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 |
|---|---|---|---|
318 GENIUS DRIVEWinter Park, FLUnder contract-accepting backup offers. Welcome to your dream home in the prestigious Wind... |
5 beds | 7 baths | 6,223 sq.ft. |
$3,650,000 |
Airbnb cash on cash: N/A
|
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%
|
4025 QUENITA DRIVEWinter Park, FLNestled within the desirable family community of Lake Waunatta Woods, this home is beautif... |
4 beds | 2 baths | 1,898 sq.ft. |
$580,000 |
Airbnb cash on cash: 6.23%
|
1481 HARMON AVENUEWinter Park, FLOwner Financing Available! Welcome to this charming four-bedroom, three-bath home nestled ... |
4 beds | 3 baths | 1,705 sq.ft. |
$545,000 |
Airbnb cash on cash: 6.76%
|
1700 PALM AVENUEWinter Park, FLUnder contract-accepting backup offers. Stunning Winter Park modern home on the tree stree... |
4 beds | 5 baths | 3,762 sq.ft. |
$2,500,000 |
Airbnb cash on cash: 0.29%
|
100 S VIRGINIA AVENUE #201Winter Park, FLDiscover luxury living in this exquisite single-story condominium, located on the second f... |
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. |
$949,000 |
Airbnb cash on cash: 2.36%
|
5318 POINSETTA AVENUEWinter Park, FLUnder contract-accepting backup offers. Welcome to your beautifully updated Winter Park ho... |
3 beds | 2 baths | 1,467 sq.ft. |
$420,000 |
Airbnb cash on cash: 6.87%
|
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. |
$469,000 |
Airbnb cash on cash: 8.56%
|
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%
|
5211 WOODCREST COURTWinter Park, FLUnder contract-accepting backup offers. Stylish fully renovated 3 bedroom 2 bath home, wit... |
3 beds | 2 baths | 1,578 sq.ft. |
$484,000 |
Airbnb cash on cash: 5.78%
|
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. |
$824,000 |
Airbnb cash on cash: 4.04%
|
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%
|
432 WORTHINGTON DRIVEWinter Park, FLUnder contract-accepting backup offers. Discover a charming, single story home in the hear... |
3 beds | 1 baths | 1,243 sq.ft. |
$749,000 |
Airbnb cash on cash: 2.87%
|
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, FLWelcome to 5240 North Lake Burkett Lane, a classic 4 bedroom, 2.5 bathroom home, located i... |
4 beds | 3 baths | 2,290 sq.ft. |
$575,000 |
Airbnb cash on cash: 6.63%
|
1190 VILLAGE FOREST PLACEWinter Park, FLNO HOA. HURRICANE PROOF WINDOWS! No preparation required, owner has updated all windows in... |
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%
|
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%
|
2434 BARBADOS DRIVEWinter Park, FLGreat Schools, Great Location! Great investment property. Low HOA's. This unit offers 3 ... |
3 beds | 2 baths | 1,284 sq.ft. |
$299,000 |
Airbnb cash on cash: 9.48%
|
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. |
$340,000 |
Airbnb cash on cash: 5.77%
|
2720 AMBERGATE ROADWinter Park, FLUnder contract-accepting backup offers. **Price Improvement**Charming Remodeled Winter Par... |
3 beds | 1 baths | 1,188 sq.ft. |
$375,000 |
Airbnb cash on cash: 7.54%
|
8077 PLEASANT PINE CIRCLEWinter Park, FLBeautiful Winter Park Home Looking for New Owner! **Seller Financing is Available** Conv... |
4 beds | 4 baths | 3,215 sq.ft. |
$699,900 |
Airbnb cash on cash: 4.51%
|
1571 ONECO AVENUEWinter Park, FLStunning, custom-built home in the Winter Park Tree Streets. This beautifully designed, Me... |
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, FLThis light and bright, single-story, almost 3,000 square foot pool home features a split p... |
4 beds | 3 baths | 2,871 sq.ft. |
$1,170,000 |
Airbnb cash on cash: 2.44%
|
1616 HIBISCUS AVENUEWinter Park, FLUnder contract-accepting backup offers. Stunning transitional modern home located in the h... |
4 beds | 5 baths | 3,897 sq.ft. |
$2,150,000 |
Airbnb cash on cash: 0.23%
|
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%
|
2427 GALLERY VIEW DRIVE #7Winter Park, FLRemarkable Winter Park condo looking for new owner. Great opportunity 1st floor, overlook... |
2 beds | 2 baths | 1,004 sq.ft. |
$295,000 |
Airbnb cash on cash: 5.31%
|
3463 ARNEL DRIVEWinter Park, FL**This property qualifies for a closing cost credit up to $3,100 through the Sellerâs pr... |
3 beds | 2 baths | 1,750 sq.ft. |
$410,000 |
Airbnb cash on cash: 6.58%
|
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. |
$450,000 |
Airbnb cash on cash: 3.9%
|
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%
|
Real Estate investment in Winter-park, FL
There are 182 properties for sale in the city of Winter Park . The median list price in Winter Park is $499,000 and the average price per square foot is $252. In November 2024, the average monthly cash on cash return in Winter Park is 3.00%. The average monthly rental income in Winter Park is $2,455.