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 Condos for Sale in Winter Park, Florida. Browse all of Mashvisor’s Condos listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.
Showing 179 Condos listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
1270 ARLINGTON PLACEWinter Park, FLModern Elegance in the Heart of Winter Park! Located just a half-mile from the renowned... |
3 beds | 4 baths | 2,964 sq.ft. |
$1,599,000 |
Airbnb cash on cash: 0.01%
|
715 VIA BELLAWinter Park, FLUnder contract-accepting backup offers. Tucked away on a quiet cul-de-sac lined with multi... |
5 beds | 4 baths | 4,328 sq.ft. |
$2,219,000 |
Airbnb cash on cash: N/A
|
1408 CHAPMAN CIRCLEWinter Park, FLNestled in the Elizabethâs Walk subdivision in the highly desirable Windsong community o... |
4 beds | 4 baths | 3,237 sq.ft. |
$1,525,000 |
Airbnb cash on cash: 1.02%
|
740 BAFFIE AVENUEWinter Park, FLWelcome to this fully remodeled, move in ready home perfectly situated on a spacious corne... |
3 beds | 2 baths | 1,456 sq.ft. |
$445,000 |
Airbnb cash on cash: 5.82%
|
1018 TURNER ROADWinter Park, FLSeller may consider buyer concessions if made in an offer | Lakefront charm meets quiet lu... |
3 beds | 2 baths | 2,237 sq.ft. |
$835,000 |
Airbnb cash on cash: 2.27%
|
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%
|
1324 INDIANA AVENUEWinter Park, FLCharming two story bungalow built in 1935. Timeless character meets modern comfort in this... |
4 beds | 3 baths | 1,692 sq.ft. |
$745,000 |
Airbnb cash on cash: 4.32%
|
2550 VENETIAN WAYWinter Park, FL"The richness of an artist is the fusion of influences that have shaped his life and work"... |
4 beds | 5 baths | 4,875 sq.ft. |
$2,499,000 |
Airbnb cash on cash: 0.3%
|
720 N PENNSYLVANIA AVENUEWinter Park, FLNestled in one of Winter Parkâs most sought-after locations, this 3-bedroom, 2-bathroom ... |
3 beds | 2 baths | 1,115 sq.ft. |
$550,000 |
Airbnb cash on cash: 4.56%
|
701 DENTON ROADWinter Park, FLMotivated Seller! Contact us today. Welcome to this beautifully upgraded home in Winter Pa... |
3 beds | 2 baths | 2,268 sq.ft. |
$565,000 |
Airbnb cash on cash: 4.22%
|
1400 S PENNSYLVANIA AVENUEWinter Park, FLLook at this rare opportunity to own a chic and trendy residence in winter park in an incr... |
4 beds | 3 baths | 2,310 sq.ft. |
$1,250,000 |
Airbnb cash on cash: 1.79%
|
208 BREWER AVENUEWinter Park, FLWelcome to this beautifully updated 4-bedroom, 3.5-bath Craftsman-style home, offering jus... |
4 beds | 4 baths | 2,173 sq.ft. |
$925,000 |
Airbnb cash on cash: 3.29%
|
1213 LINDENWOOD LANEWinter Park, FLDiscover the perfect blend of mid-century modern architecture and contemporary living in t... |
4 beds | 2 baths | 2,505 sq.ft. |
$750,000 |
Airbnb cash on cash: 4.66%
|
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%
|
2417 PASSAMONTE DRIVE #1EWinter Park, FLLocation! Location! Location! Winter Park, Top Rated Florida Zone Schools, Move-In Ready, ... |
3 beds | 3 baths | 1,837 sq.ft. |
$329,999 |
Airbnb cash on cash: 7.38%
|
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%
|
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. |
$530,000 |
Airbnb cash on cash: 4.73%
|
1509 WINTER GREEN BOULEVARDWinter Park, FLUpdated 3-Bedroom, 3-Bath Townhouse in Winter Green Community â Move-In Ready! Welcome ... |
3 beds | 3 baths | 1,652 sq.ft. |
$319,900 |
Airbnb cash on cash: 8.11%
|
1600 PALMER AVENUEWinter Park, FLDiscover refined elegance in this meticulously updated 3-bedroom, 2.5-bath two-story resid... |
3 beds | 3 baths | 2,550 sq.ft. |
$1,200,000 |
Airbnb cash on cash: 1.24%
|
726 N PENNSYLVANIA AVENUEWinter Park, FLWelcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of moder... |
3 beds | 2 baths | 1,167 sq.ft. |
$695,000 |
Airbnb cash on cash: 3.43%
|
1849 VIBURNUM LANEWinter Park, FLNestled near the highly sought-after Winter Park area, this beautifully updated 4-bedroom,... |
4 beds | 2 baths | 1,627 sq.ft. |
$425,000 |
Airbnb cash on cash: 9.46%
|
720 W WEBSTER AVENUEWinter Park, FLDiscover the charm of Winter Park living in this beautifully maintained 1950s home, where ... |
3 beds | 2 baths | 1,356 sq.ft. |
$575,000 |
Airbnb cash on cash: 4.32%
|
875 W LYMAN AVENUEWinter Park, FLDon't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 ... |
2 beds | 2 baths | 760 sq.ft. |
$475,000 |
Airbnb cash on cash: 3.73%
|
541 W CANTON AVENUEWinter Park, FLTimeless elegance meets boutique craftsmanship at 541 W Canton Avenueâan exceptional new... |
4 beds | 4 baths | 3,553 sq.ft. |
$2,935,000 |
Airbnb cash on cash: 0.5%
|
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%
|
2218 KING RICHARDS COURTWinter Park, FLOne or more photo(s) has been virtually staged. Welcome home to 2218 King Richards Court â... |
3 beds | 2 baths | 1,562 sq.ft. |
$450,000 |
Airbnb cash on cash: 5.83%
|
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%
|
1229 PARK GREEN PLACEWinter Park, FLThis 2 bedroom, 2 bathroom townhome offers 1,495 square feet of beautifully designed space... |
2 beds | 2 baths | 1,495 sq.ft. |
$372,500 |
Airbnb cash on cash: 4.02%
|
1621 PURITAN,Winter Park, FLUnder contract-accepting backup offers. Down Payment Assistance Available! Welcome to 1621... |
4 beds | 2 baths | 1,765 sq.ft. |
$440,000 |
Airbnb cash on cash: 8.97%
|
250 Cortland AvenueWinter Park, FLWelcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among mil... |
3 beds | 2 baths | 2,114 sq.ft. |
$950,000 |
Airbnb cash on cash: 2.31%
|
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%
|
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%
|
2189 SUSSEX ROADWinter Park, FLOne or more photo(s) has been virtually staged. AGENTS - PLEASE VIEW REALTOR REMARKS IN TH... |
4 beds | 3 baths | 1,776 sq.ft. |
$395,000 |
Airbnb cash on cash: 9.95%
|
525 S LAKEMONT AVENUEWinter Park, FLUnder Construction. Winter Park Luxury Awaits You! Welcome to your dream homeâa stunn... |
4 beds | 4 baths | 3,330 sq.ft. |
$2,350,000 |
Airbnb cash on cash: 0.77%
|
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%
|
1174 WILDMEADOW RUNWinter Park, FLWelcome to Hawks Crest â Winter Parkâs premier gated, resort-style community! This bea... |
3 beds | 3 baths | 1,770 sq.ft. |
$669,000 |
Airbnb cash on cash: 3%
|
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. |
$949,000 |
Airbnb cash on cash: 1.22%
|
1985 Japonica RoadWinter Park, FLOne or more photo(s) has been virtually staged. One or more photos were edited virtually. ... |
4 beds | 2 baths | 2,096 sq.ft. |
$659,900 |
Airbnb cash on cash: 5.53%
|
7641 Village Green DriveWinter Park, FLWelcome to this inviting single-family home at 7641 Village Green Dr in desirable Winter P... |
3 beds | 3 baths | 1,602 sq.ft. |
$550,000 |
Airbnb cash on cash: 4.45%
|
1250 FORMOSA AVENUEWinter Park, FLModern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nest... |
3 beds | 4 baths | 1,937 sq.ft. |
$590,000 |
Airbnb cash on cash: 3.15%
|