Oldsmar, FL Homes

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  /22

  $365,000 Open Sat 2PM - 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
• Explore Oldsmar

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  /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

  $237,500 Sold Nov 14, 2025

  2000 Sheffield Ct, Oldsmar, FL 34677

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1986

  Last Sold Summary

  • 12% Below List Price
  • $183/SF
  • 56 Days On Market

  Last Listing Agent Sheri Ragsdale RAGSDALE RESIDENTIAL REALTY

  2000 Sheffield Ct, Oldsmar, FL 34677
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  /2

  Est $369,469 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
• 

  

  

  /55

  $249,000 Pending

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

  421 Countryside Key Blvd, Oldsmar, FL 34677

  Under contract-accepting backup offers. Bright, Welcoming, and Ready to Greet You with a Smile Welcome 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

  

  Sunny Alexander

  RED SASH REALTY LLC

  (656) 220-3413

  421 Countryside Key Blvd, Oldsmar, FL 34677
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  /28

  $1,800 per month

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

  207 Palmetto Ct, Oldsmar, FL 34677

  Updated 2-Bedroom, 2-Bath Ground Floor Condo with Patio in Gated East Lake Woodlands! This beautifully updated 2-bedroom, 2-bath condo is located in the desirable gated community of East Lake Woodlands. Featuring newer HVAC and a hot water heater (just 3 years old), this home offers modern comfort with luxury vinyl flooring throughout, including the screened lanai. The open-concept great room

  

  Nicole DiSabato Harmon

  RE/MAX REALTEC GROUP INC

  (656) 213-4539

  207 Palmetto Ct, Oldsmar, FL 34677
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  /2

  $550,000 Sold Oct 10, 2025

  1640 Gray Bark Dr, Oldsmar, FL 34677

  • 3 Beds
  • 2 Baths
  • 1,927 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $285/SF
  • 4 Days On Market

  Last Listing Agent Maria Hourdas KELLER WILLIAMS REALTY- PALM H

  1640 Gray Bark Dr, Oldsmar, FL 34677
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  /55

  Est $892,702 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
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  /34

  $1,500,000

  • 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
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  /24

  $2,395 per month

  • 4 Beds
  • 2 Baths
  • 1,401 Sq Ft
  • House for Rent

  1915 Saginaw Ct, Oldsmar, FL 34677

  Nice single family one story 4 bedroom 2 bath 2 car garage with garage door opener and transmitter on a quiet cul-de-sac! Home features: solid wood front door, front coat closet; dark engineered wood floors in living and bedrooms; tile in kitchen, dining and bath areas; beautiful 42 inch wood kitchen cabinets with refrigerator, built-in microwave, stove/oven, built-in dishwasher and large deep

  Colleen Tuttle

  RE/MAX REALTEC GROUP INC

  (656) 223-1784

  1915 Saginaw Ct, Oldsmar, FL 34677
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  /2

  $590,000 Sold Nov 04, 2025

  1631 Shady Oaks Dr, Oldsmar, FL 34677

  • 3 Beds
  • 2 Baths
  • 1,938 Sq Ft
  • Built 1998

  Last Sold Summary

  • 9% Below List Price
  • $304/SF
  • 102 Days On Market

  Last Listing Agent James Wheeler CHARLES RUTENBERG REALTY INC

  1631 Shady Oaks Dr, Oldsmar, FL 34677
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  /2

  Est $335,643 Not Listed For Sale

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

  206 Cabernet Way, Oldsmar, FL 34677

  206 Cabernet Way, Oldsmar, FL 34677
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  /49

  $200,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,094 Sq Ft

  219 Caryl Way Unit 219, Oldsmar, FL 34677

  Experience resort style living in this beautifully updated 2-bed, 2-bath, 1,094 sq ft condo in the gated East Lake Woodlands community. Fresh paint, new carpet, and serene second-floor views set the tone for a move-in-ready retreat. Inside, the home offers exceptional storage with pull-out kitchen drawers, a pantry, abundant cabinetry, a pull-out spice rack, multiple closets, and a spacious

  

  John Blaeser

  BHHS FLORIDA PROPERTIES GROUP

  (656) 202-3822

  219 Caryl Way Unit 219, 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

  $989,000 Sold Sep 18, 2025

  219 Washington Ave, Oldsmar, FL 34677

  • 5 Beds
  • 3 Baths
  • 2,850 Sq Ft
  • Built 2021

  Last Sold Summary

  • $347/SF
  • 21 Days On Market

  Current Estimated Value $966,926

  Last Listing Agent Darlene Davenport COMPASS FLORIDA LLC

  219 Washington Ave, Oldsmar, FL 34677
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  /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
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  /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
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  /65

  $2,000 per month

  • 2 Beds
  • 2 Baths
  • 1,465 Sq Ft
  • House for Rent

  101 Lindsay Ln, Oldsmar, FL 34677

  Location Location....This Two Bedroom/Two Bath open concept split plan 1st floor condo is located in the Golf and Tennis Country Club of East Lake Woodlands. The Master Bedroom has two closets including a large walk-in closet. The Lanai is enclosed and features a Laundry closet and storage closet. Vinyl flooring through out. This spacious unit in St. Andrews Condominium has it's own community

  Jeff Hall LISA HALL REALTY, INC

  101 Lindsay Ln, Oldsmar, FL 34677
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  /2

  $1,560,000 Sold Mar 05, 2025

  314 Shore Dr E, Oldsmar, FL 34677

  • 4 Beds
  • 3.5 Baths
  • 2,886 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • $541/SF
  • 11 Days On Market

  Current Estimated Value $1,537,751

  Last Listing Agent Bill Gramatica CHARLES RUTENBERG REALTY INC

  314 Shore Dr E, Oldsmar, FL 34677
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  /47

  Est $563,064 Not Listed For Sale

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

  154 Brent Cir, Oldsmar, FL 34677

  154 Brent Cir, Oldsmar, FL 34677
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  /61

  $600,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,587 Sq Ft

  2315 Sunset Wind Loop, Oldsmar, FL 34677

  Under contract-accepting backup offers. Welcome to 2315 Sunset Wind Loop, a stunning 4-bedroom, 3-bathroom end-unit townhome located in the highly desirable gated community of Bayside Terrace in Oldsmar. Built in 2019, this beautifully upgraded home combines modern finishes, open-concept living, and resort-style amenities along the shores of Upper Tampa Bay. The community offers 24/7 virtual

  

  John Blaeser

  BHHS FLORIDA PROPERTIES GROUP

  (656) 232-1021

  2315 Sunset Wind Loop, Oldsmar, FL 34677
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  /23

  $1,274 - $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

  $385,000 Sold May 30, 2025

  30 Woodridge Cir, Oldsmar, FL 34677

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1984

  Last Sold Summary

  • 13% Below List Price
  • $183/SF
  • 49 Days On Market

  Current Estimated Value $398,270

  Last Listing Agent Kimberly Sobecki RE/MAX REALTEC GROUP INC

  30 Woodridge Cir, Oldsmar, FL 34677
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  /58

  Est $381,753 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
• 

  

  /53

  $394,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,673 Sq Ft

  1801 Forest Dr Unit 3, Oldsmar, FL 34677

  Under contract-accepting backup offers. Welcome to 1801 Forest Drive – Your Florida Retreat in the Heart of OldsmarStep into comfort and style with this beautifully maintained 3-bedroom, 2-bathroom single-family home located in one of Oldsmar’s most established and peaceful neighborhoods. Nestled on a generous corner lot, surrounded by mature trees and lush landscaping, this home offers a

  

  Debra Briscoe

  FINE PROPERTIES

  (813) 295-7960

  1801 Forest Dr Unit 3, Oldsmar, FL 34677
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  /48

  $1,795 per month

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

  209 Cypress Ct Unit 121, Oldsmar, FL 34677

  Fantastic Beautifully Renovated first floor 2bed/2bath/ 1 CARPORT condo located in highly sought-after East Lake Woodlands Community!! This stunning condo has nicely updated modern kitchen, renovated bathrooms, luxury vinyl plank floors and tile floors in wet areas. Full size WASHER & DRYER are conveniently located in the utility closet off the Florida room/Lanai. This condominium offers comfort,

  Grace Omyla PROPERTY LEADERS RE INC

  209 Cypress Ct Unit 121, Oldsmar, FL 34677
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  /2

  $770,000 Sold Apr 25, 2025

  1855 Eau Claire Ct, Oldsmar, FL 34677

  • 4 Beds
  • 4 Baths
  • 2,673 Sq Ft
  • Built 1991

  Last Sold Summary

  • 9% Below List Price
  • $288/SF
  • 75 Days On Market

  Current Estimated Value $788,641

  Last Listing Agent Miguel Velazquez FLORIDA LUXURY REALTY INC

  1855 Eau Claire Ct, Oldsmar, FL 34677
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  /44

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft

  116 Dolphin Dr S, Oldsmar, FL 34677

  116 Dolphin Dr S, Oldsmar, FL 34677
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  /100

  $945,000

  • 5 Beds
  • 3.5 Baths
  • 3,140 Sq Ft

  1471 Briargrove Way, Oldsmar, FL 34677

  One or more photo(s) has been virtually staged. Live the Florida lifestyle in the gated Aberdeen enclave of East Lake Woodlands with this elegant Arthur Rutenberg-built executive home. Located in one of Oldsmar’s most desirable golf and country club communities, this timeless Belleair split floor plan offers 3,140 square feet of thoughtfully designed living space. The home features five bedrooms,

  

  Eric Timmons

  KELLER WILLIAMS REALTY- PALM H

  (656) 232-3080

  1471 Briargrove Way, Oldsmar, FL 34677
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  /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

  $766,900 Sold Jan 10, 2025

  4764 Stoneview Cir, Oldsmar, FL 34677

  • 4 Beds
  • 3 Baths
  • 2,606 Sq Ft
  • Built 1993

  Last Sold Summary

  • 13% Below List Price
  • $294/SF
  • 108 Days On Market

  Current Estimated Value $776,150

  Last Listing Agent Inessa Kosonen RE/MAX ACTION FIRST OF FLORIDA

  4764 Stoneview Cir, Oldsmar, FL 34677
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  /2

  Est $475,583 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,928 Sq Ft

  1107 Mango Ct, Oldsmar, FL 34677

  1107 Mango Ct, Oldsmar, FL 34677
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  /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

  

  Michele Davis

  27NORTH REALTY

  (813) 536-4186

  370 S Woodlands Dr, Oldsmar, FL 34677
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  /20

  $2,900 per month

  • 3 Beds
  • 2 Baths
  • 2,142 Sq Ft
  • House for Rent

  1811 Forest Dr, Oldsmar, FL 34677

  This beautiful pool home is located in a quiet neighborhood of Oldsmar. This home features laminate floors throughout the entire house with recently painted walls and trim. The kitchen is open and has marble countertops with stainless steel appliances, a large basin sink, painted wood cabinets, and natural stone ledger backsplash. Home rents with brand new furniture so you don't have to worry

  Brian Mathay IMPACT REALTY TAMPA BAY

  1811 Forest Dr, Oldsmar, FL 34677
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  /2

  $245,000 Sold Mar 25, 2025

  204 Cypress Ln, Oldsmar, FL 34677

  • 2 Beds
  • 2 Baths
  • 1,053 Sq Ft
  • Built 1980

  Last Sold Summary

  • 2% Below List Price
  • $233/SF
  • 82 Days On Market

  Current Estimated Value $236,506

  Last Listing Agent Danelle Castillo TAMPA BAY REALTY & INVESTMENT GROUP

  204 Cypress Ln, Oldsmar, FL 34677
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  /2

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft

  607 Canal Way, Oldsmar, FL 34677

  607 Canal Way, Oldsmar, FL 34677
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  /47

  $700,000 Open Sat 12PM - 2PM

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

  602 Dartmouth Ave E, Oldsmar, FL 34677

  Reduced price - exceptional value! 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, close to waterfront parks, playgrounds, trails, 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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  /16

  $3,275 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 $3539.90. That covers your base rent, $3275.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  475 Forest Park Rd, Oldsmar, FL 34677
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  /2

  $545,000 Sold Apr 17, 2025

  811 Christina Cir, Oldsmar, FL 34677

  • 3 Beds
  • 2 Baths
  • 1,621 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $336/SF
  • 6 Days On Market

  Current Estimated Value $536,674

  Last Listing Agent Kathy Lorenti COLDWELL BANKER REALTY

  811 Christina Cir, Oldsmar, FL 34677
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  /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

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