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.
Woodlawn Investment Property for Sale in Winter Park, FL
Search for Woodlawn Investment Property for Sale in Winter Park, Florida. Browse all of Mashvisor’s Woodlawn Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.
Showing 358 Woodlawn Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| 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%
|
2217 Sussex RdWinter Park, FL4 BEDROOMS with OFFICE POOL HOME. MOTIVATED SELLERS. MOVE IN READY! THIS HOME WILL NOT L... |
4 beds | 2 baths | 2,092 sq.ft. |
$530,000 |
Airbnb cash on cash: 7.17%
|
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%
|