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Oldsmar, FL Homes for Sale under $400,000

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  • /52

    $397,399

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

    370 S Woodlands Dr, Oldsmar, FL 34677

    Virtually Staged some photos. Price Reduction!! 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 Community of East Lake Woodlands. This meticulously maintained

    Agent Photo

    Michele Davis

    27NORTH REALTY

    (813) 536-4186

    370 S Woodlands Dr, Oldsmar, FL 34677
  • /36

    $385,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,773 Sq Ft

    908 Vineyard Ln, Oldsmar, FL 34677

    $14,000 PRICE REDUCTION! Welcome to elevated living in the heart of Oldsmar! This beautifully maintained 3-bedroom, 2.5-bath townhome by Taylor Morrison blends modern style, thoughtful upgrades, and a peaceful natural setting — all within a gated community. Step inside to a bright, open layout perfect for everyday living and entertaining. The stunning kitchen is a true centerpiece, featuring

    Agent Photo

    Keegan Siegfried

    LPT REALTY, LLC

    (656) 209-5070

    908 Vineyard Ln, Oldsmar, FL 34677
  • /32

    $319,000

    • 3 Beds
    • 2 Baths
    • 1,372 Sq Ft

    108 Dolphin Dr E, Oldsmar, FL 34677

    The Prettiest Home in Gull Aire – Turn-Key Perfection!Welcome to the crown jewel of Gull Aire, widely considered the most beautiful home in the entire community. This meticulously renovated 3-bedroom, 2-bathroom residence has been reimagined inside and out to offer the perfect blend of modern luxury and cozy community charm. If you are a social-seeking senior looking for a vibrant lifestyle

    Agent Photo

    Jackie Little

    KELLER WILLIAMS REALTY- PALM H

    (656) 220-0950

    108 Dolphin Dr E, Oldsmar, FL 34677
  • /18

    $304,000

    • 2 Beds
    • 2 Baths
    • 1,086 Sq Ft

    209 Hemingway Dr, Oldsmar, FL 34677

    Stunning Sun Ketch Townhome | Bright, Airy & Move-In Ready! Welcome to your slice of paradise in the highly sought-after Sun Ketch community of Oldsmar! This meticulously maintained 2-bedroom, 2-bathroom townhome offers the perfect blend of style, comfort, and convenience.Step inside to find gorgeous, rich cherry floors that flow through the living spaces, adding warmth and a touch of luxury

    Melissa Hinchliffe SMITH & ASSOCIATES REAL ESTATE

    209 Hemingway Dr, Oldsmar, FL 34677
  • /25

    $325,000

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft

    1803 Elmwood Dr, Oldsmar, FL 34677

    Welcome to this beautifully updated 2-bedroom, 2-bath home in Oldsmar, offering a bright, open layout designed for comfortable Florida living. The home features new luxury vinyl plank flooring throughout, an open floor plan, and large windows that fill the space with natural light. The living room-dining room combo flows seamlessly, with the dining area conveniently located near the kitchen. The

    Jeffrey Borham EXP REALTY LLC

    1803 Elmwood Dr, Oldsmar, FL 34677
  • /31

    $389,000

    • 3 Beds
    • 2.5 Baths
    • 1,452 Sq Ft

    271 Hemingway Dr, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Welcome to this inviting 3-bedroom, 2.5-bath townhome with a private garage, perfectly set on a premier conservation lot, in the quaint Oldsmar community of Sun Ketch Townhomes of Cypress Lakes. Step inside to find brand-new luxury vinyl plank flooring and a bright, open layout. The spacious great room features sliding glass doors leading to a

    Marcy Daniels COLDWELL BANKER REALTY

    271 Hemingway Dr, Oldsmar, FL 34677
  • /15

    $355,000

    • 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

    $315,000

    • 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
  • /36

    $390,000

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

    1505 Sunset Wind Loop, Oldsmar, FL 34677

    This beautiful townhouse (NEVER FLOODED) is located in the highly desirable waterfront gated community of Bayside Terrace. The home offers three bedrooms and two and a half bathrooms with a modern, open layout designed for comfortable living and entertaining. The 9 foot ceilings enhance the spacious feel and allow natural light to flow throughout the home. There is no immediate rear neighbor,

    Eric Jenkins, PA KELLER WILLIAMS REALTY- PALM H

    1505 Sunset Wind Loop, Oldsmar, FL 34677
  • /49

    $330,000

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

    40 Gretchen Ct, Oldsmar, FL 34677

    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 the largest units in the complex. You will

    Debra Gross BHHS FLORIDA PROPERTIES GROUP

    40 Gretchen Ct, Oldsmar, FL 34677
  • /52

    $382,000

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

    1909 Castle Bay Ct, Oldsmar, FL 34677

    --GORGEOUS HOME--Discover this IMMACULATE 3-bedroom, 2-bath BLOCK 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

    Craig Berenger, Jr KELLER WILLIAMS REALTY- PALM H

    1909 Castle Bay Ct, Oldsmar, FL 34677
  • /28

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft

    1704 Hibiscus Cir N, Oldsmar, FL 34677

    BACK ON THE MARKET!!! Seller offering $5,000 credit to buyer - make it yours!!!! Welcome to this inviting Florida home designed for comfortable living and effortless outdoor enjoyment. The highlight of the property is the private, screened-in pool and expansive patio, surrounded by mature tropical landscaping that creates a peaceful setting ideal for relaxing or entertaining year-round. Inside,

    Chris Ziebell REALTY ONE GROUP BEYOND

    1704 Hibiscus Cir N, 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
  • /39

    $380,000

    • 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

    $329,900

    • 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
  • /55

    $369,000

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

    1008 Mango Ct, Oldsmar, FL 34677

    LUXURY and COMFORT in the exclusive GATED WATERFRONT COMMUNITY of BAYSIDE TERRACE. This 3 bedroom 2 1/2 bath townhome offers an ideal open concept living. Step inside to the welcoming floorplan with high ceilings seamlessly connecting the kitchen, dining and living rooms featuring elegant luxury laminate throughout, NO CARPET. The stairway risers have been upgraded with textured mosaic tile in

    Whitney Cook KELLER WILLIAMS REALTY- PALM H

    1008 Mango Ct, Oldsmar, FL 34677
  • /46

    $350,000 Open Sun 12PM - 2PM

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

    904 Vineyard Ln, Oldsmar, FL 34677

    Luxury Living in Gated Tuscany Woods Preserve | Private Preserve Views | Designer Finishes.Welcome to this impeccably maintained 3-bedroom, 2.5-bath townhome with a 1-car garage in the highly sought-after, gated Tuscany Woods Preserve community. Offering a rare combination of privacy, upscale finishes, and a prime central location, this newer-built residence truly stands out.Step inside

    Piotr Gawienczuk RE/MAX ACTION FIRST OF FLORIDA

    904 Vineyard Ln, Oldsmar, FL 34677
  • /25

    $365,000

    • 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

    $355,000

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

    311 Vista Cruiser Ln, Oldsmar, FL 34677

    WOW WOW WOW This charming 3-bedroom, 2.5-bath home 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 parks and walking trails. A brick-paved walkway and covered front porch create a warm welcome, leading into an inviting open-concept

    Vanessa Leonard KELLER WILLIAMS REALTY- PALM H

    311 Vista Cruiser Ln, Oldsmar, FL 34677
  • /50

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    3087 Duane Ave, Oldsmar, FL 34677

    Back on the market due to buyer’s financing. THIS HOME NEVER FLOODED! Welcome to this move-in-ready home located in one of West Oldsmar’s most desirable neighborhoods, offering comfort, functionality, and thoughtful design. Situated on nearly one-third of an acre, this property provides generous outdoor space, privacy, and flexibility. The home features solar panels that significantly reduce

    Yhotzmine Fields BHHS FLORIDA PROPERTIES GROUP

    3087 Duane Ave, Oldsmar, FL 34677
  • /31

    $379,900

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

    1820 Driftwood Cir N, Oldsmar, FL 34677

    GREAT BUY ON THIS WONDERFUL 3 BEDROOM POOL HOME 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 INSTALLED IN 2012.

    Frank Acerra SELECT PROPERTIES INC

    1820 Driftwood Cir N, Oldsmar, FL 34677
  • /28

    $335,000

    • 2 Beds
    • 2 Baths
    • 1,206 Sq Ft

    1705 Ironwood Ct E, Oldsmar, FL 34677

    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

    Aned Pantoja KELLER WILLIAMS TAMPA PROP.

    1705 Ironwood Ct E, 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
  • /30

    $349,000

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

    316 Country Club Dr, Oldsmar, FL 34677

    Discover the quintessential Oldsmar, FL lifestyle in this stunning, move-in ready Mid-Century Modern 3-bedroom, 2-bath home. Seamlessly blending architectural significance with modern, low-maintenance living, this property offers incredible value and a prime location just steps from Tampa Bay. True to its roots, the residence is defined by clean lines, exposed beams, expansive windows, and

    Faith Walston SELLSTATE COASTAL REALTY

    316 Country Club Dr, Oldsmar, FL 34677
  • /56

    $350,000

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

    709 Lemonwood Dr, Oldsmar, FL 34677

    Welcome to this well-maintained 3-bedroom, 2-bath home offering 1,667 square feet of comfortable living space on a spacious 60x100 lot, located on a quiet street in desirable Oldsmar. This home features newer appliances, a 2025 hot water heater, and a 2022 AC system, providing peace of mind for years to come. Inside, you’ll find new carpet in Bedrooms 2 and 3, along with a bright and functional

    Jay Hundt PA PEOPLE'S CHOICE REALTY SVC LLC

    709 Lemonwood Dr, Oldsmar, FL 34677
  • /28

    $319,999

    • 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 VITA LUXURY 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
  • /33

    $380,000

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1811 Driftwood Cir S Unit 2, Oldsmar, FL 34677

    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

    Julio Vasquez OUT FAST REALTY & INVESTMENTS

    1811 Driftwood Cir S Unit 2, Oldsmar, FL 34677
  • /22

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,760 Sq Ft

    201 Dunkirk Rd, Oldsmar, FL 34677

    Welcome to this beautifully updated Oldsmar property. 3 bedrooms and 2 bathrooms to accommodate the entire family or have your private office space. The kitchen is the center of this house, with plenty counter space and cabinets. Beautiful glass door cabinets buffet area for entertaining your guess while you prepare your meals. The master bedroom is a true retreat, with a soaking tub, separate

    Richard Lamp PEOPLE'S CHOICE REALTY SVC LLC

    201 Dunkirk Rd, Oldsmar, FL 34677
  • /69

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 1,264 Sq Ft

    638 Jetstar Ln, Oldsmar, FL 34677

    Tired of surprise Saturday honey-do lists? Welcome to 638 Jetstar Ln—your low-maintenance launchpad to easy living in the heart of Hayes Park Village, Oldsmar’s friendliest front-porch community. This bright and breezy two-story townhome offers the ideal blend of style and simplicity. Inside, enjoy an OPEN-CONCEPT layout with LUXURY VINTYL PLANK flooring (that hides crumbs like a pro), GRANITE

    Amanda Lebiszczak CHARLES RUTENBERG REALTY INC

    638 Jetstar Ln, Oldsmar, FL 34677
  • /20

    $345,000

    • 3 Beds
    • 7 Baths
    • 1,392 Sq Ft

    103 Cutlass Way, Oldsmar, FL 34677

    Welcome to this impeccably maintained 3 bedroom, 2.5 bath residence in the highly sought-after Hayes Park Village in Oldsmar. Offering approximately 1,392 square feet of thoughtfully designed living space, this home showcases a beautifully renovated kitchen with contemporary finishes, ceramic flooring on the first floor, and carpet flooring on the second floor. The split-bedroom floor plan and

    Leyla Mohebbi FLORIDA COMMERCIAL GROUP

    103 Cutlass Way, Oldsmar, FL 34677
  • /20

    $369,000

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

    1802 Chinaberry Dr, Oldsmar, FL 34677

    Easily 3 Bedroom (EVEN 4) - Total Renovation - Block/Slab Home - Large Indoor Laundry - 2 Car Garage - New Roof - New AC - New Water Heater - New Kitchen - Solid Wood Cabinets - Solid Surface Counters - New Bathrooms - New Floors - Interior and Exterior Paint - Landscaping - Large Fenced Yard -

    Dan Nease FOXX AND ASSOCIATES

    1802 Chinaberry Dr, Oldsmar, FL 34677

Home Trends in Oldsmar, FL

Housing Trends

Median Sale Price
$374,000
Median Single Family Sale Price
$520,000
Median Townhouse Sale Price
$385,000
Median 2 Bedroom Sale Price
$189,000
Median 1 Bedroom Sale Price
$167,000
Average Price Per Sq Ft
$248
Number of Homes for Sale
146
Last 12 months Home Sales
401
Months of Supply
4.40
Median List Price
$399,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
-5%
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