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 151 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1751 GOODRICH AVENUE Winter Park, FL Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park...	4 beds \| 4 baths \| 2,170 sq.ft.	$1,425,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 1.11% Airbnb Rental Income: $5745 Traditional Rental Income: $3743 Airbnb ROI: 1.76% Traditional ROI: 1.11%
1649 Harmon Ave Winter Park, FL Priced to Close before the end of the year!!! New Construction Orwin Manor Area home tha...	4 beds \| 3 baths \| 3,223 sq.ft.	$1,349,900	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.57% Airbnb Rental Income: $5745 Traditional Rental Income: $4790 Airbnb ROI: 2.41% Traditional ROI: 2.57%
1441 CARDINAL COURT Winter Park, FL Beautifully 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% Traditional cash on cash: 0.07% Airbnb Rental Income: $5745 Traditional Rental Income: $8729 Airbnb ROI: -0.97% Traditional ROI: 0.07%
2333 WESTMINSTER COURT Winter Park, FL Settled on a rare double lot in the heart of Winter Park, this 4-bedroom, 2-bath home deli...	4 beds \| 2 baths \| 1,877 sq.ft.	$719,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 2.46% Airbnb Rental Income: $5745 Traditional Rental Income: $3035 Airbnb ROI: 4.79% Traditional ROI: 2.46%
948 POINCIANA LANE Winter Park, FL Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an ...	4 beds \| 4 baths \| 3,676 sq.ft.	$3,174,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 0.25% Airbnb Rental Income: $5745 Traditional Rental Income: $5609 Airbnb ROI: -0.09% Traditional ROI: 0.25%
363 N PHELPS AVENUE Winter Park, FL This light and bright, single-story, almost 3,000 square foot pool home features a split p...	4 beds \| 3 baths \| 2,871 sq.ft.	$1,249,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 1.75% Airbnb Rental Income: $5745 Traditional Rental Income: $4109 Airbnb ROI: 2.18% Traditional ROI: 1.75%
1800 MAGNOLIA AVENUE Winter Park, FL One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! NO HOA! Experience refi...	4 beds \| 3 baths \| 2,431 sq.ft.	$1,000,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 2.48% Airbnb Rental Income: $5745 Traditional Rental Income: $4421 Airbnb ROI: 2.68% Traditional ROI: 2.48%
2036 VIA TUSCANY Winter Park, FL WINTER 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% Traditional cash on cash: -0.02% Airbnb Rental Income: $4337 Traditional Rental Income: $3307 Airbnb ROI: 0.04% Traditional ROI: -0.02%
2418 EUSTON ROAD Winter Park, FL Welcome to this beautifully updated three-bedroom, two-and-a-half-bath home located in the...	3 beds \| 3 baths \| 2,228 sq.ft.	$749,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 2.7% Airbnb Rental Income: $4337 Traditional Rental Income: $3412 Airbnb ROI: 2.72% Traditional ROI: 2.7%
1473 Berkshire Ave Winter Park, FL Exquisite New 2025 Luxury Home in the Heart of Winter Park - Welcome to 1473 Berkshire Ave...	5 beds \| 4 baths \| 2,895 sq.ft.	$1,479,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.62% Airbnb Rental Income: $null Traditional Rental Income: $4216 Airbnb ROI: N/A Traditional ROI: 1.62%
250 CORTLAND AVENUE Winter Park, FL One 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% Traditional cash on cash: 2.4% Airbnb Rental Income: $4337 Traditional Rental Income: $3501 Airbnb ROI: 2.31% Traditional ROI: 2.4%
1150 VIA SALERNO Winter Park, FL In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalis...	4 beds \| 6 baths \| 3,850 sq.ft.	$4,195,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.74% Airbnb Rental Income: $5745 Traditional Rental Income: $11661 Airbnb ROI: -0.08% Traditional ROI: 1.74%
811 Overspin Dr Winter Park, FL 811 Overspin Dr, Orlando, FL 32789 \| Single Family Residential	2 beds \| 1 baths \| 749 sq.ft.	$349,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 3.03% Airbnb Rental Income: $3260 Traditional Rental Income: $1705 Airbnb ROI: 5.54% Traditional ROI: 3.03%
1651 Westchester Ave Winter Park, FL Under contract-accepting backup offers. Welcome to this exquisite Orwin Manor Cape Cod cla...	3 beds \| 2 baths \| 2,426 sq.ft.	$1,175,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 1.73% Airbnb Rental Income: $4337 Traditional Rental Income: $3402 Airbnb ROI: 1.75% Traditional ROI: 1.73%
2560 Franklin Avenue Winter Park, FL Come 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% Traditional cash on cash: 3.26% Airbnb Rental Income: $5745 Traditional Rental Income: $2821 Airbnb ROI: 7.07% Traditional ROI: 3.26%
1707 Harmon Ave Winter Park, FL 1707 Harmon Ave, Orlando, FL 32789 \| Single Family Residential	3 beds \| 2 baths \| 1,669 sq.ft.	$695,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 1.04% Airbnb Rental Income: $4337 Traditional Rental Income: $1986 Airbnb ROI: 3.26% Traditional ROI: 1.04%
1981 BLUE RIDGE ROAD Winter Park, FL Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring ...	4 beds \| 2 baths \| 2,750 sq.ft.	$1,150,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.23% Airbnb Rental Income: $5745 Traditional Rental Income: $3522 Airbnb ROI: 2.24% Traditional ROI: 1.23%
1981 Blue Ridge Rd Winter Park, FL 1981 Blue Ridge Rd, Orlando, FL 32789 \| Single Family Residential	4 beds \| 2 baths \| 2,750 sq.ft.	$1,150,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 1.14% Airbnb Rental Income: $5745 Traditional Rental Income: $3328 Airbnb ROI: 2.33% Traditional ROI: 1.14%
1885 TEMPLE DRIVE Winter Park, FL Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, thi...	5 beds \| 4 baths \| 3,691 sq.ft.	$2,225,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.86% Airbnb Rental Income: $null Traditional Rental Income: $6564 Airbnb ROI: N/A Traditional ROI: 1.86%
450 LAKEWOOD DRIVE Winter Park, FL Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Flo...	5 beds \| 6 baths \| 4,572 sq.ft.	$2,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.5% Airbnb Rental Income: $null Traditional Rental Income: $9247 Airbnb ROI: N/A Traditional ROI: 2.5%
1782 PINE AVENUE Winter Park, FL (HUGE PRICE REDUCTION & NEWLY ENHANCED REAR LANDSCAPING ADDED FOR EXCEPTIONAL PRIVACY AND ...	5 beds \| 7 baths \| 4,782 sq.ft.	$3,875,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.25% Airbnb Rental Income: $null Traditional Rental Income: $12218 Airbnb ROI: N/A Traditional ROI: 2.25%
2211 Azalea Pl Winter Park, FL Luxurious waterfront estate in one of Winter Parkâs most prestigious neighborhoods, offe...	5 beds \| 7 baths \| 7,278 sq.ft.	$5,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.16% Airbnb Rental Income: $null Traditional Rental Income: $13911 Airbnb ROI: N/A Traditional ROI: 1.16%
Lot #21 KAROLINA AVE Winter Park, FL Pre-Construction. To be built. This is your final opportunity to build a custom home in on...	4 beds \| 4 baths \| 2,662 sq.ft.	$944,890	Airbnb cash on cash: 3.89% Traditional cash on cash: 3.4% Airbnb Rental Income: $5745 Traditional Rental Income: $4170 Airbnb ROI: 3.89% Traditional ROI: 3.4%
1161 VALENCIA AVENUE Winter Park, FL Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, bu...	4 beds \| 5 baths \| 4,181 sq.ft.	$3,995,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 0.44% Airbnb Rental Income: $5745 Traditional Rental Income: $8217 Airbnb ROI: -0.54% Traditional ROI: 0.44%
607 ELLEN DRIVE Winter Park, FL NEW PRICE!!! Discover sophisticated modern living at 607 Ellen Drive, a stunning new const...	4 beds \| 5 baths \| 2,812 sq.ft.	$1,449,900	Airbnb cash on cash: 1.99% Traditional cash on cash: 3.28% Airbnb Rental Income: $5745 Traditional Rental Income: $6330 Airbnb ROI: 1.99% Traditional ROI: 3.28%
560 OLOLU DRIVE Winter Park, FL Nestled 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% Traditional cash on cash: 1.02% Airbnb Rental Income: $3260 Traditional Rental Income: $2632 Airbnb ROI: 0.9% Traditional ROI: 1.02%
1780 BRYAN AVENUE Winter Park, FL Build your dream home in one of Winter Parkâs most desirable locations. This 66.6â x 1...	4 beds \| 2 baths \| 1,617 sq.ft.	$849,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 2.01% Airbnb Rental Income: $5745 Traditional Rental Income: $3153 Airbnb ROI: 3.84% Traditional ROI: 2.01%
2361 Mulbry Dr Winter Park, FL Newly completed and selected as a showcase residence in the 2026 Parade of Homes, Casa Noi...	4 beds \| 4 baths \| 3,130 sq.ft.	$2,289,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 1.45% Airbnb Rental Income: $5745 Traditional Rental Income: $5896 Airbnb ROI: 0.84% Traditional ROI: 1.45%
423 OLOLU DRIVE Winter Park, FL PRICE IMPROVEMENT! Welcome to this beautifully remodeled two story home in one of Winter P...	3 beds \| 3 baths \| 1,920 sq.ft.	$549,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 3.9% Airbnb Rental Income: $4337 Traditional Rental Income: $2979 Airbnb ROI: 4.77% Traditional ROI: 3.9%
1523 MILLER AVENUE Winter Park, FL BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. This 3,164 sqft home at 1523 M...	5 beds \| 4 baths \| 3,164 sq.ft.	$1,499,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $5740 Airbnb ROI: N/A Traditional ROI: 2.81%
1541 WESTCHESTER AVENUE Winter Park, FL Set on over half an acre in Winter Parkâs coveted Orwin Manor, this 1935 French Provinci...	3 beds \| 3 baths \| 2,578 sq.ft.	$1,030,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 3.2% Airbnb Rental Income: $4337 Traditional Rental Income: $4668 Airbnb ROI: 1.91% Traditional ROI: 3.2%
2661 Via Tuscany Winter Park, FL Set in the perfect Winter Park location, within exclusive Via Tuscany, this unique, RESILI...	4 beds \| 5 baths \| 4,636 sq.ft.	$6,888,888	Airbnb cash on cash: -0.32% Traditional cash on cash: 0.32% Airbnb Rental Income: $5745 Traditional Rental Income: $8679 Airbnb ROI: -0.32% Traditional ROI: 0.32%
1927 ELAND AVENUE Winter 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.	$825,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.99% Airbnb Rental Income: $null Traditional Rental Income: $4225 Airbnb ROI: N/A Traditional ROI: 3.99%
2501 LAFAYETTE AVENUE Winter Park, FL Under 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% Traditional cash on cash: 1.79% Airbnb Rental Income: $5745 Traditional Rental Income: $5556 Airbnb ROI: 1.26% Traditional ROI: 1.79%
1760 LEGION DRIVE Winter Park, FL Winter 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% Traditional cash on cash: 2.64% Airbnb Rental Income: $5745 Traditional Rental Income: $9097 Airbnb ROI: 0.53% Traditional ROI: 2.64%
1354 INDIANA AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Fabulous location in Winter Park! Complete...	3 beds \| 2 baths \| 1,269 sq.ft.	$589,900	Airbnb cash on cash: 4.15% Traditional cash on cash: 2.93% Airbnb Rental Income: $4337 Traditional Rental Income: $2752 Airbnb ROI: 4.15% Traditional ROI: 2.93%
2501 WINTER PARK ROAD Winter Park, FL PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUST...	5 beds \| 4 baths \| 3,304 sq.ft.	$1,649,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.49% Airbnb Rental Income: $null Traditional Rental Income: $4910 Airbnb ROI: N/A Traditional ROI: 1.49%
2779 SANBINA STREET Winter Park, FL Rare opportunity in the heart of 32789 â priced under $500K, this 3-bedroom, 2-bathroom ...	3 beds \| 2 baths \| 1,405 sq.ft.	$429,000	Airbnb cash on cash: 5.99% Traditional cash on cash: 4.24% Airbnb Rental Income: $4337 Traditional Rental Income: $2723 Airbnb ROI: 5.99% Traditional ROI: 4.24%
1903 N PARK AVENUE Winter Park, FL Completed in 2020, this beautifully designed contemporary residence on North Park Avenue o...	4 beds \| 4 baths \| 2,807 sq.ft.	$1,695,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 1.21% Airbnb Rental Income: $5745 Traditional Rental Income: $5163 Airbnb ROI: 0.85% Traditional ROI: 1.21%
405 Lake Fair Ln Winter Park, FL One or more photo(s) has been virtually staged. Fully rebuilt, not just renovated. This Wi...	3 beds \| 2 baths \| 1,491 sq.ft.	$455,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 4.82% Airbnb Rental Income: $4337 Traditional Rental Income: $2697 Airbnb ROI: 6.53% Traditional ROI: 4.82%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Park, FL

1751 GOODRICH AVENUE

Winter Park, FL

4 beds | 4 baths | 2,170 sq.ft.

$1,425,000

Airbnb cash on cash: 1.76%

Traditional cash on cash: 1.11%

Airbnb Rental Income: $5745

Traditional Rental Income: $3743

Airbnb ROI: 1.76%

Traditional ROI: 1.11%

1649 Harmon Ave

Winter Park, FL

4 beds | 3 baths | 3,223 sq.ft.

$1,349,900

Airbnb cash on cash: 2.41%

Traditional cash on cash: 2.57%

Airbnb Rental Income: $5745

Traditional Rental Income: $4790

Airbnb ROI: 2.41%

Traditional ROI: 2.57%

1441 CARDINAL COURT

Winter Park, FL

4 beds | 6 baths | 4,066 sq.ft.

$4,285,000

Airbnb cash on cash: -0.97%

Traditional cash on cash: 0.07%

Airbnb Rental Income: $5745

Traditional Rental Income: $8729

Airbnb ROI: -0.97%

Traditional ROI: 0.07%

2333 WESTMINSTER COURT

Winter Park, FL

4 beds | 2 baths | 1,877 sq.ft.

$719,000

Airbnb cash on cash: 4.79%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $5745

Traditional Rental Income: $3035

Airbnb ROI: 4.79%

Traditional ROI: 2.46%

948 POINCIANA LANE

Winter Park, FL

4 beds | 4 baths | 3,676 sq.ft.

$3,174,000

Airbnb cash on cash: -0.09%

Traditional cash on cash: 0.25%

Airbnb Rental Income: $5745

Traditional Rental Income: $5609

Airbnb ROI: -0.09%

Traditional ROI: 0.25%

363 N PHELPS AVENUE

Winter Park, FL

4 beds | 3 baths | 2,871 sq.ft.

$1,249,000

Airbnb cash on cash: 2.18%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $5745

Traditional Rental Income: $4109

Airbnb ROI: 2.18%

Traditional ROI: 1.75%

1800 MAGNOLIA AVENUE

Winter Park, FL

4 beds | 3 baths | 2,431 sq.ft.

$1,000,000

Airbnb cash on cash: 2.68%

Traditional cash on cash: 2.48%

Airbnb Rental Income: $5745

Traditional Rental Income: $4421

Airbnb ROI: 2.68%

Traditional ROI: 2.48%

2036 VIA TUSCANY

Winter Park, FL

3 beds | 2 baths | 2,148 sq.ft.

$2,000,000

Airbnb cash on cash: 0.04%

Traditional cash on cash: -0.02%

Airbnb Rental Income: $4337

Traditional Rental Income: $3307

Airbnb ROI: 0.04%