Oldsmar, FL Homes for Sale under $400,000

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  /29

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft

  416 Country Club Dr, Oldsmar, FL 34677

  Nestled in the highly deisrable City of Oldsmar, this home has been tastefuly renovated. You'll love the updated kitchen with new stainless steel appliances, stone counter top and lovely build in desk. This modern kitchen has beautiful black cabinets, double sink, new range, refrigerator, dishwasher, and microwave. There are new ceiling fans throughout the home and plenty of decorator lighting.

  Jenny Meers MURRAY BELL REAL ESTATE LLC

  416 Country Club Dr, Oldsmar, FL 34677
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  /51

  $259,900

  • 3 Beds
  • 2 Baths
  • 1,471 Sq Ft

  258 Pelican Dr N, Oldsmar, FL 34677

  Now available in the sought-after 55+ Gull-Aire Village: a meticulously maintained 1995 Jacobsen home, offering over 1,400 square feet of comfortable living space. This inviting residence features three spacious bedrooms and two full bathrooms, with a split floor plan that provides privacy for guests. The home boasts a newly installed TPO roof (2024) that covers the main unit, Florida room, and

  Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

  258 Pelican Dr N, Oldsmar, FL 34677
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  /44

  $349,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,190 Sq Ft

  442 Evergreen Dr, Oldsmar, FL 34677

  Welcome to 442 Evergreen Drive, nestled in one of Oldsmar's most desirable neighborhoods! This beautifully updated 3 bedroom, 2-bath residence offers the perfect blend of comfort, style, and Florida living. Filled with abundant natural light, the thoughtfully designed floor plan creates an inviting atmosphere ideal for both everyday living and effortless entertaining.Step outside to your

  Sheri Boesch EXP REALTY LLC

  442 Evergreen Dr, Oldsmar, FL 34677
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  /38

  $188,000

  $7K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 879 Sq Ft

  204 Windward Place Unit 36, Oldsmar, FL 34677

  Welcome to 204 Windward Place #36, a move-in-ready condominium located in the gated community of East Lake Woodlands, one of Oldsmar's most established residential communities. Offering low-maintenance living in the heart of Tampa Bay, this well-maintained residence combines comfort, convenience, and easy access to everything Florida's Gulf Coast has to offer. Designed with functionality and

  Robert Dinan BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  204 Windward Place Unit 36, Oldsmar, FL 34677
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  /44

  $160,000

  • 2 Beds
  • 2 Baths
  • 915 Sq Ft

  134 Sycamore Ln Unit H, Oldsmar, FL 34677

  This beautifully maintained 2 bedroom, 2 bath condo in fantastic Gardens of Forest lakes, offers perfect blend of comfort and convenience. As you step inside, you will be greeted by an open floor plan that seamlessly connects the living and kitchen areas. Kitchen features granite countertops, wood cabinets. The dining area opens to a charming balcony overlooking trees and it is perfect for

  Tatiana Russu FUTURE HOME REALTY INC

  134 Sycamore Ln Unit H, Oldsmar, FL 34677
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  /14

  $189,000

  $56K PRICE DROP

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

  62 Emerald Bay Dr, Oldsmar, FL 34677

  Heart of Oldsmar convenient to restaurants, shopping and Tampa. 2 Story, 2 Bedroom / 2.5 Bathroom Townhome in Oldsmar, AC 7/23, newer luxury vinyl flooring and newer paint.

  Lin Huang CHARLES RUTENBERG REALTY INC

  62 Emerald Bay Dr, Oldsmar, FL 34677
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  /7

  $299,000

  • 2 Beds
  • 1 Bath
  • 1,143 Sq Ft

  200 Fairfield St, Oldsmar, FL 34677

  Welcome home to this beautifully renovated 2-bedroom, 1-bath property in desirable Oldsmar, Florida! This move-in-ready home has been completely updated from top to bottom. The kitchen features updated cabinetry, countertops, and finishes, creating a stylish and functional space for everyday living. The bathroom has also been redone with fresh, modern touches. Throughout the home, you'll find

  Allison Daigle SUNSHINE REALTY COMPANY LLC

  200 Fairfield St, Oldsmar, FL 34677
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  /52

  $155,000

  $45K PRICE DROP Pre-Foreclosure

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft

  372 Cobia Way, Oldsmar, FL 34677

  Welcome to 372 Cobia Way — one of the best locations in Gull-Aire Village, sitting directly across from the community pool, spa, and clubhouse! This resident-owned, 55+ golf cart friendly community in the heart of Oldsmar offers the best of Florida retirement living at an unbeatable value.Step inside to a bright, open floor plan featuring dark hardwood-style flooring and bold coastal teal

  Justin Cans IMPACT REALTY TAMPA BAY

  372 Cobia Way, Oldsmar, FL 34677
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  /23

  $199,000

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

  392 Cobia Way, Oldsmar, FL 34677

  This move-in-ready, well-maintained home is one of the larger homes in this golf-cart-friendly 55+ community and is being sold FURNISHED. The open floor plan features a spacious living room/dining room combination with luxury vinyl plank flooring and attractive plantation shutters, creating a clean, bright and inviting space. The kitchen offers white cabinetry, an updated countertop and a new

  Joe Gibbons LIPPLY REAL ESTATE

  392 Cobia Way, Oldsmar, FL 34677
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  /46

  $395,000

  $10K PRICE DROP Pre-Foreclosure

  • 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
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  /26

  $180,000

  • 2 Beds
  • 2 Baths
  • 879 Sq Ft

  115 Windward Place Unit 15, Oldsmar, FL 34677

  LOCATION, LOCATION, LOCATION! Close to entertainment, shopping, restaurants, airports, and world-famous beaches, this beautiful ground floor, end unit condo is waiting for you! Located in the highly desirable, gated community Meadows of Eastlake Woodlands, this home has it all! Gorgeous granite countertops highlight the kitchen as does the impressive cabinet space and closet pantry. The inviting

  Millie Jackson FLORIDA PREMIERE REALTY

  115 Windward Place Unit 15, Oldsmar, FL 34677
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  /26

  $249,900

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

  2044 Sheffield Ct, Oldsmar, FL 34677

  MOVE-IN READY OLDSMAR VILLA WITH A PRIVATE FENCED YARD! Beautifully refreshed 2-bedroom, 2-bath, 1,296-square-foot end-unit villa! VERY LOW HOA DUES at $110/month. Step inside to a bright, open interior where soaring vaulted ceilings and abundant natural light give the home an impressively spacious feel. The open living and dining areas offer plenty of room for entertaining, while updated

  Dale Hunter GUARDIAN REAL ESTATE SERVICES

  2044 Sheffield Ct, Oldsmar, FL 34677
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  /21

  $259,900

  $10K PRICE DROP

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

  123 Dolphin Dr S, Oldsmar, FL 34677

  Beautiful remodeled home. Move in ready. Plantation shutters thoughout. All new porcelain tile, new appliances. Freshly painted inside and out. Tiled kitchen with open shelving with large corner windows that allow for the light to fill the room. Spacious living and dinning room with a open floor plan. Primary bedroom has adjoining ensuite with bay windows and walkin closet. Guest Bedroom is also

  Ruthann Underwood PAM RYAN REALTY INC

  123 Dolphin Dr S, Oldsmar, FL 34677
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  /25

  $239,000

  • 2 Beds
  • 2 Baths
  • 1,054 Sq Ft

  104 E Cypress Ct Unit 104, Oldsmar, FL 34677

  Located in East Lake Woodlands this quiet private second-story unit offers serene views overlooking the golf course and has a bright welcoming interior. Thoughtfully remodeled throughout, the home features abundant cabinet space, newer appliances, and major system upgrades including air conditioner and furnace. The unit has been tastefully finished with beautiful Florida-style decor, creating a

  Stephen Hachey FLAT FEE MLS REALTY

  104 E Cypress Ct Unit 104, Oldsmar, FL 34677
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  /29

  $175,000

  • 2 Beds
  • 2 Baths
  • 1,266 Sq Ft

  410 Dolphin Dr S, Oldsmar, FL 34677

  Welcome to Gull-Aire Village, one of Pinellas County's most desirable and active 55+ communities! Don't miss this opportunity to own a home in the highly sought-after Gull-Aire Village, where you own the land and enjoy an incredibly affordable HOA fee of just $70 per month. Whether you're looking for a full-time residence, seasonal retreat, or future investment property, this community offers

  David Mayhew CHARLES RUTENBERG REALTY INC

  410 Dolphin Dr S, Oldsmar, FL 34677
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  /34

  $247,000

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  407 Dolphin Dr S, Oldsmar, FL 34677

  Experience the charm of Gull-Aire Village 55+ in this beautifully renovated home, ready for its next owners. Boasting a spacious 1,320 square feet with stylish laminate flooring throughout, this residence is perfect for entertaining and comfortable living. The split-bedroom layout ensures privacy for both you and your guests, while both bathrooms feature luxurious walk-in showers for added

  Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

  407 Dolphin Dr S, Oldsmar, FL 34677
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  /57

  $189,999

  $9K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,096 Sq Ft

  130 Nancy Dr Unit 37, Oldsmar, FL 34677

  "RESORT STYLE LIVING" in East Lake Woodlands! This beautifully maintained 2-bedroom,2-bath condominium offers approximately 1,151 sq ft of comfortable living space in one of Oldsmar’s most desirable gated communities. Major updates provide peace of mind, including flooring, A/C system, hot water heater, dishwasher, washer and dryer, and bedroom carpeting all approximately 3 years old, plus a

  Steve DeMatos RE/MAX ALLIANCE GROUP

  130 Nancy Dr Unit 37, Oldsmar, FL 34677
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  /43

  $310,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft

  650 Timber Bay Cir W, Oldsmar, FL 34677

  CHARMING 3 bed, 1 bath impeccable home in downtown Oldsmar area. NEW interior doors, NEW stove, NEW baseboards, NEW bathroom vanity, lighting, mirror,, NEW remote control ceiling fans with lights, NEW carriage lights (front and back) NEW GFCI outlets, NEW paint interior, exterior, NEW paint garage, patio, NEWER windows and slider with integral blinds (2023, 2026), HWH 2025, DISHWASHER 2023,

  Ginger Tatarzewski FUTURE HOME REALTY INC

  650 Timber Bay Cir W, Oldsmar, FL 34677
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  /17

  $214,900

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 1,024 Sq Ft

  2034 Montego Ct, Oldsmar, FL 34677

  Welcome to this spacious 1,028 sq ft villa in the desirable Bayside Meadows community of Oldsmar. This beautifully updated home offers the comfort and privacy of villa living with a one-car garage, fenced backyard, and screened lanai—perfect for enjoying Florida’s year-round outdoor lifestyle.The thoughtfully designed interior features a kitchen overlooking the living area, a cozy

  Jerry Hills RE/MAX ELITE REALTY

  2034 Montego Ct, Oldsmar, FL 34677
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  /43

  $115,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 915 Sq Ft

  123 Loblolly Ct Unit B, Oldsmar, FL 34677

  Virtually Staged. GROUND FLOOR ~ NON - FLOOD ZONE. 2 Bedrooms, 2 Bathroom and move in ready in the heart of Oldsmar! Community amenities include a pool, playground, basketball court, tennis courts and beautiful lake with a dock! Bring your fishing pole.Freshly painted and move-in ready, tile floor throughout, making it an ideal canvas for a buyer looking to add personal touches and build

  Christina Paolillo CHARLES RUTENBERG REALTY INC

  123 Loblolly Ct Unit B, Oldsmar, FL 34677
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  /20

  $345,000

  • 3 Beds
  • 2.5 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
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  /48

  $198,500

  $51K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft

  347 Canal Way, Oldsmar, FL 34677

  Welcome to Gull-Aire Village, a 55+ PET-Friendly and Golf Cart Friendly community in the Heart of Oldsmar! Gull-Aire Village is a Land-Owned community, meaning YOU OWN THE LAND! not just the home. A Very unique property with No rear neighbors. This home comes FULLY FURNISHED! and Features A NEWER ROOF (only 3yrs Old) Newer WINDOWS and Doors, New Flooring(2025) and Vapor Barrier (2025) New Water

  Asher Walli CHARLES RUTENBERG REALTY INC

  347 Canal Way, Oldsmar, FL 34677
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  /24

  $259,900

  $70K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft

  704 Lemonwood Dr, Oldsmar, FL 34677

  Investor special with exceptional upside! This concrete block 2-bedroom, 2-bath, 2-car garage home is priced to sell and offers outstanding renovation potential. Situated on a nicely sized lot with beautiful lake views and no rear neighbors, the fully fenced backyard has plenty of room for a pool. The home has an updated electrical panel. The HVAC system was updated in 2019. The roof was last

  Johnny Mead DALTON WADE INC

  704 Lemonwood Dr, Oldsmar, FL 34677
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  /36

  $400,000

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

  2013 Sunset Wind Loop, Oldsmar, FL 34677

  Discover modern comfort and effortless living in this beautifully maintained 3-bedroom, 2.5-bath townhome, ideally located in the sought-after Bayside Terrace community of Oldsmar. Built in 2019, this move-in ready home blends contemporary finishes with thoughtful upgrades designed for today's lifestyle.The bright, open-concept floorplan is anchored by a spacious kitchen featuring

  Nicole Chin KELLER WILLIAMS TAMPA CENTRAL

  2013 Sunset Wind Loop, Oldsmar, FL 34677

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