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
1981 Blue Ridge Rd Winter Park, FL 1981 Blue Ridge Rd, Orlando, FL 32789 \| Single Family Residential	4 beds \| 2 baths \| 2,750 sq.ft.	$1,150,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 1.14% Airbnb Rental Income: $5539 Traditional Rental Income: $3328 Airbnb ROI: 2.17% Traditional ROI: 1.14%
1995 CANNY COVE Winter Park, FL Welcome to Grayson Square at Winter Park by Pulte Homes. This interior Springdale II two-s...	3 beds \| 3 baths \| 1,907 sq.ft.	$425,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 2.83% Airbnb Rental Income: $2443 Traditional Rental Income: $2587 Airbnb ROI: 0.97% Traditional ROI: 2.83%
1161 VALENCIA AVENUE Winter Park, FL Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, bu...	4 beds \| 5 baths \| 4,181 sq.ft.	$3,995,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.44% Airbnb Rental Income: $5539 Traditional Rental Income: $8217 Airbnb ROI: -0.59% Traditional ROI: 0.44%
7470 CANFORD COURT #23 Winter Park, FL New updates, a new fence, and extra outdoor space on a desirable corner lot. Beautifully u...	3 beds \| 3 baths \| 1,580 sq.ft.	$245,900	Airbnb cash on cash: 2.55% Traditional cash on cash: 3.95% Airbnb Rental Income: $2443 Traditional Rental Income: $2173 Airbnb ROI: 2.55% Traditional ROI: 3.95%
1951 CANNY COVE Winter Park, FL Welcome to easy, light-filled living in this beautifully maintained 3-bedroom, 2.5-bath co...	3 beds \| 3 baths \| 1,782 sq.ft.	$444,900	Airbnb cash on cash: 0.68% Traditional cash on cash: 2.78% Airbnb Rental Income: $2443 Traditional Rental Income: $2724 Airbnb ROI: 0.68% Traditional ROI: 2.78%
423 OLOLU DRIVE Winter Park, FL PRICE IMPROVEMENT! Welcome to this beautifully remodeled two story home in one of Winter P...	3 beds \| 3 baths \| 1,920 sq.ft.	$549,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 3.9% Airbnb Rental Income: $2443 Traditional Rental Income: $2979 Airbnb ROI: 1.69% Traditional ROI: 3.9%
948 POINCIANA LANE Winter Park, FL Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an ...	4 beds \| 4 baths \| 3,676 sq.ft.	$2,899,900	Airbnb cash on cash: -0.07% Traditional cash on cash: 0.37% Airbnb Rental Income: $5539 Traditional Rental Income: $5609 Airbnb ROI: -0.07% Traditional ROI: 0.37%
418 GILBERT ROAD Winter Park, FL Beautifully renovated solid block home on a quiet street in highly desirable Winter Park P...	3 beds \| 3 baths \| 1,680 sq.ft.	$710,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 2.11% Airbnb Rental Income: $2443 Traditional Rental Income: $2995 Airbnb ROI: 0.38% Traditional ROI: 2.11%
1782 PINE AVENUE Winter Park, FL (HUGE PRICE REDUCTION & NEWLY ENHANCED REAR LANDSCAPING ADDED FOR EXCEPTIONAL PRIVACY AND ...	5 beds \| 7 baths \| 4,782 sq.ft.	$3,875,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.25% Airbnb Rental Income: $null Traditional Rental Income: $12218 Airbnb ROI: N/A Traditional ROI: 2.25%
3054 BLUEBROOK DRIVE Winter Park, FL Just Reduced the Price! "Open the Doors to Your Dreams" of owning an Affordable Home with ...	3 beds \| 2 baths \| 1,939 sq.ft.	$410,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 4.36% Airbnb Rental Income: $2443 Traditional Rental Income: $2747 Airbnb ROI: 2.01% Traditional ROI: 4.36%
3440 ALLSTON LANE Winter Park, FL Exceptional Single-Family Home in Winter Park, FL This beautifully maintained 3-bedroom, ...	3 beds \| 3 baths \| 1,533 sq.ft.	$405,000	Airbnb cash on cash: 3.09% Traditional cash on cash: 3.88% Airbnb Rental Income: $2443 Traditional Rental Income: $2145 Airbnb ROI: 3.09% Traditional ROI: 3.88%
639 SAINT JOHNS COURT #639 Winter Park, FL Freshly painted 2 Bedroom/2 Bath townhouse-style condo with no neighbors above or below, b...	2 beds \| 2 baths \| 1,120 sq.ft.	$194,900	Airbnb cash on cash: 4.74% Traditional cash on cash: 5.34% Airbnb Rental Income: $2559 Traditional Rental Income: $2054 Airbnb ROI: 4.74% Traditional ROI: 5.34%
3374 HAMLET LOOP Winter Park, FL Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a...	3 beds \| 3 baths \| 1,397 sq.ft.	$365,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 3.26% Airbnb Rental Income: $2443 Traditional Rental Income: $2118 Airbnb ROI: 2.47% Traditional ROI: 3.26%
2333 WESTMINSTER COURT Winter Park, FL Settled on a rare double lot in the heart of Winter Park, this 4-bedroom, 2-bath home deli...	4 beds \| 2 baths \| 1,877 sq.ft.	$699,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 2.56% Airbnb Rental Income: $5539 Traditional Rental Income: $3035 Airbnb ROI: 4.69% Traditional ROI: 2.56%
2157 LAKE DRIVE Winter Park, FL Welcome to this beautifully maintained Winter Park home in coveted 32789, offering over 2,...	3 beds \| 3 baths \| 2,124 sq.ft.	$689,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 3.58% Airbnb Rental Income: $2443 Traditional Rental Income: $3185 Airbnb ROI: 1.5% Traditional ROI: 3.58%
1000 S SEMORAN BOULEVARD #715 Winter Park, FL Prime location meets exceptional value in the highly sought-after Winter Park area! This f...	1 beds \| 1 baths \| 735 sq.ft.	$122,990	Airbnb cash on cash: 4.73% Traditional cash on cash: 7.59% Airbnb Rental Income: $1806 Traditional Rental Income: $1655 Airbnb ROI: 4.73% Traditional ROI: 7.59%
1842 Puritan Ave Winter Park, FL Modern design , open concept layout , sleek quartz counter top , all new appliances, new l...	4 beds \| 2 baths \| N/A	$429,000	Airbnb cash on cash: 8.92% Traditional cash on cash: 4.33% Airbnb Rental Income: $5539 Traditional Rental Income: $2586 Airbnb ROI: 8.92% Traditional ROI: 4.33%
2222 Marsh Sedge Lane Winter Park, FL Welcome to your dream Home! This stunning and elegant single-story home, built by Meritage...	4 beds \| 3 baths \| 2,192 sq.ft.	$739,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 1.91% Airbnb Rental Income: $5539 Traditional Rental Income: $3097 Airbnb ROI: 3.84% Traditional ROI: 1.91%
1850 Aster Drive Winter Park, FL Welcome to the heart of Winter Park.This beautifully maintained 4-bedroom, 2.5-bath pool h...	4 beds \| 3 baths \| 1,656 sq.ft.	$485,000	Airbnb cash on cash: 8.21% Traditional cash on cash: 4.26% Airbnb Rental Income: $5539 Traditional Rental Income: $2633 Airbnb ROI: 8.21% Traditional ROI: 4.26%
2625 Park Place Dr Winter Park, FL 2625 Park Place Dr, Winter Park, FL 32789 \| Single Family Residential	4 beds \| 4 baths \| 3,460 sq.ft.	$1,799,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.03% Airbnb Rental Income: $5539 Traditional Rental Income: $3453 Airbnb ROI: 0.61% Traditional ROI: 0.03%
528 Saint Dunstan Way Winter Park, FL Welcome to Winter Park Pines, one of Winter Park's most desirable and established neighbor...	3 beds \| 2 baths \| 1,656 sq.ft.	$524,990	Airbnb cash on cash: 1.39% Traditional cash on cash: 2.34% Airbnb Rental Income: $2443 Traditional Rental Income: $2318 Airbnb ROI: 1.39% Traditional ROI: 2.34%
1600 Alabama Dr #402 Winter Park, FL Nestled along one of Winter Park's most cherished brick-lined streets, this elegantly appo...	2 beds \| 2 baths \| 1,574 sq.ft.	$1,250,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 0.78% Airbnb Rental Income: $2559 Traditional Rental Income: $2554 Airbnb ROI: 0.26% Traditional ROI: 0.78%
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.	$175,000	Airbnb cash on cash: 6.36% Traditional cash on cash: 8.11% Airbnb Rental Income: $2559 Traditional Rental Income: $2235 Airbnb ROI: 6.36% Traditional ROI: 8.11%
763 Overspin Dr Winter Park, FL 763 Overspin Dr, Orlando, FL 32789 \| Other	N/A beds \| N/A baths \| N/A	$650,000	Airbnb cash on cash: -1.9% Traditional cash on cash: 0.09% Airbnb Rental Income: $328 Traditional Rental Income: $1290 Airbnb ROI: -1.9% Traditional ROI: 0.09%
7484 Canford Ct #8 Winter Park, FL This three-bedroom, three-bath updated Winter Park townhome-style condo is located in a qu...	3 beds \| 3 baths \| 1,578 sq.ft.	$240,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 5.13% Airbnb Rental Income: $2443 Traditional Rental Income: $2239 Airbnb ROI: 3.41% Traditional ROI: 5.13%
363 N Phelps Ave Winter Park, FL This light and bright, single-story, almost 3,000 square foot pool home features a split p...	4 beds \| 3 baths \| 2,871 sq.ft.	$1,249,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 1.75% Airbnb Rental Income: $5539 Traditional Rental Income: $4109 Airbnb ROI: 2.03% Traditional ROI: 1.75%
1914 Bonanza Ct Winter Park, FL Welcome to your winter Park retreat! Step into this beautifully renovated 3 bedroom, 2 bat...	3 beds \| 2 baths \| 1,727 sq.ft.	$429,999	Airbnb cash on cash: 2.32% Traditional cash on cash: 4.64% Airbnb Rental Income: $2443 Traditional Rental Income: $2782 Airbnb ROI: 2.32% Traditional ROI: 4.64%
3463 Arnel Dr Winter Park, FL One or more photo(s) has been virtually staged. DO NOT MISS THIS OPPORTUNITY! PRICE IMPROV...	3 beds \| 2 baths \| 1,770 sq.ft.	$404,900	Airbnb cash on cash: 2.35% Traditional cash on cash: 5.71% Airbnb Rental Income: $2443 Traditional Rental Income: $3168 Airbnb ROI: 2.35% Traditional ROI: 5.71%
420 Ohio St Winter Park, FL Pre-Construction. To be built. On a prominent corner lot in the evolving Killarney neighbo...	4 beds \| 4 baths \| 2,900 sq.ft.	$1,275,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.46% Airbnb Rental Income: $null Traditional Rental Income: $8378 Airbnb ROI: N/A Traditional ROI: 5.46%
1780 Bryan Ave Winter Park, FL Build your dream home in one of Winter Parkâs most desirable locations. This 66.6â x 1...	N/A beds \| N/A baths \| 1,617 sq.ft.	$850,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 2.01% Airbnb Rental Income: $5539 Traditional Rental Income: $3153 Airbnb ROI: 3.62% Traditional ROI: 2.01%
1809 Hammerlin Ave Winter Park, FL 1809 Hammerlin Ave, Winter Park, FL 32789 \| Condo/Coop	3 beds \| 2 baths \| 1,818 sq.ft.	$549,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 2.17% Airbnb Rental Income: $2443 Traditional Rental Income: $2615 Airbnb ROI: 0.67% Traditional ROI: 2.17%
346 S Ranger Blvd Winter Park, FL PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park...	3 beds \| 2 baths \| 1,592 sq.ft.	$475,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 4.07% Airbnb Rental Income: $2443 Traditional Rental Income: $2841 Airbnb ROI: 1.83% Traditional ROI: 4.07%
2918 Antique Oaks Cir #25 Winter Park, FL 2 Bedroom 2 bath condo 1 block south of University Blvd great location for UCF or Full Sai...	2 beds \| 2 baths \| 1,018 sq.ft.	$189,000	Airbnb cash on cash: 5.48% Traditional cash on cash: 5.4% Airbnb Rental Income: $2559 Traditional Rental Income: $1930 Airbnb ROI: 5.48% Traditional ROI: 5.4%
1649 Harmon Ave Winter Park, FL Priced to Close before the end of the year!!! New Construction Orwin Manor Area home tha...	4 beds \| 3 baths \| 3,223 sq.ft.	$1,250,000	Airbnb cash on cash: 2.4% Traditional cash on cash: 2.7% Airbnb Rental Income: $5539 Traditional Rental Income: $4790 Airbnb ROI: 2.4% Traditional ROI: 2.7%
4469 Old Bear Run Winter Park, FL Private, gated lakefront living on Bear Gully Lake one of Winter Parkâs most desirable s...	5 beds \| 4 baths \| 4,288 sq.ft.	$1,799,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $7166 Airbnb ROI: N/A Traditional ROI: 2.64%
318 Vitoria Ave Winter Park, FL Elegant 1922 Mission Revival home, located in popular College Quarter is a registered hist...	3 beds \| 2 baths \| 2,036 sq.ft.	$1,849,900	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.63% Airbnb Rental Income: $2443 Traditional Rental Income: $5197 Airbnb ROI: -0.19% Traditional ROI: 1.63%
189 Lewfield Cir #189 Winter Park, FL Experience the best of the Winter Park lifestyle in this beautifully updated first-floor c...	1 beds \| 1 baths \| 678 sq.ft.	$155,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 5.43% Airbnb Rental Income: $1806 Traditional Rental Income: $1609 Airbnb ROI: 3.46% Traditional ROI: 5.43%
7577 Dockside St Winter Park, FL Virtually Staged. FABULOUS 3 bedroom 2 bath RENOVATED home with a 1 car garage located in ...	3 beds \| 2 baths \| 1,245 sq.ft.	$360,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 3.46% Airbnb Rental Income: $2443 Traditional Rental Income: $1945 Airbnb ROI: 3.17% Traditional ROI: 3.46%
2560 Franklin Ave Winter Park, FL Come see this charming 4 bed, 2 bath, 2 story home in Winter Park/ Lake Killarney location...	4 beds \| 2 baths \| 1,514 sq.ft.	$479,000	Airbnb cash on cash: 6.71% Traditional cash on cash: 3.26% Airbnb Rental Income: $5539 Traditional Rental Income: $2821 Airbnb ROI: 6.71% Traditional ROI: 3.26%
525 S Lakemont Ave Winter Park, FL Winter Park Luxury Awaits You! Welcome to your dream homeâa stunning custom-built luxury...	4 beds \| 3 baths \| 3,330 sq.ft.	$2,099,990	Airbnb cash on cash: 0.8% Traditional cash on cash: 1.7% Airbnb Rental Income: $5539 Traditional Rental Income: $6263 Airbnb ROI: 0.8% Traditional ROI: 1.7%

Real Estate investment in Winter-park, FL

There are 326 properties for sale in the city of Winter Park . The median list price in Winter Park is $799,522 and the average price per square foot is $397. In August 2026, the average monthly cash on cash return in Winter Park is 3.00%. The average monthly rental income in Winter Park is $2,383.

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

There are 326 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 $2,559.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Park, FL

1981 Blue Ridge Rd

Winter Park, FL

4 beds | 2 baths | 2,750 sq.ft.

$1,150,000

Airbnb cash on cash: 2.17%

Traditional cash on cash: 1.14%

Airbnb Rental Income: $5539

Traditional Rental Income: $3328

Airbnb ROI: 2.17%

Traditional ROI: 1.14%

1995 CANNY COVE

Winter Park, FL

3 beds | 3 baths | 1,907 sq.ft.

$425,000

Airbnb cash on cash: 0.97%

Traditional cash on cash: 2.83%

Airbnb Rental Income: $2443

Traditional Rental Income: $2587

Airbnb ROI: 0.97%

Traditional ROI: 2.83%

1161 VALENCIA AVENUE

Winter Park, FL

4 beds | 5 baths | 4,181 sq.ft.

$3,995,000

Airbnb cash on cash: -0.59%

Traditional cash on cash: 0.44%

Airbnb Rental Income: $5539

Traditional Rental Income: $8217

Airbnb ROI: -0.59%

Traditional ROI: 0.44%

7470 CANFORD COURT #23

Winter Park, FL

3 beds | 3 baths | 1,580 sq.ft.

$245,900

Airbnb cash on cash: 2.55%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $2443

Traditional Rental Income: $2173

Airbnb ROI: 2.55%

Traditional ROI: 3.95%

1951 CANNY COVE

Winter Park, FL

3 beds | 3 baths | 1,782 sq.ft.

$444,900

Airbnb cash on cash: 0.68%

Traditional cash on cash: 2.78%

Airbnb Rental Income: $2443

Traditional Rental Income: $2724

Airbnb ROI: 0.68%

Traditional ROI: 2.78%

423 OLOLU DRIVE

Winter Park, FL

3 beds | 3 baths | 1,920 sq.ft.

$549,000

Airbnb cash on cash: 1.69%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $2443

Traditional Rental Income: $2979

Airbnb ROI: 1.69%

Traditional ROI: 3.9%

948 POINCIANA LANE

Winter Park, FL

4 beds | 4 baths | 3,676 sq.ft.

$2,899,900

Airbnb cash on cash: -0.07%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $5539

Traditional Rental Income: $5609

Airbnb ROI: -0.07%

Traditional ROI: 0.37%

418 GILBERT ROAD

Winter Park, FL

3 beds | 3 baths | 1,680 sq.ft.

$710,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $2443

Traditional Rental Income: $2995

Airbnb ROI: 0.38%