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Oldsmar, FL Homes for Sale under $300,000

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  • /39

    $220,000

    • 2 Beds
    • 2 Baths
    • 1,368 Sq Ft

    98 Sugar Bear Dr Unit 57, Safety Harbor, FL 34695

    No rear neighbors. Backs up to Briar Creek and trees. This lovely home is in a great quiet location and allows a cat or a dog up to 25 pounds. It has newer windows, new HVAC Jan 20/2025, replaced subfloors and installed luxury vinyl, replaced electrical panel Jan 2026, repaired vapor barrier & plumbing underneath & raised HVAC ducts that were hanging down. A 4 Point Inspection was done Jan 2026

    Agent Photo

    Renny Bryden

    CHARLES RUTENBERG REALTY INC

    (727) 910-5894

    98 Sugar Bear Dr Unit 57, Safety Harbor, FL 34695
  • /33

    $246,000

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

    388 Countryside Key Blvd, Oldsmar, FL 34677

    2025 HVAC! Assumable FHA Loan! Welcome to 388 Countryside Key, a charming 2-bedroom, 1.5-bathroom townhome located in the highly sought-after Oldsmar, FL community. This delightful two-story residence boasts an open-concept first floor with a spacious kitchen, ample cabinetry, a generous pantry, and a convenient laundry/utility closet with a full-size washer and dryer. The living and dining areas

    Agent Photo

    Kevin Baker

    TROPIC SHORES REALTY

    (656) 240-3431

    388 Countryside Key Blvd, Oldsmar, FL 34677
  • /44

    $255,000

    • 2 Beds
    • 2 Baths
    • 1,502 Sq Ft

    40 Shamrock Way Unit 64, Oldsmar, FL 34677

    Welcome home to 40 Shamrock Way in sunny Oldsmar FL. This move-in ready, updated 2-bedroom, 2-bath condo with a loft, offering 1,502 square feet of light-filled living space in the highly sought-after East Lake Woodlands community in Oldsmar. Featuring an open floor plan, voluminous ceilings, abundant windows, and a split bedroom layout, this home feels bright, spacious, and welcoming, perfect

    Agent Photo

    Jessica Christianson

    EXP REALTY LLC

    (656) 232-2495

    40 Shamrock Way Unit 64, Oldsmar, FL 34677
  • /16

    $243,900

    • Land
    • 1.13 Acres
    • $215,841 per Acre

    0 Strathmore Ave, Oldsmar, FL 34677

    Discover a rare opportunity to own a sought-after 1.13-acre vacant lot in the heart of Oldsmar! Tucked away in a quiet, established neighborhood, this oversized parcel offers the perfect canvas to build your dream home—with **no HOA restrictions** holding you back. Large lots like this are incredibly hard to find in Oldsmar, especially in such a prime location. What truly sets this property apart

    Agent Photo

    Steve Capen

    COLDWELL BANKER REALTY

    (656) 228-1955

    0 Strathmore Ave, 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

    Agent Photo

    Daniel Hut

    HUT REALTY, LLC

    (656) 235-3010

    1718 Azalea Ct Unit B, Oldsmar, FL 34677
  • /36

    $204,500

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    130 Woodlake Wynde Unit 36, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Must See!! Beautifully renovated 2-bedroom, 2-bath residence offering 924 square feet of thoughtfully designed living space. This liight and inviting condo showcases a custom solid wood kitchen, stainless steel and white appliances, vaulted ceilings with widows that invite an abundance of light, sleek luxury vinyl flooring, fresh interior paint.

    Rachel Mascara COLDWELL BANKER REALTY

    130 Woodlake Wynde Unit 36, Oldsmar, FL 34677
  • /32

    $254,900

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

    240 Cypress Ln Unit 240, Oldsmar, FL 34677

    Welcome to 240 Cypress Lane in Oldsmar, where effortless Florida living meets refined, turnkey luxury with tranquil water views and a premier golf lifestyle just moments away. This fully furnished, completely renovated second-floor residence offers the perfect blend of comfort, style, and security, high and dry with no flood insurance required. Step inside to a bright, open-concept layout

    Nick Wimperis LPT REALTY, LLC

    240 Cypress Ln Unit 240, Oldsmar, FL 34677
  • /40

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,385 Sq Ft

    40 Sylvia Place, Oldsmar, FL 34677

    Welcome to this exceptional 3-bedroom villa located in the fabulous East Lake Woodlands community. This villa is move-in ready and offers a split bedroom floor plan, making it ideal for comfort and convenience. Enjoy a relaxing water view from the rear of the home, perfect for peaceful contemplation. The open floor plan features wood-look tile throughout the living spaces, creating a warm and

    Cathy McCarthy RE/MAX REALTEC GROUP INC

    40 Sylvia Place, Oldsmar, FL 34677
  • /7

    $242,999

    • Land
    • 0.91 Acre
    • $267,032 per Acre

    910 Waverly St, Oldsmar, FL 34677

    This vacant lot offers an excellent opportunity to build your future home or make a smart investment. Situated in a desirable neighborhood, the property features 0.91 acres of wooded terrain. Public water is available, and septic is required. Enjoy a peaceful setting while remaining conveniently located near shopping, dining, schools, and major highways, providing easy access to city amenities.

    Zach Hilferding NEW ALLIANCE GROUP REALTY

    910 Waverly St, Oldsmar, FL 34677
  • /18

    $294,900

    • 2 Beds
    • 2 Baths
    • 1,086 Sq Ft

    209 Hemingway Dr, Oldsmar, FL 34677

    Stunning Sun Ketch Townhome | Bright, Airy & Move-In Ready! Welcome to your slice of paradise in the highly sought-after Sun Ketch community of Oldsmar! This meticulously maintained 2-bedroom, 2-bathroom townhome offers the perfect blend of style, comfort, and convenience.Step inside to find gorgeous, rich cherry floors that flow through the living spaces, adding warmth and a touch of luxury

    Melissa Hinchliffe SMITH & ASSOCIATES REAL ESTATE

    209 Hemingway Dr, Oldsmar, FL 34677
  • /48

    $256,000

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    433 Sailfish Blvd, Oldsmar, FL 34677

    SPECTACULAR VIEWS! Welcome home to your quaint, cozy - yet surprisingly spacious - cottage nestled along a serene pond directly across from a peaceful tropical bird sanctuary in the heart of Oldsmar, Florida! This beautifully updated 2-bedroom, 2-bathroom home features cathedral ceilings, along with a bright open-concept layout with a generous living room and dining area – perfect for

    Anne Hode AH REALTY SERVICES, LLC

    433 Sailfish Blvd, Oldsmar, FL 34677
  • /25

    $239,000

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

    104 E Cypress Ct Unit 104, Oldsmar, FL 34677

    Located in East Lake Woodlands this quiet private second-story unit offers serene views overlooking the golf course and has a bright welcoming interior. Thoughtfully remodeled throughout, the home features abundant cabinet space, newer appliances, and major system upgrades including air conditioner and furnace. The unit has been tastefully finished with beautiful Florida-style decor, creating a

    Stephen Hachey FLAT FEE MLS REALTY

    104 E Cypress Ct Unit 104, Oldsmar, FL 34677
  • /21

    $235,000

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    80 Lance Ct, Oldsmar, FL 34677

    Motivated Seller!! Welcome to this spacious, TURN KEY Villa located in the HIGHLY DESIRABLE Country Club, Golf and Tennis Community of Eastlake Woodlands. The solid block constructed END UNIT home offers extra outdoor space for relaxing with family and friends. As you approach this end unit at the end of a peaceful cul-de-sac you'll find space to the right of the front door for storage, closet

    Casey Riordan LPT REALTY, LLC

    80 Lance Ct, Oldsmar, FL 34677
  • /35

    $249,000

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

    80 Birdsong Ct, Oldsmar, FL 34677

    Located in the desirable 24-hour guard-gated community of East Lake Woodlands, this one-story villa with attached garage offers privacy, potential, and key updates. Surrounded by mature wooded landscaping, sidewalks throughout the neighborhood provide safe walking opportunities with occasional views of native wildlife. With no age limit and nominal pet restrictions, this community has everything

    Donna Nettestad RE/MAX ACTION FIRST OF FLORIDA

    80 Birdsong Ct, Oldsmar, FL 34677
  • /53

    $279,900

    • 2 Beds
    • 2 Baths
    • 1,201 Sq Ft

    235 Woods Landing Trail, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Move-in ready and tucked inside one of Oldsmar’s most established gated communities, East Lake Woodlands, this townhome offers low-maintenance living with peaceful pond views and thoughtful updates throughout. The kitchen features updated cabinetry, crisp white quartz countertops (2025), stainless steel appliances, and a dining area that flows

    Kelsi Ward SOUTHERN LIFE REALTY

    235 Woods Landing Trail, Oldsmar, FL 34677
  • /52

    $249,000

    • 2 Beds
    • 2 Baths
    • 1,671 Sq Ft

    428 Pelican Dr S, Oldsmar, FL 34677

    Just listed in the 55+ Gull-Aire Village: This spacious 1993 Jacobsen home offers 1,671 square feet of living space in a quiet setting. Upon entry, you will find a large veranda room featuring a built-in wet bar and custom storage. Abundant windows keep the interior bright, while cathedral ceilings add to the sense of openness. The sizable indoor laundry area includes a built-in counter, making

    Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

    428 Pelican Dr S, Oldsmar, FL 34677
  • /9

    $200,000

    • Land
    • 0.19 Acre
    • $1,052,632 per Acre

    503 Buckingham Ave W, Oldsmar, FL 34677

    Prime Vacant Lot – Oldsmar, FL - Exceptional opportunity to build in a prime Oldsmar location just one block from waterway to Safety Harbor. This cleared and leveled vacant lot is ideally situated near top-rated schools, parks, restaurants, and the charming downtown of Safety Harbor. Convenient access to Tampa International Airport and major roadways makes commuting a breeze.Located in an

    Jourdin Reece GULF SHORES REALTY ERA POWERED LLC

    503 Buckingham Ave W, Oldsmar, FL 34677
  • /14

    $230,000

    • 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
  • /15

    $225,000

    • 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. Brand new fresh carpets. 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,

    Lin Huang CHARLES RUTENBERG REALTY INC

    244 Countryside Key Blvd, Oldsmar, FL 34677
  • /63

    $215,000

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    113 Woodlake Wynde Unit 19, Oldsmar, FL 34677

    Looking for a 2 bedroom 2 bath 1st floor end unit condo? Well your search is over. Are you wanting a gated country club and golfing community with amenities galore? This is the property for you. From the moment you enter the gates of this Eastlake Woodland Woodlake Run community you will be met with beautiful landscaping, walking paths, golf courses and just an overall serene feeling. The condo

    Lilly Esposito CENTURY 21 RE CHAMPIONS

    113 Woodlake Wynde Unit 19, Oldsmar, FL 34677
  • /40

    $210,000

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    83 Pelican Dr N, Oldsmar, FL 34677

    Discover exceptional value in Gull-Aire Village, a vibrant 55+ community, with this meticulously maintained home ready for its next owner. Move right in! this sale includes all furnishings and contents, including a 60-inch TV, for a seamless transition. Enjoy peace of mind with a host of recent upgrades: In March of 2024 a brand-new shingle roof, 11 new hurricane windows, and 11 new solar panels

    Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

    83 Pelican Dr N, Oldsmar, FL 34677
  • /34

    $258,000

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

    291 Countryside Key Blvd, Oldsmar, FL 34677

    Welcome to the highly sought-after gated community of Countryside Key, ideally located in the heart of Oldsmar! This well-maintained home offers wood laminate flooring, a convenient ground-level laundry closet, and a screened-in lanai with an additional storage closet—perfect for relaxed Florida living. The kitchen opens seamlessly to the dining and living areas, creating an inviting open-concept

    Tanner Tillung EXP REALTY LLC

    291 Countryside Key Blvd, Oldsmar, FL 34677
  • /37

    $255,000

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

    475 Woods Landing Trail Unit 1, Oldsmar, FL 34677

    Welcome home to this beautifully updated Townhouse in the sought after East Lake Woodlands Gated Community. The views from the enclosed Florida room offering wooded pond view, wildlife and complete serenity. This home features 2 bedroom, 2.5 baths, private driveway with car port and storage shed, updated kitchen with granite countertops and stainless steel appliances. In the kitchen is a sliding

    Loren Roye THE KEYES COMPANY - SARASOTA

    475 Woods Landing Trail Unit 1, Oldsmar, FL 34677
  • /34

    $244,900

    • 2 Beds
    • 2 Baths
    • 1,573 Sq Ft

    101 Dolphin Dr N, Oldsmar, FL 34677

    Welcome Home! Your move-in ready and partially furnished Florida retreat with a warm, contemporary flair awaits you in the heart of Oldsmar. This spacious 2-bedroom, 2-bath home is situated on a rare DOUBLE LOT (7,854 sq. ft.), that YOU OWN offering privacy and flexibility. The open and inviting floor plan features cathedral ceilings and newer laminate flooring throughout the family room,

    Anne Hode AH REALTY SERVICES, LLC

    101 Dolphin Dr N, Oldsmar, FL 34677
  • /21

    $270,000

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    123 Dolphin Dr S, Oldsmar, FL 34677

    Beautiful remodeled home. Move in ready. Plantation shutters thoughout. All new porcelain tile, new appliances. Freshly painted inside and out. Tiled kitchen with open shelving with large corner windows that allow for the light to fill the room. Spacious living and dinning room with a open floor plan. Primary bedroom has adjoining ensuite with bay windows and walkin closet. Guest Bedroom is also

    Ruthann Underwood PAM RYAN REALTY INC

    123 Dolphin Dr S, Oldsmar, FL 34677
  • /29

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft

    645 Timber Bay Cir E, Oldsmar, FL 34677

    Rare opportunity with an assumable VA loan—potential buyers can step into favorable financing, subject to lender approval Your Renovation Dream Home! This home is in the desirable Shoreview Subdivision situated on 1/3 of an acre of land. After necessary rehab this home will easily be the jewel of the subdivision located a short walking distance from Tampa Bay and Mobbly Beach Park!! The home is

    Michael Eddings MARK SPAIN REAL ESTATE

    645 Timber Bay Cir E, Oldsmar, FL 34677
  • /31

    $239,000

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

    117 E Cypress Ct Unit 117, Oldsmar, FL 34677

    **COME ON IN - MAKE YOURSELF AT HOME ** This 2 Bed 2 Bath GROUND FLOOR unit has been totally REMODELLED to an exceptionally high standard!! New Floors, New Bathrooms, New Windows, MOVE IN READY!! And what's more?? NOT OVERLOOKED at the rear!!! Enjoy your morning coffee or evening drink on the front enclosed patio or watch the wildlife from the rear patio .. you have a choice!! Within easy walking

    Joanne Todd RE/MAX REALTEC GROUP INC

    117 E Cypress Ct Unit 117, Oldsmar, FL 34677
  • /16

    $284,900

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    140 Joanne Place, Oldsmar, FL 34677

    This well maintained 2 bedroom 2 bath villa in Quail Forest tucked away in the gated East Lake Woodlands Community is now available for you! The open floor plan and wet bar create a great entertaining area. Both ensuite bedrooms feature plenty of closet space and sliders that open to the finished Florida room. The Florida room overlooks a serene back yard where deer walk through. You will enjoy

    Doug Addeo COMMUNITY REALTY ASSOCIATES

    140 Joanne Place, Oldsmar, FL 34677
  • /25

    $249,900

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    260 Balsam Dr, Oldsmar, FL 34677

    SIGNIFICANT PRICE DECREASE!!! Owners are motivated!!! This desirable end-unit villa in exclusive East Lake Woodlands combines comfort, privacy, and an ideal layout for everyday living or entertaining. Featuring two spacious primary suites, each with its own ensuite bath and split floor plan design, the home provides excellent privacy for residents and guests alike. The open layout includes a

    Colleen Monagas MARC JOSEPH REALTY, INC

    260 Balsam Dr, Oldsmar, FL 34677
  • /30

    $244,900

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    209 Corkwood Ln, Oldsmar, FL 34677

    Amazing Location, Renovated, New kitchen, New Water heater, New Bathroom Vanity, New flooring, Quartz counter tops and new appliances and there is a Storage room next to the car port and a Privacy back yard area. Good location next to Walmart supercenter Oldsmar and a few minutes away to walk from supermarket Aldi. Great school district. Community has a pool, Tennis Courts, Basketball court.

    Genci Shurdha CHARLES RUTENBERG REALTY INC

    209 Corkwood Ln, Oldsmar, FL 34677
  • /45

    $205,900

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

    472 Trout Ln, Oldsmar, FL 34677

    Gull-Aire Village. 55+ community. Welcome to this 1998 Jacobsen home, built to newer standards and offering the perfect blend of comfort and convenience. This spacious residence features a desirable split floor plan with three bedrooms, providing ample privacy for family or guests. The chef’s kitchen is a true highlight, boasting high-quality Kraft Maid Cabinetry with custom pull-outs for

    Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

    472 Trout Ln, Oldsmar, FL 34677
  • /20

    $225,000

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

    113 Nina Way, Oldsmar, FL 34677

    Here is your opportunity to purchase a great condo in the popular East lake Woodlands development. This beautiful 2 bedroom, 2 full bath condo has plentiful closet space, the primary bedroom has 3! Unit has its own washer and dryer located in the enclosed porch just off the living room. All furniture is included! Both bathrooms have been remodeled along with the kitchen. The kitchen has quartz

    Joseph Courey BRICK HOUSE REALTY SERVICES

    113 Nina Way, Oldsmar, FL 34677
  • /28

    $299,999

    • 3 Beds
    • 2 Baths
    • 1,255 Sq Ft

    163 Dolphin Dr E, Oldsmar, FL 34677

    Presenting a stunningly renovated beauty in Gull-Aire Village, a sought after 55+ golf cart and pet-friendly community on the north shores of Tampa Bay! If you're searching for your piece of Floridian paradise where no expense was spared for modernized living, then look no further! This wide open floor plan home will be sure to impress with EXQUISITE UPDATES and tons of fun bells and whistles.

    Micaela Morenz, PA BLAKE REAL ESTATE INC

    163 Dolphin Dr E, Oldsmar, FL 34677
  • /49

    $285,000

    • 2 Beds
    • 2 Baths
    • 1,910 Sq Ft

    1203 Clays Trail Unit 406, Oldsmar, FL 34677

    UNBELIEVVABLE VALUE in East Lake Woodlands!! 1203 Clays Trail #406 nestled in the highly sought after community of Eastlake Woodlands. This spacious 2bed/2bath condo has it all to include a 1 car garage and a fantastic layout. As you enter the condo there are stairs that take you up to the living area that features a beautiful kitchen in the center of the condo with a large living room to the

    John Bailey Jr BHHS FLORIDA PROPERTIES GROUP

    1203 Clays Trail Unit 406, Oldsmar, FL 34677
  • /37

    $255,000

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

    405 Woods Landing Trail, Oldsmar, FL 34677

    Short Sale. BANK APPROVED SHORT SALE - Welcome to the coveted East Lake Woodlands Gated Community. One of the first things you will notice when you walk in the door is the views to the back, featuring woods, water, wildlife and serenity. This beautiful 2 bedroom 2.5 bath townhouse features a carport, outside storage shed and large enclosed Florida room that opens with sliding doors from living

    Loren Roye THE KEYES COMPANY - SARASOTA

    405 Woods Landing Trail, Oldsmar, FL 34677

Home Trends in Oldsmar, FL

Housing Trends

Median Sale Price
$382,000
Median Single Family Sale Price
$520,000
Median Townhouse Sale Price
$387,500
Median 2 Bedroom Sale Price
$181,000
Median 1 Bedroom Sale Price
$167,000
Average Price Per Sq Ft
$249
Number of Homes for Sale
152
Last 12 months Home Sales
398
Months of Supply
4.60
Median List Price
$400,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
-3%
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