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Oldsmar Townhomes for Sale

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  • /21

    $269,900

    • 2 Beds
    • 2.5 Baths
    • 1,110 Sq Ft

    273 Countryside Key Blvd, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Welcome to this MOVE IN READY 2-bedroom, 2.5-bathroom townhome in the desirable gated community of Countryside Key. Offering 1,110 sq ft of thoughtfully designed living space—plus an additional 75 sq ft ib the enclosed patio—this two-story home combines comfort, functionality, and convenience. Inside, you’ll find tile flooring throughout the first

    Agent Photo

    Mandy Cassiano

    KELLER WILLIAMS SOUTH SHORE

    (656) 226-3572

    273 Countryside Key Blvd, Oldsmar, FL 34677
  • /47

    $529,900

    • 3 Beds
    • 3 Baths
    • 1,834 Sq Ft

    112 Brent Cir, Oldsmar, FL 34677

    Now Offered at $529,900 – Waterfront Townhome with Deeded Boat Slip in Oldsmar! This beautifully updated, move-in ready townhouse offers relaxed coastal living in the charming golf cart community of Oldsmar – celebrated for its quality of life, top-rated schools, and unbeatable location between Tampa International Airport and sparkling Gulf beaches. Tucked inside a gated waterfront enclave with

    Agent Photo

    James Wheeler

    CHARLES RUTENBERG REALTY INC

    (656) 219-4022

    112 Brent Cir, Oldsmar, FL 34677
  • /22

    $375,000

    • 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

    106 Cutlass Way, Oldsmar, FL 34677
  • /24

    $499,000

    • 3 Beds
    • 3 Baths
    • 1,834 Sq Ft

    115 Brent Cir, Oldsmar, FL 34677

    Motivated Seller (Retired Real Estate professional) who would consider SELLER FINANCING for this 3 bedroom, 3-bathroom waterfront gem in the esteemed gated community of Seaside Estates. Enjoy breathtaking views of Old Tampa Bay and deeded boat dock access, all without the burden of high flood insurance (current premium under $1K/year, fully transferable). Step into this spacious 1,834 sq ft haven

    Camilo Perez HOME SOLD REALTY LLC

    115 Brent Cir, Oldsmar, FL 34677
  • /25

    $370,000

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

    602 Cabernet Way, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Motivated Sellers,Pay No HOA Fees Till Jan 1, 2026 with acceptable contract! High and Dry! No damage or flooding from Previous Storms. Come see this beautiful well maintained home with gorgeous tile throughout the main floor. The well laid out kitchen is a cooks delight, boasting 42 inch cabinets all with a rich espresso finish, granite

    Richard Forgione COLDWELL BANKER REALTY

    602 Cabernet Way, Oldsmar, FL 34677
  • /73

    $360,000

    • 3 Beds
    • 3 Baths
    • 1,834 Sq Ft

    102 Brent Cir, Oldsmar, FL 34677

    Huge Price Reduction immediate equity! Ready to move into. Seller Says Sell! Seller is Relocating. Best price for the money in Oldsmar Fl.Living space never effected by any storms and Flood Insurance only $1463. per year. Ready to move into. To sweeten the deal, the seller is offering concessions to buyers! This includes options to:Buy Down Your Interest Rate: Lower your monthly

    Mark Longenecker FUTURE HOME REALTY INC

    102 Brent Cir, Oldsmar, FL 34677
  • /41

    $500,000

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

    1608 Sunset Wind Loop, Oldsmar, FL 34677

    **This home has over $90,000 in upgrades and has experienced NO flooding or water issues ever!** Don’t miss this incredible opportunity—Situated on Old Tampa Bay, this waterfront and sought out gated community provides the best location for travel to Tampa, St Pete or our Gulf Beaches! Curb appeal draws you in, and once you step inside, you discover an open and inviting layout with high ceilings,

    Nicole DiSabato Harmon RE/MAX REALTEC GROUP INC

    1608 Sunset Wind Loop, Oldsmar, FL 34677
  • /75

    $465,000

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

    2313 Sunset Wind Loop, Oldsmar, FL 34677

    Welcome to this exquisite 3-bedroom, 2.5-bath deluxe townhome located in the exclusive gated waterfront community of Bayside Terrace. Enjoy resort-style living with a wealth of upscale amenities, including a clubhouse, a luxurious salt-water infinity pool overlooking Tampa Bay, a gas fire pit, a well-equipped gym, a fishing pier, and a kayak launch, all at your fingertips.This meticulously

    Quyen Trujillo FUTURE HOME REALTY INC

    2313 Sunset Wind Loop, 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

    Michael Beum RED SASH REALTY LLC

    421 Countryside Key Blvd, Oldsmar, FL 34677
  • /36

    $525,000

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

    2101 Sunset Wind Loop, Oldsmar, FL 34677

    Welcome to 2101 Sunset Wind Loop – A Beautifully Maintained Townhome in the Heart of Oldsmar!Located in the highly desirable community of Hayes Park Village, this charming 4-bedroom, 3-bathroom townhome combines comfort, convenience, and modern style. Built in 2019, this light and bright end-unit features an open-concept layout, perfect for both everyday living and

    Jay Chavez EXP REALTY LLC

    2101 Sunset Wind Loop, 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 TEAM REALTY

    1718 Azalea Ct Unit B, Oldsmar, FL 34677
  • /52

    $249,000

    • 3 Beds
    • 2.5 Baths
    • 1,339 Sq Ft

    75 Emerald Bay Dr, Oldsmar, FL 34677

    One or more photo(s) was virtually staged. Welcome to this bright and spacious 3 bedroom, 2.5 bath corner-unit townhome, with a prime location in the heart of Oldsmar. You’ll enjoy this beautiful and well-maintained community with a pool, surrounded by a ton of great amenities, and close to downtown Tampa and area beaches.Inside, the open-concept floorplan offers a light and airy feel

    Tabitha Clark EXP REALTY LLC

    75 Emerald Bay Dr, Oldsmar, FL 34677
  • /48

    $565,000

    • 3 Beds
    • 3 Baths
    • 1,834 Sq Ft

    163 Brent Cir, Oldsmar, FL 34677

    ** Deeded Boat Slip with Lift **Nestled in a serene, small gated community, this exquisite waterfront townhouse offers the perfect blend of luxury and tranquility. Located in the heart of Oldsmar, this home is a boater's paradise, complete with a deeded boat slip with a newer lift, for direct access to the pristine waters of Old Tampa Bay. Take the bike trail to Safety Harbor - or follow along

    Shana Story COMPASS FLORIDA LLC

    163 Brent Cir, Oldsmar, FL 34677
  • /30

    $265,000 Open Thu 4PM - 7PM

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

    367 Countryside Key Blvd, Oldsmar, FL 34677

    Move-in ready townhome in Oldsmar. Motivated seller offering $5000 credit. Step into style and peace of mind in this well maintained and updated townhome tucked inside the gated, pet-friendly community of Countryside Key. Safe and sound from any storm damage, it features a beautiful open concept first floor and large bedrooms on the second floor with vaulted ceilings. The 2024 kitchen features

    Stephanie Quarles BHHS FLORIDA PROPERTIES GROUP

    367 Countryside Key Blvd, Oldsmar, FL 34677
  • /39

    $274,900

    • 2 Beds
    • 2.5 Baths
    • 1,110 Sq Ft

    267 Countryside Key Blvd, Oldsmar, FL 34677

    Welcome to this Beautifully Updated 2-bedroom, 2.5-bathroom townhouse in the sought-after Countryside Key community of Oldsmar! This home offers a thoughtfully updated interior, including updated flooring, kitchen, and bathrooms, new AC in 2024, and a new water heater in 2023. You are going to love the large open-concept living area, the beautiful chef's kitchen, and the bonus room with access

    Robert Van Stronder KEY LIME REAL ESTATE INC

    267 Countryside Key Blvd, Oldsmar, FL 34677
  • /20

    $287,000

    • 2 Beds
    • 2.5 Baths
    • 1,110 Sq Ft

    396 Countryside Key Blvd, Oldsmar, FL 34677

    Welcome to this beautifully updated 2-bedroom, 2.5-bathroom townhouse with 1,110 square feet of living space, located in a secure, gated community offering both privacy and convenience. Completely renovated in 2018, this home features elegant upgrades throughout, including marble countertops in the bathrooms, shaker-style cabinetry, granite kitchen countertops, stylish tile flooring across the

    Jennifer Kenna EXP REALTY LLC

    396 Countryside Key Blvd, Oldsmar, FL 34677
  • /14

    $245,000

    • 2 Beds
    • 2.5 Baths
    • 1,110 Sq Ft

    244 Countryside Key Blvd, Oldsmar, FL 34677

    Cozy 2-Bedroom, 2.5-Bath Townhome in the heart of Oldsmar. The monthly HOA fees cover a wide range of services, including water, sewer, trash, cable, wifi, community pool, lawn and landscaping, roof maintenance and replacement, exterior pest control, and exterior building maintenance. Enjoy the convenience of being just minutes from the shopping, dining, a movie theater, parks, bike trail and

    Lin Huang CHARLES RUTENBERG REALTY INC

    244 Countryside Key Blvd, Oldsmar, FL 34677
  • /18

    $260,000 Open Mon 8AM - 7PM

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

    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
  • /14

    $225,000

    • 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
  • /68

    $569,000

    • 3 Beds
    • 3 Baths
    • 1,834 Sq Ft

    129 Brent Cir, Oldsmar, FL 34677

    MOTIVATED SELLER - WATERVIEWS from All 3 Floors, This UPDATED 3Bed 3Bath townhome is situated in the exclusive gated community of SEASIDE ESTATES in picturesque and historic Oldsmar. Nestled within a Townhome Complex of 67 units, this particular unit stands out as truly unique. The magnificent sunsets are breathtaking. The kitchen has STONE COUNTERTOPS, STAINLESS STEEL APPLIANCES, and offers ease

    Ena Ebanks FUTURE HOME REALTY INC

    129 Brent Cir, Oldsmar, FL 34677

Why Live in Oldsmar

Oldsmar is a well-established neighborhood centrally located between Clearwater and Tampa, known for its tight-knit community and slower pace of life. The area features a variety of independently owned small shops and restaurants, contributing to its hometown vibe. Spanning 10 square miles, Oldsmar includes 3 square miles of parks and trails, such as Harbor Palms Nature Park and R.E. Olds Park, which offer activities like kayaking, fishing, and playgrounds. The Oldsmar Sports Complex provides facilities for softball, soccer, and outdoor hockey, while the BMX track attracts competitive riders. Mobbly Bayou Preserve offers hiking, fishing, and zip-lining opportunities. Homes in Oldsmar range from ranch-style designs to Mediterranean-influenced architecture in planned subdivisions, with well-maintained lawns and a mix of bungalow and Craftsman influences. The neighborhood hosts annual events like Oldsmar Days and Nights and Celebrate Oldsmar, featuring live music, food vendors, and fireworks. Local dining options include Tampa Bay Brewing Company and Shaker & Peel, while grocery needs are met by Sunshine Food Mart, Publix, Walmart, and ALDI. Pinellas County Schools serve the area, with highly rated institutions such as Forest Lakes Elementary, Joseph L. Carwise Middle School, and East Lake High School. State Road 580 provides easy access to Tampa, 16 miles away, and Clearwater, just under 12 miles away. Mease Countryside Hospital is nearby, and Tampa International Airport is 11 miles from Oldsmar. The neighborhood is also home to Tampa Bay Downs, a thoroughbred horse racetrack that draws visitors for horse races, poker tournaments, and golf events.

Home Trends in Oldsmar, FL

Housing Trends

Median Sale Price
$385,000
Median Single Family Sale Price
$425,000
Median Townhouse Sale Price
$376,000
Median 2 Bedroom Sale Price
$156,000
Average Price Per Sq Ft
$264
Number of Homes for Sale
99
Last 12 months Home Sales
203
Months of Supply
5.90
Median List Price
$418,900
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-2%
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