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 49 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
100 S VIRGINIA AVENUE #319Winter Park, FLUnder contract-accepting backup offers. Experience the best of Winter Park living in this ... |
3 beds | 3 baths | 2,649 sq.ft. |
$1,079,000 |
Airbnb cash on cash: 0.19%
|
1308 S PENNSYLVANIA AVENUE #3Winter Park, FL$25,000 below appraised value! Walk to Park Ave!! Sip coffee or tea overlooking lush Mead ... |
1 beds | 1 baths | 823 sq.ft. |
$325,000 |
Airbnb cash on cash: 3.63%
|
3651 N GOLDENROD ROAD #210Winter Park, FLbeautiful Condo in of Winter Park. This spacious second-floor unit is filled with natur... |
2 beds | 2 baths | 840 sq.ft. |
$191,000 |
Airbnb cash on cash: 9.87%
|
1000 S SEMORAN BOULEVARD #415Winter Park, FLNEW AC INSTALLED, PRICE REDUCTION, EXCELLENT INVESTMENT OPPORTUNITY, Great Tenant in place... |
1 beds | 1 baths | 735 sq.ft. |
$115,950 |
Airbnb cash on cash: 9.62%
|
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. |
$362,500 |
Airbnb cash on cash: 4.55%
|
690 OSCEOLA AVENUE #209Winter Park, FLOne or more photo(s) has been virtually staged. Seller financing and lease to own options ... |
2 beds | 2 baths | 1,148 sq.ft. |
$398,800 |
Airbnb cash on cash: 4.76%
|
260 KILLARNEY BAY COURT #6-6Winter Park, FLWelcome to Killarney Bay! This beautifully updated 2-bedroom, 1-bathroom Second-floor cond... |
2 beds | 1 baths | 1,140 sq.ft. |
$345,000 |
Airbnb cash on cash: 4.32%
|
1250 S DENNING DRIVE #111Winter Park, FLUnder contract-accepting backup offers. LOCATION LOCATION!! Now is your chance to own this... |
2 beds | 2 baths | 908 sq.ft. |
$259,000 |
Airbnb cash on cash: 4.81%
|
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. |
$599,000 |
Airbnb cash on cash: 2.33%
|
2238 HAWICK LANE #2238Winter Park, FLWelcome to 2238 Hawick Lane, where modern living meets timeless charm in Winter Park, FL! ... |
3 beds | 3 baths | 1,775 sq.ft. |
$529,000 |
Airbnb cash on cash: 4.03%
|
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. |
$415,000 |
Airbnb cash on cash: 0.37%
|
680 GRENADINE COURT #SWinter Park, FLUnder contract-accepting backup offers. Welcome to this beautifully renovated 1-bedroom, 1... |
1 beds | 1 baths | 759 sq.ft. |
$190,000 |
Airbnb cash on cash: 5.01%
|
690 OSCEOLA AVENUE #502Winter Park, FLBeautifully Renovated Lakefront Condo with Partial Lake Virginia & Downtown Views. Located... |
2 beds | 2 baths | 1,400 sq.ft. |
$525,000 |
Airbnb cash on cash: 0.15%
|
3019 ANTIQUE OAKS CIRCLE #124Winter Park, FLPrime Location and Zip Code are key! Welcome home to 3019 Antique Oaks Circle Unit 124 at ... |
1 beds | 1 baths | 749 sq.ft. |
$175,000 |
Airbnb cash on cash: 6.21%
|
535 N INTERLACHEN AVENUE #106Winter Park, FLRare opportunity to own a first floor unit with soaring 9 foot ceilings only steps away fr... |
2 beds | 2 baths | 1,000 sq.ft. |
$649,900 |
Airbnb cash on cash: 2.67%
|
1276 S PENNSYLVANIA AVENUE #12Winter Park, FLUnder contract-accepting backup offers. Nestled within the tranquil confines of the Virgin... |
3 beds | 3 baths | 1,957 sq.ft. |
$829,000 |
Airbnb cash on cash: 2.09%
|
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%
|
3651 N GOLDENROD ROAD E #102Winter Park, FLWelcome to this beautifully updated 2 bedroom/ 2 bath first floor condo. This open flo... |
2 beds | 2 baths | 840 sq.ft. |
$192,000 |
Airbnb cash on cash: 9.12%
|
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. |
$200,000 |
Airbnb cash on cash: 5.71%
|
108 SCOTTSDALE SQUARE #108Winter Park, FLThis beautiful second to third floor condo has the feel of a townhouse/residential treehou... |
3 beds | 2 baths | 1,300 sq.ft. |
$174,900 |
Airbnb cash on cash: -3.78%
|
334 SCOTTSDALE SQUARE #334Winter Park, FLCASH ONLY. Desirable Winter Park Location with highly rated schools! Down the street Full ... |
3 beds | 2 baths | 1,250 sq.ft. |
$130,000 |
Airbnb cash on cash: -5.74%
|
337 SCOTTSDALE SQUARE #337Winter Park, FLJust Reduced!! Great opportunity. This well-maintained unit offers a combination of functi... |
1 beds | 1 baths | 785 sq.ft. |
$80,000 |
Airbnb cash on cash: -9.79%
|
7466 CANFORD COURT #25Winter Park, FLMOTIVATED SELLER. Welcome to this cozy and well-maintained condo with a townhome feel nest... |
2 beds | 2 baths | 1,393 sq.ft. |
$197,990 |
Airbnb cash on cash: 7.31%
|
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. |
$699,000 |
Airbnb cash on cash: 2.12%
|
700 MELROSE AVENUE #L-23Winter Park, FLUnder contract-accepting backup offers. Welcome to your serene retreat in the highly desir... |
1 beds | 1 baths | 787 sq.ft. |
$245,000 |
Airbnb cash on cash: 5.64%
|
200 ST ANDREWS BOULEVARD #512Winter Park, FL**This property qualifies for a closing cost credit up to $2,700 through the Sellerâs pr... |
1 beds | 1 baths | 835 sq.ft. |
$165,500 |
Airbnb cash on cash: 6.19%
|
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. |
$215,000 |
Airbnb cash on cash: 8.15%
|
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. |
$639,000 |
Airbnb cash on cash: 1.49%
|
225 E CANTON AVENUE #225Winter Park, FLUnder contract-accepting backup offers. This beautifully updated 2-bedroom, 2-bathroom cor... |
2 beds | 2 baths | 1,057 sq.ft. |
$649,000 |
Airbnb cash on cash: 2.18%
|
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. |
$241,900 |
Airbnb cash on cash: 6.51%
|
101 S NEW YORK AVENUE #311Winter Park, FLDiscover luxury living in this exquisite two-story condominium, located on the third floor... |
3 beds | 4 baths | 3,112 sq.ft. |
$1,650,000 |
Airbnb cash on cash: -0.76%
|
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. |
$241,000 |
Airbnb cash on cash: 6.43%
|
296 LEWFIELD CIRCLEWinter Park, FL1 bed, 1 bath condo in Winter Park |
1 beds | 1 baths | 678 sq.ft. |
$160,000 |
Airbnb cash on cash: 7.16%
|
184 SANDLEWOOD TRAIL #2Winter Park, FLFHA, VA, and DPA approved. Nestled just minutes from the charming boutiques and award-winn... |
2 beds | 3 baths | 1,133 sq.ft. |
$315,000 |
Airbnb cash on cash: 6.3%
|
1250 S DENNING DRIVE #108Winter Park, FLUnder contract-accepting backup offers. This move-in-ready, first-floor condo has been com... |
1 beds | 1 baths | 658 sq.ft. |
$179,900 |
Airbnb cash on cash: 6.04%
|
225 LEWFIELD CIRCLE #225Winter Park, FL**This property qualifies for a closing cost credit up to $3,300 through the Sellerâs pr... |
2 beds | 2 baths | 953 sq.ft. |
$210,000 |
Airbnb cash on cash: 8.15%
|
1602 ALABAMA DRIVE #PH404Winter Park, FLA Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare archite... |
3 beds | 4 baths | 2,709 sq.ft. |
$2,490,000 |
Airbnb cash on cash: -0.62%
|
1000 S SEMORAN BOULEVARD #604Winter Park, FLThis second floor Winter Park Condo has been beautifully renovated. The kitchen renovation... |
2 beds | 2 baths | 1,049 sq.ft. |
$195,000 |
Airbnb cash on cash: 9.71%
|
200 ST ANDREWS BOULEVARD #601Winter Park, FLWelcome to this spacious and beautifully updated first-floor condo with 1 bedroom, 1 bathr... |
1 beds | 1 baths | 727 sq.ft. |
$174,900 |
Airbnb cash on cash: 8.18%
|
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. |
$410,000 |
Airbnb cash on cash: 3.73%
|