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 |
|---|---|---|---|
640 Arjay WayWinter Park, FLLocated in one of Winter Parkâs most desirable and picturesque neighborhoods, Timberlane... |
5 beds | 3 baths | 3,860 sq.ft. |
$1,974,900 |
Airbnb cash on cash: N/A
|
1751 Goodrich AveWinter Park, FLWelcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park... |
4 beds | 3 baths | 2,170 sq.ft. |
$1,475,000 |
Airbnb cash on cash: 1.66%
|
1408 Chapman CirWinter Park, FLOpportunity awaits in the most desirable neighborhood! Buyers have cold feet. Nestled in t... |
4 beds | 4 baths | 3,237 sq.ft. |
$1,495,000 |
Airbnb cash on cash: 1.06%
|
740 BAFFIE AVENUEWinter Park, FLUnder contract-accepting backup offers. Welcome to this fully remodeled, move in ready hom... |
3 beds | 2 baths | 1,456 sq.ft. |
$420,000 |
Airbnb cash on cash: 6.22%
|
1018 TURNER ROADWinter Park, FLUnder contract-accepting backup offers. Seller may consider buyer concessions if made in a... |
3 beds | 2 baths | 2,237 sq.ft. |
$835,000 |
Airbnb cash on cash: 2.27%
|
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%
|
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 LnWinter Park, FLDiscover the perfect blend of mid-century modern architecture and contemporary living in t... |
4 beds | 2 baths | 2,505 sq.ft. |
$739,900 |
Airbnb cash on cash: 4.66%
|
2811 EASTERN PARKWAYWinter Park, FLUnder contract-accepting backup offers. Mid-Century Modern architecture meets modern comfo... |
3 beds | 2 baths | 1,433 sq.ft. |
$625,000 |
Airbnb cash on cash: 3.82%
|
150 Killarney Bay Ct #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. |
$335,000 |
Airbnb cash on cash: 4.33%
|
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%
|
4591 WHIMBREL PLACEWinter Park, FLCharming home nestled in a small, quaint community on spacious, custom-home lots. This wel... |
3 beds | 2 baths | 1,942 sq.ft. |
$490,000 |
Airbnb cash on cash: 5.77%
|
346 S Ranger BlvdWinter Park, FLPRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park... |
3 beds | 2 baths | 1,592 sq.ft. |
$485,000 |
Airbnb cash on cash: 5.01%
|
1600 Palmer AveWinter 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%
|
948 Poinciana LnWinter Park, FLTimeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an ... |
4 beds | 3 baths | 3,676 sq.ft. |
$3,199,000 |
Airbnb cash on cash: -0.2%
|
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 LnWinter Park, FLThis beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright... |
4 beds | 2 baths | 1,627 sq.ft. |
$425,000 |
Airbnb cash on cash: 9.46%
|
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. |
$425,000 |
Airbnb cash on cash: 4.28%
|
503 W Canton AveWinter Park, FLMODEL HOME. Enjoy luxury living and premium sought after location at Vilasa Homes in Winte... |
3 beds | 2 baths | 2,342 sq.ft. |
$1,146,000 |
Airbnb cash on cash: 0.09%
|
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: -0.26%
|
1702 Glenridge WayWinter Park, FLRare opportunity in Winter Park to own a move-in-ready, fully renovated corner lakefront t... |
2 beds | 2 baths | 1,832 sq.ft. |
$789,000 |
Airbnb cash on cash: -0.64%
|
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 AveWinter 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%
|
3019 Antique Oaks Cir #124Winter Park, FLInvestors and Owner Occupied Welcome! Investors start your portfolio of properties with mo... |
1 beds | 1 baths | 749 sq.ft. |
$154,000 |
Airbnb cash on cash: 7.12%
|
2189 SUSSEX ROADWinter Park, FLOne or more photo(s) has been virtually staged. One or more photos have been virtually sta... |
4 beds | 3 baths | 1,776 sq.ft. |
$535,000 |
Airbnb cash on cash: 7.11%
|
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%
|
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 AveWinter Park, FLThis modern Winter Park townhome sits in a quiet pocket between Lake Spier and Lake Compto... |
3 beds | 3 baths | 2,160 sq.ft. |
$915,000 |
Airbnb cash on cash: 1.22%
|
1985 Japonica RdWinter Park, FLOne or more photo(s) has been virtually staged. Welcome to 1985 Japonica Rd-your newly rei... |
4 beds | 2 baths | 2,096 sq.ft. |
$599,997 |
Airbnb cash on cash: 5.84%
|
7641 Village Green DrWinter 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 AveWinter Park, FLModern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nest... |
3 beds | 3 baths | 1,937 sq.ft. |
$565,000 |
Airbnb cash on cash: 3.33%
|
Real Estate investment in Winter-park, FL
There are 358 properties for sale in the city of Winter Park . The median list price in Winter Park is $550,000 and the average price per square foot is $283. In March 2026, the average monthly cash on cash return in Winter Park is 2.00%. The average monthly rental income in Winter Park is $2,127.