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

Search for properties for Sale in Winter Park, Florida. Browse all of Mashvisor’s listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 196 listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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%
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.	$474,900	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%
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 (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%
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%
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.	$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 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%
1523 MILLER AVENUE Winter Park, FL BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. 2-year builders' warranty and ...	5 beds \| 4 baths \| 3,164 sq.ft.	$1,499,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $5740 Airbnb ROI: N/A Traditional ROI: 2.81%
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: 3.75% Traditional cash on cash: 2.17% Airbnb Rental Income: $4337 Traditional Rental Income: $2615 Airbnb ROI: 3.75% Traditional ROI: 2.17%

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

There are 196 investment properties available for sale in Winter-park.

The ROI for Short-Term is higher than the Long-Term in Winter-park with average rental income of $undefined.

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%