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.
Single Family Homes for Sale in Winter Park, FL
Search for Single Family Residential for Sale in Winter Park, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.
Showing 124 Single Family Residential 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, FL$50,0000 Price Improvement on this amazing oversized lot! Located in one of Winter Parkâ... |
5 beds | 5 baths | 3,953 sq.ft. |
$1,925,000 |
Airbnb cash on cash: N/A
|
1751 GOODRICH AVENUEWinter Park, FLWelcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park... |
4 beds | 4 baths | 2,170 sq.ft. |
$1,475,000 |
Airbnb cash on cash: 1.66%
|
1649 Harmon AveWinter Park, FLPriced to Close before the end of the year!!! New Construction Orwin Manor Area home tha... |
4 beds | 3 baths | 3,223 sq.ft. |
$1,399,000 |
Airbnb cash on cash: 2.3%
|
1441 CARDINAL COURTWinter Park, FLBeautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet... |
4 beds | 6 baths | 4,066 sq.ft. |
$4,285,000 |
Airbnb cash on cash: -0.97%
|
668 OVERSPIN DRIVEWinter Park, FLOne or more photo(s) has been virtually staged. A contemporary, beautifully finished home ... |
4 beds | 3 baths | 2,509 sq.ft. |
$875,000 |
Airbnb cash on cash: 3.21%
|
1521 CHESTNUT AVENUEWinter Park, FLModern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thou... |
4 beds | 3 baths | 2,842 sq.ft. |
$1,799,900 |
Airbnb cash on cash: 0.56%
|
948 POINCIANA LANEWinter Park, FLTimeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an ... |
4 beds | 4 baths | 3,676 sq.ft. |
$3,199,000 |
Airbnb cash on cash: -0.1%
|
720 W WEBSTER AVENUEWinter Park, FLOne or more photo(s) has been virtually staged. This home can be purchased with NO INCOME ... |
3 beds | 2 baths | 1,356 sq.ft. |
$525,000 |
Airbnb cash on cash: 4.82%
|
1800 MAGNOLIA AVENUEWinter Park, FLOne or more photo(s) has been virtually staged. Experience refined living in this exquisit... |
4 beds | 3 baths | 2,431 sq.ft. |
$1,148,000 |
Airbnb cash on cash: 2.2%
|
2036 VIA TUSCANYWinter Park, FLWINTER PARK VIAâS!!! Incredible Oversized Lot is located in the âHeartâ of Winter Pa... |
3 beds | 2 baths | 2,148 sq.ft. |
$2,000,000 |
Airbnb cash on cash: 0.04%
|
1473 Berkshire AveWinter Park, FLExquisite New 2025 Luxury Home in the Heart of Winter Park - Welcome to 1473 Berkshire Ave... |
5 beds | 4 baths | 2,895 sq.ft. |
$1,499,000 |
Airbnb cash on cash: N/A
|
1636 Elizabeths WalkWinter Park, FLWelcome home to this custom 4-bedroom, 4.5-bath home in the highly desirable community of ... |
4 beds | 4 baths | 3,412 sq.ft. |
$2,195,000 |
Airbnb cash on cash: 0.56%
|
250 CORTLAND AVENUEWinter Park, FLOne or more photo(s) has been virtually staged. Introducing 250 Cortland Ave â a refined... |
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%
|
811 Overspin DrWinter Park, FL811 Overspin Dr, Orlando, FL 32789 | Single Family Residential |
2 beds | 1 baths | 749 sq.ft. |
$349,000 |
Airbnb cash on cash: 5.54%
|
1651 Westchester AveWinter Park, FLUnder contract-accepting backup offers. Welcome to this exquisite Orwin Manor Cape Cod cla... |
3 beds | 2 baths | 2,426 sq.ft. |
$1,449,000 |
Airbnb cash on cash: 1.23%
|
2560 Franklin AvenueWinter Park, FLCome see this charming 4 bed, 2 bath, 2 story home in Winter Park/ Lake Killarney location... |
4 beds | 2 baths | 1,514 sq.ft. |
$499,000 |
Airbnb cash on cash: 7.07%
|
2412 CHANTILLY AVENUEWinter Park, FLExceptional design meets refined luxury in this brand-new architectural masterpiece by DaV... |
5 beds | 7 baths | 4,506 sq.ft. |
$2,395,000 |
Airbnb cash on cash: N/A
|
1810 HOLLYWOOD AVENUEWinter Park, FLUnder Construction. Estimated completion August!! Experience modern luxury living in the h... |
4 beds | 4 baths | 2,604 sq.ft. |
$1,689,000 |
Airbnb cash on cash: 1.47%
|
1885 TEMPLE DRIVEWinter Park, FLLocated in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, thi... |
5 beds | 4 baths | 3,691 sq.ft. |
$2,265,000 |
Airbnb cash on cash: N/A
|
1782 PINE AVENUEWinter Park, FLStep into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where ... |
5 beds | 7 baths | 4,782 sq.ft. |
$4,197,000 |
Airbnb cash on cash: N/A
|
1399 ALOMA AVENUEWinter Park, FL***Price Adjustment *** Motivated Seller! Charming 1948 Winter Park Home! This 3-bedroom, ... |
3 beds | 2 baths | 1,804 sq.ft. |
$600,000 |
Airbnb cash on cash: 4.6%
|
1112 PRESERVE POINT DRIVEWinter Park, FLPresenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rar... |
5 beds | 6 baths | 6,502 sq.ft. |
$8,500,000 |
Airbnb cash on cash: N/A
|
2211 Azalea PlWinter Park, FLLuxurious waterfront estate in one of Winter Parkâs most prestigious neighborhoods, offe... |
5 beds | 7 baths | 7,278 sq.ft. |
$5,495,000 |
Airbnb cash on cash: N/A
|
Lot #21 KAROLINA AVEWinter Park, FLPre-Construction. To be built. Step into a life where charm meets convenience in the heart... |
4 beds | 4 baths | 2,662 sq.ft. |
$944,890 |
Airbnb cash on cash: 3.89%
|
1161 VALENCIA AVENUEWinter Park, FLConveniently situated near the Winter Park Country Club, this contemporary masterpiece, bu... |
4 beds | 5 baths | 4,181 sq.ft. |
$4,295,000 |
Airbnb cash on cash: -0.57%
|
607 ELLEN DRIVEWinter Park, FLNEW PRICE!!! Discover sophisticated modern living at 607 Ellen Drive, a stunning new const... |
4 beds | 5 baths | 2,812 sq.ft. |
$1,499,900 |
Airbnb cash on cash: 1.89%
|
3018 NORTHWOOD BOULEVARDWinter Park, FL"MOTIVATED SELLER" - NEED SOME CLOSING COST? RATE BUY DOWN? WE CAN HELP GET YOU INTO THIS ... |
3 beds | 2 baths | 1,761 sq.ft. |
$679,000 |
Airbnb cash on cash: 3.29%
|
560 OLOLU DRIVEWinter Park, FLNestled on the shores of private, skiable Lake Killarney, this beautifully updated and abs... |
2 beds | 2 baths | 1,086 sq.ft. |
$925,000 |
Airbnb cash on cash: 0.9%
|
1780 BRYAN AVENUEWinter Park, FLDiscover a truly unique offering in the heart of Winter Park! This property, located at 17... |
4 beds | 2 baths | 1,617 sq.ft. |
$849,000 |
Airbnb cash on cash: 3.84%
|
2503 VERSAILLES AVENUEWinter Park, FLBack on the marketâan exceptional opportunity in Winter Park. Now offered below appraise... |
5 beds | 4 baths | 4,026 sq.ft. |
$2,184,000 |
Airbnb cash on cash: N/A
|
2361 MULBRY DRIVEWinter Park, FLCasa Noir â Brand new construction custom home selected as a 2026 Parade of Homes showca... |
4 beds | 4 baths | 3,111 sq.ft. |
$2,395,000 |
Airbnb cash on cash: 0.76%
|
423 OLOLU DRIVEWinter Park, FLWelcome to this beautifully remodeled two story home in one of Winter Parkâs most desira... |
3 beds | 3 baths | 1,920 sq.ft. |
$589,000 |
Airbnb cash on cash: 4.38%
|
1523 MILLER AVENUEWinter Park, FLBRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. This 3,164 sqft home at 1523 M... |
5 beds | 4 baths | 3,164 sq.ft. |
$1,550,000 |
Airbnb cash on cash: N/A
|
1541 WESTCHESTER AVENUEWinter Park, FLSet on over half an acre in Winter Parkâs coveted Orwin Manor, this 1935 French Provinci... |
3 beds | 3 baths | 2,578 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 1.72%
|
670 WILLIAMS DRIVEWinter Park, FLThis stunning custom residence built by respected Winter Park Builder Charles Clayton blen... |
5 beds | 5 baths | 4,091 sq.ft. |
$2,995,000 |
Airbnb cash on cash: N/A
|
841 W SWOOPE AVENUEWinter Park, FLThis Winter Park property offers exceptional potential in one of the most desirable and ra... |
2 beds | 1 baths | 1,396 sq.ft. |
$499,000 |
Airbnb cash on cash: 3.46%
|
1927 ELAND AVENUEWinter Park, FL*Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rar... |
5 beds | 3 baths | 2,242 sq.ft. |
$850,000 |
Airbnb cash on cash: N/A
|
2501 LAFAYETTE AVENUEWinter Park, FLUnder Construction. GENEROUSLY APPOINTED LUXURY HOME at $1,875.000 with sound and water wa... |
4 beds | 4 baths | 2,810 sq.ft. |
$1,949,999 |
Airbnb cash on cash: 1.26%
|
1760 LEGION DRIVEWinter Park, FLWinter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando... |
4 beds | 6 baths | 4,392 sq.ft. |
$2,295,000 |
Airbnb cash on cash: 0.53%
|