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 Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winter Park, FL
Search for Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winter Park, Florida. Browse all of Mashvisor’s Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.
Showing 185 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
640 ARJAY WAYWinter Park, FLPrice Improvement on this amazing oversized lot! Located in one of Winter Parkâs most de... |
5 beds | 5 baths | 3,953 sq.ft. |
$1,974,900 |
Airbnb cash on cash: N/A
|
1751 GOODRICH AVENUEWinter Park, FLWelcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park... |
4 beds | 4 baths | 2,170 sq.ft. |
$1,475,000 |
Airbnb cash on cash: 1.66%
|
3114 HEARTLEAF PLACEWinter Park, FLTucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in L... |
4 beds | 3 baths | 2,702 sq.ft. |
$699,900 |
Airbnb cash on cash: 4.92%
|
1018 TURNER ROADWinter Park, FLUnder contract-accepting backup offers. Seller may consider buyer concessions if made in a... |
3 beds | 2 baths | 2,237 sq.ft. |
$835,000 |
Airbnb cash on cash: 2.27%
|
1649 Harmon AveWinter Park, FLPriced to Close before the end of the year!!! New Construction Orwin Manor Area home tha... |
4 beds | 3 baths | 3,223 sq.ft. |
$1,450,000 |
Airbnb cash on cash: 2.18%
|
744 CORNWALL ROADWinter Park, FLWelcome to your dream home! This exceptional 4-bedroom residence features a desirable spli... |
4 beds | 2 baths | 1,968 sq.ft. |
$715,000 |
Airbnb cash on cash: 5.01%
|
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%
|
1000 S SEMORAN BOULEVARD #715Winter Park, FLPrime location meets exceptional value in the highly sought-after Winter Park area! This f... |
1 beds | 1 baths | 735 sq.ft. |
$122,990 |
Airbnb cash on cash: 8.99%
|
2919 BOWER ROADWinter Park, FLBeautifully updated 3BR/2BA pool home in the highly sought-after Winter Pines community of... |
3 beds | 2 baths | 2,325 sq.ft. |
$779,000 |
Airbnb cash on cash: 2.33%
|
668 OVERSPIN DRIVEWinter Park, FLOne or more photo(s) has been virtually staged. A contemporary, beautifully finished home ... |
4 beds | 3 baths | 2,509 sq.ft. |
$875,000 |
Airbnb cash on cash: 3.21%
|
418 GILBERT ROADWinter Park, FLBeautifully renovated solid block home on a quiet street in highly desirable Winter Park P... |
3 beds | 3 baths | 1,680 sq.ft. |
$740,000 |
Airbnb cash on cash: 2.61%
|
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. |
$335,000 |
Airbnb cash on cash: 4.49%
|
1521 CHESTNUT AVENUEWinter Park, FLModern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thou... |
4 beds | 3 baths | 2,842 sq.ft. |
$1,899,900 |
Airbnb cash on cash: 0.48%
|
1518 PINEWOOD DRIVEWinter Park, FLIncome-producing home with a detached in-law apartment in a prime central Orlando location... |
3 beds | N/A baths | 1,197 sq.ft. |
$415,000 |
Airbnb cash on cash: 8.94%
|
2918 ANTIQUE OAKS CIRCLE #25Winter Park, FL2 Bedroom 2 bath condo 1 block south of University Blvd great location for UCF or Full Sai... |
2 beds | 2 baths | 1,018 sq.ft. |
$189,000 |
Airbnb cash on cash: 8.73%
|
346 S RANGER BOULEVARDWinter Park, FLPRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park... |
3 beds | 2 baths | 1,592 sq.ft. |
$485,000 |
Airbnb cash on cash: 5.25%
|
7336 FOREST HILL COURT #240Winter Park, FLUpdated Winter Park Townhome!! If you are looking for LOCATION this is the property for yo... |
2 beds | 2 baths | 990 sq.ft. |
$179,900 |
Airbnb cash on cash: 8.72%
|
507 COUNTRY CLUB DRIVEWinter Park, FLUnder contract-accepting backup offers. Designed for elevated living in the heart of Winte... |
4 beds | 4 baths | 2,985 sq.ft. |
$1,550,000 |
Airbnb cash on cash: 1.17%
|
144 LEWFIELD CIRCLE #144Winter Park, FLLOCATION! LOCATION! LOCATION! Beautiful 2nd floor corner condo in desirable Winter Park, f... |
1 beds | 1 baths | 678 sq.ft. |
$144,000 |
Airbnb cash on cash: 8.2%
|
948 POINCIANA LANEWinter Park, FLTimeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an ... |
4 beds | 4 baths | 3,676 sq.ft. |
$3,199,000 |
Airbnb cash on cash: -0.1%
|
764 W COMSTOCK AVENUEWinter Park, FLUnder contract-accepting backup offers. Welcome to this charming 1935 Winter Park bungalow... |
2 beds | 1 baths | 925 sq.ft. |
$474,000 |
Airbnb cash on cash: 3.41%
|
5418 ARDMORE DRIVEWinter Park, FLOne or more photo(s) has been virtually staged. **WELCOME HOME** A generous .23 ACRE LOT, ... |
3 beds | 2 baths | 1,560 sq.ft. |
$450,000 |
Airbnb cash on cash: 5.98%
|
1354 TIERRA CIRCLEWinter Park, FLLocated in the highly sought-after Casa Aloma community, this charming 1960s home offers t... |
4 beds | 2 baths | 1,827 sq.ft. |
$435,000 |
Airbnb cash on cash: 9.18%
|
1849 VIBURNUM LANEWinter Park, FLThis beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright... |
4 beds | 2 baths | 1,627 sq.ft. |
$425,000 |
Airbnb cash on cash: 9.46%
|
720 W WEBSTER AVENUEWinter Park, FLOne or more photo(s) has been virtually staged. This home can be purchased with NO INCOME ... |
3 beds | 2 baths | 1,356 sq.ft. |
$550,000 |
Airbnb cash on cash: 4.56%
|
2217 SUSSEX ROADWinter Park, FLPRICE REDUCED!!! 4 BEDROOMS with OFFICE POOL HOME. MOTIVATED SELLERS. MOVE IN READY! THI... |
4 beds | 2 baths | 2,092 sq.ft. |
$520,000 |
Airbnb cash on cash: 7.32%
|
503 W CANTON AVENUEWinter Park, FLWalk to Park Avenue! Model Home, tons of upgrades. Enjoy luxury living and premium sought ... |
3 beds | 3 baths | 2,342 sq.ft. |
$1,146,000 |
Airbnb cash on cash: 0.1%
|
3463 ARNEL DRIVEWinter Park, FLYour pool home in Winter Park. This home offers three bedrooms plus a versatile bonus r... |
3 beds | 2 baths | 1,770 sq.ft. |
$479,900 |
Airbnb cash on cash: 5.45%
|
1800 MAGNOLIA AVENUEWinter Park, FLOne or more photo(s) has been virtually staged. Experience refined living in this exquisit... |
4 beds | 3 baths | 2,431 sq.ft. |
$1,150,000 |
Airbnb cash on cash: 2.2%
|
311 E MORSE BOULEVARD #7-2Winter Park, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. En... |
1 beds | 1 baths | 900 sq.ft. |
$399,000 |
Airbnb cash on cash: -0.26%
|
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. |
$775,000 |
Airbnb cash on cash: 3.75%
|
2036 VIA TUSCANYWinter Park, FLWINTER PARK VIAâS!!! Incredible Oversized Lot is located in the âHeartâ of Winter Pa... |
3 beds | 2 baths | 2,148 sq.ft. |
$2,000,000 |
Airbnb cash on cash: 0.04%
|
189 LEWFIELD CIRCLE #189Winter Park, FLExperience the best of the Winter Park lifestyle in this beautifully updated first-floor c... |
1 beds | 1 baths | 678 sq.ft. |
$155,000 |
Airbnb cash on cash: 6.87%
|
2126 N HAMPTON CIRCLEWinter Park, FLUnder contract-accepting backup offers. Step into your own private retreat in the sought-a... |
3 beds | 2 baths | 1,745 sq.ft. |
$500,000 |
Airbnb cash on cash: 5.18%
|
1473 Berkshire AveWinter Park, FLExquisite New 2025 Luxury Home in the Heart of Winter Park - Welcome to 1473 Berkshire Ave... |
5 beds | 4 baths | 2,895 sq.ft. |
$1,499,000 |
Airbnb cash on cash: N/A
|
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%
|
1028 LAKE BELL DRIVEWinter Park, FLUnder contract-accepting backup offers. WELCOME HOME to this rare Winter Park opportunity!... |
2 beds | 2 baths | 1,418 sq.ft. |
$400,000 |
Airbnb cash on cash: 4.2%
|
3019 ANTIQUE OAKS CIRCLE #124Winter Park, FLThe Ultimate Winter Park is your every desire. Investment Potential, Student Sanctuary or ... |
1 beds | 1 baths | 749 sq.ft. |
$154,000 |
Airbnb cash on cash: 7.17%
|
1929 S LAKEMONT AVENUEWinter Park, FLThis modern Winter Park townhome sits in a quiet pocket between Lake Spier and Lake Compto... |
3 beds | 4 baths | 2,160 sq.ft. |
$915,000 |
Airbnb cash on cash: 1.3%
|
1985 Japonica RoadWinter Park, FLOne or more photo(s) has been virtually staged. New Price Adjusted, Welcome to 1985 Japoni... |
4 beds | 2 baths | 2,096 sq.ft. |
$599,997 |
Airbnb cash on cash: 6.18%
|