
Remarks: LOCATION, LOCATION, LOCATION! Close to entertainment, shopping, restaurants, airports, and world-famous beaches, this beautiful ground floor, end unit condo is waiting for you! Located in the highly desirable, gated community Meadows of Eastlake Woodlands, this home has it all! Gorgeous granite countertops highlight the kitchen as does the impressive cabinet space and closet pantry. The inviting open living space makes time together comfortable, yet the split bedroom floor plan offers privacy when needed. The primary bedroom is generous and offers two walk-in closets, an ensuite bath with step-in shower, and patio access. HVAC 2021. The HOA fees include water, sewer, trash, cable, community pool, exterior maintenance including the roof, and grounds maintenance. There is a community golf course that owners may access for an additional fee.
Listing is courtesy of: FLORIDA PREMIERE REALTY (727-437-0261)
Listing Agent: Millie Jackson (828-337-9468)
209 HEMINGWAY DR, OLDSMAR, FL 34677
$294,90084 Days on yellowkey MLS ID: TB8483445
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1086 Built: 1997Monthly Fee: $240 Tax: $672 (2024)Community: Sun Ketch Twnhms At Cypress LakesTownhouse
Taxes:$672
Remarks: Stunning Sun Ketch Townhome | Bright, Airy & Move-In Ready! Welcome to your slice of paradise in the highly sought-after Sun Ketch community of Oldsmar! This meticulously maintained 2-bedroom, 2-bathroom townhome offers the perfect blend of style, comfort, and convenience. Step inside to find gorgeous, rich cherry floors that flow through the living spaces, adding warmth and a touch of luxury through out. Large sliders, skylights and a thoughtful layout ensure the entire home feels light-filled and spacious. It is exceptionally clean and move-in ready. This unit includes a one-car garage perfect for parking, extra storage, or a home hobby space. Outdoor Living: Enjoy the Florida sunshine at the beautiful community pool, just a short stroll from your front door. Located in the heart of Oldsmar, you’re minutes away from restaurants shopping, scenic waterfront parks, walking trails, 2 airports and easy commutes to both Tampa and the Gulf beaches. Live the easy life in a community known for its charm and quiet atmosphere.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (813-839-3800)
Listing Agent: Melissa Hinchliffe (813-928-0269)
358 LAKE WAY, OLDSMAR, FL 34677
$259,90077 Days on yellowkey MLS ID: TB8486181
1 Days Off yellowkey (back on 3/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1998Community: Gull-Aire VillageManufactured Home
Taxes:
Tax Year:
Remarks: Welcome to 358 Lake Way in Gull-Aire Village, a desirable 55+ active golf cart community in Oldsmar where you own the land and enjoy a low $70/month HOA. This beautifully maintained 1998 Jacobson home offers 3 bedrooms, 2 bathrooms, and 1,296 sq ft of heated living space with over $40,000 in upgrades and improvements completed since 2023. Step inside to a bright and inviting interior featuring refinished hardwood floors throughout the living room, dining room, kitchen, and hallway, along with new carpet in the bedrooms. The home has been extensively refreshed with popcorn ceilings removed, modern orange peel wall and ceiling texture, and fresh interior paint throughout all walls and doors. Updated lighting fixtures, new electrical switches and outlets, and five remote-controlled ceiling fans enhance comfort and style. The updated kitchen offers abundant cabinetry, ample counter space, and a breakfast bar, along with new LG stainless steel appliances including a double oven range, French door refrigerator with craft ice, dishwasher, vent hood, and microwave. The countertops were refinished with spray epoxy for a fresh modern look, and six recessed can lights were added to brighten the space. The home features a split bedroom floor plan for privacy. The primary suite includes a barn door entry to the en-suite bathroom and updated lighting. Both bathrooms have been refreshed with new faucets, new toilets, fresh paint, and new exhaust fans. Additional upgrades include interior shutters, new interior door hardware, lighting added in the primary closet and laundry closet, and a rebuilt sliding glass door. Enjoy Florida living in the front porch / Florida room with acrylic windows and new exterior screening, providing a comfortable space to relax year-round. Outside you will find new landscaping with decorative granite rock and an additional custom storage shed installed behind the home. Major updates include: New roof (2025), New hot water heater (2026), New double pane windows (2023), Hardwood floors sanded and refinished (2023), and New bedroom carpet (2023). The heat pump (2013) has been professionally serviced every six months and had minimal prior use by the previous snowbird owner. Average utility costs are approximately $135/month for electric and $80/month for water. Residents of Gull-Aire Village enjoy an active community lifestyle featuring a clubhouse, heated pool and spa, shuffleboard courts, bocce ball, library, billiards, and social activities. The community is conveniently located near shopping, dining, and entertainment with grocery stores, restaurants, and retail within walking distance. Just minutes away are Countryside Mall, Publix, Walmart, and Countryside Hospital, with an easy commute to Tampa International Airport. The award-winning Gulf beaches of Honeymoon Island and Caladesi Island State Park are approximately 20 minutes away. This property qualifies for conventional and FHA financing, and the seller is offering a 1-year home warranty for the buyer. The home sits on a 50 x 80 lot with boundary markers in place.
Listing is courtesy of: THE SOMERDAY GROUP PL (813-520-9123)
Listing Agent: Carmine Petruzziello (516-838-0038)
108 LAKEVIEW PL #108, OLDSMAR, FL 34677
$179,900172 Days on yellowkey MLS ID: TB8454159
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1980Community: East Lake Woodlands CondoCondo
Remarks: Under contract-accepting backup offers. Discover the perfect blend of luxury and convenience in this beautifully updated second-floor condo, located in the prestigious guard-gated East Lake Woodlands golf community. Enjoy serene water views and modern upgrades, including luxury vinyl plank flooring, quartz kitchen countertops, and a fully remodeled master bath—ready for you to move in and start living the Florida dream. Enhance your lifestyle with optional memberships at the newly renovated Ardea Golf Club, offering championship golf, tennis, and vibrant social events. Just steps away, you’ll find Boot Ranch shopping center with Publix and Target, plus private gate access to Walmart Neighborhood Market. Outdoor enthusiasts will love nearby John Chesnut Park on Lake Tarpon and the award-winning beaches of Honeymoon Island State Park, only minutes away. This is more than a home—it’s a lifestyle. Don’t miss your chance to own a piece of paradise in one of North Pinellas County’s most sought-after communities!
Listing Agent: Mark Clark (727-458-3765)
1712 AZALEA CT #A, OLDSMAR, FL 34677
$369,900336 Days on yellowkey MLS ID: TB8401279
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1360 Built: 1977 Tax: $2,831 (2024)Community: Harbor Palms-Unit Four ASingle Family
Taxes:$2,831
Remarks: Welcome to 1712 Azalea Court A in the heart of Oldsmar — a hidden gem just minutes from world-class beaches, top-rated golf courses, and some of the best attractions Tampa Bay has! This beautifully maintained home offers the perfect blend of comfort and convenience, nestled on a quiet cul-de-sac with no rear neighbors. Whether you’re looking for a full-time residence, vacation home, or income-producing property, this is a fantastic investment opportunity. Currently operating as a successful Airbnb, this home is turn-key ready to generate immediate cash flow. Don’t miss your chance to own a piece of Florida paradise! (Please also see photos of the nearby attractions of the Tampa Bay Area)
Listing is courtesy of: CALEBRO & ASSOCIATES (813-996-2500)
Listing Agent: Bert Calebro (813-294-9703)
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