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.

Multi Family for Sale in Winter Park, FL

Search for Multi Family for Sale in Winter Park, Florida. Browse all of Mashvisor’s Multi Family listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 8 Multi Family 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
726/720 N PENNSYLVANIA Avenue Winter Park, FL Opportunities like this don't come around often, this is currently the only duplex availab...	6 beds \| 4 baths \| 2,282 sq.ft.	$1,185,999	Airbnb cash on cash: -0.06% Traditional cash on cash: 3.5% Airbnb Rental Income: $2157 Traditional Rental Income: $5535 Airbnb ROI: -0.06% Traditional ROI: 3.5%
901 HARMON Avenue Winter Park, FL Rare opportunity to own a charming Duplex on a corner lot in the heart of Winter Park! Loc...	2 beds \| 2 baths \| 1,277 sq.ft.	$650,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 1.37% Airbnb Rental Income: $2157 Traditional Rental Income: $2065 Airbnb ROI: 0.62% Traditional ROI: 1.37%
2183 Crandon Ave Winter Park, FL 2183 Crandon Ave, Winter Park, FL 32789 \| Multi Family	4 beds \| N/A baths \| 1,200 sq.ft.	$499,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 1.67% Airbnb Rental Income: $1793 Traditional Rental Income: $1753 Airbnb ROI: 0.71% Traditional ROI: 1.67%
1016 ARAGON Avenue Winter Park, FL This "Investment Opportunity" Duplex is centrally located on a quiet tree lined, brick str...	4 beds \| 4 baths \| 1,840 sq.ft.	$660,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 4.01% Airbnb Rental Income: $2157 Traditional Rental Income: $3386 Airbnb ROI: 1.13% Traditional ROI: 4.01%
5781 SHALE Court Winter Park, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	2 beds \| 2 baths \| 1,086 sq.ft.	$300,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 3.95% Airbnb Rental Income: $2174 Traditional Rental Income: $1688 Airbnb ROI: 3.72% Traditional ROI: 3.95%
2712 TORTOISE CV Winter Park, FL Why Rent WHEN you can own this 2 bedroom 1 bath single car garage on this 1/2 duplex with ...	2 beds \| 1 baths \| 924 sq.ft.	$235,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 4.36% Airbnb Rental Income: $2174 Traditional Rental Income: $1513 Airbnb ROI: 4.85% Traditional ROI: 4.36%
3302 ROYAL Street Winter Park, FL Come see this 3 bedroom 2 bath split plan home. All tile throughout home. Granite kitchen ...	3 beds \| 2 baths \| 1,197 sq.ft.	$289,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $1911 Airbnb ROI: N/A Traditional ROI: 4.54%
5444 PEACO Place Winter Park, FL WELCOME HOME!!! This CHARMING refreshed WINTER PARK GEM 2/2 is ready for YOU! Roof is 2024...	2 beds \| 2 baths \| 924 sq.ft.	$250,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 4.7% Airbnb Rental Income: $2174 Traditional Rental Income: $1686 Airbnb ROI: 4.43% Traditional ROI: 4.7%

Your search for investment property begins and ends here

Multi Family for Sale in Winter Park, FL

726/720 N PENNSYLVANIA Avenue

Winter Park, FL

6 beds | 4 baths | 2,282 sq.ft.

$1,185,999

Airbnb cash on cash: -0.06%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $2157

Traditional Rental Income: $5535

Airbnb ROI: -0.06%

Traditional ROI: 3.5%

901 HARMON Avenue

Winter Park, FL

2 beds | 2 baths | 1,277 sq.ft.

$650,000

Airbnb cash on cash: 0.62%

Traditional cash on cash: 1.37%

Airbnb Rental Income: $2157

Traditional Rental Income: $2065

Airbnb ROI: 0.62%

Traditional ROI: 1.37%

2183 Crandon Ave

Winter Park, FL

4 beds | N/A baths | 1,200 sq.ft.

$499,000

Airbnb cash on cash: 0.71%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $1793

Traditional Rental Income: $1753

Airbnb ROI: 0.71%

Traditional ROI: 1.67%

1016 ARAGON Avenue

Winter Park, FL

4 beds | 4 baths | 1,840 sq.ft.

$660,000

Airbnb cash on cash: 1.13%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $2157

Traditional Rental Income: $3386

Airbnb ROI: 1.13%

Traditional ROI: 4.01%

5781 SHALE Court

Winter Park, FL

2 beds | 2 baths | 1,086 sq.ft.

$300,000

Airbnb cash on cash: 3.72%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $2174

Traditional Rental Income: $1688

Airbnb ROI: 3.72%

Traditional ROI: 3.95%

2712 TORTOISE CV

Winter Park, FL

2 beds | 1 baths | 924 sq.ft.

$235,000

Airbnb cash on cash: 4.85%

Traditional cash on cash: 4.36%

Airbnb Rental Income: $2174

Traditional Rental Income: $1513

Airbnb ROI: 4.85%

Traditional ROI: 4.36%

3302 ROYAL Street

Winter Park, FL

3 beds | 2 baths | 1,197 sq.ft.

$289,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.54%

Airbnb Rental Income: $null

Traditional Rental Income: $1911

Airbnb ROI: N/A

Traditional ROI: 4.54%

5444 PEACO Place

Winter Park, FL

2 beds | 2 baths | 924 sq.ft.

$250,000

Airbnb cash on cash: 4.43%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $2174

Traditional Rental Income: $1686

Airbnb ROI: 4.43%