Real Estate Investment Properties for Sale in Oldsmar, FL
Looking for investment property in Oldsmar, FL with high ROI ?
Explore a variety of short-term homes & houses in Oldsmar, FL. Invest wisely with VRBO & Oldsmar, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Oldsmar, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
502 TIMBER BAY CIRCLE EOldsmar, FLWelcome to this stunningly spacious and well-maintained pool home nestled in one of the mo... |
4 beds | 2 baths | 1,658 sq.ft. |
$448,000 |
Airbnb cash on cash: 6.17%
|
1640 GRAY BARK DRIVEOldsmar, FLWelcome to the home that truly has everything! No detail has been overlooked in this fully... |
3 beds | 2 baths | 1,927 sq.ft. |
$585,000 |
Airbnb cash on cash: 2.73%
|
2002 SHEFFIELD COURTOldsmar, FLThis spacious and well-maintained 2 bedroom 2 bath end-unit Villa offers an exceptional fl... |
2 beds | 2 baths | 1,296 sq.ft. |
$219,000 |
Airbnb cash on cash: 5.13%
|
102 BRENT CIRCLEOldsmar, FLHuge Price Reduction immediate equity! Ready to move into. Seller Says Sell! Seller is Re... |
3 beds | 3 baths | 1,834 sq.ft. |
$360,000 |
Airbnb cash on cash: 5.65%
|
632 LAKE CYPRESS CIRCLEOldsmar, FLUnder contract-accepting backup offers. Reduced. Florida Pool Home! Welcome to your brigh... |
4 beds | 2 baths | 1,906 sq.ft. |
$563,000 |
Airbnb cash on cash: 4.66%
|
1203 CLAYS TRAIL #406Oldsmar, FLWelcome to 1203 Clays Trail #406 nestled in the highly sought after community of Eastlake ... |
2 beds | 2 baths | 1,910 sq.ft. |
$329,000 |
Airbnb cash on cash: 3.95%
|
436 LAFAYETTE BOULEVARDOldsmar, FLOne or more photo(s) has been virtually staged. Must see this 4 bedroom/2.5 bath home with... |
4 beds | 3 baths | 2,695 sq.ft. |
$800,000 |
Airbnb cash on cash: 2.39%
|
2044 SHEFFIELD COURTOldsmar, FLHigh and dry with NEW ROOF and NEW HVAC!! Welcome to this charming 2-bedroom, 2-bathroom ... |
2 beds | 2 baths | 1,296 sq.ft. |
$237,000 |
Airbnb cash on cash: 5.46%
|
130 SABAL COURT #COldsmar, FLWelcome to your charming retreat at 130 Sabal Ct. Unit C, is nestled in the heart of Oldsm... |
2 beds | 2 baths | 915 sq.ft. |
$189,000 |
Airbnb cash on cash: 7.3%
|
200 GRETCHEN COURTOldsmar, FLWELCOME HOME! Enjoy maintenance free Living in this Gated Community of Quail Forest which ... |
3 beds | 2 baths | 1,445 sq.ft. |
$374,900 |
Airbnb cash on cash: 4.03%
|
382 ROSALIND LANEOldsmar, FLWelcome to 382 Rosalind Ln., an extraordinary home in the exclusive gated community of Bay... |
4 beds | 3 baths | 3,273 sq.ft. |
$852,990 |
Airbnb cash on cash: 2.35%
|
2052 SHEFFIELD COURTOldsmar, FLOne or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available a... |
2 beds | 2 baths | 1,296 sq.ft. |
$255,000 |
Airbnb cash on cash: 4.42%
|
134 SYCAMORE LANE #HOldsmar, FLThis beautifully maintained 2 bedroom, 2 bath condo in fantastic Gardens of Forest lakes, ... |
2 beds | 2 baths | 915 sq.ft. |
$174,000 |
Airbnb cash on cash: 7.64%
|
396 COUNTRYSIDE KEY BOULEVARDOldsmar, FLWelcome to this beautifully updated 2-bedroom, 2.5-bathroom townhouse with 1,110 square fe... |
2 beds | 3 baths | 1,110 sq.ft. |
$287,000 |
Airbnb cash on cash: 4.66%
|
150 TADS TRAILOldsmar, FLVILLA with TRANQUIL GOLF COURSE VIEWS IN EAST LAKE WOODLANDS. This well Maintained VILLA... |
3 beds | 2 baths | 1,695 sq.ft. |
$379,500 |
Airbnb cash on cash: 3.32%
|
112 BRENT CIRCLEOldsmar, FLNow Offered at $529,900 â Waterfront Townhome with Deeded Boat Slip in Oldsmar! This bea... |
3 beds | 3 baths | 1,834 sq.ft. |
$529,900 |
Airbnb cash on cash: 2.23%
|
1516 E LAKE WOODLANDS PARKWAYOldsmar, FLWELCOME TO GREENHAVEN IN AN EXCLUSIVE GATED GOLF COURSE COMMUNITY OF EAST LAKE WOODLANDS. ... |
4 beds | 3 baths | 2,642 sq.ft. |
$749,000 |
Airbnb cash on cash: 2.03%
|
214 MEADOW LANE #214Oldsmar, FLClean and move-in ready Furnished 2/2 in The Meadows at East Lake Woodlands~~Income produc... |
2 beds | 2 baths | 879 sq.ft. |
$220,000 |
Airbnb cash on cash: 3.73%
|
1232 HOLLY CIRCLEOldsmar, FLWelcome to a piece of paradise in Forest Lakes, Oldsmar, where peaceful living meets capti... |
3 beds | 2 baths | 1,186 sq.ft. |
$390,000 |
Airbnb cash on cash: 5.52%
|
210 MARTHA LANE #210Oldsmar, FLWelcome to this charming 2-bedroom, 2-bathroom condo in the highly sought-after gated comm... |
2 beds | 2 baths | 1,094 sq.ft. |
$199,900 |
Airbnb cash on cash: 5.13%
|
124 NINA WAY #24Oldsmar, FLHUGE PRICE REDUCTION! Stunning 2 Bedroom, 2 Bathroom Remodeled Condo in East Lake Woodland... |
2 beds | 2 baths | 1,094 sq.ft. |
$197,900 |
Airbnb cash on cash: 6.5%
|
163 BRENT CIRCLEOldsmar, FL** Deeded Boat Slip with Lift **Nestled in a serene, small gated community, this exquisite... |
3 beds | 3 baths | 1,834 sq.ft. |
$565,000 |
Airbnb cash on cash: 2.08%
|
2000 SHEFFIELD COURTOldsmar, FLWelcome to this Beautifully UPDATED 1296 sq ft, 2-bedroom, 2-bath villa with VAULTED CEILI... |
2 beds | 2 baths | 1,296 sq.ft. |
$269,000 |
Airbnb cash on cash: 4.61%
|
321 SHORE DRIVE EOldsmar, FLWelcome to this beautiful Home, fully remodeled ,4-bedroom, 2 bath. And step outside to yo... |
4 beds | 2 baths | 1,523 sq.ft. |
$465,000 |
Airbnb cash on cash: 6.32%
|
826 CHRISTINA CIRCLEOldsmar, FLJust Reintroduced at a New Price â The Best Lot in this highly desired Community! Motiva... |
3 beds | 2 baths | 2,164 sq.ft. |
$1,275,000 |
Airbnb cash on cash: 0.31%
|
341 BAY ARBOR BOULEVARDOldsmar, FLSpectacularly remodeled home nestled on a conservation/pond lot in a gated community of Ba... |
3 beds | 2 baths | 2,034 sq.ft. |
$624,900 |
Airbnb cash on cash: 2.23%
|
150 POOLE PLACEOldsmar, FLWelcome to this stunning, fully renovated 3 bedroom, 2 bathroom East Lake Woodlands villa ... |
3 beds | 2 baths | 1,550 sq.ft. |
$375,000 |
Airbnb cash on cash: 4.32%
|
4797 STONEBRIAR DRIVEOldsmar, FLUnder contract-accepting backup offers. Donât miss this beautifully upgraded and meticul... |
4 beds | 3 baths | 2,486 sq.ft. |
$749,999 |
Airbnb cash on cash: 2.72%
|
367 COUNTRYSIDE KEY BOULEVARDOldsmar, FLMotivated Seller!! Move-in ready townhome in Oldsmar. Step into style and peace of mind ... |
2 beds | 2 baths | 1,105 sq.ft. |
$250,000 |
Airbnb cash on cash: 3.7%
|
40 GRETCHEN COURTOldsmar, FLStep through the front door of this charming villa, and you feel at home. The welcoming o... |
2 beds | 2 baths | 1,502 sq.ft. |
$345,000 |
Airbnb cash on cash: 2.21%
|
30 TADS TRAILOldsmar, FLMove in ready corner unit villa in desirable Eastlake woodlands gated community. All the w... |
3 beds | 2 baths | 1,450 sq.ft. |
$410,000 |
Airbnb cash on cash: 3.08%
|
316 LAFAYETTE BOULEVARDOldsmar, FLLive the ultimate Florida lifestyle in this spectacular Craftsman-style home in the heart ... |
4 beds | 4 baths | 2,848 sq.ft. |
$640,000 |
Airbnb cash on cash: 3.78%
|
1630 GRAY BARK DRIVEOldsmar, FLUnder contract-accepting backup offers. Welcome home to 1630 Gray Bark Drive! This beautif... |
3 beds | 2 baths | 1,358 sq.ft. |
$465,000 |
Airbnb cash on cash: 3.33%
|
267 COUNTRYSIDE KEY BOULEVARDOldsmar, FLUnder contract-accepting backup offers. Welcome to this Beautifully Updated 2-bedroom, 2.5... |
2 beds | 3 baths | 1,110 sq.ft. |
$263,900 |
Airbnb cash on cash: 2.93%
|
10 ARBOR LANEOldsmar, FLBRAND NEW AC / NEW ROOF 2022 / POOL RE-SURFACED 2018 / RARE TO MARKET GOLF COURSE FRONTAGE... |
4 beds | 2 baths | 2,318 sq.ft. |
$679,000 |
Airbnb cash on cash: 3.05%
|
303 NATIONAL ORANGE AVENUEOldsmar, FLPRICE ADJUSTMENT ON THIS WONDERFUL HOME! Updated and charming 3-bedroom homes in Oldsmar.... |
3 beds | 2 baths | 1,744 sq.ft. |
$450,000 |
Airbnb cash on cash: 3.61%
|
106 CUTLASS WAYOldsmar, FLFully updated and move-in ready 3-bedroom, 2.5-bath townhome in highly desirable Hayes Par... |
3 beds | 3 baths | 1,365 sq.ft. |
$375,000 |
Airbnb cash on cash: 4.17%
|
1631 SHADY OAKS DRIVEOldsmar, FLJUST REDUCED â DONâT MISS OUT ON THIS ONE! Come see this exceptional 3 bedroom, 2 bath... |
3 beds | 2 baths | 1,938 sq.ft. |
$614,500 |
Airbnb cash on cash: 2.26%
|
1608 SUNSET WIND LOOPOldsmar, FL**This home has over $90,000 in upgrades and has experienced NO flooding or water issues e... |
3 beds | 3 baths | 1,928 sq.ft. |
$500,000 |
Airbnb cash on cash: 1.84%
|
129 BRENT CIRCLEOldsmar, FLMOTIVATED SELLER - WATERVIEWS from All 3 Floors, This UPDATED 3Bed 3Bath townhome is situa... |
3 beds | 3 baths | 1,834 sq.ft. |
$569,000 |
Airbnb cash on cash: 2.25%
|
Real Estate investment in Oldsmar, FL
There are 167 properties for sale in the city of Oldsmar . The median list price in Oldsmar is $375,000 and the average price per square foot is $218. In September 2025, the average monthly cash on cash return in Oldsmar is 4.00%. The average monthly rental income in Oldsmar is $2,301.