Oldsmar, FL Homes

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  /43

  $395,000

  • 4 Beds
  • 2 Baths
  • 2,420 Sq Ft

  416 Woodward Ave, Oldsmar, FL 34677

  Welcome to 416 Woodward ave., sitting on a half-acre double lot on the corner of Shore drive and Woodward ave. This 2,420 sq. ft. property includes four bedrooms and two bathrooms. The backyard is designed for entertaining with a large pool and spa, stone pavers, and a grotto-style setting surrounded by mature landscaping. The location is quiet and peaceful with no through traffic, while still

  

  John Blaeser

  BHHS FLORIDA PROPERTIES GROUP

  (656) 236-2567

  416 Woodward Ave, Oldsmar, FL 34677
• Explore Oldsmar

• 

  

  

  /25

  $2,300 per month

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft
  • Townhouse for Rent

  245 Hemingway Dr, Oldsmar, FL 34677

  Option to pay security deposit in 3 installments! Nicely updated two-story townhome with a one-car garage, available for rent starting October 1st! All bedrooms are carpeted and upstairs. The primary suite has its own bathroom. Both guest rooms share the full hall bathroom which offers a tub and single sink. Downstairs, the kitchen adjoins the family room which features sliders to the screened

  

  June Connell

  COMPASS FLORIDA LLC

  (656) 235-3464

  245 Hemingway Dr, Oldsmar, FL 34677
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  /2

  $178,200 Sold Oct 31, 2025

  • Land
  • 0.14 Acre
  • $1,272,857 per Acre

  • 21 Days On Market

  107 Arlington Ave E, Oldsmar, FL 34677

  PRIME LOCATION in downtown Oldsmar. Discover an exceptional opportunity to build in one of Oldsmar’s most desirable neighborhoods. This BUILDABLE LOT is ideally situated between a stunning Spanish Revival estate and a classic-style home, offering the perfect setting for your new construction. Originally part of one of Oldsmar’s earliest estates dating back to 1924, the property at one time

  Ginger Tatarzewski FUTURE HOME REALTY INC

  107 Arlington Ave E, Oldsmar, FL 34677
• 

  

  /2

  Est $352,183 Not Listed For Sale

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

  608 Cabernet Way, Oldsmar, FL 34677

  608 Cabernet Way, Oldsmar, FL 34677
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  /47

  $715,000

  • 5 Beds
  • 3.5 Baths
  • 2,930 Sq Ft

  602 Dartmouth Ave E, Oldsmar, FL 34677

  PRICE IMPROVEMENT! Welcome to this spacious 5 bedroom, 3.5 bathroom home offering nearly 3,000 square feet of living space in the heart of highly desirable Oldsmar. Built in 2007, this contemporary two-story residence combines modern updates with timeless design, all just minutes from waterfront parks, trails, playgrounds, sports courts, dog parks, a fishing pier, and a public boat ramp. The

  

  James Wheeler

  CHARLES RUTENBERG REALTY INC

  (656) 216-2592

  602 Dartmouth Ave E, Oldsmar, FL 34677
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  /25

  $1,215 - $1,725 per month

  Aventine at Forest Lakes Apartment Homes

  1 - 3 Beds

  100 Old Village Way, Oldsmar, FL 34677

  Welcome to Aventine at Forest Lakes! Inside your new pet-friendly one, two, or three-bedroom apartment for rent, youll find everything you need for comfortable and convenient apartment living in Oldsmar, Florida. Each apartment comes with a fully-equipped kitchen, screened-in patios/balconies, plenty of closet space, air conditioning, and washer/dryer hookups for your convenience and comfort. At

  100 Old Village Way, Oldsmar, FL 34677
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  /2

  $230,000 Sold Oct 31, 2025

  • 1,712 Sq Ft
  • $134/SF
  • 110 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1949

  800 Saint Petersburg Dr W, Oldsmar, FL 34677

  Discover the perfect blend of space, location, and potential with this hidden gem nestled in the heart of Oldsmar! Situated on over a quarter of an acre, this spacious 4-bedroom, 2-bath home features a large, fenced-in backyard—ideal for outdoor living, pets, or future expansion.Step inside to find a bright, open layout that offers room to breathe and endless possibilities. Whether you're

  Christopher Grasso BHHS FLORIDA PROPERTIES GROUP

  800 Saint Petersburg Dr W, Oldsmar, FL 34677
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  /55

  Est $891,201 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,021 Sq Ft

  500 Shore Dr E, Oldsmar, FL 34677

  500 Shore Dr E, Oldsmar, FL 34677
• 

  

  /34

  $1,575,000

  • 4 Beds
  • 3 Baths
  • 2,496 Sq Ft

  316 Shore Dr E, Oldsmar, FL 34677

  Wake up to million-dollar views, and unwind with spectacular sunsets - this is the waterfront lifestyle you've been waiting for. This updated 4-bedroom, 3-bath pool home sits directly on Tampa Bay on an oversized lot along iconic Shore Drive in Oldsmar. Enjoy panoramic water views across the Bay from a home that's high and dry - built on an elevated slab that has never flooded, eliminating the

  

  James Wheeler

  CHARLES RUTENBERG REALTY INC

  (656) 231-5358

  316 Shore Dr E, Oldsmar, FL 34677
• 

  

  /19

  $2,500 per month

  • 5 Beds
  • 2.5 Baths
  • 2,827 Sq Ft
  • House for Rent

  395 Wingate Cir, Oldsmar, FL 34677

  This home is an absolute must see. Nicely equipped with beautiful wood floors downstairs and carpeting upstairs. High ceilings and plenty of natural light. Beautiful counter tops, spacious laundry room, huge 3 car garage. This community of Bay Arbor also comes with a beautiful community pool and playground . Close to shopping , world class dining. Close to Tampa road for a straight shot to Tampa

  Harry Talkington OLYMPIA GOLD TEAM REALTY

  395 Wingate Cir, Oldsmar, FL 34677
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  /2

  $1,000,000 Sold Oct 30, 2025

  • 3,251 Sq Ft
  • $308/SF
  • 35 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1991

  1349 Forestedge Blvd, Oldsmar, FL 34677

  Welcome to the Pinnacle of Luxury living in the Exclusive gated Community of East Lake Woodlands. Set on a picturesque, oversized lot with Serene Pond and Golf course views, this stunning residence is in the sought-after "Aberdeen" neighborhood. This Home features 4 Bedrooms, 3.5 Baths, plus an Office all under 3,251 sqft of meticulously upgraded living space. The Living areas Exude Elegance with

  Mark Fazzini RE/MAX REALTEC GROUP INC

  1349 Forestedge Blvd, Oldsmar, FL 34677
• 

  

  /40

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,066 Sq Ft

  272 Pelican Dr N, Oldsmar, FL 34677

  272 Pelican Dr N, Oldsmar, FL 34677
• 

  

  /55

  $249,000

  • 2 Beds
  • 2.5 Baths
  • 1,105 Sq Ft

  421 Countryside Key Blvd, Oldsmar, FL 34677

  Bright, Welcoming, and Ready to Greet You with a SmileWelcome to 421 Countryside Key, an adorable 2-bedroom, 2.5-bathroom townhome in a gated community with reserved parking, abundant natural light, and a layout designed for easy Florida living.Step inside to a bright, open living and dining area flowing seamlessly into the kitchen, perfect for everyday living and entertaining. A

  

  Sunny Alexander

  RED SASH REALTY LLC

  (656) 220-3413

  421 Countryside Key Blvd, Oldsmar, FL 34677
• 

  

  /23

  $1,049 - $1,795 per month

  East Lake Club Apartments

  1 - 3 Beds

  150 East Lake Club Dr, Oldsmar, FL 34677

  East Lake Club Apartments is a place you can really call home. From the time you walk in for a tour until the day you move out we strive to make you feel comfortable and happy. Our gated community is located in the heart of Oldsmar, just minuets away from everything you need. Please feel free to give us a call, or stop by in person for more information on our property. We look forward to meeting

  150 East Lake Club Dr, Oldsmar, FL 34677
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  /2

  $214,850 Sold Oct 30, 2025

  • 1,296 Sq Ft
  • $166/SF
  • 217 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  2052 Sheffield Ct, Oldsmar, FL 34677

  One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available at closing. Welcome home to this stunning property with a natural color palette throughout. The primary bedroom features a walk-in closet, perfect for all your storage needs. The primary bathroom boasts double sinks and good under sink storage, providing plenty of space for your toiletries. With fresh

  Karen Albright OPENDOOR BROKERAGE LLC

  2052 Sheffield Ct, Oldsmar, FL 34677
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  /47

  Est $556,129 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,791 Sq Ft

  154 Brent Cir, Oldsmar, FL 34677

  154 Brent Cir, Oldsmar, FL 34677
• 

  

  /42

  $1,155,000

  • 4 Beds
  • 3.5 Baths
  • 3,420 Sq Ft

  380 Wellington Ave, Oldsmar, FL 34677

  PRICE REDUCTION! Now priced below value, this is your chance to own this incredible Key West style pool home on an oversized conservation lot in highly desirable Oldsmar. Located on a cul de sac with no through traffic on nearly an acre of land, with lush tropical landscaping backing up to forested conservation for added privacy. At the main entry is an inviting wraparound porch. Step inside the

  

  James Wheeler

  CHARLES RUTENBERG REALTY INC

  (813) 797-4705

  380 Wellington Ave, Oldsmar, FL 34677
• 

  

  /13

  $1,500 per month

  • 2 Beds
  • 2 Baths
  • 982 Sq Ft
  • Condo for Rent

  201 Pine Ct, Oldsmar, FL 34677

  2 Bed/2 Bath Ground Floor Unit in EastLake Woodlands Community, Oldsmar! Welcome to your new home on Pine Court in the sought-after EastLake Woodlands Community! One small pet ok. This fantastic ground-floor unit offers 2bedrooms, 2bathrooms and a prime location close to the Woodlands Square Shopping Center and the Oldsmar Sports Complex. With easy access to shops, dining, entertainment,

  Lisa Connors RENT SOLUTIONS

  201 Pine Ct, Oldsmar, FL 34677
• 

  /2

  $335,000 Sold Oct 28, 2025

  • 1,036 Sq Ft
  • $323/SF
  • 31 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  208 Lee St, Oldsmar, FL 34677

  Step inside this beautifully renovated Mid-Century cottage that looks straight out of a design magazine. With a new roof installed in 2025 and a full modern makeover, this home offers style, comfort and peace of mind. The open floor plan features vaulted ceilings, abundant natural light, and stunning uniform vinyl plank flooring throughout. The gorgeous kitchen is a showstopper with granite

  Maria Azuaje PREMIER SOTHEBYS INTL REALTY

  208 Lee St, Oldsmar, FL 34677
• 

  

  /58

  Est $366,248 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,445 Sq Ft

  320 Vista Cruiser Ln, Oldsmar, FL 34677

  320 Vista Cruiser Ln, Oldsmar, FL 34677
• 

  

  /75

  $250,000 Pending

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

  2000 Sheffield Ct, Oldsmar, FL 34677

  Beautifully UPDATED 1296 sq ft, 2-bedroom, 2-bath villa with VAULTED CEILINGS and Stunning 24" CERAMIC TILE THROUGHOUT with a Bright OPEN floor plan. The Kitchen features GRANITE Countertops, WOOD Cabinets, and STAINLESS STEEL APPLIANCES. BOTH BATHROOMS have been tastefully UPDATED, and a convenient INSIDE LAUNDRY closet includes a NEW Washer purchased in 2025 (conveys with the sale). Step

  

  Sheri Ragsdale

  RAGSDALE RESIDENTIAL REALTY

  (656) 232-3260

  2000 Sheffield Ct, Oldsmar, FL 34677
• 

  

  /17

  $2,299 per month

  • 2 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • House for Rent

  589 Trout Ln, Oldsmar, FL 34677

  Over 55 Community.....Well-maintained single-family home in an over 55 neighborhood with a gorgeous view over-looking water from the large screened lanai in the back. Brand new LVP flooring in the living area and bedrooms, fully repainted. Open floor plan with cathedral ceilings. Efficient kitchen including a long breakfast bar, plenty of cabinet and pantry space, separate table area as well as

  589 Trout Ln, Oldsmar, FL 34677
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  /2

  $375,000 Sold Oct 27, 2025

  • 1,638 Sq Ft
  • $229/SF
  • 72 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1974

  1811 Hibiscus Ct S, Oldsmar, FL 34677

  One or more photo(s) has been virtually staged. Welcome to 1811 Hibiscus Court South, a charming 4-bedroom, 2-bathroom single-family home located in the Harbor Palms community. Originally built in 1973, this home was fully remodeled in 2025, with all permits approved, final inspections passed, and records on file with the city and county for peace of mind. All work has brought the property up to

  Howard 'Bogan' Stitzel A BETTER LIFE REALTY

  1811 Hibiscus Ct S, Oldsmar, FL 34677
• 

  

  /26

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  86 Pelican Dr N, Oldsmar, FL 34677

  86 Pelican Dr N, Oldsmar, FL 34677
• 

  

  /49

  $259,000 Pending

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

  25 Woods Landing Trail Unit 1, Oldsmar, FL 34677

  Under contract-accepting backup offers. Welcome to this beautifully updated 2 bedroom, 2 and a half bath townhome in one of Pinellas County’s most sought-after suburbs, the gated community of East Lake Woodlands. This move-in ready home offers maintenance free living, in a non-flood zone, at an unbeatable price point. With two spacious bedrooms, each featuring en-suite bathrooms and walk-in

  

  Alexander Zynski

  COLDWELL BANKER REALTY

  (813) 322-6261

  25 Woods Landing Trail Unit 1, Oldsmar, FL 34677
• 

  

  /46

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft
  • House for Rent

  525 Lakeview Dr, Oldsmar, FL 34677

  Welcome to this spacious three-bedroom, two-bath home featuring a split floor plan and a two-car garage. The home offers generously sized bedrooms, including a primary suite with a walk-in closet. Enjoy the large living area, and enclosed Florida room—perfect for relaxing or entertaining—as well as an additional enclosed rear patio that overlooks an expansive backyard and private conservation

  Ryan Nowlin RE/MAX ACTION FIRST OF FLORIDA

  525 Lakeview Dr, Oldsmar, FL 34677
• 

  /2

  $725,000 Sold Oct 27, 2025

  • 2,630 Sq Ft
  • $276/SF
  • 222 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1977

  130 Water Oak Way, Oldsmar, FL 34677

  Price Reduced. Wide Golf course scenery & overlooking the ponds!!! This two-story pristine house is in a cozy dead-end road of Woodland Estates community in notorious Gated, country club East Lake Woodlands. Offering 2,630 Heated Sq-Ft living area with 4 bedrooms, 3 bathrooms, a wide 2 cars garage, a resort looking pool area with paved deck & 15x29 Sq-Ft swimming Pool. This tastefully remodeled

  Marie-Pierre Cederman CEDERMAN PROPERTIES

  130 Water Oak Way, Oldsmar, FL 34677
• 

  

  /30

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,269 Sq Ft

  452 Pompano Ct, Oldsmar, FL 34677

  452 Pompano Ct, Oldsmar, FL 34677
• 

  

  /46

  $599,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,938 Sq Ft

  1631 Shady Oaks Dr, Oldsmar, FL 34677

  Under contract-accepting backup offers. Welcome to your Florida dream home in Eastlake Oaks, one of Oldsmar’s most sought-after communities perfectly positioned between Tampa and Clearwater. This move-in ready 3 bedroom, 2 bathroom single family home offers nearly 2,000 sq ft of open-concept living with high ceilings, abundant natural light, and seamless indoor-outdoor flow. Inside, you’ll find

  

  James Wheeler

  CHARLES RUTENBERG REALTY INC

  (656) 218-7998

  1631 Shady Oaks Dr, Oldsmar, FL 34677
• 

  

  /7

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  3175 Phoenix Ave, Oldsmar, FL 34677

  This 800 sq ft apartment is in a stilt house. The kitchen is large with stove, fridge, dishwasher and disposal. Washer and dryer in the unit as well as central air and new hot water heater. Bathroom was recently renovated. Primary bedroom is large enough for a King bed. Smaller bedroom can accommodate a queen bed. This 2 bedroom 1 bath apartment located halfway between Tampa and the beaches.

  3175 Phoenix Ave, Oldsmar, FL 34677
• 

  /2

  $927,000 Sold Oct 24, 2025

  • 4,186 Sq Ft
  • $221/SF

  • 4 Beds
  • 4.5 Baths
  • Built 1986

  70 Deerpath Dr, Oldsmar, FL 34677

  LUXURY RESORT LIFESTYLE living at its finest!!! This Spectacular SPRAWLING Executive POOL Residence is nestled on a PERFECTLY manicured PREMIER lot (half an ACRE!!) in one of Eastlake Woodland’s most desirable subdivisions, Deerpath – home to 49 uniquely designed homes! This beautiful subdivision is double gated, zoned for Excellent "A" RATED Schools & located near one of the many entrances to

  Kimberly Janowiak FUTURE HOME REALTY INC

  70 Deerpath Dr, Oldsmar, FL 34677
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  /32

  Est $649,304 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,123 Sq Ft

  611 Clarendon St, Oldsmar, FL 34677

  611 Clarendon St, Oldsmar, FL 34677
• 

  

  /39

  $550,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  602 Devonshire St, Oldsmar, FL 34677

  Under contract-accepting backup offers. Welcome to 602 Devonshire St – Oldsmar Living at Its BestStep into this newly renovated home where comfort, security, and lifestyle come together seamlessly. From the moment you arrive, you’ll notice the meticulous updates, including impact-rated windows and doors that provide peace of mind, energy efficiency, and storm protection. Inside, the heart

  

  Jay Powell

  KELLER WILLIAMS TAMPA CENTRAL

  (656) 240-7031

  602 Devonshire St, Oldsmar, FL 34677
• 

  

  /22

  $1,695 per month

  • 2 Beds
  • 2 Baths
  • 1,054 Sq Ft
  • Condo for Rent

  261 Cypress Ln, Oldsmar, FL 34677

  Welcome to Eastlake Woodlands, a gated golf community located in the heart of Oldsmar, FL. This stunning 2-bedroom, 2-bathroom condo features shaker cabinets, a tile kitchen backsplash, granite counters, luxury vinyl plank flooring, and tile floors in wet areas. Enjoy the convenience of a laundry room with a washer and dryer included, as well as a screened patio with beautiful conservation and

  Karen Joyal ADVANTAGE REALTY SERVICES, INC

  261 Cypress Ln, Oldsmar, FL 34677
• 

  /2

  $577,000 Sold Oct 23, 2025

  • 2,143 Sq Ft
  • $269/SF
  • 84 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1997

  422 Cypress View Dr, Oldsmar, FL 34677

  This Oldsmar home offers a rare combination of privacy, thoughtful upgrades, and an unbeatable location. This 4-bedroom, 2.5-bath home sits on a premium conservation lot with no rear or side neighbors and features a beautiful water view of the large pond just beyond the backyard—creating a peaceful and private retreat surrounded by nature. Inside, the home has been beautifully updated with

  Candice Kelly IAD FLORIDA LLC

  422 Cypress View Dr, Oldsmar, FL 34677
• 

  

  /57

  Est $215,639 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,151 Sq Ft

  109 Lakeview Way Unit 5, Oldsmar, FL 34677

  109 Lakeview Way Unit 5, Oldsmar, FL 34677
• 

  

  /22

  $365,000 Open Sun 1PM - 3PM

  • 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

  

  Rachel Mayhew

  RE/MAX CHAMPIONS

  (656) 240-4710

  106 Cutlass Way, Oldsmar, FL 34677
• 

  

  /13

  $3,395 per month

  • 4 Beds
  • 2 Baths
  • 2,352 Sq Ft
  • House for Rent

  475 Forest Park Rd, Oldsmar, FL 34677

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3659.90. That covers your base rent, $3395.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  475 Forest Park Rd, Oldsmar, FL 34677
• 

  /2

  $385,000 Sold Oct 22, 2025

  • 1,186 Sq Ft
  • $325/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1983

  1252 Holly Cir, Oldsmar, FL 34677

  Beautifully updated 3-Bedroom, 2 bath home with a 1 car garage, in the desirable Forest Lakes Community in Oldsmar! This lovely home is situated on a peaceful cul-de-sac in an ideal location. As soon as you enter the home, you will feel welcomed by the charming entry, with the open floor plan, vaulted ceilings and elegant porcelain tile, which sets the stage for modern living. Great floor plan

  Janice Rodriguez LPT REALTY, LLC

  1252 Holly Cir, Oldsmar, FL 34677
• 

  

  /28

  Est $204,617 Not Listed For Sale

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

  207 Cypress Ct Unit 3-119, Oldsmar, FL 34677

  207 Cypress Ct Unit 3-119, Oldsmar, FL 34677

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