Location: Oldsmar , 34677
Do Not Show Listings
347 CANAL WAY, OLDSMAR, FL 34677
$199,000182 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,609
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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 is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Asher Walli (727-744-7466)
1811 FOREST DR, OLDSMAR, FL 34677
$475,00022 Days on yellowkey MLS ID: TB8491038
REDUCED by $27,500 (5.5%) on 04/14/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2142 Built: 1973 Tax: $6,771 (2025)Community: Harbor Palms-Unit ThreeSingle Family
Taxes:$6,771
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
Remarks: Recently updated pool home located in Oldsmar with an open living room and dining room that feature vinyl floors thoughout the entire inside. Kitchen has stainless appliances, marble countertops, and a natural stone ledger backsplash. House has been recently painted along with a new A/C Unit installed in 2025. Roof and hot water heater were replaced in 2024. Close proximity to Sheffield Park and is a short drive to Philippe Park. If you don't want to go anywhere then there is a screened-in pool for your enjoyment without ever leaving the house. Recently passed 4 point inspection in July of 2025. Seller motivated.
Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)
Listing Agent: Brian Mathay (813-482-6097)
303 MEADOW LN, OLDSMAR, FL 34677
$190,0004 Days on yellowkey MLS ID: TB8497109
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 879 Built: 1985Monthly Fee: $422 Tax: $2,724 (2025)Community: Meadows Condo At East Lake WoodlandsSpa: NoCondo
Taxes:$2,724
Remarks: Welcome to this highly sought-after gated community of East Lake Woodlands, which is move-in ready. This quiet, well-maintained neighborhood offers the perfect mix of tranquility and accessibility. Whether you're a first-time buyer, a snowbird looking for a Florida retreat, or an investor adding to your portfolio, this low-maintenance home checks all the right boxes. Enjoy a friendly atmosphere with shaded streets and a suburban feel while still being just minutes from shops and restaurants. The Primary suite features 2 walk-in closets with access to the tranquil back patio. The unit offers plenty of closet storage, fully furnished with enclosed laundry on the patio, one owner parking and ample guest parking. Residents have the option to join the East Lake Woodlands Country Club, unlocking access to a range of upscale amenities, including 2 championship 18-hole golf courses, a clubhouse with dining and social events, pickleball and tennis courts, a modern fitness center with group classes, and a resort-style swimming pool. Some nearby outdoor attractions are: Empower Adventures Zipline Park, R.E. Olds Park, and Mobbly Bayou Wilderness Preserve and Harbor Palms Nature Park. Minutes from Shaker & Peel, one of Yelp's top-rated restaurants. Enjoy shopping at the iconic Oldsmar Flea Market, catch the latest blockbuster at AMC Woodlands Square, or head to Countryside Mall for bigger retail options. Quick access to Tampa Road and Curlew Road makes commuting to Tampa, Clearwater, or St. Pete easy and efficient.
Listing is courtesy of: CENTURY 21 BEGGINS (800-541-9923)
Listing Agent: Shauna Hoyt (727-424-0072)
260 BALSAM DR, OLDSMAR, FL 34677
$249,900197 Days on yellowkey MLS ID: TB8433742
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1250 Built: 1981Monthly Fee: $440 Tax: $960 (2024)Community: East Lake Woodlands Cluster HomesVilla
Taxes:$960
Remarks: SIGNIFICANT PRICE DECREASE!!! Owners are motivated!!! This desirable end-unit villa in exclusive East Lake Woodlands combines comfort, privacy, and an ideal layout for everyday living or entertaining. Featuring two spacious primary suites, each with its own ensuite bath and split floor plan design, the home provides excellent privacy for residents and guests alike. The open layout includes a welcoming family room, a dedicated dining room, and a bright eat-in kitchen with a generous pass-through bar—perfect for casual dining, entertaining, or extra storage. A charming front courtyard offers an inviting spot for morning coffee or al fresco meals, while the expansive lanai, complete with removable windows, provides a versatile additional living space to enjoy year-round. Thoughtful storage solutions are found throughout, with ample closet space to keep everything organized. Important updates include a roof replacement in 2021, an upgraded electrical panel in 2017 and a 2016 AC system. The HOA provides peace of mind with coverage that includes roof replacement, exterior painting, wood repairs, landscaping, lawn maintenance, irrigation, and fertilization. Located within the highly regarded East Lake Woodlands, a premier gated golf course community, residents have access to optional membership opportunities that feature golf, tennis, swimming, fitness, dining, and social events. With its combination of thoughtful design, modern updates, and resort-style community amenities, this villa offers the perfect place to call your year round home or winter residence. Don't delay.
Listing is courtesy of: MARC JOSEPH REALTY, INC (727-644-9333)
Listing Agent: Colleen Monagas (727-644-9333)
141 LAKEVIEW WAY #141, OLDSMAR, FL 34677
$174,90042 Days on yellowkey MLS ID: TB8483907
REDUCED by $4,100 (2.3%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1980 Tax: $3,466 (2025)Community: East Lake WoodlandsSpa: NoCondo
Taxes:$3,466
Remarks: PRICE REDUCED!! Enjoy peaceful Florida living in this charming condo located in a quiet gated community in desirable East Lake Woodlands. This well-maintained residence offers a comfortable layout with abundant natural light and relaxing views of the lake, creating a serene setting to come home to each day. The living and dining areas flow seamlessly, providing an inviting space for both everyday living and entertaining. Large windows help bring the outdoors in while highlighting the tranquil lake view. The kitchen is conveniently located and designed for functionality and ease. Residents of this gated community enjoy access to a sparkling community pool, perfect for relaxing or cooling off on warm Florida days. The peaceful surroundings combined with scenic water views make this property especially appealing. Conveniently located near shopping, dining, parks, and major roadways, the home offers easy access to nearby destinations including Tampa, Clearwater, and St. Petersburg. A wonderful opportunity to enjoy low-maintenance living with beautiful lake views in one of Oldsmar’s most desirable gated communities, and with a freshly painted front door.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Douglas Brown (614-306-4665)
2270 CHRISTY LN, OLDSMAR, FL 34677
$1,250,00058 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!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Claudia Tweed (727-433-4596)
2328 WARWICK DR, OLDSMAR, FL 34677
$854,000238 Days on yellowkey MLS ID: TB8419306
REDUCED by $20,000 (2.3%) on 04/13/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3294 Built: 1995Monthly Fee: $127 Tax: $5,742 (2024)Community: Warwick HillsSpa: YesSingle Family
Taxes:$5,742
Elementary School: Cypress Woods Elementary-PN
Remarks: Welcome to the charming Warwick Hills enclave within the desirable Eastlake Woodlands community! Enjoy the peaceful drive home beneath beautiful tree-canopied streets, where this exceptional two-story residence awaits on one of the largest corner lots in the neighborhood. Perfectly elevated and high & dry, this home has never experienced standing water. A stately presence greets you with elegant landscaping, including a brand new row of privacy hedge plants & palms surrounding the pool enclosure. Side-entry 3-car garage, and an extended driveway offering ample parking. Step inside through double doors into a grand foyer with soaring ceilings. The thoughtful layout includes formal living and dining rooms, as well as a spacious family room featuring a cozy wood-burning fireplace and sliding glass doors that open to the lanai and sparkling pool. The kitchen and family room blend seamlessly with an open floor plan, highlighted by an island, wet bar, and three pantries, two are oversized pantry closets—ideal for both everyday living and entertaining. From here, enjoy relaxing views of the pool, jetted spa( not heated) , and backyard, where you may even spot deer strolling through. A versatile office on the main floor can easily serve as a 5th bedroom, complemented by a full-size laundry room and powder bath. Upstairs, the expansive primary suite welcomes you with double-door entry, generous space for king-sized furnishings, and a private sitting area. The suite also offers two walk-in closets and a stunning, brand-new freshly renovated bathroom with a soaking tub, dual vanities, private water closet, and a new glass-enclosed shower. The 2nd floor also features 3 more bedrooms and 2 more full baths. Additional updates include a freshly painted exterior (2023), roof (2022), A/C units (2018 & 2019), hurricane shutters for all windows & doors, accordion shutters for sliding glass doors, fresh carpet on staircase, water heater (2018) ensuring peace of mind for years to come. Ardea Country Club has recently been updated. Residents can take advantage of premier golf, tennis, dining, and social memberships. With easy access to Hillsborough and Pasco counties, this centrally located home is just minutes to shopping, dining, top-rated schools, and all that the Tampa Bay area has to offer.
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Roberta Celiberti (727-488-1235)
215 CLAYS TRL #215, OLDSMAR, FL 34677
$305,000135 Days on yellowkey MLS ID: TB8452814
REDUCED by $10,000 (3.2%) on 04/01/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1237 Built: 1988Monthly Fee: $618 Tax: $3,830 (2024)Community: Heatherwood Unit One CondoCondo
Taxes:$3,830
Remarks: Motivated Seller and a new price! An absolutely stunning condo for sale in Eastlake Woodlands. This two bedroom, two bathroom unit has been fully remodeled and is ready for you to move in. It boasts a brand-new kitchen including soft close white cabinets, granite counters, and stainless steel appliances. Both master and guest bath have been fully renovated with stunning tile work and vanities that match the kitchen. The new floors were replaced and provide a scratch resistant living space. The high ceilings make this home feel extravagant and airy. Offering tons of privacy, this end unit is mere steps from the pool which makes it feel like your own private oasis. Don't miss the perfect opportunity to live in this maintenance free community. The HOA covers water, sewer, trash, cable internet, insurance and so much more. A/C, water heater and all appliances are new.
Listing is courtesy of: RE/MAX COLLECTIVE (813-438-7841)
Listing Agent: Whitney Parks (727-642-7455)
904 VINEYARD LN, OLDSMAR, FL 34677
$340,00053 Days on yellowkey MLS ID: TB8479523
0 Days Off yellowkey (back on 4/13/2026)
REDUCED by $10,000 (2.9%) on 04/01/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1525 Built: 2017Monthly Fee: $418 Tax: $3,149 (2025)Community: Tuscany Woods PreserveTownhouse
Taxes:$3,149
Remarks: Under contract-accepting backup offers. Private Preserve Views | Move-In Ready | Optional Turnkey Furnished. Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome in the gated Tuscany Woods Preserve community. Built in 2017, this newer construction home offers a rare combination of privacy, low-maintenance living, and a peaceful natural setting. The open-concept layout is filled with natural light and designed for everyday comfort and easy entertaining. The kitchen features stone countertops, solid wood cabinetry, stainless steel appliances, and a seamless flow into the living and dining areas. Upstairs, the spacious primary suite offers a walk-in closet and a well-appointed bath with dual vanities and a glass-enclosed shower. Two additional bedrooms provide flexibility for guests, a home office, or additional living space. Step outside to one of the home’s standout features — a covered and screened lanai with an extended paver patio overlooking a private preserve. With no rear neighbors, this is the perfect place to relax and unwind. Additional highlights include a 1-car garage with built-in overhead storage, gated community access, and a convenient central location close to shopping, dining, and major roadways. Furniture is available separately, making this a potential turnkey opportunity for buyers seeking a fully furnished home.
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (813-749-0875)
Listing Agent: Peter Gawienczuk (813-743-4178)
412 CEDAR RIDGE CT, OLDSMAR, FL 34677
$199,99915 Days on yellowkey MLS ID: TB8493131
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1984Monthly Fee: $268 Tax: $1,743 (2025)Community: Villas Of Forest Lakes TheVilla
Taxes:$1,743
Remarks: Under contract-accepting backup offers. Pet-Friendly Villa in Forest Lakes | 2 Bed, 2 Bath | Private Fenced Yard | Low HOA Welcome to this rare 2-bedroom, 2-bath villa in Forest Lakes offering maintenance-free living with a low $268/month HOA and NO pet restrictions—perfect for pet lovers! This 900 sq ft split floor plan features two primary suites, ideal for roommates, guests, or multi-generational living. The kitchen includes oak cabinets, granite countertops, and a double sink, opening to a bright living space with laminate flooring and sliding glass doors. Step outside to your private PVC-fenced yard a vinyl-enclosed patio, perfect for relaxing or entertaining. Community amenities include: Community pool Tennis courts, basketball court & racquetball Fishing pier & private lakes Playground & picnic areas The HOA covers exterior maintenance, roof, building insurance, trash, and grounds, making this a truly low-maintenance home. Prime location! Conveniently located near shopping, restaurants, grocery stores, Walmart, and public transportation, and just 20 minutes to Tampa, Clearwater, and St. Petersburg. Villas in Forest Lakes are rarely available and sell quickly—schedule your showing today!
Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)
Listing Agent: Kerin Clarkin (813-569-6294)
124 LOBLOLLY CT #H, OLDSMAR, FL 34677
$160,00035 Days on yellowkey MLS ID: TB8481313
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 915 Built: 1986Monthly Fee: $666 Tax: $2,517 (2025)Community: The Gardens Of Forest Lakes CondoCondo
Taxes:$2,517
Remarks: Investor-friendly opportunity: This turn-key property currently has a cash flowing year-long tenant in place, making it an excellent 1031 exchange option for investors seeking immediate rental income with a low-maintenance property. Welcome to this beautifully fully remodeled 2-bedroom, 2-bathroom condo located at 124 Loblolly Ct, Unit H in desirable Oldsmar. This move-in-ready home has been thoughtfully updated from top to bottom, featuring brand new carpet, fresh interior paint, and new appliances, creating a clean and modern living space ready for its next owner. The spacious layout offers comfortable living with two well-appointed bedrooms, including a primary suite with a private bathroom. The open living and dining area provides a comfortable setting for relaxing or entertaining, while the fresh upgrades throughout give the home a bright, refreshed feel. Located in a quiet, well-maintained community, residents enjoy the convenience of nearby parks, swimming pool, playground, tennis, basketball and racquetball courts, shopping, dining, and easy access to major commuting routes. The location provides quick connectivity to both Tampa and Clearwater, while still enjoying the charm and waterfront lifestyle of Oldsmar along Tampa Bay. Whether you're looking for an investment property or a future personal residence, this fully updated condo offers comfort, convenience, and long-term value in a highly desirable Tampa Bay location.
Listing is courtesy of: HOMESMART (407-476-0461)
Listing Agent: Nikki Pagoria (314-221-6810)
40 SHAMROCK WAY #40, OLDSMAR, FL 34677
$255,00056 Days on yellowkey MLS ID: TB8471405
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1502 Built: 1986 Tax: $2,572 (2024)Community: St Andrews CondoCondo
Taxes:$2,572
Remarks: Welcome home to 40 Shamrock Way in sunny Oldsmar FL. This move-in ready, updated 2-bedroom, 2-bath condo with a loft, offering 1,502 square feet of light-filled living space in the highly sought-after East Lake Woodlands community in Oldsmar. Featuring an open floor plan, voluminous ceilings, abundant windows, and a split bedroom layout, this home feels bright, spacious, and welcoming, perfect for both everyday living and entertaining. The updated kitchen opens to the main living area and showcases modern finishes, ample cabinetry, and a convenient eating bar. Updated flooring throughout enhances the cohesive design, while in-unit laundry adds everyday ease. The versatile loft provides the ideal space for a home office, media room, or additional living area. The expansive primary suite is a true retreat, featuring a huge walk-in closet, dual sinks, and a spa-inspired bathroom with both a separate shower and tub. The secondary bedroom and bath are thoughtfully positioned on the opposite side of the home, ideal for guests or multigenerational living. Recent updates include a new HVAC and water heater, offering added peace of mind. Step outside to your large, private screened back porch, perfect for relaxing or enjoying Florida’s indoor-outdoor lifestyle. This maintenance-free, lock-and-leave community features a swimming pool, assigned covered parking, and ample guest parking. The monthly HOA of $770 provides exceptional value and includes cable TV, common area taxes, community pool access, exterior building insurance (homeowner to obtain interior insurance), exterior building maintenance, grounds maintenance, sewer, and trash service, allowing for truly low-maintenance living. Just 25 minutes to Tampa International Airport and approximately 20 minutes to the Dunedin Causeway and Honeymoon Island. Enjoy shopping, dining, and everyday conveniences all nearby. East Lake Woodlands is known for its excellent walkability and is within walking distance of the Ardea at East Lake Woodlands Country Club, where optional golf membership is available. This home delivers the perfect blend of comfort, convenience, and resort-style living, ideal as a primary residence, second home, or seasonal retreat.
Listing Agent: Jessica Christianson (719-229-1763)
172 LAKEVIEW WAY #172, OLDSMAR, FL 34677
$165,0007 Days on yellowkey MLS ID: TB8496591
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1980 Tax: $3,644 (2024)Community: East Lake Woodlands CondoCondo
Taxes:$3,644
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 2 bedroom, 2 bathroom second-floor condo located in the highly desirable gated community of East Lake Woodlands. This immaculate home features upgraded luxury vinyl plank flooring throughout and offers a serene, peaceful pond view perfect for relaxing mornings or evenings. Residents enjoy access to an exceptional lifestyle with two championship 18-hole golf courses, 14 Har-Tru tennis courts, and a stunning country club. Ideally situated near world-class beaches, scenic nature parks and preserves, and with convenient access to shopping and dining, this home is the perfect opportunity to embrace the best of the Florida lifestyle.
Listing is courtesy of: CENTURY 21 INTEGRA (800-593-7653)
Listing Agent: Becki Server (727-835-9696)
291 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677
$258,00093 Days on yellowkey MLS ID: TB8463435
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1110 Built: 1996Monthly Fee: $454 Tax: $2,205 (2025)Community: Countryside KeyTownhouse
Taxes:$2,205
Remarks: Welcome to the highly sought-after gated community of Countryside Key, ideally located in the heart of Oldsmar! This well-maintained home offers wood laminate flooring, a convenient ground-level laundry closet, and a screened-in lanai with an additional storage closet—perfect for relaxed Florida living. The kitchen opens seamlessly to the dining and living areas, creating an inviting open-concept layout ideal for everyday living and entertaining. Upstairs, you’ll find a desirable split floor plan featuring vaulted ceilings and two spacious, carpeted bedroom suites, each with its own private bath. Residents of Countryside Key enjoy a wealth of amenities, including a secure gated entrance, community pool, tennis courts, and a car wash station. Boat and RV parking are also available. Low monthly HOA fees cover cable, internet, phone, water, sewer, trash, exterior building maintenance, and exterior insurance—offering both convenience and peace of mind. Recent updates include new shut-off valves and a 2024 water heater. Ideally situated near airports, dining, shopping, entertainment, sports venues, and Florida’s award-winning Gulf beaches. Don’t miss this opportunity—schedule your private showing today!
Listing Agent: Tanner Tillung (727-479-4548)
1810 DRIFTWOOD CIR S, OLDSMAR, FL 34677
$370,00022 Days on yellowkey MLS ID: TB8490101
REDUCED by $10,000 (2.6%) on 04/13/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1456 Built: 1973 Tax: $1,957 (2025)Community: Harbor PalmsSpa: NoSingle Family
Taxes:$1,957
Elementary School: Oldsmar Elementary-PN
Remarks: Rare opportunity with an assumable FHA loan—potential buyers can step into favorable financing, subject to lender approval. Great solid home in a well established family neighborhood. This 2 Bedroom 2 Bath, 2 car garage home easily converted Bonus room bedroom for a growing family or office. The large living room features an updated bay window and an elegant electric fireplace. There is also a living room with an area for a dining room. The back of the home features enclosed patio rooms fantastic for entertaining. built in jacuzzi. The yard is fenced in. New blown insulation, new roof, new electrical panel, new ceilings, new ductwork. It has a bonus room that can be used as an office or extra room of your choice.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Angelique Blake (248-808-9399)
2208 SUNSET WIND LOOP, OLDSMAR, FL 34677
$365,000172 Days on yellowkey MLS ID: TB8441891
1 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1667 Built: 2019Monthly Fee: $545 Tax: $1,495 (2024)Community: Bayside TerraceTownhouse
Taxes:$1,495
Remarks: Under contract-accepting backup offers. This beautiful 3 bedroom, 2.5 bathroom townhome located in the heart of Oldsmar and is ready for a new owner. This spacious open concept has tile throughout the first floor. The stunning kitchen features white cabinets and granite countertops, a breakfast bar that seats 6 comfortably, pendant lighting, stainless appliances, and large pantry. The living room has sliders leading into the screened, paved, and covered patio. Upon entering the second floor, you will be greeted with a large loft area that can be used as an additional living room, library, or whatever your heart desires. The bedrooms are a split floorpan with the primary bedroom on the left while the remaining bedrooms and full bathroom on the right. The primary bedroom has 2 walk-in closets. The primary bathroom has dual sinks and a stand up shower. There is a laundry closet upstairs making it easy to do laundry. This unit also has a one car garage. The community features: a fitness room, pool with cabana, outdoor kitchen with grilling area, community dock, and is gated. Included in the HOA is exterior paint, roof, lawn care, water, were, and wifi/cable.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Yael Hatfield (813-264-7754)
20 FERNBROOK RD, OLDSMAR, FL 34677
$649,9998 Days on yellowkey MLS ID: TB8492357
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2147 Built: 1982Monthly Fee: $148 Tax: $5,980 (2025)Community: East Lake WoodlandsSpa: NoSingle Family
Taxes:$5,980
Remarks: Under contract-accepting backup offers. Tucked inside the 24-hour gated community of East Lake Woodlands, this beautifully maintained waterfront pool home welcomes you with undeniable curb appeal and a sense of arrival. A stamped concrete driveway accented with brick pavers and a charming brick walkway guide you to the inviting front entry, where a glass-insert front door with sidelights creates a light-filled first impression. Framed by swaying palm trees, lush landscaping, and outdoor lighting, the exterior sets the tone for relaxed Florida living. Inside, the home offers a thoughtfully designed split-bedroom floor plan with 4 bedrooms and 2 full baths, across 2,147 sq ft, providing both privacy and functionality. Rich engineered hardwood flooring flows throughout, adding warmth and sophistication. The heart of the home is the beautifully updated kitchen, featuring raised panel cabinetry with crown molding, soft-close drawers and cabinets, stainless pulls, under-cabinet lighting, and a built-in pantry with pull-outs. A Quartz countertop (2020) is complemented by a sleek glass tile backsplash. Appliances include a smooth-top range, new Frigidaire Gallery French door refrigerator and microwave, Bosch dishwasher, and a sink with touchless faucet. Recessed lighting enhances the galley-style layout, while the sunlit café area with floor-to-ceiling windows overlooking the lanai creates the perfect spot for casual dining. A separate closet pantry completes the space. The formal dining room features built-in cabinetry mirroring the kitchen, complete with a Quartz buffet server, glass backsplash and designer lighting. The living room impresses with a vaulted ceiling, wood-burning fireplace, and skylight, while sliding glass doors open to the lanai and pool area, enhancing indoor-outdoor living. The sunken family room offers a relaxed retreat, with lanai access, and includes a stunning billiard table with all accessories and overhead lighting fixture. The updated primary suite, with direct access to the lanai, offers a private retreat. The ensuite bath is beautifully designed, featuring a barn door entry that opens to a double vanity with Quartz countertops, undermount sinks, and ample cabinetry and drawers. The expansive walk-in shower showcases a seamless glass panel, built-in bench, shampoo niches, rain head and handheld fixtures, and a high window for natural light, along with an exhaust fan for added comfort. A custom walk-in closet with built-ins completes this well-appointed space. Secondary bedrooms are generously sized, with ample closet space, and share a well-appointed bathroom featuring a jetted tub, and a vessel sink set atop a double vanity. The hallway includes a linen closet with attic access and a door with convenient access to the lanai. Step outside to your private outdoor oasis, where an upgraded Pebble Tec pool is surrounded by a stamped concrete deck. The home is ideally positioned alongside a pond bordering the side and rear of the property. The covered, screen-enclosed lanai with a beadboard ceiling, three fans, and a manual retractable screen for added shade and comfort. A pass-through window from the kitchen with a bar counter on the lanai side makes outdoor dining effortless. Additional highlights include NEW A/C 2026, PGT hurricane windows, new baseboards, interior doors, and updated deora switches and outlets. Don’t miss this opportunity to own a waterfront pool home in one of Oldsmar most sought after gated communities. Schedule your showing today.
Listing is courtesy of: MIHARA & ASSOCIATES INC. (813-960-2300)
Listing Agent: Raymond Mihara (813-960-2300)
634 TIMBER BAY CIRCLE W, OLDSMAR, FL 34677
$324,90024 Days on yellowkey MLS ID: TB8489706
REDUCED by $4,100 (1.2%) on 04/04/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1056 Built: 1985 Tax: $4,283 (2025)Community: Shoreview Phase 2 Blk 6, Lot 3Single Family
Taxes:$4,283
Remarks: Move-In Ready Oldsmar Home! Welcome to this 3-bedroom, 2-bath home home located in the heart of Oldsmar, offering easy access to Tampa, Clearwater, Safety Harbor, and surrounding areas. This move-in ready property combines comfort, convenience, and a great outdoor living space. Inside you'll find a functional layout featuring an interior laundry area with upgraded Washer and Dryer(2023). Other recent upgrades include Refrigerator, Garbage Disposal, and Water Heater(2024) and a new Heat/Air System (2025). Granite and stainless steel in kitchen and updated Bathrooms. Step outside to enjoy a fully fenced, pet-friendly backyard designed for relaxing and entertaining. The outdoor space includes a large screened-in lanai and a spacious wood deck -perfect for barbeques, gatherings, or simply enjoying sunny Florida days. Also Minutes away from R.E. Olds Park which features an Amphitheater, Fishing pier, Picnic shelters, Playgrounds, Sand Volleyball and trails. Also occasionally through the year there are music concerts and festivals! This centrally located home offers the perfect blend of updates, outdoor living, and great accessibility. A great opportunity for buyers seeking comfort, convenience, and a welcoming place to call home. Property also remained safe and dry during the most recent Hurricanes and has never had any flooding issues in prior years either! Schedule your showing today!
Listing is courtesy of: AMERICAN HERITAGE REALTY, INC. (727-726-7272)
Listing Agent: Catherine Katopis (727-656-6862)
807 JACARANDA DR, OLDSMAR, FL 34677
$325,00017 Days on yellowkey MLS ID: TB8490680
0 Days Off yellowkey (back on 4/12/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1341 Built: 1986Monthly Fee: $35 Tax: $3,029 (2025)Community: Manors Of Forest Lakes The Ph 2Single Family
Taxes:$3,029
Remarks: Under contract-accepting backup offers. Welcome to your next smart move in Oldsmar. This 3-bedroom, 2-bathroom home with a 2-car garage checks the boxes that matter, and leaves room for you to make it your own without paying someone else’s design bill. Inside, you’ll find a functional split floor plan with the kitchen and living room right where they should be, in the heart of the home. It’s the kind of layout that just makes sense for everyday living, entertaining, or pretending you cook more than you actually do. The screened porch out back offers a solid space to relax, unwind, or enjoy Florida evenings without becoming a mosquito buffet. Now let’s talk honestly. This home could use a little glow-up. Think cosmetic updates, not a full-blown rescue mission. If you’ve been waiting for a chance to build some sweat equity and add your personal touch, this is it. The bones are there, and the upside is real. The yard is partially fenced, with some sections needing repair, and the roof, installed in 2002, is ready for your attention as well. It’s a great opportunity to roll improvements into your vision and truly make the home your own from top to bottom. Important updates you’ll appreciate: the AC was replaced in August 2022, so that’s one big-ticket item already handled. The property sits in a non-flood zone and stayed high and dry through both Hurricane Helene and Hurricane Milton, which says a lot. Located in a deed-restricted community with a low HOA of just $35 a month, you get a little structure without feeling over-managed. Bottom line, this is a solid starter home with good fundamentals, in a desirable area, priced with its potential in mind. If you’ve got vision and a little ambition, this one could turn into something really special. Come see it today!
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Quyen Le, Llc (813-409-7446)
600 S WOODLANDS DR, OLDSMAR, FL 34677
$409,99928 Days on yellowkey MLS ID: TB8488468
REDUCED by $15,001 (3.5%) on 04/12/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1952 Built: 1979Monthly Fee: $490 Tax: $4,813 (2025)Community: East Lake Woodlands Cluster HomesSingle Family
Taxes:$4,813
Remarks: One or more photo(s) has been virtually staged. This beautifully updated 3-bedroom, 2-bath attached villa style home is nestled in the highly sought-after Eastlake Woodlands community, offering serene preserve views in the front from your private fenced in patio and peaceful wooded and golf course views in the back. The home features a carport with a storage closet and a thoughtfully designed split-bedroom floor plan. Recent upgrades include all-new impact windows (2023), Roof (2020) a new air conditioner (2022), new washer & dryer (2022), remodeled entryway and bathrooms (2023), new blinds (2022), and remote-controlled ceiling fans throughout (2022). The living and dining areas showcase elegant crown molding, while the updated 150-amp electrical panel ensures modern efficiency. The kitchen boasts wood cabinetry, granite countertops, a glass mosaic backsplash, and stainless steel appliances. Laminate flooring extends throughout the home, with ceramic tile in the wet areas for added durability. The spacious primary suite offers a walk-in closet, access to the bonus room, and a luxurious bath with dual sinks, wood cabinetry, granite counters, and a step-in glass shower. The third bedroom also features a walk-in closet, built-in storage, and a slider to the bonus room, while the secondary bath includes a newer tile surround for the tub/shower and a stylish vanity with a granite countertop. Dont forget the huge, expansive bonus room that adds incredible flexibility for a family room, office, or hobby space. Perfectly blending comfort and style, this home delivers move-in-ready elegance in a premier location.
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)
Listing Agent: Jarod Brewer (727-647-1379)
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