Displaying: For Sale
Location: Oldsmar
Property Type(s): Single Family
Living Area Square Feet: 1000 to 1499
Do Not Show Listings
Oldsmar - 29 properties found
627 TIMBER BAY CIR W, OLDSMAR, FL 34677
$329,00025 Days on yellowkey MLS ID: TB8513485
2 Days Off yellowkey (back on 6/21/2026)
INCREASED by $19,000 (6.1%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1274 Built: 1984 Tax: $645 (2025)Community: Shoreview Ph 2Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$645
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. Pond View!!! Charming 3 bed / 2 bath ranch-style home (1,274 sq ft) in a peaceful, family-friendly neighborhood. Built in 1984, this light-filled residence offers a comfortable, single-level floor plan ideal for everyday living and easy entertaining. Enjoy serene pond views from the private backyard — a perfect quiet oasis for morning coffee or safe outdoor play. The home includes a two-car garage, ample parking, and a low-maintenance lot. Well-suited for families, commuters, or anyone seeking a relaxed Tampa Bay suburb lifestyle with quick access to shopping, schools, parks, and major roads. Move-in ready with great bones. With a little vision this property is a great sweet equity opportunity. Schedule a showing today to experience the setting and location in person.*New Roof Being Installed Next Week
Listing is courtesy of: MILLENNIAL REALTY & PROPERTY MGMT. (813-217-5691)
Listing Agent: Christopher Nelson (813-313-6338)
619 TIMBER BAY CIR E, OLDSMAR, FL 34677
$400,0004 Days on yellowkey MLS ID: TB8521146
0 Days Off yellowkey (back on 6/20/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1232 Built: 1983 Tax: $4,130 (2025)Community: Shoreview Ph ISpa: NoSingle Family
Taxes:$4,130
Elementary School: Oldsmar Elementary-PN
High School: East Lake High-PN
Middle School: Carwise Middle-PN
Remarks: Under contract-accepting backup offers. Former AirBNB is move in ready for Investor or Primary Home Owners! Smart buyers, take note: this move-in ready 3BR/2BA pool home has been thoughtfully updated: fresh interior and exterior paint (2026), a brand-new electrical panel (2026), hurricane-rated windows (2021), replaced ductwork (2021), gutters (2022), and an HVAC system (2018) maintained on a twice-yearly service plan. Sentricon termite protection is in place and serviced annually. Solar panels (2021) keep energy costs low and an EV charging outlet rounds out the practical extras.comes with an assumable flood insurance policy at the highest available coverage level, and you're stepping into meaningful savings from day one. Tucked behind conservation wetlands (Oldsmar Trail) with no rear neighbors — ever — this home offers a level of privacy and natural beauty that's hard to find at any price. Sip your morning coffee on the covered lanai while overlooking your private pool and the peaceful green belt beyond. The fully fenced, pool-ready backyard is made for Florida living — whether that means weekend entertaining or a quiet evening watching the sun set over the wetlands. A storage shed adds handy extra space for tools, pool equipment, or gear. Homes offering this combination of financial incentives, low-maintenance updates, and natural privacy don't come along often. Schedule your private tour today.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Colette Hughes (813-380-6583)
611 TANGERINE DR, OLDSMAR, FL 34677
$345,00025 Days on yellowkey MLS ID: TB8513141
REDUCED by $10,000 (2.8%) on 06/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1382 Built: 1980 Tax: $1,040 (2025)Community: Harbor Palms Unit ElevenSingle Family
Taxes:$1,040
Remarks: $5,000 seller credit offered to buyers!!Welcome to 611 Tangerine Drive a well-maintained 3-bedroom, 2-bathroom home located in one of Oldsmar’s most desirable and centrally located communities. Featuring a highly sought-after split floor plan, spacious living areas, and major system upgrades already completed, this home offers the perfect combination of comfort, functionality, and opportunity for a new owner to make the space their own over time. Inside, you’ll find tile flooring throughout the entire main living space, creating a clean, cohesive, and low-maintenance living environment. The split layout provides excellent separation between the primary suite and guest bedrooms, offering both privacy and flexibility for families, guests, or work-from-home living. The spacious primary suite features dual closets along with a beautifully updated master bathroom that adds a more modern touch to the home. The kitchen is equipped with stainless steel appliances and offers excellent functionality with ample cabinet and storage space, while still leaving room for future personalization and design possibilities to match your own style and vision. Several major improvements have already been completed for long-term peace of mind, including full-home repiping, a whole-house water softener and filtration system, and a durable Solar Shield metal roof designed for longevity, efficiency, and reduced maintenance for many years to come. The home has also never FLOODED! This provides additional confidence for future ownership. Outside, the screened-in porch creates the perfect place to relax and enjoy Florida’s year-round weather, while the newer fencing surrounds the backyard and offers both privacy and space for entertaining, pets, or outdoor enjoyment. A spacious two-car garage and abundant storage throughout the home further enhance everyday convenience. Located in the heart of Oldsmar, this property offers outstanding access to everything that makes the Tampa Bay area so desirable. Tampa International Airport, Clearwater Beach, Safety Harbor, Dunedin, and downtown Tampa are all within a convenient drive. Oldsmar is known for its excellent school district, strong community atmosphere, waterfront parks, scenic trails, playgrounds, nature preserves, and outdoor recreation. With its ideal location, major mechanical upgrades, flexible layout, and endless potential to further enhance and customize over time, 611 Tangerine Drive presents an exceptional opportunity in one of northern Pinellas County’s most sought-after communities.
Listing is courtesy of: AMERICAN HERITAGE REALTY, INC. (727-726-7272)
Listing Agent: Sid Vehabovic (727-657-4349)
347 COUNTRY CLUB DR, OLDSMAR, FL 34677
$429,000132 Days on yellowkey MLS ID: TB8475491
REDUCED by $20,000 (4.5%) on 04/05/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1280 Built: 1967 Tax: $1,515 (2024)Community: Oldsmar Country Club Estates Sec 1 RepSingle Family
Taxes:$1,515
Tax Year: 2024
Remarks: "Move-In Ready"... Freshly Painted and Beautifully completely Refurbished Single Family Pool Home, (3) Bedrooms, (2) Baths with plenty of storage space, vehicles, boat and golf cart(s) parking. Luxury vinyl flooring throughout this split plan homes interior, picturesque French Door views to the pool and lanai deck, all new kitchen appliances and home systems installed. An expansive corner lot property with plenty of green space, fenced yard and mature landscaping. Enjoy your Florida Lifestyle with family and social gatherings within the updated interior decor or outside in the screened pool and lanai deck area. We'll look forward to your visit.
Listing is courtesy of: PEOPLE'S CHOICE REALTY SVC LLC (813-933-0677)
Listing Agent: Frank Fundora (813-361-2505)
1924 MONTEGO CT, OLDSMAR, FL 34677
$359,90013 Days on yellowkey MLS ID: TB8517782
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1269 Built: 1980 Tax: $5,005 (2025)Community: Bayside Meadows-Phase ISingle Family
Taxes:$5,005
Remarks: **SUPER STARTER HOME!!** What a fantastic house for the price! From the moment you arrive, you’ll be wowed by the striking curb appeal. The freshly painted exterior is complemented by a newer roof and landscaping, with a 30-year dimensional shingle roof installed in 2024 and a transferable 10-year warranty. Inside, the spacious, open floor plan is just as impressive, starting with a leaded glass front door. This move-in ready home has been updated throughout, featuring a tiled great room with a lighted ceiling fan and a large front window that fills the space with natural light. The eat-in kitchen offers a cozy dinette, updated soft-close cabinetry, stainless steel appliances, recessed lighting, and tile countertops with backsplash. Down the hall are three bedrooms, all with lighted ceiling fans and new carpet. The primary ensuite boasts an updated bathroom with a walk-in shower and new hardware, while the guest bath offers resort-style features. Step through the back sliding glass door to a screened lanai with tile floors—perfect for relaxing or entertaining. The modest fenced backyard has fresh mulch and is easy to maintain. With a new A/C installed in 2022 and a prime location near trendy restaurants, shopping, AMC Woodlands Movies, and just minutes from Tampa, the airport, or the beach, this home truly has it all—don’t miss it! (house has never had any issues with flooding in 20 years owner has owned it)
Listing is courtesy of: RE/MAX REALTEC GROUP INC (727-789-5555)
Listing Agent: Shay Adelman (727-458-3702)
208 CUTLASS WAY, OLDSMAR, FL 34677
$350,00060 Days on yellowkey MLS ID: TB8501214
REDUCED by $20,000 (5.4%) on 04/29/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 2015Monthly Fee: $285 Tax: $3,417 (2025)Community: Hayes Park VillageSingle Family
Taxes:$3,417
Elementary School: Forest Lakes Elementary-PN
Remarks: NEW PRICE! Location, location, location is the key to finding the perfect home - and this one delivers on every level. If you have been searching for a place that blends character, convenience, and community, look no further. This charming 3-bedroom home sits in the picturesque neighborhood of Hayes Park Village, a community that feels like a slice of the French Quarter right here in Florida. Nestled in the heart of the City of Oldsmar, this home offers the best of old-world-charm with modern comfort. Oldsmar is a great City known for having more parks per sq. mile than any other city in the state along with excellent schools and an abundance of activities for all ages. Also, the home of Tampa Bay Downs and Tampa Bay Skating Academy. It is a place where community pride runs deep and quality of life comes naturally. The homes inviting wrap-around porch sets the tone from the moment you arrive. Enjoy your morning coffee as you look out to the neighborhood courtyard complete with a welcoming fire pit, creating the perfect setting for neighborhood gatherings. Inside the home, gleaming hardwood floors flow through an open concept living space that feels both spacious and cozy. The kitchen is beautifully appointed with granite countertops and 36" cabinets and a center island that anchors the room- ideal for cooking, entertaining or simply enjoying daily life. A convenient first floor powder room adds practicality for guest and family alike. The master suite opens to a second floor balcony that overlooks the lake and Richard B. Rogers Park. The Master bedroom also features a tray ceiling with crown molding and an upgraded bathroom with frameless glass shower enclosure and a walk-in closet. Two additional ample sized bedrooms and a guest bath complete the upstairs. THIS HOME HAS BEEN WELL MAINTAINED; ROOF IS JUST OVER A YEAR OLD AND THE AC IS JULY OF 2025, WATER HEATER REPLACED IN 2024. The PERFECT LOCATION connects TAMPA to PINELLAS COUNTY. Close commute to Tampa International Airport and International Mall. Within minutes of Clearwater and downtown Safety Harbor, Approximately 30 minutes to the Gulf Coast Beaches.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Jennifer Kashtan (813-310-7200)
442 EVERGREEN DR, OLDSMAR, FL 34677
$355,0007 Days on yellowkey MLS ID: TB8517079
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1190 Built: 1979 Tax: $5,386 (2025)Community: Harbor Palms Unit Eleven Lot 451Single Family
Taxes:$5,386
Remarks: Welcome to 442 Evergreen Drive, perfectly situated in one of Oldsmar's most desirable neighborhoods! This beautifully maintained residence offers the ideal combination of comfort, style, and Florida charm. Filled with abundant natural light, the spacious interior features a thoughtfully designed floor plan that seamlessly blends everyday living with effortless entertaining. Step outside and discover your own private backyard retreat, complete with a screened-in porch that provides the perfect setting for morning coffee, weekend gatherings, or simply unwinding after a long day. Freshly painted inside and out, this move-in-ready home showcases pride of ownership throughout and provides a fresh, inviting atmosphere from the moment you enter. Enjoy peace of mind knowing many of the home's major components have already been updated, including a Roof (2018), HVAC System (2018), Windows & Doors (2021), and Garage Door (2018). Conveniently located near beautiful parks, top-rated dining, shopping, entertainment, and the stunning Gulf beaches, this exceptional property offers the best of the Florida lifestyle. Whether you're looking for your first home, a growing family residence, or a place to enjoy your next chapter, 442 Evergreen Drive is ready to welcome you home. Showcasing exceptional maintenance, valuable updates, and a desirable screened-in porch for year-round enjoyment, this wonderful property offers a rare opportunity to enjoy comfortable Florida living in a prime Oldsmar location.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Sheri Boesch (727-776-3422)
1811 DRIFTWOOD CIR S, OLDSMAR, FL 34677
$359,90095 Days on yellowkey MLS ID: TB8488580
REDUCED by $10,100 (2.7%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1248 Built: 1973 Tax: $1,036 (2025)Community: Harbor Palms-Unit TwoSingle Family
Taxes:$1,036
Remarks: Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of Oldsmar! Offering 1,248 sq ft of well-designed living space, this move-in-ready property features a functional layout, abundant natural light, and modern updates throughout. Enjoy spacious living and dining areas that flow seamlessly, perfect for both everyday living and entertaining. The kitchen offers ample cabinetry and workspace, while the bedrooms are generously sized for comfort and flexibility. Conveniently located near parks, shopping, dining, and major roadways, this home provides easy access to Tampa, Clearwater, and surrounding areas. Don’t miss this opportunity to own a well-maintained home in a desirable location!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Julio Vasquez (727-404-8889)
316 COUNTRY CLUB DR, OLDSMAR, FL 34677
$325,00039 Days on yellowkey MLS ID: TB8508856
REDUCED by $3,900 (1.2%) on 06/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1344 Built: 1960 Tax: $616 (2025)Community: Oldsmar Country Club Estates Sec 3Single Family
Taxes:$616
Remarks: Yes! This beautifully renovated mid-century modern block home actually looks this good in person - no AI staging here! Located in the desirable NO HOA community of Oldsmar Country Club Estates. Timeless character with modern upgrades are inside this 3 bedrooms, 2 bathrooms. Under the exposed beams is 1,344 square feet of thoughtfully updated living space. The fully renovated kitchen features elegant quartz countertops, 42” upper cabinets, and stainless steel appliances, creating a stylish and functional space for everyday living and entertaining. Don't let the floor to ceiling windows fool you eco-friendly design allows a low-cost energy bill. Additional highlights and upgrades include: newer vinyl windows, a 2017 roof, 2023 ductless mini-split system, 2023 hot water heater, and updated electrical in 2025 for added peace of mind. Step outside to enjoy the fully fenced backyard, perfect for pets, entertaining, or relaxing in privacy. The attached carport provides convenient covered parking and additional storage flexibility. Ideally situated just yards from the Oldsmar Boat Ramp with direct access to Tampa Bay, this golf cart-friendly community offers the perfect Florida lifestyle. R.E. Olds Park is a 15-acre dog- friendly waterfront park featuring a 400 -foot fishing pier, playgrounds, picnic shelters, an amphitheater, and trails with scenic views of Tampa Bay. Named after automotive pioneer Ransom E. Olds, the park hosts numerous community events and offers amenities like volleyball, tennis & pickleball courts & restrooms. With no HOA restrictions, park the boats, RV’s and work trucks with ease. This property is ideal for a first-time homebuyer, seasonal resident, or as an income-producing short-term rental investment opportunity. Annual Flood quote $2,653.34
Listing is courtesy of: TMWRK BROKERAGE LLC (727-277-9032)
Listing Agent: Faith Walston (813-303-1239)
629 BAY LAKE TRL, OLDSMAR, FL 34677
$350,00013 Days on yellowkey MLS ID: TB8517300
1 Days Off yellowkey (back on 6/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1338 Built: 1984 Tax: $4,224 (2025)Community: Shoreview Ph 2Spa: NoSingle Family
Taxes:$4,224
Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of Oldsmar! Located in a desirable, golf-cart-friendly community with no HOA or CDD fees, this move-in-ready home remained HIGH & DRY during recent storms with no flood damage and includes attached insurance quotes for added peace of mind. Inside, you'll find fresh interior paint, brand-new luxury vinyl plank flooring (2026), updated lighting and ceiling fans, new blinds, and an inviting open layout perfect for everyday living and entertaining. The kitchen features all new appliances, including a new refrigerator, range, dishwasher, and microwave (2026). The spacious living area opens through new French doors to the outdoor living space. Step outside to your private backyard oasis with a screened lanai, new vinyl fence and gate (2024). Major updates include a 2019 roof, 2023 water heater, WiFi-enabled garage door opener, and tons more interior improvements throughout the home. Conveniently located near waterfront parks, pickleball courts, boat launches, shopping, dining, Safety Harbor, Tampa International Airport, and some of Florida's best beaches, this home offers the perfect blend of location, updates, and Florida lifestyle. Don't miss your chance to own this piece of paradise - schedule your showing today!
Listing is courtesy of: RE/MAX COLLECTIVE (813-438-7841)
Listing Agent: Heather Stotts Llc (951-505-6515)
2005 HUDSON CT, OLDSMAR, FL 34677
$310,00024 Days on yellowkey MLS ID: W7886259
REDUCED by $5,000 (1.6%) on 06/06/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1170 Built: 1982 Tax: $923 (2025)Community: Bayside Meadows Ph IiSingle Family
Taxes:$923
Remarks: Your dream home in Bayside Meadows Oldsmar, Florida, offers a single-family home with 2 bedrooms plus a garage conversion that could function as a third bedroom with the addition of a closet. The home includes a dining area with French doors leading to a screened lanai, an indoor laundry area, ceramic tile flooring in the main living spaces, and carpet in the bedrooms. You’ll see ceiling fans in every room, and a comforting kitchen that has room to add a center island. Outside, you’ll find a spacious screened lanai, a shed, a tropical oasis of landscaping, and a fenced yard. The property is conveniently close to beaches, parks, nature areas, and nearby airports. Located in northeastern Pinellas County at the top of Old Tampa Bay, Oldsmar features attractions such as Tampa Bay Downs, an ice-skating rink, a flea market, Sheffield Park, the BMX Supercross Track, Mobbly Bayou Beach Park, and Mobbly Wilderness Preserve, which offers hiking trails, kayak launches, and eco tours. The area also offers a variety of dining and shopping options, along with convenient access to medical facilities and a hospital.
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Gail Small (727-455-3057)
551 SALMON CT, OLDSMAR, FL 34677
$349,90053 Days on yellowkey MLS ID: TB8502478
1 Days Off yellowkey (back on 6/13/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1344 Built: 2002Monthly Fee: $70 Tax: $175 (2025)Community: Gull-Aire Village Ph 2CSingle Family
Taxes:$175
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to this well maintained single-family block home in Gull Aire Village, a friendly 55+ community known for low fees & great amenities. (not a manufactured home) With 2 bedrooms, 2 baths PLUS a 2 car garage, this home has been lovingly cared for & is truly move-in ready. Here are some of the fresh updates that will give you a great first impression: fresh exterior paint & mulch for curb appeal, fresh interior paint in Sherwin-Williams "Reflection" (a soft gray). There is a welcoming entry foyer with easy access to the great room & dining room. You will love the spacious, open layout of this interior with vaulted ceilings & a split-bedroom design that makes hosting guests extra comfortable. The kitchen is very neutral with gray Formica countertops & crisp white cabinetry. There are newer stainless-steel appliances, bright, neutral ceramic tile that matches the entry foyer and both baths. The sunny breakfast area with lots of natural light & a bay window with seating is a joy. The guest bedroom is at the front of the house with a bay window & plenty of room for your furnishing. The primary bedroom is a comfortable, generously sized retreat with space for a wide range of furniture, & the primary bath has double sinks, a large shower area & a huge walk-in closet. Step out back & relax in the enclosed rear lanai with windows for all year use, ceiling fans for a nice breezy space & a window A/C to keep things comfortable in the warmer months. The sliding doors from either the master bedroom or the great room lead right out to the lanai. From there, you can head out to the large paver patio that spans the width of the home - complete with retractable awnings for shade. For extra peace of mind, many of the big-ticket items have already been taken care of: Roof (2021), HVAC (2018), Water heater (2018), a Square D electrical panel, & a new service door on the side of the garage. Gull Aire Village is a very affordable retirement choice; monthly HOA fees only $70 per month & that gets you some great amenities! You have all these things to enjoy: a heated pool, hot tub/spa, shuffleboard courts, bocce ball, clubhouse for gatherings or playing pool, or cards, or a little work out, or read a book in the library. Golf carts are street legal within Gull Aire, so take a ride over to your friends house, join the Christmas parade or just tour the neighborhood when you feel like it. You can also walk along the paved path along the Tarpon outflow canal & hit the Oldsmar trail for an extended walk. Great location near (and walkable!) shopping & restaurants, movie theatre. Medical facilities & airports are nearby & the beautiful Gulf beaches are not far!! This is a great opportunity for someone looking to retire and live the easy life. Realtor is owner (this was my mothers home)
Listing Agent: Cathy Mccarthy (727-452-9339)
604 LIMETREE DR, OLDSMAR, FL 34677
$375,00062 Days on yellowkey MLS ID: O6401483
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1430 Built: 1980 Tax: $3,108 (2025)Community: Harbor Palms Unit ElevenSingle Family
Taxes:$3,108
Remarks: Welcome to this spacious and versatile home situated on a generously sized lot with extra space between neighboring properties, offering privacy and comfort. With NO HOA and NO CDD fees, you’ll enjoy the freedom to bring your boat, RV, and recreational toys. The spacious driveway accommodates plenty of vehicles. Inside, the designed split floor plan features three bedrooms, each with its own private bathroom and large walk-in closets . The home has undergone few recent renovations, while abundant storage can be found throughout. The converted garage has been transformed into a private suite with its own private entrance and a full bathroom with shower, creating an ideal in-law suite, guest quarters, home office, or potential income-producing rental opportunity. The kitchen features granite countertops and brand-new stainless steel appliances. Recent improvements also include impact-resistant windows and an additional bathroom. Step outside to enjoy the fully fenced backyard and screened patio. Elevated above the roadway, the property has remained high and dry through storms with no water damage, offering additional peace of mind. Residents also enjoy quick access to shopping, dining, entertainment, and major roadways. For beach lovers, Honeymoon Island, the Dunedin Causeway, Clearwater Beach, and the beautiful Gulf Coast shoreline are only a short drive away, offering some of the area’s most desirable beaches, boating, and waterfront recreation. Located in A-rated school zones, this home provides access to highly regarded schools.
Listing is courtesy of: JUPITER PROPERTIES, INC (386-547-6161)
Listing Agent: Sulamita Del Valle (813-510-9619)
549 LONGWOOD CIR, OLDSMAR, FL 34677
$515,00048 Days on yellowkey MLS ID: A4692285
REDUCED by $10,000 (1.9%) on 06/11/2026
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)
206 BEDFORD ST, OLDSMAR, FL 34677
$359,700192 Days on yellowkey MLS ID: TB8455925
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1274 Built: 1988 Tax: $3,766 (2025)Community: Oldsmar Rev MapSingle Family
Taxes:$3,766
Remarks: Virtually Staged. Short Sale. This beautifully updated, single-level home offers a smart, open layout with 3 bedrooms, 2 full baths, and a 2-car garage, designed for both everyday living and easy entertaining. Completely renovated in 2022, the interior has been thoughtfully updated and modernized. The main living area features high ceilings and an open floor plan that creates a bright, spacious feel. A striking fireplace accent wall anchors the living room and adds both character and warmth. Luxury vinyl plank flooring runs through the common areas, complemented by modern finishes throughout. The kitchen features granite countertops, stainless steel appliances, updated cabinetry, and a stylish backsplash, seamlessly connecting to the dining and living spaces. The split-bedroom floor plan provides privacy, and both bathrooms were updated with sleek tile in the showers and floors, new vanities, mirrors, and contemporary lighting. Additional features include a durable metal roof, a fully fenced backyard, and multiple outdoor living spaces. A screened-in porch offers a comfortable spot to unwind, while the expansive rear deck is ideal for entertaining or enjoying outdoor time year-round. Trustee sale, must sell!!
Listing Agent: Tanja Cisliek (727-480-4155)
1623 GRAY BARK DR, OLDSMAR, FL 34677
$419,90025 Days on yellowkey MLS ID: TB8512588
0 Days Off yellowkey (back on 6/9/2026)
REDUCED by $5,100 (1.2%) on 06/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1419 Built: 1997Monthly Fee: $13 Tax: $6,328 (2025)Community: Eastlake Oaks Ph 1Single Family
Taxes:$6,328
Remarks: Under contract-accepting backup offers. Welcome to 1623 Gray Bark Drive in the heart of Oldsmar! This well-maintained 3-bedroom, 2-bath home features a desirable split-bedroom floor plan offering both privacy and functionality. The kitchen has been updated with new countertops, while the refrigerator and microwave have both been recently replaced for added convenience. Major updates provide peace of mind, including a new roof in 2022, A/C in 2023 complete with a UV light sanitation system, interior paint refreshed in 2024, and a brand-new water heater installed in 2025. Step outside and enjoy a backyard designed for relaxation, complete with mature shaded trees creating the perfect setting for entertaining or unwinding after a long day. Residents enjoy extremely low HOA fees while still having access to fantastic community amenities including a pool, playground, and park area. Nature lovers and outdoor enthusiasts will appreciate the neighborhood trail leading directly to R.E. Olds Park, known for its scenic waterfront views, fishing pier, playgrounds, and community events. The home is also just 1.3 miles from Oldsmar Sports Complex, offering sports fields, pickleball courts, playgrounds, walking trails, and recreational activities for all ages. Conveniently located near shopping, dining, and Tampa Bay area attractions, this home combines comfort, updates, and lifestyle all in one.
Listing Agent: Tamara Wilson (727-743-1501)
413 COUNTRY CLUB DR, OLDSMAR, FL 34677
$349,70081 Days on yellowkey MLS ID: O6396122
REDUCED by $100 (0.0%) on 06/05/2026
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: **Seller is offering Assistance to Buyer's Closing Costs/Buy Down Rate** 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)
304 PATTY DR, OLDSMAR, FL 34677
$397,00059 Days on yellowkey MLS ID: TB8500425
1 Days Off yellowkey (back on 6/1/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1344 Built: 1960 Tax: $3,150 (2025)Community: Oldsmar Country Club Estates Sec 3Single Family
Taxes:$3,150
Remarks: Under contract-accepting backup offers. Incredible Opportunity in Oldsmar! Potential for Water Views and Coastal Lifestyle Discover the perfect canvas for your next dream home or investment project in this single-family property located in the coveted Oldsmar Country Club Estates subdivision. Situated on a generous lot of approximately 1/4 acre (10,054 square feet), this residence offers an unbeatable location just across the street from the Oldsmar boat ramp and the beautiful Mobbly Bayou. 3 bedrooms and 2 full bathrooms spread over 1,344 square feet of living space. It has a large family/multipurpose room of 450 sq. ft. and plenty of storage space. The house has newer windows and a recent metal roof. The current structure allows for renovation or upward construction to capture spectacular water views from a second level. Enjoy the true Florida lifestyle with immediate access to launch your kayak or boat. The property is highly walkable to several waterfront parks, including R.E. Olds Park, Bicentennial Park, and Veterans Memorial Park, where you will find dog areas, pickleball courts, and playgrounds. There is no HOA or CDD, offering maximum flexibility for the owner. Located in Pinellas County, with easy access to local amenities in Oldsmar and major routes to Tampa and Clearwater.
Listing is courtesy of: SELLING USA, LLC (813-723-0086)
Listing Agent: Eleydi Alvarez Lopez, Llc (813-585-2717)
1705 IRONWOOD CT E, OLDSMAR, FL 34677
$320,000102 Days on yellowkey MLS ID: TB8486052
REDUCED by $10,000 (3.0%) on 05/26/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1206 Built: 1973 Tax: $1,600 (2025)Community: Harbor Palms-Unit SixSingle Family
Taxes:$1,600
Remarks: Welcome to this beautifully renovated 2-bedroom, 2-bathroom home—perfect for first-time buyers or those looking to downsize without sacrificing comfort. The stunning kitchen, remodeled last year, features elegant quartz countertops and new stainless steel appliances, creating a modern and inviting space for cooking and entertaining. Just off the kitchen, you'll find a very spacious area that can easily serve as a family room, home office, or versatile flex space to suit your lifestyle. Step outside to enjoy the large backyard—perfect for relaxing, gardening, or hosting gatherings. Situated on a quiet street, this cozy yet stylish home is truly move-in ready. According to the owners, the A/C was replaced in August 2018 and the roof was replaced in June 2025, providing added peace of mind for the new owner. Don’t miss this opportunity to own a beautifully updated home with modern finishes and plenty of space to enjoy.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Aned Pantoja (813-264-7754)
1912 CUTTY BAY CT, OLDSMAR, FL 34677
$325,00034 Days on yellowkey MLS ID: TB8509310
1 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1080 Built: 1984 Tax: $2,313 (2025)Community: Sheffield Village Ph Ii At Bayside MeadowsSingle Family
Taxes:$2,313
Remarks: Must see this beautiful 3 bedroom, 2 bathroom, 1 car garage pool home ideally situated in the highly desirable Sheffield Village at Bayside Meadows in Oldsmar. Location truly speaks for itself with direct access to one of Oldsmar’s premier parks. Sheffield Park offers tennis courts, baseball fields, basketball courts, walking and biking trails, a dog park, disc golf, playground, kayak launch, picnic shelters, and restrooms. Tucked away on a quiet cul-de-sac, this charming home showcases exceptional pride of ownership from the moment you arrive. Inside, the thoughtfully designed floor plan features a spacious family room with soaring cathedral ceilings that flows seamlessly into the updated eat in kitchen complete with wood cabinetry, granite countertops, tiled backsplash, and newer stainless steel appliances. The primary suite features a spacious closet and a beautifully renovated ensuite bathroom, while two additional bedrooms share an updated full bathroom. French doors lead to an oversized patio and private backyard oasis featuring a built in pool, perfect for entertaining and relaxing year round. Additional updates include HVAC 2022, roof estimated 2011, water filtration system, and a fully fenced yard with vinyl fencing, double gate access, and plenty of room for your boat, trailer, or recreational toys. NO HOA. Conveniently located near shopping, dining, Honeymoon Island Beach, Caladessi Island State Park, Clearwater Beach, John Chestnut Sr. Park on Lake Tarpon, and the Pinellas Trail. Don’t miss this incredible opportunity to own a beautiful pool home in one of Oldsmar’s most sought after communities.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Linda Caruso (727-410-7501)
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