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 107 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 |
|---|---|---|---|
1408 CHAPMAN CIRCLEWinter Park, FLNestled in the Elizabethâs Walk subdivision in the highly desirable Windsong community o... |
4 beds | 4 baths | 3,237 sq.ft. |
$1,525,000 |
Airbnb cash on cash: 1.02%
|
740 BAFFIE AVENUEWinter Park, FLWelcome to this fully remodeled, move in ready home perfectly situated on a spacious corne... |
3 beds | 2 baths | 1,456 sq.ft. |
$420,000 |
Airbnb cash on cash: 6.22%
|
1018 TURNER ROADWinter Park, FLSeller may consider buyer concessions if made in an offer | Lakefront charm meets quiet lu... |
3 beds | 2 baths | 2,237 sq.ft. |
$835,000 |
Airbnb cash on cash: 2.27%
|
2607 Lafayette AveWinter Park, FLWelcome to 2607 Lafayette Avenueâa stunning custom home in one of Winter Parkâs most d... |
4 beds | 4 baths | 2,770 sq.ft. |
$1,095,000 |
Airbnb cash on cash: 2.17%
|
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%
|
2550 VENETIAN WAYWinter Park, FL"The richness of an artist is the fusion of influences that have shaped his life and work"... |
4 beds | 5 baths | 4,875 sq.ft. |
$2,499,000 |
Airbnb cash on cash: 0.3%
|
720 N PENNSYLVANIA AVENUEWinter Park, FLNestled in one of Winter Parkâs most sought-after locations, this 3-bedroom, 2-bathroom ... |
3 beds | 2 baths | 1,115 sq.ft. |
$550,000 |
Airbnb cash on cash: 4.56%
|
1400 S PENNSYLVANIA AVENUEWinter Park, FLLook at this rare opportunity to own a chic and trendy residence in winter park in an incr... |
4 beds | 3 baths | 2,310 sq.ft. |
$1,250,000 |
Airbnb cash on cash: 1.79%
|
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%
|
2811 EASTERN PARKWAYWinter Park, FLMid-Century Modern architecture meets modern comfort in this beautifully updated Winter Pa... |
3 beds | 2 baths | 1,433 sq.ft. |
$665,000 |
Airbnb cash on cash: 3.53%
|
1600 PALMER AVENUEWinter Park, FLDiscover refined elegance in this meticulously updated 3-bedroom, 2.5-bath two-story resid... |
3 beds | 3 baths | 2,550 sq.ft. |
$1,200,000 |
Airbnb cash on cash: 1.24%
|
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%
|
720 W WEBSTER AVENUEWinter Park, FLDiscover the charm of Winter Park living in this beautifully maintained 1950s home, where ... |
3 beds | 2 baths | 1,356 sq.ft. |
$575,000 |
Airbnb cash on cash: 4.32%
|
875 W LYMAN AVENUEWinter Park, FLDon't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 ... |
2 beds | 2 baths | 760 sq.ft. |
$475,000 |
Airbnb cash on cash: 3.73%
|
250 Cortland AvenueWinter 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%
|
1150 VIA SALERNOWinter Park, FLIn the heart of Winter Parkâs coveted Vias neighborhood, 1150 Via Salerno is a newly com... |
4 beds | 6 baths | 3,850 sq.ft. |
$4,750,000 |
Airbnb cash on cash: -0.19%
|
2412 CHANTILLY AVENUEWinter Park, FLStep into a world of modern elegance in this newly completed estate in the heart of Winter... |
5 beds | 7 baths | 4,506 sq.ft. |
$2,350,000 |
Airbnb cash on cash: N/A
|
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. |
$1,199,900 |
Airbnb cash on cash: 2.74%
|
1885 TEMPLE DRIVEWinter Park, FLUpdate! ALL NEW Black Steel doors installed 11/2025 and windows with low e-dual pane glass... |
5 beds | 4 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%
|
1399 ALOMA AVENUEWinter Park, FL***Price Adjustment *** Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is ... |
3 beds | 2 baths | 1,804 sq.ft. |
$665,000 |
Airbnb cash on cash: 4.06%
|
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
|
1400 ALABAMA DRIVEWinter Park, FLExtraordinary Waterfront Neoclassical Italian Estate situated on a prime .71-acre corner l... |
5 beds | 9 baths | 7,916 sq.ft. |
$5,895,000 |
Airbnb cash on cash: N/A
|
446 ALBERTA DRIVEWinter Park, FLCharming Opportunity in Prime Winter Park â 446 Alberta Drive, Winter Park, FL! First t... |
4 beds | 3 baths | 3,263 sq.ft. |
$1,750,000 |
Airbnb cash on cash: 1.39%
|
617 WORTHINGTON DRIVEWinter Park, FLWINTER PARK FIVE BEDROOM POOL HOME - Discover luxurious living in the heart of Winter Park... |
5 beds | 5 baths | 3,533 sq.ft. |
$1,770,000 |
Airbnb cash on cash: N/A
|
2211 Azalea PlWinter Park, FLLuxurious waterfront estate in one of Winter Parkâs most prestigious neighborhoods, offe... |
5 beds | 7 baths | 7,278 sq.ft. |
$5,495,000 |
Airbnb cash on cash: N/A
|
473 FLETCHER PLACEWinter Park, FLWelcome to the best of Winter Park living, where luxury meets lifestyle and every day feel... |
5 beds | 6 baths | 4,296 sq.ft. |
$3,250,000 |
Airbnb cash on cash: N/A
|
Lot #21 KAROLINA AVEWinter Park, FLPre-Construction. To be built. Step into a life where charm meets convenience in the heart... |
4 beds | 4 baths | 2,662 sq.ft. |
$916,050 |
Airbnb cash on cash: 4.04%
|
1161 VALENCIA AVENUEWinter Park, FLConveniently situated near the Winter Park Country Club, this contemporary masterpiece, bu... |
4 beds | 5 baths | 4,181 sq.ft. |
$4,545,000 |
Airbnb cash on cash: -0.59%
|
2001 LAKE DRIVEWinter Park, FLNestled on a quiet cul-de-sac in the heart of Winter Park, this canal-front residence offe... |
5 beds | 4 baths | 4,798 sq.ft. |
$2,165,000 |
Airbnb cash on cash: N/A
|
1007 EARLY AVENUEWinter Park, FLWelcome to your next chapter at 1007 Early Ave in Winter Park, a charming 3-bedroom, 2-bat... |
3 beds | 2 baths | 1,721 sq.ft. |
$425,000 |
Airbnb cash on cash: 7.09%
|
607 ELLEN DRIVEWinter Park, FLDiscover sophisticated modern living at 607 Ellen Drive, a stunning new construction home ... |
4 beds | 5 baths | 2,812 sq.ft. |
$1,630,000 |
Airbnb cash on cash: 1.66%
|
3018 NORTHWOOD BOULEVARDWinter Park, FLOne or more photo(s) has been virtually staged. "MOVE-IN READY", 3-BED, 2-FULL BATHS, SING... |
3 beds | 2 baths | 1,761 sq.ft. |
$733,000 |
Airbnb cash on cash: 2.98%
|
516 HENKEL CIRCLEWinter Park, FLThis beautiful Mediterranean style home offers a rare opportunity for prime waterfront liv... |
5 beds | 6 baths | 4,143 sq.ft. |
$3,499,000 |
Airbnb cash on cash: N/A
|
1451 Cavendish RoadWinter 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%
|
1205 MAYFIELD AVENUEWinter Park, FLOne or more photo(s) has been virtually staged. This beautiful two-story residence is loca... |
5 beds | 4 baths | 3,948 sq.ft. |
$2,350,000 |
Airbnb cash on cash: N/A
|
560 OLOLU DRIVEWinter 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 AVENUEWinter 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%
|
2503 VERSAILLES AVENUEWinter Park, FLBeautifully updated and offered for the first time, this 2015 David Weekley home sits on a... |
5 beds | 5 baths | 4,026 sq.ft. |
$2,775,000 |
Airbnb cash on cash: N/A
|
2361 MULBRY DRIVEWinter 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%
|