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 158 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
1820 ENGLEWOOD ROAD Winter Park, FL Under contract-accepting backup offers. Award-winning Phil Kean design on a prominent corn...	5 beds \| 6 baths \| 4,263 sq.ft.	$3,190,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.15% Airbnb Rental Income: $null Traditional Rental Income: $9012 Airbnb ROI: N/A Traditional ROI: 1.15%
1270 ARLINGTON PLACE Winter Park, FL Modern Elegance in the Heart of Winter Park! Located just a half-mile from the renowned...	3 beds \| 4 baths \| 2,964 sq.ft.	$1,700,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 0.03% Airbnb Rental Income: $4337 Traditional Rental Income: $3544 Airbnb ROI: -0.05% Traditional ROI: 0.03%
2844 SCARLET ROAD Winter Park, FL Welcome to this stunning mid-century modern beauty where timeless design meets thoughtful,...	4 beds \| 2 baths \| 1,508 sq.ft.	$519,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 3.35% Airbnb Rental Income: $5745 Traditional Rental Income: $2713 Airbnb ROI: 7.24% Traditional ROI: 3.35%
311 CORTLAND AVENUE Winter Park, FL Under contract-accepting backup offers. Location, location, location! Whether you're ready...	2 beds \| 2 baths \| 1,382 sq.ft.	$799,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 0.96% Airbnb Rental Income: $3260 Traditional Rental Income: $2160 Airbnb ROI: 1.45% Traditional ROI: 0.96%
1831 MIZELL AVENUE Winter Park, FL Stunning contemporary home in Winter Park is close to Park Avenue and all of the wonderful...	4 beds \| 4 baths \| 3,204 sq.ft.	$1,595,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 1.02% Airbnb Rental Income: $5745 Traditional Rental Income: $4611 Airbnb ROI: 1.01% Traditional ROI: 1.02%
1781 PINE AVENUE Winter Park, FL Price Reduced to sell. An exceptional custom home by award-winning Davila Homes, perfectly...	5 beds \| 5 baths \| 3,882 sq.ft.	$2,497,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.82% Airbnb Rental Income: $null Traditional Rental Income: $6454 Airbnb ROI: N/A Traditional ROI: 0.82%
715 VIA BELLA Winter Park, FL Tucked away on a quiet cul-de-sac lined with multi-million-dollar estates, this Winter Par...	5 beds \| 4 baths \| 4,328 sq.ft.	$2,369,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.44% Airbnb Rental Income: $null Traditional Rental Income: $5337 Airbnb ROI: N/A Traditional ROI: 0.44%
1761 LEGION DRIVE Winter Park, FL One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, ...	5 beds \| 6 baths \| 4,955 sq.ft.	$3,499,999	Airbnb cash on cash: N/A Traditional cash on cash: 0.93% Airbnb Rental Income: $null Traditional Rental Income: $8394 Airbnb ROI: N/A Traditional ROI: 0.93%
1018 TURNER ROAD Winter Park, FL Seller may consider buyer concessions if made in an offer \| Lakefront charm meets quiet lu...	4 beds \| 2 baths \| 2,237 sq.ft.	$890,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.11% Airbnb Rental Income: $5745 Traditional Rental Income: $3458 Airbnb ROI: 3.49% Traditional ROI: 2.11%
7602 LODGE POLE TRAIL Winter Park, FL Under contract-accepting backup offers. Nestled in desirable Arrowhead Cove, this meticulo...	3 beds \| 3 baths \| 1,906 sq.ft.	$474,998	Airbnb cash on cash: 5.68% Traditional cash on cash: 3.98% Airbnb Rental Income: $4337 Traditional Rental Income: $2667 Airbnb ROI: 5.68% Traditional ROI: 3.98%
690 S LAKEMONT AVENUE Winter Park, FL Under contract-accepting backup offers. Short Sale. Beautifully updated 4BR/3BA pool home ...	4 beds \| 3 baths \| 1,897 sq.ft.	$550,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 3.9% Airbnb Rental Income: $5745 Traditional Rental Income: $3342 Airbnb ROI: 6.35% Traditional ROI: 3.9%
1023 PRINCESS GATE BOULEVARD Winter Park, FL Under contract-accepting backup offers. VA AssumableA HIDDEN GEM nestled on Lake Deeks...	4 beds \| 3 baths \| 2,465 sq.ft.	$695,000	Airbnb cash on cash: 5.9% Traditional cash on cash: 4.87% Airbnb Rental Income: $5745 Traditional Rental Income: $3934 Airbnb ROI: 5.9% Traditional ROI: 4.87%
8065 PLEASANT PINE CIRCLE Winter Park, FL **This property qualifies for a closing cost credit up to $8,800 through the Sellerâs pr...	4 beds \| 2 baths \| 1,843 sq.ft.	$570,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 2.33% Airbnb Rental Income: $5745 Traditional Rental Income: $2364 Airbnb ROI: 6.53% Traditional ROI: 2.33%
744 CORNWALL ROAD Winter Park, FL Charming 4-Bedroom Home in Desirable Winter Park Pines Welcome to your new home in the he...	4 beds \| 2 baths \| 1,968 sq.ft.	$750,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 2.13% Airbnb Rental Income: $5745 Traditional Rental Income: $2775 Airbnb ROI: 4.73% Traditional ROI: 2.13%
2607 Lafayette Ave Winter Park, FL Welcome to 2607 Lafayette Avenueâa stunning custom home in one of Winter Parkâs most d...	4 beds \| 4 baths \| 2,770 sq.ft.	$1,095,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 1.34% Airbnb Rental Income: $5745 Traditional Rental Income: $3752 Airbnb ROI: 2.17% Traditional ROI: 1.34%
1516 PINEWOOD DRIVE Winter Park, FL PINEWOOD SUB N/9 LOT 12 BLK A Well-maintained, modest 2-1 home in College Park with c...	2 beds \| 1 baths \| 1,028 sq.ft.	$369,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 2.32% Airbnb Rental Income: $3260 Traditional Rental Income: $1698 Airbnb ROI: 4.72% Traditional ROI: 2.32%
2550 VENETIAN WAY Winter Park, FL "The richness of an artist is the fusion of influences that have shaped his life and work"...	4 beds \| 5 baths \| 4,875 sq.ft.	$2,699,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 1.93% Airbnb Rental Income: $5745 Traditional Rental Income: $8914 Airbnb ROI: 0.2% Traditional ROI: 1.93%
2812 WOODSIDE AVENUE Winter Park, FL Under contract-accepting backup offers. In the heart of the Audubon Park Garden District y...	3 beds \| 2 baths \| 1,842 sq.ft.	$625,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.72% Airbnb Rental Income: $4337 Traditional Rental Income: $2979 Airbnb ROI: 3.49% Traditional ROI: 2.72%
720 N PENNSYLVANIA AVENUE Winter Park, FL Nestled in one of Winter Parkâs most sought-after locations, this 3-bedroom, 2-bathroom ...	3 beds \| 2 baths \| 1,115 sq.ft.	$550,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 1.6% Airbnb Rental Income: $4337 Traditional Rental Income: $1903 Airbnb ROI: 4.56% Traditional ROI: 1.6%
1760 VIA VENETIA Winter Park, FL Discover unparalleled luxury in this meticulously crafted estate home, where no detail has...	4 beds \| 7 baths \| 6,242 sq.ft.	$4,995,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 0.36% Airbnb Rental Income: $5745 Traditional Rental Income: $9031 Airbnb ROI: -0.6% Traditional ROI: 0.36%
701 DENTON ROAD Winter Park, FL Seller will consider concessions. Seller Financing available. Contact us today. Welcome to...	3 beds \| 2 baths \| 2,268 sq.ft.	$575,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.37% Airbnb Rental Income: $4337 Traditional Rental Income: $3016 Airbnb ROI: 4.13% Traditional ROI: 3.37%
1400 S PENNSYLVANIA AVENUE Winter Park, FL Look 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.	$1,290,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 0.56% Airbnb Rental Income: $5745 Traditional Rental Income: $3232 Airbnb ROI: 1.7% Traditional ROI: 0.56%
208 BREWER AVENUE Winter Park, FL SELLERS ARE OFFERING $10,000 BUYER CLOSING COST CONCESSION FOR ANY BUYER WITH AN ACCEPTED ...	4 beds \| 4 baths \| 2,173 sq.ft.	$990,000	Airbnb cash on cash: 3.01% Traditional cash on cash: 3.02% Airbnb Rental Income: $5745 Traditional Rental Income: $4604 Airbnb ROI: 3.01% Traditional ROI: 3.02%
1350 LYNDALE BOULEVARD Winter Park, FL THIS HOUSE CHECKS ALL OF THE BOXES!!! Situated on a quiet one-way street in Winter Park a...	4 beds \| 5 baths \| 3,478 sq.ft.	$1,660,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 1.66% Airbnb Rental Income: $5745 Traditional Rental Income: $5782 Airbnb ROI: 0.89% Traditional ROI: 1.66%
1521 CHESTNUT AVENUE Winter Park, FL Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, buil...	4 beds \| 3 baths \| 2,843 sq.ft.	$1,899,900	Airbnb cash on cash: 0.48% Traditional cash on cash: -0.08% Airbnb Rental Income: $5745 Traditional Rental Income: $3620 Airbnb ROI: 0.48% Traditional ROI: -0.08%
1701 PALMER AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Charming Winter Park Pool Home â A Rare ...	4 beds \| 3 baths \| 2,841 sq.ft.	$1,295,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 1.56% Airbnb Rental Income: $5745 Traditional Rental Income: $4249 Airbnb ROI: 1.85% Traditional ROI: 1.56%
2381 ROXBURY ROAD Winter Park, FL Beautiful 3 Bedrooms 2 Baths in highly desired location. Established pet friendly neighbo...	3 beds \| 2 baths \| 1,645 sq.ft.	$525,000	Airbnb cash on cash: 5.41% Traditional cash on cash: 3.37% Airbnb Rental Income: $4337 Traditional Rental Income: $2423 Airbnb ROI: 5.41% Traditional ROI: 3.37%
1421 SUNSET DRIVE Winter Park, FL Under contract-accepting backup offers. BUYER GOT COLD FEET= YOUR OPPORTUNITY! Welcome to ...	3 beds \| 4 baths \| 1,672 sq.ft.	$835,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.7% Airbnb Rental Income: $4337 Traditional Rental Income: $2982 Airbnb ROI: 2.27% Traditional ROI: 1.7%
726 N PENNSYLVANIA AVENUE Winter Park, FL Welcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of moder...	3 beds \| 2 baths \| 1,167 sq.ft.	$750,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 0.97% Airbnb Rental Income: $4337 Traditional Rental Income: $1931 Airbnb ROI: 3.11% Traditional ROI: 0.97%
3490 BOUGAINVILLEA DRIVE Winter Park, FL Step into the charm and comfort of this inviting 3-bedroom, 2-bath Winter Park home, where...	3 beds \| 2 baths \| 1,461 sq.ft.	$377,500	Airbnb cash on cash: 7.65% Traditional cash on cash: 4.77% Airbnb Rental Income: $4337 Traditional Rental Income: $2405 Airbnb ROI: 7.65% Traditional ROI: 4.77%
1354 TIERRA CIRCLE Winter Park, FL Located in the highly sought-after Casa Aloma community, this charming 1960s home offers t...	4 beds \| 2 baths \| 1,827 sq.ft.	$449,900	Airbnb cash on cash: 8.85% Traditional cash on cash: 3.82% Airbnb Rental Income: $5745 Traditional Rental Income: $2479 Airbnb ROI: 8.85% Traditional ROI: 3.82%
1849 VIBURNUM LANE Winter Park, FL Nestled near the highly sought-after Winter Park area, this beautifully updated 4-bedroom,...	4 beds \| 2 baths \| 1,627 sq.ft.	$449,900	Airbnb cash on cash: 8.89% Traditional cash on cash: 3.49% Airbnb Rental Income: $5745 Traditional Rental Income: $2323 Airbnb ROI: 8.89% Traditional ROI: 3.49%
720 W WEBSTER AVENUE Winter Park, FL Discover the charm of Winter Park living in this beautifully maintained 1950s home, where ...	3 beds \| 2 baths \| 1,356 sq.ft.	$649,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 1.7% Airbnb Rental Income: $4337 Traditional Rental Income: $2200 Airbnb ROI: 3.72% Traditional ROI: 1.7%
541 W CANTON AVENUE Winter Park, FL Timeless elegance meets boutique craftsmanship at 541 W Canton Avenueâan exceptional new...	4 beds \| 4 baths \| 3,553 sq.ft.	$3,150,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 0.36% Airbnb Rental Income: $5745 Traditional Rental Income: $4490 Airbnb ROI: 0.4% Traditional ROI: 0.36%
915 GARDEN DRIVE Winter Park, FL Step into this beautifully maintained Mid-Century Modern home, nestled in the prestigious ...	3 beds \| 3 baths \| 2,456 sq.ft.	$950,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 2.76% Airbnb Rental Income: $4337 Traditional Rental Income: $4018 Airbnb ROI: 2.09% Traditional ROI: 2.76%
675 OVERSPIN DRIVE Winter Park, FL Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatil...	4 beds \| 4 baths \| 3,062 sq.ft.	$829,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 2.7% Airbnb Rental Income: $5745 Traditional Rental Income: $3980 Airbnb ROI: 3.5% Traditional ROI: 2.7%
2774 BANCHORY ROAD Winter Park, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom block ranch home in Winter Pa...	3 beds \| 2 baths \| 1,560 sq.ft.	$500,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 2.35% Airbnb Rental Income: $4337 Traditional Rental Income: $2268 Airbnb ROI: 4.83% Traditional ROI: 2.35%
1621 PURITAN, Winter Park, FL Down Payment Assistance Available! Welcome to 1621 Puritan Ave, a beautifully renovated po...	4 beds \| 2 baths \| 1,765 sq.ft.	$440,000	Airbnb cash on cash: 8.97% Traditional cash on cash: 4.37% Airbnb Rental Income: $5745 Traditional Rental Income: $2704 Airbnb ROI: 8.97% Traditional ROI: 4.37%
250 Cortland Avenue Winter Park, FL Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among mil...	3 beds \| 2 baths \| 2,114 sq.ft.	$960,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 1.77% Airbnb Rental Income: $4337 Traditional Rental Income: $2974 Airbnb ROI: 2.28% Traditional ROI: 1.77%
1150 VIA SALERNO Winter Park, FL In 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% Traditional cash on cash: 0.04% Airbnb Rental Income: $5745 Traditional Rental Income: $5577 Airbnb ROI: -0.19% Traditional ROI: 0.04%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Park, FL

1820 ENGLEWOOD ROAD

Winter Park, FL

5 beds | 6 baths | 4,263 sq.ft.

$3,190,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.15%

Airbnb Rental Income: $null

Traditional Rental Income: $9012

Airbnb ROI: N/A

Traditional ROI: 1.15%

1270 ARLINGTON PLACE

Winter Park, FL

3 beds | 4 baths | 2,964 sq.ft.

$1,700,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $4337

Traditional Rental Income: $3544

Airbnb ROI: -0.05%

Traditional ROI: 0.03%

2844 SCARLET ROAD

Winter Park, FL

4 beds | 2 baths | 1,508 sq.ft.

$519,000

Airbnb cash on cash: 7.24%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $5745

Traditional Rental Income: $2713

Airbnb ROI: 7.24%

Traditional ROI: 3.35%

311 CORTLAND AVENUE

Winter Park, FL

2 beds | 2 baths | 1,382 sq.ft.

$799,900

Airbnb cash on cash: 1.45%

Traditional cash on cash: 0.96%

Airbnb Rental Income: $3260

Traditional Rental Income: $2160

Airbnb ROI: 1.45%

Traditional ROI: 0.96%

1831 MIZELL AVENUE

Winter Park, FL

4 beds | 4 baths | 3,204 sq.ft.

$1,595,000

Airbnb cash on cash: 1.01%

Traditional cash on cash: 1.02%

Airbnb Rental Income: $5745

Traditional Rental Income: $4611

Airbnb ROI: 1.01%

Traditional ROI: 1.02%

1781 PINE AVENUE

Winter Park, FL

5 beds | 5 baths | 3,882 sq.ft.

$2,497,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.82%

Airbnb Rental Income: $null

Traditional Rental Income: $6454

Airbnb ROI: N/A

Traditional ROI: 0.82%

715 VIA BELLA

Winter Park, FL

5 beds | 4 baths | 4,328 sq.ft.

$2,369,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.44%

Airbnb Rental Income: $null

Traditional Rental Income: $5337

Airbnb ROI: N/A

Traditional ROI: 0.44%

1761 LEGION DRIVE

Winter Park, FL

5 beds | 6 baths | 4,955 sq.ft.

$3,499,999

Airbnb cash on cash: N/A

Traditional cash on cash: 0.93%

Airbnb Rental Income: $null

Traditional Rental Income: $8394

Airbnb ROI: N/A