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
1751 GOODRICH AVENUE Winter Park, FL Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park...	4 beds \| 4 baths \| 2,170 sq.ft.	$1,425,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 1.11% Airbnb Rental Income: $5745 Traditional Rental Income: $3743 Airbnb ROI: 1.76% Traditional ROI: 1.11%
1307 Formosa Ave Winter Park, FL Charming 2-bed home in Winter Park located in the Golfview subdivision offering approximat...	2 beds \| 1 baths \| 1,150 sq.ft.	$374,300	Airbnb cash on cash: 4.34% Traditional cash on cash: 3.41% Airbnb Rental Income: $3260 Traditional Rental Income: $2199 Airbnb ROI: 4.34% Traditional ROI: 3.41%
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.	$1,349,900	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.57% Airbnb Rental Income: $5745 Traditional Rental Income: $4790 Airbnb ROI: 2.41% Traditional ROI: 2.57%
1441 CARDINAL COURT Winter Park, FL Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet...	4 beds \| 6 baths \| 4,066 sq.ft.	$4,285,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 0.07% Airbnb Rental Income: $5745 Traditional Rental Income: $8729 Airbnb ROI: -0.97% Traditional ROI: 0.07%
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.	$325,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 3.69% Airbnb Rental Income: $3260 Traditional Rental Income: $2233 Airbnb ROI: 4.65% Traditional ROI: 3.69%
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.	$719,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 2.46% Airbnb Rental Income: $5745 Traditional Rental Income: $3035 Airbnb ROI: 4.79% Traditional ROI: 2.46%
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.	$3,174,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 0.25% Airbnb Rental Income: $5745 Traditional Rental Income: $5609 Airbnb ROI: -0.09% Traditional ROI: 0.25%
363 N PHELPS AVENUE 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: 2.18% Traditional cash on cash: 1.75% Airbnb Rental Income: $5745 Traditional Rental Income: $4109 Airbnb ROI: 2.18% Traditional ROI: 1.75%
1800 MAGNOLIA AVENUE Winter Park, FL One or more photo(s) has been virtually staged. NEW PRICE! Experience refined living with ...	4 beds \| 3 baths \| 2,431 sq.ft.	$1,000,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 2.48% Airbnb Rental Income: $5745 Traditional Rental Income: $4421 Airbnb ROI: 2.68% Traditional ROI: 2.48%
2036 VIA TUSCANY Winter Park, FL WINTER PARK VIAâS!!! Incredible Oversized Lot is located in the âHeartâ of Winter Pa...	3 beds \| 2 baths \| 2,148 sq.ft.	$2,000,000	Airbnb cash on cash: 0.04% Traditional cash on cash: -0.02% Airbnb Rental Income: $4337 Traditional Rental Income: $3307 Airbnb ROI: 0.04% Traditional ROI: -0.02%
1347 Chapman Cir Winter Park, FL Beautiful Windsong custom home! This 4 bedroom 3.5 bath home features a spectacular chef's...	4 beds \| 3 baths \| 2,922 sq.ft.	$1,395,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 0.39% Airbnb Rental Income: $5745 Traditional Rental Income: $3212 Airbnb ROI: 1.46% Traditional ROI: 0.39%
1473 Berkshire Ave Winter Park, FL Exquisite New 2025 Luxury Home in the Heart of Winter Park - Welcome to 1473 Berkshire Ave...	5 beds \| 4 baths \| 2,895 sq.ft.	$1,479,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.62% Airbnb Rental Income: $null Traditional Rental Income: $4216 Airbnb ROI: N/A Traditional ROI: 1.62%
250 CORTLAND AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Introducing 250 Cortland Ave â a refined...	3 beds \| 2 baths \| 2,114 sq.ft.	$950,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 2.4% Airbnb Rental Income: $4337 Traditional Rental Income: $3501 Airbnb ROI: 2.31% Traditional ROI: 2.4%
1150 VIA SALERNO Winter Park, FL In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalis...	4 beds \| 6 baths \| 3,850 sq.ft.	$4,195,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.74% Airbnb Rental Income: $5745 Traditional Rental Income: $11661 Airbnb ROI: -0.08% Traditional ROI: 1.74%
811 Overspin Dr Winter Park, FL 811 Overspin Dr, Orlando, FL 32789 \| Single Family Residential	2 beds \| 1 baths \| 749 sq.ft.	$349,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 3.03% Airbnb Rental Income: $3260 Traditional Rental Income: $1705 Airbnb ROI: 5.54% Traditional ROI: 3.03%
1651 Westchester Ave Winter Park, FL Under contract-accepting backup offers. Welcome to this exquisite Orwin Manor Cape Cod cla...	3 beds \| 2 baths \| 2,426 sq.ft.	$1,275,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 1.52% Airbnb Rental Income: $4337 Traditional Rental Income: $3402 Airbnb ROI: 1.54% Traditional ROI: 1.52%
1707 Harmon Ave Winter Park, FL 1707 Harmon Ave, Orlando, FL 32789 \| Single Family Residential	3 beds \| 2 baths \| 1,669 sq.ft.	$695,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 1.04% Airbnb Rental Income: $4337 Traditional Rental Income: $1986 Airbnb ROI: 3.26% Traditional ROI: 1.04%
2412 CHANTILLY AVENUE Winter Park, FL Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaV...	5 beds \| 7 baths \| 4,506 sq.ft.	$2,394,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.68% Airbnb Rental Income: $null Traditional Rental Income: $13144 Airbnb ROI: N/A Traditional ROI: 4.68%
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: 1.17% Traditional cash on cash: 1.52% Airbnb Rental Income: $2207 Traditional Rental Income: $1811 Airbnb ROI: 1.17% Traditional ROI: 1.52%
1981 BLUE RIDGE ROAD Winter Park, FL Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring ...	4 beds \| 2 baths \| 2,750 sq.ft.	$1,150,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.23% Airbnb Rental Income: $5745 Traditional Rental Income: $3522 Airbnb ROI: 2.24% Traditional ROI: 1.23%
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: 2.33% Traditional cash on cash: 1.14% Airbnb Rental Income: $5745 Traditional Rental Income: $3328 Airbnb ROI: 2.33% Traditional ROI: 1.14%
1810 HOLLYWOOD AVENUE Winter Park, FL Under Construction. Estimated completion August!! Experience modern luxury living in the h...	4 beds \| 4 baths \| 2,604 sq.ft.	$1,689,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 1.73% Airbnb Rental Income: $5745 Traditional Rental Income: $5013 Airbnb ROI: 1.47% Traditional ROI: 1.73%
1885 TEMPLE DRIVE Winter Park, FL Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, thi...	5 beds \| 4 baths \| 3,691 sq.ft.	$2,265,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.81% Airbnb Rental Income: $null Traditional Rental Income: $6564 Airbnb ROI: N/A Traditional ROI: 1.81%
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: -0.05% Airbnb Rental Income: $2207 Traditional Rental Income: $1290 Airbnb ROI: 0.51% Traditional ROI: -0.05%
450 LAKEWOOD DRIVE Winter Park, FL Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Flo...	5 beds \| 6 baths \| 4,572 sq.ft.	$2,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.5% Airbnb Rental Income: $null Traditional Rental Income: $9247 Airbnb ROI: N/A Traditional ROI: 2.5%
1782 PINE AVENUE Winter Park, FL Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where ...	5 beds \| 7 baths \| 4,782 sq.ft.	$4,197,000	Airbnb cash on cash: N/A Traditional cash on cash: 2% Airbnb Rental Income: $null Traditional Rental Income: $12218 Airbnb ROI: N/A Traditional ROI: 2%
2500 LEE ROAD #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: 9.87% Traditional cash on cash: 8.11% Airbnb Rental Income: $3260 Traditional Rental Income: $2235 Airbnb ROI: 9.87% Traditional ROI: 8.11%
1768 MONDRIAN CIRCLE Winter Park, FL One or more photo(s) has been virtually staged. Step into refined lakeside living at the e...	3 beds \| 4 baths \| 2,193 sq.ft.	$1,099,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 1.61% Airbnb Rental Income: $4337 Traditional Rental Income: $4159 Airbnb ROI: 0.89% Traditional ROI: 1.61%
2211 Azalea Pl Winter Park, FL Luxurious waterfront estate in one of Winter Parkâs most prestigious neighborhoods, offe...	5 beds \| 7 baths \| 7,278 sq.ft.	$5,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.16% Airbnb Rental Income: $null Traditional Rental Income: $13911 Airbnb ROI: N/A Traditional ROI: 1.16%
311 E MORSE BOULEVARD #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: 0.12% Airbnb Rental Income: $2412 Traditional Rental Income: $1680 Airbnb ROI: 0.54% Traditional ROI: 0.12%
Lot #21 KAROLINA AVE Winter Park, FL Pre-Construction. To be built. This is your final opportunity to build a custom home in on...	4 beds \| 4 baths \| 2,662 sq.ft.	$944,890	Airbnb cash on cash: 3.89% Traditional cash on cash: 3.4% Airbnb Rental Income: $5745 Traditional Rental Income: $4170 Airbnb ROI: 3.89% Traditional ROI: 3.4%
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.	$4,075,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 0.41% Airbnb Rental Income: $5745 Traditional Rental Income: $8217 Airbnb ROI: -0.55% Traditional ROI: 0.41%
607 ELLEN DRIVE Winter Park, FL NEW PRICE!!! Discover sophisticated modern living at 607 Ellen Drive, a stunning new const...	4 beds \| 5 baths \| 2,812 sq.ft.	$1,499,900	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.14% Airbnb Rental Income: $5745 Traditional Rental Income: $6330 Airbnb ROI: 1.89% Traditional ROI: 3.14%
3018 Northwood Blvd Winter Park, FL "PRICE REDUCTION" ON THIS MOVE-IN READY, 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH "NO ...	3 beds \| 2 baths \| 1,761 sq.ft.	$659,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 3.23% Airbnb Rental Income: $4337 Traditional Rental Income: $3308 Airbnb ROI: 3.42% Traditional ROI: 3.23%
1134 WASHINGTON AVENUE #13 Winter Park, FL Discover this generously sized 3-bedroom, 3.5-bath townhome offering 2,083 square feet of ...	3 beds \| 4 baths \| 2,083 sq.ft.	$595,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 4.34% Airbnb Rental Income: $4337 Traditional Rental Income: $4518 Airbnb ROI: 2.37% Traditional ROI: 4.34%
151 N ORLANDO AVENUE #115 Winter Park, FL Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. F...	2 beds \| 1 baths \| 710 sq.ft.	$298,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 3.16% Airbnb Rental Income: $3260 Traditional Rental Income: $2075 Airbnb ROI: 4.78% Traditional ROI: 3.16%
560 OLOLU DRIVE Winter Park, FL Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and abs...	2 beds \| 2 baths \| 1,086 sq.ft.	$925,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 1.02% Airbnb Rental Income: $3260 Traditional Rental Income: $2632 Airbnb ROI: 0.9% Traditional ROI: 1.02%
1780 BRYAN AVENUE Winter Park, FL Build your dream home in one of Winter Parkâs most desirable locations. This 66.6â x 1...	4 beds \| 2 baths \| 1,617 sq.ft.	$849,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 2.01% Airbnb Rental Income: $5745 Traditional Rental Income: $3153 Airbnb ROI: 3.84% Traditional ROI: 2.01%
2361 Mulbry Dr Winter Park, FL Casa Noir \| Selected as a 2026 Parade of Homes showcase in Winter Park, this signature new...	4 beds \| 4 baths \| 3,111 sq.ft.	$2,325,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 1.42% Airbnb Rental Income: $5745 Traditional Rental Income: $5896 Airbnb ROI: 0.82% Traditional ROI: 1.42%
2500 LEE RD. #222 Winter Park, FL Lakefront access in Winter Park under $200K! One of the few condos at this price point off...	1 beds \| 1 baths \| 645 sq.ft.	$189,500	Airbnb cash on cash: 6.59% Traditional cash on cash: 6.4% Airbnb Rental Income: $2412 Traditional Rental Income: $1787 Airbnb ROI: 6.59% Traditional ROI: 6.4%

Real Estate investment in Winter-park, FL

There are 197 properties for sale in the city of Winter Park . The median list price in Winter Park is $495,000 and the average price per square foot is $255. In May 2026, the average monthly cash on cash return in Winter Park is 3.00%. The average monthly rental income in Winter Park is $2,294.

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

There are 197 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

1751 GOODRICH AVENUE

Winter Park, FL

4 beds | 4 baths | 2,170 sq.ft.

$1,425,000

Airbnb cash on cash: 1.76%

Traditional cash on cash: 1.11%

Airbnb Rental Income: $5745

Traditional Rental Income: $3743

Airbnb ROI: 1.76%

Traditional ROI: 1.11%

1307 Formosa Ave

Winter Park, FL

2 beds | 1 baths | 1,150 sq.ft.

$374,300

Airbnb cash on cash: 4.34%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $3260

Traditional Rental Income: $2199

Airbnb ROI: 4.34%

Traditional ROI: 3.41%

1649 Harmon Ave

Winter Park, FL

4 beds | 3 baths | 3,223 sq.ft.

$1,349,900

Airbnb cash on cash: 2.41%

Traditional cash on cash: 2.57%

Airbnb Rental Income: $5745

Traditional Rental Income: $4790

Airbnb ROI: 2.41%

Traditional ROI: 2.57%

1441 CARDINAL COURT

Winter Park, FL

4 beds | 6 baths | 4,066 sq.ft.

$4,285,000

Airbnb cash on cash: -0.97%

Traditional cash on cash: 0.07%

Airbnb Rental Income: $5745

Traditional Rental Income: $8729

Airbnb ROI: -0.97%

Traditional ROI: 0.07%

150 KILLARNEY BAY COURT #5

Winter Park, FL

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

$325,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $3260

Traditional Rental Income: $2233

Airbnb ROI: 4.65%

Traditional ROI: 3.69%

2333 WESTMINSTER COURT

Winter Park, FL

4 beds | 2 baths | 1,877 sq.ft.

$719,000

Airbnb cash on cash: 4.79%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $5745

Traditional Rental Income: $3035

Airbnb ROI: 4.79%

Traditional ROI: 2.46%

948 POINCIANA LANE

Winter Park, FL

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

$3,174,000

Airbnb cash on cash: -0.09%

Traditional cash on cash: 0.25%

Airbnb Rental Income: $5745

Traditional Rental Income: $5609

Airbnb ROI: -0.09%

Traditional ROI: 0.25%

363 N PHELPS AVENUE

Winter Park, FL

4 beds | 3 baths | 2,871 sq.ft.

$1,249,000

Airbnb cash on cash: 2.18%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $5745

Traditional Rental Income: $4109

Airbnb ROI: 2.18%