Location: Oldsmar , 34677
Do Not Show Listings
134 CYPRESS CT #134, OLDSMAR, FL 34677
$139,90058 Days on yellowkey MLS ID: TB8484548
REDUCED by $10,100 (6.7%) on 05/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980 Tax: $3,044 (2025)Community: East Lake Woodlands Cypress EstatesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,044
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
Remarks: One or more photo(s) has been virtually staged. ***MOTIVATED SELLER***Welcome to easy Florida living in the peaceful Cypress Estates III neighborhood, located in the highly sought-after East Lake Woodlands gated golfing community. This light-filled two-bedroom, two-bath condo offers low-maintenance living with Condo fees that cover water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and the community pool. Your second-floor unit is just a short stroll from your assigned parking space, making everyday living convenient and accessible. Step inside and you’re greeted by an open and inviting living, dining, and kitchen area designed for both comfort and entertaining. Natural light flows throughout the space, highlighting the updated flooring that extends across the entire home. Sliding glass doors lead you out to a screened-in lanai, the perfect place to start your morning with coffee or unwind in the evening while enjoying tranquil conservation views nearby. The lanai also features a convenient laundry closet along with additional storage space. Tucked toward the rear of the home, the spacious primary suite provides a peaceful retreat. It features two generous walk-in closets, private sliding door access to the lanai, an oversized linen closet with extra storage, and an en-suite bathroom complete with a step-in shower. Back near the main living area, the kitchen offers ample cabinetry, a range, refrigerator, and dishwasher, a pantry closet with shelving to keep everything organized, and space for a table. Just around the corner, the hallway includes a linen closet, along with a second full bathroom featuring a tub and shower combination located conveniently across from the second bedroom. The second bedroom is well-sized and includes an oversized wall closet providing excellent storage. Quietly situated within this desirable community, this bright and welcoming condo offers comfort, convenience, and a lifestyle that’s hard to beat. With updated flooring already in place, all that’s left to do is move in and make it your own. Cypress Estates has a community pool that is only a short distance from your new home. Located in close proximity to shopping and restaurants, with easy access to Tampa and the beaches, this home is ready for its new owner! Come see this property today and experience the charm of East Lake Woodlands.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Vanessa Leonard (727-647-2706)
4738 PEBBLE BROOK DR, OLDSMAR, FL 34677
$535,000124 Days on yellowkey MLS ID: TB8460875
2 Days Off yellowkey (back on 5/7/2026)
REDUCED by $14,000 (2.6%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1938 Built: 1996Monthly Fee: $470 Tax: $4,041 (2025)Community: Cross Creek - Unit TwoSingle Family
Taxes:$4,041
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy a Relaxing Lifestyle in the desirable Gated, Golf Community of East Lake Woodlands and the convenience of Less Maintenance responsibilities! This home provides Privacy and Stunning Water Views with a Large, Covered Screened Lanai to enjoy that morning cup of coffee or evening glass of wine. Plus it’s situated in the preferred Zone X so no flood insurance is required. An added bonus is the Cul de Sac location and longer driveway for more parking for family and guests. Volume Ceilings, Crown Molding and an Open Concept highlight a versatile floor plan featuring 2 Bedrooms plus an Office or Den - complete with Custom Paneling, Spacious Desk and Bookcase and even the Luxury of a Wood Burning Fireplace! Open to the generous 28’ x 18’ Great Room, the bright Kitchen features an Eat-In Breakfast Area, Bay Windows with Plantation Shutters, Double Ovens, French Door Fridge and plenty of storage. The Primary Suite features 2 Walk-In Closets complete with Custom Built-in Shelving and Pull-Down Clothing Racks and a Large Bath with Dual Vanities, Large Soaking Tub and Separate Shower. Relax since the reasonable HOA fee includes Lawn Maintenance with Mowing, Fertilizing and Mulching, Cable TV and Internet, Trash and Recycling Collection, a Sparkling Community Pool and Spa for Cross Creek residents, Escrow Reserves, Pressure Cleaning of Roofs and Exterior Painting every 7 years. Home Updates include New Water Heater in Dec. 2025, New Tile Roof in 2019, A/C Unit New in 2018. Washer and Dryer included in the sale plus Manual and Remote-Controlled Exterior Hurricane Shutters and a Generac Generator. This long-time owner had no issues with the 2024 Hurricanes. Enjoy that Gorgeous View and put your touches on this home since this amazing price takes updating into account. All this in a Great Location convenient to Tampa International Airport, beautiful Beaches, Medical Facilities, Professional Sporting Events and Fine Dining. A variety of memberships to Ardea Country Club are available for additional fees and include access to 2 Golf Courses, a Fitness Center, Heated Lap Pool and Freeform Pool, Pickle Ball and Tennis plus Dining and a host of Activities and Events!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Claudia Tweed (727-433-4596)
101 DOLPHIN DR N, OLDSMAR, FL 34677
$225,000182 Days on yellowkey MLS ID: TB8444809
REDUCED by $19,900 (8.1%) on 05/07/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1573 Built: 1989Monthly Fee: $70 Tax: $582 (2024)Community: Gull-Aire VillageSpa: NoManufactured Home
Taxes:$582
Elementary School: Oldsmar Elementary-PN
Tax Year: 2024
Remarks: Welcome Home! Your move-in ready and partially furnished Florida retreat with a warm, contemporary flair awaits you in the heart of Oldsmar. This spacious 2-bedroom, 2-bath home is situated on a rare DOUBLE LOT (7,854 sq. ft.), that YOU OWN offering privacy and flexibility. The open and inviting floor plan features cathedral ceilings and newer laminate flooring throughout the family room, kitchen, laundry room and hallway. The kitchen is well-appointed with a spacious island/snack bar, newer refrigerator and a convenient pantry closet - perfect for entertaining. The generous primary suite includes access to the over sized (10.75' x 31') enclosed Florida room, a walk-in closet, an en-suite bath with a walk-in shower and relaxing garden tub. The Florida room features glass windows overlooking the beautifully landscaped backyard and provides an ideal space for entertaining or just enjoying Florida's indoor-outdoor lifestyle! More recent updates include a newer A/C system (2020), a spacious 2 car garage with a large workshop with ample storage space (2003) and a newer high-quality sliding glass door. Nestled in the highly desirable 55+ community of Gull-Aire Village, this golf cart-friendly neighborhood offers exceptional resort-style amenities, including a spacious clubhouse, large, heated pool and spa, library, enclosed shuffleboard court, bocce ball court, and an active calendar of social events and activities. This home sits on land you own and features a low monthly HOA fee of just $70 with one pet of any size permitted. The location is truly unbeatable! You're less than a mile from Woodlands Square, offering Bealls, Marshall’s, Ulta, PetSmart, AMC Theatres, Craft Street Kitchen, Shaker & Peel, Eve’s Family Restaurant, and more. Everyday conveniences such as Publix, Target, Walmart Neighborhood Market, and Mease Countryside Hospital are just 2 miles away. Honeymoon Island Beach is approximately 9 miles away, and Tampa International Airport is a easy 15-mile drive. An adjacent walking, running, and biking trail along Canal Way leads directly to picturesque Sheffield Park, providing the perfect setting to enjoy Florida’s outdoor beauty. Whether you’re socializing at the clubhouse, relaxing by the sparkling pool, or simply enjoying the peaceful surroundings, you’ll fall in love with the friendly, welcoming lifestyle of Gull-Aire Village. (Room dimensions are approximate and should be verified by Buyer.)
Listing is courtesy of: AH REALTY SERVICES, LLC (727-275-3512)
Listing Agent: Anne Hode (813-545-1960)
1204 FORESTWOOD DR, OLDSMAR, FL 34677
$315,00015 Days on yellowkey MLS ID: O6402042
0 Days Off yellowkey (back on 5/7/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1186 Built: 1984Monthly Fee: $35 Tax: $2,622 (2025)Community: Hamlets Of Forest Lakes TheSpa: NoSingle Family
Taxes:$2,622
Remarks: Picture yourself at 1204 Forestwood Dr, a residence recently refreshed with fresh interior paint and new appliances throughout. A cozy fireplace adds comfort, complementing the kitchen's all stainless steel appliances. The exterior features a covered patio that extends to a fully fenced in backyard. Ready to enjoy stylish updates and outdoor living. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
413 COUNTRY CLUB DR, OLDSMAR, FL 34677
$379,90036 Days on yellowkey MLS ID: O6396122
REDUCED by $5,000 (1.3%) on 05/07/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1323 Built: 1959 Tax: $3,829 (2024)Community: Oldsmar Country Club Estates Sec 2Single Family
Taxes:$3,829
Remarks: Welcome to this stunning, fully renovated 3-bedroom, 2-bathroom waterfront home located in the highly desirable Oldsmar Country Club Estates. Situated on a spacious 0.21-acre lot with no HOA, this property offers a rare opportunity to enjoy true Florida living with direct water access. Follow the scenic water trail right from your backyard all the way out to Tampa Bay, making this a dream for kayaking, paddleboarding, and outdoor enthusiasts. From the moment you arrive, you’ll be drawn in by the beautiful curb appeal, manicured landscaping, and inviting exterior. Inside, luxury vinyl tile flooring flows throughout the home, complemented by an open, modern layout filled with natural light. The renovated kitchen features stainless steel appliances, quartz countertops, and ample cabinetry, perfectly blending style and functionality. The primary suite offers a spa-like retreat with an updated bathroom, modern vanity, designer lighting, and a tiled walk-in shower. Sliding doors lead to an expansive backyard where tranquil waterfront views set the stage for relaxing evenings, entertaining, and unforgettable sunsets. Beyond the home, enjoy an unbeatable lifestyle where you can walk, bike, or even take your golf cart to nearby attractions including Mobbly Bayou Beach Park, a public boat launch to Tampa Bay, Tampa Bay Pickleball, Veterans Park, Bicentennial Park, RE Olds Park, and more. You’re also just minutes from local favorites like Empower Adventures Zip Line and the Oldsmar Organic Community Garden. With Tampa International Airport only about 20 minutes away, convenience meets lifestyle in this exceptional property. This is a rare chance to own a fully updated waterfront home with no HOA in one of Oldsmar’s most established and sought-after communities.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Julian Jackson (301-272-4192)
400 SHORE DR E, OLDSMAR, FL 34677
$1,000,00077 Days on yellowkey MLS ID: TB8478151
3 Days Off yellowkey (back on 5/7/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1890 Built: 1957 Tax: $3,995 (2025)Community: Country Club Add To Oldsmar RevSingle Family
Taxes:$3,995
Remarks: Under contract-accepting backup offers. The Ultimate Waterfront Canvas: 150ft of Panoramic Bay Frontage. Secure a legacy-grade homesite on one of the most expansive waterfront lots in Oldsmar. Situated on almost ¾ acre on the prettiest street in Oldsmar, 400 Shore Drive E offers a rare 150 feet of direct, unobstructed frontage on Safety Harbor. This is a premier opportunity for a visionary buyer or elite builder to bypass the limitations of existing construction and design a bespoke custom estate from the ground up. While the current structure is a teardown (sold as-is), its presence provides a significant footprint and potential impact fee advantages for your new architectural masterpiece. Experience total privacy and some of the most breathtaking, wide-water sunset views found anywhere in the Tampa Bay region. Just minutes from the refined trails of RE Olds Park and the area’s top dining, this location perfectly balances secluded coastal living with urban convenience. Don’t just buy a home—build a landmark on the water’s edge.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Crystal Tipton, Mrs (813-436-7229)
1802 CHINABERRY DR, OLDSMAR, FL 34677
$375,000201 Days on yellowkey MLS ID: TB8439498
5 Days Off yellowkey (back on 5/7/2026)
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)
420 CYPRESS VIEW DR, OLDSMAR, FL 34677
$485,0001 Day on yellowkey MLS ID: TB8505264
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1870 Built: 1998Monthly Fee: $140 Tax: $4,405 (2025)Community: Preserve At Cypress Lakes Ph I TheSingle Family
Taxes:$4,405
Remarks: Welcome to your private slice of paradise in Oldsmar! Updates include a 2026 AC, 2026 Roof, and 2021 Water Heater for peace of mind. This beautifully maintained three-bedroom, three-bathroom pool home offers the perfect blend of comfort and Florida living - nestled on a premium lot with preserve views, no rear or side neighbors, and only one neighboring home for added privacy. Additional updates include whole-house water and air filtration added in 2025, and the home was painted in 2021. From the moment you arrive, you’ll be greeted by easy-to-maintain tropical landscaping that enhances the home’s curb appeal. Step inside to a light and bright interior featuring a welcoming front living room with a cozy fireplace and crown molding that continues throughout the home. High ceilings create an open, airy feel as you move through the thoughtfully designed layout. The spacious kitchen is conveniently located to your right and is well-equipped with abundant cabinetry, a separate pantry for extra storage, and a charming breakfast nook. A laundry room sits just off the kitchen for added convenience. The kitchen opens seamlessly to the main living area, where wood-look vinyl flooring, a ceiling fan, and views of the pool make it the perfect space to relax or entertain. The primary suite is generously sized with high ceilings, wood-look vinyl flooring, and an attached bathroom featuring a dual-sink vanity, soaking tub, and separate glass-enclosed shower. Additional bedrooms are comfortably sized and include ceiling fans, offering flexibility for family, guests, or a home office. Step outside and truly embrace the Florida lifestyle. The screened-in pool area is surrounded by a serene, tree-lined preserve, creating a peaceful and private outdoor retreat. Enjoy a covered space ideal for dining, grilling, or simply lounging poolside year-round. Located near highly rated schools, as well as a variety of dining and shopping options, this home offers both convenience and tranquility in one desirable package. Schedule your showing today!
Listing is courtesy of: EXP REALTY LLC (866-308-7109)
Listing Agent: Jeffrey Borham, Pa (866-308-7109)
124 LOBLOLLY CT #D, OLDSMAR, FL 34677
$155,00053 Days on yellowkey MLS ID: TB8487484
REDUCED by $5,000 (3.1%) on 05/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 915 Built: 1986Monthly Fee: $665 Tax: $2,239 (2025)Community: Gardens Of Forest Lakes Condo TheCondo
Taxes:$2,239
Remarks: Unit tottaly Renovated New Kitchen Bath Bathrooms and flooring at the Garden of Forest lakes 2 Bedroom 2 bath
Listing is courtesy of: LYN PROPERTIES (813-951-3083)
Listing Agent: Meir Barack (813-951-3083)
138 BRENT CIR, OLDSMAR, FL 34677
$725,00023 Days on yellowkey MLS ID: TB8496402
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2258 Built: 2002Monthly Fee: $475 Tax: $9,980 (2025)Community: Seaside EstatesSpa: YesTownhouse
Taxes:$9,980
Remarks: Welcome to 138 Brent Circle in desirable gated Seaside Estates—an exceptional opportunity to own the largest corner townhome in this sought-after waterfront community in Oldsmar. Perfectly positioned to capture panoramic views of Tampa Bay, this residence offers a rare combination of space, scenery, and coastal lifestyle, complete with a private boat slip for easy access to the water. This spacious 4-bedroom, 3-bath home features a thoughtfully designed layout with abundant natural light and comfortable living areas ideal for both everyday living and entertaining. The inviting living room is anchored by a cozy fireplace, creating a warm focal point while showcasing the stunning water views beyond. A second fireplace in the primary bedroom adds an extra layer of comfort and charm, creating a relaxing private retreat. The kitchen offers ample cabinetry and workspace, seamlessly connecting to the dining and living areas for a functional, open feel. Each bedroom provides flexibility for a variety of living arrangements, while the three full bathrooms add convenience and comfort. An oversized garage delivers generous storage and parking space—an added benefit rarely found in townhome living. As a corner unit, the home enjoys enhanced privacy and additional natural light. Step outside and take in the tranquil waterfront setting, where you can relax, entertain, or set out for a day on Tampa Bay directly from your own boat slip. Conveniently located near parks, shopping, dining, and major roadways, this property offers the perfect blend of peaceful coastal living and everyday accessibility. Don’t miss your chance to own a premier waterfront residence in Seaside Estates—schedule your private showing today.
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Kathy Grams (727-259-9247)
382 FOUNTAINVIEW CIR, OLDSMAR, FL 34677
$520,0003 Days on yellowkey MLS ID: TB8499334
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1875 Built: 1995Monthly Fee: $95 Tax: $5,232 (2025)Community: Fountains At Cypress Lakes TheSingle Family
Taxes:$5,232
Remarks: Welcome home to this stunning, move-in ready 4 bedroom, 2 bath split floor plan in one of Oldsmar's most sought-after neighborhoods - and zoned for some of the top-rated schools in the area. From the moment you walk in, you'll notice the difference that thoughtful, high-quality updates make. Soaring vaulted ceilings and elegant columns greet you in the formal living room, while French doors open to a versatile den or 4th bedroom. The heart of the home is a beautifully updated gourmet kitchen featuring shaker-style soft-close cabinetry, quartz countertops, subway tile backsplash, stainless steel appliances, a breakfast bar, and a sunny breakfast nook ... all flowing naturally into the family room and out to the screened porch through a slider, perfect for that indoor-outdoor Florida lifestyle. The primary suite is a true retreat, complete with a spa-inspired bath boasting dual sinks, quartz countertops, and a step-in shower. Two additional bedrooms share a well-appointed bath. Throughout the home you'll find brand new engineered hardwood and LVP flooring, freshly painted interiors, popcorn ceilings removed, and updated baths - every detail has been addressed. And the big ticket items? All taken care of. Brand new roof (May, 2026), newer appliances, new garage door motor, new back pavers, and a fully fenced lot with complete privacy,fresh landscaping, and a freshly painted exterior in warm, natural tones that give the home incredible curb appeal. This is the one you've been waiting for — all the charm, all the updates, and an unbeatable Oldsmar location close to Gulf beaches, parks, golf courses, shopping, and Tampa International Airport.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Marianne Knowles (813-720-9201)
510 CABERNET WAY, OLDSMAR, FL 34677
$349,9002 Days on yellowkey MLS ID: TB8506118
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1525 Built: 2015Monthly Fee: $418 Tax: $2,501 (2025)Community: Tuscany Woods SouthTownhouse
Taxes:$2,501
Remarks: Welcome to Tuscany Woods! This beautifully maintained 3-bedroom, 2.5 bath Taylor Morrison townhome, built in 2015, offers the perfect blend of style, comfort, and convenience in a gated Oldsmar community. Proudly owned by the original owner and located in a non-flood zone, this home sits high and dry with no history of flood or storm-related damage. Step inside to a light and airy open floor plan featuring crown molding and chair rail accents downstairs, upgraded Pottery Barn lighting throughout, updated ceiling fans, and all lighting on dimmer switches. The kitchen has been thoughtfully updated with quartz countertops, shaker wood cabinetry, stainless steel appliances, a larger upgraded kitchen sink. range with hood, solid wood shelving in walk-in pantry, and added lighting above the bar area. Additional upgrades include zebra blinds downstairs, a storm door with screen enclosure, custom closet system in the primary suite, and added cabinetry in the laundry room for extra storage and functionality. Enjoy relaxing on the screened-in patio and the convenience of a one-car garage. The HOA covers water, sewer, trash, roof maintenance, exterior paint, lawn care, and landscaping, offering low-maintenance living in a prime location close to shopping, dining, parks, beautiful Gulf beaches, and approximately 30 minutes to Tampa International Airport. This move-in ready gem is waiting to welcome it's next owners home!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-799-2227)
Listing Agent: Julie Barnhardt (727-452-6741)
313 JEFFERSON AVE S, OLDSMAR, FL 34677
$449,00010 Days on yellowkey MLS ID: TB8502786
REDUCED by $1,000 (0.2%) on 05/07/2026
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: Seller is willing to contribute up to $9,000 toward buyer closing costs and/or allowable credits with an acceptable offer. Open House: Saturday, May 9th, from 1:00 PM to 3:00 PM. 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 offers a spacious living area filled with natural light, a covered front porch, and an upstairs bonus room that can function well as a home office, playroom, guest area, kids room, or other flexible living space. The upstairs bonus room was not included in the total bedroom count. 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. A clean 4-point inspection, wind mitigation report, WDO report, and recent appraisal are available. The recent appraisal came in at $475,000.
Listing is courtesy of: GRAYSTONE REAL ESTATE (727-201-4011)
Listing Agent: Bradley Dreher (863-346-0500)
403 BLUE MARLIN DR, OLDSMAR, FL 34677
$184,000192 Days on yellowkey MLS ID: TB8442487
REDUCED by $5,000 (2.6%) on 05/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1078 Built: 1993Monthly Fee: $70Community: Gull-Aire VillageManufactured Home
Taxes:$0
Remarks: Assumable VA Loan at 2.8% for Qualified Veteran Available! Welcome to your new home in the highly sought-after 55+ Gull-Aire Village! Perfectly situated on a spacious corner lot, this charming Jacobsen manufactured residence offers both comfort and convenience within walking distance to the community pool and clubhouse. Constructed in 1993, it features durable ¾ inch plywood subfloors with laminate, carpet, and tile flooring throughout. Enjoy the versatility of the enclosed Florida room, equipped with central air and heat as well as a custom fan system—ideal for hobbies and creative projects. Recent upgrades include a new hot water heater installed in 2018 and beautifully renovated bathrooms completed in 2020. Further improvements include new windows, a front door, siding, and insulation added in 2013.The kitchen is outfitted with sleek 2019 stainless-steel appliances including a refrigerator and dishwasher. A new air conditioning system installed in 2016. Unique to this home is an electric custom ramp capable of lifting to 600 lbs., offering exceptional accessibility for those with mobility needs. A roof-over was added in 2005, and an inside laundry area comes complete with a washer and dryer for your convenience. The vibrant clubhouse is the heart of the community, hosting monthly events and providing amenities such as a pool table, shuffleboard, bocce ball court, and a heated pool and spa. There are also regular activities to keep you engaged and active, including yoga, bingo, cards, and line dancing. The golf cart-friendly streets make getting around a breeze! With HOA fees at just $70 per month, you will enjoy affordable living in a wonderfully maintained neighborhood. This pet-friendly community allows one pet of any size, and a second pet is permitted with a doctor's note for emotional support. Best of all, ownership includes the land—no lot rent! Everyday conveniences are just steps away, with AMC Theatres, Bealls, Marshalls, PetSmart, Five Below, and Dollar Store across the street, as well as popular dining options like Shaker & Peel, Craft Street Kitchen, Mandola's, Country Pizza Italian Grill, and Eve's Family Restaurant. Major retailers such as Super Walmart and Publix, along with Countryside Hospital, are only minutes from your door. For outdoor enthusiasts, the stunning beaches of Honeymoon Island and Caladesi State Park are just ten miles away, and a scenic biking and walking trail along the canal offers easy access from within the community. Room sizes are approximate. Do not miss your chance to enjoy the best of Oldsmar living in one of the area's most desirable communities!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Jayne Phoenix (727-433-1411)
50 KELLEYS TRL, OLDSMAR, FL 34677
$1,200,0003 Days on yellowkey MLS ID: TB8504781
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3240 Built: 1993Monthly Fee: $185 Tax: $7,792 (2025)Community: Turtle Creek Unit-OneSingle Family
Taxes:$7,792
Remarks: Welcome to an exceptional residence at 50 Kelleys Trail, nestled within the prestigious gated enclave of Turtle Creek within East Lake Woodlands in Oldsmar. This refined home embodies effortless elegance and elevated Florida living, offering a seamless blend of sophistication, comfort, and privacy. From the moment you enter, you’re greeted by soaring ceilings, abundant natural light, and thoughtfully designed living spaces that create an inviting yet upscale atmosphere. The open-concept layout flows beautifully, ideal for both intimate gatherings and grand entertaining. The kitchen serves as the heart of the home, featuring generous workspace, ample cabinetry, and a layout designed for both functionality and style. The primary suite is a true retreat, offering a serene escape with spacious proportions and a well-appointed en-suite bath. Step outside to your private outdoor setting, where you can unwind in tranquility or entertain guests while enjoying Florida’s year-round sunshine. Whether relaxing or hosting, this space offers the perfect backdrop for a luxury lifestyle. Located within one of Oldsmar’s most sought-after golf course communities, residents of East Lake Woodlands have access to optional resort-style amenities, including championship golf, tennis, fitness, and social experiences. Ideally positioned near upscale dining, boutique shopping, top-rated schools, Tampa International Airport, and the Gulf Coast’s renowned beaches, this home offers both convenience and exclusivity. Experience refined living in one of Oldsmar’s premier communities—schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
549 LONGWOOD CIR, OLDSMAR, FL 34677
$525,0003 Days on yellowkey MLS ID: A4692285
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1344 Built: 1984Monthly Fee: $30 Tax: $5,336 (2025)Community: Manors Of Forest Lakes TheSingle Family
Taxes:$5,336
Remarks: Welcome to your private retreat in the heart of Oldsmar. Located in the desirable Longwood community, this beautifully maintained home offers the perfect blend of comfort, charm, and Florida living. Surrounded by mature landscaping and peaceful streets, 549 Longwood Circle features spacious living areas, abundant natural light, and an inviting layout ideal for both entertaining and everyday living. Step outside to enjoy a relaxing backyard setting with room to unwind, host gatherings, or create your own outdoor oasis. Conveniently located near top-rated schools, parks, shopping, dining, and the Gulf beaches, this home delivers both privacy and accessibility. Whether you're looking for a full-time residence or a seasonal getaway, this property is an incredible opportunity to own a piece of paradise in one of Tampa Bay’s most sought-after communities.
Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)
Listing Agent: Susan Kolesnikov (916-272-9177)
121 LOBLOLLY CT #C, OLDSMAR, FL 34677
$161,9003 Days on yellowkey MLS ID: A4692680
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 915 Built: 1987Monthly Fee: $635 Tax: $2,263 (2025)Community: Gardens Of Forest Lakes Condo TheCondo
Taxes:$2,263
Remarks: Owner remodeled for family member but family member chose other living arrangements. Here is your chance to have a fully updated unit fit for higher end living without the cost.
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
602 BAY LAKE TRL, OLDSMAR, FL 34677
$375,0008 Days on yellowkey MLS ID: TB8503595
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1554 Built: 1983 Tax: $937 (2025)Community: Shoreview Ph ISingle Family
Taxes:$937
Remarks: Located in the Shoreview community of Oldsmar, this home offers a great combination of location, schools, and potential. Zoned for highly rated schools, this home is a smart choice for buyers looking to get into a strong school district while still having the opportunity to make it their own. Set on a peaceful homeowner-owned lake, the property features a private pool and relaxing water views—perfect for everyday living or entertaining. Inside, the home offers a desirable split floor plan for added privacy, a spacious primary suite with a walk-in closet, and an additional flex space/den ideal for a home office, playroom, or second living area. It’s ready for updates, making it ideal for buyers who want to customize and add value over time. You’re just minutes from R.E. Olds Park on Shore Drive, where you can enjoy festivals, outdoor concerts with fireworks over the water, a fishing pier, and beautiful sunset views. The area is also surrounded by waterfront parks offering bike and kayak trails, pickleball, basketball and tennis courts, walking and jogging paths, playgrounds, picnic areas, a small beach, and even a community garden. In addition to all the outdoor amenities, the home is conveniently located near great restaurants, shopping, Tampa International Airport, and the area’s award-winning Gulf beaches. And for peace of mind, the property is high and dry and did not have hurricane flooding or damage. If you’ve been looking for a home in a great location with room to make it your own, this one is definitely worth seeing. Please note: No sight unseen, assignable, or seller financing offers will be considered.
Listing is courtesy of: BRAINARD REALTY (813-922-2891)
Listing Agent: Sandra Santos Garbutt (727-418-1593)
436 LAFAYETTE BLVD, OLDSMAR, FL 34677
$700,000282 Days on yellowkey MLS ID: TB8412856
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2695 Built: 1994 Tax: $10,665 (2024)Community: Oldsmar Rev MapSingle Family
Taxes:$10,665
Remarks: One or more photo(s) has been virtually staged. Must see this 4 bedroom/2.5 bath home with almost 2700 Sq/Ft on one of the highest/majestic lots in downtown Oldsmar! Relax by the wood fireplace with your family in the comfortable living room! Entertain guests, make a fire-pit area, or start your own garden in the expansive backyard with Lanai! Lot is almost a half acre! Fantastic kitchen with granite countertops, stainless steel appliances, plenty of wood cabinets/countertop space and breakfast bar! Large master bedroom with enormous walk-in closet and newly updated master bath with soaking tub, his-and-her sinks and high end stone tile throughout! Take the private glass vacuum elevator to the second floor! Also a dining area, family room and office! Some additional upgrades include: High ceilings, sprinkler system, hurricane windows, whole house instant hot water, water softener/filter system, updated flooring throughout, vinyl fencing, smart-home switches/recessed lighting, updated 2 car garage, block home. Short walk to Bicentennial Park that has a dog park, playground, tennis/basketball/pickleball courts. Also near boat launch, hiking/biking trails, library, fishing pier, museum and schools. Home had no hurricane/water damage! Oldsmar is located centrally in north Pinellas County and is a short drive to world class gulf beaches, Tampa International Airport, sporting venues, theater, shopping, restaurants and much, much more!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Dillon Currier (727-919-4214)
202 MEADOW LN #50, OLDSMAR, FL 34677
$185,0004 Days on yellowkey MLS ID: TB8505503
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 875 Built: 1985Monthly Fee: $427 Tax: $2,030 (2025)Community: Meadows Condo Unit Two At East Lake Woodlands TheCondo
Taxes:$2,030
Remarks: Welcome to this well-located, offering comfort and convenience. This residence features 2 bedrooms and 2 bathrooms, providing a functional layout suitable for a variety of living needs. Ideally positioned with easy access to major roadways, the home allows for a smooth commute to nearby areas such as Tampa and Clearwater. The surrounding area offers a wide range of shopping, dining, and entertainment options. Just minutes away, you’ll find Westfield Countryside Mall, featuring a variety of retail stores and services. For travel convenience, Tampa International Airport is easily accessible. Healthcare services are nearby at Mease Countryside Hospital, adding an extra layer of convenience. Dining options in the area include well-known establishments such as Chick-fil-A and Starbucks, along with a variety of local favorites. This property presents a great opportunity to enjoy a comfortable lifestyle in a centrally located community close to everyday essentials.
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Alexandra Muneton (813-802-1677)
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