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Oldsmar, FL Homes for Sale under $400,000

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  • /22

    $350,000 Open Sat 10AM - 12PM

    • 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

    $399,899

    • 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
  • /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
  • /25

    $350,000

    • 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

    $399,000

    • 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
  • /29

    $320,000

    • 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
  • /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
  • /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

    $324,900

    • 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
  • /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
  • /25

    $379,900

    • 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
  • /48

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,364 Sq Ft

    138 Blue Marlin Dr, Oldsmar, FL 34677

    Opportunities like this rarely come along. Set on a true double lot, this 2016 Skyline home offers an exceptional combination of space, privacy, and quality upgrades that are nearly impossible to replicate. With 3 bedrooms, 2 bathrooms, a one-car garage, and a massive carport with workshop, this property delivers flexibility and functionality rarely found in the community. Inside, vaulted

    Mark Fazzini RE/MAX REALTEC GROUP INC

    138 Blue Marlin Dr, Oldsmar, FL 34677
  • /50

    $365,000

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

    311 Vista Cruiser Ln, Oldsmar, FL 34677

    This stunning 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 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

    $310,000

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

    20 Sylvia Place, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. PRICE REDUCED $10,000! MOVE-IN READY FLORIDA VILLA | 3 BEDROOMS + OFFICEJust $440/month HOA covers EVERYTHING: Roof, Lawn, Cable, Internet, Pest Control & More! This is the lock-and-leave Florida lifestyle you've been searching for—and it just became $10,000 more attainable. Discover this well maintained 3-bedroom, 2-bath villa PLUS dedicated

    Kera Arnone CHARLES RUTENBERG REALTY INC

    20 Sylvia Place, Oldsmar, FL 34677
  • /50

    $350,000

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

    3087 Duane Ave, Oldsmar, FL 34677

    HIGH AND DRY! THIS HOME NEVER FLOODED! Welcome to this charming, move-in-ready home offering comfort, style, and peace of mind in one of West Oldsmar’s most desirable neighborhoods. Situated on nearly one-third of an acre, this property combines privacy, efficiency, and thoughtful design — perfect for those seeking both space and convenience. Enjoy ultra-low electric bills with solar panels that

    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
  • /78

    $369,000

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

    648 Timber Bay Cir E, Oldsmar, FL 34677

    READY TO MAKE YOUR MOVE?-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

    Brenda Ayala GENSTONE REALTY

    648 Timber Bay Cir E, Oldsmar, FL 34677
  • /40

    $355,100

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

    316 Country Club Dr, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Welcome home to this beautifully preserved and thoughtfully updated mid-century modern 3-bedroom, 2-bath residence in Oldsmar, Florida, where timeless architecture meets an effortless outdoor lifestyle. Clean lines, exposed beams, and expansive windows define the design, filling the home with natural light and creating a seamless connection between

    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
  • /51

    $364,700

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

    206 Bedford St, Oldsmar, FL 34677

    One or more photo(s) has been 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

    Tanja Cisliek FUTURE HOME REALTY INC

    206 Bedford St, Oldsmar, FL 34677
  • /68

    $395,000

    • 3 Beds
    • 2 Baths
    • 2,034 Sq Ft

    1821 Driftwood Cir N, Oldsmar, FL 34677

    Welcome to this beautifully updated three-bedroom, two-bath home offering comfort, style, and an inviting outdoor retreat. Impact windows throughout provide peace of mind and energy efficiency, while luxury vinyl plank flooring adds durability and a modern touch. HVAC NEW 2022. The remodeled kitchen (2021) is a true standout, featuring a quartz island, farmhouse sink, high-efficiency vent,

    Lauren Levine DALTON WADE INC

    1821 Driftwood Cir N, Oldsmar, FL 34677
  • /36

    $388,000

    • 2 Beds
    • 2 Baths
    • 1,053 Sq Ft

    35 Pinewinds Blvd, Oldsmar, FL 34677

    VERY DESIRABLE GATED COMMUNITY OF EAST LAKE WOODLANDS, CORNER VILLA has VIEWS OF POND. Villa was BEAUTIFULLY REMODELED with NEWER WOOD CABINETS, and GRANITE COUNTER TOPS & NEWER APPLIANCES. LUXURY VINYL LAMINATE FLOORS throughout VILLA. Master Bedroom has A WALK-IN CLOSET with remodeled Master Suite BATHROOM. For Privacy there is a Split Bedroom Plan. Garage Conversion has a Flex Room for added

    Marie Becklund FUTURE HOME REALTY INC

    35 Pinewinds Blvd, Oldsmar, FL 34677
  • /37

    $319,000

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

    405 Woods Landing Trail, Oldsmar, FL 34677

    New Year - New Home! Welcome to the coveted East Lake Woodlands Gated Community. One of the first things you will notice when you walk in the door is the views to the back, featuring woods, water, wildlife and serenity. This beautiful 2 bedroom 2.5 bath townhouse features a carport, outside storage shed and large enclosed Florida room that opens with sliding doors from living room. There is also

    Loren Roye THE KEYES COMPANY - SARASOTA

    405 Woods Landing Trail, 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
  • /49

    $393,000

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

    1102 Vineyard Ln, Oldsmar, FL 34677

    Location, Location, Location! Welcome to this well-maintained, newer-construction end-unit townhouse located in the quiet, gated community of Tuscany Woods, built in 2018. Backing directly to the scenic Brooker Creek Preserve, this home offers privacy and tranquil views rarely found. This light and bright home features 3 bedrooms, 2.5 bathrooms, and a 1-car garage. The open-concept main level

    Debra Banks Waz FUTURE HOME REALTY

    1102 Vineyard Ln, 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
  • /48

    $319,990

    • 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

    $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
  • /46

    $325,000 Open Sat 1PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,988 Sq Ft

    160 Clubview Dr Unit 1, Safety Harbor, FL 34695

    KEY WEST MEETS SAFETY HARBOR in this special - one of a kind, upscale, custom nautical retreat with full handicap access features that include a vertical chair lift. Handicap equipment can be removed prior to closing desired. This spacious (1988 SF) open concept home comes fully furnished and completely TURN-KEY. Two bedrooms, two baths, island kitchen, great room, bonus Florida room, screened

    Jamie Everett FUTURE HOME REALTY INC

    160 Clubview Dr Unit 1, Safety Harbor, FL 34695

Home Trends in Oldsmar, FL

Housing Trends

Median Sale Price
$367,500
Median Single Family Sale Price
$519,900
Median Townhouse Sale Price
$499,000
Median 2 Bedroom Sale Price
$192,500
Median 1 Bedroom Sale Price
$148,500
Average Price Per Sq Ft
$250
Number of Homes for Sale
127
Last 12 months Home Sales
403
Months of Supply
3.80
Median List Price
$399,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-8%
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