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
740 BAFFIE AVENUE Winter Park, FL Under contract-accepting backup offers. Welcome to this fully remodeled, move in ready hom...	3 beds \| 2 baths \| 1,456 sq.ft.	$420,000	Airbnb cash on cash: 6.22% Traditional cash on cash: 3.18% Airbnb Rental Income: $4337 Traditional Rental Income: $2229 Airbnb ROI: 6.22% Traditional ROI: 3.18%
1018 TURNER ROAD Winter Park, FL Under contract-accepting backup offers. Seller may consider buyer concessions if made in a...	3 beds \| 2 baths \| 2,237 sq.ft.	$835,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 2.32% Airbnb Rental Income: $4337 Traditional Rental Income: $3458 Airbnb ROI: 2.27% Traditional ROI: 2.32%
1324 INDIANA AVENUE Winter Park, FL Charming two story bungalow built in 1935. Timeless character meets modern comfort in this...	4 beds \| 3 baths \| 1,692 sq.ft.	$745,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 1.95% Airbnb Rental Income: $5745 Traditional Rental Income: $2954 Airbnb ROI: 4.32% Traditional ROI: 1.95%
701 DENTON ROAD Winter Park, FL Motivated Seller! Contact us today. Welcome to this beautifully upgraded home in Winter Pa...	3 beds \| 2 baths \| 2,268 sq.ft.	$565,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 3.44% Airbnb Rental Income: $4337 Traditional Rental Income: $3016 Airbnb ROI: 4.22% Traditional ROI: 3.44%
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.	$1,250,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 0.61% Airbnb Rental Income: $5745 Traditional Rental Income: $3232 Airbnb ROI: 1.79% Traditional ROI: 0.61%
208 BREWER AVENUE Winter Park, FL Welcome to this beautifully updated 4-bedroom, 3.5-bath Craftsman-style home, offering jus...	4 beds \| 4 baths \| 2,173 sq.ft.	$925,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 3.3% Airbnb Rental Income: $5745 Traditional Rental Income: $4604 Airbnb ROI: 3.29% Traditional ROI: 3.3%
2811 EASTERN PARKWAY Winter Park, FL Under contract-accepting backup offers. Mid-Century Modern architecture meets modern comfo...	3 beds \| 2 baths \| 1,433 sq.ft.	$625,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 3% Airbnb Rental Income: $4337 Traditional Rental Income: $2945 Airbnb ROI: 3.82% Traditional ROI: 3%
150 Killarney Bay Ct #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.	$345,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 1.93% Airbnb Rental Income: $3260 Traditional Rental Income: $1751 Airbnb ROI: 4.33% Traditional ROI: 1.93%
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%
4591 WHIMBREL PLACE Winter Park, FL Charming home nestled in a small, quaint community on spacious, custom-home lots. This wel...	3 beds \| 2 baths \| 1,942 sq.ft.	$490,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 3.55% Airbnb Rental Income: $4337 Traditional Rental Income: $2410 Airbnb ROI: 5.77% Traditional ROI: 3.55%
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.	$695,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 1.13% Airbnb Rental Income: $4337 Traditional Rental Income: $1931 Airbnb ROI: 3.43% Traditional ROI: 1.13%
875 W LYMAN AVENUE Winter Park, FL Don't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 ...	2 beds \| 2 baths \| 760 sq.ft.	$425,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 2.7% Airbnb Rental Income: $3260 Traditional Rental Income: $1899 Airbnb ROI: 4.28% Traditional ROI: 2.7%
2217 Sussex Rd Winter Park, FL 4 BEDROOMS with OFFICE POOL HOME. MOTIVATED SELLERS. MOVE IN READY! THIS HOME WILL NOT L...	4 beds \| 2 baths \| 2,092 sq.ft.	$530,000	Airbnb cash on cash: 7.17% Traditional cash on cash: 3.83% Airbnb Rental Income: $5745 Traditional Rental Income: $2942 Airbnb ROI: 7.17% Traditional ROI: 3.83%
311 E MORSE BOULEVARD #7-2 Winter Park, FL One or more photo(s) has been virtually staged. Enjoy sunrise views over Lake Osceola from...	1 beds \| 1 baths \| 900 sq.ft.	$399,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 0.29% Airbnb Rental Income: $2412 Traditional Rental Income: $2027 Airbnb ROI: -0.26% Traditional ROI: 0.29%
1621 PURITAN, Winter Park, FL Under contract-accepting backup offers. Down Payment Assistance Available! Welcome to 1621...	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%
3019 Antique Oaks Cir #124 Winter Park, FL Investors and Owner Occupied Welcome! Investors start your portfolio of properties with mo...	1 beds \| 1 baths \| 749 sq.ft.	$155,000	Airbnb cash on cash: 7.12% Traditional cash on cash: 6.07% Airbnb Rental Income: $2412 Traditional Rental Income: $1666 Airbnb ROI: 7.12% Traditional ROI: 6.07%
2189 SUSSEX ROAD Winter Park, FL One or more photo(s) has been virtually staged. One or more photos have been virtually sta...	4 beds \| 3 baths \| 1,776 sq.ft.	$535,000	Airbnb cash on cash: 7.11% Traditional cash on cash: 3.38% Airbnb Rental Income: $5745 Traditional Rental Income: $2731 Airbnb ROI: 7.11% Traditional ROI: 3.38%
525 S LAKEMONT AVENUE Winter Park, FL Under Construction. Winter Park Luxury Awaits You! Welcome to your dream homeâa stunn...	4 beds \| 4 baths \| 3,330 sq.ft.	$2,350,000	Airbnb cash on cash: 0.77% Traditional cash on cash: -0.07% Airbnb Rental Income: $5745 Traditional Rental Income: $2773 Airbnb ROI: 0.77% Traditional ROI: -0.07%
1174 WILDMEADOW RUN Winter Park, FL Welcome to Hawks Crest â Winter Parkâs premier gated, resort-style community! This bea...	3 beds \| 3 baths \| 1,770 sq.ft.	$669,000	Airbnb cash on cash: 3% Traditional cash on cash: 1.84% Airbnb Rental Income: $4337 Traditional Rental Income: $2702 Airbnb ROI: 3% Traditional ROI: 1.84%
1929 S LAKEMONT AVENUE Winter Park, FL This modern Winter Park townhome sits in a quiet pocket between Lake Spier and Lake Compto...	3 beds \| 4 baths \| 2,160 sq.ft.	$949,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 0.68% Airbnb Rental Income: $4337 Traditional Rental Income: $2953 Airbnb ROI: 1.22% Traditional ROI: 0.68%
7641 Village Green Dr Winter Park, FL Welcome to this inviting single-family home at 7641 Village Green Dr in desirable Winter P...	3 beds \| 3 baths \| 1,602 sq.ft.	$550,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 3.57% Airbnb Rental Income: $4337 Traditional Rental Income: $2970 Airbnb ROI: 4.45% Traditional ROI: 3.57%

Real Estate investment in Winter-park, FL

There are 323 properties for sale in the city of Winter Park . The median list price in Winter Park is $550,000 and the average price per square foot is $283. In February 2026, the average monthly cash on cash return in Winter Park is 2.00%. The average monthly rental income in Winter Park is $2,127.

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

There are 323 investment properties available for sale in Winter-park.

In 2026, 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

740 BAFFIE AVENUE

Winter Park, FL

3 beds | 2 baths | 1,456 sq.ft.

$420,000

Airbnb cash on cash: 6.22%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $4337

Traditional Rental Income: $2229

Airbnb ROI: 6.22%

Traditional ROI: 3.18%

1018 TURNER ROAD

Winter Park, FL

3 beds | 2 baths | 2,237 sq.ft.

$835,000

Airbnb cash on cash: 2.27%

Traditional cash on cash: 2.32%

Airbnb Rental Income: $4337

Traditional Rental Income: $3458

Airbnb ROI: 2.27%

Traditional ROI: 2.32%

1324 INDIANA AVENUE

Winter Park, FL

4 beds | 3 baths | 1,692 sq.ft.

$745,000

Airbnb cash on cash: 4.32%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $5745

Traditional Rental Income: $2954

Airbnb ROI: 4.32%

Traditional ROI: 1.95%

701 DENTON ROAD

Winter Park, FL

3 beds | 2 baths | 2,268 sq.ft.

$565,000

Airbnb cash on cash: 4.22%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $4337

Traditional Rental Income: $3016

Airbnb ROI: 4.22%

Traditional ROI: 3.44%

1400 S PENNSYLVANIA AVENUE

Winter Park, FL

4 beds | 3 baths | 2,310 sq.ft.

$1,250,000

Airbnb cash on cash: 1.79%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $5745

Traditional Rental Income: $3232

Airbnb ROI: 1.79%

Traditional ROI: 0.61%

208 BREWER AVENUE

Winter Park, FL

4 beds | 4 baths | 2,173 sq.ft.

$925,000

Airbnb cash on cash: 3.29%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $5745

Traditional Rental Income: $4604

Airbnb ROI: 3.29%

Traditional ROI: 3.3%

2811 EASTERN PARKWAY

Winter Park, FL

3 beds | 2 baths | 1,433 sq.ft.

$625,000

Airbnb cash on cash: 3.82%

Traditional cash on cash: 3%

Airbnb Rental Income: $4337

Traditional Rental Income: $2945

Airbnb ROI: 3.82%

Traditional ROI: 3%

150 Killarney Bay Ct #5

Winter Park, FL

2 beds | 2 baths | 1,140 sq.ft.

$345,000

Airbnb cash on cash: 4.33%

Traditional cash on cash: 1.93%

Airbnb Rental Income: $3260

Traditional Rental Income: $1751

Airbnb ROI: 4.33%