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
1408 Chapman Cir Winter Park, FL Opportunity awaits in the most desirable neighborhood! Buyers have cold feet. Nestled in t...	4 beds \| 4 baths \| 3,237 sq.ft.	$1,495,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 1.3% Airbnb Rental Income: $5745 Traditional Rental Income: $4938 Airbnb ROI: 1.06% Traditional ROI: 1.3%
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%
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%
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%
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%
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%
1702 Glenridge Way Winter Park, FL Rare opportunity in Winter Park to own a move-in-ready, fully renovated corner lakefront t...	2 beds \| 2 baths \| 1,832 sq.ft.	$789,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 0.81% Airbnb Rental Income: $1969 Traditional Rental Income: $2528 Airbnb ROI: -0.64% Traditional ROI: 0.81%
3601 Midiron Dr Winter Park, FL BUILD YOUR DREAM HOME IN WINTER PARK! Nestled directly across from the historic Dubsdread...	N/A beds \| N/A baths \| 954 sq.ft.	$489,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 1.01% Airbnb Rental Income: $2207 Traditional Rental Income: $1593 Airbnb ROI: 1.13% Traditional ROI: 1.01%
151 N Orlando Ave #118 Winter Park, FL Investment opportunity! Discover this hidden gemâa 2-bed, 1-bath condo nestled in the he...	2 beds \| 1 baths \| 710 sq.ft.	$299,999	Airbnb cash on cash: 5.17% Traditional cash on cash: 1.93% Airbnb Rental Income: $3260 Traditional Rental Income: $1610 Airbnb ROI: 5.17% Traditional ROI: 1.93%
1981 BLUE RIDGE ROAD Winter Park, FL One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE thr...	4 beds \| 2 baths \| 2,750 sq.ft.	$1,180,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 1.1% Airbnb Rental Income: $5745 Traditional Rental Income: $2726 Airbnb ROI: 2.8% Traditional ROI: 1.1%
763 Overspin Dr Winter Park, FL 763 Overspin Dr, Orlando, FL 32789 \| Other	N/A beds \| N/A baths \| N/A	$699,000	Airbnb cash on cash: 0.51% Traditional cash on cash: -0.75% Airbnb Rental Income: $2207 Traditional Rental Income: $835 Airbnb ROI: 0.51% Traditional ROI: -0.75%
2500 Lee Rd #243 Winter Park, FL Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community ...	1 beds \| 1 baths \| 645 sq.ft.	$145,000	Airbnb cash on cash: 8.17% Traditional cash on cash: 5.62% Airbnb Rental Income: $2412 Traditional Rental Income: $1467 Airbnb ROI: 8.17% Traditional ROI: 5.62%
726 And 720 N PENNSYLVANIA AVENUE Winter Park, FL Welcome to this exceptional duplex, a rare gem in Winter Park offering unmatched flexibili...	6 beds \| N/A baths \| 2,284 sq.ft.	$1,215,000	Airbnb cash on cash: 0.33% Traditional cash on cash: -0.02% Airbnb Rental Income: $3260 Traditional Rental Income: $2125 Airbnb ROI: 0.33% Traditional ROI: -0.02%
101 S Interlachen Ave #104 Winter Park, FL FIRST TIME ON THE MARKET! ULTRA-RARE GROUND FLOOR CONDO IN DOWNTOWN WINTER PARK'S LACHEN H...	2 beds \| 2 baths \| 949 sq.ft.	$635,000	Airbnb cash on cash: 1.55% Traditional cash on cash: -0.12% Airbnb Rental Income: $3260 Traditional Rental Income: $1543 Airbnb ROI: 1.55% Traditional ROI: -0.12%
1564 CAVENDISH ROAD Winter Park, FL Charming 3BR bungalow in sought-after Orwin Manor with timeless appeal and tons of potenti...	3 beds \| 1 baths \| 1,140 sq.ft.	$450,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 1.95% Airbnb Rental Income: $4337 Traditional Rental Income: $1838 Airbnb ROI: 5.72% Traditional ROI: 1.95%
2500 Lee Rd #208 Winter Park, FL This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfor...	2 beds \| 2 baths \| 956 sq.ft.	$190,000	Airbnb cash on cash: 9.32% Traditional cash on cash: 5.21% Airbnb Rental Income: $3260 Traditional Rental Income: $1786 Airbnb ROI: 9.32% Traditional ROI: 5.21%
1996 Indiana Ave Winter Park, FL Investor Special â Fixer Upper Opportunity in Winter Park / College Park Area. Rare o...	2 beds \| 1 baths \| 818 sq.ft.	$249,900	Airbnb cash on cash: 8.76% Traditional cash on cash: 4.26% Airbnb Rental Income: $3260 Traditional Rental Income: $1467 Airbnb ROI: 8.76% Traditional ROI: 4.26%
1112 PRESERVE POINT DRIVE Winter Park, FL Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rar...	5 beds \| 6 baths \| 6,502 sq.ft.	$8,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.4% Airbnb Rental Income: $null Traditional Rental Income: $9747 Airbnb ROI: N/A Traditional ROI: -0.4%
240 KILLARNEY BAY COURT #4 Winter Park, FL Welcome to Killarney BayâWinter Parkâs best-kept secret for tranquil lakeside living, ...	2 beds \| 3 baths \| 1,536 sq.ft.	$399,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 3.01% Airbnb Rental Income: $3260 Traditional Rental Income: $2209 Airbnb ROI: 3.86% Traditional ROI: 3.01%
2211 Azalea Pl Winter Park, FL Luxurious waterfront estate in one of Winter Parkâs most prestigious neighborhoods, offe...	5 beds \| 6 baths \| 7,278 sq.ft.	$5,495,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.25% Airbnb Rental Income: $null Traditional Rental Income: $9809 Airbnb ROI: N/A Traditional ROI: 0.25%
311 E Morse Blvd #7-5 Winter Park, FL Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispe...	1 beds \| 1 baths \| 482 sq.ft.	$359,000	Airbnb cash on cash: 0.54% Traditional cash on cash: -0.88% Airbnb Rental Income: $2412 Traditional Rental Income: $1343 Airbnb ROI: 0.54% Traditional ROI: -0.88%

Real Estate investment in Winter-park, FL

There are 337 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 337 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

1408 Chapman Cir

Winter Park, FL

4 beds | 4 baths | 3,237 sq.ft.

$1,495,000

Airbnb cash on cash: 1.06%

Traditional cash on cash: 1.3%

Airbnb Rental Income: $5745

Traditional Rental Income: $4938

Airbnb ROI: 1.06%

Traditional ROI: 1.3%

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%

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%

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%

Traditional ROI: 1.93%

726 N PENNSYLVANIA AVENUE

Winter Park, FL

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

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%

311 E MORSE BOULEVARD #7-2

Winter Park, FL

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%

1702 Glenridge Way

Winter Park, FL

2 beds | 2 baths | 1,832 sq.ft.

$789,000

Airbnb cash on cash: -0.64%

Traditional cash on cash: 0.81%

Airbnb Rental Income: $1969

Traditional Rental Income: $2528

Airbnb ROI: -0.64%