Location: Oldsmar
Do Not Show Listings
513 OAKWOOD BLVD, OLDSMAR, FL 34677
$535,000148 Days on yellowkey MLS ID: TB8452178
2 Days Off yellowkey (back on 4/14/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1764 Built: 1975 Tax: $2,042 (2024)Community: Oldsmar Rev MapSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,042
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. Welcome home to this beautifully remodeled 3-bedroom, 2-bath pool home in the heart of Oldsmar. Recently updated and truly move-in ready, this home offers modern finishes, comfortable living spaces, and an ideal location close to the waterfront. Step inside to an inviting open layout featuring new luxury vinyl flooring throughout and a beautifully updated kitchen with new cabinets, countertops, and appliances. Additional updates include a new water heater, 2020 roof, 2024 pool resurfacing and 2018 AC for added peace of mind. Natural light fills the home, creating a bright and welcoming atmosphere in every room. The outdoor space is equally impressive. Enjoy the refreshing screened-in pool and the large screened patio, perfect for relaxing or entertaining. The spacious yard provides plenty of room to play, garden or unwind. Surrounded by mature landscaping and a variety of Florida native plants creating a peaceful private setting, perfect for watching the birds that visit the garden. Just around the corner is R.E. Olds Park, a 15-acre park offering beautiful waterfront views, playgrounds, walking trails, an open-air amphitheater, community events, and a fishing pier along the bay. With its extensive upgrades, inviting outdoor areas, and desirable location, this home beautifully blends modern updates with classic Florida charm.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Marissa Barrett (941-961-4164)
106 LAKESIDE CT, OLDSMAR, FL 34677
$158,000389 Days on yellowkey MLS ID: TB8350281
REDUCED by $2,000 (1.3%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1981 Tax: $2,932 (2024)Community: East Lake Woodlands CondoCondo
Taxes:$2,932
Remarks: Great Value!! This Condo is located within the Gated community of East Lake Woodlands. This unit is on the second floor and features an eat in kitchen, living/dining room with sliders out to the screened lanai, split bedroom plan, the primary suite has a walk-in closet, a secondary closet and a linen closet. The primary bath has a step in shower. The guest suite has a bath off the hallway. The laundry closet is located on the lanai & includes a washer/dryer. Covered parking 1 space under carport. Unit is located across from the Pool! This unit needs your attention & priced to offset reno to make it your own. Great rental, primary residence or winter getaway..No waiting period for a buyer to rent the condo. Excellent opportunity!
Listing is courtesy of: TAMPA BAY SIGNATURE PROPERTIES, LLC (727-692-2847)
Listing Agent: Christi Watson (727-692-2847)
1598 LOCKMEADE PL, OLDSMAR, FL 34677
$999,90032 Days on yellowkey MLS ID: TB8490836
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
Elementary School: Forest Lakes Elementary-PN
High School: East Lake High-PN
Tax Year: 2025
Middle School: Carwise Middle-PN
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)
1527 WOODSTREAM DR, OLDSMAR, FL 34677
$599,00066 Days on yellowkey MLS ID: TB8476648
0 Days Off yellowkey (back on 3/28/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1919 Built: 1996Monthly Fee: $470 Tax: $3,762 (2025)Community: Cross Creek - Unit TwoSingle Family
Taxes:$3,762
Remarks: Under contract-accepting backup offers. Immaculate Home in Popular Cross Creek within East Lake Woodlands Golf and Country Club Community. This Devonshire Model offers 2 Bedrooms, 2 Baths, Den/Study, 2 Car Garage, and Serene Views of the Fountain and Pond! A soft flow and clean lines adorn this home. Features include Luxury Vinyl Flooring throughout interior with Travertine on the Lanai, Hurricane Rated Weather Tight Windows and Glass Siding Doors, Hurricane Rated Garage Door, Epoxy Flooring and More Storage Shelving added in Garage, and a Generac Generator for electric outages during storms. The Kitchen provides Custom Cabinets, Quartz Counter Tops and Back Splash, Large Sink, NEWER Refrigerator, and Dishwasher, Closet Pantry, Built in Desk and Eat in Kitchen with views of the garden. The Living Room and Dining area are spacious with lots of natural light and opens to a comfortable Screen Enclosed Lanai with views of the pond and the plush landscaping. The Primary Bedroom offers His and Her Walk in Closets, a Separate Seamless Glass Shower Stall, Garden Tub, Custom Cabinets, Marble Counters, His and Her Vessel Sinks, and Private Water Closet. The Second Bedroom and Bathroom are perfect for Guests: keeping with the color scheme and quality of the kitchen - Quartz Counters, Custom Cabinets and Fixtures, NEWER Shower Stall with Seamless Glass Sliding Doors and Decorative Tile. The Laundry Room has a Utility Sink, NEWER Washer and Dryer, Quartz Counter Tops and Cabinets for more storage room. The Den/Study provides a Built In-Home Office Center with plenty of room for more furniture. NEWER Exterior and Interior Paint, NEWER Light Switches and Canned Lighting Fixtures updated, *AC 2020, Garage Door 2023, LVP Flooring 2022, Windows/Doors 2023, Roof 2019, Sprinklers 2023, New Drain Pipes House to Street 2021, Ring Door Bell 2023.* The monthly maintenance fees include: Cable TV, Grounds Care - Fertilizing, Mowing, Trimming and Mulching Flower Beds, Trash Collection, Heated Community Pool and Spa, Escrow Reserves, Pressure Cleaning of Roof and Painting the Exterior of your home every 7 years. East Lake Woodland's Ardea Country Club provides Resort Style Amenities with additional fees that include Golf, Fitness Center, Tennis, Olympic Swimming Pool, Sport Shop, Lounge and Bar, Restaurant and Activities for the Entire Family!
Listing is courtesy of: PREFERRED REALTY GROUP, LLC (727-418-1020)
Listing Agent: Sandy Harris (727-365-3930)
62 EMERALD BAY DR, OLDSMAR, FL 34677
$220,000101 Days on yellowkey MLS ID: TB8465225
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1264 Built: 1994Monthly Fee: $283 Tax: $3,024 (2024)Community: Emerald BayTownhouse
Taxes:$3,024
Elementary School: Oldsmar Elementary-PN
Remarks: Heart of Oldsmar convenient to restaurants, shopping and Tampa. 2 Story, 2 Bedroom / 2.5 Bathroom Townhome in Oldsmar, AC 7/23, newer luxury vinyl flooring and newer paint.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Lin Huang (727-417-5186)
244 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677
$220,000101 Days on yellowkey MLS ID: TB8465176
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1110 Built: 1996Monthly Fee: $454 Tax: $3,637 (2024)Community: Countryside KeyTownhouse
Taxes:$3,637
Elementary School: Curlew Creek Elementary-PN
Remarks: Cozy 2-Bedroom, 2.5-Bath Townhome in the heart of Oldsmar. Brand new fresh carpets. The monthly HOA fees cover a wide range of services, including water, sewer, trash, cable, wifi, community pool, lawn and landscaping, roof maintenance and replacement, exterior pest control, and exterior building maintenance. Enjoy the convenience of being just minutes from the shopping, dining, a movie theater, parks, bike trail and more.
347 CANAL WAY, OLDSMAR, FL 34677
$199,000192 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)
303 MEADOW LN, OLDSMAR, FL 34677
$190,00014 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
$249,900207 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)
2270 CHRISTY LN, OLDSMAR, FL 34677
$1,250,00068 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)
904 VINEYARD LN, OLDSMAR, FL 34677
$340,00063 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
$199,99925 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)
172 LAKEVIEW WAY #172, OLDSMAR, FL 34677
$165,00017 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
$258,000103 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)
2208 SUNSET WIND LOOP, OLDSMAR, FL 34677
$365,000182 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
$649,99918 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)
807 JACARANDA DR, OLDSMAR, FL 34677
$325,00027 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)
112 BRENT CIR, OLDSMAR, FL 34677
$499,000112 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)
140 BRENT CIR, OLDSMAR, FL 34677
$565,000178 Days on yellowkey MLS ID: O6357016
REDUCED by $35,000 (5.8%) on 04/11/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 1791 Built: 2002Monthly Fee: $475 Tax: $3,527 (2024)Community: Seaside EstatesTownhouse
Taxes:$3,527
Remarks: Seller Motivated! Asking price is under last appraisal value. Come take a look at this beautiful 3 bedroom, 3 bath bay front townhome overlooking Old Tampa Bay and Safety Harbor. Seaside Estates is a gated community, located in the heart of Oldsmar, which offers may options for access to the water, as well as major thoroughfares. 3 Car tandem garage that walks out to a beautiful view, the common area and boat docks. This unit owns Slip 12, with a cover and brand new $17,000 boat lift. One of two grandfathered in with covered biminy top. Stainless Steel appliances, wood flooring, renovated spare bathrooms, and spacious balconies from the great room, and the primary bedroom as well. A wood burning fireplace is also located in the primary bedroom for those cosy nights overlooking the water. The spacious floor plan beautiful water views. Seaside estates is a golf cart-friendly community, offering amenities such tennis and pickelball courts, a swimming pool and Jacuzzi. There is a dock area that offers fishing opportunities and houses the particular residents that own boat docks. Located on a few minutes away from waterfront public parks, recreational facilities, and restaurants. 20 events annually are hosted by the community annually, with monthly dinners strategically planned around the scenic Tampa Bay. This neighborhood is just minutes from downtown Oldsmar and Safety Harbor which have a variety of restaurants, nightlife, street and music festivals, walking and biking trails, kayaking, Seaside estates is also pet friendly. 20 min to Caladesi State Park and the pristine Honeymoon Island and 20 minutes to Tampa Airport and 30 minutes to downtown Clearwater. Come take a look at this waterfront gem. Some of these photos have been virtually staged.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Nicci Meyer, Pa (407-913-1131)
1732 SPLIT FORK DR, OLDSMAR, FL 34677
$585,00054 Days on yellowkey MLS ID: TB8482923
0 Days Off yellowkey (back on 4/11/2026)
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2163 Built: 1997Monthly Fee: $13 Tax: $9,151 (2025)Community: Eastlake Oaks Ph 1Spa: YesSingle Family
Taxes:$9,151
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully updated home in the highly desirable Eastlake Oaks community of Oldsmar, where comfort, privacy, and location come together perfectly. NO FLOOD INSURACE REQUIRED. This 3-bedroom, 2.5-bath home with a rare 3-car garage offers stunning water views and no rear neighbors, creating a peaceful setting that’s hard to find. Inside, the home has been meticulously upgraded throughout, making it completely move-in ready. Enjoy a beautifully renovated kitchen, updated bathrooms, new flooring, and fresh interior paint, all designed to create a modern and inviting living space. The open layout flows perfectly for both everyday living and entertaining while allowing you to enjoy the tranquil water views from the back of the home. Major updates provide peace of mind for years to come, including a new water heater (2024), HVAC system (2022), and roof (2019). One of the most exceptional features of this home is that it is one of only a handful of properties in the entire neighborhood that does NOT require flood insurance, offering significant long-term savings while still enjoying a beautiful water view setting. Located in one of Oldsmar’s most desirable neighborhoods, Eastlake Oaks is known for its welcoming community feel and convenient access to top-rated schools, parks, shopping, dining, Tampa International Airport, and the Gulf beaches. Homes with this combination of water views, privacy with no rear neighbors, extensive upgrades, a 3-car garage, and no flood insurance requirement are incredibly rare. Don’t miss your opportunity to own this exceptional home in a fantastic neighborhood.
Listing is courtesy of: COLDWELL BANKER REALTY (813-253-2444)
Listing Agent: Jonathan Hernandez (727-417-1122)
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