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 |
|---|---|---|---|
505 OAKWOOD BOULEVARDOldsmar, FLWelcome to this CHARMING HOME tucked away on a quiet, divided street in BEAUTIFUL DOWNTOWN... |
4 beds | 2 baths | 1,993 sq.ft. |
$449,000 |
Airbnb cash on cash: 6.48%
|
110 CYPRESS COURT #3-82Oldsmar, FLWelcome to a condo that instantly feels like home the moment you walk in, beautifully upda... |
2 beds | 2 baths | 1,054 sq.ft. |
$175,000 |
Airbnb cash on cash: 7.72%
|
1203 CLAYS TRAIL #406Oldsmar, FLMotivated sellers and are offering the new owners a credit to cover the monthly condo fees... |
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. |
$700,000 |
Airbnb cash on cash: 2.87%
|
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: 7.01%
|
204 BAY ARBOR BOULEVARDOldsmar, FLUnder contract-accepting backup offers. Welcome to your beautifully upgraded 3 bed / 2 bat... |
3 beds | 2 baths | 2,026 sq.ft. |
$639,900 |
Airbnb cash on cash: 1.73%
|
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. |
$849,990 |
Airbnb cash on cash: 2.37%
|
1909 CASTLE BAY COURTOldsmar, FL--WONT LAST LONG---Discover this immaculate 3-bedroom, 2-bath home with garage located on ... |
3 beds | 2 baths | 1,410 sq.ft. |
$394,000 |
Airbnb cash on cash: 5.06%
|
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. |
$169,000 |
Airbnb cash on cash: 7.88%
|
396 COUNTRYSIDE KEY BOULEVARDOldsmar, FLOffers 1% lender credit at closing. Welcome to this beautifully updated 2-bedroom, 2.5-bat... |
2 beds | 3 baths | 1,110 sq.ft. |
$280,000 |
Airbnb cash on cash: 4.8%
|
1471 BRIARGROVE WAYOldsmar, FLOne or more photo(s) has been virtually staged. Live the Florida lifestyle in the gated Ab... |
5 beds | 4 baths | 3,140 sq.ft. |
$945,000 |
Airbnb cash on cash: N/A
|
128 CAMPHOR CIRCLE #COldsmar, FLUnder contract-accepting backup offers. Welcome home to this beautifully updated 2-bedroom... |
2 beds | 2 baths | 915 sq.ft. |
$154,900 |
Airbnb cash on cash: 9.16%
|
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%
|
315 WOODS LANDING TRAILOldsmar, FLCompletely updated, water view townhome within the 24hr guard gated, golf cart friendly, c... |
2 beds | 3 baths | 1,200 sq.ft. |
$319,900 |
Airbnb cash on cash: 1.23%
|
210 MARTHA LANE #210Oldsmar, FLUnder contract-accepting backup offers. Welcome to this charming 2-bedroom, 2-bathroom con... |
2 beds | 2 baths | 1,094 sq.ft. |
$169,900 |
Airbnb cash on cash: 6.18%
|
124 NINA WAY #24Oldsmar, FLWelcome Home! This renovated condo is simply beautiful! Located in the premier golf comm... |
2 beds | 2 baths | 1,094 sq.ft. |
$209,900 |
Airbnb cash on cash: 3.7%
|
646 TIMBER BAY CIRCLE WOldsmar, FLPRICE IMPROVEMENT - LOCATION - LOCATION - LOCATION - LOVE WHERE YOU LIVE - ONE STORY POOL ... |
3 beds | 2 baths | 1,554 sq.ft. |
$409,000 |
Airbnb cash on cash: 4.4%
|
421 SHORE DRIVE EOldsmar, FLUnder contract-accepting backup offers. Prime investment opportunity in one of Oldsmarâs... |
3 beds | 2 baths | 1,416 sq.ft. |
$285,000 |
Airbnb cash on cash: 6.96%
|
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: 1.94%
|
648 TIMBER BAY CIRCLE EOldsmar, FLDiscover your own slice of paradise with this beautifully updated 4-bedroom, 2-bath home, ... |
4 beds | 2 baths | 1,253 sq.ft. |
$379,000 |
Airbnb cash on cash: 7.64%
|
4954 TURTLE CREEK TRAILOldsmar, FLWelcome to this exceptional Costanza custom-built home, perfectly situated on over one acr... |
5 beds | 4 baths | 4,144 sq.ft. |
$1,425,000 |
Airbnb cash on cash: N/A
|
150 POOLE PLACEOldsmar, FLFrom the moment you arrive at this East Lake Woodlands villa, it feels like youâve stepp... |
4 beds | 2 baths | 1,550 sq.ft. |
$337,500 |
Airbnb cash on cash: 8.13%
|
350 HOLLY HILL ROADOldsmar, FLUnder contract-accepting backup offers. *UNDER CONTRACT ACCEPTING BACK UP OFFERS*Welcome t... |
4 beds | 2 baths | 2,510 sq.ft. |
$669,000 |
Airbnb cash on cash: 3.56%
|
367 COUNTRYSIDE KEY BOULEVARDOldsmar, FLUnder contract-accepting backup offers. Beautifully updated 2BR/1.5BA townhouse in the des... |
2 beds | 2 baths | 1,105 sq.ft. |
$245,000 |
Airbnb cash on cash: 3.79%
|
40 GRETCHEN COURTOldsmar, FLSELLER FINANCING WITH ACCEPTABLE OFFER! Step through the front door of this charming vill... |
2 beds | 2 baths | 1,502 sq.ft. |
$338,000 |
Airbnb cash on cash: 2.28%
|
316 LAFAYETTE BOULEVARDOldsmar, FLUnder contract-accepting backup offers. Live the ultimate Florida lifestyle in this specta... |
4 beds | 4 baths | 2,848 sq.ft. |
$640,000 |
Airbnb cash on cash: 3.78%
|
100 INGRID PLACEOldsmar, FLGreat opportunity to own this Lovely Updated 3 Bed, 2.5 Bath East Lake Woodlands Townhouse... |
3 beds | 3 baths | 1,755 sq.ft. |
$299,000 |
Airbnb cash on cash: 4.87%
|
5163 PINNACLE DRIVEOldsmar, FLWelcome to 5163 Pinnacle Drive, a beautifully maintained home in the highly sought-after g... |
3 beds | 2 baths | 1,886 sq.ft. |
$619,700 |
Airbnb cash on cash: 1.09%
|
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. |
$365,000 |
Airbnb cash on cash: 4.31%
|
1608 SUNSET WIND LOOPOldsmar, FLUnder contract-accepting backup offers. **This home has over $90,000 in upgrades and has 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%
|
504 FEDERAL STREETOldsmar, FLUnder Construction. Experience the perfect blend of modern luxury, thoughtful design, and ... |
4 beds | 4 baths | 2,961 sq.ft. |
$1,200,000 |
Airbnb cash on cash: 2.04%
|
403 PARK BOULEVARDOldsmar, FLOne or more photo(s) has been virtually staged. Welcome to 403 Park Blvd, a brand-new 2025... |
4 beds | 4 baths | 2,900 sq.ft. |
$899,000 |
Airbnb cash on cash: 2.97%
|
347 COUNTRY CLUB DRIVEOldsmar, FL"Move-In Ready"... Beautifully and Completely Refurbished Single Family Pool Home, (3) Bed... |
3 beds | 2 baths | 1,280 sq.ft. |
$449,000 |
Airbnb cash on cash: 4.59%
|
316 SHORE DRIVE EOldsmar, FLWake up to million-dollar views, and unwind with spectacular sunsets - this is the waterfr... |
4 beds | 3 baths | 2,496 sq.ft. |
$1,500,000 |
Airbnb cash on cash: 0.36%
|
375 WELLINGTON AVENUEOldsmar, FLCOMPLETE LUXURY MAKEOVER! (Back on market after buyer couldn't get financing) Welcome to y... |
4 beds | 3 baths | 3,270 sq.ft. |
$1,325,000 |
Airbnb cash on cash: 1.46%
|
1358 FORESTEDGE BOULEVARDOldsmar, FLUnder contract-accepting backup offers. BACK ON THE MARKET! Exceptional move-in ready home... |
4 beds | 3 baths | 2,808 sq.ft. |
$925,000 |
Airbnb cash on cash: 1.43%
|
380 WELLINGTON AVENUEOldsmar, FLPRICE REDUCTION! Now priced below value, this is your chance to own this incredible Key We... |
4 beds | 4 baths | 3,420 sq.ft. |
$1,155,000 |
Airbnb cash on cash: 1.75%
|
205 BENGAL CIRCLEOldsmar, FLHIGH AND DRY! Elevation certificate available. Backing up to a nature preserve, this 4 bed... |
4 beds | 3 baths | 2,733 sq.ft. |
$799,000 |
Airbnb cash on cash: 2.68%
|
603 SHORE DRIVE EOldsmar, FLThis exceptional 3-bedroom, 2-bathroom pool home, nestled in the heart of Oldsmar and Tamp... |
3 beds | 2 baths | 1,722 sq.ft. |
$485,000 |
Airbnb cash on cash: 3.07%
|
Real Estate investment in Oldsmar, FL
There are 152 properties for sale in the city of Oldsmar . The median list price in Oldsmar is $396,950 and the average price per square foot is $215. In December 2025, the average monthly cash on cash return in Oldsmar is 4.00%. The average monthly rental income in Oldsmar is $2,425.