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 |
|---|---|---|---|
345 SYLVAN BOULEVARDWinter Park, FLWelcome to this stunning 4-bedroom, 2.5-bathroom POOL home with a NEW ROOF, offering a per... |
4 beds | 3 baths | 2,011 sq.ft. |
$1,075,000 |
Airbnb cash on cash: 2.4%
|
140 E MORSE BOULEVARD #JWinter Park, FLINTRODUCING THE COVETED CORNER PENTHOUSE UNIT IN ONE OF WINTER PARK'S LUXURY CONDO BUILDIN... |
3 beds | 3 baths | 2,143 sq.ft. |
$2,890,000 |
Airbnb cash on cash: -1.26%
|
1010 N PENNSYLVANIA AVENUEWinter Park, FLLocated in the heart of Winter Park's downtown corridor, 1010 N Pennsylvania Ave offers a ... |
4 beds | 5 baths | 4,074 sq.ft. |
$2,800,000 |
Airbnb cash on cash: 0.73%
|
678 DEPUGH STREETWinter Park, FLThis stunning property in historic Winter Park offers an excellent price point and is idea... |
4 beds | 3 baths | 1,940 sq.ft. |
$700,000 |
Airbnb cash on cash: 4.71%
|
100 S VIRGINIA AVENUE #201Winter Park, FLUnder contract-accepting backup offers. Discover luxury living in this exquisite single-st... |
3 beds | 3 baths | 2,756 sq.ft. |
$1,175,000 |
Airbnb cash on cash: -0.31%
|
648 CALLAHAN STREETWinter Park, FLWelcome to this stunning modern, custom-built home in the heart of Winter Park, FL! This b... |
3 beds | 3 baths | 1,898 sq.ft. |
$899,000 |
Airbnb cash on cash: 2.55%
|
2550 VENETIAN WAYWinter Park, FL"The richness of an artist is the fusion of influences that have shaped his life and work"... |
4 beds | 6 baths | 4,875 sq.ft. |
$3,299,000 |
Airbnb cash on cash: -0.02%
|
3455 ATHENA DRIVEWinter Park, FLWelcome to one of the larger homes in the community, where comfort and versatility meet. T... |
4 beds | 2 baths | 2,161 sq.ft. |
$465,500 |
Airbnb cash on cash: 8.64%
|
5466 BRACKEN COURTWinter Park, FLGreat value for a three bedroom home in Winter Park! This two story town home has the prim... |
3 beds | 3 baths | 1,332 sq.ft. |
$293,500 |
Airbnb cash on cash: 9.78%
|
1005 FAIRWAY DRIVEWinter Park, FLWelcome to this newly renovated gem nestled along the ninth hole of the WP18 golf course. ... |
4 beds | 3 baths | 2,584 sq.ft. |
$799,000 |
Airbnb cash on cash: 4.2%
|
241 W LAKE SUE AVENUEWinter Park, FLUnder contract-accepting backup offers. **Stunning Winter Park Home Near Rollins College, ... |
3 beds | 3 baths | 2,304 sq.ft. |
$950,000 |
Airbnb cash on cash: 1.31%
|
3651 N GOLDENROD ROAD #204Winter Park, FLWINTER PARK CONDO! This spacious condo is located just minutes from UCF, Rollins College a... |
2 beds | 2 baths | 840 sq.ft. |
$209,000 |
Airbnb cash on cash: 8.38%
|
1244 VIA SALERNOWinter Park, FLUnder contract-accepting backup offers. Stunning Mid-Century Modern Home in the Prestigiou... |
3 beds | 3 baths | 2,505 sq.ft. |
$1,875,000 |
Airbnb cash on cash: 0.16%
|
5240 N LAKE BURKETT LANEWinter Park, FLOne or more photo(s) has been virtually staged. Welcome to 5240 North Lake Burkett Lane, a... |
4 beds | 3 baths | 2,290 sq.ft. |
$535,000 |
Airbnb cash on cash: 7.19%
|
1190 VILLAGE FOREST PLACEWinter Park, FLUnder contract-accepting backup offers. NO HOA. HURRICANE PROOF WINDOWS! No preparation re... |
3 beds | 3 baths | 1,525 sq.ft. |
$420,000 |
Airbnb cash on cash: 6.89%
|
1350 LYNDALE BOULEVARDWinter Park, FLStep into a world of unmatched luxury and meticulous detail in this stunning custom-built ... |
4 beds | 5 baths | 3,478 sq.ft. |
$1,750,000 |
Airbnb cash on cash: 0.86%
|
3607 DATURA COURTWinter Park, FLThree bedroom/2 bath pool home located in a much sought after neighborhood in Winter Park.... |
3 beds | 2 baths | 1,380 sq.ft. |
$409,900 |
Airbnb cash on cash: 6.78%
|
1811 WINTER GREEN BOULEVARDWinter Park, FLWelcome to this charming property with a soothing neutral color scheme that exudes eleganc... |
3 beds | 2 baths | 1,187 sq.ft. |
$297,000 |
Airbnb cash on cash: 9.42%
|
281 BREWER AVENUEWinter Park, FLUnder contract-accepting backup offers. Stunning Custom Designed POOL Home - 5 Bedroom, 4.... |
5 beds | 5 baths | 4,029 sq.ft. |
$1,600,000 |
Airbnb cash on cash: N/A
|
1908 CARRIGAN AVENUEWinter Park, FLOne or more photo(s) has been virtually staged. Welcome to this stunning property with a n... |
2 beds | 2 baths | 1,122 sq.ft. |
$339,000 |
Airbnb cash on cash: 5.79%
|
2720 AMBERGATE ROADWinter Park, FL**Price Improvement**Charming Remodeled Winter Park Home! Welcome to 2720 Ambergate Road, ... |
3 beds | 1 baths | 1,188 sq.ft. |
$375,000 |
Airbnb cash on cash: 7.54%
|
8077 PLEASANT PINE CIRCLEWinter Park, FLWinter Park Home â Move in Ready **Seller Financing May be Available** Conveniently lo... |
4 beds | 4 baths | 3,215 sq.ft. |
$694,900 |
Airbnb cash on cash: 4.55%
|
1571 ONECO AVENUEWinter Park, FLUnder contract-accepting backup offers. Stunning, custom-built home in the Winter Park Tre... |
4 beds | 3 baths | 2,510 sq.ft. |
$1,190,000 |
Airbnb cash on cash: 2.35%
|
3318 AMBER WOOD WAY #100Winter Park, FLUnder contract-accepting backup offers. Great investment opportunity for contractors & han... |
2 beds | 3 baths | 1,031 sq.ft. |
$190,000 |
Airbnb cash on cash: 9.25%
|
363 N PHELPS AVENUEWinter Park, FLUnder contract-accepting backup offers. This light and bright, single-story, almost 3,000 ... |
4 beds | 3 baths | 2,871 sq.ft. |
$1,130,000 |
Airbnb cash on cash: 2.56%
|
1849 VIBURNUM LANEWinter Park, FLThis charming home is located near the highly desirable area of Winter Park! 4 bedroom 2 b... |
3 beds | 2 baths | 1,627 sq.ft. |
$389,900 |
Airbnb cash on cash: 7.17%
|
1310 ALOMA AVENUEWinter Park, FLUnder contract-accepting backup offers. Elegant Spanish 4 bedroom, 2.5 bathroom home. Bea... |
4 beds | 3 baths | 2,533 sq.ft. |
$850,000 |
Airbnb cash on cash: 3.6%
|
5229 N WOODCREST DRIVEWinter Park, FLUnder contract-accepting backup offers. Location!! Stylish and affordably priced, this ... |
3 beds | 2 baths | 1,242 sq.ft. |
$347,000 |
Airbnb cash on cash: 8.07%
|
2435 CHANTILLY AVENUEWinter Park, FLLocated in the heart of Winter Park, one of Orlandoâs desirable metro regions. This stun... |
4 beds | 5 baths | 3,055 sq.ft. |
$1,650,000 |
Airbnb cash on cash: 0.66%
|
512 BYRON ROADWinter Park, FLDiscover this charming home located in the desirable Winter Park area. Featuring a spaciou... |
2 beds | 2 baths | 1,353 sq.ft. |
$436,000 |
Airbnb cash on cash: 4.05%
|
311 E MORSE BOULEVARD #7-2Winter Park, FLEnjoy sunrise views over Lake Osceola from this Whispering Waters jewel box located just s... |
1 beds | 1 baths | 900 sq.ft. |
$520,000 |
Airbnb cash on cash: 0.1%
|
3136 HEARTLEAF PLACEWinter Park, FLWelcome to your Winter Park dream home! This stunning 4-bedroom, 3.5-bathroom residence of... |
4 beds | 4 baths | 2,717 sq.ft. |
$749,999 |
Airbnb cash on cash: 4.47%
|
675 OVERSPIN DRIVEWinter Park, FLWelcome to this beautiful, custom-built, Mediterranean-style home located in the historic ... |
4 beds | 4 baths | 2,764 sq.ft. |
$946,500 |
Airbnb cash on cash: 2.99%
|
4013 QUENITA DRIVEWinter Park, FL***MOTIVATED SELLER***Come see this "diamond in the rough" located in the sought-after cit... |
4 beds | 3 baths | 2,327 sq.ft. |
$535,000 |
Airbnb cash on cash: 6.68%
|
690 OSCEOLA AVENUE #610Winter Park, FLExperience the best of lakeside living in this stunning 2-bedroom, 2-bathroom condo on bea... |
2 beds | 2 baths | 1,328 sq.ft. |
$499,000 |
Airbnb cash on cash: 0.21%
|
2313 LOCH LOMOND DRIVEWinter Park, FLIncredible opportunity to own a property in the sought-after Winter Park 32792 area for th... |
1 beds | 1 baths | 1,570 sq.ft. |
$539,000 |
Airbnb cash on cash: 1.65%
|
618 SAINT JOHNS COURTWinter Park, FL**Investment Opportunity:** (TENANT IN PLACE. UNTIL MARCH 31, 2025. DO NOT DISTURBE THE TE... |
2 beds | 2 baths | 1,037 sq.ft. |
$233,000 |
Airbnb cash on cash: 7.06%
|
1781 GOODRICH AVENUEWinter Park, FLIntroducing an exquisite Modern English Cottage by Floridian Custom Homes. This pool home ... |
4 beds | 4 baths | 2,701 sq.ft. |
$1,950,000 |
Airbnb cash on cash: 1.21%
|
344 STARLING ROADWinter Park, FLMODERN CHARM IN SOUGHT-AFTER WINTER PARK. Step into this beautifully remodeled 3-bedroom, ... |
3 beds | 3 baths | 1,345 sq.ft. |
$649,000 |
Airbnb cash on cash: 3.57%
|
1250 S PENNSYLVANIA AVENUE #8Winter Park, FLQuiet Virginia Heights Neighborhood with Stunning: private lake access park, walk to town ... |
3 beds | 3 baths | 1,957 sq.ft. |
$829,000 |
Airbnb cash on cash: 0.74%
|
Real Estate investment in Winter-park, FL
There are 189 properties for sale in the city of Winter Park . The median list price in Winter Park is $489,000 and the average price per square foot is $254. In December 2024, the average monthly cash on cash return in Winter Park is 3.00%. The average monthly rental income in Winter Park is $2,344.