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. |
$1,599,000 |
Airbnb cash on cash: 0.01%
|
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. |
$445,000 |
Airbnb cash on cash: 5.82%
|
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%
|
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. |
$355,000 |
Airbnb cash on cash: 4.66%
|
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. |
$575,000 |
Airbnb cash on cash: 4.32%
|
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. |
$2,935,000 |
Airbnb cash on cash: 0.5%
|
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. |
$900,000 |
Airbnb cash on cash: 2.26%
|
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. |
$815,000 |
Airbnb cash on cash: 3.57%
|
1229 PARK GREEN PLACEWinter Park, FLThis 2 bedroom, 2 bathroom townhome offers 1,495 square feet of beautifully designed space... |
2 beds | 2 baths | 1,495 sq.ft. |
$395,000 |
Airbnb cash on cash: 3.74%
|
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%
|
520 KILLARNEY BAY COURT #2Winter Park, FLPRICED TO SELL! Nestled in the heart of Winter Park, this updated 2 bedroom, 2 bath second... |
2 beds | 2 baths | 1,160 sq.ft. |
$339,000 |
Airbnb cash on cash: 5.39%
|
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. |
$590,000 |
Airbnb cash on cash: 3.15%
|
2722 EASTERN PARKWAYWinter Park, FLUnder Construction. Masterfully designed new construction by LUIH Luxury Homes, where arch... |
5 beds | 5 baths | 3,334 sq.ft. |
$2,289,000 |
Airbnb cash on cash: N/A
|
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
|
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. |
$1,199,900 |
Airbnb cash on cash: 2.74%
|
1751 GLENCOE ROADWinter Park, FLNestled just moments from the boutiques and cafés on Park Avenue, this newly completed Da... |
5 beds | 7 baths | 4,520 sq.ft. |
$3,895,000 |
Airbnb cash on cash: N/A
|
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
|
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%
|
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%
|
1360 FORMOSA AVENUEWinter Park, FLDiscover a rare and lucrative opportunity at 1360 Formosa Ave, a corner lot triplex in the... |
3 beds | N/A baths | 1,890 sq.ft. |
$625,000 |
Airbnb cash on cash: 3.39%
|
101 S INTERLACHEN AVENUE #104Winter Park, FLFIRST TIME ON THE MARKET! SUPER RARE, GROUND FLOOR, DOWNTOWN WINTER PARK CONDO AT LACHEN H... |
2 beds | 2 baths | 949 sq.ft. |
$649,000 |
Airbnb cash on cash: 2.35%
|
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%
|
1560 WOODLAND AVENUEWinter Park, FLYou have arrived to 1560 Woodland Avenue, a beautiful home in a prime location inside the ... |
5 beds | 5 baths | 3,851 sq.ft. |
$1,999,000 |
Airbnb cash on cash: N/A
|
2500 LEE ROAD #208Winter Park, FLThis charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfor... |
2 beds | 2 baths | 956 sq.ft. |
$200,000 |
Airbnb cash on cash: 8.82%
|
1910 GLENCOE ROADWinter Park, FLUnder Construction. Stunning architectural masterpiece built by LUIH homes nestled in the ... |
4 beds | 6 baths | 4,205 sq.ft. |
$3,490,000 |
Airbnb cash on cash: 0.21%
|
Real Estate investment in Winter-park, FL
There are 173 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 December 2025, the average monthly cash on cash return in Winter Park is 2.00%. The average monthly rental income in Winter Park is $2,192.