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 |
|---|---|---|---|
5250 PINEHURST CourtOldsmar, FLRARELY AVAILABLE VILLA OPPORTUNITY IN PRIVATE PINNACLE COMMUNITY OF EAST LAKE WOODLANDS. "... |
3 beds | 2 baths | 2,074 sq.ft. |
$640,000 |
Airbnb cash on cash: 0.43%
|
110 CYPRESS CT #3-82Oldsmar, FLWelcome to a condo that feels like home the moment you step inside. Beautifully updated an... |
2 beds | 2 baths | 1,054 sq.ft. |
$190,000 |
Airbnb cash on cash: 6.8%
|
601 SHORE Drive EOldsmar, FLWelcome to this beautifully updated 3-bedroom, 2-bathroom home in the heart of Oldsmar, of... |
3 beds | 2 baths | 1,856 sq.ft. |
$525,000 |
Airbnb cash on cash: 1.82%
|
3858 SHORE BoulevardOldsmar, FLExperience the laid back lifestyle of Oldsmar, a sought-after community nestled between th... |
3 beds | 2 baths | 1,594 sq.ft. |
$1,100,000 |
Airbnb cash on cash: -0.02%
|
360 S WOODLANDS DriveOldsmar, FLWelcome to 360 S Woodlands Drive, a beautifully renovated 2-bedroom, 2-bath patio home nes... |
2 beds | 2 baths | 1,590 sq.ft. |
$399,900 |
Airbnb cash on cash: 1.2%
|
1705 IRONWOOD Court EOldsmar, FLWelcome to this beautifully renovated 2-bedroom, 2-bathroom home-perfect for first-time bu... |
2 beds | 2 baths | 1,206 sq.ft. |
$320,000 |
Airbnb cash on cash: 4.15%
|
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: 8.22%
|
1103 MANGO CourtOldsmar, FLWelcome to refined coastal living in this beautifully appointed 3-bedroom, 2.5-bath townho... |
3 beds | 3 baths | 2,230 sq.ft. |
$489,000 |
Airbnb cash on cash: 0.39%
|
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: 3.82%
|
279 COUNTRYSIDE KEY BoulevardOldsmar, FLVirtually Staged. Welcome home to this beautiful END UNIT & FULLY UPDATED 2BR/1.5BA townho... |
2 beds | 2 baths | 1,105 sq.ft. |
$275,000 |
Airbnb cash on cash: 2.95%
|
150 POOLE PlaceOldsmar, FLWelcome to 150 Poole Place, a spacious 4-bedroom, 2-bath villa offering approximately 1,55... |
4 beds | 2 baths | 1,550 sq.ft. |
$385,000 |
Airbnb cash on cash: 2.42%
|
416 MAPLEWOOD DriveOldsmar, FL**PRICE IMPROVEMENT** Your opportunity just got better.! This beautiful home is now offere... |
3 beds | 2 baths | 1,395 sq.ft. |
$449,000 |
Airbnb cash on cash: 3.02%
|
123 LOBLOLLY Court #BOldsmar, FLVirtually Staged. GROUND FLOOR ~ NON - FLOOD ZONE. 2 Bedrooms, 2 Bathroom and move in read... |
2 beds | 2 baths | 915 sq.ft. |
$115,000 |
Airbnb cash on cash: 5.53%
|
2013 SUNSET WIND LoopOldsmar, FLDiscover modern comfort and effortless living in this beautifully maintained 3-bedroom, 2.... |
3 beds | 3 baths | 1,667 sq.ft. |
$400,000 |
Airbnb cash on cash: 0.9%
|
108 BRENT CircleOldsmar, FLWelcome to coastal lifestyle living in one of Oldsmar's most desirable gated waterfront co... |
3 beds | 3 baths | 1,834 sq.ft. |
$384,000 |
Airbnb cash on cash: 1.26%
|
100 LISA LaneOldsmar, FLPrevious contract fell through due to financing. Owner is motivated. The property has a cl... |
2 beds | 2 baths | 1,320 sq.ft. |
$299,000 |
Airbnb cash on cash: 3.3%
|
1745 OAK POND CourtOldsmar, FLWelcome to 1745 Oak Pond Court! Welcome to 1745 Oak Pond Court, a beautiful home located i... |
4 beds | 3 baths | 2,324 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.55%
|
10 ARBOR LaneOldsmar, FLBeautiful 4-bedroom, 2-bathroom pool home on a corner lot with views of the 5th hole in Ea... |
4 beds | 2 baths | 2,318 sq.ft. |
$669,000 |
Airbnb cash on cash: 1%
|
2410 ARCH AvenueOldsmar, FLImagine coming home to breathtaking waterfront surroundings, resort-style amenities, and m... |
3 beds | 3 baths | 1,888 sq.ft. |
$429,500 |
Airbnb cash on cash: 1.26%
|
550 PALMDALE DriveOldsmar, FLA True Find for exceptional living in the highly desirable Gated Golf Community of East La... |
4 beds | 2 baths | 2,211 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.62%
|
1723 CAPTIVA DriveOldsmar, FLVirtually Staged. Welcome to an exceptional 2,736-square-foot luxury home nestled within C... |
4 beds | 3 baths | 2,736 sq.ft. |
$830,700 |
Airbnb cash on cash: 1.58%
|
206 BEDFORD StreetOldsmar, FLVirtually Staged. Short Sale. BANKRUPTCY PROPERTY - AND THE PRICE IS PRE-APPROVED! This be... |
3 beds | 2 baths | 1,274 sq.ft. |
$355,700 |
Airbnb cash on cash: 3.4%
|
204 WINDWARD Place #36Oldsmar, FLWelcome to 204 Windward Place #36, a move-in-ready condominium located in the gated commun... |
2 beds | 2 baths | 879 sq.ft. |
$188,000 |
Airbnb cash on cash: 4.17%
|
415 MAPLEWOOD CircleOldsmar, FLA beautifully maintained home in the desirable Sheffield Village area of Oldsmar, this pro... |
3 beds | 1 baths | 1,583 sq.ft. |
$349,900 |
Airbnb cash on cash: 3.17%
|
208 CLAYS Trail #208Oldsmar, FLBeautifully updated condo in East Lake Woodlands with 3 bedrooms, 2 full baths, 1 car gara... |
3 beds | 2 baths | 1,835 sq.ft. |
$399,000 |
Airbnb cash on cash: 2.98%
|
347 COUNTRY CLUB DriveOldsmar, FL"Move-In Ready"... Freshly Painted and Beautifully completely Refurbished Single Family Po... |
3 beds | 2 baths | 1,280 sq.ft. |
$419,000 |
Airbnb cash on cash: 3.28%
|
Real Estate investment in Oldsmar, FL
There are 132 properties for sale in the city of Oldsmar . The median list price in Oldsmar is $402,234 and the average price per square foot is $246. In October 2026, the average monthly cash on cash return in Oldsmar is 4.00%. The average monthly rental income in Oldsmar is $2,192.