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 34 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%
|
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%
|
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. |
$575,000 |
Airbnb cash on cash: 2.47%
|
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%
|
520 KILLARNEY BAY COURT #2Winter Park, FLPRICED TO SELL! Nestled in the heart of Winter Park, this updated 2 bedroom, 2 bath second... |
2 beds | 2 baths | 1,160 sq.ft. |
$339,000 |
Airbnb cash on cash: 5.39%
|
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%
|
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. |
$649,000 |
Airbnb cash on cash: 2.35%
|
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. |
$200,000 |
Airbnb cash on cash: 8.82%
|
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%
|
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%
|
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. |
$309,000 |
Airbnb cash on cash: 6.44%
|
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%
|
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 & Motivated Seller! Here is your rare opportunity to own a studio ... |
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%
|
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%
|
151 N ORLANDO AVENUE #226Winter Park, FLNewly updated 2 Bedrooms and 1 Bathroom conveniently located in Winter Park/Orlando next t... |
2 beds | 1 baths | 768 sq.ft. |
$235,000 |
Airbnb cash on cash: 8.86%
|
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%
|
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. |
$160,000 |
Airbnb cash on cash: 7.33%
|
3019 ANTIQUE OAKS CIRCLE #124Winter Park, FLReady to move in? This home is exceptionally located in a great community. Prime Location ... |
1 beds | 1 baths | 749 sq.ft. |
$161,500 |
Airbnb cash on cash: 6.8%
|
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%
|
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%
|
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%
|
3651 N GOLDENROD ROAD #E102Winter Park, FLWelcome to this beautifully maintained 2-bedroom, 2-bathroom first-floor condo, offering c... |
2 beds | 2 baths | 840 sq.ft. |
$177,000 |
Airbnb cash on cash: 9.71%
|
200 SAINT ANDREWS BOULEVARD #101Winter Park, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. We... |
1 beds | 1 baths | 727 sq.ft. |
$150,000 |
Airbnb cash on cash: 9.72%
|
200 SAINT ANDREWS BOULEVARD #1707Winter Park, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. We... |
2 beds | 2 baths | 1,219 sq.ft. |
$215,000 |
Airbnb cash on cash: 7.87%
|
4892 TANGERINE AVENUE #4892Winter Park, FLUnder contract-accepting backup offers. Discover the perfect blend of comfort and convenie... |
1 beds | 1 baths | 747 sq.ft. |
$175,000 |
Airbnb cash on cash: 7.58%
|