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.
Condos for Sale in Winter Park, FL
Search for Condo for Sale in Winter Park, Florida. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.
Showing 30 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
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%
|
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. |
$570,000 |
Airbnb cash on cash: 2.5%
|
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%
|
300 CAROLINA AVENUE #201Winter Park, FLExperience the best of Winter Park living in this beautifully updated 2-bedroom, 2-bath co... |
2 beds | 2 baths | 1,305 sq.ft. |
$739,000 |
Airbnb cash on cash: 1.61%
|
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. |
$145,000 |
Airbnb cash on cash: 8.17%
|
101 S INTERLACHEN AVENUE #104Winter Park, FLFIRST TIME ON THE MARKET! ULTRA-RARE GROUND FLOOR CONDO IN DOWNTOWN WINTER PARK'S LACHEN H... |
2 beds | 2 baths | 949 sq.ft. |
$635,000 |
Airbnb cash on cash: 2.43%
|
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. |
$195,000 |
Airbnb cash on cash: 9.06%
|
151 N ORLANDO AVENUE #204Winter Park, FLOne or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restric... |
2 beds | 1 baths | 710 sq.ft. |
$229,000 |
Airbnb cash on cash: 6.81%
|
240 KILLARNEY BAY COURT #4Winter Park, FLWelcome to Killarney BayâWinter Parkâs best-kept secret for tranquil lakeside living, ... |
2 beds | 3 baths | 1,536 sq.ft. |
$399,000 |
Airbnb cash on cash: 3.86%
|
311 E MORSE BOULEVARD #7-5Winter Park, FLMajor Price Improvement! Here is your rare opportunity to own a studio apartment in Whispe... |
1 beds | 1 baths | 482 sq.ft. |
$359,000 |
Airbnb cash on cash: 3.19%
|
151 N ORLANDO AVENUE #101Winter Park, FLWelcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled ... |
2 beds | 1 baths | 804 sq.ft. |
$260,000 |
Airbnb cash on cash: 7.61%
|
640 PARK AVENUE N #26Winter Park, FLA gem in the heart of the city -was completely renovated in 2024, downtown Winter Park -wa... |
2 beds | 2 baths | 858 sq.ft. |
$572,500 |
Airbnb cash on cash: 2.63%
|
265 E CANTON AVENUE #GEWinter Park, FLRARE CORNER TOP-FLOOR CONDO WITH AMAZING VIEWS â FULLY FURNISHED AND IN THE HEART OF WIN... |
2 beds | 2 baths | 1,057 sq.ft. |
$631,400 |
Airbnb cash on cash: 0.28%
|
660 OSCEOLA AVENUE #101Winter Park, FLImagine waking, relaxing, and entertaining with serene lakefront views in this elegant gro... |
3 beds | 4 baths | 2,714 sq.ft. |
$2,295,000 |
Airbnb cash on cash: -0.9%
|
1134 WASHINGTON AVENUE #13Winter Park, FLDiscover this generously sized 3-bedroom, 3.5-bath townhome offering 2,083 square feet of ... |
3 beds | 4 baths | 2,083 sq.ft. |
$675,000 |
Airbnb cash on cash: 3.19%
|
311 E MORSE BOULEVARD #6-3Winter Park, FLDiscover your new downtown Winter Park ground-floor pied-Ã -terre. Two blocks from Park Av... |
1 beds | 1 baths | 570 sq.ft. |
$329,000 |
Airbnb cash on cash: 3.46%
|
151 N ORLANDO AVENUE #115Winter Park, FLWelcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. F... |
2 beds | 1 baths | 710 sq.ft. |
$298,000 |
Airbnb cash on cash: 4.78%
|
851 MILES AVENUE #13Winter Park, FLWelcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor c... |
2 beds | 1 baths | 808 sq.ft. |
$219,000 |
Airbnb cash on cash: 9.53%
|
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%
|
520 KILLARNEY BAY COURT #2Winter Park, FLUnder contract-accepting backup offers. PRICED TO SELL! Nestled in the heart of Winter Par... |
2 beds | 2 baths | 1,160 sq.ft. |
$339,000 |
Airbnb cash on cash: 5.39%
|
640 KILLARNEY BAY COURT #4Winter Park, FLOne or more photo(s) has been virtually staged. Tucked away on the tranquil shores of Lake... |
2 beds | 3 baths | 1,718 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.66%
|
3019 ANTIQUE OAKS CIRCLE #124Winter Park, FLInvestment Opportunity calling you!! Are you looking to start a portfolio of properties wi... |
1 beds | 1 baths | 749 sq.ft. |
$158,500 |
Airbnb cash on cash: 6.94%
|
296 LEWFIELD CIRCLEWinter Park, FL1 bed, 1 bath condo in Winter Park |
1 beds | 1 baths | 678 sq.ft. |
$157,000 |
Airbnb cash on cash: 7.31%
|
225 LEWFIELD CIRCLE #225Winter Park, FLOne or more photo(s) has been virtually staged. **This property qualifies for a closing co... |
2 beds | 2 baths | 953 sq.ft. |
$200,000 |
Airbnb cash on cash: 8.6%
|
7707 COUNTRY PLACE #4Winter Park, FLBeautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. ... |
2 beds | 2 baths | 1,068 sq.ft. |
$259,900 |
Airbnb cash on cash: 6.93%
|
2458 GRAND TETON CIRCLE #2458Winter Park, FLWelcome to your dream home in Winter Park! This beautifully updated, spacious two-bedroom ... |
2 beds | 2 baths | 1,457 sq.ft. |
$310,000 |
Airbnb cash on cash: 6.29%
|
182 SCOTTSDALE SQUARE #182Winter Park, FLDon't miss this exceptional opportunity to invest in a 1-bedroom, 1-bathroom condo in the ... |
1 beds | 1 baths | 756 sq.ft. |
$80,000 |
Airbnb cash on cash: -9.17%
|
311 SCOTTSDALE SQUARE #311Winter Park, FLThis 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a re... |
1 beds | 1 baths | 785 sq.ft. |
$110,000 |
Airbnb cash on cash: -7.79%
|
151 LEWFIELD CIRCLE #4Winter Park, FLEnjoy Winter Park lifestyle in this great, first floor, 1 bedroom 1 bath condo. Built in 1... |
1 beds | 1 baths | 678 sq.ft. |
$155,000 |
Airbnb cash on cash: 9.85%
|
200 SAINT ANDREWS BOULEVARD #2306Winter Park, FLExcellent opportunity in a prime location in Central Florida. This two-bedroom, two-full-b... |
2 beds | 2 baths | 1,015 sq.ft. |
$219,000 |
Airbnb cash on cash: 7.28%
|