Oldsmar, FL Homes

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  /70

  $550,000

  • 4 Beds
  • 3 Baths
  • 2,856 Sq Ft

  1717 Mapleleaf Blvd, Oldsmar, FL 34677

  Welcome to this Eastlake Oaks 4-bedroom, 3-full bath home with a dedicated office, 3-car garage, and screened-in lanai. Newer A/C 2023.The covered front porch features graceful arches and recessed lighting, creating a sheltered and welcoming entry.Double doors open to a two-story tiled foyer with clear sight lines into the living and dining areas, giving a bright first impression and a

  

  Jodi Avery

  KELLER WILLIAMS SOUTH TAMPA

  (656) 228-9273

  1717 Mapleleaf Blvd, Oldsmar, FL 34677
• Explore Oldsmar

• 

  

  

  /21

  $1,800 per month

  • 2 Beds
  • 1.5 Baths
  • 1,080 Sq Ft
  • Townhouse for Rent

  140 Douglas Rd W Unit D, Oldsmar, FL 34677

  Welcome to this beautifully maintained 2-bedroom, 1.5-bath townhouse, located in the heart of Oldsmar. Step inside to a spacious open-concept living and dining area, perfect for both relaxing and entertaining. The remodeled kitchen is a chef’s delight, featuring new, sleek cabinetry, attractive countertops, and all appliances included, making meal prep a breeze. The first floor boasts stylish

  

  Nicole DiSabato Harmon

  RE/MAX REALTEC GROUP INC

  (656) 223-1695

  140 Douglas Rd W Unit D, Oldsmar, FL 34677
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  /2

  $189,000 Sold Jan 12, 2026

  219 Caryl Way Unit 219, Oldsmar, FL 34677

  • 2 Beds
  • 2 Baths
  • 1,094 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $173/SF
  • 13 Days On Market

  Last Listing Agent John Blaeser BHHS FLORIDA PROPERTIES GROUP

  219 Caryl Way Unit 219, Oldsmar, FL 34677
• 

  

  /2

  Est $248,463 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,330 Sq Ft

  1718 Azalea Ct Unit C, Oldsmar, FL 34677

  1718 Azalea Ct Unit C, Oldsmar, FL 34677
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  /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

  

  Michele Davis

  27NORTH REALTY

  (813) 536-4186

  370 S Woodlands Dr, 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
• 

  /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
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,394 Sq Ft

  479 Trout Ln, Oldsmar, FL 34677

  479 Trout Ln, Oldsmar, FL 34677
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  /47

  $689,900

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

  602 Dartmouth Ave E, Oldsmar, FL 34677

  MOTIVATED SELLER. Immediate occupancy available! Exceptional opportunity in the heart of Oldsmar. This spacious 5-bedroom, 3.5-bathroom contemporary home offers nearly 3,000 sq ft of bright, open living with 10-ft ceilings throughout and a dramatic 21-ft entry foyer. Completely updated open concept kitchen features new white shaker soft close cabinets, quartz counters, gray tile backsplash,

  

  James Wheeler

  CHARLES RUTENBERG REALTY INC

  (656) 216-2592

  602 Dartmouth Ave E, Oldsmar, FL 34677
• 

  

  /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
• 

  /2

  $565,000 Sold Jan 12, 2026

  2315 Sunset Wind Loop, Oldsmar, FL 34677

  • 4 Beds
  • 3 Baths
  • 2,587 Sq Ft
  • Built 2019

  Last Sold Summary

  • 9% Below List Price
  • $218/SF
  • 45 Days On Market

  Last Listing Agent John Blaeser BHHS FLORIDA PROPERTIES GROUP

  2315 Sunset Wind Loop, Oldsmar, FL 34677
• 

  /2

  Est $231,773 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  214 Woodlake Wynde Unit 14, Oldsmar, FL 34677

  214 Woodlake Wynde Unit 14, Oldsmar, FL 34677
• 

  

  /45

  $445,000

  • 3 Beds
  • 2.5 Baths
  • 2,230 Sq Ft

  2313 Sunset Wind Loop, Oldsmar, FL 34677

  Experience coastal luxury and step into a lifestyle of refinement in this stunning 3-bedroom, 2.5-bath, 2 car garage townhome, nestled within the impressive gated waterfront enclave of Bayside Terrace! Curb appeal draws you into an open-concept layout designed for seamless entertaining with 10’ ceilings and beautiful tile flooring. The gourmet kitchen is a showstopper, featuring tons of cabinets,

  

  Nicole DiSabato Harmon

  RE/MAX REALTEC GROUP INC

  (656) 218-7331

  2313 Sunset Wind Loop, Oldsmar, FL 34677
• 

  

  /30

  $1,695 per month

  • 2 Beds
  • 2 Baths
  • 1,094 Sq Ft
  • Condo for Rent

  106 Mary Dr Unit 106, Oldsmar, FL 34677

  Welcome to East Lake Woodlands, a very desirable master-planned Golf and Country club community in centrally located Oldsmar. Close to schools and medical facilities as well as shopping, restaurants, movie theaters and more. Come home to your quiet gated community with park-like settings, walking and biking trails, beautiful lakes and a heated pool! This condo has a newly remodeled kitchen,

  

  Diane Chisholm

  SMITH & ASSOCIATES REAL ESTATE

  (656) 226-5857

  106 Mary Dr Unit 106, Oldsmar, FL 34677
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  /2

  $175,000 Sold Dec 30, 2025

  110 Cypress Ct Unit 3-82, Oldsmar, FL 34677

  • 2 Beds
  • 2 Baths
  • 1,054 Sq Ft
  • Built 1980

  Last Sold Summary

  • $166/SF
  • 5 Days On Market

  Last Listing Agent Julia Horton COLDWELL BANKER REALTY

  110 Cypress Ct Unit 3-82, Oldsmar, FL 34677
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  /2

  Not Listed For Sale

  Home Sites 1-5 Saint Petersburg Dr W, Oldsmar, FL 34677

  Home Sites 1-5 Saint Petersburg Dr W, Oldsmar, FL 34677
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  /36

  $229,900

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  145 Blue Marlin Dr, Oldsmar, FL 34677

  INCREDIBLE VALUE FOR THIS SPACIOUS HOME. The Time is NOW to own your place in the Florida sun. This contemporary residence offers the perfect blend of luxury and comfort, whether you're looking for a permanent home or a winter getaway. Enjoy modern conveniences like the island kitchen, vaulted ceilings, a front-loader full-size washer and dryer, electric window blinds, and a newer roof and A/C

  

  Jamie Everett

  FUTURE HOME REALTY INC

  (813) 733-6871

  145 Blue Marlin Dr, Oldsmar, FL 34677
• 

  

  /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

  $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
• 

  /2

  Est $504,966 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,040 Sq Ft

  1719 Mapleleaf Blvd, Oldsmar, FL 34677

  1719 Mapleleaf Blvd, Oldsmar, FL 34677
• 

  

  /22

  $365,000

  • 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
• 

  

  /29

  $2,800 per month

  • 3 Beds
  • 2 Baths
  • 1,264 Sq Ft
  • Property for Rent

  1711 Ironwood Ct E, Oldsmar, FL 34677

  Fully updated and move-in ready 3-bedroom, 2-bath home. Discover comfort, convenience, and modern living in this beautiful home. In the highly desirable Harbor Palms community. This home offers modern finishes throughout, including ceramic porcelain flooring, updated bathrooms, quartz countertops, new contemporary fixtures, freshly painted interior and exterior, a fully updated kitchen with

  Angela Paredes NEW BEGINNING REALTY LLC

  1711 Ironwood Ct E, Oldsmar, FL 34677
• 

  /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
• 

  /2

  Est $206,451 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft

  302 Woodlake Wynde Unit 3, Oldsmar, FL 34677

  302 Woodlake Wynde Unit 3, Oldsmar, FL 34677
• 

  

  /34

  $1,475,000

  • 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
• 

  

  /49

  $2,750 per month

  • 3 Beds
  • 2 Baths
  • 1,455 Sq Ft
  • House for Rent

  554 Lake Cypress Cir, Oldsmar, FL 34677

  Warm & Welcoming 3BR/2BA Family Home in Oldsmar – Great Schools & Big YardThis lovely single-family home is located in a quiet, safe, and family-friendly Oldsmar neighborhood, near Forest Lake Blvd and Pine Ave. The area is well known for excellent schools, nearby parks, and easy access to shopping, groceries, and daily necessities.The home offers 3 comfortable bedrooms and 2 full

  554 Lake Cypress Cir, Oldsmar, FL 34677
• 

  /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 $1,522,914

  Last Listing Agent Bill Gramatica CHARLES RUTENBERG REALTY INC

  314 Shore Dr E, Oldsmar, FL 34677
• 

  /2

  Est $367,202 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
• 

  

  /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
• 

  

  /26

  $2,200 per month

  • 2 Beds
  • 2 Baths
  • 1,502 Sq Ft
  • Townhouse for Rent

  40 Austin Place Unit 58, Oldsmar, FL 34677

  Check out this beautiful townhome located in the desirable East Lake Woodlands community. This second-floor residence features a spacious primary bedroom with direct access to a large screened back porch. The primary bathroom offers a relaxing soaking tub, separate shower, and a double-sink vanity. The home also includes a second bedroom and full bathroom with a tub and shower combination. One of

  Jeff Hall LISA HALL REALTY, INC

  40 Austin Place Unit 58, Oldsmar, FL 34677
• 

  /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 $393,455

  Last Listing Agent Kimberly Sobecki RE/MAX REALTEC GROUP INC

  30 Woodridge Cir, Oldsmar, FL 34677
• 

  

  /55

  Est $834,438 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
• 

  

  /59

  $249,999

  • 2 Beds
  • 2.5 Baths
  • 1,285 Sq Ft

  1718 Azalea Ct Unit B, Oldsmar, FL 34677

  One or more photo(s) has been virtually staged. NO HOA! MARVELOUS WATER VIEW FROM YOUR BALCONY! Beautiful 2BR 2.5BA two-story townhouse in Oldsmar, FL. Master bedroom has French doors that open to a wonderful water view right in your backyard....enjoy the view of two lakes and a creek with stunning wildlife! Best of all, you get to rest assured that your property is high and dry, NO WATER

  

  Daniel Hut

  HUT REALTY, LLC

  (656) 235-3010

  1718 Azalea Ct Unit B, Oldsmar, FL 34677
• 

  

  /5

  $850 per month

  • 1 Bed
  • 1 Bath
  • House for Rent

  2007 Mandalay Ct, Oldsmar, FL 34677

  Property Id: 2221909Private room for rent with private patio. This room is fully furnished with utilities and internet included.

  2007 Mandalay Ct, Oldsmar, FL 34677
• 

  /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 $801,352

  Last Listing Agent Miguel Velazquez FLORIDA LUXURY REALTY INC

  1855 Eau Claire Ct, Oldsmar, FL 34677
• 

  /2

  Est $332,462 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
• 

  

  /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

  

  John Blaeser

  BHHS FLORIDA PROPERTIES GROUP

  (813) 565-9394

  505 Federal St, Oldsmar, FL 34677
• 

  

  /5

  $1,850 per month

  • 2 Beds
  • 2.5 Baths
  • 1,224 Sq Ft
  • Townhouse for Rent

  128 Douglas Rd W Unit C, Oldsmar, FL 34677

  City Of Oldsmar Townhome.....This is a 2 Bedroom 2.5 Bathroom 1224 sq ft unit with Private Fenced yard and ready to occupy this month!! This spacious unit just had its kitchen and bathrooms updated with new cabinetry been painted and New Carpet installed This Week! This Oldsmar location is is Centrally located between downtown Tampa and Gulf Beaches and Only minutes from all local shops and

  Roy Kulp CHARLES RUTENBERG REALTY INC

  128 Douglas Rd W Unit C, Oldsmar, FL 34677
• 

  /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 $232,624

  Last Listing Agent Danelle Castillo TAMPA BAY REALTY & INVESTMENT GROUP

  204 Cypress Ln, 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

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