32

Oldsmar, FL Townhomes for Sale

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  • /49

    $275,000

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

    25 Woods Landing Trail Unit 1, Oldsmar, FL 34677

    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 closets, this townhome is designed with

    Agent Photo

    Alexander Zynski

    COLDWELL BANKER REALTY

    (813) 322-6261

    25 Woods Landing Trail Unit 1, Oldsmar, FL 34677
  • /19

    $269,900

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

    273 Countryside Key Blvd, Oldsmar, FL 34677

    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 floor and luxury vinyl plank upstairs—no carpet!

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    Mandy Cassiano

    KELLER WILLIAMS SOUTH SHORE

    (656) 226-3572

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

    $550,000

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

    112 Brent Cir, Oldsmar, FL 34677

    Newly Improved Price on this Move-In Ready Townhouse! This beautifully updated waterfront home with deeded boat slip is located in the safe and picturesque golf cart community of Oldsmar. 3 bedrooms, 3 full bathrooms, and private garage with storage and 3-car tandem parking, in a gated community with pool, spa, and tennis courts, surrounded by Tampa Bay and charming Oldsmar. The open concept main

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    James Wheeler

    CHARLES RUTENBERG REALTY INC

    (656) 219-4022

    112 Brent Cir, Oldsmar, FL 34677
  • /46

    $349,900

    • 3 Beds
    • 2.5 Baths
    • 1,450 Sq Ft

    330 Woods Landing Trail, Oldsmar, FL 34677

    Bring all offers the sellers are motivated to sell. Drive through this beautiful, gated community of Eastlake Woodlands to your home. You will enjoy living in this spacious 3 bedrooms, 2 1⁄2 baths and 1 carport end unit townhome with a private backyard and views of a pond. This townhome is updated with a LARGE eat in kitchen. You will find in the kitchen granite counters, white shaker style

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    Laura Trundle

    COASTAL PROPERTIES GROUP INTERNATIONAL

    (656) 213-3306

    330 Woods Landing Trail, Oldsmar, FL 34677
  • /45

    $394,000

    • 2 Beds
    • 2 Baths
    • 1,883 Sq Ft

    60 Woodridge Cir Unit 1, Oldsmar, FL 34677

    EXQUISITELY REMODELED two-story townhome in the heart of the coveted community of EAST LAKE WOODLANDS! STUNNING UPDATES throughout that exude comfort and style! Roof, cable, internet and exterior maintenance all covered by association! This end unit has a RENOVATED KITCHEN that overlooks the dining room and ENCLOSED SUNROOM, plus offers sliders to a PRIVATE LANAI! The inviting living room is

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    June Connell

    COMPASS FLORIDA LLC

    (813) 710-3298

    60 Woodridge Cir Unit 1, Oldsmar, FL 34677
  • /47

    $360,000

    • 3 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    1171 Clays Trail, Oldsmar, FL 34677

    ** Seller will cover HOA fees for the rest of this year ** Welcome to your dream home! This spacious 3-bedroom, 2.5-bathroom townhouse offers an exceptional blend of luxury and carefree living. The living and dining room offer breathtaking water views on the main level as does the Master bedroom upstairs. The master features a fully screened in balcony making this unit perfect for those who

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    Farzana Zalil

    CHARLES RUTENBERG REALTY ORLANDO

    (813) 519-3961

    1171 Clays Trail, Oldsmar, FL 34677
  • /60

    $395,000

    • 2 Beds
    • 2.5 Baths
    • 1,888 Sq Ft

    1710 Sunset Wind Loop, Oldsmar, FL 34677

    Discover comfort and luxury in this meticulously maintained townhome in the exclusive gated waterfront community of Bayside Terrace, offering an ideal blend of open concept living and private retreats. Boasting 2 generous primary bedrooms with full ensuite bathrooms, and a large versatile upstairs loft. Step inside and be greeted by an inviting open floor plan on the main level, seamlessly

    Whitney Cook KELLER WILLIAMS REALTY- PALM H

    1710 Sunset Wind Loop, Oldsmar, FL 34677
  • /25

    $380,000

    • 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
  • /47

    $359,000

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft

    170 Ingrid Place, Oldsmar, FL 34677

    PRICE ADJUSTMENT TO $359,000 - Drive through the gates of the East Lake Woodlands community, and you will appreciate the lush surroundings of the established neighborhood! As you enter this charming 3-bedroom, 2.5-bath townhouse you’re immediately welcomed by a bright, open-concept living space, freshly painted and ready for your personal touch. The spacious living area flows seamlessly into the

    Kisha Linebaugh COMPASS FLORIDA LLC

    170 Ingrid Place, Oldsmar, FL 34677
  • /27

    $379,000

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

    1010 Mango Ct, Oldsmar, FL 34677

    Welcome to Bayside Terrace, a prestigious gated waterfront community offering Key West-style living near the iconic Safety Harbor Bridge This serene neighborhood is designed for relaxation and coastal luxury, with amenities that create the ultimate retreat. Inside your home, this delightful 3 bedroom, 2.5 bath 1 car townhome offers modern elegance. Features include plantation shutters, sleek

    Rene Mailaender RE/MAX REALTEC GROUP INC

    1010 Mango Ct, Oldsmar, FL 34677
  • /57

    $363,900

    • 3 Beds
    • 2.5 Baths
    • 1,604 Sq Ft

    284 Hemingway Dr, Oldsmar, FL 34677

    This end-unit townhome offers a private, fenced backyard and picturesque pond views from the screened porch. The primary bedroom is conveniently located on the main floor and features a spacious walk-in closet, a double sink vanity, and a walk-in shower. Upstairs, two bedrooms are separated by a full bathroom.The kitchen boasts ample cabinet and counter space, complemented by newer quartz

    James Mcpeak MCPEAK REALTY GROUP INC

    284 Hemingway Dr, Oldsmar, FL 34677
  • /73

    $398,000

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

    102 Brent Cir, Oldsmar, FL 34677

    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 payments and make homeownership more

    Mark Longenecker FUTURE HOME REALTY INC

    102 Brent Cir, Oldsmar, FL 34677
  • /30

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 1,450 Sq Ft

    215 Woods Landing Trail, Oldsmar, FL 34677

    Step into luxury with this beautifully upgraded home featuring designer finishes throughout! The gourmet kitchen boasts sparkling quartz countertops and a brand-new built-in range, perfect for the chef at heart. Enjoy the comfort of newer appliances and a modern, energy-efficient A/C (only 5 years old).Upstairs, you'll find a convenient second-floor laundry with washer and dryer, while the custom

    David Pratt CENTURY 21 COASTAL ALLIANCE

    215 Woods Landing Trail, 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

    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 INTRUSION! The property features an in-demand open

    Daniel Hut HUT TEAM REALTY

    1718 Azalea Ct Unit B, Oldsmar, FL 34677
  • /49

    $269,900

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

    75 Emerald Bay Dr, Oldsmar, FL 34677

    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 throughout the first floor. The large living

    Tabitha Clark EXP REALTY LLC

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

    $575,000

    • 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. Step inside to discover a private retreat that you

    Shana Story COMPASS FLORIDA LLC

    163 Brent Cir, Oldsmar, FL 34677
  • /29

    $270,000

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

    367 Countryside Key Blvd, Oldsmar, FL 34677

    Motivated seller offering $5000 credit towards new Water Heater, buyer closing costs or pre-paids. Step into style and peace of mind at 367 Countryside Key Blvd 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

    Stephanie Quarles BHHS FLORIDA PROPERTIES GROUP

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

    $274,900 Open House 8/02

    • 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
  • /24

    $499,200

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

    115 Brent Cir, Oldsmar, FL 34677

    Motivated Seller (Retired Real Estate professional) offering 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 featuring an open-concept

    Camilo Perez HOME SOLD REALTY LLC

    115 Brent Cir, Oldsmar, FL 34677
  • /21

    $295,000

    • 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
  • /35

    $245,000

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

    309 Countryside Key Blvd Unit 2, Oldsmar, FL 34677

    Feel the safety and security of this gated townhome community conveniently located between Tampa and Clearwater. In this community the HOA handles all the big items like roof, exterior painting and landscaping and you just work on relaxing, socializing and tennis. Countryside Key townhomes is offering $2000 toward your closing costs or decorating preferences after closing. This fantastic location

    Cheryl Franzese COASTAL PROPERTIES GROUP INTERNATIONAL

    309 Countryside Key Blvd Unit 2, Oldsmar, FL 34677
  • /63

    $625,000

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

    140 Brent Cir, Oldsmar, FL 34677

    Wake up every day to sweeping, unobstructed views of Old Tampa Bay on every floor in this stunning waterfront townhome, perfectly positioned in a quiet, gated community in the heart of Oldsmar. Complete with a deeded boat slip and 10,000 lb lift, this home was designed for anyone who loves being on the water. Whether you’re heading out for a sunset cruise or enjoying coffee on the deck with the

    Mimi DeSetto COASTAL PROPERTIES GROUP INTERNATIONAL

    140 Brent Cir, Oldsmar, FL 34677
  • /35

    $250,000

    • 2 Beds
    • 2.5 Baths
    • 1,270 Sq Ft

    1700 Azalea Ct Unit B, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Welcome to your serene retreat in the heart of Oldsmar! This beautifully updated 2-bedroom, 2.5-bath townhome offers the perfect blend of comfort, style, and privacy. Nestled in a quiet, well-maintained community with NO HOA, this home boasts no rear neighbors, giving you peaceful views and added seclusion.Step inside to discover a brand-new

    Montana Byrd BLAKE REAL ESTATE INC

    1700 Azalea Ct Unit B, 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

    $266,000 Open Tue 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
  • /41

    $520,000

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

    1608 Sunset Wind Loop, Oldsmar, FL 34677

    ** This home has over $90,000 in upgrades** Experienced NO flooding or water issues during recent storms** 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

    Nicole DiSabato Harmon RE/MAX REALTEC GROUP INC

    1608 Sunset Wind Loop, Oldsmar, FL 34677
  • /36

    $275,000

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

    262 Countryside Key Blvd, Oldsmar, FL 34677

    Don’t Miss This Gorgeous, Fully Remodeled 2-Bedroom, 2.5-Bath Townhome!Step inside this beautifully updated townhouse and be amazed by the attention to detail. The kitchen features sleek shaker cabinets, stunning granite countertops, a tile backsplash, and stainless steel appliances. A convenient breakfast bar and closet pantry make this kitchen as functional as it is stylish. The open living

    Shannon Wilson SOUTHERN LIFE REALTY

    262 Countryside Key Blvd, 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, Florida, is a small town between downtown Tampa and Clearwater, offering waterfront living in the heart of Tampa Bay. With a population of around 13,600, Oldsmar maintains a homey atmosphere while providing convenient access to nearby cities. The town boasts an impressive parks system, dedicating about 40% of its land to parks and preserves, including the ten-mile Oldsmar Trail that winds through eight parks, offering scenic views of marsh ecosystems and coastal landscapes. Notable parks include R.E. Olds Park, Veterans Memorial Park, and Mobbly Bayou Beach Park. The Oldsmar Flea Market, touted as the largest in the south, operates from Wednesday to Sunday, while annual events like Oldsmar Days and Nights and Oktoberfest bring the community together with live music and classic car shows. Education in Oldsmar is served by Pinellas County Schools, recognized as the best school district in the Tampa area. Palm Harbor University High School, located eight miles northwest, is highly rated, particularly for its STEM programs. The town features a mix of housing styles, including ranch-style homes, craftsman builds, and luxurious waterfront condos. Real estate in Oldsmar typically sells quickly, with homes averaging 38 days on the market. Local attractions include Tampa Bay Downs, a thoroughbred horse racing track, and HorsePower, a nonprofit farm and animal sanctuary. Empower Adventures Tampa Bay offers ziplining and aerial obstacle courses, while the Tampa Bay Skating Academy provides figure skating and hockey lessons. Oldsmar is safer than the national average, with low violent crime rates, though the southern part of town faces flood risks.

Home Trends in Oldsmar, FL

Housing Trends

Median Sale Price
$383,000
Median Single Family Sale Price
$470,000
Median Townhouse Sale Price
$387,500
Median 2 Bedroom Sale Price
$214,900
Median 1 Bedroom Sale Price
$167,000
Average Price Per Sq Ft
$259
Number of Homes for Sale
80
Last 12 months Home Sales
149
Months of Supply
6.40
Median List Price
$399,999
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
2%
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