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%
437 N CAPEN AVENUE Winter Park, FL Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Wi...	3 beds \| 3 baths \| 1,904 sq.ft.	$849,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 0.2% Airbnb Rental Income: $4337 Traditional Rental Income: $2595 Airbnb ROI: 1.25% Traditional ROI: 0.2%
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.	$1,299,900	Airbnb cash on cash: 2.55% Traditional cash on cash: 2.7% Airbnb Rental Income: $5745 Traditional Rental Income: $4790 Airbnb ROI: 2.55% Traditional ROI: 2.7%
840 W CANTON AVENUE Winter Park, FL Fully renovated 2 bedroom and 2 bathroom home with a bonus room, ideally located in the he...	3 beds \| 2 baths \| 1,370 sq.ft.	$675,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 1.96% Airbnb Rental Income: $4337 Traditional Rental Income: $2489 Airbnb ROI: 3.45% Traditional ROI: 1.96%
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%
2500 LEE ROAD #220 Winter Park, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	2 beds \| 1 baths \| 851 sq.ft.	$199,900	Airbnb cash on cash: 9.12% Traditional cash on cash: 3.58% Airbnb Rental Income: $3260 Traditional Rental Income: $1477 Airbnb ROI: 9.12% Traditional ROI: 3.58%
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.	$315,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 3.83% Airbnb Rental Income: $3260 Traditional Rental Income: $2233 Airbnb ROI: 4.83% Traditional ROI: 3.83%
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: 4.96% Traditional cash on cash: 2.56% Airbnb Rental Income: $5745 Traditional Rental Income: $3035 Airbnb ROI: 4.96% Traditional ROI: 2.56%
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% Traditional cash on cash: 0.37% Airbnb Rental Income: $5745 Traditional Rental Income: $5609 Airbnb ROI: 0% Traditional ROI: 0.37%
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 Virtually Staged. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated c...	4 beds \| 3 baths \| 2,431 sq.ft.	$995,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 2.5% Airbnb Rental Income: $5745 Traditional Rental Income: $4421 Airbnb ROI: 2.69% Traditional ROI: 2.5%
2418 EUSTON ROAD Winter Park, FL Welcome to this beautifully updated three-bedroom, two-and-a-half-bath home located in the...	3 beds \| 3 baths \| 2,048 sq.ft.	$671,111	Airbnb cash on cash: 3.15% Traditional cash on cash: 3.13% Airbnb Rental Income: $4337 Traditional Rental Income: $3412 Airbnb ROI: 3.15% Traditional ROI: 3.13%
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 \| 2,351 sq.ft.	$1,429,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.71% Airbnb Rental Income: $null Traditional Rental Income: $4216 Airbnb ROI: N/A Traditional ROI: 1.71%
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%
2228 AZALEA PLACE Winter Park, FL This elegant transitional French Provincial residence is located on a large, elevated corn...	5 beds \| 6 baths \| 5,152 sq.ft.	$5,600,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.12% Airbnb Rental Income: $null Traditional Rental Income: $7147 Airbnb ROI: N/A Traditional ROI: -0.12%
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%
1250 Formosa Ave Winter Park, FL Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nest...	3 beds \| 3 baths \| 1,937 sq.ft.	$560,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 3.02% Airbnb Rental Income: $4337 Traditional Rental Income: $3249 Airbnb ROI: 3.36% Traditional ROI: 3.02%
2560 Franklin Avenue 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.	$499,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 3.26% Airbnb Rental Income: $5745 Traditional Rental Income: $2821 Airbnb ROI: 7.07% Traditional ROI: 3.26%
1707 Harmon Ave Winter Park, FL 1707 Harmon Ave, Orlando, FL 32789 \| Single Family Residential	3 beds \| 2 baths \| 1,669 sq.ft.	$649,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 1.24% Airbnb Rental Income: $4337 Traditional Rental Income: $1986 Airbnb ROI: 3.62% Traditional ROI: 1.24%
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.	$459,900	Airbnb cash on cash: 1.24% Traditional cash on cash: 1.6% Airbnb Rental Income: $2207 Traditional Rental Income: $1811 Airbnb ROI: 1.24% Traditional ROI: 1.6%
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%
151 NORTH ORLANDO AVENUE #142 Winter Park, FL Lakeside Living Meets Urban Convenience in the Heart of Winter Park! Welcome home t...	1 beds \| 1 baths \| 582 sq.ft.	$199,900	Airbnb cash on cash: 4.78% Traditional cash on cash: 2.45% Airbnb Rental Income: $2412 Traditional Rental Income: $1378 Airbnb ROI: 4.78% Traditional ROI: 2.45%
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.	$2,225,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.86% Airbnb Rental Income: $null Traditional Rental Income: $6564 Airbnb ROI: N/A Traditional ROI: 1.86%
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%
1037 N VIRGINIA AVENUE Winter Park, FL THE best kept secret in WP! Newly renovated charming bungalow located directly on famed 4t...	3 beds \| 1 baths \| 1,101 sq.ft.	$649,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 0.98% Airbnb Rental Income: $4337 Traditional Rental Income: $1959 Airbnb ROI: 3.4% Traditional ROI: 0.98%
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%
3006 Northwood Blvd Winter Park, FL Reimagined from the ground up for modern living while honoring its original mid-century mo...	4 beds \| 3 baths \| 2,075 sq.ft.	$1,249,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 0.79% Airbnb Rental Income: $5745 Traditional Rental Income: $2644 Airbnb ROI: 2.41% Traditional ROI: 0.79%
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%
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%
101 S NEW YORK AVENUE #311 Winter Park, FL Discover luxury living in this exquisitely renovated two-story condominium, ideally situat...	3 beds \| 4 baths \| 3,112 sq.ft.	$1,849,900	Airbnb cash on cash: -0.98% Traditional cash on cash: -0.64% Airbnb Rental Income: $4337 Traditional Rental Income: $4008 Airbnb ROI: -0.98% Traditional ROI: -0.64%
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.	$3,995,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 0.44% Airbnb Rental Income: $5745 Traditional Rental Income: $8217 Airbnb ROI: -0.54% Traditional ROI: 0.44%
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.	$1,449,900	Airbnb cash on cash: 1.99% Traditional cash on cash: 3.28% Airbnb Rental Income: $5745 Traditional Rental Income: $6330 Airbnb ROI: 1.99% Traditional ROI: 3.28%
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.	$290,000	Airbnb cash on cash: 4.93% Traditional cash on cash: 3.27% Airbnb Rental Income: $3260 Traditional Rental Income: $2075 Airbnb ROI: 4.93% Traditional ROI: 3.27%
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 Newly completed and selected as a showcase residence in the 2026 Parade of Homes, Casa Noi...	4 beds \| 4 baths \| 3,130 sq.ft.	$2,249,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 1.5% Airbnb Rental Income: $5745 Traditional Rental Income: $5896 Airbnb ROI: 0.88% Traditional ROI: 1.5%
2500 LEE ROAD #222 Winter Park, FL Stop searchingâyour ultimate lifestyle upgrade is here. Perfectly positioned on the tran...	1 beds \| 1 baths \| 645 sq.ft.	$184,900	Airbnb cash on cash: 6.48% Traditional cash on cash: 6.28% Airbnb Rental Income: $2412 Traditional Rental Income: $1787 Airbnb ROI: 6.48% Traditional ROI: 6.28%
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: 4.77% Traditional cash on cash: 3.9% Airbnb Rental Income: $4337 Traditional Rental Income: $2979 Airbnb ROI: 4.77% Traditional ROI: 3.9%

Real Estate investment in Winter-park, FL

There are 193 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 $396. In July 2026, the average monthly cash on cash return in Winter Park is 3.00%. The average monthly rental income in Winter Park is $2,431.

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

There are 193 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%

437 N CAPEN AVENUE

Winter Park, FL

3 beds | 3 baths | 1,904 sq.ft.

$849,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: 0.2%

Airbnb Rental Income: $4337

Traditional Rental Income: $2595

Airbnb ROI: 1.25%

Traditional ROI: 0.2%

1649 Harmon Ave

Winter Park, FL

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

$1,299,900

Airbnb cash on cash: 2.55%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $5745

Traditional Rental Income: $4790

Airbnb ROI: 2.55%

Traditional ROI: 2.7%

840 W CANTON AVENUE

Winter Park, FL

3 beds | 2 baths | 1,370 sq.ft.

$675,000

Airbnb cash on cash: 3.45%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $4337

Traditional Rental Income: $2489

Airbnb ROI: 3.45%

Traditional ROI: 1.96%

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%

2500 LEE ROAD #220

Winter Park, FL

2 beds | 1 baths | 851 sq.ft.

$199,900

Airbnb cash on cash: 9.12%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $3260

Traditional Rental Income: $1477

Airbnb ROI: 9.12%

Traditional ROI: 3.58%

150 KILLARNEY BAY COURT #5

Winter Park, FL

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

$315,000

Airbnb cash on cash: 4.83%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $3260

Traditional Rental Income: $2233

Airbnb ROI: 4.83%

Traditional ROI: 3.83%

2333 WESTMINSTER COURT

Winter Park, FL

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

$699,000

Airbnb cash on cash: 4.96%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $5745

Traditional Rental Income: $3035

Airbnb ROI: 4.96%