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Oldsmar, FL Homes for Sale under $300,000

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  • /36

    $224,900

    • 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

    Agent Photo

    Jamie Everett

    FUTURE HOME REALTY INC

    (813) 733-6871

    145 Blue Marlin Dr, Oldsmar, FL 34677
  • /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
  • /16

    $275,000

    • Land
    • 1.13 Acres
    • $243,363 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

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    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
  • /44

    $270,000

    • 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
  • /33

    $256,000

    • 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
  • /52

    $289,000

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

    248 Hemingway Dr, Oldsmar, FL 34677

    Experience the best of Florida living—without the worry of flooding! This beautifully maintained 2-bedroom, 2-bath townhome is proudly NOT located in a FLOOD ZONE, offering you peace of mind, lower insurance costs, and a safe haven to call your own. Nestled within the highly sought-after Sun Ketch Townhomes at Cypress Lakes, this home welcomes you with a charming, tree-lined neighborhood where

    Lessie Reyes DALTON WADE INC

    248 Hemingway Dr, Oldsmar, FL 34677
  • /49

    $299,000 Open Sun 10AM - 1PM

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

    1203 Clays Trail Unit 406, Oldsmar, FL 34677

    SELLERS ARE OFFERING A $10,000.00 BUYER CREDIT AT CLOSING WITH A FULL PRICE OFFER!! 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

    John Bailey Jr BHHS FLORIDA PROPERTIES GROUP

    1203 Clays Trail Unit 406, 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
  • /37

    $274,000

    • 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

    $265,000

    • 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
  • /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 TOMLIN, ST CYR & ASSOCIATES LLC

    503 Buckingham Ave W, 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
  • /21

    $282,000

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

    80 Lance Ct, Oldsmar, FL 34677

    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 for trash cans,

    Casey Riordan LPT REALTY, LLC

    80 Lance Ct, Oldsmar, FL 34677
  • /37

    $224,900

    • 2 Beds
    • 2 Baths
    • 1,052 Sq Ft

    427 Pelican Dr S, Oldsmar, FL 34677

    Beautifully Updated & Move-In Ready in Gull-Aire Village. This spacious 2-bed, 2-bath manufactured home offers 1,239 sq ft of air-conditioned living, including a newly enclosed Florida Room (2022). Enjoy an open floor plan with high ceilings, stylish VINYL PLANK flooring (2021), and Brand-New Stainless Steel Appliances with a double oven (2024). Major upgrades include NEW WINDOWS (2019) and CPVC

    Andrea Bladt Knudsen CHARLES RUTENBERG REALTY INC

    427 Pelican Dr S, Oldsmar, FL 34677
  • /25

    $289,900

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

    260 Balsam Dr, Oldsmar, FL 34677

    SIGNIFICANT PRICE DECREASE!!! 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 welcoming family room, a

    Colleen Monagas MARC JOSEPH REALTY, INC

    260 Balsam Dr, Oldsmar, FL 34677
  • /27

    $299,000

    • Land
    • 0.91 Acre
    • $328,571 per Acre

    0 Strathmore Ave, Oldsmar, FL 34677

    Discover the potential of this rare, untouched piece of land located in the heart of charming Oldsmar. Whether you're planning to build your forever home or exploring investment opportunities—like developing rental properties—this lot offers incredible flexibility. With just under an acre to work with and no HOA restrictions, you're free to bring your vision to life without limitations. The

    Jurandir Alves ALIGN RIGHT REALTY CARROLLWOOD

    0 Strathmore Ave, Oldsmar, FL 34677
  • /34

    $254,900 Open Sat 11:30AM - 2PM

    • 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
  • /29

    $295,000

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

    645 Timber Bay Cir E, Oldsmar, FL 34677

    2.875% Rate Assumable VA with Roam! 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 priced substantially below market value to attract CASH Buyers understanding the home

    Michael Eddings MARK SPAIN REAL ESTATE

    645 Timber Bay Cir E, 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
  • /33

    $299,900

    • 4 Beds
    • 2 Baths
    • 1,550 Sq Ft

    20 Sylvia Place, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. HUGE PRICE IMPROVEMENT to under $300K! Just $440/month HOA covers EVERYTHING: Roof, Lawn, Cable, Internet, Pest Control & More! This is the lock-and-leave Florida lifestyle you've been searching for—and it just became $10,000 more attainable. Discover this well maintained 3-bedroom, 2-bath villa PLUS dedicated office in a gated community. With a new

    Kera Arnone CHARLES RUTENBERG REALTY INC

    20 Sylvia Place, Oldsmar, FL 34677
  • /32

    $229,500

    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    148 Douglas Rd W Unit C, Oldsmar, FL 34677

    Move- in ready 2-bedroom 2 bath town home in Oldsmar Fl. 2 parking spots available low HOA at $87.00 per month. Easy leasing Ergo Friendly fenced back yard and porch area. Brand new roof, hot water tanks 2025, various new windows replaced 2025. All brand-new flooring, kitchen and 2 bathrooms granite counters completed in 2025. Inside laundry. All appliances remain with sale. Completely remodeled

    Robert VanPamelen ARCHWATER REALTY LLC

    148 Douglas Rd W Unit C, Oldsmar, FL 34677
  • /48

    $255,500

    • 2 Beds
    • 2 Baths
    • 1,392 Sq Ft

    121 Dolphin Dr S, Oldsmar, FL 34677

    This meticulously maintained Florida home with a coastal vibe awaits you in centrally located Oldsmar! Tucked in a quiet corner of Gull-Aire Village you can relax on your tranquil, oversized side-patio surrounded by magnificent palm trees and lush landscaping. This beautiful furnished, move-in ready 2 bedroom/2 bathroom home features luxury vinyl plank flooring, crown molding, upgraded doors and

    Anne Hode AH REALTY SERVICES, LLC

    121 Dolphin Dr S, Oldsmar, FL 34677
  • /30

    $244,900

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    209 Corkwood Ln, Oldsmar, FL 34677

    Amazing Location, Renovated, New kitchen, Quartz counter tops and new appliances and there is a Storage room next to the car port. 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. Additional conveniences include a storage room and assign covered parking. The HOA

    Genci Shurdha CHARLES RUTENBERG REALTY INC

    209 Corkwood Ln, 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
  • /35

    $259,000

    • 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
  • /57

    $247,000

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

    106 Lakeview Place, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. Fully remodeled 2 bedroom, 2 bathroom, second floor condo now available in the highly sought after gated community of East Lake Woodlands. You will first notice the open kitchen with new cabinets, quartz countertops, stainless steel appliances, and new hardware. There is room for a table and chairs to create an eat-in kitchen if desired. The living

    Mary White SOUTHERN LIFE REALTY

    106 Lakeview Place, Oldsmar, FL 34677
  • /40

    $215,000

    • 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
  • /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
  • /31

    $218,000

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    129 Woodlake Wynde Unit 129, Oldsmar, FL 34677

    Welcome to Your New Home in East Lake Woodlands! Discover comfort, functionality, and Florida living in this spacious 2-bedroom, 2-bath condo located in the highly sought-after, gated community of East Lake Woodlands.The inviting primary suite features both a walk-in closet and an additional closet, along with a private ensuite bath featuring a tub/shower combination. Step directly onto the

    Liliana Rincon BILTMORE GROUP INC

    129 Woodlake Wynde Unit 129, Oldsmar, FL 34677
  • /14

    $235,000

    • 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
  • /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
  • /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

Home Trends in Oldsmar, FL

Housing Trends

Median Sale Price
$370,000
Median Single Family Sale Price
$515,000
Median Townhouse Sale Price
$393,000
Median 2 Bedroom Sale Price
$189,000
Median 1 Bedroom Sale Price
$167,000
Average Price Per Sq Ft
$250
Number of Homes for Sale
127
Last 12 months Home Sales
399
Months of Supply
3.80
Median List Price
$395,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-8%
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