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 211 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 Ave Winter Park, FL Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park...	4 beds \| 3 baths \| 2,170 sq.ft.	$1,380,000	Airbnb cash on cash: 2.12% Traditional cash on cash: 1.18% Airbnb Rental Income: $6159 Traditional Rental Income: $3743 Airbnb ROI: 2.12% Traditional ROI: 1.18%
437 N Capen Ave Winter Park, FL Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Wi...	3 beds \| 2 baths \| 1,904 sq.ft.	$849,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.2% Airbnb Rental Income: $2174 Traditional Rental Income: $2595 Airbnb ROI: -1.02% Traditional ROI: 0.2%
1840 Bryan Ave Winter Park, FL Welcome to modern luxury in the heart of Winter Park! This custom 2014-built estate rests ...	4 beds \| 3 baths \| 3,727 sq.ft.	$1,725,000	Airbnb cash on cash: 0.9% Traditional cash on cash: -0.32% Airbnb Rental Income: $6159 Traditional Rental Income: $2986 Airbnb ROI: 0.9% Traditional ROI: -0.32%
1441 Cardinal Ct Winter Park, FL Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet...	4 beds \| 5 baths \| 4,066 sq.ft.	$3,995,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.14% Airbnb Rental Income: $6159 Traditional Rental Income: $8729 Airbnb ROI: -0.88% Traditional ROI: 0.14%
900 Carver St Winter Park, FL Completely Remodeled 2026 \| Single-Story \| Prime Location \| Dual Suites \| The redesigned k...	3 beds \| 3 baths \| 1,794 sq.ft.	$689,000	Airbnb cash on cash: 3.94% Traditional cash on cash: 3.31% Airbnb Rental Income: $4249 Traditional Rental Income: $2945 Airbnb ROI: 3.94% Traditional ROI: 3.31%
2418 Euston Rd Winter Park, FL Welcome to this beautifully updated three-bedroom, two-and-a-half-bath home located in the...	3 beds \| 2 baths \| 2,228 sq.ft.	$624,444	Airbnb cash on cash: 0.3% Traditional cash on cash: 3.21% Airbnb Rental Income: $2174 Traditional Rental Income: $3412 Airbnb ROI: 0.3% Traditional ROI: 3.21%
2430 Chantilly Ave Winter Park, FL Architecture, design, and function come together with remarkable intention in this custom ...	4 beds \| 4 baths \| 2,916 sq.ft.	$1,598,000	Airbnb cash on cash: 1.96% Traditional cash on cash: -0.18% Airbnb Rental Income: $6159 Traditional Rental Income: $1768 Airbnb ROI: 1.96% Traditional ROI: -0.18%
2228 Azalea Pl Winter Park, FL This elegant transitional French Provincial residence was the feature home in the Orlando ...	5 beds \| 5 baths \| 5,152 sq.ft.	$5,600,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.12% Airbnb Rental Income: $null Traditional Rental Income: $7147 Airbnb ROI: N/A Traditional ROI: -0.12%
708 BALMORAL Road Winter Park, FL A rare elevated corner lot in the heart of Winter Park - walkable to Park Avenue's boutiqu...	4 beds \| 3 baths \| 2,786 sq.ft.	$1,590,000	Airbnb cash on cash: 1.88% Traditional cash on cash: -0.02% Airbnb Rental Income: $6159 Traditional Rental Income: $2127 Airbnb ROI: 1.88% Traditional ROI: -0.02%
450 Lakewood Dr Winter Park, FL Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Flor...	5 beds \| 4 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%
3006 Northwood Blvd Winter Park, FL Reinvented from the ground up for modern living while honoring its 1953 mid-century modern...	4 beds \| 3 baths \| 2,075 sq.ft.	$925,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 1.33% Airbnb Rental Income: $6159 Traditional Rental Income: $2644 Airbnb ROI: 3.8% Traditional ROI: 1.33%
1550 Palm Ave Winter Park, FL Under Construction. LUXURY NEW CONSTRUCTION IN WINTER PARK'S HIGHLY SOUGHT-AFTER TREE STRE...	4 beds \| 3 baths \| 2,706 sq.ft.	$1,829,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 0.3% Airbnb Rental Income: $6159 Traditional Rental Income: $3021 Airbnb ROI: 1.43% Traditional ROI: 0.3%
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 \| 2 baths \| 2,662 sq.ft.	$918,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 3.53% Airbnb Rental Income: $6159 Traditional Rental Income: $4170 Airbnb ROI: 4.44% Traditional ROI: 3.53%
2308 Mulbry Dr Winter Park, FL Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balanc...	4 beds \| 3 baths \| 2,530 sq.ft.	$1,699,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 0.24% Airbnb Rental Income: $6159 Traditional Rental Income: $2401 Airbnb ROI: 1.86% Traditional ROI: 0.24%
560 Ololu Dr 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.	$899,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 1.08% Airbnb Rental Income: $2157 Traditional Rental Income: $2632 Airbnb ROI: -0.14% Traditional ROI: 1.08%
1523 Miller Ave Winter Park, FL BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. 2-year builders' warranty! Thi...	5 beds \| 4 baths \| 3,164 sq.ft.	$1,399,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.09% Airbnb Rental Income: $null Traditional Rental Income: $5740 Airbnb ROI: N/A Traditional ROI: 3.09%
1927 Eland Ave 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.	$820,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $4225 Airbnb ROI: N/A Traditional ROI: 4.02%
1354 Indiana Ave Winter Park, FL Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to botto...	3 beds \| 2 baths \| 1,269 sq.ft.	$574,900	Airbnb cash on cash: 0.92% Traditional cash on cash: 3.03% Airbnb Rental Income: $2174 Traditional Rental Income: $2752 Airbnb ROI: 0.92% Traditional ROI: 3.03%
240 N Phelps Ave Winter Park, FL A striking expression of modern luxury, this brand-new residence offers nearly 3,000 squar...	5 beds \| 4 baths \| 2,889 sq.ft.	$2,050,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.26% Airbnb Rental Income: $null Traditional Rental Income: $3101 Airbnb ROI: N/A Traditional ROI: 0.26%
1903 N Park Ave Winter Park, FL Completed in 2020, this beautifully designed contemporary residence on North Park Avenue o...	4 beds \| 4 baths \| 2,807 sq.ft.	$1,649,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 1.24% Airbnb Rental Income: $6159 Traditional Rental Income: $5163 Airbnb ROI: 1.1% Traditional ROI: 1.24%
1870 Staunton Ave Winter Park, FL Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residen...	4 beds \| 3 baths \| 2,525 sq.ft.	$1,250,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 3.56% Airbnb Rental Income: $6159 Traditional Rental Income: $5508 Airbnb ROI: 3.07% Traditional ROI: 3.56%
950 Hanover Ave Winter Park, FL Welcome home to your peaceful retreat tucked away near the end of a quiet street with view...	3 beds \| 2 baths \| 1,606 sq.ft.	$439,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 3.71% Airbnb Rental Income: $2174 Traditional Rental Income: $2358 Airbnb ROI: 1.92% Traditional ROI: 3.71%
723 Symonds Ave Winter Park, FL Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments fr...	4 beds \| 4 baths \| 3,065 sq.ft.	$1,700,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 0.38% Airbnb Rental Income: $6159 Traditional Rental Income: $3746 Airbnb ROI: 1.14% Traditional ROI: 0.38%
1571 Woodland Ave Winter Park, FL Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Wint...	5 beds \| 6 baths \| 7,397 sq.ft.	$6,000,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.09% Airbnb Rental Income: $null Traditional Rental Income: $9026 Airbnb ROI: N/A Traditional ROI: 0.09%
338 Blue Heron Dr Winter Park, FL Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Cen...	3 beds \| 3 baths \| 2,017 sq.ft.	$840,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 2.98% Airbnb Rental Income: $2174 Traditional Rental Income: $3822 Airbnb ROI: 0.17% Traditional ROI: 2.98%
2831 Mulford Ave Winter Park, FL Just Reduced by $20,000! This is your chance to own a beautifully updated Winter Park home...	4 beds \| 2 baths \| 1,647 sq.ft.	$655,000	Airbnb cash on cash: 6.69% Traditional cash on cash: 3.19% Airbnb Rental Income: $6159 Traditional Rental Income: $2874 Airbnb ROI: 6.69% Traditional ROI: 3.19%
1562 Arbor Park Dr Winter Park, FL Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-ba...	4 beds \| 2 baths \| 1,899 sq.ft.	$775,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 2.54% Airbnb Rental Income: $6159 Traditional Rental Income: $3552 Airbnb ROI: 4.47% Traditional ROI: 2.54%
1003 Lake Bell Dr Winter Park, FL Rare Waterfront Opportunity in Winter Park! Discover your own slice of Florida paradise wi...	3 beds \| 2 baths \| 1,837 sq.ft.	$549,900	Airbnb cash on cash: 1.59% Traditional cash on cash: 4.05% Airbnb Rental Income: $2174 Traditional Rental Income: $2889 Airbnb ROI: 1.59% Traditional ROI: 4.05%
2667 Cochise Trl Winter Park, FL A MUST SEE BEAUTIFUL WELL MAINTAINED POOL HOME by ORIGINAL OWNERS in SOUGHT AFTER WINTER P...	4 beds \| 3 baths \| 2,868 sq.ft.	$985,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 2.52% Airbnb Rental Income: $6159 Traditional Rental Income: $3793 Airbnb ROI: 3.76% Traditional ROI: 2.52%
1871 Bryan Ave Winter Park, FL Opportunity meets location at 1871 Bryan Avenue, a well-positioned Winter Park property of...	3 beds \| 2 baths \| 1,232 sq.ft.	$625,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 1.64% Airbnb Rental Income: $2174 Traditional Rental Income: $1941 Airbnb ROI: 1.09% Traditional ROI: 1.64%
1431 Palm Ave Winter Park, FL Welcome to this beautifully maintained 1960s home nestled in one of Winter Park's desirabl...	2 beds \| 2 baths \| 1,540 sq.ft.	$825,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 1.48% Airbnb Rental Income: $2157 Traditional Rental Income: $2178 Airbnb ROI: 0.74% Traditional ROI: 1.48%
276 Detmar Dr Winter Park, FL Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends mod...	4 beds \| 5 baths \| 4,202 sq.ft.	$3,600,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -0.07% Airbnb Rental Income: $6159 Traditional Rental Income: $6549 Airbnb ROI: -0.55% Traditional ROI: -0.07%
1621 Chestnut Ave Winter Park, FL Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted "T...	3 beds \| 2 baths \| 2,022 sq.ft.	$899,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 2.01% Airbnb Rental Income: $2174 Traditional Rental Income: $2916 Airbnb ROI: 0.46% Traditional ROI: 2.01%
471 Holt Ave Winter Park, FL Exceptional Winter Park Opportunity with In-Law Suite & Income Potential Discover the oppo...	4 beds \| 3 baths \| 2,528 sq.ft.	$975,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 2.07% Airbnb Rental Income: $6159 Traditional Rental Income: $3733 Airbnb ROI: 3.38% Traditional ROI: 2.07%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Park, FL

1751 Goodrich Ave

Winter Park, FL

4 beds | 3 baths | 2,170 sq.ft.

$1,380,000

Airbnb cash on cash: 2.12%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $6159

Traditional Rental Income: $3743

Airbnb ROI: 2.12%

Traditional ROI: 1.18%

437 N Capen Ave

Winter Park, FL

3 beds | 2 baths | 1,904 sq.ft.

$849,000

Airbnb cash on cash: -1.02%

Traditional cash on cash: 0.2%

Airbnb Rental Income: $2174

Traditional Rental Income: $2595

Airbnb ROI: -1.02%

Traditional ROI: 0.2%

1840 Bryan Ave

Winter Park, FL

4 beds | 3 baths | 3,727 sq.ft.

$1,725,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: -0.32%

Airbnb Rental Income: $6159

Traditional Rental Income: $2986

Airbnb ROI: 0.9%

Traditional ROI: -0.32%

1441 Cardinal Ct

Winter Park, FL

4 beds | 5 baths | 4,066 sq.ft.

$3,995,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $6159

Traditional Rental Income: $8729

Airbnb ROI: -0.88%

Traditional ROI: 0.14%

900 Carver St

Winter Park, FL

3 beds | 3 baths | 1,794 sq.ft.

$689,000

Airbnb cash on cash: 3.94%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $4249

Traditional Rental Income: $2945

Airbnb ROI: 3.94%

Traditional ROI: 3.31%

2418 Euston Rd

Winter Park, FL

3 beds | 2 baths | 2,228 sq.ft.

$624,444

Airbnb cash on cash: 0.3%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $2174

Traditional Rental Income: $3412

Airbnb ROI: 0.3%

Traditional ROI: 3.21%

2430 Chantilly Ave

Winter Park, FL

4 beds | 4 baths | 2,916 sq.ft.

$1,598,000

Airbnb cash on cash: 1.96%

Traditional cash on cash: -0.18%

Airbnb Rental Income: $6159

Traditional Rental Income: $1768

Airbnb ROI: 1.96%

Traditional ROI: -0.18%

2228 Azalea Pl

Winter Park, FL

5 beds | 5 baths | 5,152 sq.ft.

$5,600,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.12%

Airbnb Rental Income: $null

Traditional Rental Income: $7147

Airbnb ROI: N/A