Fixer Upper homes for sale & real estate in Oldsmar, FL

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ABOUT THIS HOME
Fixer Upper for sale in Oldsmar, FL:
Welcome to 416 Woodward ave. , sitting on a half-acre double lot on the corner of Shore drive and Woodward ave. This 2,420 sq. ft. property includes four bedrooms and two bathrooms. The backyard is designed for entertaining with a large pool and spa, stone pavers, and a grotto-style setting surrounded by mature landscaping. The location is quiet and peaceful with no through traffic, while still close to all of the amenities Oldsmar has to offer. Oldsmar itself is a charming community about 30 minutes from Tampa. The home was impacted by last year’s hurricane and has been flood cut, so it will require renovation. However, several valuable features may be salvageable, including the meta

$395,000

4 beds2 baths2,420 sq ft

416 Woodward Ave, Oldsmar, FL 34677

Half-acre double lot • Large pool and spa • Grotto-style setting

3D WALKTHROUGH

ABOUT THIS HOME
Fixer Upper for sale in Oldsmar, FL:
Discover a rare opportunity to reimagine this charming fixer-upper on a premium lot backing to a tranquil pond, offering breathtaking water views and ultimate privacy in a quiet, low-traffic setting. Tucked away at the rear of the neighborhood, the property is enveloped by lush tropical landscaping, mature trees, and expansive green spaces that invite outdoor living. The home, impacted by recent storm flooding, has been stripped to the studs in many areas, revealing its solid structure and providing a clean slate for customization—ideal for renovation enthusiasts or those seeking to build anew. Inside, the open layout features striking exposed beams, multiple ceiling fans for comfort,

$280,000

3 beds2 baths1,116 sq ft

206 Dunkirk Rd, Oldsmar, FL 34677

Water views • Mature fruit trees • Tidal pond

ABOUT THIS HOME
Fixer Upper for sale in Oldsmar, FL:
* PRICED TO SELL! * Beautiful Lake Front View. No Rear Neighbors. Great Location! Short Walk to Sheffield Park. 2 Bedroom/2 Bath/2 Car Garage Home on A Nice Sized Lot. The Back Yard Is Completely Fenced-In and Large Enough for A Pool. This Is a Fixer-Upper with Lots of Potential. Block Construction. HVAC New In 2019, Electrical Panel Updated, Roof (2009). There is a Dividing Wall Between the Florida Room and Office. The Office Provides Another 270 Square feet that is Not Included in the Heated Square Footage. The Bedrooms are Good Sized and both with Ceiling Fans with Light Fixtures. Ceiling Fans in the Living Room and Dinette as well. The flooring is Tile, Terracotta Tile in The Florida R

$220,000

2 beds2 baths1,064 sq ft

704 Lemonwood Dr, Oldsmar, FL 34677

Park view • Lake front • No rear neighbors

ABOUT THIS HOME
Fixer Upper for sale in Oldsmar, FL:
* * NEW PRICE! * * Great Location! HUGE LOT! Fixer-upper with Lots of Potential! 3 Living Spaces - Income Producing Property. The Second Floor is the Main House with 3 Bedrooms and 2 Baths. The First Floor Can Be Used as Two Rentals or multi-generational living. Can Be Used As a Short Term Rental. This Property is with Beautiful Views of The Park and Tampa Bay from The Front Upstairs Balcony. Over-Sized Lot Is . 26 Acres. This Is a Concrete Block/ Stucco Home With 2,572 Sqft of Living Space with A Total Of 5 Bedrooms And 4 Baths. There Is A 2-Car Carport and Large Concrete Block Shed at The Back of The Property. The First Floor Apartments are Each with 1 Bedroom/ 1Bath/ Kitchen. The North

$390,000

5 beds4 baths2,572 sq ft

613 Chestnut St, Oldsmar, FL 34677

Short term rental • Oversized lot • 0.26 acre lot

ABOUT THIS HOME
Fixer Upper for sale in Oldsmar, FL:
Welcome to coastal country living in Oldsmar, Florida, at the top of Tampa Bay! The value of this property is in the land. It is all about the Land, it is about the promise the land holds for the next homeowner/investor/ Builder. This 148 x 184 property is primed for redevelopment. The house and outbuildings on the lot are likely tear-downs, not fixer-uppers. The roofs are compromised. The zoned R-2 parcel can be split into 2 lots. Your idea of mother/daughter housing, a single-family unit, or attached townhome style housing can be brought to life. The purchaser can build multi-residential on the lots. (not multi-family). The City of Oldsmar maintains jurisdiction over any proposed build

$480,000

2 beds1 bath898 sq ft

508 Dartmouth Ave E, Oldsmar, FL 34677

Zoned r-2 parcel • Split into 2 lots • Public utilities

Property at 204 Shore Dr W, Oldsmar, FL 34677, 3 beds, 2 baths

$380,000

3 beds2 baths1,374 sq ft

204 Shore Dr W, Oldsmar, FL 34677

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ABOUT THIS HOME
Fixer Upper for sale in Oldsmar, FL:
* MULTIPLE OFFERS RECEIVED, HIGHEST AND BEST DUE BY 10/27 AT 12PM. * INVESTORS! Take a look at this solid block home in the highly desired neighborhood of Beacon Groves. With a little TLC, this property could shine! With an open concept floorplan and vaulted ceilings, the kitchen and large living room will be an entertainer's dream. Three decently sized bedrooms and two baths complete this home with over 1400 square feet. Situated on a corner lot, the backyard is large and finished with two picturesque Oak Trees. The Hurricane-rated garage door (140mph) was just installed along with a new garage door opener strong enough to support such a heavy-duty door. Roof 2011, HVAC 2019, Water Heater

$300,000

3 beds2 baths1,413 sq ft

2102 Grove Valley Ave, Palm Harbor, FL 34683

8,181 sq ft lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
Fixer Upper for sale in Oldsmar, FL:
Welcome to this two-bedroom, two-bathroom villa located in the Steeplechase community of Palm Harbor. Offering 1,100 sq. ft. of living space and an oversized one-car attached garage, this home provides a comfortable layout and great potential for customization. The home features a large front brick patio, perfect for taking in the beautiful Florida weather or entertaining guests. While the property does need some TLC and updates, the layout and features provide a wonderful foundation to create your own personal retreat. Step inside to find vaulted ceilings and a split floor plan that offers both space and privacy. The kitchen features matching appliances, a separate pantry for extra organiz

$300,000

2 beds2 baths1,100 sq ft

106 Hunter Ct, Palm Harbor, FL 34684

3,433 sq ft lot • $380 HOA • Garage

ABOUT THIS HOME
Fixer Upper for sale in Oldsmar, FL:
LOCATION! MOTIVATED! LOCATION!! MOTIVATED! LOCATION!!!! Right in the middle of the Countryside area. .. .. .if being close to EVERYTHING is important to YOU. .. YOU will love this location. This home is 2 bedroom (both room are LARGE), 2 bath (one of which has been remodeled), 2 car garage on a beautifully oversized lot, which isn't found very often today. This home features a split plan with privacy for those occupying this home. Very spacious rooms with an additional family room and a screened outdoor room affords more space than most buyers have found in the Countryside area. A/C is 3 years old, Roof is 11 yrs old. Some TLC will go a long way in making this home even more in demand than

$470,000

2 beds2 baths1,622 sq ft

2700 Westchester Dr N, Clearwater, FL 33761

0.32 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
Fixer Upper for sale in Oldsmar, FL:
Wonderful fixer upper oozing with potential! This two bedroom/two bath double wide manufactured home is situated in Blue Jay Estates, an active 55+ community where you own your land. A low monthly fee of $230 a month includes escrow reserves, water, sewer, trash, lawn care, and more! Non flood zone! Eat in kitchen with sky light and room for a side bar or office. Dining room with large built in buffet. Laminate floors and overhead duct work so no floor registers. Square footage is 1152 which does not include an enclosed front porch or screened side porch. Plenty of storage in roomy shed with utility sink. Nicely Landscaped. Needs a little TLC to transform into your forever home. Blue Jay Es

$116,000

2 beds2 baths1,152 sq ft

203 Red Maple Dr, Palm Harbor, FL 34684

3,751 sq ft lot • $230 HOA • Community pool

ABOUT THIS HOME
Fixer Upper for sale in Oldsmar, FL:
CORPORATE OWNERSHIP, AN LLC, OR A PARTNERSHIP IS PROHIBITED. NO SELLER FINANCING AVAILABLE. This property was flooded and had some wind damage by the 2024 hurricanes. The condition is reflected in the reduced asking price. This home has great potential either as a fixer upper or this would also be a prime location for your new home! Plan a visit to Bay Aristocrat Village just to check out this waterfront community and the warm beautiful Florida waterfront lifestyle! The low monthly maintenance fee of only $360 includes lawn, trash, water and sewer. Located in beautiful Bay Aristocrat Village, one of Pinellas County's premier waterfront manufactured home communities, where you are a property

$45,000

1 bed1 bath552 sq ft

18675 US Highway 19 N #128, Clearwater, FL 33764

$360 HOA • Community pool • Car-dependent

ABOUT THIS HOME
Fixer Upper for sale in Oldsmar, FL:
This home needs some TLC — a solid two-story home in the well-regarded Palm Harbor neighborhood of Windmill Pointe. Home has 4 bedrooms, 3 full bathrooms, and an open layout downstairs. One bedroom and and one full bath located downstairs. This home sits on a generously sized lot and features a pool, private fenced backyard, mature landscaping, and room for upgrades that can significantly boost its value. This is a rare find for investors, flippers, or buyers with the vision and resources to unlock its full potential. Remediation was done in 2005, home has been insured through State Farm for approx $2500/year for as long as current owner has had the property.

$460,000

4 beds3 baths1,818 sq ft

2823 Wycombe Way, Palm Harbor, FL 34685

7,475 sq ft lot • $33 HOA • 2 garage spots

Property at 3064 Homestead Oaks Dr, Clearwater, FL 33759, 4 beds, 2 baths

$879,999

4 beds2 baths2,359 sq ft

3064 Homestead Oaks Dr, Clearwater, FL 33759

Property at 1619 Whithorn Pl Unit D, Palm Harbor, FL 34684, 1 bed, 1 bath

$114,900

1 bed1 bath814 sq ft

1619 Whithorn Pl Unit D, Palm Harbor, FL 34684

Property at 2670 Barksdale Ct, Clearwater, FL 33761, 3 beds, 2 baths

$195,000

3 beds2 baths1,405 sq ft

2670 Barksdale Ct, Clearwater, FL 33761

Property at 1008 W Lennox Rd W, Palm Harbor, FL 34683, 2 beds, 2 baths

$239,900

2 beds2 baths1,050 sq ft

1008 W Lennox Rd W, Palm Harbor, FL 34683

Property at 24862 US Highway 19 N #1902, Clearwater, FL 33763, 1 bed, 1 bath

$97,000

1 bed1 bath593 sq ft

24862 US Highway 19 N #1902, Clearwater, FL 33763

Property at 2650 Countryside Blvd Unit C106, Clearwater, FL 33761, 2 beds, 2 baths

$155,000

2 beds2 baths1,070 sq ft

2650 Countryside Blvd Unit C106, Clearwater, FL 33761

Property at 24862 US Highway 19 N #104, Clearwater, FL 33763, 1 bed, 1 bath

$75,900

1 bed1 bath593 sq ft

24862 US Highway 19 N #104, Clearwater, FL 33763

Property at 2620 Trent Rd, Palm Harbor, FL 34684, 4 beds, 3 baths

$530,000

4 beds3 baths3,640 sq ft

2620 Trent Rd, Palm Harbor, FL 34684

Property at 2880 Cinnamon Bear Trl, Palm Harbor, FL 34684, 2 beds, 2 baths

$289,000

2 beds2 baths896 sq ft

2880 Cinnamon Bear Trl, Palm Harbor, FL 34684

Property at 2348 Shelley St #1, Clearwater, FL 33765, 2 beds, 1 bath

$114,900

2 beds1 bath913 sq ft

2348 Shelley St #1, Clearwater, FL 33765

Property at 2058 Dodge St, Clearwater, FL 33760, 2 beds, 2 baths

$325,000

2 beds2 baths1,031 sq ft

2058 Dodge St, Clearwater, FL 33760

Property at 2228 Hannah Way S, Dunedin, FL 34698, 4 beds, 2.5 baths

$699,900

4 beds2.5 baths3,120 sq ft

2228 Hannah Way S, Dunedin, FL 34698

Property at 6673 146th Ave N, Clearwater, FL 33764, 1 bed, 1 bath

$500,000

1 bed1 bath480 sq ft

6673 146th Ave N, Clearwater, FL 33764

Property at 2980 Haines Bayshore Rd #124, Clearwater, FL 33760, 2 beds, 2.5 baths

$275,000

2 beds2.5 baths1,210 sq ft

2980 Haines Bayshore Rd #124, Clearwater, FL 33760

Based on information submitted to the MLS GRID as of Mon Oct 27 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Fixer Upper Homes for Sale in Oldsmar

There are currently 6 fixer upper homes for sale in Oldsmar at a median listing price of $399K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Oldsmar stay on the market for 90 days. Popular neighborhoods include Gull Aire Village, Twin Branch Acres, Bridgeport, East Lake Woodlands, and Briar Creek. This map is refreshed with the newest listings in Oldsmar every 15 minutes.

In the past month, 18 homes have been sold in Oldsmar. In addition to houses in Oldsmar, there were also 10 condos, 26 townhouses, and 1 multi-family unit for sale in Oldsmar last month. Find your dream home in Oldsmar using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Oldsmar are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Oldsmar. Our Oldsmar real estate stats and trends will give you more information about home buying and selling trends in Oldsmar. If you're looking to sell your home in the Oldsmar area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Oldsmar with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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