Real Estate Investment Properties for Sale in Winter Park, FL
Looking for investment property in Winter Park, FL with high ROI ?
Explore a variety of short-term homes & houses in Winter Park, FL. Invest wisely with VRBO & Winter Park, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Single Family Homes for Sale in Winter Park, FL
Search for Single Family Residential for Sale in Winter Park, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.
Showing 245 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
640 Arjay WayWinter Park, FLLocated in one of Winter Parkâs most desirable and picturesque neighborhoods, Timberlane... |
5 beds | 3 baths | 3,860 sq.ft. |
$1,989,000 |
Airbnb cash on cash: N/A
|
1751 Goodrich AveWinter Park, FLWelcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park... |
4 beds | 3 baths | 2,170 sq.ft. |
$1,475,000 |
Airbnb cash on cash: 1.66%
|
1324 INDIANA AVENUEWinter Park, FLCharming two story bungalow built in 1935. Timeless character meets modern comfort in this... |
4 beds | 3 baths | 1,692 sq.ft. |
$745,000 |
Airbnb cash on cash: 4.32%
|
208 BREWER AVENUEWinter Park, FLWelcome to this beautifully updated 4-bedroom, 3.5-bath Craftsman-style home, offering jus... |
4 beds | 4 baths | 2,173 sq.ft. |
$925,000 |
Airbnb cash on cash: 3.29%
|
948 Poinciana LnWinter Park, FLTimeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an ... |
4 beds | 3 baths | 3,676 sq.ft. |
$3,599,000 |
Airbnb cash on cash: -0.2%
|
726 N PENNSYLVANIA AVENUEWinter Park, FLWelcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of moder... |
3 beds | 2 baths | 1,167 sq.ft. |
$695,000 |
Airbnb cash on cash: 3.43%
|
250 Cortland AveWinter Park, FLWelcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among mil... |
3 beds | 2 baths | 2,114 sq.ft. |
$950,000 |
Airbnb cash on cash: 2.31%
|
1981 BLUE RIDGE ROADWinter Park, FLOne or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE thr... |
4 beds | 2 baths | 2,750 sq.ft. |
$1,180,000 |
Airbnb cash on cash: 2.8%
|
1885 Temple DrWinter Park, FLNEW 2026 Black Steel doors windows with low e-dual pane glass ($150k value!). Located in h... |
5 beds | 3 baths | 3,691 sq.ft. |
$2,295,000 |
Airbnb cash on cash: N/A
|
1564 CAVENDISH ROADWinter Park, FLCharming 3BR bungalow in sought-after Orwin Manor with timeless appeal and tons of potenti... |
3 beds | 1 baths | 1,140 sq.ft. |
$450,000 |
Airbnb cash on cash: 5.72%
|
1996 Indiana AveWinter Park, FLInvestor Special â Fixer Upper Opportunity in Winter Park / College Park Area. Rare o... |
2 beds | 1 baths | 818 sq.ft. |
$249,900 |
Airbnb cash on cash: 8.76%
|
1112 PRESERVE POINT DRIVEWinter Park, FLPresenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rar... |
5 beds | 6 baths | 6,502 sq.ft. |
$8,500,000 |
Airbnb cash on cash: N/A
|
446 Alberta DrWinter Park, FLCharming Opportunity in Prime Winter Park â 446 Alberta Drive, Winter Park, FL! First t... |
4 beds | 2 baths | 3,263 sq.ft. |
$1,675,000 |
Airbnb cash on cash: 1.39%
|
2211 Azalea PlWinter Park, FLLuxurious waterfront estate in one of Winter Parkâs most prestigious neighborhoods, offe... |
5 beds | 6 baths | 7,278 sq.ft. |
$5,495,000 |
Airbnb cash on cash: N/A
|
473 Fletcher PlWinter Park, FLWelcome to the best of Winter Park living, where luxury meets lifestyle and every day feel... |
5 beds | 5 baths | 4,296 sq.ft. |
$3,250,000 |
Airbnb cash on cash: N/A
|
1161 Valencia AveWinter Park, FLConveniently situated near the Winter Park Country Club, this contemporary masterpiece, bu... |
4 beds | 4 baths | 4,181 sq.ft. |
$4,345,000 |
Airbnb cash on cash: -0.58%
|
607 Ellen DrWinter Park, FLDiscover sophisticated modern living at 607 Ellen Drive, a stunning new construction home ... |
4 beds | 3 baths | 2,812 sq.ft. |
$1,599,900 |
Airbnb cash on cash: 1.66%
|
2580 Euston Rd #0Winter Park, FLjust over .25 acre in winter park with block construction 3 bedroom 2 bath. Opportunity to... |
3 beds | 2 baths | 1,158 sq.ft. |
$415,000 |
Airbnb cash on cash: 6.37%
|
2009 Cornell AveWinter Park, FL2009 Cornell Ave, Orlando, FL 32789 | Single Family Residential |
2 beds | 1 baths | 762 sq.ft. |
$259,000 |
Airbnb cash on cash: 8.08%
|
516 Henkel CirWinter Park, FLThis beautiful Mediterranean style home offers a rare opportunity for prime waterfront liv... |
5 beds | 6 baths | 4,143 sq.ft. |
$3,350,000 |
Airbnb cash on cash: N/A
|
1451 Cavendish RdWinter Park, FLWelcome to 1451 Cavendish Road, a beautifully renovated home in the heart of Orwin Manor, ... |
3 beds | 2 baths | 1,437 sq.ft. |
$619,500 |
Airbnb cash on cash: 3.7%
|
560 Ololu DrWinter Park, FLNestled on the shores of private, skiable Lake Killarney, this beautifully updated and abs... |
2 beds | 2 baths | 1,086 sq.ft. |
$949,000 |
Airbnb cash on cash: 0.85%
|
1780 Bryan AveWinter Park, FLDiscover a truly unique offering in the heart of Winter Park! This property, located at 17... |
4 beds | 2 baths | 1,617 sq.ft. |
$800,000 |
Airbnb cash on cash: 4.13%
|
2361 Mulbry DrWinter Park, FLUnder Construction. Signature new construction currently under way, thoughtfully designed ... |
4 beds | 4 baths | 3,111 sq.ft. |
$2,395,000 |
Airbnb cash on cash: 0.78%
|
1841 Harland Park DrWinter Park, FLWelcome home to the prestigious community of Windsong in Winter Park. Upon entering this T... |
4 beds | 3 baths | 3,470 sq.ft. |
$1,895,000 |
Airbnb cash on cash: 0.22%
|
1523 Miller AveWinter Park, FLUnder Construction. UNDER CONSTRUCTION. This 3,164 sq ft new construction home at 1523 Mil... |
5 beds | 4 baths | 3,164 sq.ft. |
$1,550,000 |
Airbnb cash on cash: N/A
|