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Oldsmar, FL Homes for Sale under $400,000

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  • /22

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft

    106 Cutlass Way, Oldsmar, FL 34677

    Fully updated and move-in ready 3-bedroom, 2.5-bath townhome in highly desirable Hayes Park Village. Built in 2016, this home offers modern finishes throughout, including luxury plank vinyl flooring, updated bathrooms, granite countertops, stainless steel appliances, and wood cabinetry. Crown molding adds an elegant touch to the downstairs living area, while modern lighting and ceiling fans are

    Agent Photo

    Rachel Mayhew

    RE/MAX CHAMPIONS

    (656) 240-4710

    106 Cutlass Way, Oldsmar, FL 34677
  • /52

    $399,999

    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft

    370 S Woodlands Dr, Oldsmar, FL 34677

    Virtually Staged some photos. Price Reduction!! Seller offering a $5,000 credit towards buyers closing costs. Attention all Golfers and Tennis players Dream in East Lake Woodlands that showcases 2 Championship 18 hold golf courses and 14 HAR-Tru tennis courts with no membership required!!.Newly remolded Patio Home with 2 bedroom 2 full bathroom with possible office/dining area in the Golf Course

    Agent Photo

    Michele Davis

    27NORTH REALTY

    (813) 536-4186

    370 S Woodlands Dr, Oldsmar, FL 34677
  • /37

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,133 Sq Ft

    313 Congress St, Oldsmar, FL 34677

    Charming, Move-In Ready Home — Never Flooded, Beautifully Updated, and Priced to Sell!Welcome to 313 Congress St — a hidden gem that combines modern updates with timeless Florida charm. This lovingly maintained 3-bedroom, 2-bath home has been thoughtfully cared for and upgraded throughout, offering true peace of mind for its next owner.Enjoy major improvements where it matters most: a new

    Agent Photo

    Jessica Christianson

    EXP REALTY LLC

    (656) 223-6662

    313 Congress St, Oldsmar, FL 34677
  • /11

    $325,000

    • Land
    • 0.35 Acre
    • $928,571 per Acre

    505 Federal St, Oldsmar, FL 34677

    Home Sites Available in Oldsmar, FL! Own a piece of prime real estate in the highly sought-after location of downtown Oldsmar, FL located halfway between Tampa Bay and Pinellas county beaches. This home site offers a fantastic opportunity for investors and homeowners to build their dream residences in a desirable area on a quiet and peaceful dead end street. This oversized 100x150 home site is

    Agent Photo

    John Blaeser

    BHHS FLORIDA PROPERTIES GROUP

    (813) 565-9394

    505 Federal St, Oldsmar, FL 34677
  • /73

    $365,000

    • 2 Beds
    • 2 Baths
    • 1,106 Sq Ft

    303 Shore Dr W, Oldsmar, FL 34677

    IMPROVED PRICE! BRING ALL OFFERS. WATER VIEWS! On over 1/3 of an Acre of Land! Property took on water during Hurricane Helene. Seller has removed bottom 4 feet of drywall from interior walls. This could be made into your dream home or become an INCREDIBLE INVESTMENT OPPORTUNITY. SOLD AS-IS and PRICED ACCORDINGLY. This solid block 2 Bed, 2 Bath Home, located in Tranquil Oldsmar has it all! Located

    Ena Ebanks FUTURE HOME REALTY INC

    303 Shore Dr W, Oldsmar, FL 34677
  • /15

    $359,000

    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    1223 Clays Trail, Oldsmar, FL 34677

    This property is one of a kind and the seller is motivated! This spacious 2600 square foot, 4 bedrooms, 2.5 bath, 1 car garage townhome is located in the very popular, highly sought after Eastlake Woodlands Golf and Country Club community. With an open floor plan, custom lighting in the great room, and double master bedrooms,-one on each floor with bay windows and plantation blinds, this

    Stephen Hachey REALTY OF RIVERVIEW LLC

    1223 Clays Trail, Oldsmar, FL 34677
  • /29

    $325,000

    • 2 Beds
    • 2 Baths
    • 1,237 Sq Ft

    215 Clays Trail, Oldsmar, FL 34677

    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

    Whitney Parks RE/MAX COLLECTIVE

    215 Clays Trail, Oldsmar, FL 34677
  • /34

    $329,000

    • 2 Beds
    • 2 Baths
    • 1,910 Sq Ft

    1227 Clays Trail Unit 301, Oldsmar, FL 34677

    Take advantage of ideal market timing with this low-maintenance, townhome-style condo offering serene pond views in the highly desirable East Lake Woodlands community—a gated enclave known for its beautifully maintained homes and lush Florida landscaping. Located on the second level, this residence features a private courtyard entry leading to stairs that open into an expansive, light-filled

    Julie Jones SMITH & ASSOCIATES REAL ESTATE

    1227 Clays Trail Unit 301, Oldsmar, FL 34677
  • /49

    $338,000

    • 2 Beds
    • 2 Baths
    • 1,502 Sq Ft

    40 Gretchen Ct, Oldsmar, FL 34677

    SELLER FINANCING WITH ACCEPTABLE OFFER! Step through the front door of this charming villa, and you feel at home. The welcoming open floorplan unfolds with a view of a huge outdoor lush grassy area - no close backyard neighbors! Move from the foyer and dining area, through the great room into the enclosed, insulated and completely air-conditioned 250 SqFt Florida/bonus room, making this one of

    Debra Gross BHHS FLORIDA PROPERTIES GROUP

    40 Gretchen Ct, Oldsmar, FL 34677
  • /52

    $390,000

    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft

    1909 Castle Bay Ct, Oldsmar, FL 34677

    --GREAT CURB APPEAL--Discover this IMMACULATE 3-bedroom, 2-bath home with garage located on a quiet cul-de-sac in the heart of Oldsmar. BEAUTIFUL HIGH GLOSS TILE FLOORING THROUGHOUT Featuring spacious living areas with vaulted ceilings, a primary bedroom with an ensuite, and a split bedroom layout for added privacy and a rear screened porch perfect for relaxing or entertaining. The home has been

    Craig Berenger, Jr KELLER WILLIAMS REALTY- PALM H

    1909 Castle Bay Ct, Oldsmar, FL 34677
  • /38

    $339,900

    • 2 Beds
    • 2 Baths
    • 1,187 Sq Ft

    1712 Azalea Ct Unit B, Oldsmar, FL 34677

    Welcome to 1712 Azalea Court B in the heart of Oldsmar — a hidden gem just minutes from world-class beaches, top-rated golf courses, and some of the best attractions Tampa Bay has! This beautifully maintained home offers the perfect blend of comfort and convenience, nestled on a quiet cul-de-sac with no rear neighbors. Whether you’re looking for a full-time residence, vacation home, or

    Bert Calebro CALEBRO & ASSOCIATES

    1712 Azalea Ct Unit B, Oldsmar, FL 34677
  • /30

    $329,900

    • 3 Beds
    • 2 Baths
    • 1,044 Sq Ft

    3164 Duane Ave, Oldsmar, FL 34677

    ***BACK ON MARKET, BUYER'S FINANCING FELL THROUGH*** Welcome to your next home in the vibrant community of Oldsmar! This inviting 3-bedroom, 2-bathroom residence blends comfort, functionality, and a fantastic location near outdoor recreation and local favorites. As you arrive, you're greeted by a welcoming exterior that sets the tone for what’s inside. Step into the spacious living room featuring

    Valeria Aliaga NETWORTH REALTY OF TAMPA, LLC

    3164 Duane Ave, Oldsmar, FL 34677
  • /39

    $390,000

    • 3 Beds
    • 2.5 Baths
    • 1,667 Sq Ft

    2208 Sunset Wind Loop, Oldsmar, FL 34677

    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,

    Yael Hatfield KELLER WILLIAMS TAMPA PROP.

    2208 Sunset Wind Loop, Oldsmar, FL 34677
  • /20

    $339,900

    • 3 Beds
    • 2 Baths
    • 1,668 Sq Ft

    114 Clays Trail Unit 114, Oldsmar, FL 34677

    Light and bright 3BED/2BA Condominium with attached garage. Vaulted ceilings, potting shelves, sky-lites, and sunburst windows! Elegant living/dining room, posh master bath with shower and separate steeping tub. Split bedroom plan, spacious eat-in kitchen with Oak cabinetry and breakfast bar. Extensive tile flooring, tiled and screened in lanai, tranquil pond views and nature galore! East Lake

    George Kolistopoulos ADVANCED REALTY GROUP INC

    114 Clays Trail Unit 114, Oldsmar, FL 34677
  • /10

    $323,000

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    1206 Sawgrass Ct, Oldsmar, FL 34677

    This 3 bedroom 2 full bath home boasts of a vaulted ceiling in the living room area, inside laundry and en suite bath attached to your primary bedroom. The second full bath is located between your other 2 bedrooms with access from the living area. Equipped with built in stove and dishwasher; the refrigerator also conveys to the new owner with the property. Nearby community pool and hot tub and

    Barbara Webb CHARLES RUTENBERG REALTY INC

    1206 Sawgrass Ct, Oldsmar, FL 34677
  • /38

    $319,900

    • 2 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    315 Woods Landing Trail, Oldsmar, FL 34677

    Completely updated, water view townhome within the 24hr guard gated, golf cart friendly, country club community of East Lake Woodlands! This home has been updated, barely used, meticulously kept and has it all: 2 bedrooms (the master bedroom offers an amazing water view) each with en suite full bathrooms and walk in closets, plus an additional half bathroom downstairs, inside laundry, a charming

    Shannon Perrott MIHARA & ASSOCIATES INC.

    315 Woods Landing Trail, Oldsmar, FL 34677
  • /27

    $359,000

    • Land
    • 0.91 Acre
    • $394,505 per Acre

    0 Strathmore Ave, Oldsmar, FL 34677

    Discover the potential of this rare, untouched piece of land located in the heart of charming Oldsmar. Whether you're planning to build your forever home or exploring investment opportunities—like developing rental properties—this lot offers incredible flexibility. With just under an acre to work with and no HOA restrictions, you're free to bring your vision to life without limitations. The

    Jurandir Alves ALIGN RIGHT REALTY CARROLLWOOD

    0 Strathmore Ave, Oldsmar, FL 34677
  • /44

    $399,000

    • 1,978 Sq Ft

    3133 Huron Ave, Oldsmar, FL 34677

    EXECUTIVE SUMMARYFANTASTIC OLDSMAR LOCATION. Motivated Seller!! These 2 units are occupied one on a month-to-month lease and the second with a long-term lease ending 7/26. These 1019 sq ft units each have 3 bedrooms 2 bathrooms open spacious living room/dining room/kitchen area, a breakfast bar, and separate washer/dryer hook-up in each unit. Interior renovations were made a few years ago and

    Joe Strong REAL PROPERTY MANAGEMENT TAMPA ST. PETE

    3133 Huron Ave, Oldsmar, FL 34677
  • /25

    $395,000

    • 3 Beds
    • 2 Baths
    • 1,607 Sq Ft

    1802 Forest Dr, Oldsmar, FL 34677

    Welcome to Highly Sought-After Harbor Palms!This stunning 3-bedroom, 2-bathroom POOL home offers true Florida living at its finest witha private inground pool, spacious layout, and exceptional indoor-outdoor flow.Step inside and you’re greeted by a bright and inviting living room featuring a cozy fireplaceand skylight, creating a warm, welcoming ambiance. The formal dining

    Jeff Jones MARK SPAIN REAL ESTATE

    1802 Forest Dr, Oldsmar, FL 34677
  • /50

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,547 Sq Ft

    311 Vista Cruiser Ln, Oldsmar, FL 34677

    This stunning 3-bedroom, 2.5-bath townhome offers the perfect blend of style, comfort, and peace of mind. Outfitted with hurricane shutters, impact windows, and a hurricane-rated garage door, the home ensures lasting security while sitting just moments from local fire stations for added reassurance. A brick-paved walkway and covered front porch create a warm welcome, leading into an inviting

    Vanessa Leonard KELLER WILLIAMS REALTY- PALM H

    311 Vista Cruiser Ln, Oldsmar, FL 34677
  • /33

    $319,000

    • 4 Beds
    • 2 Baths
    • 1,550 Sq Ft

    20 Sylvia Place, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. This is a 4-bedroom, 2-bath villa in a gated community with a brand-new roof (installed February 2025), nearly new AC (2024), and enough space for the grandkids to actually visit without everyone being on top of each other.And here's the best part: your HOA fee of $440/month covers exterior maintenance and painting, your roof, lawn care, cable

    Kera Arnone CHARLES RUTENBERG REALTY INC

    20 Sylvia Place, Oldsmar, FL 34677
  • /27

    $330,000

    • 3 Beds
    • 2.5 Baths
    • 1,525 Sq Ft

    403 E Tuscan Ln E, Oldsmar, FL 34677

    Welcome home in Oldsmar, FL! This two-story 1,525 square foot townhouse, located in the HIGHLY-desirable gated community of "Tuscany Woods", was built in 2015 and has 3 bedrooms and 2.5 bathrooms. The first floor offers an open floor plan, which seamlessly connects the living, dining, and kitchen areas, making it an ideal space for entertaining friends or simply relaxing. The tile flooring

    Kirk Ray Smith 54 REALTY LLC

    403 E Tuscan Ln E, Oldsmar, FL 34677
  • /31

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft

    1820 Driftwood Cir N, Oldsmar, FL 34677

    WONDERFUL 3-BEDROOM, 2-BATH SCREENED POOL HOME PRICED IN THE 300s, LOCATED IN THE DESIRABLE HARBOR PALMS SUBDIVISION. THE HOME FEATURES AN EXCELLENT SPLIT-BEDROOM FLOOR PLAN, A SPACIOUS LIVING ROOM, A COMFORTABLE FAMILY ROOM, AND GENEROUSLY SIZED BEDROOMS. ENJOY A SCREENED-IN POOL AND AN OVERSIZED ONE-CAR GARAGE.RECENT UPDATES INCLUDE A NEW A/C (2022), NEW ELECTRICAL PANEL (2023), AND A ROOF

    Frank Acerra SELECT PROPERTIES INC

    1820 Driftwood Cir N, Oldsmar, FL 34677
  • /70

    $360,000

    • 2 Beds
    • 2 Baths
    • 1,785 Sq Ft

    10 Woodridge Cir, Oldsmar, FL 34677

    RARE AND DESIRABLE END UNIT ON AN OVERSIZED AND BEAUTIFULLY LANDSCAPEDCORNER LOT! Welcome to the private, gated golf course community of East LakeWoodlands and this special open concept townhome with peaceful, sweeping views ofnatural foliage and the well-manicured golf course. The living space soars with volumeceilings and offers a cozy corner fireplace and plenty of natural

    John Erik Savitsky ENGEL & VOLKERS ST. PETE

    10 Woodridge Cir, Oldsmar, FL 34677
  • /78

    $379,000

    • 4 Beds
    • 2 Baths
    • 1,253 Sq Ft

    648 Timber Bay Cir E, Oldsmar, FL 34677

    Discover your own slice of paradise with this beautifully updated 4-bedroom, 2-bath home, perfectly situated to capture the sights and sounds of nature. Step into the expansive screened-in lanai, where a soothing hot tub and breathtaking water views set the stage for unforgettable gatherings with family and friends. Inside, the spacious open-concept living area seamlessly connects to the eat-in

    Brenda Ayala GENSTONE REALTY

    648 Timber Bay Cir E, Oldsmar, FL 34677
  • /43

    $359,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    316 Country Club Dr, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Step into this mid-century modern 3-bedroom, 2-bath home in Oldsmar, where clean lines, large windows, and a connection to the outdoors create a style that never goes out of season. The architecture brings in that classic mid-century feel—wide panes of glass, simple geometry, and bright natural light that blurs the line between inside and out.

    Steven Koleno BEYCOME OF FLORIDA LLC

    316 Country Club Dr, Oldsmar, FL 34677
  • /39

    $309,999

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    30 Aster Place, Oldsmar, FL 34677

    Welcome to the beautiful gated golf community of East Lake Woodlands. This gorgeous 2-bed, 2-bath villa has 1,250 sf of living space includes an open floor plan, split bedrooms (GREAT for that extra bit of privacy), living and dining rooms. Enjoy the serene outdoor patio, perfect for enjoying your morning coffee. The windows and new front sliders were installed a year ago. Both bathrooms have

    Karen Daley SMITH & ASSOCIATES REAL ESTATE

    30 Aster Place, Oldsmar, FL 34677
  • /49

    $369,700

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft

    206 Bedford St, Oldsmar, FL 34677

    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

    Tanja Cisliek FUTURE HOME REALTY INC

    206 Bedford St, Oldsmar, FL 34677
  • /26

    $330,000

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft

    1922 Hudson Ct, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Discover this beautifully updated and move-in ready 2-bedroom, 2-bath home with an oversized 1-car garage, ideally located in the heart of Oldsmar. From the moment you step inside, you’ll appreciate the open, airy layout designed for both comfort and functionality. The bright, cheerful kitchen is a true highlight, featuring light cabinetry, all

    Sabina Rozak HOMESMART

    1922 Hudson Ct, Oldsmar, FL 34677
  • /28

    $339,999

    • 3 Beds
    • 2 Baths
    • 1,255 Sq Ft

    163 Dolphin Dr E, Oldsmar, FL 34677

    Presenting a stunningly renovated beauty in Gull-Aire Village, a sought after 55+ golf cart and pet-friendly community on the north shores of Tampa Bay! If you're searching for your piece of Floridian paradise where no expense was spared for modernized living, then look no further! This wide open floor plan home will be sure to impress with EXQUISITE UPDATES and tons of fun bells and whistles.

    Micaela Morenz, PA BLAKE REAL ESTATE INC

    163 Dolphin Dr E, Oldsmar, FL 34677
  • /46

    $389,000

    • 4 Beds
    • 2 Baths
    • 1,288 Sq Ft

    324 Country Club Dr, Oldsmar, FL 34677

    Home Renovated to Perfection!**Welcome to your new home - a stunning, newly renovated home offering comfort and style. Located in a quiet and cozy area, this property is perfect for families looking for space and modernity.- **4 spacious rooms**: Ideal for the comfort of the whole family.- **2 completely renovated bathrooms**: With modern and elegant finishes.- **Large kitchen**:

    Aime Alfonso FRIENDS REALTY LLC

    324 Country Club Dr, Oldsmar, FL 34677
  • /48

    $369,900

    • 2 Beds
    • 2.5 Baths
    • 1,360 Sq Ft

    1712 Azalea Ct Unit A, Oldsmar, FL 34677

    Welcome to 1712 Azalea Court A in the heart of Oldsmar — a hidden gem just minutes from world-class beaches, top-rated golf courses, and some of the best attractions Tampa Bay has! This beautifully maintained home offers the perfect blend of comfort and convenience, nestled on a quiet cul-de-sac with no rear neighbors. Whether you’re looking for a full-time residence, vacation home, or

    Bert Calebro CALEBRO & ASSOCIATES

    1712 Azalea Ct Unit A, Oldsmar, FL 34677
  • /58

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    210 Eric Ct, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Welcome to East Lake Woodlands, one of Pinellas County’s most desirable gated communities, known for its natural beauty, abundant wildlife, and premier amenities. Tucked away on a peaceful cul-de-sac, this 3-bedroom, 2-bath patio home offers tranquil pond views, thoughtful updates, and easy access to everything the Tampa Bay area has to offer. Enjoy

    Nina Becker MAVREALTY

    210 Eric Ct, Oldsmar, FL 34677
  • /48

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,265 Sq Ft

    1912 Castle Bay Ct, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Price Improvement!!! Immaculately remodeled 3 bed 2 bath home located on a cul de sac street for added privacy in the heart of Oldsmar, FL. Step foot into this modern home greeted by beautiful vaulted ceiliings leading into the new quartz kitchen featuring a peninsula design with wood shaker cabinets, quartz countertops, tile backsplash and

    Abimael Ochoa EVRON & MCCARTHY REALTY LLC

    1912 Castle Bay Ct, Oldsmar, FL 34677
  • /20

    $389,500

    • 2 Beds
    • 2 Baths
    • 1,358 Sq Ft

    1802 Chinaberry Dr, Oldsmar, FL 34677

    - Total Renovation - Block/Slab Home - New Roof - New AC - New Water Heater - New Kitchen - Solid Wood Cabinets - Solid Surface Counters - New Bathrooms - New Floors - Interior and Exterior Paint - Landscaping - Large Fenced Yard -

    Dan Nease FOXX AND ASSOCIATES

    1802 Chinaberry Dr, Oldsmar, FL 34677

Home Trends in Oldsmar, FL

Housing Trends

Median Sale Price
$375,000
Median Single Family Sale Price
$522,500
Median Townhouse Sale Price
$397,000
Median 2 Bedroom Sale Price
$200,000
Median 1 Bedroom Sale Price
$148,500
Average Price Per Sq Ft
$254
Number of Homes for Sale
133
Last 12 months Home Sales
394
Months of Supply
4.10
Median List Price
$400,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-4%
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