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.
Investment Property for Sale in Winter Park, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
1270 ARLINGTON PLACEWinter Park, FLModern Elegance in the Heart of Winter Park! Located just a half-mile from the renowned... |
3 beds | 4 baths | 2,964 sq.ft. |
$1,649,000 |
Airbnb cash on cash: -0.02%
|
1781 PINE AVENUEWinter Park, FLPrice Reduced to sell. An exceptional custom home by award-winning Davila Homes, perfectly... |
5 beds | 5 baths | 3,882 sq.ft. |
$2,279,000 |
Airbnb cash on cash: N/A
|
715 VIA BELLAWinter Park, FLTucked away on a quiet cul-de-sac lined with multi-million-dollar estates, this Winter Par... |
5 beds | 4 baths | 4,328 sq.ft. |
$2,269,000 |
Airbnb cash on cash: N/A
|
1661 HILLCREST AVENUEWinter Park, FLThis property is also listed for Rent with MLS#O6337514. Luxurious Winter Park Retreat wit... |
4 beds | 4 baths | 3,161 sq.ft. |
$1,949,999 |
Airbnb cash on cash: 0.68%
|
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. |
$850,000 |
Airbnb cash on cash: 2.22%
|
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%
|
1516 PINEWOOD DRIVEWinter Park, FLPINEWOOD SUB N/9 LOT 12 BLK A Well-maintained, modest 2-1 home in College Park with c... |
2 beds | 1 baths | 1,028 sq.ft. |
$349,000 |
Airbnb cash on cash: 5.04%
|
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. |
$2,599,000 |
Airbnb cash on cash: 0.25%
|
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%
|
1760 VIA VENETIAWinter Park, FLDiscover unparalleled luxury in this meticulously crafted estate home, where no detail has... |
4 beds | 7 baths | 6,242 sq.ft. |
$4,995,000 |
Airbnb cash on cash: -0.6%
|
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. |
$1,290,000 |
Airbnb cash on cash: 1.7%
|
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. |
$950,000 |
Airbnb cash on cash: 3.18%
|
150 KILLARNEY BAY COURT #5Winter Park, FLTucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfec... |
2 beds | 2 baths | 1,140 sq.ft. |
$362,500 |
Airbnb cash on cash: 4.55%
|
1350 LYNDALE BOULEVARDWinter Park, FLTHIS HOUSE CHECKS ALL OF THE BOXES!!! Situated on a quiet one-way street in Winter Park a... |
4 beds | 5 baths | 3,478 sq.ft. |
$1,590,000 |
Airbnb cash on cash: 0.97%
|
1521 CHESTNUT AVENUEWinter Park, FLModern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, buil... |
4 beds | 3 baths | 2,843 sq.ft. |
$1,899,900 |
Airbnb cash on cash: 0.48%
|
700 MELROSE AVENUE #D21Winter Park, FLLocated in the historic Winter Park Gardens community, this condo has been meticulously ma... |
1 beds | 1 baths | 871 sq.ft. |
$198,800 |
Airbnb cash on cash: 6.51%
|
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. |
$625,000 |
Airbnb cash on cash: 3.9%
|
541 W CANTON AVENUEWinter Park, FLTimeless elegance meets boutique craftsmanship at 541 W Canton Avenueâan exceptional new... |
4 beds | 4 baths | 3,553 sq.ft. |
$3,150,000 |
Airbnb cash on cash: 0.4%
|
915 GARDEN DRIVEWinter Park, FLStunning Mid-Century Modern Home in Prime Winter Park Location â Solar Powered, Pool, No... |
3 beds | 3 baths | 2,456 sq.ft. |
$940,000 |
Airbnb cash on cash: 2.12%
|
151 N ORLANDO AVENUE #212Winter Park, FLExperience luxury lakefront living in this stunning and truly unique 3-bedroom, 2-bathroom... |
3 beds | 2 baths | 1,875 sq.ft. |
$575,000 |
Airbnb cash on cash: 2.47%
|
311 E MORSE BOULEVARD #7-2Winter Park, FLOne or more photo(s) has been virtually staged. Enjoy sunrise views over Lake Osceola from... |
1 beds | 1 baths | 900 sq.ft. |
$399,000 |
Airbnb cash on cash: 0.42%
|
675 OVERSPIN DRIVEWinter Park, FLSeller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatil... |
4 beds | 4 baths | 3,062 sq.ft. |
$829,000 |
Airbnb cash on cash: 3.5%
|
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%
|
1391 RICHMOND ROADWinter Park, FLWelcome to 1391 Richmond Road, a true work of art and a surreal living experience now on t... |
4 beds | 6 baths | 4,635 sq.ft. |
$3,325,000 |
Airbnb cash on cash: 0.08%
|
1250 FORMOSA AVENUEWinter Park, FLModern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nest... |
3 beds | 4 baths | 1,937 sq.ft. |
$599,500 |
Airbnb cash on cash: 3.08%
|
535 N INTERLACHEN AVENUE #106Winter Park, FLCombining luxury living with exceptional value, this immaculate, move-in-ready condo is ju... |
2 beds | 2 baths | 1,000 sq.ft. |
$599,900 |
Airbnb cash on cash: 2.97%
|
3601 MIDIRON DRIVEWinter Park, FLBUILD YOUR DREAM HOME IN WINTER PARK! Nestled directly across from the historic Dubsdread... |
2 beds | 1 baths | 954 sq.ft. |
$459,000 |
Airbnb cash on cash: 3.36%
|
151 N ORLANDO AVENUE #118Winter Park, FLInvestment opportunity! Discover this hidden gemâa 2-bed, 1-bath condo nestled in the he... |
2 beds | 1 baths | 710 sq.ft. |
$299,999 |
Airbnb cash on cash: 6.61%
|
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. |
$1,260,000 |
Airbnb cash on cash: 2.56%
|
920 GLORIOSA AVENUEWinter Park, FLCharming Move-In Ready Home in the Heart of Winter Park! Discover this beautifully main... |
3 beds | 2 baths | 1,540 sq.ft. |
$409,988 |
Airbnb cash on cash: 7.29%
|
2128 SYCAMORE DRIVEWinter Park, FLMUST SEE! RENOVATED, MOVE-IN READY! Donât miss this fantastic opportunity to own a beau... |
3 beds | 2 baths | 1,760 sq.ft. |
$825,000 |
Airbnb cash on cash: 2.72%
|
1885 TEMPLE DRIVEWinter Park, FLUpdate! ALL NEW Black Steel doors and windows with low e-dual pane glass will be installed... |
5 beds | 4 baths | 3,691 sq.ft. |
$2,350,000 |
Airbnb cash on cash: N/A
|
2500 LEE ROAD #243Winter Park, FLReasons you'll love this condo: convenient, cozy and quiet, you can't beat this community ... |
1 beds | 1 baths | 645 sq.ft. |
$200,000 |
Airbnb cash on cash: 5.71%
|
2260 MULBRY DRIVEWinter Park, FLPre-Construction. To be built. Price Improvement!!! Your Dream Home Is Ready To Be Built!!... |
5 beds | 4 baths | 3,246 sq.ft. |
$1,800,000 |
Airbnb cash on cash: N/A
|
1875 STAUNTON AVENUEWinter Park, FLWelcome to this newer single-family home tucked away in the Karolina On Killarney section ... |
4 beds | 2 baths | 2,036 sq.ft. |
$560,000 |
Airbnb cash on cash: 6.18%
|
1660 WALNUT AVENUEWinter Park, FLUnder Construction. Elegant and modern new construction home perfectly situated in beautif... |
4 beds | 4 baths | 2,172 sq.ft. |
$1,759,000 |
Airbnb cash on cash: 1.35%
|
785 N PHELPS AVENUEWinter Park, FLUnder Construction. Completion December 2025, Nestled in the heart of Winter Park, this lu... |
5 beds | 4 baths | 2,964 sq.ft. |
$2,119,000 |
Airbnb cash on cash: N/A
|
726 And 720 N PENNSYLVANIA AVENUEWinter Park, FLWelcome to this exceptional duplex, a rare gem in Winter Park offering unmatched flexibili... |
6 beds | N/A baths | 2,284 sq.ft. |
$1,215,000 |
Airbnb cash on cash: 0.33%
|
Real Estate investment in Winter-park, FL
There are 213 properties for sale in the city of Winter Park . The median list price in Winter Park is $550,000 and the average price per square foot is $261. In October 2025, the average monthly cash on cash return in Winter Park is 2.00%. The average monthly rental income in Winter Park is $2,323.