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.

Investment Property for Sale in Winter Park, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
100 S VIRGINIA AVENUE #319 Winter Park, FL Under contract-accepting backup offers. Experience the best of Winter Park living in this ...	3 beds \| 3 baths \| 2,649 sq.ft.	$1,079,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 0.19% Airbnb Rental Income: $4337 Traditional Rental Income: $3419 Airbnb ROI: 0.19% Traditional ROI: 0.19%
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%
1308 S PENNSYLVANIA AVENUE #3 Winter Park, FL $25,000 below appraised value! Walk to Park Ave!! Sip coffee or tea overlooking lush Mead ...	1 beds \| 1 baths \| 823 sq.ft.	$325,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 2.2% Airbnb Rental Income: $2412 Traditional Rental Income: $1384 Airbnb ROI: 3.63% Traditional ROI: 2.2%
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%
3651 N GOLDENROD ROAD #210 Winter Park, FL beautiful Condo in of Winter Park. This spacious second-floor unit is filled with natur...	2 beds \| 2 baths \| 840 sq.ft.	$191,000	Airbnb cash on cash: 9.87% Traditional cash on cash: 4.67% Airbnb Rental Income: $3260 Traditional Rental Income: $1584 Airbnb ROI: 9.87% Traditional ROI: 4.67%
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%
1000 S SEMORAN BOULEVARD #415 Winter Park, FL NEW AC INSTALLED, PRICE REDUCTION, EXCELLENT INVESTMENT OPPORTUNITY, Great Tenant in place...	1 beds \| 1 baths \| 735 sq.ft.	$115,950	Airbnb cash on cash: 9.62% Traditional cash on cash: 6.26% Airbnb Rental Income: $2412 Traditional Rental Income: $1445 Airbnb ROI: 9.62% Traditional ROI: 6.26%
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%
150 KILLARNEY BAY COURT #5 Winter Park, FL Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfec...	2 beds \| 2 baths \| 1,140 sq.ft.	$362,500	Airbnb cash on cash: 4.55% Traditional cash on cash: 2.26% Airbnb Rental Income: $3260 Traditional Rental Income: $1751 Airbnb ROI: 4.55% Traditional ROI: 2.26%
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%
690 OSCEOLA AVENUE #209 Winter Park, FL One or more photo(s) has been virtually staged. Seller financing and lease to own options ...	2 beds \| 2 baths \| 1,148 sq.ft.	$393,800	Airbnb cash on cash: 4.83% Traditional cash on cash: 3.56% Airbnb Rental Income: $3260 Traditional Rental Income: $2057 Airbnb ROI: 4.83% Traditional ROI: 3.56%
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%
2417 PASSAMONTE DRIVE #1E Winter Park, FL Location! Location! Location! Winter Park, Top Rated Florida Zone Schools, Move-In Ready, ...	3 beds \| 3 baths \| 1,837 sq.ft.	$329,999	Airbnb cash on cash: 7.38% Traditional cash on cash: 4.13% Airbnb Rental Income: $4337 Traditional Rental Income: $2416 Airbnb ROI: 7.38% Traditional ROI: 4.13%
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%
260 KILLARNEY BAY COURT #6-6 Winter Park, FL Welcome to Killarney Bay! This beautifully updated 2-bedroom, 1-bathroom Second-floor cond...	2 beds \| 1 baths \| 1,140 sq.ft.	$345,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 1.61% Airbnb Rental Income: $3260 Traditional Rental Income: $1650 Airbnb ROI: 4.32% Traditional ROI: 1.61%
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%
1250 S DENNING DRIVE #111 Winter Park, FL Under contract-accepting backup offers. LOCATION LOCATION!! Now is your chance to own this...	2 beds \| 2 baths \| 908 sq.ft.	$259,000	Airbnb cash on cash: 4.81% Traditional cash on cash: 1.6% Airbnb Rental Income: $3260 Traditional Rental Income: $1744 Airbnb ROI: 4.81% Traditional ROI: 1.6%
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%

Real Estate investment in Winter-park, FL

There are 228 properties for sale in the city of Winter Park . The median list price in Winter Park is $587,000 and the average price per square foot is $277. In September 2025, the average monthly cash on cash return in Winter Park is 2.00%. The average monthly rental income in Winter Park is $2,387.

Winter-park, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 228 investment properties available for sale in Winter-park.

In 2025, the best neighborhood to buy investment property is Winter Park.

The ROI for Short-Term is higher than the Long-Term in Winter-park with average rental income of $4,337.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Park, FL

100 S VIRGINIA AVENUE #319

Winter Park, FL

3 beds | 3 baths | 2,649 sq.ft.

$1,079,000

Airbnb cash on cash: 0.19%

Traditional cash on cash: 0.19%

Airbnb Rental Income: $4337

Traditional Rental Income: $3419

Airbnb ROI: 0.19%

Traditional ROI: 0.19%

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