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.
Investment Property for Sale in Winter Park, FL
| 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%
|
Real Estate investment in Winter-park, FL
There are 179 properties for sale in the city of Winter Park . The median list price in Winter Park is $565,000 and the average price per square foot is $271. In December 2025, the average monthly cash on cash return in Winter Park is 2.00%. The average monthly rental income in Winter Park is $2,229.