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 |
|---|---|---|---|
438 LAFAYETTE BOULEVARDOldsmar, FLSeller is offering $10,000 toward Buyers Closing Cost! Custom built home is situated on ½... |
4 beds | 2 baths | 2,138 sq.ft. |
$599,900 |
Airbnb cash on cash: -0.03%
|
3858 SHORE BOULEVARDOldsmar, FLWelcome to Oldsmar, the highly desirable Tampa Bay suburb offering a perfect blend of smal... |
3 beds | 2 baths | 1,594 sq.ft. |
$1,200,000 |
Airbnb cash on cash: -0.95%
|
219 BAY ARBOR BOULEVARDOldsmar, FLMrs. Clean lived here!! This beautiful home is ready for its new owners! Vaulted ceilings ... |
4 beds | 3 baths | 1,873 sq.ft. |
$550,000 |
Airbnb cash on cash: -0.11%
|
1203 CLAYS TRAIL #406Oldsmar, FLUnder contract-accepting backup offers. UNBELIEVVABLE VALUE in East Lake Woodlands!! 1203 ... |
2 beds | 2 baths | 1,910 sq.ft. |
$285,000 |
Airbnb cash on cash: 1.58%
|
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. |
$700,000 |
Airbnb cash on cash: -0.51%
|
2044 SHEFFIELD COURTOldsmar, FLUnder contract-accepting backup offers. Short Sale. High and dry with NEW ROOF and NEW HVA... |
2 beds | 2 baths | 1,296 sq.ft. |
$190,000 |
Airbnb cash on cash: 2.37%
|
382 ROSALIND LANEOldsmar, FLUnder contract-accepting backup offers. NEW YEAR; NEW PRICE! Welcome to 382 Rosalind Ln., ... |
4 beds | 3 baths | 3,273 sq.ft. |
$822,000 |
Airbnb cash on cash: -0.4%
|
420 CYPRESS VIEW DRIVEOldsmar, FLUnder contract-accepting backup offers. Welcome to your private slice of paradise in Oldsm... |
3 beds | 2 baths | 1,870 sq.ft. |
$485,000 |
Airbnb cash on cash: -0.33%
|
1705 IRONWOOD COURT EOldsmar, FLWelcome to this beautifully renovated 2-bedroom, 2-bathroom homeâperfect for first-time ... |
2 beds | 2 baths | 1,206 sq.ft. |
$320,000 |
Airbnb cash on cash: 1.43%
|
201 DUNKIRK ROADOldsmar, FLUnder contract-accepting backup offers. Welcome to this beautifully updated Oldsmar proper... |
3 beds | 2 baths | 1,760 sq.ft. |
$390,000 |
Airbnb cash on cash: 0.52%
|
1598 LOCKMEADE PLACEOldsmar, FLUnder contract-accepting backup offers. Exquisite Estate Home in the Prestigious Aberdeen ... |
4 beds | 4 baths | 3,300 sq.ft. |
$999,900 |
Airbnb cash on cash: -0.75%
|
1909 CASTLE BAY COURTOldsmar, FL--SERIOUS SELLER-WILLING TO NEGOTIATE--SUBMIT YOUR OFFER ASAP-- Check out this BEAUTIFUL 3... |
3 beds | 2 baths | 1,410 sq.ft. |
$370,000 |
Airbnb cash on cash: 0.78%
|
388 COUNTRYSIDE KEY BOULEVARDOldsmar, FLUnder contract-accepting backup offers. 2025 HVAC! Assumable FHA Loan! Welcome to 388 Coun... |
2 beds | 2 baths | 1,105 sq.ft. |
$246,000 |
Airbnb cash on cash: N/A
|
120 BRENT CIRCLEOldsmar, FLAre you dreaming of your own stylish urban OASIS surrounded by nature yet minutes from eve... |
3 beds | 3 baths | 1,834 sq.ft. |
$520,000 |
Airbnb cash on cash: -2%
|
20 FERNBROOK ROADOldsmar, FLUnder contract-accepting backup offers. Tucked inside the 24-hour gated community of East ... |
4 beds | 2 baths | 2,147 sq.ft. |
$649,999 |
Airbnb cash on cash: -0.03%
|
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. |
$160,000 |
Airbnb cash on cash: 2.87%
|
604 LIMETREE DRIVEOldsmar, FLIf you love the beauty of Floridaâs outdoors, this home is a must-see. Just a short walk... |
3 beds | 3 baths | 1,430 sq.ft. |
$375,000 |
Airbnb cash on cash: 0.65%
|
100 KILSYTHE STREETOldsmar, FLTucked along picturesque Shore Drive E near the bay, this beautifully remodeled 3-bedroom,... |
3 beds | 3 baths | 1,100 sq.ft. |
$440,000 |
Airbnb cash on cash: -0.17%
|
1471 BRIARGROVE WAYOldsmar, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. Li... |
5 beds | 4 baths | 3,140 sq.ft. |
$899,999 |
Airbnb cash on cash: -0.2%
|
209 HEMINGWAY DRIVEOldsmar, FLStunning Sun Ketch Townhome | Bright, Airy & Move-In Ready! Welcome to your slice of par... |
2 beds | 2 baths | 1,086 sq.ft. |
$294,900 |
Airbnb cash on cash: 0.98%
|
1912 CUTTY BAY COURTOldsmar, FLMust see this beautiful 3 bedroom, 2 bathroom, 1 car garage pool home ideally situated in ... |
3 beds | 2 baths | 1,080 sq.ft. |
$325,000 |
Airbnb cash on cash: 1.14%
|
112 BRENT CIRCLEOldsmar, FLPRICE IMPROVEMENT! LUXURY MEETS UNBEATABLE VALUE. Skip the rehab and move right in to the ... |
3 beds | 3 baths | 1,834 sq.ft. |
$499,000 |
Airbnb cash on cash: -1.25%
|
129 CAMPHOR CIRCLE #COldsmar, FLWelcome to The Gardens of Forest Lakes, one of Oldsmarâs well-kept secret communities. T... |
2 beds | 2 baths | 915 sq.ft. |
$180,000 |
Airbnb cash on cash: 3.95%
|
948 LUCAS LANEOldsmar, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. Ar... |
3 beds | 2 baths | 1,685 sq.ft. |
$475,000 |
Airbnb cash on cash: -1.34%
|
160 JAMES COURTOldsmar, FLOne or more photo(s) has been virtually staged. Fantastic Price - Welcome to this beautifu... |
3 beds | 2 baths | 1,445 sq.ft. |
$350,000 |
Airbnb cash on cash: -1.56%
|
1204 FORESTWOOD DRIVEOldsmar, FLPicture yourself at 1204 Forestwood Dr, a residence recently refreshed with fresh interior... |
3 beds | 2 baths | 1,186 sq.ft. |
$315,000 |
Airbnb cash on cash: 0.97%
|
9009 PALM KEY AVENUEOldsmar, FLSearching for a low-maintenance waterfront escape in Tampa Bay? Whether youâre looking f... |
4 beds | 3 baths | 2,587 sq.ft. |
$654,900 |
Airbnb cash on cash: -0.94%
|
382 FOUNTAINVIEW CIRCLEOldsmar, FLUnder contract-accepting backup offers. Price Adjustment! Welcome home to this stunning, ... |
4 beds | 2 baths | 1,875 sq.ft. |
$509,000 |
Airbnb cash on cash: 0.51%
|
124 LOBLOLLY COURT #HOldsmar, FLInvestor-friendly opportunity: This turn-key property currently has a cash flowing year-lo... |
2 beds | 2 baths | 915 sq.ft. |
$157,000 |
Airbnb cash on cash: -1.63%
|
634 TIMBER BAY CIRCLE WOldsmar, FLUnder contract-accepting backup offers. Motivated Seller! Move-In Ready Oldsmar Home! Welc... |
3 beds | 2 baths | 1,056 sq.ft. |
$321,500 |
Airbnb cash on cash: 0.56%
|
137 BRENT CIRCLEOldsmar, FLSet within a gated, waterfront community in Oldsmar, this expansive townhouse at 137 Brent... |
3 beds | 2 baths | 2,309 sq.ft. |
$774,900 |
Airbnb cash on cash: -1.2%
|
291 COUNTRYSIDE KEY BOULEVARDOldsmar, FLWelcome to the highly sought-after gated community of Countryside Key, ideally located in ... |
2 beds | 3 baths | 1,110 sq.ft. |
$225,000 |
Airbnb cash on cash: -0.2%
|
2013 SUNSET WIND LOOPOldsmar, FLWelcome to this beautifully maintained 3-bedroom, 2.5-bath townhome in the heart of Oldsma... |
3 beds | 3 baths | 1,667 sq.ft. |
$400,000 |
Airbnb cash on cash: -1.64%
|
108 BRENT CIRCLEOldsmar, FLWelcome to coastal lifestyle living in one of Oldsmarâs most desirable gated waterfront ... |
3 beds | 3 baths | 1,834 sq.ft. |
$389,000 |
Airbnb cash on cash: -1.38%
|
130 WOODLAKE WYNDE #130Oldsmar, FLOne or more photo(s) has been virtually staged. Must See!! Beautifully renovated 2-bedroom... |
2 beds | 2 baths | 924 sq.ft. |
$198,500 |
Airbnb cash on cash: -1.39%
|
207 CYPRESS LANEOldsmar, FLFirst-floor 2-bedroom, 2-bathroom condo located in the East Lake Woodlands community in Ol... |
2 beds | 2 baths | 1,054 sq.ft. |
$180,000 |
Airbnb cash on cash: 2.72%
|
368 TAVERNIER CIRCLEOldsmar, FLBRAND NEW AIR CONDITIONER! GRADE A SCHOOL DISTRICT! COMPLETELY REMODELLED. WELL APPOINTED.... |
4 beds | 2 baths | 1,880 sq.ft. |
$585,000 |
Airbnb cash on cash: 0%
|
5163 PINNACLE DRIVEOldsmar, FLOffering over $23,000 in upgrades! Located in X Flood Zone with no flood insurance require... |
3 beds | 2 baths | 1,886 sq.ft. |
$635,000 |
Airbnb cash on cash: -1.66%
|
219 PALMETTO COURTOldsmar, FLTucked into the peaceful, gated community of East Lake Woodlands, this ground-floor corner... |
2 beds | 2 baths | 1,054 sq.ft. |
$182,000 |
Airbnb cash on cash: 2.22%
|
129 BRENT CIRCLEOldsmar, FLHUGE PRICE IMPROVEMENT of $60k- WATERVIEWS from All 3 Floors, This UPDATED 3Bed 3Bath town... |
3 beds | 3 baths | 1,834 sq.ft. |
$499,000 |
Airbnb cash on cash: -0.78%
|
Real Estate investment in Oldsmar, FL
There are 167 properties for sale in the city of Oldsmar . The median list price in Oldsmar is $426,780 and the average price per square foot is $253. In June 2026, the average monthly cash on cash return in Oldsmar is 4.00%. The average monthly rental income in Oldsmar is $2,371.